The Wisdom Wall

“And that is the traditional org chart in which we all have an SVP, a VP, a director, an IC is broken. I believe that the best way to run a company is by having a flat structure.”

“So what he's referring to by Founder Mode is that we're told that we can run our company by hiring great people and get outside of their way. Senior, great people. That sounds lovely in theory, in practice, because we're founders and we're very particular about things, and because we see a lot of things differently,…”

“The best investors are not going to bother you. They're not going to help you. Nobody's going to help you. You're in by yourself, no matter who promises what to you, but the worst investors will actually give you better advice and, and really create more headache for you.”

“and then I do think it's actually a huge mistake to have a fifty-fifty split with your founder when you start a company, because even if it's 51, 49, somebody needs to be in charge and control the board.”

“do not listen for advice from people who've not done your job. That's my number one advice. It doesn't matter if you have a Investor from Sequoia or Andreessen. We've taken money from top investors, including Sequoia. It doesn't matter if you are a board member as a billionaire, or this or that, or have been on a board…”

“Now, as SaaS companies, most SaaS companies are told Not to get into services. But the services layer actually can add a lot of stickiness. So think of it as 80% SaaS, 20% services. That thin layer, I think, can make accounts much more stickier, especially when you're going to the mid to large sized businesses.”

“So if your reps don't have 15 meetings a week, then what that means is one of the ways that you can drive improved efficiency is by reducing the number of reps. I'm sorry, uh, to be callous like that, but the point is great companies are routing more resources, meaning their best leads, to high-performing reps, and…”

“You could be a good writer, but if you don't buy backlinks, if you don't buy referring other domains, it will not work.”

“And I would also add on that bootstrapped companies learning from venture-backed companies is counterproductive. To their overall growth.”

“best practices are for losers, full stop. They're for people who want to be average. Like, nobody who follows best practices builds great companies or builds exceptional companies.”

“And they're not your friends. You know, what they're doing is they're making money from your decision to go into business as an entrepreneur and make money. And that's a different thing, and you, my view would, oh sorry, my view would be, you know, exploit them if you need them. If you need them for upfront capital, if…”

“I've always told investors just, you know, you'd be better off buying a basket of stocks that have the lowest NPS of all, and they'll outperform the companies that have the best NPS. And, and you'll be like, well, it doesn't make sense, but think about the companies that have compounded the best over a long period of…”

“if you are just starting, or, um, if you are just below ten million dollars ARR probably, you should, you should focus on building a shut up and take money money product. So, focus on getting those early adopters. They will basically Either buy your product or not. They don't care about, you know, trials, freemium. If…”

“the first time I did it, I did not rewrite the platform. I rewrite their code base, um, and I, that's, in fact, um, in long term, a huge mistake, right? So because now you have multiple code bases, and my team doesn't want to work on better, and there's all this, all these cultural issues start coming into play.”

“This is the counterpoint guys, the VC argument that you shouldn't sell services inside of your SAS. I would always argue the opposite, which is if you touch a SAS sale with a big upfront fee, like five K, they're just not going to turn your net dollar retention. It's going to be through the roof.”

“forget about your hobbies, you're not gonna be a good friend, son, daughter, mother. You gotta ruthlessly prioritize, identify the things that really matter to you, and only do those things. It's not a good time to have a work-life balance.”

“Yeah, there's gonna, you're gonna read articles that say, like, oh, the pop on day one, like, that just means you, like, did a bad job of pricing your IPO. It's not really true. Like, we had the best advisors, the best people around the table on this. You don't really want an IPO that doesn't go up on the first day,…”

“A bootstrapper who only spends what his customers pay him or her is sustainable. They will outlast the VC back competitor every time, and they will probably win every time.”

“Raising capital does not validate an idea. It means you're a good salesperson.”

“we should be investing in automation, and we should be, we should get out of this, um, I'd say almost like, it's like a trap of full employment, this belief that, that it's best for people to be doing these jobs. Um, I think that we should be aiming for full unemployment. Like, our goal should be how much, uh, if a job…”

“my hypothesis is that, You know, if you need to create a large hyper-growth company, whatever you've built in the first, like, 18 months or something is sort of the extent to which you're going to build in the life cycle of your company.”

“And if one does, Or if one starts accumulating behind the scenes, they all have to. It moves really, it starts to, it starts to move really fast.”

“We break the peg, and then for them to, in order to keep this, this system afloat, they systematically kept dropping interest rates until they got to zero percent, which is where we are today. So when you look at that 10 year yield chart over this 80 year period of time, it's this perfect, goes straight up, goes…”

“all the capitalists on wall street become socialist in times of crisis.”

“what you see is a lot of these stock to flow models and, um, co-integration models, et cetera, that are used in gold. Apply to Bitcoin and are actually more accurate in Bitcoin because one side of the equation is transparently known with 100% certainty and all you have to model is the demand.”

“So, uh, in my mind a little bit, I think bootstrapped is actually a code word for founder wealth.”

“Because you meet all these guys and they're like, oh, it's just like a marriage. We're going to be partners. You know, we like to let entrepreneurs run their businesses. And like half of them are telling the truth and half of them are not. The half that are not want to like do things that the way they want to do them,…”

“I have a big issue when people sell lifetime plans. I think it's cheap. I think it's a marketing tactic, and I think it's totally disingenuous and hurts your personal brand if and when you have to shut the company down or sell it.”

“People's attention spans have not changed since we sat around the fire in caves. Your attention span is determined by your genetics, and the human genome hasn't changed. What has changed is people's interest spans.”

“Like, to celebrate raising money is to celebrate that you took out a loan.”

“With the exception that no business you cared about was ever built that way. Like every business, every, all the top names in the industry are built through word of mouth. And, but no one talks about that because it's not possible to be funded with, with, with capital. And so therefore VCs don't care about word of…”

“Cause I would say like, I think about month, like revenue, obviously in month and month annual growth, but I would say, um, all, everything else is just a vanity metric. Number of users you have, number of customers you have, um, conversion numbers, all those kinds, like those are kind of interesting in, in the…”

“I think the most important decisions are generally not quantified. Um, we're not quantifiable. And so I'd say if you're running your business because you can prove with numbers that your decisions are good, you're going to fail because I mean, someone else out there who's bolder than you, better numbers stinks.”

“the way I would suggest would be a better way to do it is take a small slice of it. Like the, uh, the amount that you would give like an early VP or, or someone who's, who's, who's high up in the organization, but not, not a founder and give and invest that portion over four years and then have the rest vest at, uh,…”

“when that number one divided by your churn projects like your L, it will project your LTV at like, oh, you're three and a half years or four years. Meanwhile, every year your business changes, your contract values change, um, your contract lengths change, your product can get better or worse. So it's really not…”

“Uh, because there isn't a discoverability issue in podcasting. What there is, is an ease of consumption issue. And, and what Marco did with his app, Overcast, he made it easy for people to consume the content they know they want to consume.”

“But if you look at an audience of 300,000 in email, and you compare it to, say, a podcast audience of 25,000. You'll often find the podcaster making more, or generating more revenue than that email marketer.”

“I'm a big fan of kind of like attacking metrics in order of risk. I think a lot of people are like, Like they launch and they're trying to monetize and get acquisition and prove retention. And I'm a big fan of like, okay, let's take those five kind of metrics and take them one at a time. And so we first focused on free…”

“You can at least double, if not five X, what you're getting off your traditional chatbot with a superhuman.”

“You can't just One AI on each and every system in the office of the CFO. You have to give it the context of the end-to-end data from all the systems that participate in the business process.”

“don't do the move of like founders eat last. I also think that's old and antiquated. Like you have to understand your worth.”

“you can put together a prototype, like, uh, and you can vibe code your way to kind of a, you know, a simple scheduling app, uh, but you can't vibe code your way to, to something that has kind of deep value to, uh, a domain.”

“That's false. So, uh, you can have people based in India sell to a large enterprise US customers. You do need some face time. So, uh, uh, myself, uh, my co-founder and the salesperson at times will be traveling to the US and Europe. So those are seasonal or periodic trips that we make to make sure that we are in front…”

“Apple is a merchant of record. Um, and Apple deals with, you know, you don't have to deal with chargebacks, you don't have to deal with disputes, you don't have to deal with taxes. You also don't have to deal with involuntary churn. Because I have news for you. If your credit card expires, you're not going to…”

“Initially, we had no animations, we had no GIFs, it was, Very bland. We only asked the questions we needed in order to give the user their calorie daily intake estimate that they would need to gain weight or lose weight, and That was, it was purely utility, but then over time, we started A-B testing different…”

“We also observe that we're gonna sell less well if, sorry, they're based in Europe, they take forever to close. Um, if they're on Outlook, for some reason, people that use Outlook, they're a lot slower to make decisions as well, um, and if they're a traditional company.”

“You can over invest in acquisition. You can over invest in retention. You cannot over invest in onboarding. It's the most important motion in your business, especially if you're a product focused business, right?”

“A way to think about it is if, let's just pretend you're growing a hundred percent a year, and then you raise a growth round for twenty-five million dollars, you sell a third of your company, and now your share count is a third bigger. But if your growth rate goes from a hundred to a 110%, You actually didn't create…”

“The most successful software companies we see that are most underwritable, bankable, they usually launch an agency.”

“Shall you buy backlinks? Yes. Shall you buy from the low authority, uh, website? Please don't do that because Google recognized it, uh, and then you can be penalized, yeah? So if there is something for cheap in the market, usually, uh, there is a trap.”

