Rob Walling
877 statements across 263 episodes · 227 bullish · 213 bearish · 13 people on the record · first statement Mar 3, 2020 by Rob Walling · across every show →
On the record as a speaker too: Rob Walling's record, appearances and statements → this page counts the times other people say the name.
Everything said about Rob Walling, oldest first
Mar 3, 2020 positive
Mar 10, 2020 negative
Walling: Bootstrappers endanger themselves by copying Basecamp's anti-tracking stance
“They can come out and say, we don't use any tracking, we don't use Google Analytics, we don't track open rates, and if you have a hundred million dollar business throwing off tens of millions a year in net profit with 50 employees, you can do that too. But if …”
Mar 17, 2020 neutral
Walling: Early-stage SaaS often churns large customers within weeks
“Because the challenge that I always see with especially early stage products that are really finding their footing, I'll say, is that you can get a big customer, but they'll stick around for two weeks or a month or two, and then they realize, wow, this just do…”
Mar 17, 2020 positive
Walling: Small startups beat larger competitors via founder access and agility
“When you are a small company, you are super agile with a lowercase a. You can get stuff done super fast. They can talk directly to the founder. These are the advantages that you can just use against larger companies over and over and over.”
Mar 17, 2020 positive
Walling: Logical reframing and contingency plans neutralize entrepreneurial anxiety
“I could actually look at it and say, well, how likely is that to happen and how bad would it be if that happened? So then, and then I can just try to right brain myself, or no, I'm sorry, left brain myself out of it. And it works for me to really look at it an…”
Mar 31, 2020 bearish
Mar 31, 2020 negative
Apr 7, 2020
Apr 7, 2020 negative
Apr 14, 2020 positive
Walling: Building To Sell From Day One Benefits Founders In All Scenarios
“I think that many people, especially, well, I think founders get involved in this kind of, this binary thinking about, I am never going to sell my business or I'm building it to sell. And I think building it to sell from the start helps you no matter what.”
Apr 14, 2020
Rob Walling: Most Successful Startup Founders Are Severely Under-Diversified
“Most entrepreneurs are just way under-diversified, right, because if their company goes under, I mean, many of us, most entrepreneurs who are having success like you had, literally have millions of dollars tied up into a small business, and they might have a 1…”
Apr 28, 2020 neutral
Walling: Customer discovery calls yield diminishing learning returns after 30 conversations
“Because at first it was like, well, you can learn and or you can try to get, you know, prospects try to get sales, but the learning becomes rote after you've had 10, 20, I think you said you did 30 calls or something like that. Like it just, it gets old having…”
Apr 28, 2020 positive
Walling: Lead SaaS marketing with positioning to avoid feature comparison races
“If you just throw a bunch of differentiators, these are our differences, then it feels like a feature race or a feature competition. But if you start at the top and you're like, this is our H-one, you know, this is our positioning and why we're different than …”
Apr 28, 2020 neutral
Walling: Predictable SaaS growth requires winning deals from cold traffic
“If all of your new customers come from current referrals, that's only scale so far. And I think for now, as you're doing things that don't scale and Scraping and clawing. I think it's fine. But longer term, I think at the back of my mind, it's like, how are yo…”
May 5, 2020 negative
Avoid business advice from founders who mistreat others
“Don't take business advice from people who have crappy personal lives, and my addition is, or who treat people in a way you don't want to treat people. And the reason I've added that is because, from what I've seen, you can be successful in business and treat …”
May 5, 2020 negative
May 5, 2020 negative
Competitors claiming 'plenty of room' will draft off your strategy
“So if someone ever, if you feel like you have this conversation and someone ever tells you, hey, there's plenty of market for both of us, just expect them to start drafting off you if they're not already. And what will be interesting is that you'll be able to …”
May 5, 2020 negative
May 5, 2020 neutral
May 5, 2020 neutral
May 5, 2020 neutral
May 5, 2020
Vet startup advice by asking if the founder succeeded twice
“When I see kind of a new expert or a new name come on the scene. I typically ask myself, have they done it at least twice? Obviously, there are exceptions, you know, Jeff Bezos has not built two Amazons, the Collison brothers, actually, I think they did have a…”
May 19, 2020 neutral
May 19, 2020
Walling: Founders Selling for Stock Must Secure Sufficient Upfront Cash
“If someone were to approach me and say, hey, I'm selling my startup and they want to give me a, an all stock deal, I, it would, it, like you said, it just really depends on the company and their prospects and where you think they're going, but almost in, in al…”
May 19, 2020 neutral
Walling: 70% of Software Companies Are Merely Slowing Down During COVID
“It's about 10 or 15% of companies that I have knowledge of are like taking off because of everyone's working remote. 10 or 15% are completely getting decimated because they are involved in, in things that when people are remote, they can't be done. And then th…”
Jun 2, 2020
Jun 2, 2020
Jun 2, 2020 positive
Walling invested in CartHook in September 2015 at $5K MRR
“What's a trip is that's when, at least the way I have it in my Google spreadsheet that I track my angel investments, I have September, 2015 of writing the first check, and my memory is you were around five K MRR at that time, so did you raise around that?”
Jun 2, 2020
Jun 2, 2020
Walling: Drip reached product-market fit at $12k to $25k MRR
“And so stage three, I have as a product market fit and the numbers that I wrote down, and this is starting to be from memory. So you got to give it a little fuzzy around the edges, but this from about 12 K MRR up to about 25 K MRR. And that was me and two W tw…”
Jun 4, 2020 positive
Walling: Early personal liquidity enables founders to take bigger long-term risks
“Having a small win early on and getting to some money that is in your bank account where you can then take bigger risks. Like I'm now in the position where I can just take bigger risks and I can grow a tiny seed, which is not going to really pay me much of any…”
Jun 4, 2020 neutral
Walling: Early-stage founders are often ill-suited to lead $100M companies
“Because oftentimes, like, the founder isn't the best person to run a hundred million dollar company. Because a hundred million dollar company with xt thousand employees Is very different skill set than what you and I have talked about today.”
Jun 4, 2020 positive
Jun 9, 2020 positive
Jun 9, 2020 positive
Baldacci: Stair-stepping bootstraps recurring revenue through progressive product complexity
“Stair stepping is an incremental approach to get you to the point of replacing your income and quitting your job with a higher than normal success rate. As Rob laid it out, it starts off with one off sales using a single channel and works up to the holy grail …”
Jun 9, 2020 positive
Suhm: TinySeed backed WP Pusher after Walling passed in 2015
“Five years ago in 2015, I pitched him on investing in WP pusher when I hit one K. And the funny thing is I got a very nice reply back that said, Congrats on the progress. Hit me up when you reached 10 K, but today Rob is kind of actually an investor in WP push…”
Jun 9, 2020 positive
Jun 16, 2020 neutral
Walling: Drip Had to Upgrade Its Database Every Four to Six Months
“I felt like with Drip, Derek and I, like we made, he made some, like a lot of great engineering decisions and he wrote really good scalable code, but we just, we kept outpacing it and we would have to every four to six months go back and do this and upgrade th…”
Jun 16, 2020 neutral
Walling: Fast-Moving SaaS Applications Never Have Clean, Gold-Plated Code
“As engineers, I know you and I would love, we want all the I's dotted, the T's crossed, we want it gold-plated, and I want everything to be clean. It's not always the reality. And in fact, it's, in my experience, never the reality, especially with a SAS app th…”
Jun 16, 2020 neutral
Walling: Drip Hit Scaling Limits with 30,000 Queries Per Second on Postgres
“That was the stuff we did for the first several years was like all the caching and all the, Grouping queries, and we had read replicas of our, of the database, but it was purely write load on a single data store. You have this Postgres database with 30,000 que…”
Jun 16, 2020
Jun 16, 2020 bullish
Walling: ~70% of SaaS portfolio companies see post-lockdown demand recovery
“Now, since then, with companies that I'm working with and have insight into, stuff has started picking up again, at least to some extent. There are still those big winners, you know, that are Let's say Zoom, you know, or Slack or someone in the podcast space, …”
Jun 23, 2020
Jun 23, 2020 positive
Walling: Contact-based SaaS must use feature gating for value-based pricing
“The only way to get around this, or to figure out how to get more You know, more value based pricing is to not just have it be number of subscribers. It's to introduce feature gating, right? Where, well, I know the agency wants an integration with some Salesfo…”
Jun 23, 2020 positive
Walling: Early-stage founders should spend up to 90 minutes on support tickets
“What becomes completely not scalable later is spending 60 to 90 minutes on a support ticket. But in the early days, I remember us doing it as well. I've done it with multiple products where I'm going above and beyond because you're scraping and clawing, not on…”
Jun 30, 2020 neutral
Jun 30, 2020 neutral
Walling: Drip pre-validation converted 4 to 5 paying customers from 17 conversations
“What I did with Drip was I went out and pre-validated that at least a few people would be willing to pay, at the time it was, I said, a hundred dollars a month, it actually wound up being 50 dollars a month for what I had in mind to build at Drip... And I did …”
Jun 30, 2020 negative
Jun 30, 2020 neutral
Walling: Launching an affiliate link won't attract promoters without active biz dev
“Running an affiliate program and just starting it and having a link available, almost no one is going to come in who has an audience and promote your stuff. This is more like business development. At this point, it becomes enterprise sales, or at least having …”
Jun 30, 2020 negative
Walling: Info product audiences rarely convert smoothly into SaaS customers
“If you have an audience and you've been selling them books and courses and stuff, and you think that you can sell them software in the same way, almost without exception, it doesn't work out that way. It is much, much, much, much harder to sell a SaaS or softw…”
Jul 7, 2020 positive
Jul 7, 2020 neutral
Rob Walling advises using email for non-urgent matters over Slack
“We say, hey, if you don't need to hear back on something for two, 3:04 hours, send an email. And if you need an urgent answer, and you are hung up, and you cannot proceed, or you're on a call, and you're right now, then Slack me, or frankly, send me a text mes…”
Jul 7, 2020 neutral
Jul 14, 2020 neutral
Rob Walling owned 12 diverse revenue-generating products at his peak
“When I had, at my peak, I think I owned 12 revenue generating products, I'll say, but one of them was like a collection of like six AdSense websites back when that was a thing, and then I had an e-commerce website for beach towels, I had a couple of different …”
Jul 14, 2020 neutral
Jul 14, 2020
Jul 21, 2020
Jul 21, 2020 positive
Aug 11, 2020 negative
Walling: First-time founders usually reach 15-20 employees before recognizing organizational chaos
“A lot of founders, especially first time founders, They get to the 15 or the 20 employee mark before they realize that they've created a big hairball and a big mess and no titles and no, and people have overlapping responsibilities and all that.”
Aug 11, 2020 positive
Walling: Slower SaaS growth allows higher revenue per employee
“The slower you grow. The less, you know, support you need, the less customer success, the less sales, the less, a lot of things. And I think you can have higher profit margins or at least a higher revenue per employee if you're on this really slow growth.”
Aug 11, 2020 positive
Walling: Competing is easy when market incumbents are widely despised
“If you can do that and build a better experience and then just not be, I don't know, kind of a company that charges people too much, and it makes it really easy to compete when your competitors are just widely despised, I think.”
Aug 11, 2020 positive
Founders can build ambitious startups without VC funding or sacrificing well-being
“You can build a startup, you can build a SaaS company without venture funding, and you can be ambitious Without having to put your relationships and your family life and potentially your health on the line in order to build a company.”
Aug 25, 2020 negative
Walling: Codebase Rewrites Take Five Times Longer and Solve Fewer Problems
“That's something that I tend to discourage people unless something is really a nightmare because it often takes five times longer than you think and it doesn't solve as many problems as you think, but there, of course, are exceptions to this.”
Aug 25, 2020 negative
Sep 1, 2020 positive
Sep 1, 2020 neutral
Sep 1, 2020 positive
Sep 8, 2020 neutral
Sep 8, 2020 positive
TinySeed founder sold for 10x revenue despite being under $100K ARR
“I'll keep some folks anonymous up for obvious reasons, but through stuff we've worked on, you know, with tiny seed, I know of a founder who got an offer and accepted it for, it was 10 X revenue and his revenue was approaching six figures ARR. He was still in f…”
Sep 10, 2020 positive
Sep 15, 2020 positive
Sep 15, 2020 neutral
Sep 15, 2020 neutral
Castro: Scripted video presenting requires acting, not just conversational delivery
“The difference between scripted and pre-recorded elements versus kind of the live conversational elements, Is acting. When you're in front of a camera and you have a script and there are peaks and valleys in the direction that that script is taking, you kind o…”
Sep 17, 2020 negative
Sep 22, 2020 negative
Sep 22, 2020
Sep 22, 2020
Sep 24, 2020 positive
Walling: Hiring beyond founders forces startups to standardize operations
“One thing you'll notice as an entrepreneur is that when you start to expand your team beyond just the founders, new hires propel you to get more organized. Creating standard operating procedures like Brian and Scotty are now doing is a big step towards cementi…”
Sep 24, 2020
Walling: Founders must make critical decisions with at best 70% certainty
“Being a founder is making decisions with incomplete information, and that's where you are. You don't have all the information, no matter how many conversations you have with current customers, prospects, bigger customers, LinkedIn cold outreach to larger firms…”
Sep 24, 2020
Walling: Repositioning creates transition periods where startups serve both markets poorly
“Making that, whether, whether you're going up market, whether you're changing from one vertical to another, whether you're expanding into other verticals, going from vertical to horizontal, there's all these changes you can make that are really scary while you…”
Sep 29, 2020 positive
Sep 29, 2020
Sep 29, 2020
Walling: Five of his 35 portfolio startups requested full codebase rewrites
“I'm 35 angel invest, you know, angel and tiny seed investments in, and I've had at least, I'll say four, four or five of the startups that I kind of advise or interact with say, I want to rewrite, we need to rewrite our code base.”
Sep 29, 2020 positive
Sep 29, 2020 positive
Wensing: Summit V2 rewrite immediately converted target-persona founders into customers
“So I think the short answer is yes, but I'll qualify that by saying I took it then to the customers that I was essentially targeting with this rewrite, right? I took it to them basically as soon as it was ready. And I said, aha, here's the flexibility you've b…”
Oct 1, 2020 positive
Walling: Raising prices attracts better SaaS clients who churn less
“Most businesses, if you start off B to C, you wind up trying to get to B to B eventually, and typically you start off as B to really small B, and eventually you'd want to raise your prices, because pricing doesn't just make you more money, but it gets you to a…”
Oct 1, 2020
Walling: Moving upmarket requires overhauling messaging, sales, and pricing over months
“This is the hard part of that process of going up market, right, is that you have two islands, a body of water in between them, and it's messaging, and sales process, and pricing, and positioning, and all that around going after one person, two person teams, v…”
Oct 1, 2020 positive
Oct 6, 2020 bearish
Walling: Pure maker mindset cannot scale SaaS businesses to eight figures
“Have I seen many six figure SaaS businesses built with that? Absolutely. Have I seen many seven figure businesses, SaaS businesses built with that mindset? A lot fewer. You know, and probably zero eight figure businesses that I think about.”
Oct 6, 2020 negative
Walling: SMB SaaS is not the optimal way to build big businesses
“And while that is totally possible, it is not actually the optimal way that I, you know, in my experience to build a big business quickly. Really, if you look at more of the SASTR model, which is, it's going after the big ticket, the fortune 1000 or the fortun…”
Oct 8, 2020
Oct 8, 2020
Oct 8, 2020
Oct 15, 2020 neutral
Walling: Startup founders inevitably second-guess past decisions every eight months
“That's going to happen again in eight months. You're going to look back at today and be like, what were we thinking with X, Y, Z? Maybe it's not pricing and positioning, but it's going to be something else. And then eight months from then it'll be the same. Yo…”
Oct 15, 2020
Walling: Product-market fit encompasses pricing, positioning, and acquisition channels
“A lot of people don't realize product market fit is not just building a product that people want and are willing to pay for. It's also having a good idea about your positioning and pricing, and some idea of channels where you can reach future customers.”
Oct 15, 2020
Oct 22, 2020 neutral
TinySeed early COVID portfolio: 15% struggled, 70% plateaued, 15% accelerated
“When I look across the portfolio of companies that are part of Tiny Seed's first two batches, or that I've invested in personally, it looks like they're about 15% that are having real struggles with the impact of the pandemic on the industry they serve. Anothe…”
Oct 27, 2020
Walling: Agency cash flow creates an addiction hindering product transitions
“And I've heard people call it like the, it's an addiction, right? The cash agency work or consulting is this cash addiction. And it's amazing. When you want to get to full-time income or hire quickly, but it's really hard to move away from, because as you said…”
Oct 29, 2020 negative
Nov 3, 2020 bullish
Nov 5, 2020 neutral
Walling: Arrival Fallacy Prevents Lasting Happiness From SaaS Revenue Milestones
“You have to figure out a way to celebrate milestones when you hit them, because it really is the arrival fallacy. You know, if you think, man, if I could just build a SAS app to a thousand dollars a month, I'll be happy. You're gonna get there, and then you're…”
Nov 10, 2020 positive
Walling: Owners plan 6 to 12 months ahead, unlike task-based hires
“So there are task based people, project based people and owners. I originally was saying founders, but I think it's more of the, really, I should say it as task mindset, project mindset, owner mindset. And I think that fits of like who can really own this whol…”
Nov 18, 2020
Nov 18, 2020
Nov 18, 2020 positive
Walling: Ship micro-products quickly rather than conducting lengthy customer validation
“For my bet, for my money, I'm probably gonna write a little bit of code and get it out there, and the learning starts with every bit of validation, and frankly, getting something out there quickly in this, if it's a small, small niche is not the right word, bu…”
Nov 18, 2020 positive
Walling: All 13 TinySeed Batch 2 portfolio companies are default alive
“The vast majority are already default alive businesses. I think every one of the 13 companies of batch two is default alive. Pretty sure. And The, if I were to put a number in it, 70% of batch one, maybe 80% are default to live.”
