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.”

“in our world, people say ideas don't matter. Execution is everything. And I violently disagree with that. I think that there's a set of several thousand ideas that you can actually figure out by mining using spy software essentially on the internet that are just pretty simple autopilot, autopilot execution ideas, uh,…”

“your ability to assess and know whether they are the right people, if you're willing to put that to luck, then sure, you can just hope that you hired the right person, and you have no way of assessing the quality of their work output. If you can write a strategy that's okay, If you have advisors, if you have people you…”

“Getting a million dollar SaaS ARR is probably as hard as getting a million dollars in EBITDA, let's say in a services business. And guess what? They value those, those streams are valued exactly the same. So like the market is very efficient in terms of how it treats these businesses and these business types.”

“I think angel investing is dumb for your first dollars. You're going to lose 80% of your takes. So I still think angel investing is dumb for 99.9% of people. Don't play a game where you bet on other people's ability before you've bet enough on your own and stacked up enough cash.”

“the only thing in common among successful founders that I've worked with, funded, uh, interacted with is they have one comparative advantage with the rest of the world where they're in the top one percent or top 10 basis points or sometimes even top one basis points on one trait.”

“If you don't have one of those three things, a seed investment is a horrific idea.”

“if you're the most tenacious person in the world, if you, if you talk to that person's mother, they can probably give you examples from the time that that person was five years old. Um, and if they, if they can't, it's probably not top 10 basis points. Or if you're the smartest person ever, there's ways that that…”

“take everybody on your team, I'll keep pushing along. The envelope of what they can do until you see where they're struggling. And then everybody will have a natural limit, but keep pushing until you find it. And then you're going to get people to achieve things and achieve things for the company and succeed in ways…”

“And the reason why parallels matter is you can only accomplish the, the number of things you have simultaneously in parallel that are, that are defined by the number of barrels you have. So having more headcount does not allow you to accomplish more.”

“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.”

“22 or 20% plus, I would say, tweak your market, tweak your product. You can iterate your way there. It's when you're sort of in the 10 to 15% range That I start to think, well, you know, maybe you should just have an entirely different market or an entirely different product.”

“most founders, because we're builders, we obsess over the product itself. Well, you know, the product isn't resonating quite as much as it could or should, so let's keep tweaking the product. It turns out to be way faster to tweak the market, because you can leave the product the same.”

“Use the main benefit of the very disappointed users to segment the somewhat disappointed users. In our case, the main benefit is speed. So first of all, we have the somewhat disappointed users for whom speed was not the main benefit. I strongly advise that you ignore these people, we do too, because the main benefit…”

“If we only double down on what users love, and this is what vision-driven teams tend to do, we would not increase the product market fit score, because you're only addressing feedback from the people who already love you. If we only address the objections from the somewhat disappointed users, this is what data-driven…”

“The first sort of overarching piece of advice I have for everyone is, even if you have a full-time job, consider starting a side hustle, because nothing will give you more tax benefits than having your own business.”

“never dismiss a good idea because of poor execution. And five people could have gotten it wrong in a row. It doesn't mean it's bad. They just may have gotten it wrong.”

“one of the ways to wreck new product development is to get too many opinions too early. Everyone's got an opinion, and especially when something's new, they're gonna tell you what they think, and then you end up having to sort of field and explain your reasons For doing what you're doing to too many people and it slows…”

“the ambition typically, or ambition is typically a word used to talk about, like, amassing, and collecting, and growing. You know, it can also mean, in my opinion, like, it should mean existing, sustaining. I'm ambitious at that level, but I don't need to go destroy the competition. That doesn't interest me.”