“But, you know, now I believe that in the world of AI, general brand awareness will become more important. It's the same as, like, human brain, yeah? If artificial brain will not see you as a market player, they will never recommend you.”

“if you manage the SaaS well, it's almost impossible to get into bankruptcy. It usually only happens if there's a VC pouring too much money. Um, founders go crazy. The, the environment tanks.”

“One of the things here is don't let your BDRs do lead research. Give them the leads and make sure, and if they say they need to, uh, do anything with them, it means your model's broken.”

“my view is, you know, if you raise a hundred million dollars, you should be able to generate a hundred million dollars of error off of that platform over time to pay back for the time that it takes to get to that hundred million dollars.”

“Because the platform product is way more durable than the single vertical product. And the single biggest problem people make in investing and starting companies is they think they, because they get a lot of great feedback from their customers because they're solving one narrow need, they're worth 10 times revenue. In…”

“I'm a firm believer that this, that the founder should be doing sales, and doing some other marketing for the first two years. They should be the one closing the first 10 accounts. If you're not doing the, I closed the first 40 accounts, because we were bootstrapped and it was, you know, we had a long run, but I do…”

“Do SEO, paid ads, and email in that order. If your CMO tells you to do anything different, they don't know what they're talking about.”

“Um, whereas we stayed focused on the U.K. Market and his advice was stay focused on the U.K. Market until you get to ten million AAR and then, and then, and then look at the U.S. Market. And that real, that was invaluable advice and stopped us blowing through our money too quickly.”

“you don't have a brand when you're zero MRR. Like, you can do outrageous things with zero consequence, as far as I can tell. Like, The worst thing that happens is you just start over and everyone forgot what you were doing in the first place.”

“no one's going to care about solving pain points right now, but everybody needs to hit goals, right? And if we can identify their objectives and sell to objectives as opposed to pain, certainly not features, right? Because that doesn't matter. People are going to trade features for objectives all day long, right, right…”

“venture capital is not, For everyone, I'd say, in fact, for a very small percentage of founders and companies, I'd say a lot of SaaS can be built without venture capital and should be built without venture capital.”

“For us, what we see is that there is no real MVP in this market. Like if people come to us and say, Hey, I want to be a build.com for my clients. I can't give them like a scrappy little solution that doesn't really work. I have to give them something a lot more ready. And it actually takes a lot of effort and time to…”

“If somebody's gonna be a CTO when you're three people, and then you get to 30, and that person no longer is relevant in that role, then you're gonna have to top them, they're gonna look like they took a demotion, it just creates all sorts of agita and anxiety that you can avoid, By just giving people reasonable titles.…”

“If you give everybody input into what the culture's gonna become, you're gonna have a shit brown culture. And so what you got to do is say, nope, this is our culture, and we're going to spike on these two colors, and that's it”

“When you see somebody who's taking a lot of L's, like, you know, hey, I was at a startup, it failed, my prior startup had this problem, and you look at their resume, and it's just like a string of losses, like, don't hire that person.”

“So there are some geographies which are time rich, but money poor, and if you sell save time there, it's not going to work. But some geographies which are money rich and time poor, then save time value proposition and messaging is going to work.”

“If you're still at two million ARR, trust me, you haven't really created a repeatable sales motion. You've created some validation. It ain't repeatable sales motion yet. You've just had your founders sell stuff, right?”

“More opportunities, resources, and tooling reduces the barrier to entry. Increases competition, resulting in velocity being the only true sustainable advantage.”

“Companies in the Nordics and Western Europe are willing to pay 20% higher prices for the exact same product relative to the U.S. So, go increase your price by 20% in Western Europe and watch your conversion rates stay the same.”

“churn in our space is typically much lower than software churn.”

“I always said, I could underwrite a restaurant better than a bank. I don't need your tax returns. Just put a sensor in your restaurant, and I'll track the traffic and be able to lend you better than any bank could, and a bank can't do that, and in a similar sense, they can't lend to a website. They can't lend to a SaaS…”

“we gather data on what they're spending time on, and we basically found that, um, you know, there's way more impact on spending a bit more time on monetization, a bit more time on retention, compared to spending time on acquisition.”

“Our niche was highly competitive, so we were to compete with Ahrefs, SEMrush, HubSpot, big domains, big players, so if that's the case, you will need to wait for results for a long time, like a year or so, and you'll need to invest a lot of money, and if you are bootstrapping, you don't have this money, and ideally you…”

“if you're profitable, uh, over one million dollar a year, you do invest in SEO, so we just waited for, for some time.”

“I think the, the, the, the kind of like the, the trigger is in the, in the 60, 70 range where people can look at that and say, like, can we get this to 203 104 hundred, really, right? Um, and that's a linear argument. I mean, it's still a pretty, Pretty big lift, but it's a linear argument, right? But, but from 30 to…”

“a lot of founders in China grew up being under a different, very different regime. Um, their mentality is that let me grow it and let me take control of it. The investors are just, you know, capital money. They're, they're debt. They're not equity.”

“So when the lever you, you can pull is R and D expense, right. And you feel like you're just going to, the pace of innovation will just slow down a little bit. Then you can actually keep your revenue growth, but then drop your OPEX growth, right? The second that you have to dip into that sales and marketing expense in…”

“I think like five years back, the story was very different, but they've learned, they've trained themselves and the really good ones have, have figured it out. And of course that pool is much smaller than what you'd like it to be. Uh, but it's still much cheaper than having a U S rep.”

“Yeah, because like if you launch there, uh, you get wrong kind of customers. You don't get the kind of customers that are going to be with you like long-term. Uh, they don't count towards, uh, churn like retention. It's a lifetime plan. It's like only good for like very specific companies when it makes sense.”

“I've seen so many times where they say yes to you at first, and then they will retrade you, so your terms get worse at the very, very end, right? So, uh, a yes is never a hundred percent.”

“Sometimes things have to break and fall over to actually see what you need to fix.”

“in all the startup schools, they'll say, they'll tell you fail fast and, uh, and learn from it. Uh, great learning when you have a huge industry and you can sell to as many people as you can and you'll never remember the people that you failed with. Not in the smaller industries. Reputation is the key and your fast…”

“sales or marketing or anything on the revenue side pays off at a pays off faster, but at a lower ultimate rate, um, engineering resources and actually making the product better, creating that extra feature that wins you extra deals pays off at the highest rate, but over a longer period of time.”

“I think that the rule is debt before equity. If you can get it, it's cheaper. Equity capital is super expensive. You can't get debt until you already have revenue. Once you can get debt, you should get debt. You stack equity on top of it. But even if you just push your, the equity round back six months, you're, you,…”

“when people say, oh, we're going to save a bunch of money by running a remote company. Not necessarily. Running a remote company could be expensive. It's a talent tech. Strategy. A hundred percent because now the total addressable market of people that you're hiring is the entire world, right?”

“my number one takeaway on that is only use it for Things you know are working. Marketing channels you know are working. It's not for testing. It's not for hiring. It's not for growing product. It's none of those things. It is, I know that if I spend a dollar here, I get two dollars back, and I need to spend more of…”

“We firmly Believe that scorecards are stupid. I think that scorecards make you feel like the choice that you made makes you feel better about the choice you made. Um, it only reifies your existing values and your existing choices.”

“Yeah, because honestly, the problem, the problems that are That, that user versus the problems that are a larger company user, they're almost identical when you're talking about launching products. Like I, I actually fundamentally disagree with the idea that they are the wrong user. They're just users that have a…”

“Prices going up. That's the only CTA that works, too. Nothing else works. Prices, discounts don't work. Great speakers, you know, nothing works but prices.”

“The minimum you need five hundred million to a billion to make it a long-term business, sustainable business”

“We, we really have a, uh, a lens on the world that says vertical SaaS platforms are literally worth three to five to 10 times more if this strategy is implemented well with the right technology”

“I think it's absolutely critical to raise money from external investors, even if you can fund it, or you think that you can fund it, your ability to raise money is the number one thing that will determine your future success.”

“it's almost a problem that you have revenue because then people want to harp on you about how low the revenue is when really you should just eliminate the revenue and just focus on user and engagement growth”

“At the end of the day, it's still, uh, quite heavily regulated in consumer credit business, meaning the barriers for entry are quite high and you do carry underwriting and default risk, meaning that you need to have a proper treasury collection and credit risk function. So if you throw a lot of money in it, throw a lot…”

“whatever price tag you give, you can divide it between what you pay today, and what you pay tomorrow, and what you pay the day after. And whatever you pay tomorrow and the day after usually has some contingencies, right? If you think about it, like, yeah, I mean, you, you are in the shared boat at that point. So your…”

“You know, I said it's like a restaurant critic that literally can't eat the food, right? The analyst can't use the software, and they just stand outside the restaurant asking other people, how is your meal? And I'd rather ask the people eating the meal, right? And that's why we said it's kind of a Yelp for business…”

“I think, so what's interesting is token projects on, on par kind of raise less money Then equity projects, uh, because the community is doing more of the work. Right. And, and getting more of the ownership.”

“No, absolutely not. Because then it's very difficult to expand. Whereas when you come in with, uh, with a full vertical SAS, then it's, uh, it's easier to expand.”

“IoT isn't that commodity that we think it is, especially because of installation time, setup time, and so on. So if you really nail down the hardware part, you can go to go to market more easily, and you can just have like more successful customers that are paying more, expanding more, and that you also can upsell…”

“I realized that a lot of our churn was, was because of, uh, micro SMB, you know, entrepreneurs not being good entrepreneurs. So we had to fix the, the, the mindset of, of the customer coming into the gate about business, not really about our product.”