Nov 18, 2020
Nov 18, 2020
Walling paused retirement contributions during Drip cash crunches to fund growth
“I did stop, I will admit, at the worst times of Drip, when it was growing fast and we had cash crunches, I stopped contributing to retirement. My bet was that Drip would make enough money in the end, whether through an acquisition or whether through throwing o…”
Dec 1, 2020 negative
Dec 1, 2020 neutral
Dec 1, 2020
Walling: .NET Invoice generated $2,000 to $4,000 monthly after turnaround
“This was the first one that generated more than, you know, one or 200 dollars a month. And I eventually got it up. I mean, there was some, I remember the best month ever, I think was about 5000 dollars, but most months were between about two and four.”
Dec 1, 2020
Dec 1, 2020 positive
Dec 1, 2020 neutral
Dec 1, 2020
Walling: Tripling .NET Invoice's price from $98 to $295 sustained unit sales
“It was 98 bucks at the time, and I just did an experiment and said, selling about three copies a month right now, I'm gonna raise the price to 295 bucks, and the next month it sold three copies at 295 bucks, and it made 900 dollars the next month.”
Dec 1, 2020 positive
Dec 8, 2020 positive
Scaling a seven-figure SaaS application requires deep non-financial motivation
“But if I'm personally, I'm going to spend years building a drip, a seven figure, an eight figure app, I do believe that you have to care about that problem. Or care about that solution or care about that customer base. There has to be something drawing you in …”
Dec 15, 2020 positive
Walling: Scaling from product-market fit to $10M follows a repeatable blueprint
“Now, once you get, I mean, once you get to product market fit and you have customers and you start having channels at work, it kind of is, it's extremely repeatable. And usually there is a pretty solid blueprint of how to go from there up, how to go from there…”
Dec 15, 2020 negative
Dec 15, 2020
Dec 15, 2020 negative
Dec 29, 2020
Walling: Drip spent $8 on bulk shirts versus $21 for print-on-demand
“In fact, with drip, we'd print a hundred t-shirts at a time. And I believe the cost, I went directly to this printer that I had a good relationship with, and it was like high quality print, high quality shirt, seven bucks, eight bucks a piece. And then we had …”
Dec 29, 2020
Walling: Competing products must own positioning, control traffic, or be cheap
“I often say when someone's launching a new product, if you're going to compete with existing competition, which most of us these days are, I say, look, you should own a unique position, you should own a traffic channel, or you can be cheap.”
Dec 29, 2020 negative
Walling: Early startups need one-page plans and budgets, not formal business plans
“I think that the stance that I take is, I believe in having a marketing plan, and I believe in having a budget. And a marketing plan can literally be a one-page Google Doc with bullets in it, or a Notion Doc, and the budget is usually just a spreadsheet that g…”
Jan 5, 2021 positive
Jan 5, 2021
Walling: Founder Success Is Mostly Psychology and Decisions With Incomplete Data
“We know that starting a company is hard and that more than half of being a startup founder is managing your own psychology and that so much of this journey is making difficult decisions with incomplete information where the right answer is impossible to find t…”
Jan 5, 2021 neutral
Walling Does Not Regret Selling Drip, Regrets Staying Employed Too Long
“You know, you want to talk about regrets, it's not selling drip, it's staying working a full-time job too long, or it's not doubling down on things and taking bigger bets with different amounts of money that I had at the time.”
Jan 12, 2021 neutral
Jan 12, 2021 positive
Jan 12, 2021
Walling ran up to 12 automated website businesses generating monthly revenue
“At any given time, it was between eight and 12 different businesses running, but a lot of them were these small websites that were effectively on autopilot until something happened to them. So a lot of them were based either on Google ads, display ads, or SEO,…”
Jan 12, 2021 negative
Walling: Growing multiple businesses simultaneously requires dedicated executive leadership
“I don't think you can grow multiple businesses at once because of the focus that it takes, unless you are in that Richard Branson situation where you have a bunch of budget and you truly have GMs or CEOs or someone who's just, has the owner mindset.”
Jan 12, 2021
Jan 19, 2021 positive
Rob Walling chose Leadpages acquisition over others for trust and fair milestones
“We chose to sell to Leadpages rather than some other interested acquirers because I did trust that they were going to treat us well. And they did. And it wasn't based on any of the gotcha numbers, right? There were, there was no like revenue. There were no mil…”
Jan 26, 2021 neutral
Walling explored acquiring the second-largest tabletop gaming website after exiting Drip
“I looked around and I realized, hey, I don't want to build stuff from scratch because it just takes too long, so I have the means, I'm going to acquire something. And I actually got in a conversation with the owner of the second largest website for tabletop ga…”
Jan 26, 2021
Feb 2, 2021 neutral
Feb 2, 2021 bearish
Walling: Four percent retirement withdrawal rule is no longer safe
“Especially right now, like with stocks at historic highs, I don't know that the four percent rule is as safe as it used to be. I don't think it is personally, but certainly if you start notching down to a three and a half percent rule, a three percent rule, yo…”
Feb 2, 2021 negative
Feb 9, 2021 neutral
Lifetime deal launches often require temporary support staffing
“Recently folks who do these deals, if they don't already have at least one full-time support rep, in addition to themselves they often, like, staff up just a little bit. Because there's like two or three week period where there are hundreds and hundreds of req…”
Feb 9, 2021 neutral
Feb 16, 2021 bullish
Economic Downturns Create Great Opportunities for Bootstrapped Startups
“In fact, there can be even added opportunity in big economic bust times. You'll see all, you know, how many great companies came out of 2001 that were Almost bootstrapped or just had tiny amounts of funding, and then once the economic cycle comes back, these t…”
Feb 16, 2021
Walling is Writing a Book on Bootstrapping Multi-Million-Dollar SaaS
“I am working on my next book. And it is, in essence, it's not a sequel to Start Small, Stay Small, but it is like the next step. So Start Small, Stay Small focused on these tiny little niche businesses... This book I'm working on now is maybe that next step...…”
Feb 16, 2021 positive
TinySeed Paused Fund 2 for Two Months at COVID-19's Onset
“We started raising tiny seed fund two. We're going to start raising it in March Of 20 20, and we had all the assets and everything ready to start pitching it, and this happened, and everything just locked up, and we wound up waiting one month or maybe two to s…”
Feb 23, 2021
Rob Walling has angel-invested in 13 to 14 mostly non-unicorn startups
“I've personally, Angel invested in, I think it's maybe 13 to 14 companies, and more than half of those are just this. They are B to B SaaS companies that will probably never be unicorns, but they will be amazingly profitable real businesses that have the poten…”
Mar 2, 2021 bullish
Mar 2, 2021 negative
Walling: Selling SaaS lifetime deals penalizes your valuation during an acquisition exit
“Don't sell lifetime deals if you're in SAS. I mean, AppSumo is probably the one exception I would say. And if you're gonna sell, then you disclose when you exit that, Hey, we do have these users and you can, Give reports of this is how much they use on a whate…”
Mar 2, 2021
Mar 2, 2021 negative
Mar 2, 2021 positive
Walling: Framing yourself as a technical founder disarms enterprise sales prospects
“The other thing that I used to do, cause I don't like sales. I don't like sales calls, But I've done them when I needed to, especially in the early days of Drip. I did some for Hytale too, but especially in the early days of Drip, I would get on the call and I…”
Mar 2, 2021 negative
Mar 9, 2021
Walling regrets not raising a $300k to $500k angel round for Drip
“I think we were a little undercapitalized, like I would have, I should have raised an angel round, I would not have raised venture capital, I have no desire to go on that treadmill, but I probably could have raised 300 to 500 grand pretty early on, and at a go…”
Mar 9, 2021 positive
Mar 9, 2021 bullish
Walling invested 2% to 3% of his net worth in crypto post-exit
“When I sold drip, I was like, have some money to play around with. Like, I don't buy individual stocks. I tend to be, I buy assets, you know, I buy like index funds and stuff. I'm going to throw like two percent, maybe three percent of our net worth into crypt…”
Mar 23, 2021 positive
Mar 23, 2021 neutral
Mar 23, 2021
Mar 23, 2021 neutral
Walling: Drip pricing ranged from $49 to low four figures monthly
“So we obviously had the really wide funnel on the lower end starting at 49. I think even better, I mean, you know, if we had been able to have like a 19 dollar plan, That would have been cool. And then we had folks in the 500 to, I forget what the top end was …”
Mar 23, 2021
Walling: 10x to 15x Revenue Acquisition Offers May Be Once-in-a-Lifetime
“If you get an amazing offer, it very well may be once in a lifetime. And that's the point where I find some founders in where they're getting an offer for 10 times revenue, you know, or 15 times revenue. And it's like, not saying that'll never happen again, bu…”
Mar 23, 2021
Walling: Building verbatim customer feature requests creates bad software
“If you're a product person, you never take customer suggestions and build what they want because you wind up with crap software. You wind up with a million settings. You wind up with terrible UX. You wind up with terrible UI because customers are not product p…”
Mar 23, 2021 negative
Mar 30, 2021
Walling: Entering crowded markets requires capital, founder pedigree, or competitor weaknesses
“Entering a space with a market leader or even just a crowded space is totally doable under certain circumstances. Well, there's certain certain, if you raise buckets of money, you can at least take a go at it. If you're an experienced founder, maybe you've had…”
Mar 30, 2021 negative
Walling: Unethical shortcuts fail long-term because the SaaS community is small
“I think a lot of folks who get into building their own company, whether it's a SaaS company, whether it's info products, whatever they're doing, you think, well, I can get away with stuff. I can get away with something here and I'm going to have a short term m…”
Apr 6, 2021 neutral
Walling: Employees won't stay long-term for below-market pay without equity
“So if you're paying below market, like someone really either needs to have stock options or some other advantage that makes it worthwhile for them to You should do that because over the long term, no one is going to work for your company for years for below ma…”
Apr 6, 2021 negative
Walling: Transitioning from office to remote work is a hiring yellow flag
“The folks I've seen who try to transition from working in an office to working from home usually have a pretty rough transition. And that would be a, I would say at least a yellow flag for me if they didn't have You know, pre-COVID work from home experience.”
Apr 6, 2021 neutral
Walling: Leadpages had 170 employees and $38M raised when acquiring Drip
“And when we were acquired by Leadpages, which was a 170 people at the time, they had all of this figured out. And that is actually like one of the advantages, I think, of seeing both sides You know, basically working in a venture-funded company, they had thirt…”
Apr 6, 2021 positive
Walling: SparkToro operates with zero employees, hiring exclusively contractors
“And the alternative is I watch folks like Rand Fishkin, who's launched SparkToro, and they're doing plenty of revenue to hire as many people as they want, and they have no employees. They only hire contractors and consultants because they don't want to deal wi…”
Apr 6, 2021 positive
Apr 6, 2021
Walling: Drip required a $99 tier upgrade to remove its branding
“Back with Drip, we had a Powered by Drip link in our email capture widget that people could put on their site, and our lowest plan was 49, and that included the link, you couldn't shut it off, and at the 99 plan, you got whatever it was, double the subscribers…”
Apr 13, 2021
Apr 20, 2021
Startup Employees Don't Feel Like Owners Without Roughly 10% Equity
“Until someone has, I don't know, 10% equity. It depends on the person, but until someone has 10% equity, they don't really feel like an owner to your point of, Giving someone half a percent or one percent, it doesn't tend to mean that much.”
Apr 20, 2021 positive
Basecamp Pays Remote Staff at the 90th Percentile of SF Salaries
“Basecamp only has 55 employees because they've grown so slow over so many years, and they have so much net profit coming off that they pay all of their people no matter where they live. It's like 90th percentile of a San Francisco salary for the role, and they…”
Apr 20, 2021 neutral
Apr 27, 2021 bullish
May 11, 2021
Walling: Enterprise 6-to-12-month sales cycles require $50k to $100k ACVs
“Where it's a six month or 12 month sales cycle, and you're charging a 10th of what you should be charging, right?
These should be, you know, I don't know what exactly your product is, but these should be 50 grand, a hundred grand a year contract values, or els…”
May 18, 2021 neutral
May 18, 2021 negative
Walling: Bootstrapped startups with 3 or 4 co-founders have one too many
“Oftentimes when I see bootstrapped or mostly bootstrap companies with three or four co-founders, usually they're too many. Usually there's at least one too many and there's like a weak link. There's someone who's not Maybe holding up there”
May 25, 2021
May 25, 2021 neutral
Walling: Owner-Level Talent Rarely Succeeds as Part-Time Contractors
“These are senior level people who can get a lot of things done, but they're very expensive. They tend to be a hard to find and be out of, you know, the price range of a lot of bootstrappers. You know, if you're going to hire a contractor or someone who's going…”
May 25, 2021
Jun 1, 2021 positive
Walling: Silicon Valley Bank Underwrote Founder Mortgages Using 1099 Income
“A couple founders, someone had their mortgage lender, like, back out on them, 20 minutes before their close, and he had to go to Silicon Valley Bank, because they understand founders, and that's, they know what 10 99 income is, and they know what, you know, al…”
Jun 15, 2021 negative
Jun 22, 2021 positive
Jun 22, 2021
Bootstrapping a two-sided marketplace fails without an existing audience
“I think the one other thing is two-sided marketplaces are possible to bootstrap, but I think you need an audience. Not need is not the right word. I think you're almost destined to fail if you do not already have an audience with one side of that network, righ…”
Jun 29, 2021
Walling: Startup IP issues usually only surface during fundraising or M&A diligence
“Usually this doesn't come up unless you're gonna raise some money, or you're gonna sell your company. Right, and that's when somebody does some due diligence, because if you just run it for whatever, 1020 years, or you shut it down or whatever, no one really n…”
Jul 6, 2021 negative
Rob Walling avoids paying off his mortgage to keep investment capital liquid
“Is I actually going against the, I think, traditional wisdom is I try to keep as little cash in my home as possible. Some people want to pay their home off, but I view cash in a home as money that's tied up and money that I can't be using for all these other t…”
Jul 6, 2021 neutral
Rob Walling says Afford Anything podcast became repetitive and overly FIRE-focused
“And then the other one is Afford Anything, which is, is solid. I did feel like it got a bit repetitive and it's also a bit millennial for my taste. I don't know if that makes sense, but a lot of this stuff, it's more into the fire movement, financial independe…”
Jul 6, 2021 negative
Jul 6, 2021 bullish
Jul 6, 2021 positive
Jul 6, 2021 bearish
Rob Walling prefers holding cash over bonds due to low yields
“I'm not going to put a bunch of my money in bonds, you know, especially with as low as the yields are today. I think that maybe as I'm nearing retirement, I want to soften the blow, right? It just makes the ride a little less bumpy, but I prefer just to have c…”
Jul 6, 2021
Jul 6, 2021 bullish
Jul 13, 2021
Jul 13, 2021 positive
Jul 13, 2021
Walling: TinySeed was created because Drip needed a quick $200k infusion
“One of the reasons I started TinySeed is I wanted this fund to exist for me, because during the drip years, we needed money and we were doing all types of crazy stuff to cut costs. And it was super stressful. And I wanted to really quickly raise A couple hundr…”
Jul 13, 2021 negative
Walling: Founders aiming for modest exits shouldn't take venture capital
“If you're going to take funding to be like,
Hey, I would sell if I got an offer for twenty million, right?
To be upfront about that, and if the investor doesn't want to invest, then I don't think you should take the money, because you're going to have this con…”
Jul 13, 2021 neutral
Jul 27, 2021
Jul 27, 2021 bullish
Tech-enabled business banking will disrupt traditional banking like ridesharing disrupted taxis
“I feel like the tech has caught up. And that, that we are going to see like actual really solid banking products that make our lives easier, much the way that like we used to use taxis and then Uber and Lyft came along and it's like, no, it's a net win for us …”
Jul 27, 2021 negative
Jul 27, 2021 positive
Aug 10, 2021 positive
Aug 10, 2021
Aug 10, 2021 positive
Walling: Tying SaaS pricing to customer growth drives revenue without new acquisition
“Number one is the high potential for expansion revenue. And that is where, for example, with an email service provider, if I'm charging based on the number of subscribers you have, people who are successful are going to get more subscribers over time. It's jus…”
Aug 10, 2021
Aug 10, 2021
Aug 10, 2021
Walling: Enterprise SaaS agreements should require annual contract commitments
“And I would take it further and say annual, you know, that if you're going to be enterprise and you're going to go through this painful procurement process, I don't want someone sticking around for three months. They should stick around for a year if they're g…”
Aug 10, 2021
Walling: Demand enterprise pricing when customers request custom legal terms
“The moment someone says they want to edit your TOS, they want a custom TOS, they want their own, your price skyrockets instantly into the enterprise. So if you have a hundred or 200 dollar a month plan and someone says, oh, I need to run my terms of service by…”
Aug 16, 2021
Aug 16, 2021 neutral
Walling: Revenue-based financing typically demands $15k-$20k MRR and 6% top line
“In order to get revenues financing with anyone, you need to be about 15 or twenty-k MRR, and you take out a loan, and then you're on the hook for that. Sometimes there's a personal guarantee which is, you know, very different than this, and sometimes there's n…”
Aug 16, 2021 neutral
Aug 16, 2021 neutral
Walling: TinySeed only backs founders targeting $1M to $30M ARR
“One of the questions I ask is, do you want to build a seven or eight figure ARR SaaS company? Meaning, do you want to build a one to thirty million dollar, you know, bootstrap, mostly bootstrap SaaS company? The answer is yes, then, you know, then let's talk a…”
Aug 16, 2021 positive
Walling: TinySeed investment terms are modeled on Rand Fishkin's structure
“The terms themselves, the core of them were they came, Rand Fishkin, founder of Moz, left his venture-funded startup, came up with these terms for his next startup. So it's like, by definition, a founder came up with it for himself when he raised money. I had …”
Aug 16, 2021 bullish
Walling: TinySeed fourth batch pushes portfolio past 60 SaaS startups
“With this batch, this is our fourth batch we're funding, we're going to be north of 60 companies funded, and these are ambitious B to B SaaS startups, you know, in the six and seven figures of annual recurring revenue, and they're all, they're not venture trac…”
Aug 16, 2021 positive
Aug 16, 2021 neutral
Aug 17, 2021 positive
Aug 17, 2021 positive
Walling: Info product sites should offer immediate purchase and email-gated samples
“I would offer the ability to purchase from the site, of course, and I would do exactly what you're doing, which is at the top, send me a free sample chapter. Someone enters their email and you're basically offering them a chance to do both, right? Or do either…”
Aug 31, 2021
Walling: Drip grew from 10 to 100-120 employees post-acquisition
“Post acquisition, when the company grew from the 10 we were at during acquisition up to a hundred and, I don't know, a hundred, a 120. By the time that, that I left, we had a monitor with all our key performance indicators of the company.”