“PowerPoint is really designed to persuade. It's kind of a sales tool. And internally, the last thing you want to do is sell. You want to, you're again, you're truth seeking. You're trying to find truth. And the other problem with PowerPoint is it's easy for the author and hard for the audience. And a memo is the…”

“fundamentally, I do believe early startup employees, like the first few people are undercompensated in terms of what are like, like norms of how much to give early employees. Like historically, a lot of people, you know, would give First employee, one percent, and sometimes waterfall goes down from there. I think it…”

“generally the board is a very, um, They're frightened of risk. They're frightened of getting sued. They're frightened of told the wrong thing. Like, a lot of times doing nothing is easier than doing something that might be very aggressive, that'd be hard, and a lot of these startups need to do, like, very difficult,…”

“I think you can always, always, always take a secondary if someone offers it to you with the caveat that you make the exact same offer to the rest of your team. I think that's a really important rule, but otherwise, I know a lot of investors are like, oh, you shouldn't take secondary. Bullshit. If there's a market for…”

“A lot of the stuff that came from Twitter were people who were one to five person companies, You know, solopreneurs, which I don't have anything against solopreneurs, but they would tend to bring someone on. They don't have the time to actually manage them. And then three months later, they would churn. They would take…”

“And then the problem there is you're building one product for one application. That application will never be done. A product will never be manufactured in high volumes, which is hard for cost. And you're never really going to build an AI data engine on one product. So you, you really want a general, you really want…”

“anyone who's worth being an advisor probably should have 25 to 50,000 dollars to put into your company.”

“The warning I give to people is before you do that, let's actually start building in actual joy into your day to day, because I have had the experience of CEOs that I coach effectively turning off their fear. And then going, yeah, I don't want to, I don't want to run this company anymore. Like, I don't want to show up…”

“the new Facebook, you know, at paradigm is targeting like creative is the new targeting. So for anyone listening, running Facebook campaigns, you don't need to target anymore. It's broad. You let Facebook's algorithm figure it out.”

“there's two types of mishiring, and I think people usually think about the first that I'll give you, but it's the second that really kills you. The first is you just mess up. You hire a senior exec, you know within four to six months of the wrong person, uh, hopefully earlier, It takes a month to fire them, you have to…”

“venture capitalists are beholden to their LPs or the bigger fish that invest in them as one asset that is among a variety of diversified assets. It's their job to, on paper, take your company and say, nasty gal is worth three hundred and fifty million today when we invested in it, and push you, push you, push you to…”

“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.”

“most of these traits show up early in life. Like you don't have to have a professional experience. Uh, you can illustrate through high school experiences, college experiences. Like if you're, you know, better than everybody else in a particular trait, it will show up. You don't really have to have a lot of domain…”

“domain expertise comes usually with what doesn't work, not what could be possible. Um, you know, the node, uh, has a good expression of domains are expert in the fire world and what you're trying to do is create a new world. And most people with expertise typically have learned all the rules and quotes and And are…”

“everybody tells you entrepreneurship is about freedom. They tell you it's about making money so much money that, you know, you want it to do with it, or they tell you it's about changing the world. And I think those are all lies. I mean, I think that the actual best highest purpose of entrepreneurship is to improve…”

“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.”

“300 dollars. What I learned early on is no man's land. You should either charge thousands and thousands or tens of thousands of dollars or like a 150 bucks. 300 dollars is no man's land. That's, it was a bad, I really screwed that pricing point up, and the research, by the way, told me I was wrong before I even started…”

“The name of the game is basically like, that's why I read biographies. It's, it's just copy what others have done that's worked and, and try to avoid the mistakes that cost them a lot of like headache. And I'm not trying to invent anything new. We can, I can get real philosophical and say very few things are actually…”

“Hand-to-hand combat stuff, like, really works, and it's still really effective, and it's not that hard to get to a million a year in revenue doing that stuff if you give it six months of, like, every day, 40 hours a week.”

“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.”

“And that was when I learned, like, oh, like, growing 60, 80% a year, you know, series B is not, like, that was not good enough.”

“What is a billion dollar company? Right? Like, it means like the last share you sold for like, 11 dollars and you have like a hundred million of those shares out there... And you can like, maybe if you're lucky, get a loan on it or something. Right. But at the end of the day, You know, not a lot of money is really…”

“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.”

“After benchmarking hundreds of startups, Sean found the companies that struggle to grow always get less than 40% very disappointed, and the companies that grow most easily almost always get more than 40%.”

