The Wisdom Wall

“This question would have come off as unreasonable for Toby to ask pre-AI, but with AI, the expectation of your team to get more work done with no more or even fewer people is all of a sudden totally realistic.”

“the best product doesn't always win, and product is not a long-term competitive advantage.”

“Organizations are not getting killed by their C players. Everybody knows who they are, and performance eventually is addressed. The people who kill organizations are your B players. It's the scourge of the enterprise, because there are many, and they are generally accepted. Often they are seen as not bad enough to…”

“founders do lie, and founders do embellish, and they do it necessarily to get their business off the ground.”

“I think that every leader should be an expert in what they're leading. There should be no people managers in the entire company. And when I say people managers, meaning your only responsibility is people, not the work or not the domain, because you can't manage people devoid of their work.”

“And I think the obvious benefit that companies get from partnering with a creator or someone who has audience is getting more customers. But I would actually argue that is like the least exciting thing about having an audience, When I think about the value that my audience has provided to StoryArb, sure, it's been our…”

“if you're in a competitive VC-funded space, it is foolish to compete without raising money.”

“There is no moat in productivity. Avoid it if you can.”

“good product with great marketing beats amazing product with no marketing.”

“The shock to the system will be profound, or you are perhaps not taking it far enough. People may squeal, but consider that a sign you are bringing it on.”

“Success begets acolytes who tell you you're right when you're wrong. Worse, you start believing them. This leads down a dangerous path where vision breaks from reality and, likely aided by a fear of failure, Curdles your confidence into a con.”

“I think that the CEO, unless they're not a product person, should think of themselves as a chief product officer, and they should be involved in the product.”

“actually the best business to launch as a creator is something that is completely commoditized. You know, there will always be product market fit for it because humans appetite for it really isn't changing. And so you'll be able to sell a lot of it because you're the best brand or marketer of it.”

“The first secret, quantity over quality. It sounds counterintuitive, but being super selective in an ambassador program doesn't work. Why? Because college students, no matter how ambitious they are, no matter how impressive their resumes are, they are flaky. And the only way you de-risk ambassador flakiness is by…”

“And I find meetings are oftentimes a lazy attempt to get something done. Something needs to be done, and the easiest thing to do is for you to just throw time on a calendar instead of just doing the thing now.”

“Meetings are also not for initial brainstorms. Those should be done independently and then shared over docs or email, and then you can come together to make a joint decision around that brainstorm via a meeting.”

“Doing what I am doing is likely not the optimal choice for most entrepreneurs.”

“the process of talking to angels has reiterated my feeling that you should only raise VC money if you absolutely have to, if you are optimizing for the freedom to pick your path as a business long-term.”

“because for them, they either want a billion dollar valuation, or they don't necessarily care. Like, they'd rather become a zero, versus us Be a two hundred million dollar company, it's life changing for the founders, but it doesn't do anything for the fund.”

“me saying to entrepreneurs that You should never consider throwing in the towel on your business is really dangerous advice to give.”

“And so what I would say is, let's just say you spent 10 hours working on your pitch, working on the story you were going to tell about your startup. I think Probably over half of that time, at least five hours, need to be focused on the way that you deliver the message.”

“Being driven from a place of fear is exceptionally effective.”

“You should have three to seven people in your leadership offsite because you should only have three to seven people on your leadership team.”

“No amount of money can make someone want a job. They need to want it on their own.”

“Outside of the memo, I just love this idea of having to requalify for a job. It may be scary to some, but for the type of company that wants to grow, 20 to 40% per year, it needs to attract people that are excited by growing that fast, and this requalification mindset is a perfect filtering mechanism to weed out…”

“The fact that employees are going to be evaluated based on their AI usage is an amazing idea, and it is one of the only ways you can truly create positive pressure for your team to take the technology seriously.”

“I'll assert that market is the most important factor in a startup success or failure.”

“First, early stage founders are typically really bad customers. They're the most resource constrained. Oftentimes they're the most demanding. And if they don't have product market fit, you are making a bet on their business in order for them to stay a customer.”

“Content will never be a must-have for founders. It is a nice-to-have, and early-stage founders do not have the luxury of time to spend on nice-to-haves.”

“I usually think conferences are a massive waste of time. You spend hours in transit, hundreds or thousands of dollars on flights and hotels, and instead of working on your business, you spend your time, quote unquote, networking or listening to panels that oftentimes could have just been you listening to a podcast in…”

“Which is an absolute shame because it is literally the most important skill in business. I do not say that facetiously. Sales is king of the hill. Without it, your startup will not succeed.”

“the best sellers that I've met in my career are introverts, and they're the best thinkers. They're the clearest thinkers. They're the people who are the most deeply prepared and thoughtful, and so they don't have to use all of kind of like this theater, this sales theater to convince someone to do something, they just…”

“So this is all just further validation that tools like cursor are bringing down the skill level required to create simple software or games to zero.”

“I feel like one of my learnings in building has just been that like, I love building startups, but startups are oftentimes horrible customers. And like, literally by going up market, you can just charge a lot more.”

“the best way to turn a podcast into a business, if that's what you want to do with it, Is not through advertisements, but by monetizing your audience directly.”

“far more entrepreneurs regret selling their business too late than entrepreneurs who regret selling their business too early.”

“Gut feeling, I think, gets undervalued because we live in a world where you need to put metrics to everything, or everything needs to be, like, quantified, or it has to be, like, super thoughtful, and by definition, your gut is not thoughtful because it is not thinking, and I actually think more than ever before, I…”

“every time we create something, we work backward from an emotion, and he said the only thing that people will share are the following acronyms. LOL, WTF, OMG, AWW, AW, or WOW, W-O-W.”

“being naive to an industry is actually a huge advantage, and he gave me reassurance that I could enter an industry that I am, quote, unquote, unqualified to enter.”

“it seems like differentiation does not happen at the product feature level.”

“We don't waste time by making the wrong decisions. We waste time by falling victim to routine and not making any decisions.”

“We lost the war due to inexperience, product myopia, and a lack of capital in a highly capital-intensive and competitive space.”

“bootstrapping works best in uncompetitive spaces or niches or if you have an unfair advantage, i.e., a personal brand, Unique customer acquisition channel, et cetera.”

“LTV and calculating LTV is not a business strategy. It is a way of optimizing your marketing channels. And at the end of the day, LTV to CAC, lifetime value to acquisition cost, is simply just an arbitrage game. It is an arbitrage between what you can pay to acquire a customer through Facebook, Google, paid YouTube…”

“It is no coincidence that companies that put a heavy emphasis on LTV are also the ones that have massive losses as they scale, frequently even through an IPO.”

“And as you spend more and more money to acquire customers, you are going to exhaust The best quality customers, which means you're going to either have to pay more to find good quality customers, or you're going to acquire lower quality customers who are going to churn faster or contribute less revenue to your…”

“when you spend a lot on marketing, you have to charge more for your product to account for having enough margin such that you're able to spend on marketing while having a, you know, good profitable product. And so that means when you spend a lot of marketing, You hurt the customer because you're going to have to charge…”

“being macro correct about an industry Is more important than being micro correct, especially as an investor, but also as an entrepreneur.”

“I think the reason that most leaders do not quote unquote amp it up is either because they settle into and get comfortable with a lower than exceptional standard that just becomes the norm for them, so they don't spot what exceptional performance looks like, or leaders And Frank will talk about this in a minute, are…”

“In tech, value is a function of growth, so we ran our companies for growth, period.”

“But no matter how much you love what you're building, I do truly believe everyone has a price, especially if they haven't yet hit their financial freedom threshold.”

“When founders say they don't have an ego around being an entrepreneur, I generally think they are lying or they aren't self-aware enough to know that it is a large subconscious driver of their behavior.”

“In fact, I believe the best way to succeed is to close off as many options as possible once you have high conviction in one thing.”

“What this means to me is that the most original people are never those that are trying to be original, and in fact, I think there's a core formula of attributes that ironically can be imitated that lead to unintentional earned originality.”

“Delusion is defined as a, quote, false belief or judgment about external reality, but I actually think you need the exact opposite of delusion as a founder. I actually think the best founders prove that the rest of the world is delusional, stuck in their ways because of some story they have about how the world works,…”

“A vision that's not widely derided likely isn't much of a vision.”

“Promising something that doesn't exist is as central to the Valley ethos as late night coding sessions, hoodies, and the hallucination that the public has asked you to solve the world's problems versus just do less damage.”

“the extent to which something is fraud is basically What is the possible damage that is created by not telling the truth?”

“Swarming anyone who questions the narrative is a built-in feature of stocks and sectors that have gotten too far out over their skis.”