Aug 31, 2021
Sep 7, 2021 positive
Walling: Drip would have benefited from raising a small angel round
“Perhaps my biggest, it's not a regret per se, but one of the things that I would have done differently looking back building Drip Is I kept toying with the idea of raising a small round at two 50 to 500 K one time round just to do what you're saying, which is …”
Sep 7, 2021 negative
Walling: Startups should reach millions in ARR before hiring non-founder C-levels
“You should never hire a C-level person in the first, you know, in the first, you need to get to a lot of millions. I'll put in ARR before someone has a C in front of their title, unless they're a founder, in my opinion.”
Sep 14, 2021
Early-stage startup founders should collectively own 80 to 90 percent of equity
“Like the founders in an early stage company like this, raising a really a first or second round, pre-seed and accelerated round, a seed round. The founder should own 80, 90% of the company, you know, between that, if it's one or three or five, whatever. I mean…”
Sep 21, 2021 bearish
Email marketing will lose effectiveness as inboxes increase privacy protections
“With inboxes looking more and more at privacy, blocking open pixels, the effectiveness of email marketing will continue. It's certainly better than social media. But it's not as effective as it used to be. It's like doing SEO and having Google Analytics. It us…”
Sep 21, 2021
Startup founders should never promise employees they will never sell
“One thing that I'll say is, if you're starting a company, never tell people that you're never going to sell or go public. I'm not saying they did that. Other people have said, employees said they were under the impression they would never sell or go public. My…”
Jan 31, 2022 neutral
Jan 31, 2022
Aug 16, 2022 positive
Walling found quarterly retreats are too frequent for remote startup founders
“And what we found with our first batch is they, we got to the third one, and people were like, this is too often. It was actually, it was literally too often, and I had no idea that that would be the case. It is about, this cadence of about every six months se…”
Sep 22, 2022 negative
Walling: Hiring One Marketer for Both Strategy and Tactics Is a Mistake
“You know, I think a mistake that a lot of folks make is thinking that, okay, we have this money and we do need to invest in marketing. And so I'm going to try to find that unicorn marketer that can do everything right. That can do strategy and then do several …”
Sep 22, 2022 negative
Oct 18, 2022 neutral
Oct 18, 2022 neutral
Walling: App store connector plugins are virtually impossible to scale to millions
“And these are apps that have platform risk and they are pretty much impossible, virtually impossible to scale into the millions in revenue, but that's not what a step one business is for. Step one business is for you to learn that experience and get the skills…”
Nov 1, 2022
Nov 8, 2022 negative
Nov 8, 2022 neutral
Nov 15, 2022 neutral
Nov 15, 2022 positive
Walling: Founders at large conferences should skip sessions and focus on meetings
“I think you will get benefit from going, either one of you, and probably don't attend the sessions, but just try to line up meetings, talk to existing customers, try to get intros, like, and I talked a little bit about, like, luck surface area, this concept of…”
Nov 15, 2022 neutral
Walling: Hiring effectively is difficult without domain expertise in the role
“It is really hard to hire people when you're not an expert at the thing you're hiring. It's the unfortunate reality of like, I see non-technical single founders trying to hire that first developer and it's very tough. And so likewise, if you're trying to hire …”
Nov 15, 2022 bearish
Nov 22, 2022 negative
Rob Walling wrote shorter books to avoid traditional bookstore spine padding
“I wrote my first book was 40,000 words. It's like 204 pages in a pretty small format. And I did it because I was so tired of slogging through bull books that were padded to fit on a Barnes and Noble shelf and have a spine that was wide enough to whatever.”
Nov 29, 2022
Nov 29, 2022
Nov 29, 2022
Rob Walling grew HitTail to nearly $30,000 MRR before rewriting it
“And then I got Hittail up to about between 20 and, well, it was about almost 30 grand a month, and then when I was thinking about selling it, because Drip was taking off, one of the developers I'd hired to work on Drip, we were Ruby on Rails stack, I had him r…”
Nov 29, 2022
Walling: Early-Stage Startups Must Rely on Founder-Led Sales Before Product-Market Fit
“I'm going to make the assumption that you're early stage, you haven't found product market fit. And in that case, I cannot imagine anyone but the founder doing the sales. I don't know of a single instance where that has worked.”
Nov 29, 2022
Walling: Drip had 3,400 people on waitlist before product launch
“Drip had a 3400 person launch list before we launched, and that was because I was talking about it far and wide on this podcast, on every podcast interview that I was doing around that time, I was running ads to it, and we didn't have a product, right?”
Nov 29, 2022
Walling: Medical and Legal SaaS Cannot Rely on Self-Serve Customer Onboarding
“Yeah, I don't know of a single app aimed at this type of, you know, dentist, doctors, legal, Professional folks who are going to want to self-onboard and just figure stuff out. There are just so, so very few early adopters in those spaces.”
Nov 29, 2022 positive
Dec 6, 2022
Dec 6, 2022 positive
Vincent: Early startup competition is advantageous because it validates markets
“Competition doesn't matter. In my opinion, when you're talking about the beginning of seeding something, I mean, look at you and drip. I mean, you went into a space that had an insane amount of competition and you just executed and executed and all of a sudden…”
Dec 6, 2022 neutral
Dec 6, 2022 neutral
Dec 13, 2022 negative
Dec 20, 2022 bearish
Dec 27, 2022 positive
Dec 27, 2022 neutral
Walling: Drip charged full price during early access without offering discounts
“We did early access with Drip, and people paid for early access. They weren't given lifetime free use of the product. They weren't even given, you know, a discount. They weren't given a year free. We didn't offer any of that.”
Dec 27, 2022
Walling: Startups get copied after traction, not during ideation phase
“It's unusual for an idea to get stolen in the idea phase. Usually it's, you launch something, it gets some traction, and then some people on Hacker News or Indie Hackers or Quora or whatever, Stack Overflow, wherever you're talking about it, or even going on p…”
Dec 27, 2022
Dec 27, 2022
Dec 27, 2022 negative
Jan 3, 2023
Rob Walling: Over-indexing on DIY scrappiness leads to bootstrapped founder burnout.
“The shadow side of that is you can't then take that too far. You get down to the point where you don't want to bring anyone in, because, well, I can do everything, because I'm the entrepreneur, and even if I have the money, I'm gonna keep more money for myself…”
Jan 10, 2023 positive
Walling: Bootstrapping equalizes founders because customers only care about problem-solving
“Bootstrapping especially is just such, such a great equalizer. It's such a platform that does the tool solve a problem that's worth paying for, then people will pay for it. And they usually don't care who you are in most cases, you know, they don't care where …”
Jan 17, 2023 negative
Jan 24, 2023 positive
Jan 31, 2023 positive
Walling: SaaS enterprise contracts should mandate 5% to 10% annual price increases
“With companies that I advise that are selling into the enterprise that are actually doing annual contracts, it's standard recommendation at this point to say, if you're signing an annual contract with a customer, build in an annual price increase. Five to 10% …”
Feb 7, 2023 neutral
CoSchedule founders bought out their venture investors in 2022 after raising $5M
“CoSchedule, I found by digging through the internet, through various sources, raised five million in funding. But this year, or I guess it's last year now, twenty-twenty-two, bought, the founders bought out their investors”
Feb 9, 2023
Feb 9, 2023 neutral
Feb 9, 2023 positive
Feb 9, 2023 neutral
Feb 9, 2023
Walling: TinySeed Accelerator Sweet Spot Is $2K–$3K to $50K MRR
“For me though, in between that two and three up to about I'd say most recently about 40 K MRR, 40 or 50 is where we've been funding. I think if you're above 40 or 50, we should probably talk about you using our syndicate to get funded unless you really want to…”
Feb 9, 2023 positive
Feb 9, 2023 positive
Walling: TinySeed Has Accepted Startups Facing Significant Platform Risk
“In my opinion, it is not Too much platform risk to apply. We have folks with as much or more platform risk who have gotten into the program, and it's just about managing that and understanding that risk is there and figuring out ways as you grow to mitigate it…”
Feb 14, 2023
Feb 14, 2023
Walling: Cold outreach for validation should initiate conversations, not link landing pages
“If I were to cold email, I wouldn't send them to a landing page. If I was doing cold outreach, I would just be wanting to have a conversation. Like, I'm building this thing. I'm not selling anything yet. I'm a founder. I'd love to find out if you have this pai…”
Feb 14, 2023
Feb 14, 2023 positive
Feb 28, 2023 positive
Feb 28, 2023 bearish
Walling: $10k SaaS acquisitions typically buy codebases without momentum
“Spending 10,000 dollars to acquire something, and these days, unless you get a really good deal, that doesn't get you much. It might get you a code base, and look, code base is fine, but what I would really be looking for if I were in your shoes is some type o…”
Feb 28, 2023
Feb 28, 2023 neutral
Walling estimates 85% to 90% of bootstrapped founders are white men
“And obviously with the broader kind of bootstrapped world being, I don't know what, I don't remember exactly what the numbers are, but it's even 90%, 85% white males. That is you know, an unfortunate reality of it is that By proxy are 85 or 90% of the podcasts…”
Feb 28, 2023 neutral
Walling acquired HitTail in 2011 by cold-emailing owners of neglected apps
“You can do what I did, which is to cold email a bunch of apps that you think people have neglected, or that are out of date, or that have not been updated in a while. And ask if they might be interested in selling. And that is how I acquired Hittail.com back i…”
Mar 7, 2023 positive
Walling: Small product wins build confidence and skills for larger ventures
“And that's one of the reasons that I'm so pro on the stair step approach is that if you get these small wins and you build a product doing a thousand or 5000, you then have the confidence, the revenue, you know, some skills that you've built to then do it agai…”
Mar 14, 2023 negative
Walling: Founders should avoid high-ACV markets unless they can sell
“If you're going to sell to banks, insurance companies, 500 dollars, 10,000 a month, you need to learn how to sell, right? And if you don't know how to sell, then don't go into that space unless you have a co-founder who could do it, or unless you want to learn…”
Mar 14, 2023 negative
Walling: Raising an investment round is rarely worth doing below $75,000
“And pretty much the blanket advice I give is like, it's almost not worth doing if you're not going to raise, let's say, a hundred grand. Maybe for like, 75, you know, I mean, because it's time consuming, it's distraction, it is legal fees, and again, how you s…”
Mar 21, 2023
Mar 21, 2023
Mar 21, 2023 neutral
Mar 21, 2023 positive
Walling: An 'Armageddon beer' trigger helps founders evaluate business-ending crises
“And I think someone asking if you need the Armageddon beer, whether it's literally someone asking that, or if you have an object or a human that can level set and reset your mental model to, is this actually business ending? I think that's a tremendous superpo…”
Mar 28, 2023 positive
Walling: Listeners mistook an AI clone of his voice for a cold
“So about a month ago, I took my, you can train it with your own voice, snippets of your own voice. So I uploaded snippets of mine and trained it to sound like me. And then I typed out a piece of the intro of this podcast and I cut it in just to see if anybody …”
Mar 28, 2023 negative
Mar 28, 2023
Apr 4, 2023 negative
Walling: Single-stack engineers lose technical malleability after five years
“I don't know that if you've worked at a job for five or 10 years in the same technology, same code base, I don't know that you have that malleability. And so I think maybe that was an advantage that I had, having worked in so many code bases.”
Apr 4, 2023
Walling: Seat-based pricing works best when users see different data
“The basic piece of how to avoid login sharing is usually that if two people log in from the same company, they need to see something different. Right? In order to charge by seat. So if you think about logging into a CRM like Salesforce or Close or even like Tr…”
Apr 4, 2023 positive
Walling: Life-changing wealth came from WP Engine angel investing and exits
“The life-changing income that I've received has been from selling my own companies and from angel investing in companies like WP Engine and a few others that had these massive returns on my investment or on my time, and the tax advantages were there as well.”
Apr 4, 2023 neutral
Walling: SaaS ideas cannot be fully validated until customers pay and retain
“The thing to keep in mind is you're never going to get to 100% validation. I say that all the time. When you come up with a brilliant idea, you're probably at 10% out of a hundred that anyone else needs this. And then as you have conversations or as you drive …”
Apr 4, 2023 positive
Apr 4, 2023 negative
Walling: Price hikes on existing users demand a 15% MRR gain
“There's Rob's rule of 15, which is if you're not going to make at least 15% more MRR by raising prices on existing people, then it's not worth the headache because people get mad and there's a bunch of support and it's just a lot of effort.”
Apr 11, 2023
Walling: SaaS startups cannot beat incumbents without a distinct positioning angle
“If you are the same as other large competitors, and they have more money, and more brand name recognition, and it's just a stronger brand, you will be a commodity. You will not grow. Just because it's a huge market, doesn't mean that anyone will sign up with y…”
Apr 11, 2023
Walling: Under 5% of TinySeed Founders Had Pre-Existing Audiences
“So with TinySeed, for example, we have, I believe it's about a 107 companies that we funded, and I think we're going to fund another, what, 20, 25 here in the next month or two. It's a lot of companies, and less than five percent of them had an audience before…”
Apr 11, 2023 positive
Apr 18, 2023
Apr 18, 2023 bearish
Walling: Founders should not raise VC before finding product-market fit
“I hate it when people raise VC on an idea. I hate it when they raise five million dollars when they're at 20 K a month, and they still don't have product market fit, and they're just gonna, they're gonna burn through the money, right?”
Apr 18, 2023 positive
Walling: Drip's first non-developer hire was customer success
“My first hire that was not a developer was a customer success manager, and she dramatically improved The number of people who not only converted to customers, but who got onboarded and stuck around because the price points were worth it.”
Apr 18, 2023 positive
Prioritize marketing and manual onboarding over fixing product bugs first
“It's not an either or, it's do both, but prioritize the marketing and sales and just do everything manually to work around The bugs that you currently have, while in the back of your mind thinking, I'm gonna knock these out one by one.”
Apr 18, 2023
Walling: Jason Cohen paid consultants' hourly rates to validate WP Engine
“I know that Jason Cohen, when he was vetting WP Engine, he would actually pay consultants or agencies, or he would offer to pay. He's like, I know your rate is a hundred dollars an hour, And I'll pay you know, for a half hour or for a full hour of your consult…”
Apr 18, 2023 positive
Walling: Funding is best used after establishing a repeatable growth engine
“If you have an engine that's working and over time you can put a dollar in and get two, three, four dollars out over the next year or two, this is where funding is the ideal solution. That's really what funding should be used for, right?”
May 2, 2023
May 2, 2023 positive
Walling: TinySeed and MicroConf operate internally like startups, not passive funds
“When I first meet people and they say, what do you do? I say, I'm a startup founder. I run startups. Like, that's what Tiny Seed and MicroConf really are. Like, Tiny Seed happens to have raised funding to invest in other startups, but internally we are still, …”
May 2, 2023 neutral
Rob Walling: Organic SaaS Growth Is Harder, Making Seed Funding Advisable
“The content bar, especially with AI now, but even before that, like, 1015 years ago, I could hire someone to put out articles and just build links, like almost buy links from, what were they, blog networks or whatever, and you could rank in Google, and you can…”
May 2, 2023 positive
May 2, 2023
May 2, 2023 bullish
May 2, 2023 positive
May 2, 2023
May 2, 2023 negative
May 2, 2023 positive
May 2, 2023
May 2, 2023
Rob Walling: Cloning incumbents fails; SaaS startups need opinionated, niche positioning
“The biggest mistake I see is someone building, trying to build the exact same thing as a bigger competitor, and they'll be like, well, the market's huge. I just need one percent of it. It's like, no, no one's going to stand up. You have to be opinionated and e…”
May 2, 2023
May 9, 2023 negative
May 9, 2023
Walling: Outside capital creates an implied agreement to focus and deliver investor returns
“Once you take investment from someone, even really nice investors who are not putting a ton of pressure on you to grow, there is still an implied agreement that you will focus. And that you will do your best to grow the company like that. You'll work hard to b…”
May 9, 2023 negative
May 9, 2023 positive
Walling: Career growth requires taking ever-increasing, manageably sized risks
“You want your career to be a series of ever-increasing and manageably sized mistakes. And I like it because I think it's a reminder to each of us, no matter if you're just starting out, if you're mid-career, If you're later in your career and you've had some a…”
May 9, 2023
May 9, 2023 positive
May 23, 2023
Second-time founders consistently underestimate the long timeline to product-market fit
“And you just forget that the first like 12 months, you think you're gonna get there faster because you know what you're doing and you have the money and you have the focus and you should be able to get there faster and you don't, right? It's super frustrating.…”
May 23, 2023
Bootstrapped SaaS businesses typically sell for 4x to 6x SDE multiples
“Yes, the market is what four to six ish SDE. You know, again, you can get three if you're, 2.7 if your app is declining, and you can get seven if it's in a super hot space and growing rate, you know, there's all these numbers, but like four to six I think is a…”
May 23, 2023 neutral
Founders must abandon technical preferences and accept simple code to make money
“If you want to make money from something, then know that you're gonna have to
Do away with your technical preferences, and there's a decent chance you're going to build stuff that's going to be too simple for you, or you acquire something and it has a shitty …”
Jun 6, 2023
Jun 6, 2023 positive
Rob Walling: Free setup services at Drip boosted onboarding and customer retention
“With Drip, we would take a customer's ebook or a series of blog posts and we would turn them into an email mini course. So it was copying, pasting, formatting, some things like that. And so I had essentially a support person who took that over and would build …”
Jun 6, 2023 negative
Jun 20, 2023 positive
Walling: Ruben Gomez grew tens of thousands of monthly uniques pre-launch
“When Ruben Gomez went to do SignWell, he started SEO a year, at least a year before they launched the app. He got a domain. He started building templates for contracts or, you know, whatever he did for his SEO stuff, he had tens of thousands, if not more, uniq…”
Jun 20, 2023 negative
Jun 20, 2023
Jun 20, 2023 positive
Jun 20, 2023 negative
Walling: Non-technical SaaS teams face ongoing product issues for years
“I see the companies who don't have a technical co-founder where it's just a subject matter expert or a subject matter expert and a salesperson, for example, the number one issue for them constantly ongoing, sometimes for years is the product.”