“Now first, and as painful as it is, we have to ignore the not disappointed segment. This might be difficult because they are very loud, but they are so far from loving the products that they are essentially a lost cause. And it's also very important because they will tend to ask for all kinds of distracting things. So…”

“one of the reasons why I don't go looking at other people's work is because once I have their work in my head, it's hard to have original ideas. Um, I actually prefer the newbie approach. Like, I don't know what the hell I'm doing. Uh, I think people who, who go into something not knowing anything about it tend to make…”

“taking cash out of a business, I think is a really healthy thing. Um, in our industry, it seems like people are always pouring money back into the business. You know, shit can hit the fan at any time, and a lot of businesses that were worth something aren't worth anything a year later, and if you keep pouring it all…”

“And what you get out of hourly, just like Uber, just like Airbnb, just like instances on AWS, you get efficiency. You get much better utilization of these assets.”

“all this AI stuff will, like, the whole designer-engineer split seems weird to me too, to be honest, because, like, the designer is really having to, like, write code now, uh, and then the engineer, like, it's, like, actually really, like, everyone is a designer.”

“when they come up with business ideas, they often drink a bunch of wine, and they're like, this would be a cool business idea, or have a lot of coffee, and this would be a cool business idea, when they should be using software to come up with business ideas.”

“Don't give things away and think that volume is going to, going to help you. Like, you know, the pizza shop in the corner is not giving away pizzas for free.”

“software businesses that have, you know, basically humans and Some tech, which is cheap, either in the cloud or, you know, people just need a few laptops here and there. And there's not much that you need to get going and building a software business or tech business in most cases. So I think in those cases, um,…”

“I think a lot of tech companies act as if they are companies with huge capital expenditures, and they're not, and they put themselves in a hole. Because now they're beholden to someone else on someone else's time frame. Um, they have to become a certain kind of company. There's really like only one option. It's like…”

“So yeah, that's an exception, but like your, your B to B accounting software, you know, whatever, like, no, not that that can't be a great business. It can be, but it doesn't need the same kind of approach as, as Airbnb or Uber.”

“I think businesses really, truly just unfold. And I'm here for that. I'm not here to predict where we're going to be in three years. I don't know, don't care, frankly. There's no real advantage to me predicting that.”

“if you're the most senior person in the room, go last. Let everybody else go first. In fact, ideally, let's try to have the most junior person go first, and the second, try to go in order of seniority.”

“So on a very tactical level, that means for certain areas like marketing, um, hiring freelancers more, hiring contractors more, but always being very thoughtful about, do we really want to increase the size of our core team? Because that tends to become an irreversible decision, and every single thing gets harder as…”

“I do think it's quite high ROI because you can spend tens of thousands of dollars, which is honestly not that much compounded over the lifetime of a startup if you raise money. And it buys you instant credibility because when you're a brand new company, credibility is such a concerning thing.”

“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.”

“And I think that's really the value of being more public in your fundraise, It helps you cast a wider net, which then you ultimately find the perfect match, the perfect marriage, and you end up, I think, um, really getting a sense for your market prices. That's the other thing that you benefit tremendously from is…”

“You know, it's true that since we did raise in public and we were successful, we've had some imitators and some copycats, but none of them really have affected us. You know, it was a little bit of like, oh, should I have Been so public about our success when I see all these, you know, imitators and companies, they've…”

“Great organizations set a vision and head in a direction, and everybody aligns to make that happen.”

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

“I think if you haven't had a relationship with somebody for like 10 plus years, you're never really going to truly understand how they're going to behave in certain instances on a board like this, to be really frank.”

“don't let the tax tail wag the dog. So I would rather live where I want to, and then figure out my taxes. Um, so again, to me, the whole point of having money is to be able to live where I want.”

“It's what he said is it's best to optimize for the medium case scenario where things don't go absurdly well, but they also don't go poorly. So to ensure that you're protected, because if you do the opposite, right, where you just raise money at a super high valuation, thinking things will go amazingly, you could end up…”

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

“They can convince themselves that they're actually meaningfully moving toward product market fit by just sitting in the room and coding all day. Most of the time, that time is wasted. You know, it's not getting you any closer to the insights you need to building a business and building a product people love.”