“All else being equal, the fastest company in any market will win. Speed is a defining characteristic, if not the defining characteristic, of the leader in virtually every industry you look at.”

“The key takeaway when a decision is made is much more important than what decision is made.”

“There are decisions that deserve days of debate and analysis, but the vast majority aren't worth more than 10 minutes.”

“There's not always a stark tradeoff between something done fast and done well. Don't let you or your organization use that as a false shield or excuse to lose momentum. The moment you do, You lose your competitive advantage”

“I believe you either need to be great at sales or great at building software if you want to build a great business today.”

“I generally agree with this, but I would say studying the beliefs and behaviors of business greats through biographies, autobiographies, like the writings of proven Entrepreneurs and founders is a worthy activity, but only after you step into the arena yourself and have the experience of building a business yourself.”

“Performance marketing, though, doesn't create very good accumulating advantages, because it's not an investment.”

“the problem with finding a negotiation between how you want to run a company, the people you want, Is that's a good way to make everyone miserable? Because what everyone really wants is clarity. What everyone really wants is to be able to row in the same direction really quickly. And also, if you try to appease…”

“And I think, I think there's a difference between micromanagement, which is like telling people exactly what to do and being in the details. Being the details is what every responsible company's board does to the CEO. It doesn't mean the board is telling them what to do, but if you don't know the details, how do you…”

“I would make sure that you have engineering and design ideally report To the founder, product-led person. I would not have design under product unless you have an extremely good reason the product person kind of is a designer.”

“With finding customers, you're going to acquire customers in the early days of your business, and actually, one of your hardest but most important jobs is say you get your first a hundred customers, maybe only 10 of those first a hundred are going to be truly the right customer. The obsessive customer whose problem…”

“Second, the only thing that typically goes down during downturns are valuations. Typically, users, usage, and dollars spent actually go up.”

“Worry less about the economic climate, and if you have to raise capital, don't be dilution sensitive. Get the capital you need, and be success sensitive.”

“Even the wrong focus is better than being unfocused.”

“I actually think that this concept of default alive or dead is as valuable in kind of the pre product market fit phases of your business before you know that there's a, they're there as it is in the post product market fit phases.”

“This is the definition of blitzscaling scaling popularized by Reid Hoffman, and it is not at all what 99.9% of founders should expect or aspire to have from their business.”

“A good business launched at the right time will always beat out a great business that has launched at the wrong time.”

“the only way to build a high growth, sustainable business is for word of mouth to be your greatest engine for new customers.”

“A huge failure of entrepreneurs in general, especially in the early days of their business, is to set unrealistic expectations of what the work or the culture is like because they are afraid of scaring away employees. Bezos takes the complete opposite approach. He wants to scare people away. Because what's left over…”

“This is just a reminder that there's good reason to believe that market is more important than people or even product when thinking about the potential for success of a business.”

“for large companies or just companies in general to build great brands in the future, it is not going to be by focusing attention on building the brand as in like the company. It is going to be by focusing attention on building up people who are representatives of the brand, meaning executives and employees themselves.”

“Sometimes the most extroverted outspoken people are also the worst employees because they're great interviews and But horrible workers, and they get through their career via bullshitting versus actual substance.”

“I believe that this risk of endowment effect causes far too many CEOs and founders to continue running their companies past their point of incompetence.”

“what's more powerful than governance is trust, is loyalty. It's, in a way, fandom from your people.”

“Number of co-founders you have actually is probably the largest lever of what your equity is worth at the end of the day.”

“I also think purely marketing driven creators have to be compared to any other paid marketing channel, like Facebook ads, LinkedIn ads, Snapchat ads, et cetera.”

“if I meet someone who is, let's call it desperate and wildly smart, I would bet on that person every day of the week to succeed.”

“So I actually would be more protective of my idea when talking to investors because I would say they have more layered agendas than someone you just tell about on Twitter who's an individual who's interested in entrepreneurship.”

“I would take two B-plus players that have a deep friendship over two A-players that are complete strangers and Every day of the week.”

“Give your co-founder a lot of equity. And third, don't split your equity, 50, 50.”

“And I would say historically ghost writers could only service maybe three or four clients. And I want to create a more automated process such that ghost writers can service 10 to 15 clients and the quality of the content doesn't change at all. And to me, you do that through someone serving as an account manager, you…”

“if you're looking to bring people in office, his view is there should be two reasons why you bring people in office. Otherwise you should be fine with remote. The two reasons to bring people in office are for trust building and collaboration, and that's it.”

“the way that I've always thought about it is if you were to build businesses as dictated by the way that VCs are taught to think, you would just permanently build enterprise level B to B SaaS businesses over and over and over. That may be right for some people, but it's not just like going to maximize enjoyment and joy…”

“Every good experience you have has a return on investment because of the memories associated with the experience, and so the earlier that you have great experiences in life, the longer that these memories will pay dividends over time”

“The sixth lesson is that the optimal time to extract enjoyment from your, from your money is 26 to 35. And the reason 26 to 35 is the range is basically it's a point in your life where you've potentially been able to save up a little bit, but you're also still young enough to fully enjoy the benefits of your money.”

“He also argues that's the best time to give to your children when they're 26 or 35. Because his view is that it's the point at which they can enjoy the money the most, uh, or the benefits of your money the most, but they can also be fiscally responsible with the money that you give them.”

“the people we thought would do best as ambassadors, the people who were most connected in their student body, who were in five different clubs, who were You know, student body president. They were actually the worst ambassadors because they were spread so thin between so many things.”

“an inherent embedded risk to Silicon Valley bank is it's implied in the name. Like they've always been considered the bank of founders, startups, and VCs. And so like, there's actually a ton of inherent trust risk baked into that because it doesn't take long for that customer base to, to be thinking the same exact…”

“Meetings are also not for initial brainstorms. Those should be done independently and then shared over docs or email, and then you can come together to make a joint decision around that brainstorm via a meeting.”

“I generally believe that it's easier to build a B to B business than a B to C business. Um, I generally believe that getting businesses to pay for things is easier than consumers.”

“if you don't get anyone to dislike you, It probably means that you're accepting trade-offs that probably aren't worth accepting in a business.”

“biggest lesson, or one of the biggest lessons I learned is you can't hire HR early enough, or like, you can, but I would just say, like, when we hired HR, it was too late. It's one, it's one of those things that you're never gonna feel like it's the right time, but if you hire a great HR person early, A lot of these…”

“A nice thing is that I would say usually 10% maybe of people in the business drive 90% of the outcomes in the business.”

“My, my view on slides when you're pitching an investor is it's a lot like a job interview. You don't want to stand out in either direction. You don't want to be the person that shows up like a schlep with, you know, uh, baggy pants and a belt that's off centered.”

“And second, and I think this is the biggest risk, some creators, especially really big ones, they have so much shit going on, and they like the idea of building a business. And making money off that business more than the actual work that it takes to build that business.”

“Businesses with network effects are generally winner-take-all markets, which means that finishing second as a two-sided marketplace is generally a recipe for failure.”

“there's a world in which actually, like, you really think about the trade-offs of your full-time job and your part-time job, and you may actually be an A-minus employee instead of an A-plus employee in order to give yourself the possibility of doing what you really want to do with your part-time side hustle and turning…”

“So simply put, anything that goes wrong on your team or in your company is a result of your failure as a leader, full stop.”

“I traditionally have been so skeptical of partnerships because I found that they are a huge time suck, and very few of them are actually fruitful.”

“employees would actually be really pissed if they were issued stock or stock options by the business, if the company had no interest in selling, and so basically employees would be holding onto stock for 30 plus years with no way to turn it into cash.”

“Growth hacking does nothing to benefit your customer, And therefore is unlikely to be a long-term viable strategy for scaling your business.”

“society has long encouraged specialization over generalization, but the more time I spend in entrepreneurship, the more I believe that becoming well-versed in many things Is more valuable than being an expert in one thing.”

“A layoff conversation should be 90% manager talking, 10% employee. There, unfortunately, is very little upside to making it a more balanced conversation.”

“Rule number one, it should never be a surprise. If an employee is surprised when they receive the news, they're laid off. It is your fault.”