Jul 4, 2023 negative
Walling: Conferences should avoid celebrity keynote speakers who leave immediately
“We absolutely get suggestions for speakers like Gary Vee, Seth Godin, whatever other celebrity person who talks kind of about entrepreneurship or marketing or whatever. Look, I don't mind those people. I don't, I like Seth Godin, right? I would love, I've seen…”
Jul 4, 2023 negative
Jul 4, 2023 neutral
Walling: Every founder is struggling with unseen mental health challenges
“At any given time, all of us, each of us is struggling with something. Sometimes it's imposter syndrome. Sometimes it's mild depression. Sometimes it's deep depression. Sometimes it's anxiety. Sometimes it's, it can be OCD, you know, just whatever we are worki…”
Jul 4, 2023 neutral
Jul 11, 2023
Walling: Left $200K Consulting Income for $100K Product Salary
“When I stopped consulting, I was making between 202 150,000 dollars a year, and we lived in an apartment in New Haven, Connecticut, and then Boston, so that just our expense wasn't that much. We were moving around because my wife, Sherry, was just wrapping up …”
Jul 11, 2023 neutral
Walling: $10M Exit Funds Life, $500K Buys a Few Years
“Whether you make Half a million dollars in an exit or five, ten million. You have some modicum of freedom at that point to work on what you want for different periods of time. I would say at ten million, you're probably for the rest of your life. And you know,…”
Jul 11, 2023 positive
Walling: Adding $5k MRR to a Mature SaaS Adds $300k Enterprise Value
“When you are building a SaaS company, and we'll just take a generic SaaS revenue multiple, once you're above about a million, million and a half, that, let's just say you'll get five X of your ARR. So, well, let's say you add five K of MRR in any time period, …”
Jul 11, 2023
Heimanson: Datamove charges customers for custom features while retaining IP
“So this one around, and the way I do it now, Rob, is if someone really wants something really important, they think it's huge, I will give them a proposal for us to build it, they'll pay for it, but I will make it available for every other user of ours.”
Jul 18, 2023 bullish
Jul 18, 2023
Walling: Recovering from severe burnout requires stopping work for weeks
“One of the biggest things, if you do encounter burnout and you go into full-fledged burnout, a big thing you have to do is just stop working. You know, sometimes it's a month or two, and it's usually when you feel like you can't do that, and I'm nowhere near t…”
Jul 25, 2023 negative
Walling: Communities offer zero SEO benefit and fail without critical mass
“In addition, a community is going to be private, so there's really no SEO benefit. Maybe you have a landing page or something, but now you're trying to get enough people in there. That you need the community to work. It doesn't work with 10 people. A directory…”
Jul 25, 2023
Jul 25, 2023 bearish
Walling: Niche SaaS founders should avoid building communities without existing audience
“But if I were running a SaaS aimed at a niche, community would be far down on the list of things that I wanted to start. Unless I felt like there was an extreme vacuum in the space and I already had an audience. Where I could kickstart that community.”
Aug 1, 2023
Walling: Founders exiting a business should take three to six months off
“And here's what I tell anyone who asks me these days when they say I'm going to exit, I say, take three months off, maybe six, don't do anything. You can write in a notebook of all the ideas you have. You can maybe buy domains. If you give yourself a 48 hour c…”
Aug 1, 2023 negative
Walling: No SaaS business can run on permanent passive autopilot
“Really there's nothing, there's no SaaS company, for example, that's on permanent autopilot.
It just doesn't happen.
They always decline because Google smacks you because, you know, a competitor comes along.
It just happens.
I've never seen one that's like, oh…”
Aug 1, 2023
Walling: Achieving financial freedom without purpose is disorienting for entrepreneurs
“I talk a lot about my three kind of North Stars, freedom, purpose, and relationships. And most of my adult life I was seeking freedom, and then you achieve it, right? You achieved freedom where it's like, you may have to work years down the line, but you certa…”
Aug 1, 2023 positive
Walling: Past lifestyle SaaS generated $30K monthly on 12 hours a week
“I had an awesome business doing 30 K a month with two K in expenses, and I worked 12 hours a week, you know, and that is, it's like super cash flow, great lifestyle, but that business was for reasons, for a bunch of reasons, platform risk and churn and such, w…”
Aug 8, 2023 positive
Aug 8, 2023 positive
Aug 8, 2023 bearish
Rob Walling hesitates to invest in purely pay-as-you-go pricing startups
“I would tend to hesitate to invest in a company, for example, that was all pay-as-you-go. Because SAS is the best business model in the world, and you don't have all the advantages of SAS going up into the right, and of the exit multiples, and of all the thing…”
Aug 15, 2023
Aug 15, 2023 positive
Aug 15, 2023 negative
Audible takes 75% cut on non-exclusive audiobook sales, Walling says
“I actually did not know that on Audible, they take 75% of the royalties, even though I wrote the book, I own it. I recorded it, produced it, and all that, but if I agreed to not sell it anywhere else, they only took 60%, so I get 40, and if I wanted to sell it…”
Aug 22, 2023 neutral
Steers: Founders under $300K in revenue must handle all sales personally
“If you are in the zero to 300 K, the only things you should be outsourcing are tasks that don't have to do with sales. This is you doing bookkeeping, automation stuff, like you should be doing all of the selling if you're at that level.”
Aug 29, 2023
Aug 29, 2023 positive
Walling: Cold outreach to dated software generates uncompetitive acquisition deals
“Back in 2010, I sent 50, maybe even 75 emails to products that looked dated. They just weren't being maintained anymore. They looked crufty. They looked long in the tooth. And I basically generated my own deal flow. And that's where I was then the single buyer…”
Sep 12, 2023
Sep 12, 2023 neutral
Walling: Drip launched in phased batches from 300 up to 600 users
“With Drip we had 3400 people on an email list, and I think I started doing it in, I think the first launch was to 300, and then we did another 300, and I realized we could totally handle it, so then we went up to like four or 500, and I believe by the end we w…”
Sep 19, 2023 positive
Walling: Phased product rollouts are far more optimal than massive public launches
“I've done it myself, I've seen other folks do these phased launches, and that is, I would say, a much, much more optimal way to bring a product to market, rather than try to do the big product on Reddit Hacker News launch, where this is what you run into.”
Sep 19, 2023
Sep 19, 2023
Walling: Structures early employee equity to fully vest upon a company acquisition
“When I have issued equity in the past, I have made it fully vest if we were acquired because I wanted my people to own that equity or own those options to be able to purchase the options. When the acquisition came through such that they were not compelled to s…”
Sep 19, 2023
Walling: Acquirers primarily seek the team in over 99% of startup acquisitions
“Realistically, in almost all of the acquisitions that I see, maybe, maybe it is truly all, but in 99 plus percent, the acquirer wants the team. The acquirer wants the team. It's very unusual that they just are acquiring technology, and unless you've built some…”
Sep 19, 2023
Walling: Only 1% of Drip users used split testing despite widespread demand
“So when we were growing Drip, people would Say, do you have split testing? Because we need to split test everything, and eventually we built split testing and one percent of our users used it, but everyone thought they wanted it.”
Sep 19, 2023 positive
Walling: Mock features work for corporate procurement checklists, not end-user SaaS
“It doesn't work when you're building software for a hundred dollars a month or when you're selling to the end user. But if you are selling to some corporate procurement person, AB is 100% correct. I've seen it myself. Ridiculous checklist requirements are very…”
Sep 19, 2023
Walling: Drip plateaued at $9K MRR before finding product-market fit in 2014
“With Drip, we did do a Drip two point O launch because the one point O launch happened in say November of 2013. And we peaked at eight or 9000 MRR and then plateaued because to your point, our pricing wasn't figured out. Our features were not there. We didn't …”
Sep 26, 2023 positive
Sep 26, 2023 negative
Walling: Customers lack product sense and long-term UX vision to design software
“Your customers are not going to have the product sense to be able to design your product. They don't have the vision, For what it needs to look like. They don't have the vision for what the UX needs to be to keep the elegance in. They see a problem they have a…”
Sep 26, 2023 negative
Sep 26, 2023
Oct 3, 2023
Walling: New products require asymmetric upside, limited downside, and fast validation
“In addition to his vision, or his intuition is like, does it have asymmetric upside if it works? Is the downside if it fails not catastrophic? And how quickly can you test this? How quick, or how quickly will you know? Because usually, yeah, another product is…”
Oct 3, 2023
Walling: Use product feedback to creatively iterate, not for binary validation
“It shouldn't be this black and white thing. It should much more be around, am I able to take your feedback and creatively incorporate it into my idea? Or is, or if I'm really getting bad signals, I should just scrap it all together.”
Oct 3, 2023 negative
Oct 3, 2023 negative
Walling: Founders addicted to launch dopamine should avoid second products
“Are you the indie hacker who's in the trap of launch? It didn't take off immediately on product hunt. I'm just going to give up and move on to the next thing because it's not working. And it's a siren song of over and over because you get the launch dopamine, …”
Oct 3, 2023
Walling: Bootstrapped teams grow faster by focusing entirely on one product
“Because as bootstrapped entrepreneurs, or mostly bootstrapped entrepreneurs, like, even if you had a team of five, 10, 20 people, if you put all those people on one product, it's gonna grow faster. It should grow faster, but if you split that focus between two…”
Oct 3, 2023 negative
Walling: Multi-product indie hackers rarely reach seven-figure revenue
“Now there is this flip side, the indie hacker lifestyle dream, right, that you're talking about where you get the portfolio and you're, you know, perpetually traveling or you're just working the four hour work week. That's not a bad thing, but it, to your poin…”
Oct 10, 2023
Walling: Live events fundamentally rely on sponsor subsidies to be viable
“All events need sponsors in order to make them happen. I was under the impression that, oh, you know, when people charge a thousand dollars for a ticket or 500 dollars for a ticket, they sell those tickets and that pays for the event. But no, they're all subsi…”
Oct 17, 2023 neutral
Oct 17, 2023 negative
Oct 17, 2023 neutral
Oct 17, 2023
Oct 17, 2023
Walling: Blindly building customer feature requests leads to fragmented clones
“The problem is, if you just listen to your customers and build what they tell you, A, you're gonna build a bunch of crappy features that are disparate and all over the place, and B, they're pretty much gonna have you replicate whatever competitor they switched…”
Oct 17, 2023 negative
Oct 17, 2023
Walling: Fractional CTO equity should usually be 0.5% to 1% over two years
“But if you get to the point where you are going to give them equity, usually I think of it as an advisory portion of shares, which is usually, as I said earlier.5 to one percent, and it usually vests monthly over two years. I'm saying usually these are rules o…”
Oct 24, 2023 neutral
Oct 31, 2023 negative
Walling: Early-Stage Anti-Churn Tactics Mask Lack of Product-Market Fit
“I've seen founders who are doing, again, they're early, five K a month, one K a month, 20 K a month, and they're churning too high, and so they start implementing these anti-churn tactics, forcing everyone to go annual, or making that the default, or making en…”
Oct 31, 2023 negative
Oct 31, 2023 negative
Oct 31, 2023
Oct 31, 2023 negative
Walling: Needing four-plus words to describe software signals danger
“When you go beyond that, when you start using four or more words, this is Rob's completely made up rule of category creation, but when you start needing four or more words or a complete sentence to describe what your product does, you're in the danger zone, in…”
Oct 31, 2023 negative
Nov 7, 2023
Nov 7, 2023
Startups sacrificing code quality for speed often stall at $1M–$5M ARR
“Who hires a dev or has kind of a minority technical co-founder and they drive them and push them to write code faster and faster and faster and the code is and then they get to a 1,000,003 1,000,005 million in ARR and they stop. They lock up. You can't build f…”
Nov 7, 2023
Nov 7, 2023
SaaS founders should route demo requests based on prospective contract value
“If someone comes along
To request a demo, I want to route them to the appropriate demo based on how much they're going to be able to pay me, or how much they will be paying me. I'm not going to do a demo for someone paying me 49 dollars a month, unless it's re…”
Nov 14, 2023 positive
Walling: Early founders should manually onboard their first 20 customers
“Nowadays, anyone who's starting out, I would say manually onboard your first 20 customers. Don't write any code, figure out what the hiccups are, figure out how long it takes them to get onboarded and to get value, and that will inform the duration of your tri…”
Nov 14, 2023 negative
Walling: Growing multiple SaaS businesses at once is an anti-pattern
“Like, you can't grow three SaaS companies at once. No one does this, right? It's an anti-pattern. You can grow one and then have a couple that are flailing around, and so if people see you tweeting about one, two, three, four, five different projects at once, …”
Nov 14, 2023 negative
Walling: TinySeed never invests in founders running multiple side products
“When we're interviewing founders for TinySeed, if we get a lot of pushback about asking them to, say, go full time on their startup, or someone who we notice is all over the place doing the indie hacker dream where they have five or six different products, I w…”
Nov 21, 2023
Nov 28, 2023 positive
Nov 28, 2023 bearish
Dec 5, 2023 positive
Walling: Building aligned products enables powerful cross-promotion across one audience
“It's a nice to have if your projects are related enough that you can contact an existing audience that you have, rather than doing what I used to do, where I had nine or 10 products completely unrelated, so none of the customer bases could be co-promoted to an…”
Dec 5, 2023
Dec 5, 2023
Dec 5, 2023 positive
Walling: Targeting two related verticals early works if product usage is identical
“Literally going after two verticals at the start, it's not a hard pass for me. Just because we talk about niching down or focusing our product doesn't mean that we can't have a couple highly related verticals, especially if both of them onboard and use the pro…”
Dec 5, 2023
Private equity firms avoid partial buyouts for early-stage micro-SaaS
“It's not gonna be at 18 K per month there. I don't know of anyone that's willing to do partial buyouts at that early a stage. If there are any, there's probably one or two, and they're probably extreme value buyers, meaning they're gonna give you very low mult…”
Dec 5, 2023
Dec 5, 2023 neutral
Dec 5, 2023
Remaining co-founders should discount cash buyouts below market rate
“And usually the buyout is a little less, it's usually less than market rate for that, that app if you're buying them out in cash, because it just should be, right? Because you're left with the business and you now have to slash get to run it.”
Dec 5, 2023 positive
Dec 5, 2023 negative
Privacy purists on forums are 'assholes' about bulk email being spam
“There are privacy purists on the internet who say anytime any bulk email is spam, and they're just assholes about it, you know, and we would get this complaint all the time, and we'd have these people who were either, they were so far off in their perception o…”
Dec 12, 2023
Walling: Introverted Founders Should Sell Transparently Rather Than Fake Extroversion
“And so I would just be pretty honest with them and be a human upfront about this is who I am and this is the goal of the call rather than trying to talk them into it or trying to act like someone that I wasn't, right? I didn't try to channel some fake extrover…”
Dec 12, 2023 negative
Dec 12, 2023
Rob Walling: Skip Stair-Step Method If You Have Urgent Startup Idea
“Like, the stair-step method is, I don't have any ideas and I'm gonna go try to do it in a repeatable, Predictable fashion. That I have a decent confidence that I'm going to build it up over time, and I'm going to have some moderate successes over time that bui…”
Dec 12, 2023 negative
Walling: High-Touch Sales for Low-Paying Customers Creates an Unviable Business
“If they all want high touch, but they're super cash strapped, Let's say they're a school, or a library, or a non-profit, and they need the high touch, but they're only willing to pay 30 dollars a month, that's a tough business. I would say, I don't want to say…”
Dec 12, 2023 bullish
Walling: MarTech offers huge startup opportunities due to low switching costs
“Because if we're going into MarTech, marketing technology, where the switching costs are low, and there are no network effects, and there are some big brands in the space, but people don't like them, I mean, there is huge opportunity, in my opinion.”
Dec 19, 2023
Walling: Founders Frequently Forget to Revisit Outdated SaaS Onboarding Flows
“This is one of those things that can easily get lost and forgotten because you deploy it once and you polish it up. And then a year later, your app, your positioning, your entire funnel, even maybe even your ideal customer profile has changed, but we just forg…”
Dec 19, 2023
Walling: TinySeed Is Intentionally Not the Cheapest Money
“We are not the cheapest money.
By design, we are not the cheapest money.
If you want cheap money, go to a doctor down the street, a dentist, maybe a local angel group, go try to raise on, you know, on Sand Hill Road, go to one of kind of the copycat, like the …”
Dec 19, 2023
Walling: SaaS Startups Should Leverage Pricing Power at $1M-$2M ARR
“By the time I'm building a brand, by the time I'm at a million ARR, two million ARR, and people list me as one of the top two or three
Options in a space.
I say list me.
They list my product, my company as one of the top two or three options in a space.
That's…”
Dec 19, 2023 negative
Dec 19, 2023 negative
Dec 19, 2023
Dec 19, 2023 negative
Dec 26, 2023
Walling: Fast-moving SaaS companies must evaluate pricing annually to avoid falling behind
“Fast moving space like yours, I do think that if you're not at pretty seriously considering changing your prices raising them or tweaking value metric about every year, I think you're gonna fall behind a little bit.”
Dec 26, 2023
Walling: Portfolio founders almost never have to roll back price increases
“I cannot remember, I've had people raise prices and need to change the, oh, we got the value metric wrong, or like we need to tweak We need to do some stuff, but to raise prices and then truly roll back, I don't know that I remember a time when that's happened”
Dec 26, 2023 positive
Walling: Shipping a fast MVP is an effective form of product validation
“If I can just ship, that's actually a pretty quick way to validate. You know, maybe I'd have one conversation, or maybe I'd do a little less, but it's not like, if I have to go six months, I need to know that there's going to be some type of traction for this.”
Dec 26, 2023 positive
Walling: Validate 'scratch your own itch' ideas with 10 potential users
“If someone comes to me with a scratch your own itch, I usually say, great, now find 10 other people who need it, you know, do some validation. It's not a hard and fast rule, but it gives you a little more certainty that it might Be actually valuable.”
Jan 2, 2024 bullish
Jan 2, 2024
Rob Walling: Founders who dislike their jobs have only themselves to blame
“If you don't like your job, It's no one else's fault because you're your own boss. Like, you run the company. If you don't love running your company, then change it. Figure out how to make it sustainable. Figure out how to make it enjoyable for you.”