“So lean startup is not a good way if you want to have maximum impact.”

“Like, I think everybody gets the idea wrong that like entrepreneurs are like these like gun totem, like totally okay. Corral like betting everything all the time. Like it's the opposite of that. Like if I have a risk of ruin, I'm totally screwing up.”

“The difference is, uh, For me, like, 10,000 customers have to fire me for me to be out of a job. Uh, for other people, only one boss has to fire you when you have a W-II job.”

“I think when you have a software product, I think having leadership who knows how to build software is really important, and the further away you get from the actual building of what it is that your product is, uh, the worse your product is ultimately going to be.”

“And so I think the, the nature of being a co-founder CEO is you have to be 80% good at basically everything. It's, uh, it's kind of a strange role. You have to be able to write a passable growth strategy and a passable clinical strategy and a clinical, you have to be able to write a passable regulatory strategy. You…”

“the biggest thing to do is to get rid of your to-do list and put all of your action items on your calendar. Block off the amount of time that you think it's going to take. You have a to-do list. Everyone has a list of things that they want to do, and just translate all of that into time on your calendar.”

“Really, if you don't like doing a certain thing, like writing investor updates, it means that you should probably have somebody else do it because clearly you're not a reliable person on this specific type of task.”

“And so what I don't believe in at all is like, hey, pay yourself nothing and really prove like you're some harder that can live off like 25,000 dollars a month. Because at the end of the day, like as an entrepreneur, You want to make sure that all of your focus and attention are focused on the business and not how are…”

“I know some entrepreneurs that actually get into, like, kind of pivoting their business to do consulting as well. And they kind of phrase it as, I'll do consulting to learn about the space a bit more, but it's really kind of to pay the bills. And I think it's just a total distraction from what it takes to scale your…”

“If you're heads down building and actually executing the business and growing it, those investors will be that much hungrier to speak to you in the future than if you took a 30 minute call with them now.”

“numbers on their own are meaningless. I can make numbers say good or bad, no matter what.”

“I think there's something to that, especially at those early days, which are an early stage company. I think it's almost impossible to do it remotely, though. There are a lot of examples of companies who have, like, I think GitHub from day one was remote all the time.”

“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.”

“However, if you're poor, like I was, if you're just getting started out, I would rank The passion part the lowest, and I would rake the, what the world needs and what they're willing to pay for the highest.”

“the space we were operating in, short form video, is a very challenging category to be in, right? You don't control the views. You don't control the audience. And you're built atop these layers of social media platforms. So it's very hard to have A sustainable business that can stand the test of time and can wrestle…”

“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…”

“You can boil almost everything down to three big levers that the business had or the product had on the aircraft side. You basically had, um, we basically, I basically built an, like, you know, electric range equation that amounted to, um, how much powertrain efficiency, like, you know, how, um, high efficiency of the…”

“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.”

“I think the most successful companies is somewhat obvious or not obviously, but it will take one square of that matrix. Like I said, customer service for banking and go, that is a very specific solution. I'm going to have the best models. I'm going to teach, I'm going to use open AI, but I'm going to really, really…”

“building an advisory board is one of the, I'd put it as one of the many distractions that entrepreneurs create to think that they're going to build a better business instead of just selling stuff to customers.”

“inside of a company, oftentimes the returns on capital are way higher than even an investor ever gets. Like there's initiatives, hiring five salespeople can have a 500% return in a year if you do it well, right?”

“I think, I think every problem can get solved with a weekly meeting.”

“I don't think it's good actually for me to be in these channels. Like, I think it's important that I'm not, actually, because when I'm in them, then it feels like, oh, Jesse's alongside. He knows what's going on, and even we had, we had our first version of those meetings last week, and Carolyn was like, Jesse, this…”

“You start a company, it's your obsession, it's your identity, and you'll hear people tell you, like, Oh, like, don't make this your identity, right? But it's like, yeah, that's nice, but that's not the reality. Like, this is who I am.”