“our customers don't want us to take deposits. They, they don't, you know, the, we're embedded fintech, so we have, uh, uh, You know, a FBO account, or think of it as like a Venmo account. We have a holding account. That's what our customers want. They don't, they want Chase. They want Bank of America.”

“I think, uh, raising money in my mind is a form of de-risking. A venture. Um, I think some people think that it like increases the risk, but for us, I see it as like a form of de-risking.”

“You're going to raise two million out of 10 pre. Whatever your buddies that you, but you take your buddy, your old boss's money, whatever. Great. Great for you. Then you're going to keep growing revenue and you're going to get a six million dollar acquisition offer and you still own 70% of the business. You'd love to…”

“once you get into rounds that are this, as big as like this five train round, you know, five hundred million bucks. Part of that investment is defensive where you were essentially declaring yourselves the winner of the space and, and like excluding other folks from going and taking meaningful market share.”

“It's, it's easier to monetize media, frankly, than it is SaaS. I don't know that a lot of people realize that. Um, but the great thing about SaaS is it, like once you get that engine going, it's, it has its own set of momentum, which doesn't require you to put as much into it.”

“The number one valuation driver in SAS is net retention.”

“if you work six hours, seven hours, eight hours a day, you won't get your business up and running.”

“The worst thing that can happen right now is that I start to pollute my data set because I think I have everything solved. So we are extremely protective about that data set.”

“That's always cheaper than equity. If you think you're going to be successful, that is always cheaper.”

“I think I did some rough math. I think over the next two and a half to three years, we're going to pay them upwards of two million. Whereas if we did a dilutive round now at exit, that dilution would be minimum, twenty million, like bare minimum.”

“to me, I spent 800 dollars a month on use proof anyway. So the company's immediately at 800 in MRR, which then gives me the leverage to say, okay, that's 7200 or whatever it is. 9600. I'm sorry. In ARR, which then I could go and sell for a hundred.”

“If you take that capability and apply it to your screen, it would know exactly what's going on, right, because the resolution is so high, and so it can understand the text really well, OCR accuracy has improved dramatically, and so if you can understand what's going on on the screen, then it's possible to control the…”

“If I go see people hire VPs of sales from places like Oracle, Or some other big company as their first rep, the biggest challenge, the biggest reason they don't work out is because they haven't actually built something from the bottom up. They haven't built the process from the bottom up. They've never built a sales…”

“that's, that's how I decide whether a network marketing model is ethical or not. It's based on whether if they don't recruit other people, do they still get value from the product itself?”

“consumer investors would always like extrapolate their preferences on, uh, on, on the company or sorry, on the investment decision. And I don't like the taste of us. No one will like the taste regardless of the data. Um, and what they miss is that the data was identifying that the company's performing exceptionally…”

“So I put 99% of the emphasis on getting feedback and one percent on protecting ideas. Um, I've literally never seen an idea stolen. Okay. I mean, I've seen ideas copied. I see it all the time. Um, but I've, I've never seen somebody outrun the entrepreneur. Um, most people who are capable of running with an idea already…”

“So I strongly believe company cannot live without CEO. That's for sure. Most companies cannot live without head of sales and CMOS. But probably you can leave without, you know, a CTO. You can hire a CTO.”

“If you don't get professional services right, you see pre-live churn spike, which obviously impacts your universal churn. And then post-live churn, you want to drive down below 10% Uh, and get to sort of four percent and be super sticky. And that's why professional services and the customer success journey host…”

“Our, our performance of these dramatically exceeds any other lender because of the way we underwrite and the way we establish limit. We can give, you know, three X the limit because we have a process that says, what do you, it's not about the, the person buying the lumber. It's a little bit about the lumber, but more…”

“I mean, so for our audience, authenticity is critically important. Um, I think that's true for, for technical audiences in general. Um, people just smell sales and that kind of thing. And, and nothing feels worse to me than buying a community, right? Like it just, well, I don't, I, I, I just think, I think that our,…”

“a lot of founders make the first sales hire, they make the assumption that that first sales hire should sell more than the founder, and it's almost never the case, because the founder knows the product, the founder has an unfair advantage, because customers always want to talk to the founder, there's a little bit of a…”

“because I know a lot of people, you know, they're trying to put bonuses on number of qualified leads, marketing qualified leads, sales qualified I think it's too complicated, and I think people tend to always optimize things based on, so for example, if I tell you, you need to reject that amount of marketing qualified…”

“That's not the right way to do it. If you're doing it that way, then you shouldn't be your co-founder. I mean, like, come on. So you split fifty-fifty. I mean, like, you're going to be doing this for years, hopefully. You're going to make a really big company. Everyone needs to be incentivized from your co-founders to…”

“Like, the value of a network Is it's people? Where are the, where are the drivers? Where are the riders, right? That's the, if we were to steal Uber's database, that's the value. Uber app, we can knock that off in a weekend.”

“I personally believe that CSM should be responsible for driving product adoption, building a customer champion, and making a customer responsible. Expansion will happen naturally, uh, if, if all those three things are happening. Now, what happens is if you give your, uh, CSM a revenue quota, then they are only worried…”

“Agencies are a really shitty business model. Um, it's the easiest business to get into and the hardest business to get out of because once you're in it, And once you have that much infrastructure, we had ten million dollars a month worth of payroll. Think of what it takes to keep that beast alive. Every month, every…”

“To be honest with you, we're not so keenly interested in million dollar contracts because that would necessarily mean that the product would become less appealing to the smaller customers. Right now, the way the market is, uh, we are the leading player with companies with fewer than 500 employees, and we don't want to…”

“digital technology is exactly like those two prior changes. It shifts the binding constraint and the binding constraint is no longer physical capital, but it is attention. Like what are humans paying attention to?”

“And the reason it's not true is because the market-based system for it to work, it needs prices. And the most important things that we could allocate attention to don't have prices, and more importantly, cannot have prices. There is no system that you could construct by which these things would have prices attached to…”

“if you really want to get 30 X revenue or 20 X revenue or 15 times revenue, um, it's hard to do that if you're in like a sales process with a broker. Like if a broker is going out to market, then the strategic knows that, okay, there's a floor in pricing because here's what the, the private equity companies and guys…”

“If you're coming in at one and a half million pre, Then a 50 X return is, is the company sells for 75. Now those kind of outcomes are much more doable and much more frequent than, uh, you know, you, I, something selling for seven hundred and fifty million or a billion dollars.”

“I personally think that's why most angel investors do really poorly at the early stage of, of, uh, tech investing. It's because they don't have enough, uh, portfolio companies in their portfolio.”

“the more inflation that there is, is essentially Um, can be seen as like a wealth tax or something because it disproportionately impacts the, you know, owners of these, these assets.”

“our market's been a very, very good market, but it has taken way longer than people expected. And you can look at the list of competitors we've had in the past, and many of them were overfunded, actually, and that's why they failed, because they tried to get the market, and the market wasn't there. Then they had a…”

“it's almost like it forced us to be profitable, the debt, and that allowed us and forced us to be long-term focused, which again, these are like the opposite things I expected way before all of this would happen. Like I always assumed that, you know, people said profit was bad and profit was short-term. Um, it's just…”

“And like, I think SAS actually can be incredibly, Powerful, um, when matched with debt, because if you understand your unit economics with enough, enough depth, like if you understand churn, if you understand expansion, if you understand acquisition, you can actually model out what, like, what should today's revenue be…”

“Now, the only way it doesn't become a drag on future growth, growth, and it becomes hyperinflationary, is when, logically, governments destroy their currencies, because they can't pay back the debt. But, but, but assuming they have to pay back the debt, somebody has to pay back, taxes need to go up, and taxes going up…”

“So even if you now break it back apart, somebody's going to sit on top and consolidate it back.”

“if you let deflation happen and, and, and let the natural order of things happen, you'd need far less of them. You'd, you'd work less. You would, uh, uh, the, you would follow the trend and you'd be less, less, less work along the, along the trend.”

“venture capital allows you to do is act irrationally in the marketplace, and that ability is what gives you the competitive advantage. Because we have this, this capital, we can do experiments and developments, um, not tied to a more traditional bootstrap model.”

“And by the way, if you want to shore up your balance sheet, you should have to go to the debt or equity markets and get the capital. Like that's how, that's the cost of doing business. And so I don't think we want to get in this world where like corporations believe in the good times, take as much risk as possible,…”

“the whole playbook is during a time of crisis, you wait until the American people's will has been broken. And then once their will has been broken and they absolutely are as desperate as possible, that's when you bail them out. And when you bail them out, it becomes this socialist thing.”

“if the engineers aren't working on stuff that is going to generate a payback within six months, then they need to be reallocated or they're gone. So that's what it's all about. It's all about how do I get payback within six months, and I want to get at least a three times return within 12 months.”

“Productivity was always tied with economic strength, but now we're having non-monetizable productivity, and it began really with the microprocessor. It got cheaper and cheaper, and more and more powerful. So on the balance books, it wasn't producing that much wealth, but in reality, it was changing everything. Now,…”

“So if you take one app, like a MailChimp to send email or, uh, and task management, I would say, 85% of what you have to do to build this app is generic. Generic. Like you need a mobile interface, interface. You need to have a front end with drag and drop stuff, uh, the UI. Uh, you need a backend and you need, uh, the,…”

“It's actually fairly rare that entrepreneurs and VCs are totally aligned, uh, in that entrepreneurs can have great outcomes with five to ten million dollar businesses, and VCs can't, and that's not their model, and the second they get a whiff that something is moving towards that model, it's not that appealing to them”

“There's a lot of great businesses that get, that are sort of the exhaust of the VC ecosystem that get left in the dust because they don't fit the, the unicorn mold. And that's too bad because, because a lot of that value gets lost.”