Jan 2, 2024
Jan 2, 2024 positive
Rob Walling's 'The SaaS Playbook' sold over 10,000 copies by late 2023
“Between publishing the SAS Playbook and doing the Kickstarter for that in May, sold about
I think just under 3000 copies there, and just last month passed 10,000 total copies sold of that book.
And to put that into perspective, it's a self-published book, St…”
Jan 9, 2024 negative
Walling: Translating a SaaS product at growth plateaus is procrastination
“In, in the SAS playbook, I talk about people who they hit their ceiling of eight K a month, and then they're like, I'm going to translate this into Spanish, German, French, and other things. And I'm always like, that's not, unless your market is tiny, tiny, th…”
Jan 9, 2024 negative
Walling: Founders should not expect charity partnerships to drive paying customers
“Anything, any marketing or any value you get out of it to me is, I think, is a bonus. But I wouldn't have high hopes for something like this. Of like, oh, I'm going to sell a bunch of pieces of software because I think you might be let down.”
Jan 9, 2024 neutral
Walling: Capitalizing on competitor shutdowns requires an already-launched product
“If they've said they're going to shut down and people know this, usually you want to already be there, like today or last month. It's like, oh, my product is a perfect placement for it. But if you're talking about spending a month or two To develop, and then t…”
Jan 16, 2024 positive
Jan 16, 2024 neutral
Jan 16, 2024 negative
Walling: Big tech pedigree is among the least important hiring metrics
“Where I get on an interview with anybody, developer, designer, support person, and I'm looking at their resume saying, oh, they worked at Google. They worked at Facebook. They must be really good at that. No, don't do that. Or they had, they were there for sev…”
Feb 6, 2024 positive
Walling: Podcasters must project energy one notch above normal conversation
“Somehow, when you do that and talk naturally, you sound subdued and with low energy. It's just this weird thing that cameras and microphones do, and so I now, at this point, I naturally switch. When I'm in front of a microphone, I talk just a little bit differ…”
Feb 6, 2024
Feb 6, 2024
Walling: Hide vertical-specific SaaS features behind user account flags
“If you have features that people request and you're like, boy, only one vertical uses this, or even this whole screen or this whole section, you can just, you can build versions of your application that just
Hide a bunch of stuff from certain people, or only …”
Feb 6, 2024
Feb 6, 2024 negative
Walling: Video knowledge bases accumulate costly documentation debt over time
“In the early days, getting a Loom or equivalent recorded for your support or for your KB is way faster to do. Over time, it is essentially a type of debt, video debt, documentation debt, because we did that with Drip in the early days, right? Instead of writin…”
Feb 6, 2024
Walling: Drip built RSS-to-email at $20k-$30k MRR to rescue lost deals
“We were literally losing deals over just that, and they were significant deals, they were hundreds of dollars a month, obviously thousands of dollars in ACV, at a time when we were, I think we built it when we were a 20 to 30 K MRR,
And I knew that there were…”
Feb 13, 2024 negative
Rob Walling says treating a startup like a baby creates unhealthy attachment
“Starting a software company and then being that attached to it, I think is, see the talk from Dr. Sherri Walling a few years ago where she talks about how founders look at their logo and it stimulates the same part of their brain as when they look at pictures …”
Feb 13, 2024
Feb 13, 2024 neutral
Feb 13, 2024
Founders should invest one to two years building SEO before product launch
“In most cases, you're going to put a year or two in just to get enough SEO rankings that when you launch your electronic signature or .NET invoice app, it wouldn't have taken two years to do that. But when you launch that app, you have looked ahead and you've …”
Feb 13, 2024 positive
Rob Walling's $20,000 WP Engine angel check is his third-best asset
“When I scraped together, you know, a couple, 20 grand, I think, which was an enormous amount of money for me at the time. To write Jason Cohen a check, and I was honored to be part of it, and it paid out a tremendous, tremendous payout for me, and it's probabl…”
Feb 27, 2024
Walling: SaaS is valued on profit under $1.5M ARR, revenue above
“The way it works is net profit up to about a million and a half ARR. And above that, if you're dealing with the right buyers, so it'd be strategics or The big, bigger private equity who are not value buyers, they're gonna look at you at a revenue multiple base…”
Feb 27, 2024
Walling: Out of thousands of companies, only two needed price cuts
“In my decades of doing this and then advising and investing, I can think of definitely two companies. I mean, I'm talking thousands and thousands that I've seen and that I've advised to raise prices and all that. I think two for sure that I can think of by nam…”
Feb 27, 2024 positive
Walling: Unvested co-founder equity makes startups unbackable
“Number one is everyone vests, even founders. So if you start a company with one other co-founder, both of you should vest into your equity. That just means that you have to work there for years in order to receive 100% of your equity grant. Usually it's a four…”
Feb 27, 2024 positive
Feb 27, 2024 negative
Walling: Indie and bootstrapped founders should sell only 10% to 15% per round
“Number two is, that's a loose rule of thumb, but like, don't sell more than 10 or 20% of your company in a single round... Loose rule of thumb, even tight rule of thumb is, I would be super suspect if I was selling more than, if you're doing a bootstrapper fun…”
Feb 27, 2024 bearish
Walling: TinySeed views sub-80% founder ownership as a negative signal
“We have seen companies apply to TinySeed that we wanted to fund, and if the founders, by the time they reach us between the one, two, or three of them, however many there are, if they own less than 80% of their company, We start to ask questions, and if they o…”
Mar 5, 2024 positive
Walling: Vertical software founders do not need to be top-tier marketers
“We really like, I really like vertical software. We do at TinySeed because it's, you can dominate it. You're not competing with whoever, Microsoft, Google, Facebook. You don't have to be the best marketer. You just have to be better than the other, like five i…”
Mar 5, 2024
Walling: Product-market fit is a continuum across different customer profiles
“Product market fit is not a binary, it's not a one or a zero, it is a continuum. Product market fit also, per my conversation with Ruben a few weeks ago, you can have, like, strong product market fit with a certain group, or with a certain product, and then yo…”
Mar 5, 2024 negative
Walling: YouTube subscribers are vanity metrics compared to email and podcast audiences
“Sure, because these numbers, this is the thing with vanity metrics, and I'm gonna say YouTube subscribers are vanity metrics, more so, like, email subscribers are, like, not vanity metrics, right? Unless you're, if your open rate's really low, whatever, certai…”
Mar 12, 2024
Walling: Vague landing pages enable better customer discovery than detailed screenshots
“If you give them screenshots and show them how you're doing it, you are putting your opinion on that. At this point, it's not customer development. So I think that's part of the question. It's like the more vague you are, the more customer development you can …”
Mar 12, 2024 positive
Mar 12, 2024
Mar 12, 2024 neutral
Mar 12, 2024 negative
Mar 19, 2024 negative
Walling: Building an audience prior to launching SaaS is not worth it
“I often say, look, if you have an audience, great. That is a great advantage. But if you don't go build one for SaaS. You know, if you're going to do info products or courses or books, of course, but for SaaS, I think it's more trouble than it's worth, and the…”
Mar 26, 2024 negative
Mar 26, 2024 neutral
Walling: 90% of tech companies should bootstrap and only 1% raise VC
“That's where I think about one percent of tech companies should consider raising venture, about nine percent should consider raising some type of funding, whether it's angel, tiny seed, indie funding, whatever, and then about 90% should just bootstrap.”
Mar 26, 2024 negative
Walling: Online creators fail to credit established startup frameworks weekly
“Not a week goes by, literally not a week, sometimes it's more than that, that I don't see someone on Twitter, or YouTube, Reddit, Hacker News, claiming a concept, or even not claiming it, but not crediting a concept that's pretty well-defined, that either I in…”
Apr 2, 2024 positive
Walling: Exiting a startup accelerates future profits under capital gains rates
“Lifestyle businesses in the short term, of course, you're making income net profit on it. It's taxed at income tax rates. And if you exit a startup, right, usually depending on where you live, you get that long-term cap gains and you accelerate, you know, you …”
Apr 2, 2024
Apr 9, 2024 negative
Apr 9, 2024 negative
Walling: Zero-to-one marketing talent is far rarer than strong engineering talent
“It feels like the harder thing is to be really good at marketing, or really good at sales. I'm not saying being a really good developer is not hard, but I just feel like I know a lot more really good developers, and I know a lot of, like, pretty good product p…”
Apr 9, 2024
Walling: Technical founders must learn marketing basics to evaluate hires
“As a developer, I would learn enough marketing to be dangerous. And look, even if you don't do it all yourself, you learn the frameworks, and therefore you can evaluate marketers that you hire. Because much like there are a bunch of developers you can hire who…”
Apr 9, 2024
Walling: Every TinySeed company over $1M ARR had founder-led marketing
“When I look at the list, I have this list I keep of A&R and I keep of all the tiny seed companies that are over a million in ARR. And it's a, you know, it's a pretty long list, which is great. I believe without fail, every single one of them, the founder or on…”
Apr 9, 2024 neutral
Apr 16, 2024
Rob Walling sold seven figures of crypto while maintaining a position
“In the subsequent years, we have definitely sold, you know, seven figures, obviously playing with house money plus plus, taking chips off the table, but still have enough that if it continues to go up, that we ride that wave as well.”
Apr 16, 2024 positive
Apr 16, 2024 positive
Apr 16, 2024 positive
Apr 16, 2024
Rob Walling ranks the seven investments that built his wealth
“So to recap, seven ways that Sherry and I made life-changing wealth in our life. Number one is selling companies. Number two is investing in crypto. It sounds so weird to say. Number three, running profitable companies. Four, angel investing. Five, salaried em…”
Apr 16, 2024 negative
Apr 16, 2024
Apr 16, 2024 positive
Apr 16, 2024 neutral
Apr 16, 2024 neutral
Apr 23, 2024 negative
Walling: Bootstrapping in VC-heavy markets stacks odds against founders
“A big mistake I see folks making is thinking I can build a venture scale business, or I can build a business that will probably need a lot of funding, but I can just bootstrap it. Or I can build in a market where there's going to be a ton of funding and probab…”
Apr 23, 2024
Walling: Drip was the 300th email app against heavily funded competitors
“Drip was, what, the 300th email marketing application, and our competitors who, like, I think VentureBeat did a top 10 Marketing automation providers, maybe it was like top 15, and we were number, I honestly forget the number, like 10 or 11, and everyone ahead…”
Apr 23, 2024 bullish
Apr 23, 2024
Walling ran six-figure software products without an LLC from 2002 to 2007
“I didn't have an LLC for the first five years of, I had all these products. I had, this was from O two to O seven, 2007. I was a freelancer, I was a contractor, and I was making money from software products, six figures from all this stuff. And I was still a s…”
Apr 23, 2024 negative
Walling: Passive side-project founders are less likely to succeed
“Now, do I think you're less likely to find success that way? I do. I think that if you're driving day to day, and you have this burning desire to get to some end result, he's right, you are a hamster on speed, but that can be beneficial when you're an entrepre…”
Apr 30, 2024 negative
Apr 30, 2024 positive
Walling: Target LinkedIn for job titles, Facebook for psychographics, Google for intent
“If you want, if you know the job title, you go there. If you know the demographic, psychographics, you go to Facebook. And if you want intent and there is actual volume, then you go to Google if you have any money to spend.”
Apr 30, 2024 neutral
Apr 30, 2024 neutral
Walling: Dual-Funnel SaaS Generates 70-80% of MRR From Higher-Tier Plans
“Most of, you know, I have insight into a 190 something companies, and most of the companies with this type of dual funnel where you have either free on the bottom end or super cheap, and then you have people paying you 500, a 1002 thousand and up, they make th…”
Apr 30, 2024 neutral
Apr 30, 2024 neutral
Apr 30, 2024 neutral
May 7, 2024 neutral
Walling: Early-Stage Startup Ideation Has No Blueprint, Only a Compass
“The challenge is you can't be as prescriptive because there is no blueprint for this early stage ideation stuff. There is kind of a blueprint. The SaaS playbook is pretty prescriptive about a lot of things because I do think there are best practices, rules of …”
May 7, 2024
May 7, 2024 positive
May 14, 2024
May 14, 2024 positive
May 21, 2024
Walling: HIPAA-compliant SaaS products must charge premium pricing
“The thing to think about is if you're HIPAA compliant, you need to charge a lot of money for this. Like I've seen SaaS startups that are charging, you know, let's make up some numbers. 20 dollar for the cheapest plan, then a 50 and then a hundred dollar plan. …”
May 21, 2024
Walling: Acquiring a tiny competitor rarely justifies the operational overhead
“So if you're gonna acquire a competitor doing a couple thousand dollars a month, I really question if it's worth it. Even if, let's say it was free, and the competitor's gonna shut down, and they literally were to say, I'm just gonna give you all the assets of…”
May 21, 2024 negative
May 21, 2024 positive
Walling: Bootstrappers can achieve HIPAA compliance on a tight budget
“HIPAA compliance is not out of the realm of bootstrappers. Now, if you want SOC II compliance, that becomes pretty pricey, pretty quick. HIPAA compliance is different. And of course, this is not legal nor HIPAA advice that I'm giving you, but I have known many…”
May 21, 2024 neutral
May 21, 2024 negative
Walling: Avoid starting a bootstrapped SaaS without a technical co-founder
“Maybe it's like an 80% don't do is don't start a SaaS without a technical co-founder. And the reason that I say that is Most of the companies that I see, the bootstrapped and mostly bootstrap companies... The vast majority of folks I see trying to do this with…”
May 21, 2024 negative
Walling: Bootstrappers should measure Total Reachable Market instead of TAM
“TAM, total addressable market, is top down. It's coming from the MBA at Harvard saying, well, we could capture 30, 50, 80% of an entire market and then it's worth decabillion dollars. That's top down. When you are bootstrapping or mostly bootstrapping, I think…”
May 21, 2024 positive
Jun 4, 2024 neutral
Walling Grew Classic ASP App HitTail to $30,000 Per Month in 2011
“I purchased an app called Hit Tail. It was a SaaS app, SEO long tail keyword tool, and that's the one that I grew into the lifestyle business. It was pretty life-changing in terms of making 30 grand a month, more money than we'd ever had or ever seen. And that…”
Jun 4, 2024
Jun 4, 2024 neutral
Jun 4, 2024 neutral
Startups Cannot Afford to Defend Even Legal and Honest Comparison Pages
“If you're being honest and truthful and forthright in your marketing, if you have a comparison page that It really does compare the two, honestly. Yeah, they don't really have a leg to stand on if you're doing that, but if they send you a C and D and they're a…”
Jun 4, 2024 positive
Startups Should Name Well-Known Incumbent Competitors Directly in Positioning
“All things being equal, I would lean towards naming them, if you want to know the truth. But you do have to weigh the pros and cons of potential liability, which again, I think is low, but it's not legal advice. But I found the more specific you can be about p…”
Jun 4, 2024 negative
$15 Per Month SaaS Pricing Drives High Churn and Prevents Paid Marketing
“15 dollars a month is rough though. That is going to be, you're going to have some pretty high churn. You can't afford to market at 15 bucks a month. You can't afford to do ads. You can't afford to do anything except for free things. So it's, you can't afford …”
Jun 4, 2024
Jun 11, 2024
Jun 11, 2024
Walling: Only tens of software markets globally can support mass freemium
“For you to have 300,000 free users, There are tens of millions of users worldwide, right? If not hundreds of millions, and like how many, there's a rhetorical question, but how many software markets have that many users? There's probably electronic signature t…”
Jun 11, 2024 bullish
Jun 18, 2024 positive
Jun 25, 2024 negative
Jun 25, 2024 negative
Jun 25, 2024 neutral
Jun 25, 2024 positive
Walling: High-Touch SaaS Models Have an Advantage When Testing Price Increases
“I would actually say you have an advantage if you are doing high touch, if you're doing demos, and that allows you to have conversations with people and also allows you double the price. You quote it to them, and they say, wow, that's out of our budget, and yo…”
Jun 25, 2024
Walling: Almost No SaaS Companies Run True Pricing A/B Split Tests
“And I have only known of one SaaS company that ever tested prices. Everyone else just does not have the volume. And frankly, it is so much work to do this well. So there's, I mean, it's truly just split testing, like having people click and the price appear di…”
Jul 2, 2024 negative
Walling: Working 12- to 14-Hour Days Led to Wasting Half His Time
“Grinding it out and working 12, 14 hour days, which again, I did as both a contractor and then doing products for a while back when I had time, no kids, all this stuff. I worked on a lot of the wrong things. I wasted so much time. I mean, probably half my time…”
Jul 2, 2024
Jul 2, 2024 negative
Walling: Building an Audience Is an Inefficient Way to Grow SaaS
“Same, same thing with, oh, you should build an audience in order to build your, it's like, oh, that's a real long way to do it. I built an audience. I built multiple audiences over You know, several years, and it's, you know, 15 years or whatever, and it's way…”
Jul 2, 2024
Jul 2, 2024
Jul 2, 2024
Jul 2, 2024
Jul 9, 2024 neutral
Jul 9, 2024
Walling: Upfront credit card requirements for SaaS trials fell to 71%
“And the findings are that the asking for a credit card upfront has increased and then decreased again. So the first year it was 73%, asked for credit card upfront, then it went up to 78%. 78% in the next one, and it's down this year to 71%.”
Jul 9, 2024 neutral
Walling: Roughly 85% of bootstrapped SaaS companies have one or two founders
“I forget if it's like 70% of mostly bootstrap SaaS. Are single founders. It's like a huge chunk. And then another like, 15 plus percent is two founder companies. And that's just the most common. I mean, that's like the 85, that's the lion's share, right? 85%.”
Jul 9, 2024 neutral
Jul 9, 2024 negative
Jul 9, 2024 neutral
Walling: SaaS startups raising $250K-$500K transition out of bootstrapped status
“Like, there are venture capitalists who will say, if you've raised less than a million dollars, you are effectively bootstrapped. Like, that's how they view it. And for me, usually the number is in the two 50 to 500 K. I think that's when you start to transiti…”
Jul 16, 2024 positive
Walling: The top three most effective co-founder combinations for startups
“The top three in no particular order. It's kind of all, all tied for one in my head is a developer plus a marketer. Or a developer plus a salesperson, depending on if it's, you know, a higher low touch funnel and developer plus subject matter experts, as long …”
Jul 16, 2024 bullish
Walling: Specialized vertical SaaS maintains pricing power and avoids commoditization
“To charge for a specialized tool, you have pricing power because you're not a commodity, and whether you can charge more or not is one part of the question, but the other one is that you do, in fact, your pricing is not going to zero.”