“what I saw there was that if you could combine the right mix of tools and technologies and talent that you could actually build this platform where you could have multiple businesses that grow at scale. Right. And like, that's how you're getting to like a hundred million Or three hundred million in revenue. It's not,…”

“the middle ones in my experience, you know, it's sort of the, the hammer and a nail thing, right? It's like, if you're a hammer, everything looks like a nail. So everything they look at us through the expected value of how big could this be? If I put a dollar in, will it get a multiple over it? And there's a lot of, in…”

“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…”

“I think one of the biggest problems with business school is it loves to tell people to set a business plan with objectives and goals. And like you have, the second you start with that, you have set yourself up for failure.”

“you see this classic mistake all the time, where people think they need to keep their cards close to their chest and, like, play it coy. Like, that is the worst way to do a deal. Because the truth is that, 99% of the time, there are two or three things that matter to you. There are two to three things that really…”

“Most of technology and coding is just logic. By definition, code is a logical structured system. And so asking questions and not accepting the, it just takes three weeks, or it's not possible, or the systems don't allow you to do like the number of times you've seen engineering teams across any company use like that as…”

“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.”

“as the leader, sometimes it is important that maybe the team's a little bit less productive for your benefit, because you're ultimately the only person who can see everything that's happening and you're ultimately making most of the decisions. Right. And so it's not a crazy thing for people to have to do things like a…”

“I would tell people, most people, if that's similar, like you go give yourself two years, Quit everything, go all in and make it work. And I think that sets you up for more success around entrepreneurial ventures.”

“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.”

“It's the whole conversation of whether the idea is big enough or not too big or no, it's all ego oriented versus just waking up in the morning and going, what will, what will make, you know, what will energize me today? What will be something I'm excited to do? And I think the more I've like my practice, it's a very…”

“the fear of commoditization of business is totally driven by venture. It's not driven by entrepreneurs because every business you can build a moat around over time and, and you can build some resilience.”

“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.”

“I think if your audience aligns with it, I think like a lot of people are going to figure out that Discord is a seriously powerful channel because it's community and community is a moat and it insulates you from everything else.”

“And so that's the one thing about B to B that I think is beautiful is you can just get on the phone and start pitching people. You see their reactions, you get their feedback. It's, it's in some ways it's way easier than B to C.”

“when you're doing really big deals, you don't want to pretend like a person is into it when they're not into it. You really want to make sure they want it. And so they had a little rule where they were like, wait three days for your follow-up.”

“Recession is, recession is the economy goes down by three percent, sort of up by three percent. So we go from being a 20 trillion to being a 19.5 trillion or 20.5 trillion. Like, I just, I personally just don't believe in that effect. Like, you think it's an excuse? Yeah. Well, yeah, sure. Will the purchase rates be a…”

“there's certain advanced strategies you can still hack, but I wouldn't worry about them if you're listening and you're spending less than 500,000 dollars a month on Facebook.”

“on average for every ad dollar of any platform, there's about 20 to 30 cents in services, support, software, tools to make use of that platform.”

“CEOs tend to make is they don't invest long-term. They have one EA for a couple of years and then another one for a couple of years. These relationships compound over time. You want to invest for a decade plus.”

“fear is the most common. By the way, it's the most effective, so I'm not judging fear, right? ... Yeah, you put a gun to your head, you're gonna run faster than you've ever run, but the downsides of fear are that they leave a negative residue on you and others, and they're not sustainable”

“layoffs are a function of greed, and there was a moment where people were just overbuilding a lot, and that's what leads to layoffs, and that's what leads to a lot of this stuff.”

“I've missed 10% of my flights as a life rule. Um, you're spending too much time in airports if you don't.”

“I try to avoid standing meetings. And the reason is, is because what's important this week or for the next week or two is going to be very different than what's important in the following two weeks. And I like to change and shift my hour, like where I spend my time depending on where I need to be, you know, what needs…”

“I think it's okay. For a year to stop and make no decisions and that to be your goal and to sit with not knowing and ambiguity in the liminal space.”

“my experience, okay, ours are really good when a company understands itself really well. Most people listening, me, you guys, like, we don't know our business that way.”