“Uh, if you have a SaaS product, you need to really keep growing your, your dev team. That's where, that's where the money's going to come from.”

“There's a lot of founders like you that get blinded by the initial, hey, here's a hundred grand or 200 grand, right, that an AppSumo can drive you, but it actually really hurts your ability to build a long-term sustainable business because you then have to go hunt for more cash flow after you use up that cash because…”

“I sort of viewed the first transaction like an exit. And then once that happened, it took a lot of sort of day to day pressure off of my shoulders. And so I could operate in a better way because it wasn't like all of my money in the company. It was like we were partners. And so I had taken some chips off the table and…”

“the people that have started use us for free, and if you think are usually the developers and it's very hard to [754] Mada Seghete: To convert a developer into a paid product because they think they can build it themselves.”

“I wouldn't like that. Cause I think it, it makes it harder to understand what's fundamentally going on with the business. And so the, all that CEO reports in that case is we're net one 30 or we're net one 40. And what you don't understand is that a piece of the business is actually churning.”

“moving from small business to enterprise focus will be as hard or harder as starting your company over. Uh, starting your company in the first place. And, um, it was actually really good advice and, and I've, I've appreciated that because even though I knew it was going to be challenging, I hadn't thought it would be…”

“We are interested in, uh, taking small sips of capital, uh, and, and, and small sips of outside leverage, uh, to, to grow the business rather than, Kind of take the traditional venture capital approach. Um, and, and we want to build a business that is, uh, aligned around, uh, disrupting this business and, and building…”

“one of my big areas of CEOs to think about the fact that you don't want to incent your post sales team on net retention. Let your sales team go sell the upsell. They're the, they're the sellers. You want a post sales team that gets up every day and just because my, my job is to make customers Successful.”

“You know, the most valuable part of it is the product, uh, product division, product management side of it. Writing the code is easy. That's like assembly work. Like, Manufacturing work, right? Almost. It's the knowing what to write and how it's supposed to work. That's the hard part.”

“I learned long ago that, um, entrepreneurs, um, the second time that they start a company after selling, um, they make the mistake of funding their own company because, because now that they've sold a company, they're really smart. And, and there's a validation that you have to go through in getting others to invest…”

“most of the B to B payment industry actually charges for the other side, which is the payable side. Um, we think that that's actually less important. Uh, our sort of point of view is that's a vitamin problem. Meaning, um, you know, it's nice for, for your AP to, to not write a paper check, but that's not super, super…”

“I've always thought that, that entrepreneurs who brag about how much they raised or, or what their valuation are, it's sort of like if you brag about how big your mortgage is, um, it's, it, it feels sort of distasteful”

“It's not necessarily something to be proud of. It just means that you didn't actually generate enough revenue yourself to cover the costs that you had.”

“once you allow your marketing team to start using paid marketing as a channel, you will watch them spend all of their time optimizing that paid channel. And almost no time optimizing on organic.”

“Email a few of your competitors and say, I really need to sell the business to take care of some personal stuff. Want to chat? Leave it at that. This sounds desperate, but that's the point. Your desperate vibes will get prospective buyers to engage in conversations that otherwise wouldn't have happened.”

“If investors are sinking all that money into one industry, they're growing the industry and making it easier for you to find new customers. You turn their resources into your resources when you join the space that they're pouring money into.”

“And oftentimes, you know, you can do, you know, anywhere between 50 and 70% net margin a lot of these businesses because of the fact that you're kind of running them horizontal.”

“As you grow, you know, as you grow a business, one of the things that gets obviously more challenging is, I mean, realistically, the core and initial market, uh, forms, let's say, it's just, it's not going to grow to a hundred million dollar business.”

“One thing we've come to know is that all products, you know, that are pretty good is the small business is going to rely on the expertise of someone they trust and they're going to, you know, and, and, and in any given case, you could argue one product's better than another. It doesn't really matter. It's going to be…”

“there's a leverage limit to what the venture debt people will give you, and then you can generally get more debt from a mezzanine provider, and you'll pay a higher, much higher rate of interest, maybe three or four times what you pay on the venture debt, but you can get even more leverage and less dilution for your…”

“Less than ten million of revenue. And this would be my insight for you. There, there isn't a market to go to. You, people come to us and say, hey, can you raise us capital, right? Can you take us to the market, to the capital markets? Capital markets are for, you have, you know, 27 jiffy lubes. You're doing eight…”

“You've got a business that's doing, say, you know, three to ten million. Private equity aren't interested in them, in that they're too small. Venture, venture capital aren't interested in them, in that, you know, if they're 10 years old, if they haven't hockey sticks yet, they're not gonna.”

“Is what, when you dig deep, what normally kills most mergers, and most synergy in mergers, is they, ah, they didn't, ah, they actually, they had what was called organizational silence.”

“any logo churn number that's greater than 20% per annum is worrying, and it's evidence that you don't have good product market fit in one of your customer segments.”

“the way that you actually manage better performance on a customer acquisition basis over time is by reducing your land and accelerating your expand.”

“A price that isn't cheap because if you sell cheap, you aren't really learning anything. So if there were like objections, we wanted to give like a reasonable price. Price is pretty close to what we would ultimately charge. So if people said no, we'd learn what we're doing wrong.”

“when you grow so quickly, the early customers don't really matter because you're growing like 300 to 400% every year. So like these extra 10% that you're going to get from renewals at existing customers doesn't really move the needle. So you much better off focus on getting them excited, getting the new customers. And…”

“building a SaaS company on the back of another platform that could kill you is a very dangerous thing to do. And my million run rate business died, but I've, you know, there are 10,000,020 million run rate businesses that also died. Same fate, building on the back of Google or YouTube or whatever.”

“By the way, the entire game industry is now a SaaS model, as you probably know, software as a service, because people are now buying either a subscription or they're buying a pay-as-you-go Which is really where the game industry invented it, and the SaaS industry took that concept, which is, it's free, and then you,…”

“as we've learned from the usability perspective and UX perspective, it's oftentimes not really important who you're testing with.”

“Investors are not a great market. I mean, we're very cheap. We don't like to pay for technology and, and, and it's a small market, so it's going to be very hard to build a big company if you're just targeting investors.”

“Uh, by adding a simple button like cancel membership without, uh, you know, having to, to ask, having the customer to ask for, um, for cancel or canceling their account. So that was like, Instrumental in reducing churn because people figured out, hey, we can do it on our own, it's easy, and there's no going back. Once…”

“We never wanted to make our services sticky. The reason why I think that is wrong direction, because the reason why you want to make it sticky, you always say, hey, this customer don't switch to others. I think that's wrong approach.”

“really because there's no business model, it's about, you know, people expect that to be free and it's very hard to make money on that. So It makes a lot of sense as part of a bigger platform. And, you know, now most people don't know this, but Venmo is owned by PayPal. Uh, and, um, you know, it makes sense as part of…”

“Hmm, I would say, uh, stop listening to VCs.”

“the economics of open source really can work, uh, as a business model, as a way to drive down customer acquisition costs if you're talking about infrastructure, but I am unaware of it ever working as a way of, as something that's, that's, um, powering the business model, uh, when it's a business application.”

“So in order for a company to see, like, as an employee of a company that's raised a hundred million dollars in capital, for me to see a dime for my incentive stock options, that company has to exit at 1.2 billion dollars.”

“One mistake I think entrepreneurs make and investors make is they don't try to maximize the supply and demand curve. They just keep trying to drive those price points up.”

“Bitcoin, it's a, um, kind of inevitable that the fees will go up, because in order to stay, uh, decentralized, Uh, Bitcoin has to kind of err on the side of being, um, decentralized, having smaller blocks and having higher fees than to go to other kind of the other route, which is to have large blocks, but having it…”

“the only purpose of a business is to make the owners rich. And so like, I kind of believe that, like if you do that, then it, then it creates jobs, it creates all these other things.”

“the history of most companies coming out of open source projects is that the open source project really suffers.”

“And while most people think these guys invest with the primary goal is to show a big win, the primary goal is not to look stupid.”

“If I give away something like free recording, that's a lot cheaper than having a Salesforce. And a sales force, right? Goes out and sells your stuff because you don't give free, free recording.”

“I think people, the, the LTV number is not a, I don't think it's a good number to focus on. Uh, we calculate it and it's in our metrics and everything, but, um, it's, uh, I think, you know, again, you, you know, you have 95%, uh, logo retention or, or dollar retention. Um, you know, that customer is going to stay with…”

“So we've commoditized, you know, what we do way down, um, so it'd be very difficult for someone to compete with us, because you would really, literally need to have 50 or sixty billion of, of spend going through the system just to compete.”

“You don't want to spend your time educating the market that's not ready for you. Cause that's just paving the, the, the, the, the, the road for the next company to take advantage of that education.”