Jul 16, 2024 bullish
Walling: Word-of-mouth spreads like wildfire in vertical SaaS
“One is that word of mouth in small verticals is like wildfire way more than The examples I always bring about horizontal SaaS are like SignWell and SavvyCal, right? And they, word of mouth can be fine, but it's not wildfire in those spaces, versus GymDesk and …”
Jul 16, 2024 negative
Jul 30, 2024
Walling: MicroConf organizers track non-sponsors who aggressively pitch attendees
“If you do come to MicroConf for another conference and you are not a sponsor and you start selling pretty heavily, it will get back to the organizers and they will remember your name because we have had folks do that.”
Jul 30, 2024 negative
Walling: 'Launch one thing a month' leaves founders clueless when growth plateaus
“And this is my biggest issue, I think, with the whole launch one thing a month and see what sticks, because you are not going to know why you're growing, and so when you plateau, you're not going to know why you plateaued, because you kind of got lucky, becaus…”
Jul 30, 2024 neutral
Walling: At SaaStr, attendees ignore content to focus entirely on pitching
“If you go to Sastr, everyone's there to sell their stuff to everyone else. It just is, everyone's trying to put deals together. Everyone's trying to put meetings together. That is kind of the point of Sastr. A lot of people ignore the content because they're t…”
Aug 6, 2024 negative
Walling: Low-ARR SaaS Founders Should Raise Prices Instead of Going Freemium
“If I were in his shoes, I would do the price increase. And as you said, it comes with positioning. There's a bunch of stuff that comes with that. It's not just as simple as, oh, raise your prices and it fixes it magically, but that would be my own personal lea…”
Aug 6, 2024
Aug 13, 2024 positive
Walling's SaaS Playbook generated $275k in royalties on $400k year-one revenue
“Top line revenue is just under 400,000. And my best estimate is paid to me as quote unquote royalties or a percentage of the purchase is about 275,000. So again, I don't, you know, I haven't thought traditionally of books as being a revenue source, but obvious…”
Aug 13, 2024 negative
Walling: Hiring junior local employees was a major early mistake at Drip
“This is one of the bigger mistakes that I made in the early days of Drip, is I hired really junior people, and it was, you know, I use the excuse that, well, this is all I have money for, and I want people to be local, and really, to be honest, in Fresno, Cali…”
Aug 20, 2024 neutral
Aug 20, 2024 positive
Walling: 85% of Bootstrapped SaaS Companies Find Hiring Same or Easier
“85% of companies we surveyed, so we surveyed 700, almost 700 bootstrap, mostly bootstrap SAS companies, all microconf, tiny seed type companies, 85% reported that the difficulty in hiring people is either the same or easier than last year.”
Aug 20, 2024 neutral
Walling: Jason Fried admits luck and timing drove Basecamp's success
“They can do stuff like not market, like not sell, because they're in a luxurious position and good for them. You know, the luck and timing were one and two. Jason Fried told me that for their success. Unless I can replicate luck and timing, I can't. Then I nee…”
Aug 20, 2024 neutral
Walling's 3 SaaS phases: Product ($0–10K), Business ($10K–50K), Company ($50K+)
“I talk about it in three phases and there are more than this, but like the first phase is building a product. Second phase is building a business. Third phase is building a company. And usually I think of product as being zero up to Usually about 10 K, MRR, to…”
Aug 27, 2024
Aug 27, 2024 neutral
Walling: Every software company founder eventually sells their business
“Everyone sells, like I say this, everyone sells eventually. I never thought MailChimp would sell and they eventually sold, you know, I mean, really, I had all these examples and they've all sold except for I think Basecamp is probably the one that I think abou…”
Sep 3, 2024 neutral
Only 15-20% of TinySeed Founders Prefer Long-Term Dividends Over Exits
“With my show of hands surveys that I've done in several tiny seed Zooms, it appears that it's about 15%, maybe 20, that want to grow a company for the long term and take out profits. So it is the, you know, call it the super majority that do want to have that …”
Sep 3, 2024 negative
Sep 10, 2024 neutral
Sep 10, 2024 positive
Rob Walling: Repeat SaaS Founder Success Proves Early Validation Is Learnable
“I'm going to point to Jason Cohen. I'm going to point to Heaton Shaw. I'm going to point to David Cancel. I'm going to point to myself. I'm going to point to Ruben Gomez. I'm going to put, you know, how many like two, three, four times successful founders? The…”
Sep 10, 2024
Sep 10, 2024 negative
Sep 10, 2024
Sep 10, 2024 negative
Sep 10, 2024
Rob Walling: MicroConf Has Spent $750,000 Producing Free Content
“We have spent north of half a million dollars producing free content. And that's YouTube. That's this podcast. Oh, I mean, if I include, actually, if I include this podcast, it's literally, it's gotta be 707 or 50 grand, you know, over the course of the years.”
Sep 17, 2024 positive
Sep 17, 2024 negative
Walling: Quarterly planning harms startups until reaching multi-million scale
“Part of our biggest strength is that we are so nimble and can move so quickly, and frankly, 90 days in the life of a startup is like a year in the life of a big company. So trying to think, I don't know, I'm going to be responding to customer inquiries and thi…”
Sep 17, 2024
Sep 17, 2024 positive
Walling: Five co-marketing partners are worth 10x more than 10k Twitter followers
“This is why I say build your network, not your audience, because that network is so much more valuable than 10,000 people on, on x Twitter following you. Having five people that you can integrate with or co-promote or get in front of their audience is worth fi…”
Oct 1, 2024 positive
Startup success relies on asymmetric upside from rare wins
“80 or 90% of things I do don't work, but the ones that do have asymmetric upside, and they push the business forward, and they push my life forward, and they work. And that's the pattern that I see with successful entrepreneurs, and frankly, someone who's succ…”
Oct 1, 2024 negative
MicroConf discontinued local events due to financial losses and burnout
“We launched local events... The local interest wasn't there. We couldn't charge enough, even to make them break even. We were losing money on them. And it was burning me and the producer out, because we were on the road all the time.”
Oct 1, 2024 neutral
Oct 1, 2024 positive
Oct 1, 2024 negative
Oct 1, 2024 negative
For technical founders, writing code often masquerades as productivity
“Here's another distraction that I see masquerading as productivity in our circles of entrepreneurs. It's launching another product without marketing the one you've already launched. Or how about this? It's focusing on writing more code, or answering support ti…”
Oct 8, 2024 neutral
Walling: Early bootstrappers learned SEO and split testing from info marketers
“There were no books about startups doing this. It was all the info marketer, internet marketing stuff. And so I went and learned copywriting from them and applied it to startups... So they were doing split testing. They were doing AdWords. They were doing SEO.…”
Oct 22, 2024 positive
Oct 22, 2024 positive
Walling: Hire specialists for ad channels to diagnose fit versus execution error
“If you try to learn it and you try LinkedIn ads and they don't work, you don't know if you're not good at them or if they don't work for your business or your customer type. But if you hire someone who you think is pretty good and you get references and you pa…”
Oct 22, 2024 neutral
Oct 29, 2024 bearish
Oct 29, 2024
Rob Walling: There are only about 20 B2B SaaS marketing approaches
“There are only 20 B to B SaaS marketing approaches. That's it. Because otherwise you think there are thousands, and it's just like, no, here's the list. Pick one. Now maybe I missed one. Maybe there's 21, but it's pretty much all of them.”
Oct 29, 2024 positive
Oct 29, 2024 positive
Oct 29, 2024 positive
Rob Walling: Tim Vander Castile bootstrapped to $35M ARR and $300M exit
“And he's like, yeah, and then we got our ARR to thirty-five million, and I was like, whoa, and they bootstrapped, and I was like, that's a thing, and they said, then we sold four, and there was an asterisk, it was like, according to public records, because I a…”
Nov 5, 2024 negative
Walling: Distributing over 50% of profits to employees threatens company viability
“I believe there was someone who was giving away more than 50% of their profits to their employees, and that, it makes your business, ah, I'll say almost inviolable. It's just, if you ever go to sell, like, it's just not a great way to structure profit sharing.…”
Nov 5, 2024 negative
Nov 5, 2024 positive
Walling: Structure profit-sharing as a pooled percentage rather than individual allocations
“Consider structuring profit sharing as a pool rather than a committed percentage to an individual. For example, instead of telling early employees they get one, two, or three percent of profits, have all key employees share in a 10 or 15% profit sharing pool.”
Nov 5, 2024 neutral
Nov 12, 2024
Nov 26, 2024
Nov 26, 2024 positive
Walling: Drip strictly used product-led self-serve for sub-$100 monthly plans
“What we noticed was on the lower end, you know, if someone was going to pay us 50 dollars a month or a hundred dollars a month, those are our cheapest plans. It had to be product led. I was not, we weren't going to do a demo. We were, you know, there's just th…”
Dec 3, 2024
Walling: Struggling with motivation means you do not actually want entrepreneurship
“I get emails to this podcast about, you know, I have a good day job, and I'm making good money, but I really want to be an entrepreneur, but I just have a tough time getting motivated. And I think to myself, then you don't really want to be an entrepreneur.”
Dec 3, 2024
Dec 10, 2024 neutral
Founders who ignore exit planning get blindsided within 10 years
“Entrepreneurs who have never thought about it usually find themselves blindsided three, five, or 10 years into a business when life circumstances change. They get tired of the business, or they get an offer with a shocking number of zeros.”
Dec 10, 2024 positive
Dec 10, 2024 negative
Dec 17, 2024 bullish
Dec 17, 2024 positive
Walling supports government regulations restricting children's access to social media
“I overall am probably just fine with governments limiting Children's use of social media. I do think it should be the responsibility of the parents, but I just know so many parents that don't. So it must be like, let's say there was no drinking age minimum, an…”
Dec 24, 2024 positive
Walling: The SaaS Playbook Sold 30,000 Copies in About a Year
“Start Small, Stay Small has been around for, 14 years, and sold about, my best approximation is 30,000 copies, and the SAS Playbook hit 30,000 copies in about a year, and it still continues to sell. I haven't run the numbers in a few months, but it's gotta be …”
Dec 24, 2024 neutral
Jan 7, 2025
Jan 14, 2025 neutral
Walling: VC funds adopted content marketing to escape commodity status
“That was a big thing, was for them to start, A, generating deal flow, but B, to get the trust, I think, from people so they weren't a commodity, because they were a commodity before. It's kind of like, if I'm gonna go borrow money for my house, who's gonna giv…”
Jan 14, 2025 negative
Rob Walling: AngelList investments either went to zero or barely broke even
“The valuations for, like, almost no revenue were, like, ten million, and I did put, I put, like, five grand into one of those, and I put 10 grand into another, and all of them either went to zero or returned, one returned me 11 grand for my 10 grand investment…”
Jan 21, 2025 negative
Jan 21, 2025 bullish
Walling: MicroConf pivoted to LinkedIn after YouTube growth plateaued at 90,000 subscribers
“We pick one new thing to attack, and we did YouTube for two and a half years, and then, you know, until it plateaued around 90,000, and then we are looking at LinkedIn next, and we're going all in. Like, we hired a LinkedIn consultant. We are spending thousand…”
Jan 23, 2025 positive
Jan 23, 2025
Walling: Introverted developers will not voice grievances without scheduled one-on-ones
“And I realized, oh, no one's gonna just come and tell me when there's a grievance, or when they feel bad. They don't, they're not gonna initiate. There's a lot, especially, you know, introverted developers don't wanna rock the boat, don't wanna whatever, for w…”
Jan 23, 2025
Walling: 50% customer consensus is enough to validate a product pivot
“If you're saying nine out of 10, that's an incredible win, because I've seen folks try to do a, like, a pivot like this, or an expansion, or whatever, and maybe it's five out of 10, and it's still the right call. You know, because the other five want five diff…”
Jan 28, 2025 positive
Jan 30, 2025
Walling: Startups often implode at $500k ARR over lifestyle vs VC misalignment
“I have seen multiple companies implode because of this exact dynamic. They get to half a million a year, for example, and one founder wants super profitable lifestyle business, and the other one's like, I want to raise a series A and go to fifty million or, yo…”
Feb 4, 2025 bearish
Feb 4, 2025 bearish
Feb 4, 2025
Code is only 10% to 20% of spinning out a new product
“People think that spinning something out into its own thing is, well, the code, it's easy to spin, the guy just forked the code, and it's a, or even I just point to the same repo, and that is, I don't know, maybe 10% of the effort? It's 20% of the effort? It's…”
Feb 4, 2025 bearish
Feb 6, 2025 positive
Feb 6, 2025
Walling: Switching to a completely unrelated product domain is not a pivot
“You know, sometimes people will say, I was going to build project management for hair salons, and now I'm going to pivot into building in a mobile app on Facebook. And it's like, that's not a pivot. That's just a completely different thing.”
Feb 18, 2025 bearish
Feb 18, 2025 negative
Feb 18, 2025 bearish
Feb 18, 2025 neutral
Feb 20, 2025 negative
Walling: Launching MVPs to an audience creates false demand and burns goodwill
“I call that false demand the curse of the audience. And if there's two curses to it, one, you tweet it out or you email your list and everyone's like, oh, I kind of want to check out what they're doing and everybody's really interested. And then they're not ac…”
Feb 25, 2025
Feb 25, 2025 positive
Feb 25, 2025
Feb 27, 2025 neutral
Mar 4, 2025
Mar 4, 2025
Mar 6, 2025
Walling: Scaling $20k MRR SaaS is blueprintable, but pre-PMF is not
“If you were to come and be like, Hey, I'm at 20 KMR and I have 20 customers or 30 cut, whatever. And I can be like, oh, great. Let's, I can playbook the out of this. You know, I know the next steps. I can almost blueprint this out of exactly what I would do in…”
Mar 13, 2025 neutral
Walling: No failed startup founder ever regrets moving or shipping too fast
“When I've asked other founders when they're, after their business has shut down, you know, what are things that you regret or that you would do differently? I've never once heard them say, I would have executed more. So we moved too fast. We shipped too many t…”
Mar 25, 2025 positive
Mar 25, 2025 positive
Mar 25, 2025 neutral
Walling: Affiliate Programs Scale SaaS via Infomarketers but Fail with SaaS Founders
“If you have a bunch of infomarketers or bloggers using your tool, and you set up an affiliate program, and they like your tool, and you pay them 20 or 30% top line, they will likely get you hundreds or thousands of customers. Like, if you work hard at this, an…”
Mar 25, 2025
Apr 1, 2025 positive
Apr 1, 2025 positive
Apr 1, 2025 negative
Walling: SaaS products must never offer unlimited tiers on their core metric
“There's some rare instances where you can offer unlimited something but not your value metric, right? If you're measuring based on the number of email subscribers, there is no unlimited email subscriber plan with MailChimp or if I was starting an email service…”
Apr 1, 2025 negative
Walling: Affiliate marketing is enterprise sales and won't fix acquisition issues
“Don't think affiliation or affiliate marketing will fix your acquisition issues. It'll just create another acquisition problem. Acquiring affiliate partners. 100% true. And I don't know if Pierre found this on his own, or I've been saying this for 1012 years, …”
Apr 1, 2025 negative
Apr 1, 2025
Apr 1, 2025 bullish
Apr 1, 2025
Walling: SaaS startups should only rebrand after reaching $20,000 in MRR
“When does it make sense to rebrand? And usually, that's further down the line. It's if you basically get an MVP brand out, and you're doing 20 or 30 K a month, or your brand is hurting your efforts. It's not helping you close sales, it's actually driving prosp…”
Apr 1, 2025 positive
Apr 1, 2025 negative
Walling: Multi-million ARR SaaS businesses face danger relying on single channels
“The only time I think you get in trouble with this is when you're, you have a multi-million dollar company, two, three, four million dollars of ARR, and you're still relying on a single channel, that's when it makes me nervous. Because even if it's SEO, which …”
Apr 1, 2025 negative
Apr 1, 2025 positive
Walling: Growing SaaS above $1.5M ARR usually exits over 5x ARR
“And then if you get to about a million and a half, two million ARR, and you're growing, and you're selling not just the technology, but kind of the team, like the whole company, the product, everything you've built, that's more than two to five X ARR, usually.”
Apr 8, 2025 positive
Walling: Shifting B2B SaaS marketing focus from YouTube to LinkedIn
“We have switched our focus from YouTube. I'm still putting out a video every other week, so it's still a lot of effort, and a lot of content, and we're still having success there, but we kind of have tapped out the audience, if I'm being honest, of what we foc…”
Apr 8, 2025 neutral
Apr 8, 2025 positive
Apr 8, 2025 neutral
Apr 8, 2025 positive
Apr 15, 2025 negative
Walling: Sharing revenue in public is mostly bragging, marketing, or fake
“I've bristled at this whole sharing revenue in public thing anyways, because I think it's not building in public, it's a lot of bragging in public, and I really do feel like a lot of sharing revenue, it's either marketing, or bragging, or a lot of it's fake, a…”
Apr 22, 2025 neutral
Apr 22, 2025 negative
Apr 22, 2025 positive
Rob Walling: MicroConf spent $15K/month on YouTube, growing to 90K subscribers
“You know, you saw when we were dropping 15 grand a month on YouTube, and it worked. It was a lot of money, but it works for us, you know. And then now we're spending a lot of time and money on LinkedIn. Why? Because we have that ability to take a flyer. And if…”
Apr 22, 2025
Walling: Companies need written culture rules once reaching 15 to 20 people
“I think there's a point between 15 and 20 where if we are not communicating that, if we have If the people at the top, let's say Anar and myself and, you know, Tracy and Alex on the accelerator side, if we are not directly doing the hiring and training, and it…”
Apr 29, 2025 negative
Walling: Founders must rely on intuition over data until eight figures
“Being a founder is making hard decisions with incomplete information. And people who think they can get all the data and a hundred percent data driven, that's bull, you know, and even data can be twisted, even at big companies where they have a lot of data. It…”
May 13, 2025 neutral
May 13, 2025 neutral
Walling: Raising prices merely fixes underpricing, unlike actually moving upmarket
“There's a difference between raising your prices and going up market. Those are two different things. They can be the same, but a lot of times you are just underpriced for the market. You're charging 29, you can charge 49 to the exact same customer base, same …”
May 20, 2025 bearish
Walling: Pure Marketing-Driven SaaS Rarely Reaches Multi-Million Dollar Scale
“Sometimes, if you have a low touch, no touch funnel, you don't have sales at all. You don't do any outbound, and you don't do demos, and so it's purely a marketing driven SaaS. And that is kind of the, you know, the bootstrapper indie hacker dream. It's pretty…”
May 20, 2025 bearish
Walling: UX quality matters far less for B2B SaaS than founders believe
“Probably most software? Doesn't matter. If I think of most B to B SaaS software, I shouldn't say doesn't matter at all, because you can have catastrophic US and then every UX and then everyone hates it, but it doesn't matter nearly as much as I think.”