“Entrepreneurs can be masochists. And that can look like resilience, which I just don't even, those are like, those things stand in such contrast to one another.”

“And I think speaking to that, the whole, like, your business, and I've heard this so many times, like, your business is your baby, and it's like, it's not my baby, stop telling me that, you don't know anything about me or my motivations, and it's like, no, it's a business, it's not my baby. If it's your baby, you're…”

“The easiest is a billion. The hardest is a million. From a million, it starts to get easier at ten million, easier at a hundred, and even easier yet at a billion. That blew my mind, but it actually has proven in my situation as we're two-thirds of the way to a billion to be exactly true.”

“But if you master budgeting, that does not make a billionaire. If you master deal making, that makes billionaires.”

“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.”

“They're gonna leave your company because your culture sucks, or because they're not learning, or because somebody's micromanaging them. Like, yes, it's a carrot, but it's not what keeps people around.”

“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…”

“there's a really healthy amount of avoidance that a leader needs to have to redirect people to solve their own problems instead of allow your team to come to you, ask you what you think about it or how you should solve the problem and deputize them to come back with an answer.”

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

“people like him don't ask what's Correct or incorrect or what's right or wrong in the sense of running a business. They just do what they know and what they want. And I think there's something about entrepreneurs not worrying whether or not it's, is this the right course of action? He's like, this is just what I know.…”

“The third one I would, I would take issue with unless you're a Y Combinator venture funded. The third one you said, which is make sure that like few other people can do it. Right? Because, don't get me wrong, I, I think way more energy is spent on people being like, oh, it's not proprietary enough, or I found a…”

“hiring, especially in an early stage company, is extremely hard. Like, I was just talking to, to the CEO of Growth Assistant, I was telling her, a bet, a fifty-fifty is a good rate, and then when it comes to executives, it's even harder.”

“If you're gonna tell people you're a family, you got to behave like family and family doesn't fire people. They find other things for them to do. And there are companies, by the way, that operate like that. There's nothing wrong with that. But if you're going to run your business, if you have investors, if you're…”

“I think startups overly focus on it, and again, like, find it and use it as an excuse for why they can't close a deal. You know, if you think about HR software. It's a multi-billion dollar market. If you're starting a two million dollar ARR company, getting to three million the next year, sure, people, your sales…”

“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.”

“no business starts being defensible. And I think it's important for entrepreneurs pitching when a VC goes, oh, how do you make this defensible? You go, well, today it's not defensible. If it was, how the hell would I be starting it?”

“If you can steal from your top competitor, you should.”

“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.”

“And if you have money, And expertise and like audience or a name, you should be getting unfair terms every single time.”

“There's no way that mini golf courses over the longterm are going to be the best use of land for most locations. And so eventually you're going to get your business sort of taken from you by your landlord, which is okay if it's a longterm and you just get to kind of like cashflow it on in the meantime, but, but I would…”

“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.”

“In fact, when people ask me, uh, if they should go to law school, like as an entrepreneur, I often say the law school can be, if you, if you get out of it, you know, it can be The, uh, like finishing school to be an entrepreneur.”

“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.”

“If we only focus on the podcast numbers, we will fail. We have to look at founders journal as a brand. And as you, as, as a show, not as a podcast”

“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…”

“if you're looking to make a career pivot, say you want to work in podcasting, but you've been a financial analyst your whole life, no one's going to trust you that you can do that. They're not going to give you the benefit of the doubt.”

“Number one, it's like, have you made something people already want? I think needs to be something that, I think that's generally the problem people miss out on when they think they have marketing problems. Like, how do I market or promote this better? I'm like, you don't. No one wants it. That, that, that's really the…”

“And I don't, I don't know if there's a binary number, but I definitely think within 30 days you can have clear indicators, whether ads or affiliate or PR or social, uh, or referrals, whatever it is, are working.”