“what I've noticed is actually that people get obsessed with this, like, uh, year payback thing, because everyone says if you're not doing the year payback, then you're not investing enough in growth, but the problem is, like, it's so easy to do dumb stuff or things that look like they're working that aren't actually,…”

“There's, um, there's inflation, there's salary inflation in the market, uh, companies are responding by increasing quotas, um, and it's just not possible. It's not possible for sales reps to hit their, hit those numbers, and I, and I think that sets up I think that sets up, you know, um, some, you know, some bad juju…”

“economic liberalization has been the, the primary way of reducing conflict and violence around the world, not economic restrictions. In fact, most wars start as economic embargoes and push, uh, push populations into extremism.”

“we found that we could actually charge, and when we charge people, it found that enterprise customers actually closed faster than we were giving away for free, and we were making money.”

“So the miners, they serve the blockchain, and yes, therefore they do have some control of it, but at the end, my opinion is, and everyone will give you some different opinions on this, is that the users are really in charge. If the users say, I will switch to this blockchain or to this Fork of a blockchain. Then it…”

“The open source has to be good enough to get started, good enough, easy to get started and use it, so it will have mass distribution, but it has to get to a point where it's hard to scale it, it's hard to make it production grade, and this is where commercial companies have a lot of leverage.”

“there's almost this force of nature where it's actually really hard to grow the business faster than it's naturally growing because there are these time periods where a hotel company is looking for new technology, um, either because they've bought one of our incumbents, um, and they're stuck in a five-year contract…”

“And so, Q-three of 20 15, uh, was just the tail end of a period when valuations of growth tech companies were inversely correlated with cash burn. The more you burned, the higher you were valued, because there was almost an exclusive focus on growth. Um, now it's about fifty-fifty. It's about 50% on growth, 50% on cash…”

“Like it doesn't, my point is it doesn't matter how many patents you have. You have to out execute in the market to get users.”

“Uh, it's like about dominating the space and maintaining an incredibly low price right now for the industry actually helps keep the competition out. And so yes, there will become, there will become a time where that's the most important thing, but it's just not right now.”

“what these data companies own is the relationship to the revenue. And, uh, so, you know, people make the point, you know, we used to call them data dinosaurs, you know, the companies that have been in business for a long time and have aggregated a lot of data, you know, the actual accuracy of the data is horrendous.…”

“We discovered that small businesses, they don't have mature processes enough to be painful enough to be willing to pay. That's why so many test management tools are free or they have a hard time trying to monetize.”

“So another good example, like you look at matter mark or a H refs, all these companies that provide data, especially the ones that offer an export option. You see this all the time. Login, sign up for the premium plan. They export all the data they need, then they quit. And, and that's like, and they get great value…”

“I believe in copying like hell. Anyone who has an ego that thinks they're going to create something new is never going to be successful, in my opinion, right? Especially, I'll take that, especially in the early phases. Once you're an Elon Musk, you can start thinking about creating whole new categories. But early on,…”

“mental and emotional illness are, don't, Don't make for a good match with the CEO role in a growing company. They are not what the traits that inspire people to give their best.”

“the reality is as an entrepreneur that that is just going to be a huge mistake, right? I mean, it is too many people out there that frankly just dive into one thing, build it, sell it, move on to something else. I get that, but I'd rather dive into multiple things.”

“there's a conspiracy among social media marketers. We tell you it's all about having engaging content because then you try it. It doesn't work. And then you hire us.”

“you don't want to show when someone, when there's a mass shooting, don't talk about it. You're going to spread it. All right. It's a meme.”

“So that will definitely apply where a business is doing over a million ARR, but on smaller businesses we deal with, so our average deal size is around 250,000. For deals at that level, there just isn't the scale, so buyers don't tend to pay a multiple of revenue. Once you get above a million ARR, then absolutely you're…”

“basically in this business, if you're not earning 20% on your money, you're doing something radically wrong.”

“the amount of money that you have to raise to be successful in this space, um, by the time you do a series C is about forty million bucks. That's where you need to go and, and to be successful. That's table stakes for this, for this field.”

“if you have that cash to put down, then you would be stifling your growth. Because you would be waiting to buy your first single property until you saved up every ounce of cash, and you would have no leverage on that deal. The reason income property is so, so valuable is that you get leverage.”

“my hunch tells me people always make more money teaching the software than usually what the software actually makes.”

“There's not that much SaaS in Asia. It's much more marketplace in e-commerce. It's almost, Dust off a business plan from 2002 thousand. Bring it back. And run it in Asia and it's running really well.”

“If, if you keep the bank's risk appetite and build a fantastic product from a text tech and UX perspective, you're still not going to be able to serve the like 70% that we do. You would be declining 90%.”

“Like, and what we always think about in the world of AI, I think there's still a lot of companies focusing on the transaction. So you have an AI voice answering to help someone to buy a burger. That's good and great, but that was what the phone call did before. We are helping really just a little bit. For us, it's more…”

“And I think the one thing which in this world of AI is the reality is also not everything needs to be AI. A lot of the thing is deterministic, right? Like it's, we're now trying to AI-fy everything when there's a lot of workflows that can be actually just deterministic.”

“Stripe has fairly good terms. If you pay them back over a year and a half, if you pay them backwards in three months, time value of money and, you know, actual, and, and what was it internal rate of return for them or whatever, right? Like interest is kind of insane.”

“There is something to be said about you are a better founder, a better person to grow it if you are not eating ramen every day.”

“And the point is the private equity playbook, which is going to be to do cost cutting, to maximize the profit, or to, is something we can apply ourselves. I mean, why would I sell the company to someone who can do and then reap the benefits of our own work?”

“to have a meaningful recommendation, because you can also have recommendations just based on signaling data, which again, you can buy, but to be meaningful, uh, you need to do all this pre-work and data analysis and ingestion into your model to, to generate an alpha.”

“frankly, I look at this as like, we're happy to give away the data because we're always upstream from any use case there. And so like over time, there's always things we can first party in.”

“You never know what the world, we all think that like, it's going to keep going in that direction, but absolutely. When the opportunity arises, like take some off and then continue to roll the dice and have some”

“So when you look at financial services, or you look at utilities, or you look at airlines, um, so many of those contact centers are like, they're still not even migrated to the cloud, right? I think the incentive to innovate is, is much less in these, um, sort of oligopolized markets.”

“We actually optimizing for Google and whatever we do, same impact is happening also in LLMs. So not much specific for ChartGPT. You actually doing exactly for SEO, it have a lot of impact on ChartGPT.”

“The most difficult is to convince a business engine that work in the industry because you have so much learning and, and, and perceptions about your company rather than VCs are just Passing deals.”

“What I actually am saying is, if you're going to go give up control, get, take, Cash as well. Don't give up control and cash.”

“Because I value the equity far more than I value the debts. Very simple. Like, why would you do that if you, if you think your business is growing and your equity is growing, arguably your amount of equity you're going to be giving up is, is far, is worth far more than the money that you're going to be borrowing.”

“Don't try to compete with Walmart, Amazon, and Costco. That's, or if you're going to do that, you need to put Two billion dollars on the balance sheet and you need to make that like a 10 year journey.”

“you would, you would prefer a slightly lesser location that, uh, if you can get kind of that white box that doesn't have a lot of structural work and you can put less money into it and get open faster than getting that kind of prime location if you have to do a bunch of work to it.”

“I think it's perverse to build a company to sell it. You need to build a company to provide good value.”

“So we're finding that if you, if you're putting things onto your site that people can't get in ChatGPT now, that that's helping drive clicks through because obviously if they can just get it in ChatGPT, they've got no reason to leave.”

“So, so I think like, yeah, so I think GTM is like the new, the new moat, you know, like if I had a squad of, you know, 200 sellers, uh, selling our product, I don't care how good your product is. It's hard to, hard to beat us”

“I think we're in an amp it up era right now. You know, like all the stuff that they did, they, they did it in an era that it, I mean, it helped them become who they are. But I think now if you don't do what they're talking about in that book, you're dead, you know? Uh, you're gonna be lost in the sea.”

“even A website with really poor domain, domain rating can have high rating on a specific page. And the page rating is more important than the domain rating because Google actually looks at the page rating first.”

“a few times I saw somebody on top of me on Google search results, and I just picked the query and I did this back links to the URL with anchor text. And eventually I took the number one spot. So that works definitely. And, and that's like, that's the most typical serious work you can do on SEO is to take page by page…”

“You should go crazy with links. So it's almost impossible to, to, uh, make it wrong. Like it's, it's better to have more links than less links as long as those are internal links.”

“Is your user the same as your buyer? They say, no. I say, well, then you don't have a PLG motion on the acquisition side.”

“they wanted to talk about engagement and all these unique things, and I said, guys, nobody gives a shit what you're talking about. That's not how marketers buy the product. People buy on clicks, they buy on CPC, they buy on CPM. Don't fight the tide.”

“So don't gate the thing, I know in your head you're like, well that creates a lot of value. Yeah, sure it does. But build value on top of the value that customers are going to get from you. Right? So don't gate the thing that's going to make you sticky, that's going to make them successful with your product. Never do…”

“I can't tell you how many times I've been in conversations with companies where product doesn't have any go-to-market goals. There's no expectations of driving leads, driving activations, driving opportunities, converting, converting leads. Guys, everybody should be on the same page. They should have the same set of…”

“If you're going to bet on something, bet on it, and put resources against it, but most importantly, if you have just one person, you're not going to know if it was a success or a failure without that, without having two, right?”

