Bootstrapping

“You probably won't be able to do freemium because you can't kick your revenue super far out into the future, and you need to charge enough that you don't have to find a kajillion customers to make 10,000 dollars a month or whatever you need to live on.”

“I met all of these really cool indie hackers and bootstrap founders who are validating in a very small way, but it's rather a safer, smaller bet as opposed to betting your whole life on something that's bigger.”

“So as a high agency person, being able to remove the fundamental constraint of capital as the limiting factor of a business, like, to me, it's like the equivalent of going pro. I think that there's vastly more cases in which venture capital makes sense for a h…”

“Would you rather own, you know, a hundred percent of a ten million dollar business or 10% of a billion dollar business? Like, of course, I think unless you really have some obsession with ownership, but I think most of these things are confusion about ownershi…”

“A funded startup is going to have some inherent pressures that you don't necessarily have if you're bootstrapping. A big one being like, they have to make sure they're targeting a big enough TAM. You know, the total addressable market is large enough to kind o…”

“What I mean is, you are decreasing your chance of success By bootstrapping, B to C, a two-sided marketplace, et cetera.”

“If you're building, like, a B to B company, especially if you're, like, doing a B to enterprise company, like, you'll need to hire a salesperson or a sales team, like, you need to, like, spend your money on marketing. It's going to be very hard to try to sell …”

“If you're going to take a small percentage of GMV, or you're going to be ad-based, or you're going to need a million users in order to be viable, these are just not easily bootstrapable. I say they, in general, they aren't bootstrapable, but I suppose one in a…”

“If you're kind of completely focused on bootstrapping yourself perennially, you miss the market. Because you miss making those investments and somebody else will come and accelerate and, you know, build that build that, you know, 10 X advantage.”

“You can get to a point where you're proud of things you should no longer be proud of. Maybe said a better way, the things that you're proud of can inhibit you. And so, you know, once you've been Bootstrap for 10 years, and everybody's like, wow, you've grown t…”

“If you want to build a big company, then you need the money behind you, I think. But if you're just looking to build a product that you can get to market, get some success and sell it, bootstrap it as long as you can.”

“The longer you can go bootstrapping, you know, the, you build, the more you build that you own. And so a lot of times bootstrapping can be a secret weapon and can have incredible advantages. And I think build stronger, more investable companies in the longterm…”

“And you're not gonna win that by just bootstrapping all the way, right? I think that's a myth.”

“Not only, should not everyone raise it, but I only think about one percent of venture-eligible tech startups should raise venture. I think one percent, approximately, should consider raising venture. I think nine percent should consider raising some type of fu…”

“The truth is we talk about on the internet that like it's a choice, but the truth is the venture capital is a niche product. It's a weird product. It requires T three D two growth. Most folks are not experiencing T three, two growth. Or don't appear to have th…”

“However, for those who can like bootstrap, that's the ultimate That's the ultimate, in my opinion, to avoid all of the conflicts that come from raising venture capital, and to own much more of the company yourself, that, that's when I'm like, tip of the cap, a…”

“Bootstrapping is more like building a business around your life. Whereas raising VC or P capital is more like stretching your life Around the business. At least that's how it feels to me.”

“If you're bootstrapping and you're hiring your first 10, 15, 20 people, And this person doesn't already know how to do the job and you're going to train them up from scratch, unless you really, really need to save on budget, that is a case where you are going …”

“At some point, the model might have the capability, let's say, to self-correct. Let's call it self-correction. And as soon as it hits that capability, you can see how, wow, bootstrapping now is trivial. And of course, it's not going to be that blanket across a…”

“Because, you know, in the life cycle of a company, you know, if you're doing anything worthwhile, you're going to need to raise money unless you're just one out of a million that bootstraps it and hits, you know, the big time from the start, that's very few an…”

“A big mistake I see folks making is thinking I can build a venture scale business, or I can build a business that will probably need a lot of funding, but I can just bootstrap it. Or I can build in a market where there's going to be a ton of funding and probab…”

“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.”

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

“I think, A, that's a path that many more founders should take, and B, a path that many founders will have to take in, in these coming years.”

“Bootstrapping is actually, in a lot of cases, in most cases, is the right call, and we don't have to be prisoners to this narrative that the venture industrial complex tells us, that We're not important if we don't raise funding.”

“It's good because it motivates you to build a viable business and a business that generates revenue and profit from the start. That is the superpower of bootstrapping. But it's bad because it teaches you to think in the short-term”

“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 b…”

“The value in bootstrapping is that it teaches entrepreneurs. It not even teaches, it forces them to have to figure out how to make money. And the more time under the curve they have making money and practicing making money, the better at it they're going to ge…”

“I think bootstrapping is actually, in many ways, a better way to get to be a public company.”