“I have found that reference calls are generally not incredibly enlightening, but they're almost as much a Barometer of the quality of the reference as the person that you're doing the reference call for. Meaning if you believe that people are a reflection of the five people around them or the people closest to them in…”

“And finally, meetings are not for status updates. Those should be sent via email. If people have questions on the updates, those can be answered over email as well. And if questions on the updates turn into a debate that leads to an important decision to be made by several people, that is when a status update can turn…”

“I don't think that it is inherently a bad thing to think about throwing in the towel on a business, because if you don't do that, and you're working on a business that has no hope of working out, you can end up spinning your wheels way longer than you should, and the opportunity cost of not having an openness to kind…”

“at the end of the day, when you are raising a pre-seed round, I'm going to say this over and over, but an investor is investing in you more than they are investing in a business. Because the odds that the business you are pitching right now Kind of the pre-seed stage will be the business that ultimately succeeds or…”

“lack of self-awareness is one of the most dangerous traits in founders because when you don't have self-awareness, Uh, you have tons of blind spots, and you don't know when to hire people or change course to uncover or fix those blind spots, and because at a pre-seed stage, like I said before, a founder is likely going…”

“I actually think the number one way to demonstrate deep thoughtfulness and self-awareness is to basically proactively answer an investor's likely questions.”

“This idea of employee advocacy has been around for a long time, but I've always felt like it's kind of fallen flat or it hasn't, um, gotten enough momentum or hasn't had enough staying power. Because companies that try employee advocacy programs don't have the right culture or set of incentives to unlock employees as…”

“I think that limiting yourself to one round and let's call it 12 to 18 months of cash to figure out your product and get to product market fit and then be default alive is a very healthy constraint that most entrepreneurs would benefit from.”

“I find that limiting beliefs attach themselves to the things that are most identity-provoking to you. Said differently, a limiting belief is something that, if true, would risk your entire identity, and your identity is how you try to make sense of your value and importance in the world.”

“First is you must have one person leading and managing each major function. If you try to make more than one person responsible, no one will be responsible, so pick just one.”

“Most companies are dipping their pinky toes in right now, and when you ask yourself why so little, the answer is because that's what's comfortable. Add inefficiency here, tell a friend you're AI fluent there, post on social about how AI is a game changer, or All without having to put in the work to re-scaffold your…”

“Non-technical people Can now scrap together prototypes and V-ones without knowing how to code, and cracked engineers have the leverage of a full team without needing a full team.”

“Basically, the vision is to make high quality content creation as low friction as humanly possible, which in my humble opinion means keeping the expert in the equation, but only in the steps of the content supply chain that are absolutely necessary.”

“the speed to create most software products, if you have a great engineer using AI, has been shortened to days or weeks instead of months or quarters.”

“My theory is that to win with a product like distro, we will need to win with speed, taste, distribution, and data.”

“And then the third step in the process was to actually secure paying customers before doing anything else. No website, no customer pitch deck. At the time, I hadn't even incorporated the business. All I care about is proving that people are willing to pay for this, and then the other less important stuff comes later.”

“Expert opinions are safe for now. Entertainment is safe for now. Unopinionated research is toast. The bar for standing out is so much higher today, and the way to stand out is by being uniquely human with your content, which means flexing your voice, flexing your opinions, and flexing your taste.”

“I always say that B to B is five years behind B to C, and influencer marketing is no exception.”

“Bad sales is icky. Because bad sales doesn't feel mutually beneficial, and it feels like aggressiveness is compensating for underwhelming value.”

“Being a B plus seller of an A plus product is a hell of a lot better than being an A plus seller of a B plus product.”

“I've generally found that every agency feels a general incentive to move up market, because as you move up market, your deal sizes with larger customers are bigger. Larger customers also generally have more budget and more resources. They're more responsive. They're candidly less of a pain in the ass.”

“At a time when the cost of building products drops significantly, while the cost of marketing continues to rise, having trusted distribution becomes more and more of an advantage.”

“Adjusting your sales or your marketing strategy is the easiest. Replacing the wrong people isn't easy, but it's within your control. The same thing with where your boat is pointed. A change in strategy or vision is painful, but it's within your control. And fixing your boat, the product, takes a lot of time, but if you…”

“The wind, which again is your market, is the most important factor that determines success with your business, but you cannot control it.”

“They would say that they learned a ton from us, they saw the value of building an audience online, but one of three things wasn't working for them. First, they didn't have the time to show up for interviews so that we could get content from them. Basically, they were too busy and other priorities had picked up in their…”

“First of all, I realized that it was almost impossible to think of a worthwhile topic every single day of the week around startup lessons, even if I was in the thick of building and running a business.”

“And so I think my general view on co-hosted podcasts is the best co-hosted podcasts are with people who already have years of rapport before launching the podcast, and I think you have to do it in person unless you are just, like, the greatest at building connection digitally.”

“as more and more content is created online, the cost of searching for what is truly the best content for you as a listener or a reader goes higher and higher, which means that Tastemakers and curators are going to have increasing amounts of premium put on their skill sets because people don't want to spend a ton of…”

“with podcasts, as I'm going to talk about in a minute, where it is a long game, and you have to be willing to do this thing for five plus years if you really want to reap any of the benefits monetarily, from a network perspective, reputationally, etc.”

“I just think podcasts are generally a bad place to create a kind of one-stop shop hub that acts as, like, the curated destination for a deep interest of yours, in this case, entrepreneurship.”

“Having built-in distribution is so important to be successful with podcasts because discoverability, as in people searching and finding your show through the major podcast players like Spotify or Apple, is incredibly bad and difficult.”

“chapter two of building a business, which goes from the job of being a CEO is achieving product market fit to the job of being a CEO is Building a company. Like, actually building an organization that allows you to grow beyond a single product and be around for a long time.”

“Most entrepreneurs don't run their businesses for 25 years. Those people who were on my Mount Rushmore were literally the exceptions to the rule, not the rule.”

“when you are in the process of doing any sort of M&A with your company, whether it's selling your business, acquiring other businesses, or even, like, just doing a Traditional fundraise. It becomes anywhere between, like, 50% to a hundred percent of your job, unless you have a dedicated corporate development or M&A…”

“And I would actually say, very interestingly, the Move out of the CEO role was far more difficult, uh, and far more emotion and identity provoking than was the decision to sell the business.”

“On today's episode, I'm going to talk about how we got from zero subscribers when we first started Morning Brew to 10,000 subscribers, which I would say is roughly the point at which you can actually start making money off an email newsletter.”

“So a hub is something, a digital channel or an in real life channel that gives you, uh, leveraged access to a lot of spokes. Spokes are your, the ideal customer you want to get in front of. Again, we didn't think about it in this way at the time, but it's how I think about everything now. And the reason is, is because…”

“The first time we tried an ambassador program, we went for quality over quantity. So we took a bunch of ambassador applications. We only accepted like 10 ambassadors, and they were the people who were like the best students, involved in the most business clubs, like the people we thought were like the super connectors…”

“And so ultimately, where we shook out is the best possible ambassador program is this hybrid we did, where we let in Like, we made it a quantity game, so we let in every ambassador, but a lot of it was automated until they proved that they provided good work and actually were getting people to subscribe to Morning…”

“The most successful marketers are incredible at inserting themselves into culture in a way where something is in the zeitgeist, but it hasn't been called out yet. Great brands recognize the thing that isn't called out, and then they insert themselves into it.”

“The next one is one of the best ways to stand out as a startup. The short form video is to sell people on your story versus your product.”

“Patty Galloway shared a few of his biggest lessons around YouTube right now, and two things he said are he thinks there's an opportunity for bigger companies to play on YouTube, and one of the best ways to play on YouTube as a bigger company is to latch onto great creators by giving creators access to your company's…”

“Anything that is central to your core competency as a business is something that should be full time.”

“At any given moment, in any given story, the hero of the story has to have a very clear intention, as in what do they want, and then a very clear obstacle, as in who is in the way. And if you are watching a movie or reading a story, you should be able to stop at any moment and be able to name what the intention of the…”

“I do not care what people say that they don't focus on impressions, focus on engagement. That is bullshit. Everyone who creates content on the internet wants Ask more people to see their content. Otherwise they would just be creating content anonymously, pseudonymously, or not publishing it at all.”

“First of all, the more you feel a personal connection to a problem, I believe the better you are going to be at solving that problem because I believe you'll always have this, like, fire burning under your ass For a longer period of time. Like, I just think it's such a long-term propellant if you feel a personal…”

“as they think about taking any sort of quote unquote leap of faith into building something is it never feels clear. It never feels clean. It always feels messy. And when you make the decision, whether it's to start a business, whether it's to go all in on a business, whether it's to quit your job, you never know in…”

“one of the biggest challenges with StoryArbor, or just I would say personal brand businesses in general, is retention. I think it is generally very hard to keep clients for a long time. When I say a long time, I'd say anything more than 12 months if you're solely offering executive social.”

“the first 10 employees in a startup. You should be able to look at them and say to yourself, I think this person will do incredible work for us for a number of years, but ultimately I could see them starting a company of their own.”