“And what people don't, I think, understand or have a good intuition for is that when you get deep enough into any scientific discipline or any field, you start seeing old intellectual cracks. So you understand two things. One of the things you understand is, what are the kind of, um, outstanding questions that we just…”

“If you think about relentlessness, to me it's kind of, it means like a pathological motivation. Like you're pathologically motivated. And where does pathological motivation come from? It comes from, I think, two things. It comes from love and fear.”

“If the fundamental, if the intellectual fundamentals are strong enough, you can re-derive anything.”

“Usually there's two, um, formulas, sort of. One is they've had experience in that industry domain that's very, you know, special. So, they understand what's broken and why, and they also understand how to fix it because they actually suffered through it, and they're, you know, sort of good product thinkers. They…”

“I think a ratio of barrels of 10% of an organization would be phenomenally high. Five percent would be pretty damn good. Now that said, I, I think you want, like, an 80%, at least, success rate of hiring, where the question would be, if you can make the hire all over again, what would you do it?”

“So when you're hiring employees, the tune of the model has to be different than when you're investing in founder. Like on the founder side, I only care about the upside. I don't actually worry about the downside of being wrong. When I'm hiring for a company, an organization, or interviewing people as a board member for…”

“fear is kind of obvious, but if I put a gun to your head, You're going to run faster than you've ever run in your life. So the benefit of fear is it's super effective. And that's one of the cool things about this paradigm is it never argues, because one of the first things an entrepreneur pushes back, oh no, but dude,…”

“Most of my businesses are very, very simple arithmetic, where it's like, hey, look, if I can get a million or two million people to subscribe to this thing, And I get, if I can get ads at this rate and fill this many ads, I think this could make like a hundred million dollars a year or something like that.”

“And my opinion is like a company that has billions of revenue or is a public They have so much data and intel on, like, where the world's heading that I can just piggyback off of their intel.”

“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…”

“Take the users who would be very disappointed without your product, and analyze their answers to question number two. Who do you think this product is best for? Now this turns out to be a very powerful question, as happy users will almost always describe themselves, but using the words that matter most to them.”

“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.”

“when you're that involved in every decision, and this, by the way, is very common for founders, right? You're like, this is my baby, this is my thing, I want it done this way. What you end up doing is you just create a bunch of people who are waiting to hear what you have to say about something. They're not thinking…”

“pre AWS, we're all, all the servers were like in the office, literally. And AWS made it so you could just like build stuff from your laptop. Maybe you don't have to think about it. And I think the same thing is happening with remote work, which is like, you can spin up quote unquote, spin up a team.”

“recruiting is hard when you basically can't train anyone in person. You have to like go straight to super senior type people. Uh, there's not that many of those kinds of people.”

“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…”

“A bunch of ideas, like, people just post on Product Hunt, it gets traction, and then this, like, indie hacker just gives up on it for whatever reason. It could be they got a full-time job, it could be, uh, they were able to build the product but not get sustainable growth, um, but it doesn't mean that that isn't a good…”

“The world has changed since 2014, 2016. There's AI now, right? So like a business that was not viable in 2016 might be viable in 2023 because of, I don't know, some automations that you can do. Um, there's creators who are hungry to do deals with startups and who are looking for monetization opportunities that didn't…”

“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.”

“Every startup company is unlikely to work. It's helpful to be in reality about that. Um, but that doesn't mean you can't be optimistic. So you kind of have to have this duality in your head. Like you, on the one hand, you're, you know what the baseline statistics say about startup companies. And the other hand, you…”

“Like, if there's an executive who is seriously weighing us versus Facebook, it's likely not a good fit. Like, we're not going to be able to pay anywhere near as much. We're, like, they're just not in the stage where they want what a startup has to offer.”

“So at Teachable, we ended up building the most bloated product in the world because I never knew how to say no to a customer. It was, if a customer came in with an esoteric requirement for something they needed, we'd build it, and then we'd figure it out. And as a result, by year five, we'd accumulated so much tech…”

“the key to being a second time founder and doing it well is to leverage the hype you have. Without quite believing it yourself.”

“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…”

“It's way easier to correct for. We don't have enough meetings. Let's try to schedule more of them than it is. How do I get out of this situation where I'm trapped all day in meetings?”

“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.”