“Be really crisp in your mind About why you're hiring a person, or why you're putting somebody into a new seat, right? And what that person is going to do over the next six or 12 months, and be explicit about the goals. If you're thinking about what this person's going to do three years from now, you're thinking way too…”

“getting in software sounds like a better business model, but more often than not, it is not big enough to be a scalable public company or to be a venture-backed business”

“my worst hires were polished executives with Amazon, Google. They would come in, I start micromanaging, they would tell me, I'm a terrible CEO. And then I leave them alone for three months, and they fuck everything up. And then I have to fire them, and I get more bad Glassdoor reviews.”

“You have to dissociate From reality. You're gonna say, I can't do this. We have no AAs. Well, we don't have a marketing budget. Well, we don't have this or that. This is where the genius happens. Pretend you're just playing a game. It's not me. It's somebody else. How would I do that?”

“Hard to build a really scaled business on a two billion dollar TAM.”

“And when we look at the confidence, we're like, but why would we estimate the confidence? If we're so sure this is gonna work, you just do it. The whole point of experiments is you don't know what will work. So confidence doesn't really matter what you think. But the C actually is complexity.”

“Valuation is temporary. Control is forever.”

“And SEO is the math. It's not much creativity there. There is a lot of calculations. There is a lot of analysis, keyword analysis, competition analysis, and then very, very pure calculation.”

“interestingly, when you have a distributed database, you actually have a single point of failure, and now we don't have a single point of failure for any, or every customer has a single point of failure, uh, with backups, of course, but you can't, like, take out our entire customer database.”

“If you're there now trying to figure out how you're going to reinvent how people buy from you, stop. Like, just call it sales, is my advice.”

“the chart that's up here is, is something that I came up with called the strap ratio, which is how much money have you raised total divided by where's the revenue, like, what's your ARR in your business? And I think that, for me, super early on, it's not healthy to be below one when you're, like, trying to invest in…”

“If you plan on only doing two or three podcasts, just don't even do it. You will not. I have very, very rarely seen ROI. I've not only implemented this at two organizations, but I've also helped hundreds of brands get into this motion. You want to do at least 20 to 30 podcasts in one month in a Focused niche.”

“if the trust buys real estate, they can rent, they can rent to live in that real estate. So they're not directly connected. So for example, like, let's say I have my daughter, uh, I'll create an irrevocable trust for my daughter. I'll use the proceeds of sale to buy a house. I'll live in the house. I'll pay rent. That…”

“One of the other lessons, by the way, is if you're asking your board what the company is worth, it's probably not worth very much, and if you want to sell the company, it's probably not worth very much. Companies get, ah, bought, not sold.”

“The biggest thing that you can do To drive up retention is not change your price and is not add a new feature. It is fix your onboarding process to drive time to value.”

“Unless they've got like four customer meetings, five customer meetings on their calendar, every single day you don't need more reps. That's not your bottleneck. It's, it's something else.”

“I would strongly advocate that sales leaders should, should own onboarding.”

“in enterprise software, I think, you know, one of the biggest mistakes CEOs do is you get really big, you get farther and farther from your customers. You create org charts that are completely functional, where you have one CRO, one CPO, so on and so forth. And you get, the decision makers get farther and farther and…”

“You can have two different companies with the exact same metrics, and they shouldn't trade the same. Um, you know, and so you've got to be very specific about what you're acquiring and what you're buying. You know, you can see software companies growing at a hundred percent that trade it three times, and you can see…”

“product-led founders are amazing at building product, but they're very bad at rationalizing product.”

“users, I don't think, will ever give you the next unicorn idea, the next great product idea. They're always like, this is what the other tools are doing. Give me that, basically. Like, I want this use case. Uh, the best ideas, in my opinion, come from your own team, your kind of power users, the ones that are using…”

“90% of the time, if they lose their job, whether they lose it voluntarily, or you let them go, is because of some attitude related issue. Either personality, or because they have an attitude issue, or they can't work within the team, or there's a culture fit issue, or they're unwilling to learn and grow. Things of this…”

“When they're coming in, the performance is going to lag. But over time, their performance is going to exceed the other individuals.”

“In six to eight weeks, you know the person's gonna work out on that. Every single time. Every single time I've had to let a person go, even a year later, I knew within six to eight weeks if that person wasn't going to work.”

“The hardest, I, I think this is the hardest place to hire, because you really need somebody who's done this before. You don't need a newbie. You don't need somebody who's been an AE who wants to be a A VP of sales. So you don't, or you don't need a, a, you know, somebody who's done marketing coordination work or demand…”

“understaffed is better than overstaffed all the time. You know, I, I, I absolutely believe it. And I, I really think that's, that's the way especially startups should be functioning.”

“By becoming customer centric, we are moving, to my liking at least, way too much as a, um, solution integrator, system integrator type of company.”

“in our philosophy, SEO is not an art. If, like, you would compare, if it's more a factory, or, uh, art studio, it's more a factory. So there are just a lot of repetitive processes, which sometimes could be quite boring, but you just have to do that. You have to outreach, outreach, outreach. You have to publish,…”

“it's really dumb to do, like, one-on-one, um, the same week or the same day, link exchange, but you build networks, and then you build circles that, you know, I give backlink to you, you give backlink to someone else, you give a little this, and we do it in circles.”

“I wouldn't try to change the culture. For my experiences, the, the company culture is kind of what it is, and it's really just making the most of it, and trying to get the, the teams that can kind of work within that culture.”

“the emergence of, ah, not just the cloud, but also the API economy, the extreme ease with which you can build interoperable products, was basically taking the world into this massive unbundling cycle, where you used to buy this one kind of monolithic solution that was a sweet solution. Now the better move, the…”

“I believe that founders have three jobs. Sell, corporate development, fundraising. That's, that's, that's what you need to do in life, right?”

“Audience means that they must be selling, your channel partner or potential partner must be selling to your ICP. If they're not selling to your ICP, the likelihood that they're going to be successful is zero, not two percent.”

“we were initially trying to disrupt the incumbents, and so a free offering is always the best way to do that”

“No, man, you should always take money off the table. What are you talking about?”

“I would say 10% is good, ah, is a rule of thumb, minimum. 20% is where I would really put the target at, and 30% is if you think that there are going to be some rough economic times in the next couple quarters, boost yourself up to 30% EBITDA to protect yourself in terms of that downside.”

“So focus on the markets that are early. I would say below ten billion is where I would really go, but if you can get it lower to a billion dollar total addressable market that you think is going to grow in the future, that's where you should go.”

“Next, there's one to three ways to get customers. That's it. Very, very few companies, if you look at their user acquisition funnels, actually do more than three, four, five Significant sources of user acquisition as you see them scale.”

“build product number two at ten million ARR, or below 40% year-over-year growth.”

“Founders will try to self-sabotage. If things are going well in the business, you're gonna do stupid stuff to screw it up. And I think the reason why is because founders really like chaos. The company was born out of chaos.”

“the people that built the business with you, the leaders that sacrificed everything with you, in the trenches, building the company, sometimes they're not gonna get you to the next step. Oftentimes that happens at different points in scale, and it is one of the hardest decisions that you have to make as a founder. Is…”

“Um, and then I think, to a large extent, more luck than skill to get to a hundred million, but it requires a ton of patience, and a ton of persistence”

“one of the key mistakes I see again and again is that founders want to, like, fear creating a board. It's not really a control thing. It's really a head space thing. It's really about creating time with those mentors to kind of like review where the business is now, review your metrics, review your financials, and get…”

“I create the sales culture around that value of we are nice, um, and fairness, and it really creates a different type of sales culture to the, to the, you'll see at other companies. Um, and it really helps us with employee retention, so I think it's really helped the, the, and it's helped with Attracting employees to…”

“when you're bootstrapped and you're trying to run a profitable business, when you get stuck, you have options. And a lot of times, if you're raising VC, you just don't.”

“one thing that I just didn't get before, like, kind of a year and a half ago, is that there are product categories within SaaS that are just intrinsically higher churn than other product categories in SaaS, especially in MarTech. So, the golden goose in MarTech is systems of record, email service providers, CRMs,…”

“I think what's good about AI and those things is it does summarize okay, but it leaves out detail that might be the whole story. Like the details where you really understand. If you just say stuff like, you need to listen more, you're like, okay, I get it. But when you hear the, the details, now you sort of go, oh, I…”

“Unless you're building a rocket ship company, or a hardware company, or a defense manufacturing company, you don't need more than one extra ARR in, in equity capital in order to scale. And certainly not before you figure out what your unit economics are.”

“If we just add a shared account manager, we can take the same product and sell it for 20 times the price. So instead of selling it for 50 dollars a month, we sold it for a thousand dollars a month, and you got a shared account manager and a couple extra features, and that was called iContact Enterprise.”

“often we are a little bit timid. There's a little bit of a glass ceiling in, in the Nordics. We're super good at longevity building businesses, but the burst and the window of opportunity that, that Americans see and that they, they cherish. And hey, I have the opportunity now. We often forget here and thereby it…”

“Failure in the U.S. is a different kind of beast. If you're taking off the football team as wide receiver and you have to go to junior varsity and try to come back to varsity, you're celebrated more if you make it back to varsity because you endure it, you fought, you got back. In Europe, it's, especially in the…”

“But I think also, when you are, you know, when you're not super, super big, I think, like, new customer growth, Is equally, if not more important as well. I, if you do the math, I definitely see, you know, a ramping effect if you accumulate over years. Um, but also I think like new customer growth is equally important…”

“So you start with something that's super scalable and then you go enterprise later. Some people start an enterprise makes it kind of hard to go, uh, super scalable. We, we feel.”

“we thought more bodies equated to more sales when that's fucking not true. That's not true.”