“every company has its core competency, and for its core competency, it has one role that Is most important to deliver on that core competency. At Beehive, it's a full stack engineer. At Morning Brew, it is, it was a newsletter writer. Now it's, you know, writer or creator. At StoryArb, my personal branding business, it…”

“the feeling of excitement you get when the world rewards you externally for these quote unquote wins, not only is it quickly disappearing, but also every additional win you have after that first win decreases in how much happiness it brings you because you become desensitized to the feeling of the win.”

“Spending all of your time doing stuff that you don't like because you think more money or more prestige down the road will be worth it only guarantees that you spend all of your time doing things that you don't like.”

“I think one, because it's basically paid R&D to figure out what you want to build outside of just the agency, and they're great for cash flowing and you don't need money up front, but to Andrew's point, they are extremely difficult. Any client service business is extremely difficult.”

“And by the way, this is the way that businesses typically die. It's not one spectacular implosion. It is cut by cut that slowly bleeds out of business, but because they are small cuts, you don't realize how big of a problem they are.”

“In a lot of ways, I believe LTV and the obsession with marketing metrics like this is what has given the rise to more quantitatively focused growth marketers, a role that has replaced creative, more qualitative marketing manager roles at Silicon Valley startups.”

“Now, LTV does have merit, and it is a helpful proxy to prioritize your marketing and understand the economics of each customer that you acquire, but if relied on entirely, It can be misleading at best and extremely harmful to your business at worst.”

“Consider that most companies limit any affiliate fee they would be willing to spend to five to 10% of sales. Yet, when they are marketing, they use different math. They use LTV math. And all of a sudden, it's acceptable to spend 30 to 50% of revenue on customer acquisition.”

“Frequently, the same group that is arguing for more spending is the same one that owns the LTV calculation. This is a mistake. Finance should monitor LTV.”

“If you have organic customers, they shouldn't be included in the spend calculus. They would have arrived regardless of spend.”

“Also, many people discount revenues rather than marginal cash contribution. It is critical to bundle all future variable costs of supporting the customer in order to fairly estimate the future contribution.”

“Organic users typically have a higher NPV, a higher conversion rate, a lower churn, and more satisfied than customers acquired through marketing spend.”

“And generally the best way to think of creative ideas for acquiring customers is when you feel like your ass is against the wall, when you feel like there's scarcity and you have to do clever, scrappy things to acquire customers.”

“Companies need a sustainable, competitive advantage that is independent of their variable marketing campaigns. You can't win a fight with a measuring tape.”

“And the TLDR here is that you want to niche down your content an uncomfortable amount. Productivity as your content circle is too broad. Productivity for professionals is too broad. Productivity and test-taking strategies for medical students in the UK is a perfect starting niche.”

“But overall, it's been proven that software businesses are fundamentally better businesses on average from a unit economics perspective, and even today, like in 1999 and 2011, There are just bad software businesses, just like there are bad media businesses, professional service businesses, or any other type of…”

“It is interesting to see that even with software eating the world, record labels have continued to wield a ton of power that has taken away leverage from software businesses in the space like Spotify.”

“Likewise for FedEx, which is best thought of as a software network that happens to have trucks, planes, and distribution hubs attached.”

“Is how startups and private sector companies are getting involved in this space today through vertical integration where they are building both the hardware and software. So I think about that with and a role for defense tech or Varda for space tech. And then the government is starting to partner with these firms in a…”

“A counter position business adopts a new superior business model that incumbents cannot mimic due to the anticipated cannibalization of their existing business.”

“Once you rely on Salesforce's CRM, it's often not worth switching platforms. It can take months to retain your workforce and cost hundreds of thousands or even tens of millions of dollars to recreate business logic on the new platform.”

“This is a big reason for vendor lock-in and why enterprise software can be terrible, overpriced, and have outdated UX, but still succeed.”

“Now, I will say that unlike some of the other powers, I do think brand is the one that takes the longest to build up, even with the acceleration of technology. I do think there's a max speed that trust and word of mouth spread can happen at, and it looks more like decades than years.”

“Quicking the pace also drives a narrow focus. You simply can't move very fast when you're pushing on too many fronts at the same time.”

“After reviewing the early growth strategies of more than a hundred consumer companies, it turns out that there are really only seven reliable ways to find your first 1000 users.”

“Note, almost every startup finds the vast majority of their early growth from just one or two channels.”

“The typical path to first 1000 users for consumer startups is one of three things. First, reach out to friends and colleagues. Example, email them, post on social media, or call them. Second, go where your target audience hangs out, online or offline. So for example, forums, product hunt, college campuses, Craigslist,…”

“if you're a marketplace or platform, for example, DoorDash, Cameo, Substack, there's three proven strategies for this archetype. First, reach out to targeted strangers. For example, DM to celebs or email owners. Second, get physical placement. For example, stickers and flyers. And third, enable your supply to drive…”

“there's two ways to get customers for any business. You either have to go one by one, or you can leverage what I call the hub and spoke model, meaning you find a hub and that hub can be an influencer. It can be a community in person or online. It can be some sort of social network. Basically, you find something that…”

“The further out from the center the founder gets, the harder and less likely to succeed these strategies generally are. So in your decision of where to start, start with the easy stuff and migrate outward if nothing is working.”

“Selling a business is not glamorous. Few founders talk about this largely because they're afraid of Complaining about quote unquote champagne problems, but it is a challenge that people experience nonetheless.”

“On top of that, unless you immediately leave your business once you've sold, your life doesn't really change after the exit.”

“A movement from left of the freedom line to right of the line changes your life fundamentally, Giving you the freedom to do whatever makes you happy forever. If you're crossing from left to right, it doesn't matter how far to the right you go. Sure, a hundred million is a different lifestyle than ten million, but it's…”

“In practice, phase two usually begins when a startup has around 20 to 25 employees and ends when it reaches 400 to 500 employees.”

“It's better to act quickly and leave a void in the organization than to leave an ineffective senior executive in place for too long.”

“From personal experience, I can tell you that getting 75% of your executive hires right is actually incredible, and it's more likely that you'll bat fifty-fifty if you're a first-time founder Who's building a leadership team for the first time.”

“his definition of culture is that a company's culture Is a fifty-day moving average of your actions and your company's actions, and I love that because it is all based on behaviors and not some words that are written on a wall.”

“The single author approach usually fails because the resulting words are often disconnected from the reality of how the employees as a whole experience the company.”

“Reaching the point of having a lot of unscheduled think time is perhaps the clearest sign of success for a phase two CEO. It suggests that you've hired a leadership team, delegated the day-to-day activities to them, and codified mission, strategy, and metrics well enough for them to operate effectively without your…”

“Building a business is no different. If you add seven percent more customers each month, improve the product by seven percent each month, improve your people by seven percent each month, your business will be exponentially better in the long term.”

“I think big ideas are the greatest recruiters. Smart, ambitious people want to work on big, ambitious ideas. Sure, Elon Musk or Sam Altman can attract any top one percent employee, and especially an engineer, because of their reputation, but I believe just as important as the founder, even if it's someone as big as…”

“there are no participation trophies in startups. That's my view on it. It doesn't matter how hard you work or what work you do. If you don't hit the goals that you've set for yourself and the business, that's what truly matters.”

“That is also why when you're in hiring mode in the early years of your business, unless you already have a management layer or an executive team, you or one of your co-founders will probably have to spend something like 50% of their time exclusively recruiting and hiring.”

“Fast iteration can make up for a lot. It's usually okay to be wrong if you iterate quickly. Plans should be measured in decades. Execution should be measured in weeks.”

“It is uncomfortable to hire people that are better than you. Your survival brain kicks in at first, and you worry about your job. You worry that these people won't learn from you. You question your value. In fact, all of these things, all of these worries, are a sign that you're actually hiring the right people.”

“If I look back at my one big career win, Morning Brew, there's really nothing original about it. Business news has existed since the 1700 and email has been around since the 19 seventies. And that is exactly why it worked. We did something that we already knew there would be foundational demand for. Our real genius was…”

“I think what allowed us to be different is that we didn't assume any quote-unquote industry truth to actually be true until we verified it for ourselves.”

“First of all, copying isn't bad, and everyone does copy, but I think the more powerful version of imitation is far imitation, where you can make something unoriginal original and Simply by transporting it across contexts. Foreign imitation can happen cross field, cross generation, cross customer segment, cross content…”

“And of course, the great irony of this whole essay, an essay that is focused on imitation and innovation, is that neither of these things should actually be the focus of the entrepreneur. Rather, the focus should be on finding the truth and building the product that leads to the best outcome for whatever it is that…”

“It's also why I think the perfect entrepreneur is a default optimist with low-grade paranoia because if you are a cynic or a pessimist, you will find every reason to not start a new business because, frankly, every new business idea has flaws that would give you good reason to never launch the thing in the first place.”