May 20, 2025 bearish
May 20, 2025 neutral
Walling: Only one out of 204 TinySeed startups ran physical on-prem servers
“Of all the tiny C companies, 204 investments we've done, there was one founder who had physical servers, and the reason was, is it was like three years ago, and he was doing AI and needed physical GPUs, because it was way too, he built his own model.”
Jun 3, 2025 negative
Walling: Working a 10-hour week left him bored without purpose
“So there was a time in my life, it was back when my second son was born, and I found freedom. I was working a 10 hour work week, literally. I had a bunch of products. It was the four hour work week, but I was working 10 hours. It was amazing. I was free. I hun…”
Jun 10, 2025 neutral
Jun 10, 2025 positive
Walling: Price pilots so you have no regret if enterprise deals stall
“I want to feel okay about the pricing. Like, if this is the only work I ever do for them, And they basically say, you know what, we don't have the budget, or it didn't work, or leadership change, or whatever else happens, they go out of business. I don't parti…”
Jun 10, 2025 positive
Walling: HitTail generated $1M in total returns on a $31K acquisition
“I made a million dollars from Hittail. I spent 31,000 dollars on that thing, and all the revenue plus the exit sale price was a million dollars. It completely changed our life. That was, it had like a 90% net profit margin too, because it was just me with a co…”
Jun 10, 2025 negative
Walling: Founders must charge for pilots because customers undervalue free work
“I'm a believer, for sure, that you should be charging for them because, as opposed to just comping it, which is not anything that you indicated, some founders are so desperate to get the business that they want to try to give it away, and there's so many probl…”
Jun 17, 2025 positive
Walling: SaaS founders can start delegating marketing or sales at $1M-$2M ARR
“I do think that when you get to about a million or two, it depends on a bunch of stuff, the type of business and all this stuff. I think this is when a founder can think about handing off one of those three. Marketing, sales, or product. Now, it's not delegati…”
Jun 17, 2025 positive
Jun 17, 2025 negative
Walling: Founders must avoid B2C, marketplaces, and marketing comfort zones
“Stop doing B to C. Stop doing two-sided marketplaces and stop staying in your comfort zone when it comes to marketing and sales. Your customers don't care. Your customers don't care what you're comfortable with. They care how with how they buy and how they wan…”
Jun 17, 2025
Walling: 90% to 95% of SaaS Plateaus Aren't Caused by Tapped-Out Markets
“In most cases, and this is again, 90, 90, 95% plus of plateaus that I see, or have nothing to do with market size, or I've tapped out a market. It's really a one in 51 in a hundred, where it's like, oh no, we really have tapped out the market, and you actually…”
Jun 24, 2025 neutral
Jun 24, 2025 neutral
Jun 24, 2025
Walling: Foreseeing a Growth Plateau Prompted the Drip Sale
“One of the reasons that we sold was I was like, how far can we take this before we plateau? I don't know. I mean, I could do some math on it, but it, and I saw that, and then I was like, how are we going to get past that plateau that is coming? It wasn't month…”
Jun 24, 2025
Walling: Flat $2M ARR SaaS Commands Only 1x to 2x Multiples
“If you are doing, let's say, two million bucks a year, and you're going at 40, 50, or more percent per year, if you do not have that, let's say you're flat, let's say you're at two million, and you are, you've grown less, you know, less than 10% say in the las…”
Jul 1, 2025 negative
Jul 1, 2025
Jul 1, 2025 positive
Jul 1, 2025 neutral
Walling: Never regretted selling Drip, but regrets operating under chronic anxiety
“People have asked me, like, do you ever regret selling drip? And I've never had a day where I regretted, but I do regret the way that I operated during those years, and the way I let my own mental health deteriorate”
Jul 1, 2025
Walling: Founders should only accept feedback from qualified, trusted sources
“The solution is not to listen to no one. It's to listen to people who you trust to give you honest feedback that comes from a genuine place, but also qualified feedback. So it's folks in your mastermind, if they are ahead of you, or you believe that they're sm…”
Jul 1, 2025 negative
Walling: Hiring only task-level thinkers turns founders into project management bottlenecks
“Didn't realize that I needed to hire project and owner level thinkers or else I became not only a bottleneck, but a project manager and someone who was basically just managing a bunch of task level thinkers.”
Jul 1, 2025 negative
Walling: Ambitious entrepreneurs will never remain satisfied for long
“You're never going to be happy for very long. This is the curse that we have as entrepreneur. It's a blessing and a curse. It's a blessing because it motivates us To do things, right? To ship, and to grind, and to believe in the growth mindset that we'll get b…”
Jul 1, 2025 bearish
Jul 8, 2025 negative
Jul 8, 2025 neutral
Jul 8, 2025
Jul 8, 2025 negative
Jul 8, 2025
Walling: Over 95% of TinySeed SaaS investments had no launch audience
“95 plus percent of the SaaS companies that I've invested in had no social media audience, no personal brand audience. When they launched, they still don't, and they're still wildly successful, and there's dozens of seven and eight figure SaaS companies in Tiny…”
Jul 8, 2025
Walling reveals his venture bets: $11k DotNetInvoice, $35k HitTail, $200k Drip
“So I bet 11,000 dollars on .NET
Invoice in oh five, oh six,
It was a tremendous bet.
It was a money I had just painstakingly worked hard to save nights and weekends.
Then I bet 30,035 thousand maybe with legal fees on Hittail in 2011.
I bet 200,000 dollars bui…”
Jul 15, 2025 negative
Jul 15, 2025 neutral
Walling: TinySeed sees quarterly cease-and-desists and co-founder implosions across its portfolio
“204 investments, I think, just through TinySeed. We see a cease and desist at least once a quarter, sometimes every two months, just because it's a lot of large numbers. Now we also see co-founders implode about once a quarter and we see, you know, an app get …”
Jul 22, 2025 bearish
Jul 22, 2025
Walling: Entrepreneurial wealth comes from exits, not operating profit
“Most of the wealth that I see built in entrepreneurship is not actually from taking profit out of an operating business. Most of it is from exits. It's from selling it, and that's something that a lot of folks I don't think are familiar with.”
Jul 29, 2025 positive
Jul 29, 2025 negative
Rob Walling: 75% to 80% of founders joining TinySeed undercharge or misprice
“Most makers, most developers, and most early-stage founders undercharge for their product, and so that's kind of the rule of thumb that we see, you know, coming into TinySeed, for example, which is something that I've tracked pretty closely. It's like, 75, 80%…”
Jul 29, 2025 positive
Walling: Founders can find competitive features in incumbents' one-star reviews
“You go to Capterra and G two and anyplace else that they're rated and you look at the one star reviews and you think to yourself, oh, they're not building this feature. This is the feature that I can build to potentially compete with them.”
Jul 29, 2025 positive
Walling: Only 1 or 2 TinySeed companies regret raising prices
“In all of the times that I've seen tiny seed companies raise their pricing, because we do encourage them to, and not just blindly, but it's kind of obvious, you know, you kind of get a feel for what something maybe should be charged, or at least the range, and…”
Aug 5, 2025
Rob Walling capped intense startup work seasons at three consecutive months
“Every time that I was doing more work than I wanted to be, it was always like, this is a season, this is not permanent. I don't know if this season is a month, or if it's five months, or six months. I never did it for a year straight like that. I did feel stre…”
Aug 5, 2025
Aug 5, 2025
Rob Walling explicitly called out Infusionsoft and Marketo on Drip's homepage
“Lightweight marketing automation that doesn't suck was the H-one of DREP for years. So what does that imply? That implies, and then I named, because I wrote the whole copy for that long form landing page, I named Crap. Who was it? It was Infusionsoft. It was M…”
Aug 12, 2025
Aug 19, 2025 positive
Aug 19, 2025 negative
Walling: Five-person startups should never hire from 500-person companies
“If I run a five person team, almost without exception, I will not hire someone from a 500 person team. Just won't do it, because retraining that culture, that thinking, that there is no process, you have to do your stuff, is so very hard. And so, again, I say …”
Aug 19, 2025 positive
Walling: Half of TinySeed-funded companies are run by solo founders
“We have funded gobs of single founder companies, and I don't remember the exact number, but it's probably 50%, if I'm guessing, are single founder, and another 35% are two founder, if I were to just ballpark it, so that puts us to 85, maybe even more, maybe it…”
Aug 21, 2025 negative
Aug 21, 2025 neutral
Walling: Accelerators with broad business models lose deep operational granularity
“The moment that you rise up one layer of abstraction, you lose granularity, and two hours on churn makes no sense if there's a biotech company next to you, and a hardware company on the other side, and a two-sided marketplace on the other side, and a B to C co…”
Aug 21, 2025 positive
Aug 21, 2025 neutral
Aug 26, 2025 positive
Walling: Fiscal.ai raised a $10M Series A and grew to 40 employees
“I just talked to Brayden Dennis, who's the founder of Fiscal.ai. And he, it was just him and three co-founders, and now they raised a ten million dollar Series A. They thought they were gonna bootstrap, and they just raised ten million dollar Series A, and the…”
Aug 26, 2025
Walling: Drip sale prompted by management fatigue and an unrefusable buyout offer
“We sold Drip. Part of it, I was unhappy with, you know, the fact that I was managing 10 people. I would have kept doing it. The other part is that we had a bunch of inbound interest, and then we got an offer that we kind of couldn't refuse.”
Aug 28, 2025 neutral
Sep 4, 2025 positive
Walling: SaaS deals requiring procurement now need $30k–$35k minimum ACV
“For a long time, I've been saying, you know, if you have to go through procurement, 25,000 dollar minimum ACV, and now I think I'm up to about, given inflation, literally, and just how many years it's been, it's like, I think it might be 30 or 35 is kind of my…”
Sep 4, 2025
Walling: Founders suffer more stress, but corporate employees suffer more depression
“Founders, as a rule, tend to have more anxiety and stress in their lives than employees of big companies, but employees of big companies tend to have a lot more depression than founders do. And this is, there's a, there's multiple studies that have verified th…”
Sep 9, 2025 neutral
Sep 9, 2025 neutral
Sep 9, 2025 bearish
Walling predicted in 2018 that Vidhug would not reach mid-six-figure revenue
“In its current incarnation, do I think Vidhug can be a, you know, a mid six figure business? I don't. And it's just my opinion, right? It doesn't mean I'm right or wrong, but I don't see an angle there as it stands today.”
Sep 11, 2025 positive
Sep 11, 2025 negative
Sep 16, 2025
Walling: Marketing skill progression mirrors software engineering
“Marketing is not the same as development, but the progression is similar. An entry-level marketer with zero to, I don't know, six to 12 months of experience Is comparable to an entry level software engineer with six to 12 months of experience.”
Sep 16, 2025 bullish
Walling: Starting SaaS is 5x to 10x harder than other businesses
“SaaS is one of the best business models, but it is one of the hardest company types to start. Because just building a SaaS and maintaining And hosting it, making it secure, making it performant, making it mostly bug-free, building something that people want an…”
Sep 16, 2025 neutral
Walling: Early Drip Plateaued at $8k MRR With 15% Churn
“This is exactly what happened with Drip in the early days, when all Drip was an email capture widget, and a email sequence, and that's all it did, and we were trying to charge 50 dollars a month for it, and people were like, I can cobble this together with oth…”
Sep 16, 2025 neutral
Walling: SaaS differs from info products because inactive users churn instantly
“And with info products, a huge percentage, let's say, 80 plus percent of folks who buy your info product, they never use it, and it doesn't matter, and you never hear about it. Now that sucks, but it's the reality. If someone's not using your SaaS, they cancel…”
Sep 18, 2025
Sep 23, 2025 positive
Sep 23, 2025 negative
Sep 30, 2025
Sep 30, 2025 negative
Sep 30, 2025
Sep 30, 2025 positive
Seven-figure SaaS requires higher pricing, not massive customer volume.
“If you really want to build a seven or eight figure SaaS company with net negative churn, you want to think about having higher pricing, and you want to think about having a few hundred high value happy customers that you can build into a multi-million dollar …”
Sep 30, 2025
Sep 30, 2025 negative
Sep 30, 2025 negative
Sep 30, 2025 negative
Serving 10,000 customers is an operational nightmare for support and churn.
“10,000 customers sounds sexy, but it is a nightmare for support. It is a nightmare if you don't have the process or the resources to be ready for it. More customers means more support. It means more churn, and it usually means more stress.”
Sep 30, 2025 negative
Sep 30, 2025 neutral
Sep 30, 2025
Founder burnout and mental health kill more startups than competition.
“The biggest threat to your company isn't gonna be competition. It's gonna be you. The potential for burnout, self-doubt, loss of motivation, destroying your relationships, mental health. These things kill more companies, I think, than any external force.”
Sep 30, 2025
Marketing and sales skills matter more for success than coding.
“Commandment number five is that marketing beats product. I know it's a tough sell to talk to a bunch of builders and let them know that your skill set is actually less important in entrepreneurial success than learning how to market and sell.”
Oct 7, 2025
Oct 7, 2025
Oct 7, 2025 neutral
Walling: Freelance videographers think more like consumers than B2B businesses
“In this case is freelance videographers, so it's more like super SMBs, right? It's like hobbyist plus plus, right? And I know that they're charging for things, but they are, they think more like consumers, I think, than businesses.”
Oct 7, 2025 negative
Walling: Slack's origin was not a pivot but a completely new product
“When pivoting first came out, they would say, like, Slack was a, it was like a video game company, right? And it's like, they pivoted the video game into Slack and said, that's not a pivot. That's just a, you just started a new product. Let's not, let's be rea…”
Oct 14, 2025
Oct 14, 2025 negative
Walling: 8% to 10% monthly churn prevents SaaS scaling to eight figures
“There are spaces that are eight percent, eight to 10% churn, and it's consumers, prosumers, indie hackers, hobbyists, And other folks who think like consumers, and those are not great SaaS businesses. They can be okay SaaS businesses, but they will plateau. Th…”
Oct 28, 2025
Walling: Startup validation is continuous until the company is sold
“You're validating until you sell that company. Like, you're still validating, do people need this feature? You're validating the every expansion, every strategic decision, every move you make, every marketing approach you add, you're kind of, Doing some valida…”
Oct 28, 2025
Oct 28, 2025 negative
Walling: Country-code domains harm SaaS marketing into the US
“I would not do a .co.nz domain because that will, it will be detrimental, especially if you try to market into the US. I can't speak for all the other countries, but in general, I think folks who live in a particular country or area are biased towards that are…”
Oct 28, 2025 negative
Walling: AI does not make category creation easier for bootstrappers
“So I don't think AI makes any of that any easier. AI makes building products easier, and it makes the type, it means the type of products we can build are more varied, and we can build maybe some new product types or categories, but building a product category…”
Oct 28, 2025 neutral
Oct 28, 2025 negative
Walling: Founders without millions and 3–5 years should avoid category creation
“My thing is, if you don't have millions of dollars and three to five years, To build a category, to start one, don't do it, right? And that's why most of us say it, because we have seen more, a lot more folks fail at it than not.”
Nov 4, 2025 positive
Nov 4, 2025 positive
Nov 4, 2025
Nov 4, 2025
Walling: Less likely to answer founders who show no prior effort
“When someone asks me a question, whether it's on the show or in person or via Email or via a contact form. If they haven't put any effort into what they're doing, or any deep thought, or any type of trial and error, I'm much less likely to give them a detailed…”
Nov 11, 2025 positive
Email software enables horizontal SaaS success due to inherent workflow stickiness
“Email is a space having built myself an ESP. It's a space where you can have a lot of success in that negative turn as a horizontal play. There are other spaces where that's harder. There's something about that stickiness of email and it's so permanent.”
Nov 11, 2025
Nov 18, 2025 neutral
Walling: Core four SaaS skills override weak support and messy operations
“If you really execute on the core four, product, dev, sales, and marketing, you can still build an incredible business with, unfortunately, it's not a path I would take, but with crappy support, with crappy customer success, with crappy internal operations, an…”
Nov 18, 2025
Rob Walling: Solo founders shouldn't disclose sole decision-making authority
“You don't have to tell them upfront that you are the solo co-founder and the solo decision maker. You can be vague about it when you get into these deals and you can play the same game of like, well, my, no, my co-founder didn't agree.”
Nov 18, 2025
Nov 25, 2025 bearish
Successful closed-source SaaS outnumbers open-source businesses 100 to 1
“There are so many more successful SaaS, closed source SaaS companies than there are successful companies that have been built on open source.
And it's not even like,
oh, it's half as many.
It, I would guess it's a, you know, a hundred to one ratio or something…”
Nov 25, 2025
Agencies building MVPs at cost need high equity to survive
“Because if you're effectively working for free, and I know they're paying for your developer, but you are doing whatever it is, project management, and hiring, and training, and, you know, keeping folks on staff, so to speak, and that's for free, there needs t…”
Nov 25, 2025 neutral
Virtually zero founders in the TinySeed ecosystem hold patents
“And this is why approximately zero founders in the MicroConf TinySeed Startups and Restless Ecosystem have patents.
There are some exceptions.
That's why I say approximately zero.