“We come from a point of strength when we say, well, this is what we did with no VC funding. We know we can scale it a lot more. Now, are you as an investor going to bring us value as a strategic investor or like to your connections or your knowledge and so on? Because if it's just capital, we don't need you.”

“It doesn't matter what your sales methodology is. Just roll one out. Right? Which is absolutely true. And i'll show you mine. But if it's, i'm not a huge fan of bant. I think it's a little bit simplistic. But, you know, use bant. It's better than nothing. Right? Use medic, med pick, whatever it is. But you need a sales…”

“The reason that I roll this out is because it's a different acronym, and it forces people to learn different words, and therefore engages their critical thinking skills, right? If they use Medpick at their old company, and the adoption was poor, they're going to be like, yeah, yeah, I know it, I know it. Or they use…”

“the better way to look at this is, is the cost of capital. So, you know, I'm getting 90,000 dollars. I got to pay back a 100,000 dollars. My cost of capital is 10,000 dollars. That's the true way to look at this. And, um, cause there is no term and, and, and, and that's really, really important.”

“when someone, um, starts a company, if someone gives them five million bucks, I think they make poor decisions. If the only way to hire people is through customers paying you on contracts, that means you have to actually build something that people want.”

“But a lot of, in my opinion, raising money, the reason, especially first time founders do it, is it's actually just, it makes them feel better. It makes them feel like they're doing the right thing if they can convince people to give them money. And then they sometimes stick in a bad idea for too much time.”

“So with something like to do desk, uh, doing it on your own with a product like that, it's a big product, a lot of support. Um, probably like 200 customers would be the max you could run at successfully on your own.”

“There are, there are anomalies where that can happen, but for most of the founders that are watching the show that might feel they're struggling, it is user by user, and you really do want to be on the phone. If you're not picking up the phone, trying to get your users If you're not even holding them to get them on…”

“if you have 250,000 dollars liquid in the bank or you have, you know, 2.5 million dollars liquid in the bank, your life really doesn't change too much unless you're just crazy and you want to spend it.”

“everybody's got a different potential, but your physical fitness will limit your potential of your mind. Right. So, so it doesn't matter how many books you read, how much personal development that you chase. If your body's a disaster, if you're overweight, if you're fat, if you're drinking more nights than you're not…”

“the problem with Hellscore is like, it's very much biased, right? In the sense that when you build it, you just build it on top of your gut feeling and very few people can definitely validate it and you need some data science expertise to validate it.”

“what we see is there's definitely a merge between this customer success management system as a separate system, like a separate silo and the revenue stack in general. So we see many companies, once they advance in the development, they establish a revenue function. On top of, like, individual silos. Therefore, these…”

“so if someone who's purchased Zoho is, is showing that they're more cost conscience, they're, they're willing to take shortcuts. They want the cheaper thing. Um, and so it, it, uh, It, they're less likely to purchase add-ons of this nature.”

“we started off with just a flat take rate of, of eight percent. And as time went on, we noticed a weird phenomenon of, of, uh, what they call a graduation rate, a graduation issue where, where vendors will grow with the platform and they're doing, you know, three, 400,000 dollars a year on the platform. And they say,…”

“The other thing we started looking at, looking at, and it's definitely something I encourage all the founders to do, look at microacquisitions. Um, so we used to do a platform called acquire.com, used to go microacquire.com. There's a bunch of platforms like this out there. There's lots of companies there, like less…”

“I still, I still believe, and I know it's unpopular this month, but the growth trumps profitability, uh, right now, especially if you're early in a market and you're, and you're, uh, not at scale.”

“So a lot of companies, what they do is they'll make a startup and then they'll try to find distribution. So they'll start with the product and then try to find the people. My thing is to find the people have fun creating the content and then figure out what product they want. And then build that for them.”

“the testing the water is you're talking to investors, and when you talk to the investors, if those investors don't come back and tell the banks, hey, we're really excited about investing in this, the banks go, eh, I don't think that there's an IPO here to be done. So you're not, you're not just getting feedback. This…”

“When you get a client, you start working with that organization to go into additional verticals for that organization. Now, once they have gone into two or three verticals, that's it. It's game over. They can not leave. And why can't they leave? Because it's not about replacing RegPack for a different software. It's…”

“Months, months. And then they want to meet the founder and they want to like, you know, look at all your books and everything. Like, so it's, it's just like slightly less painful than, than doing a bonafide like venture round.”

“it makes it a little bit easier where it feels like instead of coming from a place of like, I need to start making revenue like as fast as possible because I need to recoup my investment, which is essentially draining from my personal bank account. Um, to, Hey, like we can actually make smart decisions, think a little…”

“the problem in America with college is not getting in. It's getting out.”

“if you, if you really genuinely think that you could build a hundred million dollar business, then you're probably going to want to go out to venture money because you're going to need to raise two or three times. Um, and debt probably won't help you do that over the longer term. I think if you, if you think, and…”

“You know, you cannot judge by, uh, by interview or you cannot judge by reading profile. You know, you have to hire them, take a risk of 30 days, 40 days, assign, see if they are compatible for your vision. That is the only way you can find the talent.”

“I think I like the bootstrap approach. I mean, you could sell the company, have a much smaller exit, but it could end up being just as big or just as good for yourself as like a much larger exit when you've got, you know, all kinds of different classes of prep shares and, you know, uh, some, some venture debt and like,…”

“I built it for Resilience to a large extent, rather than for growth. Right? And, you know, when you, when you do this for years, you learn a few lessons. One is that everybody dies. I don't mean personally. I mean, every business dies. There was the year 2000 when nobody bought anything. It was the year 2008 when…”

“It's not about dropping your price. In fact, you should probably raise yours, but that's a story for another time.”

“I don't want anymore to rely on investors because it creates the wrong behavior as you build your organization.”

“Um, we used to sell the startups in the early days, and maybe this has evolved, but, you know, they die, they churn, they require lots of support, they don't have a lot of money, so it's kind of like the perfect SAS hell.”

“Don't worry about perfecting your tech too early. So again, this one changes with scale, but in the beginning, I remember we used to have conversations about, like, oh, we got tech debt, we got tech debt, and I was like, hey, we don't have any fucking revenue. Like, I don't care about tech debt, right? Like, let's go…”

“Unless you sell developer tools, like, totally useless, right? We would get, we did get there a couple times. Our Google Analytics traffic spiked, and then we just got, you know, a bunch of people who said our product sucks in the comments, so that was fun.”

“don't try to innovate in HR. So your, your focus is to build a product, and your innovation should be in the product.”

“panel discussions by definition are garbage, because everybody agrees with each other, so don't participate in them. They're just, they're useless, For the speakers, they're useless for the audience. It's like a, it's just mutually self-assured destruction.”

“when you're hiring somebody, if you're ever doing a pros and cons list, that tells, that means you shouldn't hire them. Immediately.”

“Uh, 90 days to get up to speed for execs is way too long. Uh, they should be contributing in 30 days. Like, I need to do a 90 day listening tour? That's bullshit. You gotta get in there and get some shit done quickly.”

“Uh, if you haven't, if somebody has never let somebody go, they're not a good manager. Uh, at scale. Like, if you haven't, haven't had the hard conversation, that's a problem.”

“If somebody says no to your offer initially, just let it go. Like convincing them. You're always gonna be, if they do come, you're always, they're always, they're always gonna be wondering, did I make the right decision? You're always gonna be wondering, are they happy? There's already enough overhead in a startup. You…”

“If you are recruiting, and someone comes in and say that they want some kind of C-level position, CRO, or whatever, that's not the person that should get on board. Really important, We have done that mistake. Uh, you will get the person who's not ready to get their hands dirty. So please don't hire anyone on a C-level…”

“First of all, what we have seen working really well is that you have your own internal recruiting team. We've tried external. It doesn't work, at least not for me. Because when we have it internal, they know your culture, they know your business, they know your product, your offering, what's happening around the,…”

“You need to get them signed now. Like, if they are perfect, like, why should you wait the week? What, what are they waiting a week for? I don't know. They just wanted to think about it. What are they thinking about? Get them in and be aligned on this. So this is super important also. Or you will miss the best reps out…”

“not everyone needs to train exactly the same thing. I think that's the original, um, error that you do. You have these boost sessions where you get everyone in and you're training negotiation. But maybe 50% of your team already know how to negotiate. Why spend two hours on that, right?”

“And customer success, by the way, customer success for me is, ah, they are the, the, the, the guys that upsell. So again, going back to that example, you have a product, you partner with another company to, ah, add their product to your offer, offering. Um, who does that? In my opinion, the customer success is the, is…”

“So in a Unicorn, you get a billion dollars valuation. Founders probably end up owning 10% of the company. That's a hundred million. You build a Proficon. You build a hundred million dollar revenue, ah, valuation company. If you own most of it, that's the same thing. And it's much easier to get to fifteen million than…”

“Um, so when you're doing deals, it's worth that extra two, three percent to get the best banker that you can. Makes a world of difference. As founders, we are just unable to negotiate.”

“And if we can shift focus from new customers to existing customers, it opens up a five X bigger TAM for, for brands focused on existing customer relationships. That's really the only way brands can build profitable businesses.”

“Numbers are subjective because we give them meaning. Six million is always six million. That's why numbers are objective, because the quantity doesn't change. But what we believe about it, and the decisions we make because of it, that's the thing that changed, and that's why quantitative data is just as subjective as…”

“And the one place in your company that has the most qualitative data, unfortunately, isn't UX, even though I would love it to be, but like, in UX research, you can't talk to 4000 people in a month, most months. Customer success is already doing that.”