“The visionary narrative is a self-perpetuating machine, a flywheel of storytelling, capital, and the future that capital can pull forward, which buttresses the storytelling, and so on, and so on.”

“You know you're going fast enough if there's a low-level discomfort, people feeling stretched, but if you're going too fast, you'll see it on their faces, and that's important to spot, too.”

“All it takes is asking the simple question, why can't this be done sooner? Asking it methodically, reliably, and habitually can have a profound impact on the speed of your organization.”

“The untrained mind has a weird way of defaulting to serial activities, i.e. I'll do this after you do that after XYZ happens. You want people working in parallel instead. A lot of people assume dependencies where they don't even exist.”

“This is how I learned that if you can knock out big chunks of a project early, you can reduce the overhead of the remaining parts by 90%.”

“The one I see the most, and this includes at Google too, is that people hem and haw over what the founder or CEO will think every step of the way. Just get their input first. Don't get your work reversed later on. What a founder might think is classic cognitive overhead.”

“This is especially valuable for startups who may not have every feature or bell and whistle that older competitors do, but oftentimes the feeling of speed and momentum will convince customers to risk it on a new player if they believe that that player's speed will close the product gap quickly enough.”

“Newton taught us that an object in motion stays in motion, and an object at rest stays at rest, and nowhere does this feel more true in your bones than when you're running a business, which is why I think one of your most important jobs as an entrepreneur is to focus on creating and keeping momentum and doing…”

“If you find something that is true in more than one field, you've probably uncovered something particularly important. The more fields it shows up in, the more likely it is to be a fundamental driver of how the world works.”

“The differences in outcomes among people with the same formal education are enormous, and a big reason why is that some people find the time to value passive learning, and others don't.”

“Basically, he says with any new technology wave, there are two phases of innovation, the skeuomorphic era and the native era. The skeuomorphic era is generally a copy and paste of existing behavior. So the early internet was mostly a digital adaptation of pre-internet activities.”

“The reason big new things sneak by incumbents is that the next big thing always starts out being dismissed as a toy.”

“Disruptive technologies are dismissed as toys because when they are first launched, they undershoot user needs.”

“my view is there's a three-step thought experiment that I think most people should go through To think about building wealth through a business over the long term. First question, you should ask yourself an answer. What are my one to two unique skill sets that I'll never delegate from myself? Second, what are the one…”

“I've always said that the health of an organization, one simple heuristic is how close there's engineering and marketing.”

“And because no one's marketing new things or shipping, there's no purpose to ship new things because you ship new things and people don't know about them or use them, or they're not educated. And so you try these big new things, People don't adopt them immediately, so then you get more and more incremental.”

“I think one of the most important things for a founder or leader to do is set the pace of the team. I think the pace of the team is one of the most important things you can do, and that pace is sometimes governed not by how hard people work, but how decisive they are. If you want to improve the speed of a company, then…”

“I think that a lot of people are afraid to reach out to help because they think other people are busy. The biggest honor most people get in their lives or one of the biggest honor is when other people ask them for help. Because we all just want to feel useful. So don't feel ashamed to reach out to something for help.…”

“And I think you don't need to reach out to people 10 years ahead of you. They can just be people a year ahead of you. In fact, an entrepreneur getting started, I might be less useful then than somebody two years ahead of them that knows, like, the latest distribution channels that I, like, kind of have forgotten.”

“I actually think you can make a fortune by only having a thousand true fans, depending on who your super fans are and how much they pay you. I think if you build a niche business where your average customer pays you hundreds of thousands of dollars, you can build a very meaningful business.”

“Said differently here, and this is me, not Kevin, there are literally millions of niche interests or problems that creators can create content around or businesses can create products for. And in an age where consumers and customers have more choice than ever before because of technology and because of the tools that…”

“new players, the way I view them becoming incumbents, whether it's in content creation or whether it's just in any type of business, is through the aggregation of many niches, and it'll be too late when incumbents notice it because it would have never made sense for them to spend time or resources on any one of these…”

“in most cases, a creator's best move is to actually get more than a thousand true fans so they can bring on operational help to do everything other than the act of creation.”

“Bigger competition has more money than you, they have more brand than you, they have more resources than you, but you have the ability to out-learn them by testing and learning the With hypotheses at way tighter iterations than is possible for larger companies.”

“Building this culture of frugality early in your business is important because it becomes harder and harder to act frugally once you've raised a lot of money or gone public.”

“once you have a business that's working, once you have product market fit, once you have a foundation and it is time to get really ambitious and pour fuel on the fire, it is a very unnatural motion for a bootstrap founder to do that.”

“The way you get to a Series A is by hitting certain growth metrics, and so The idea of profitability and how judicious are you with your capital becomes a second priority, and that's largely because of the incentive system that is created in the venture capital landscape.”

“Fast hiring is often a bad idea, especially in the early days of the business. It, and it becomes something that covers up larger problems like product issues. And also when you end up having a ton of people on your team and you discover those product issues later on, it makes unraveling all these problems…”

“Whether it's messaging to your employees, to your investors, or to your customers, repetition to the point of exhaustion is the only way you can be confident that people will know what is truly important.”

“More important than raising capital or the valuation you can raise at are the expectations of the investors you're raising from and how aligned they are with your expectations.”

“if you want a high growth entrepreneurial culture, you need to treat your business like a science experiment where your employees are like lab workers creating hypotheses and running constant tests, making decisions based on data and results versus having an emotional connection To the idea that's actually being…”

“and I think a written culture of communication is one of the best ways to solidify clear thinking across the organization.”

“A really good force function for founders or investors or potential employees of startups is to be really good at separating what is story from what is fact. It is important to know both, but fact is what makes a business strong or weak today. Story is a possibility of what a business could be in the future.”

“Having an ambitious mission and having crazy momentum and growth is one of the best marketing tools for recruiting great talent. And so, Bootstrap founders like myself love to shit on venture-backed businesses, but this is one of the great assets of venture-backed businesses, is if you have a wildly ambitious mission…”

“He says, I'll say this is such a common trait of great entrepreneurs. Almost all of them have this paranoid side. The side that makes them look over their shoulder as they're building their business. The side that makes them identify these small cracks before they turn into huge craters that actually can be business…”

“I believe there are so few examples in life where you can take riskless bets, meaning when you can do something that has a ton of asymmetric upside, meaning like something really cool could come out of the thing you're doing, but there is zero downside. And firing off a tweet like that, or even firing off a cold email…”

“being willing to do things that are cringe and shameless is actually one of the biggest superpowers of an entrepreneur. Because when you're willing to do things that other people won't do because they have fear of embarrassment or rejection, it gives you the opportunity to make things happen that other people wouldn't…”

“one of the best ways to build a company is to create momentum around your company. And one of the best ways to create momentum around your company Is to create content around your company so people feel like they are along for the ride, for the journey, where they feel like they're a part of this ever unfolding story.”

“you don't have to like every stage of business, and in fact, you probably aren't going to like every stage of business.”

“the way I think about it is people talk about this leap of faith, but I actually think if you build a Business effectively, or if you mitigate risk effectively, if you treat something as a side hustle before it becomes a full-time job, you should be looking at your transition as a calculated risk rather than a leap of…”

“in career, you want to stack the deck in your favor, and the way you stack the deck in your favor is you have self-awareness of the two or three things that you're really good at, and you work your way into a job or a position where 80% of your time is spent on those two or three things that you're exceptionally good…”

“They're able to go from the most zoomed out conversation about some unanswerable meta topic to the most micro discussion about their business, showing they understand it at the most fundamental level.”

“what I found is Really impressive entrepreneurs who have eight figure or nine figure businesses. They're super impressive, but they still are shaky when it comes to storytelling their business”

“there are three ways to win in news today. So in the news business, there's basically three formulas that work. The first is world-class analysis. So it's not about breaking the story. It's about having the best take And point of view on the story, that's something like Ben Thompson, who has the newsletter Stratechery.…”

“And what I've noticed is basically every founder who leaves their business Whether it's successful, not successful, whether they've sold the business or not sold the business, they basically go through the same exact journey, and I'm going to describe the journey to you. You leave your business, and you feel three…”

“I believe that training your employees in personal branding is a win-win because, first of all, employees don't have to talk about the company they work at. Just simply by them creating good content online and building an audience You will, your company will be associated with them, whether or not they're talking about…”

“creating thoughtful incentive structures is really, really hard, which means if you haven't put a lot of thought into them, you can probably assume that you're improperly incentivizing employees in many parts of your business.”