“Maybe in the future, if I create more startups, which I will, I would rather go to the bootstrapping and doing it myself rather than raising money and having that, you know, Strong metrics to be met constantly, and that big backpack, backpacking your shoulder …”

“Bootstrapping something for years is not possible for the average person, which is why this metal path needs to exist”

“This is a great example of a company that needs to have the investment so they can fulfill the promise that they have for their users of having this like quick, easy deployment that's really fast and snappy. Yeah, it's a great example of a company where both s…”

“Whereas with a bootstrap company, you don't get that kind of feedback. So it's like, I think you make money faster. You can be personally wealthy faster and you get to help people directly. But you don't get that opportunity for scale unless you work on it for…”

“It comes back to my rule. Don't bootstrap a two-sided marketplace. That's exactly what this is, unless you have access to one of the sides.”

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

“Bootstrapping is taking the pain of fundraising and stretching it out across the entire life of your company.”

“The basic idea is bootstrapping is for lifestyle businesses that want to cash flow. Funding is for companies trying to create a billion dollars in annual revenue.”

“I believe that almost anyone now, especially with no code, but with code, with learning to code, with all the resources online today, that people can change their lives through bootstrapping and not just through software bootstrapping.”

“Bootstrapping especially is just such, such a great equalizer. It's such a platform that does the tool solve a problem that's worth paying for, then people will pay for it. And they usually don't care who you are in most cases, you know, they don't care where …”

“I think one thing you probably lose though, is it's, in my opinion, it's harder to have like the really big outcome. If like the things we're doing or historically have done, it's hard to, It'd be like a ten billion dollar company from that stuff. And I think …”

“I will say it is harder than raising money. It really is. Because once you have funding, you can hire people to do stuff. You're worried less about all the nuts and bolts of it.”

“I think like one mistake I think a lot of companies make is not bootstrapping for longer. It forces you to be very focused on the problem you're solving. It forces you to work with clients, understand what they're willing to pay for and bake in that commercial…”

“Again, I think bootstrapping is a forcing device. Like when you don't have resources, you have to get incredibly sharp and crisp on what is your mission? What is your value prop as an organization beyond money? That's going to attract talent and that getting c…”

“If you want to create wealth, bootstrap. If you want to change market raise venture because your odds are, I mean Mike requires venture backed. I know my odds. I got a one percent lottery ticket.”

“Probably the first one. Yeah, I mean, that's really kind of been our mantra since day one. That's our CEO's whole, you know, methodology to it, and it's worked great for us.”

“If you want to bootstrap a company and you have no, no, no money whatsoever. Right, and to build a product. Go and get 10 customers to pay you for a service that you deliver behind the scenes Wizard of Oz manually. Customers want an outcome anyway. They don't …”

“Everybody says, well, overexposure to a couple of clients is bad. Well, Yeah, in the ideal world, it is. But if you, again, are starting and bootstrapping, and kind of like somebody, you know, you have a client who actually pays you a million dollars in advanc…”

“Starting a bootstrap business really allows the founder and founding team to intimately understand the business and all portions of it, unlike when you raise venture capital at, you know, the early stage. So I actually think that, and it was a great reminder t…”

“And I believe you can bootstrap your way to scale, but you'll have to catch the crest of multiple waves of good fortune.”

“I'm still, I still have very much an advocate for bootstrap as long as you can, until you get product market fit through, through getting product market fit after your product, product market fit, raise capital and efficient means when, you know, unit economic…”

“We bootstrapped our businesses and, you know, kind of plan to do the same in the future. It just makes it for us, it really de-risked That whole process. Cause we know even if we don't have like a, you know, a huge winner, like we can still get something out o…”

“When you are small, you cannot do five different experiments because your organization is not really set up for it. If you do five, you cannot really devote attention to it. So you have to be very, you know, you have to be very precise and very diligent in wha…”

“It is a certain level of privilege to be able to bootstrap a lot of the time. It means that you have Either it's a bunch of savings, you made a ton of money doing something else, or a lot of the time your spouse makes enough money so that they can cover the wh…”

“They have no choice but to raise a ton of money And to get a ton of attention because the only way they win is by winning the market. They have to be the leader or they lose. They will run out of money. It won't work out for them. You have built a real busines…”

“When you're really trying to grow exponentially, bootstrapping is really is not the The best way to go about it. You really have to have really more of a structured and detailed plan. And that first starts out with having a strategy.”

“If you can go as long as possible and eat as much dirt, if not more dirt than we did I think that you'd be far better off as a business and as a human being than just succumbing to capital right out the gate without an MVP or initial idea.”

“So I think if you are in a category where there's a lot of competition and if some of your competition already funded, it's probably a better idea to get funding and scale rapidly because VCs are going to look for other players in the category. And if you are …”

“That's how you get filthy rich. You build a company that you own all of, you drive revenues, and you start paying yourself more and more every month in dividends and reinvest in the company or elsewhere.”

“The people that like bootstrap and want to brag about the bootstrap story do it because none of their other stories are working, right? So that's what they lean on.”

“And so my view is kind of you lose your bootstrap title as soon as you raise money and spend it at a rate that's venture based.”