So yes, you can, I can point out two right now, but there are
More than what is …”
Nov 25, 2025
HitTail generated $1M in revenue and exit on $30k purchase
“All of the revenue plus the exit price was one million dollars. And I paid 30,000 dollars for it, and everything else was my time, and the expenses were minimal. I don't know if I had a 100,000 in expenses, I don't think the entire time I ran it was probably m…”
Nov 25, 2025 negative
Putting a SaaS on autopilot causes decline within 18 months
“Autopilot doesn't actually exist. If you put something on autopilot in any space that we deal in, it will decline over six to 18 months tops. Even if you have all this automated SEO, blah, blah, blah, like you'll just slide, and it will, you, the business will…”
Dec 16, 2025 negative
Dec 16, 2025 neutral
Walling: Founders should not delegate product management before $1M-$3M ARR
“I think you're probably, it's definitely one to two million is the earliest. I would consider bringing someone else in to start making product decisions, what you build, in what order, getting customer feedback, understanding your space, deciding how things ar…”
Dec 16, 2025 neutral
Walling: SaaS founders should keep marketing strategy in-house until $1.5M-$2M ARR
“The earliest I've seen any of them really bring someone in to collaborate on strategy, and I'll say they didn't hand it off completely, but it's probably about, certainly above a million ARR. I would lean towards 1.5 to maybe two million ARR, and this depends …”
Dec 23, 2025 negative
Walling: Unsupervised AI-coded software becomes unmaintainable within 6 to 18 months
“And it's okay to use AI to code as long as a, like an engineer is supervising slash running that process, because we know That you can have AI build you something, and we know that in six, 1218 months it will become very, very hard to maintain. Feature velocit…”
Jan 6, 2026 positive
Walling: Bringing Bootstrapper Pragmatism to Venture Capital Is a Superpower
“Now that I have like raised funding with tiny seed and I see companies that raise a few million, you know, we have a bunch of tiny seed companies that have done this. If you do it well, if you think about it like a bootstrapper, and you approach it like Laura …”
Jan 13, 2026 positive
Walling: Firing nice but underperforming employees is a difficult founder challenge
“Firing is actually really tough. It's tough to make that decision because it's always muddier than you think it's going to be. It's never as clear as you want it to be, and usually it's the really nice, but less than, slightly less than competent person, who y…”
Jan 13, 2026 negative
Walling: Launching multiple projects lets makers avoid the hard work of marketing
“The fun work is launching 20 projects. The fun work is building a bunch of projects. I love building, creating, that's what we are, we're makers. The hard work is focusing on one, And focusing on it long enough to see it through, and to put in the marketing an…”
Jan 13, 2026
Jan 13, 2026 positive
Jan 13, 2026 positive
Jan 20, 2026 negative
Walling: Spreading bets across many startups is terrible advice for founders
“There are a lot of people making excuses for being distracted and for engaging and feeding their entrepreneurial ADHD or their shiny object syndrome or their I need to be diversified or it's all a matter of luck so I need to make a hundred bets because one mig…”
Jan 20, 2026
Jan 20, 2026
Walling: Obstinate founders fail by clinging to initial methods without luck
“The persistent are the ones that, they just figure it out, and the obstinate are the ones that get in their own way over and over and over. And the only way they're successful is if they happen to luck upon the right answer from the start because they're so at…”
Jan 27, 2026 positive
Feb 3, 2026 negative
Feb 3, 2026 neutral
Feb 10, 2026
Feb 10, 2026 positive
Feb 10, 2026
Rob Walling: Co-founders should join separate mastermind groups, not the same one
“I would not want to be in a mastermind with my co-founder because I think it's a waste of time to have two high functioning co-founders getting the same information and spending that same time in a group. You want a myriad of opinions. You want different input…”
Feb 10, 2026 positive
Walling would choose C-Corp structure for startups targeting $10M–$40M exits
“So all that to say, today, if I were starting a startup, knowing what I know now, knowing that everyone sells, having seen folks, some folks qualify for QSBS and other folks not because they started an LLC or an S Corp, I personally would do the C Corp, and I …”
Feb 17, 2026
Feb 24, 2026 neutral
Walling: A 10K-listener podcast beats most videos on a 110K-subscriber YouTube channel
“We have a 111, maybe a 113,000 YouTube subscribers, and we have low tens of thousands podcast subscribers per month, or, I'm sorry, not even per month, per episode or whatever. And we get more listens to the podcast than most of our YouTube videos.”
Feb 24, 2026 negative
Feb 24, 2026 neutral
Walling: Under 5% of TinySeed's 210 SaaS companies built an audience
“Across TinySeeds, 210 companies, there were like four percent of those, maybe five, I think it was just under five percent, that had any type of audience Or have ever built any type of audience, and yet we have dozens of companies doing six, I mean, sorry, doi…”
Feb 24, 2026
Clouse: Niche content creators typically transition from high-demand one-on-one consulting
“A lot of the times the pathway is these people were known for being good at something. And so they started working with people one on one. And at some point that became unsustainable because there was just more Demand for that time than supply or interest in, …”
Mar 3, 2026 bearish
Every successful no-code or AI vibe-coded startup inevitably requires a rewrite
“Every company that I've invested in or otherwise had visibility into that has been no code or has been poorly coded, I will say, I'm just going to assume that AI vibe coding is poorly coded and hard to maintain long term. That may or may not be correct. But wh…”
Mar 3, 2026
TinySeed targets $1M to $3M valuations for 10% to 12% equity
“We do 10 to 12% for, what is it, 120 to, usually two 20, so the valuation, I think that's one to two million, or one to two and a half million, you get it. And the two and a half 1,000,003 million dollar valuations we've done, someone had a hundred K of MRR wh…”
Mar 3, 2026 neutral
Mar 17, 2026 bearish
Mar 17, 2026 negative
Walling: TinySeed explored and rejected launching an RBF debt fund
“Einar and I at one point, this is six, seven years ago, talked about should we raise a debt fund, right, and have Tiny Seed Capital. I don't know what we call it, but whatever, you know, you get the idea. Tiny Seed RBF. And when we looked at the amount that we…”
Mar 17, 2026 positive
Mar 17, 2026
Mar 17, 2026
Walling: Bootstrapping a solution-unaware SaaS requires outbound sales or outside funding
“This is a hard way to go as a bootstrapper. It's really hard, and it infectively means it's mostly outbound, and usually you're either good at that, and that's what you want to do, and you want to do outbound, and you want to do sales, or you raise money to do…”
Mar 31, 2026 neutral
Walling: TinySeed manages nearly $60M AUM and 210 investments with 11 staff
“Tiny team, think of like MicroConf and TinySeed is nine full-time people and two part-time. And we have invested in 210 B to B SaaS companies in the last seven years. We run all the MicroConf events in addition to mastermind matching and connect. We push out t…”
Mar 31, 2026
Walling: Owner-level work is making hard decisions with incomplete information
“A lot of decision making as an owner level thinker, making a lot of hard decisions with incomplete information, versus as a task level thinker, you don't have to make hard decisions, and you usually have very complete information. And as a project level thinke…”
Mar 31, 2026
Walling: Task-level thinkers plan in hours; owners plan in years
“And I think of it like a task level thinker probably thinks ahead a few hours Or maybe, depending on the task, a day or two. I think a project level thinker is thinking ahead weeks, maybe a few months, again, depending on the size and complexity of the project…”
Mar 31, 2026 positive
Walling: Hiring true owner-level talent requires director-level roles or above
“I think generally if you want someone who's really going to take control of an entire area, entire business unit, entire, you know, whatever, you want them to take ownership, I think you're talking at director level or above.”
Mar 31, 2026
Walling: Relying only on cheap VAs creates a founder bottleneck
“Only hiring virtual assistants, or really inexpensive resources, and really junior resources, and training them up, and giving them SOPs, and it was fine, and it was what I needed at that time, but it came back to bite me later, because it was a bad habit that…”
Mar 31, 2026 neutral
Walling: Experienced owner-level thinkers command low-to-mid six figures
“If you get someone right on that cusp, who becomes an owner level thinker within the first year or two of working for you, then obviously you can get them at a, You know, at a certain salary range. And if I think U.S. Or North America, I mean maybe 80, 90,000.…”
Apr 14, 2026 positive
Walling: SaaS pricing pages must include a 'Call Us' tier
“You have the individual plan, and you have your financial planner plan, and you have your call us plan, because you should always have that, because you never want to have someone come who should be paying you 35,000 dollars, and they sign up for your financia…”
Apr 21, 2026 negative
Walling: 'Zero to One' and venture books do not help bootstrappers
“This is the same reason I cringe when people talk about reading zero to one and then trying to apply that to bootstrapping, or that that's a big motivational entrepreneurial book when they're starting, when they want to start a million dollar SaaS company. It'…”
Apr 21, 2026 negative
Apr 21, 2026 bearish
Apr 21, 2026 positive
Walling: Consistent volume shifts creator focus from metrics to shipping
“When you ship your fifth book, and your 800th podcast episode, or your seventh album, or 14th album, I do think that That at a certain point, the process takes over, and the desire to ship things into the world overrules or outweighs necessarily these ancillar…”
Apr 21, 2026 neutral
Apr 28, 2026 positive
Apr 28, 2026 neutral
Apr 28, 2026 positive
Apr 28, 2026 bearish
Walling: Almost no TinySeed startups have built MCP or CLI integrations
“How few, even tiny seed startups that are like, bleeding edge, Almost none of them have MCP and CLI, and the ones that do have two users, three users, is not, we are not nearly as far as Twitter would have you believe, right? We're like, oh, everyone's buildin…”
May 5, 2026 bullish
May 5, 2026 negative
Rob Walling discards $10-$15/hour Upwork bids due to quality concerns
“When we go in to post a job, I will not take the low end bids on Upwork at all, because I just, I don't think the quality's gonna be there. So if we post a job and we get a 40 dollar an hour bid, or a bunch in the thirties and forties, and we get a bunch in li…”
May 5, 2026 negative
May 5, 2026 negative
May 5, 2026 negative
Walling: Building software for secondary job responsibilities is a common trap
“I think it can be an easy trap to think of building for folks who don't have the budget or the real interest, and this is kind of a, it's a side project for them, right? And I don't mean a hobby, I don't mean a nights and weekends, but if their main focus of t…”
May 5, 2026 positive
May 5, 2026 positive
Rob Walling: Freelancers are best for temporary gaps or 'black box' roles
“For me, freelancers are to fill either a temporary gap or what I call a more of a, it's a black box role, and what I mean by that is if I could put a black box here on, on the desk, and you could feed it in some kind of input, and you know the output you want,…”
May 12, 2026
Walling: App store search ranking matters more than TAM for early apps
“TAM is not going to be the limiting factor. It's going to be Term, total reachable market, that you can actually get in front of, and more than that, it's just going to be, can you rank for this term in the Shopify app store? Can you try to get to number one f…”
May 12, 2026 negative
May 12, 2026 neutral
May 12, 2026 neutral
May 12, 2026
Walling: Customer feedback cannot dictate how a founder should pivot
“If you have 50 customers that are not really paying or churning, and you ask them what you should do differently, they'll tell you 47 different things. And as the founder, you have to make the hard decision with incomplete information to figure out what and ho…”
May 12, 2026
Walling: Left $250k–$300k consulting business when software hit $100k
“I remember I was making between 250,300 thousand dollars a year as a consultant. I was a microagency where I was doing a lot of the work but I was outsourcing to freelancers and I was making a big cut on those folks. This is 2000 seven, eight ish time frame an…”
May 12, 2026 neutral
May 12, 2026
May 12, 2026 neutral
Walling: Determining if marketplace apps can go standalone requires live product data
“Until you get something live and get people using it and see how fast it grows and see where it plateaus, I think it's going to be really hard to try to answer all these questions because there's just not publicly available data on this topic.”
May 12, 2026 positive
Walling: Extreme time constraints force founders to master prioritization and delegation
“I would say you are going to have a superpower of being able to prioritize and delegate ruthlessly, and most people don't have to learn that. Look, if I was single and I was 24 years old and I have infinity time, let's say I don't have a day job, I'm in colleg…”
May 12, 2026 negative
Walling: Founders repeatedly redesign products to avoid hard marketing work
“I see a lot of makers and designers who, Build a product and then just redesign it over and over. I'm going to redesign the landing page again. I'm going to redesign the homepage again. Instead of actually doing marketing and doing the hard thing, they just wa…”
May 12, 2026
Walling offered competitor employees consulting fees for interviews, but none charged him
“And at one point when we were building Drip and I wanted to talk to some Ex-sales people and marketing people from some competitors of ours who used to work at those competitors, I similarly contacted them via LinkedIn, said, I'd love to talk to you, and said,…”
May 19, 2026 bullish
May 19, 2026
Jun 16, 2026 negative
Walling: Engineers Without Product Sense Build Inelegant, Overly Literal Features
“If you give a developer who's not a product person a feature, and you say, build content snippets that people can insert into their emails, you know, if your app sends emails for people, they will build it very literally, and it will not be very elegant nor in…”
Jun 16, 2026 positive
Walling: Bootstrap founders only need roadmap prioritization and UX skills
“The two biggest skills I think you want to develop is figuring out of all the feature requests of everything coming in from support and sales and from your own head, all your internal and external everything that you could build next, It's figuring out what to…”
Jun 16, 2026
Walling: Product Intuition Does Not Easily Transfer Across Different SaaS Domains
“There's a certain amount of repetition and understanding and practice, and it can translate from app to app, but I don't think it, like, just because I was, yeah, Derek and I were good at product at Drip, I wouldn't be good at product at Simewell. I mean, it w…”
Jun 23, 2026
Jun 23, 2026 positive
Walling: Being 5x underpriced can artificially cap a $1.25M startup at $250k
“The thing I want to call out is that pricing is the biggest lever in SaaS, and if it's messed up, For example, if you're five X underpriced what you could be charging, you will build a 250,000 dollar business at best when it should be a 1.25 million dollar bus…”
Jun 23, 2026
Jul 7, 2026
Walling: Higher SaaS pricing unlocks far more viable marketing channels
“Because of all the 20 B to B SaaS marketing approaches, if you have a price point of 50 dollars a month, I think you can do four or maybe five of the B to B SaaS marketing approaches. If you have a price point of 500 a month, you can do between five and 10 of …”
Jul 7, 2026
Jul 7, 2026 positive
Rob Walling: Founders must ship even if competitors launch similar products first
“I think that you should ship things even if someone else launches something similar. It sounds like you might be looking for excuses not to ship because that feels Scary, right? Shipping feels scary, and pulling it and not doing anything is less scary.”
Jul 7, 2026 negative
Walling: Low-LTV consumer software can only be marketed through free channels
“The only way that you can market a consumer-facing business that I know of, the only ways, I should say, are virality, word of mouth, SEO, it's all the, it's the free stuff, because you can't afford to spend or invest any money on marketing, and that's why, on…”
Jul 7, 2026
Jul 7, 2026 positive
Jul 14, 2026 neutral
Jul 14, 2026 negative
Jul 14, 2026 negative
Free plans and one-time payments are crutches for early-stage SaaS
“So the desire for founders to do free plans, to underprice their product, hey, nine bucks a month for something that should probably be a hundred bucks a month, and to try to do one-time purchases in the early days, I think is a crutch.”
Jul 14, 2026 positive
Break even on onboarding for $5K ACV SaaS; mark up lower tiers
“Typically, with consulting services built on a SaaS, I'm fine to break even If I'm charging enough on the monthly recurring. You know, if my annual contract value is 5000 dollars a year and up, and I have net negative churn because of the work I did up front, …”
Jul 21, 2026 neutral
Jul 21, 2026 bearish
Jul 21, 2026 negative
Jul 21, 2026 negative
Jul 28, 2026
Walling: Successful founders execute rapidly and are right 60% of the time
“Generally, the people who succeed, they do a lot of things, and they're right more often than not. Not all the time, but they're right. They can be right 60% of the time, but they just do a lot of and the founders, and they're not flailing.”
Jul 28, 2026 negative
Walling: Swooping in to solve problems created a decision bottleneck at Drip
“It's not good, and I was Mr. Swoop in, and I was like, well, obviously I'm a founder, so I can solve all these problems, and it really burned me out, and as you said, it taught my team to just come to me with everything, and it was not good for growing the org…”
Aug 4, 2026 positive
Aug 11, 2026 positive
Aug 11, 2026 positive
Walling: Downloaded Rocket Lawyer contract templates passed M&A due diligence
“Did I go to rocketlawyer.com years ago and download templates For employment agreements and IP agreements and basically skim through them and use them as is? I did. Did those pass the muster when we got acquired? Yes, they did.”
Aug 11, 2026 neutral
Walling: Idea validation only provides 30% to 50% certainty
“You don't get to a hundred percent validation. You don't get to where it's like, oh, the hundred percent, this will work. There's no way. Maybe you go from zero to a hunch, which is 10% to, I mean, doing validation and vetting, do you get to 30, 40, 50% certai…”
Aug 11, 2026 negative
Walling: Cloud programs require VC backing as cheap applicant filtering
“The challenges with these startup programs, Is they want companies that have, ultimately have a lot of money to spend, and it is giving away the razor to sell the blades type thing, or giving, you know, the first piece of candy is free, and they want you to st…”
Aug 11, 2026 bearish
Aug 18, 2026
Aug 18, 2026
Aug 18, 2026
Aug 18, 2026
Walling: Do Not Make Big Decisions When Dysregulated or Anxious
“You should not
Be making big decisions when your nervous system is dysregulated, when you feel that tightness in your chest, when you're really concerned and worried, and you're thinking in a pattern that isn't, it really isn't that healthy. It's certainly not…”
Aug 18, 2026
Walling: Direct mail SaaS acquisition requires high ACVs and upfront capital
“The couple challenges are, you need a high enough annual contract value to justify it, and you need cash up front. Because especially at the start, you're going to send a lot of letters or gift boxes that aren't going to work as you optimize your process. And …”
Aug 18, 2026
Aug 25, 2026 negative
Walling: Long enterprise feedback loops are dangerous for bootstrapped founders
“I think it's dangerous for a bootstrapper to have a feedback loop that's this long, because you're just going to waste years of your life. I can't imagine taking, that's such a risk. The opportunity cost of this is significant, so I would either be looking for…”
Aug 25, 2026
Aug 25, 2026 negative
Walling: Building 10 Products to See What Sticks Is for Inexperienced Founders
“I don't know of any successful founders who are on their second, third, fourth Effort that build 10 things and see what sticks. I know literally zero. That is an approach for someone who I would say just doesn't know any better.”
Aug 25, 2026
Sep 1, 2026 positive
Sep 1, 2026 negative