“If in a senior leadership meeting, you appear defensive. When one of your executives is challenging an idea you have, you can assume that you are now incentivizing other leaders to be silent and hold back their opinions.”

“The best way to combat character multiplication is to force your brain to avoid the character shortcut that I just mentioned and try your best to reassess people at the individual idea level, meaning you treat every new idea they share as a new opportunity to form a view on them versus assessing people at the identity…”

“Unfortunately, too many people misunderstand decisiveness for speed. The two are completely different things.”

“The way I understand it is that there is a difference between individual and system fairness, and oftentimes we try to be fair to the individual, which actually means we're being less fair for everyone else.”

“When people don't have answers to things, when people don't have answers to decisions that are made in a business or actions that are taken, they end up creating stories, and when they create stories, you end up having a culture of gossip. By making transparent your and your leader's thought processes, the oxygen for…”

“The first is that transparency is a superpower, and opaqueness is a massive weakness.”

“I think that saving people time and making them appear smart to their peers is a huge value add, and so that was just something that made me think back to the early days of morning brew of why I think it provided value for people.”

“actually by knowing what rung on the ladder you want to hire for, it'll likely dictate how senior or junior of a person you want to hire, because it'll basically dictate how much critical thought you need or not need in this hire.”

“62nd Startup very much just brings an old idea, which is Shark Tank. Uh, you know, founders pitching judges in front of an audience. It takes that idea and it just brings that idea to a new form factor, which is short form social. And then even if you think back to Morning Brew, we did the same thing. Morning Brew…”

“Uber, DoorDash, Uh, TaskRabbit has basically taken every American who wants to be a gig economy worker or monetize kind of their skills, but it's all been done within manual labor. This is the first time I've seen it be done within kind of like knowledge work.”

“there's a very big difference between being a creator and being an entrepreneur, and a lot of these creators do not know how to build a business on top of their audience. The only thing they know how to do is create content and then get advertising deals, and that's how they make money, but that is not necessarily a…”

“The issue with podcasts is they're highly inefficient. Like, if you think about all of the ways to consume content from newsletters to social posts to books to podcasts, I would actually say podcasts are similar to books in the regard that they're really inefficient.”

“So I would try to understand what is the core problem that an SMB faces that is not being solved by their existing software. And I would try to focus on, you know, almost like what is the Trojan horse product that would make a, an SMB super sticky where then you can kind of upsell, uh, Vertically into some of these…”

“the way I'd actually go about this is I'd pre-sell locations. So I'm in Hoboken before opening the, the Hoboken coffee shop, I would actually try to sell memberships to the coffee shop. And co-working space ahead of time. Once I hit a certain threshold, then that's when I would actually start trying to secure kind of…”

“And that means that my view is, is in the early days of a business, until you've hit true product market fit, you should be measuring success in your business by the speed of your product or service evolving versus the speed of your revenue growth.”

“what this experience again calls out to me is I just think a lot of people get sucked into the winless game of building companies for non values based reasons.”

“And I just like love these stories about just like gritty, unsexy tactics that need to be used in order to find problems in any industry.”

“So the one percent of creator businesses that work are going to be businesses that creators launch But the business has a good enough product where the business could have succeeded on its own without a creator. And the creator was simply rocket fuel on top of an already existing fire.”

“the downside of desperation is is similar to, like, when people talk about they love hiring employees who have a chip on their shoulder, is that is not a long-term driver of happiness.”

“The problem is sales is literally the most important skill for non-technical founders. And honestly, I would say sales is the most important skill for executives in general. And when I say sales, I also mean storytelling, so selling investors, selling employees, selling potential customers.”

“which means you have to default in the early days of building a business to a well, and a well is where most great startup ideas start. A well sits very low on the x-axis because few people are interested in what you're making, meaning on the x-axis, you're all the way to the left, but it is super deep on the y-axis…”

“The more work you have to put into reading something or consuming something, the better the odds that other people decided not to do it, because people are generally lazy, and so if you're willing to put in more work, the odds are you're going to learn things that other people weren't willing to put in the work to…”

“Every action you decide to take in life Is one of two choices, whether you know it or not. You either are making the choice to embrace short-term pleasure in order to endure long-term pain, or you are enduring short-term pain to embrace long-term pleasure, and what I can say from my experience is the most successful…”

“Or when you decide to hire someone who's, quote unquote, good enough because they're your only viable candidate left, all you're doing is embracing the short-term pleasure of checking off the hiring box, but you then open yourself up to the long-term pain of potentially having made a mishire, and then you're going to…”

“And the general rule of thumb that I would give you is that you should start with a Funneling your rented audience to an owned email or owned podcast as soon as you hit a point of critical mass, which I would say, you know, roughly is a few thousand followers.”

“And the third tactic is your hook is the most important thing. It is the first sentence of a tweet or the first line of a YouTube video. It allows someone to decide in three seconds to Whether your content is worth their time or not. If you spend one hour studying good writing, the first 45 minutes should be dedicated…”

“having a lot of demand for a business does not mean you have found product market fit. It simply means there are enough people interested in the problem you are trying to solve that they want to talk more with you about your business.”

“my views is like, it probably takes you a year to truly figure out what you're offering and who you're offering it to, to actually reach product market fit.”

“anytime you're doing something net new, you can assume that you're going to be mediocre at it because you have a lot of blind spots. And so, like, the first time you're a CEO, the first time you're a manager, the first time you do any job, the first time you hire execs, just assume you're mediocre.”

“the more you use a reference point from your own business, the more you open yourself to possibly making the mistake of hiring someone who maybe is one or two X better versus the 10 to 15 X better because you don't truly have an understanding of what really senior and really good is in the overall market.”

“First, I would say like a classic trait of bootstrap businesses versus VC backed businesses. Is in the early years you hire for potential, not experience.”

“And so I actually think what's helpful about this platform is not actually how it is stored. It's a question of how do you create the urgency for someone to get their stuff in order or have their family get their stuff in order well in advance of them passing before it is too late. And so that's why I think it's an…”

“Before you go and raise money, and especially before you go raise a lot of money, you should be completely sure that you want to go down the path of taking money from professional investors. Because once you do that, The expectation of how you're going to grow your business changes materially, and whether people like…”

“when you think about scaling like a law firm or a medical doctor's practice or a financial advisory firm, oftentimes the bottleneck is your supply, like supply for talent is your biggest constraint to scale. So a way to think about this is what is a service you can provide that the supply or your talent is low skill…”

“And then the fifth, and I think this is the most unique aspect for brainstorming a business idea, is focusing on an existing product service and pulling out the most standardized version of that service that still has high demand.”

“I think if you were to go with the route of dog grooming, I think a dog grooming brand is a great opportunity, but where you end up getting stuck is it requires very high skill talent. Dog owners are very particular about their dog's cuts. They expect someone to be really good and give their dog A very specific cut…”

“agency business to software business transition is such a classic move For agency entrepreneurs. And this isn't a bad thing. This is just something I see over and over and over. Here's how I believe the story typically goes for people who start agencies. You start an agency to solve problems for clients based on your…”

“I find that some of the most impressive business minds have chronically paranoid brains, and in general, I wouldn't call Justin a paranoid person, but I mean this trait in a good way. When I was talking to Justin about his business, one of the things he mentioned to me is his desire to both professionalize his brand…”

“The second thought around online education is that courses whose focus is around making you money, they will always sell better. Justin was smart to make his course not just about building an audience on LinkedIn, but also about monetizing that audience because people are always going to be more likely to pull out…”

“Lesson number two, only change one variable when you're moving your audience. Four and a half million people, no morning brew for our daily newsletter. By keeping the variable of news constant and only changing the platform, From newsletter to YouTube and podcast, we decrease the friction of having our audience follow…”

“What we've learned over the years is that transferring audiences across like platforms is way more successful than different platforms, and what that means is promoting a new newsletter in your existing newsletter is way easier than promoting a podcast in your newsletter”

“Having a huge audience is a blessing and a curse. It can supercharge new things you launch, but if you treat it as a crutch, you will never create great products that are truly exceptional on their own merit.”

“The rule I use is the seventy-thirty rule. When you're creating a podcast, I would assume 70% of the content can be used in your video form, but 30% has to be changed so that you're publishing something that is built to perform on the specific platform, in this case, YouTube.”