“I like AEs prospecting as well. Until we get to scale, and the AEs are truly back-to-back in meetings all day, and working pipeline, they're also doing activities.”

“there's a lot of value in, uh, taking dollars from less sophisticated investors, because they might be a little bit more hands-off, have fewer opinions on how you run the business, and be a little less demanding day to day.”

“you can have all the best strategies and tactics and metrics in the world, but if you don't do this, you're still going to be limiting yourself, and a lot of these things are not going to mean anything to you. You're not going to be able to use them. Because your unconscious mind, where all of this emotional stuff…”

“when you're stuck in victim, what you're committed to is having unsolvable problems, so fuck anybody try to fucking solve that problem for you, Because you're hooked into this idea that this problem is intractable.”

“Look, if you are in the validation stage, in my humble opinion, it's totally okay to have an LTV to CAC of eight or 10. You better have that LTV to CAC, because you're still selling through founders. You're still trying to create that repeatable sales motion.”

“my, my strongest piece of advice, try to delay venture capital or any kind of capital raise money as far as you can. Um, sometimes it's hard. Um, one way to mitigate that temporarily is, is by selling PS, right?”

“our debt capital, we have both cheap capital and very expensive debt capital. Um, at some point, the expensive debt capital is worse than equity.”

“If someone says, I'm concerned about your CLTV to CAC ratio at a million dollars, you need to wonder why you're working with that person, because it's pretty meaningless”

“When you hit kind of 10 to fifteen million, it gets more difficult to acquire new customers. Why? You've hit the cream of the crop. Now you might be getting those early majority buyers. If you look at the crossing the chasm technology life cycle adoption curve. So you'll see your cap efficiency actually go down,…”

“I've talked to people who's doing 10 cold calls, ah, you know, a week, or 50, like, you're never gonna get to your target.”

“I do recommend that you build your personal brand up, and then you build up your business brand before doing it.”

“And don't build a flat structure. Because what typically happens is when you're in the early stages, like, you know, 10 people, 20 people, et cetera, you try to build a flat structure, right? Everybody reports to you. And it's fine. But once you start scaling, once you reach, you know, That is not going to help you.…”

“it's harder to build a single product, hundred million dollar business. Then, you know, like, it's fairly, comparatively easy to build, like, a 20, thirty million dollar businesses.”

“I've never experienced the idea that by going out and paying, you know, a huge salary, I'm gonna get a 10 X person to come in. All my 10 X, if you like, people who work for me now, who are on good salaries, they all started joining the company at fairly modest rates, and basically worked really hard inside the company…”

“I think only sort of like recently, you know, in the eighth year, are we now, you know, paying top dollar for, you know, senior leadership roles, and we are seeing, you know, personally, like a 10 X difference, you know, in, I guess, uh, these expensive, uh, sort of folks.”

“VCs try to give you too much money because they're basically trying to run down the fund. They're trying to write big checks. If they tell you they're going to give you a million, they're going to try to make you take five million because they're just basically, you know, their, their objectives are different to yours.”

“Category creation. Used to be maybe, ah, a multi-year head start. Now it's a few months. Right? The number of categories, we have three competitors, a vendor here, we've got multiple people in the security and kind of SOC to automation here. So that head start goes, is, is months, maybe quarters at, at most these days.”

“This idea that it is okay to be direct with people and to criticize them when they let you down, but you've got to work on that relationship. But that being too nice is actually ruinous for a company.”

“I'm a big believer that, um, psychological safety shouldn't be measured more than annually, because you need to work pretty consistently to get at the core drivers of psych safety.”

“We recommend you change your prices once a quarter.”

“I can sell without a CRM. I can sell without intent data. I can sell without conversational intelligence. These are wonderful technologies. I can sell without a sales engagement tool. I just need a spreadsheet, and I have to have the contact information for my buyer, otherwise it's a non-starter for anything else.”

“Marketing is almost the same effort marketing in a niche as it is in a big TAM, so swing for the fences and go after a big vertical.”

“If you're an employee at a big company, are you able to swipe a credit card? No, you gotta get budget approval, even for nine, nine dollars a month. So you end up picking up a lot of users, even if your product's not as good, because it's free.”

“What is the feature that all your competition charges for, that people need the most, that you can give away for free, that doesn't cost you a lot of money? That's what you want to give away free.”

“the problem with FinTech is that it's just taking all the stuff we do now and putting a consumer acquisition engine on it.”

“It's the same playbook, it doesn't matter if it's for affiliate, it doesn't matter if it's for SaaS, it doesn't matter what type of business you have”

“on LinkedIn, um, they will throttle you if you're posting many times on your personal page, but they don't throttle you on your company page”

“And hiring my friends with what I thought was the right move or potentially would Um, lead to a disaster. Um, really turned out to be, in my, in my world, a really a great thing. Because these people were really loyal. Um, and they spent time with me over the years. So, it actually worked out well. I know it…”

“if you are a product that has a lot of competition, uh, then something like a high NPS is a pretty good sign of product market fit, because people have a lot of choices. Uh, you need to know that people, like, actually like your product. It's a thing that they want to use. It's a thing they will choose over the other…”

“Kevin's response was, I don't hear enough people complaining about you. If you were making enough difference as a chief security officer, I'd hear more people complaining about you.”

“people are gonna say, oh, I got this two-month project to build a marketing campaign or website, or it's gonna take me a month to ship a feature. And then you do it and you don't even know if it works, 90% of the time. You think it does, but then at the end it doesn't.”

“I can't tell you how many startup, you know, entrepreneurs or wantrepreneurs, whatever you want to call them, keep telling me like, oh yeah, I'm building my product. Well, when'd you start? Two and a half years ago. Okay. You've lost. You've lost before you've even begun.”

“one ratio that I like to look at, this is, this is independently, so this isn't, this isn't from, you know, any particular firm that, that pushes this agenda, but I like to look at it like a, like a one to, uh, you know, one-third on debt and two-thirds on equity.”

“Charisma bias disappears. This is my This is my Captain America story. Basically, if you go into a meeting and you see eight people, I don't even have to hear what they have to say. Usually it's the six foot five guy that looks like Captain America that ends up having his ideas adopted. It's not because he has better…”

“So if you have to have a, a go to market cadence where you're selling a three K product, you can't scale your company.”

“We knew that if we charged by accounts for our SaaS fees, um, we'd leave a billion dollars on the table, because there's not as many accounts as there are locations, and if we charge for user licenses, we'd bottleneck our adoption. Um, but everyone is used to user licenses, so we built it into our model, um, to…”

“I think that there's a lot of opportunity for some type of revenue share for LTV. If you're really able to support a company's LTV and increase that, There should be able to be some point of lift that they're going to lose their LTV numbers if your software goes away. And that LTV is attached to a dollar amount. And so…”

“don't go to, to like, big conferences, uh, trying to sell your product if you're just getting started. Uh, what to do instead? Go for a local meetup. Uh, you will be able to form much more intimate relationship with your customers, area adopters. It will compound over time as well, much better.”

“You should start pricing higher, and not like lower, uh, than your competitors, because at the beginning you are looking for early adopters, they will have higher willingness to pay, so you can just capitalize on this and just get some money to get started.”

“Don't use discounts. Don't do lifetime deals.”

“if you ask them to write a GTO review, they won't do, like, one star, because they would feel bad about it, so they either leave a good review or no. No review at all.”

“And as product differentiation gets increasingly blurred, and competitive pricing kind of almost rules you out of the market, the one reason that you'll win more deals is your sales process.”

“If you demo early, before you've gone through really deep discovery, you're forcing yourself to get embroiled in feature selling, because you're just showing people features. That's what a demo is. The demo should come at the end.”

“The benefits from doing the right thing are very small in sales. The benefits from pulling out really quickly are massive.”

“It's taking your buyer through a process, and not just running the process that your buyer wants you to go through.”

“Look, the best person to sell Your platform is going to be your founder. It is. Doesn't matter if you're the chief sales officer, you're the VP of sales, whoever you are in this room, if you're not the founder, I can tell you the best person to sell your product is going to be the founder.”

“the medical provider networks in the US charge a very high price and internationally medical provider networks have chart have no price, but it's like a majority of the cost of insurance.”

“So having an investment like that over the period of time that you're saying is far more, the cash flow is far better when you're doing an alignment in a sale like this as compared to trying to make it yourself bootstrapping.”

“I'm not hiring people with the incentive of being able to cash out their options. If the company does well, and if a strategic comes along and purchases the firm for a very high price, then fantastic. And then we'll all share in those spoils. But if not, I don't see funding for secondary, um, for employees to be…”

“I would tell most people, if you can't do it in three or four, just quit, give up, and start something new.”

“it, it, it's not a long-term initiative because the people who, who are able to, to, to hit the numbers, they grow tired of this kind of, uh, banging the head against the wall strategy.”

“And the reality is that as a SaaS founder, no matter what people say, you don't have that balance because you have to, you have to focus because it's a short life cycle. And in order to scale to the level, To see the outcome you need to be, you need to be hustling.”

“you never really want to sell your company. You want your company to get bought.”

“Um, and then the, the one time we did this successfully for cheap was with Tapleo, that seven figure acquisition, uh, Tapleo tweet hunter. And that was when the founder was the coder. So Tebow was a coder and we were able to do it. I don't think we had any depth costs. It was just him building it. So that's what I…”