“Because we live in an era where the ability to create content and build an audience has truly been democratized because the cost of creating content is basically zero now, people are gravitating towards consuming content from brands that they resonate with. And it's way easier to resonate with an actual person versus a…”

“growth is mostly linear, maybe one day exponential. There is an old Founders Journal episode that I'll try to find and link to in the show notes, but I talk about this concept called the balloon effect. Now, imagine you have a water balloon under a faucet, and you start letting water run. The balloon is going to slowly…”

“finding content market fit is priority number one when you start creating content. Everyone talks about finding product market fit as As being the first job of a CEO in the startup world. And I think finding content market fit is the first job of a media company, CEO, or a chief content officer for a bigger media…”

“So to boil Sam and Gary and Matt's view on co-founder, no co-founder, multiple co-founders into kind of one thesis, it's most likely to be successful is having one good co-founder. After that is being a solo founder, and after that is having a bad co-founder.”

“I have to provide enough of a service to these ghostwriters in terms of giving them enough leverage to handle way more clients than they could handle on their own, doing all the account management and the non-creative stuff that they don't enjoy doing, handling billing and all the back office stuff. Basically, my…”

“if your customer doesn't like your current product, then when you come out with a big idea in the future, they're just going to associate that new product with all of the problems that your old product has that these customers face.”

“intuition isn't this arbitrary thing. It's not just gut. These 20 really smart, immersed people have millions of data points that have fed through their brains to inform their intuition. It's leaning on Kind of the human brain computer as a collective to make final decisions”

“I also think, um, it's kind of like in some ways the reverse of radical candor from Kim Scott, which like I generally view that as, um, you as a manager, what's the best way to land feedback with your employee. But I think it works in the reverse where it's like give you as the employee, not only Can be open and honest…”

“rather than trying to eliminate busyness altogether, because I generally think when you try to go cold turkey, it isn't necessarily sustainable, I would argue the more moderated or sustainable thing to do Is to focus your busyness on one to two tasks that you love being busy with.”

“I would say the biggest issue that I have that many entrepreneurs have is they are really bad at deleting tasks. They, even if they're good at delegating, sometimes they'll delegate tasks that actually shouldn't be delegated because the fastest way to do a task is to not do it at all.”

“there very much is kind of this power law of there are, let's call it. 10% of your, whether it's tweets, Whether it's your TikTok videos, whether it's your YouTube videos that contribute to 90% of your followers or subscribers.”

“once you're able to find the labor and train them up, The process of doing that actually becomes a moat to this business because it creates friction for someone else to have to recreate that recreate this.”

“at 36,000 dollars a year to get to a million dollars a year in cash flow. You only need 27 clients.”

“That money left over represents two things. It represents the extra hours that you worked in your life to accumulate that money that could have been spent doing things you truly enjoy, right? Because say you had a 100,000 dollars left, you spent time in your work getting that a 100,000 dollars after tax. You didn't end…”

“in the early days of the brew, we'd always, I always thought of it as like, there's two types of employees. There's pull employees and there's push employees. Pull employees are the people that pull the entire business forward. Push employees are the people you have to push, as in, like, give them orders, and they're…”

“first of all, like, I think scrappiness can lead to frugality, and frugality truly, like, isn't necessarily a good thing.”

“events businesses can be 30 to 50% margin businesses like they're super profitable.”

“scrappiness is a helpful tool to drive creativity and progress, but scrappiness for scrappiness sake becomes more about your own ego And less about how it helps you and your business.”

“no successful business that he talked to found success from more than three strategies. So said differently, as I described earlier, have all of your strategies at the top of funnel. Whittle them down to the two or three that you think will work and stay focused on those two to three. Don't try to go wide and an inch…”

“A meeting is a form of communication in a company that has the highest opportunity cost of time. So the bar should be super high for when you call a meeting.”

“Three to five people attend a meeting to make an important decision that has cross organizational implications.”

“for this, I just feel like there's actually a perverse incentive where as you become big as a company, Your needs become more bespoke. So you have like taxes, you bring an in-house accountant in, or you go up market with banking to JP Morgan. So that's my biggest question is how strong the bundle actually is for them.”

“The third effect, and I'd say the most detrimental, is that when I experience imposter syndrome, it makes me lose confidence in doing the things I'm actually really good at. And that's because imposter syndrome doesn't just attack specific skills. It attacks your character. It attacks your identity.”

“if you're competitive, if you're growth-minded, you're going to create difficult challenges for yourself, and you're going to want to gain new skills in life. And when you do that, your challenges will most likely exceed your skills.”

“if I repeat this enough times out loud to myself, it will allow me to sit with provoking thoughts of imposter syndrome without obsessing about them over and over in a way that impacts my ability to perform.”

“Creator brands can be big, but to truly have them grow outside of the person themselves, it has to be a movement in itself.”

“I believe that founders are better operators when they write investor updates. It is so incredibly easy to get stuck in the weeds just doing, doing, doing when you're running a business, especially in the early days, and the act of writing recurring investor updates is a force function for thinking strategically and…”

“Don't include more than three asks. Beyond that, people don't have a sense of what's important.”

“Because just like entrepreneurs, Investors are competitive. They like being atop the leaderboard. And so if you can gamify and create a leaderboard on your monthly or quarterly investor update, they are going to be motivated to add value because they want to be seen as the winner of investors.”

“a bomb sniffing dog of business is key to find cracks before they become craters. But it doesn't have to be me. Again, assuming someone else can be the person who does it.”

“So the first time we did it, we had 10 ambassadors. We were super stringent. We went through resumes. We had an interview process, and we're like, we're gonna pick the, the most impressive people on college campuses who's, like, The student body president in like five different clubs because they have access to all of…”

“and to this day, A very simple prompt, writing prompt, is like the best proxy for someone getting hired at the brew. You take a big business news story from the last few days, in a 150 to 250 words, you summarize this story in a way that connects with the audience through voice. Within two sentences, we know whether…”

“I think there are very few, at least if you're talking about a digital solopreneur, where it's, like, truly one person. Like, I think a lot of times it ends up turning into, you have a VA in, um, the Philippines, or you have, like, an agency that's part-time helping with you.”

“At the end of the day, if you turn every company into a media company, all of a sudden, monetization can grow into also, like, add dollars and not just the business.”

“one of, if I was to reflect on like the mistakes we've made over the years with morning brew, it's, it's, we were really ambitious, which was great, but at times we were ambitious all at once in one point of time versus sequencing. Like, let's do this thing. Once that thing is done, let's focus on this thing. And so I…”

“If you want to take revenue from, let's say, two million to four million, You should create constraints where you narrow down all of your focus as a company to the one thing that is preventing you from closing that gap from two to four.”

“That's probably the best demographic to build a social network around because I can't think of a time in your life that is filled with more, like, gossip culture, the, the desire to feel a part of a group, FOMO if you don't feel a part of it, and so unfortunately, you know, when you're in high school, so much of your…”

“you would ask every investor to start, what made you excited to take this meeting? And I just think it is the best lesson for entrepreneurs who think either They think they're great salespeople, or they're trying to figure out how to sell, and they haven't really done it before, and they just assume they have to start…”

“How do they build wealth when they know that check is going to end and it's going to be through building equity in something. And building equity in something that grows beyond them as the, as them being the first best marketing channel.”

“Second, really important point in this era that we live in where there are a lot of network based businesses and with markets that have leaders that are network based, it generally is winner takes all. Like it is hard to be the business that is in second, third, or fourth place. The business that is in first place…”

“It has never been easier to build a product because of the acceleration of technology and the low cost of building any new product. Finding talent to work on your product is easier than ever because just You know, amazing marketplace that exists online for finding talent from LinkedIn to Upwork to Angel, but the thing…”

“we felt like it is recession resistant because it's a cheap form of entertainment. So in a down market, families are still going to want entertainment and 10 dollars to go play mini golf seems affordable relative to other options.”

“note-taking apps in general, which also I, I pretty much agree with most of the time, unless the functionality is really 10 X better. Because at the end of the day, most of the notes that I'm taking are on my Mac, on literally like the Apple Notes app, and it is good enough, and it is free.”

“The advantage shifted from distribution to owning attention, and the power shifted from traditional media institutions to aggregators.”

“The reason I think I run the risk of sloppy thinking here is because I'm so passionate and emotional about the problem. Because I have been plagued by anxiety in my life, I'm naturally really excited by the prospect of helping people work through it. But because there's emotion baked into that excitement, that can lead…”

“Because imposter syndrome doesn't just attack specific skills. It attacks your character. It attacks your identity. It attacks everything you believe makes you you.”

“what I quickly realized is that by talking back to my anxiety, it actually made the waves of imposter syndrome and anxiety longer. And the feelings of fraudulence even more pronounced.”

“She will moderate an open and honest discussion, but she will never act As the intermediary that engages in conversation about the other person without them there.”

“Don't beat around the bush. Don't deliver a compliment sandwich where you give compliment, feedback, compliment. Be honest and be specific about how someone can improve. It is the best way for you to see results, and it is the best way for team members to be given the gift of knowing how they can tangibly improve.”

“there is such an incredible competitive advantage awarded to businesses that basically end up doing the shitty work to digitize a highly fragmented physical environment that no one else wants to spend the time doing.”

“the best analogy for thinking about this Intuit acquisition is them buying MailChimp Is to SMBs what Salesforce buying Slack and other companies is for enterprise. Basically, Salesforce has been trying to buy the full stack for enterprises to be able to grow and accelerate, and into it with QuickBooks, Credit Karma,…”

“as you gain credibility as a business, as you become known as an upstart media business, you're going to lose employees either via them getting poached by other media startups or established media businesses, or the employees simply leverage their brand And their resume now with your company's name on it to join…”

“as the business gets bigger, And as you go from early stage startup to late stage startup, and there's more clarity around the specific parts of the org and jobs to be done, because there's more of a plan, what you end up needing is not Swiss army knives, it's kitchen knives that can go really deep and do one thing…”

“In order to grow the lifetime value of a customer, you need to launch adjacent product lines that are complementary or serve the same psychographic or demographic of customer. But the risk here is that you run the chance that you dilute your brand and become a company that really doesn't mean anything to people or…”

“basically the strategy for an employee should be ask for promotions as fast and often as humanly possible without pissing off your boss and management.”

“Finally, something that I've noticed, and people have told me, is that when they negotiate for their promotion or their raise, they get defensive, and they end up positioning the conversation as a threat, where if they aren't given this thing, they will leave. I've never seen that actually work really well, unless you…”

“99% of the time a Slack message does not need to be answered right now or even in the next few hours.”

“Once we started paying our ambassadors to get subscribers, they were less effective, and the relationship went so downhill between us and them.”

“And so a year-end bonus isn't as good as a quarterly bonus, and a quarterly bonus isn't as good as a weekly bonus, and so the fact that Nucor used weekly bonuses to keep employees motivated was a huge win.”

“So smart contracts really is the feature that underpins Ethereum. It is the defining characteristic that transforms Ethereum from a singular currency that functions like gold, aka Bitcoin, to a programmable blockchain or technology that hundreds of companies can build on top of.”

“If you believe that Ethereum is a future digital economy, that it really is going to act as the bedrock for so many businesses, then Ether is almost a stock. It's almost stock in Apple. You can buy Ether to take a bet on the future of Ethereum, because if you believe in the growth of the Ethereum ecosystem, then you…”

“That extra hour or two or three hours at the end of the day, let's say between eight pm and 11 pm, It makes negligible difference over years of working in your job, especially if it's at the end of the day where you're less likely to be effective anyway since you've already worked for 10 hours, and all it's doing is…”

“Really, at the end of the day, you want to sell FOMO. You want to sell FOMO where a potential hire says, I can't not join this company because I'm going to be missing out on this incredible train ride. I can't not invest in this company because I think this company is going to be huge. You know, I can't not advertise…”

“And with tools like Shopify, Substack, MailChimp, Etsy, Patreon, Kickstarter, and all of these different creator platforms, the cost of failure in business today is really, really low.”

“All of this is to say that I think most marketing strategies are unscalable, and if you plan to do anything but deploy a combination of unscalable marketing strategies in the early days of your business, and honestly, in the later days of your business too, you're not going to have a growing business for very long.”

“I can tell you from seeing it, companies get addicted to spending money on paid marketing on platforms or get addicted to just SEO. Then they find their growth slowing and they have no other ways to grow because they haven't thought about it proactively.”

“We passed around sheets of paper. We asked people to write down their email addresses. Fun fact, that was the highest converting way to make Announcements asking people to take out their computers, go to our website and type in their email addresses was way lower converting because there were more steps added.”

“The first is that the foundation for your company's culture and its values are seated on day one. I fundamentally believe that. I think it's possible to shape culture in the later years of business, but I do not think you can just change it all together.”

“I'm not sure if it's because we as entrepreneurs overestimate our abilities or underestimate the time it takes to complete something, but everything always takes longer than you want or expect when building a company.”

“there is little that is more detrimental to a business. Then miss hiring. It is so bad for business. And in some cases that it can actually kill a business.”

“You can always assume that if you start to doubt the fit of someone that you've hired, several other people who worked closer and more frequently with that person have had those doubts for some time.”

“Just like in a first relationship, first-time managers want to make sure that they are the best manager possible, and unfortunately, one of the ways that they do this is by making big, lofty promises about promotions, compensation, and other things like that, even if it's not a realistic expectation to set.”

“In decision making, right and wrong is far less important than why or why not. In business, you quickly find that there are very few decisions that you make that are so clearly right or so clearly wrong. Most of your existence as a professional sits in this kind of murky middle, and the way you thrive there is not by…”

“At the end of the day, you as a builder are going to be great at one or two things. Other than that, there's always going to be someone better than you to do the things you're not great at.”

“it not only offers product that delivers on Twitter's highest promise to its audience, right? Which is to serve the best information on the internet based on your interest, but it also creates more lock-in than ever before for people creating content. Because now any person or brand that has been creating content on…”

“imposter syndrome, you know, doesn't just attack specific skills. It attacks your character, attacks your identity. And when I feel like my entire identity is attacked, it will make me feel more anxious, not just about the things that I don't think I'm amazing at, but also the things that I think I'm really good at”

“what I quickly realized is that by talking back to the anxiety, it actually made the waves of anxiety longer and the feelings of fraudulence more pronounced.”

“what I've learned about all of my manifestations of OCD, whether it's around health, whether it's around relationships, whether it's around work, is that my unwanted thoughts latch onto things that are, one, incredibly important to me, and two, don't have yes or no answers.”

“And so an activity I began doing is actually welcoming the anxiety, welcoming the imposter syndrome, and telling myself, It's this fear of failure, this fear of fraudulence that is actually driving me to get better. And so I've started to kind of like become friends with imposter syndrome where I've, I've told myself…”

“What I tell myself now is that my to-do list is a tool for accountability and treating my time as a precious resource, but my definition of success should be directional, not absolute. What that means is if I worked on the things I said I would work on, it was a good day. If I got distracted and only spent 50% of my…”

“An audience creates options and options make you dangerous in your career or as a company.”

“The hardest thing is in the early days, co-founders need to be, be able to do all of the jobs well enough to get the business off the ground.”

“Morning Brew has done cross promotions with everyone from top 10 business sites in the world to YouTube influencers, but the most effective cross promos have always been same channel partnerships. What that means is Morning Brew cross-promoting with another email newsletter of similar size. I generally think it works…”

“Meetings are not meant for updates. Meetings are not meant for status reports. Meetings are meant for two or multi-way communication. And if they don't have that, they're likely better off being an email form.”

“what I wish people would realize is that just because a decision led to a good outcome, it doesn't mean that you made a good methodical decision at the time.”

“by focusing on a single channel brand, it gives you the permission to build a multi-channel franchise because you're kind of, I think in a good way, putting all of your eggs in one basket to build up an audience in a place and then start creating content in other places.”

“Good example of a partnership is where you are interested in going into a new line of business, but you don't want to hire a full team yet and assume a lot of cost and risk for it. Partner with someone who already has the team, already has the product. Do a rev share with them. Yeah, you're not going to participate in…”

“It is impossible to stay focused on a meeting for a full day over Zoom. My general rule of thumb is that you should take a break every hour if it's virtual, and every two to three hours if it's in person.”

“EOS says to also have people share their expectations for the meeting, but I've generally not found this to be a great use of time because people say pretty similar or generic things.”

“And your goal as a company is to hit at least 80% of your rocks or goals in a given quarter.”

“This is a tweak that I've made to the EOS process because I believe tackling key issues is the best way to inform your next quarter rocks,”

“A meeting is a form of communication in a company that has the highest opportunity cost of time.”

“Lesson number two, make meetings two thirds as long as you think they need to be. One of the worst practices is when a meeting goes the full time, just because that's what the calendar said. And we all do this in life. When we give ourselves a certain amount of time to finish a task, we always inevitably take up the…”

“How you should think about it is if two pizzas can't feed the group, your meeting has too many people, and roughly speaking, this means your meetings shouldn't have more than five to seven people.”

“If as the meeting leader, you have not shared a meeting agenda, meeting goals, meeting roles, and meeting prep with folks prior to the meeting, you should not expect the meeting to go well.”

“A meeting is a product and its customers are its attendees.”

“memorializing the meeting is just as important as having the meeting itself.”

“keeping meeting minutes is also a great force function to keep the meeting on topic and not go on tangents, because it will be pretty embarrassing to write a whole bunch of minutes that have nothing to do with the actual purpose of the meeting.”