Bootstrappers

“I think it's dangerous for a bootstrapper to have a feedback loop that's this long, because you're just going to waste years of your life. I can't imagine taking, that's such a risk. The opportunity cost of this is significant, so I would either be looking for…”

“Like, the real SaaS-pocalypse is the big companies, the big incumbents. They're the ones who have raised their prices so much, maybe a little too much, Because they have to grow every quarter for Wall Street, right? So they have bloat, they have legacy, they h…”

“I know of very, very few examples Of bootstrappers that have been successful when folks don't even know that they're not even really aware that they have that problem that needs to be solved.”

“And as I reflect on it, I'm like, I feel like these have always been the bootstrapper advantages. So in a sense, it's like, even though so much is changing in our industry, I think ultimately what allows us to succeed and set ourselves apart is kind of staying…”

“I think bootstrappers think more like, okay, if it's not working, if you need a pivot, let me try just like running a few ads to this market. Let me try just changing the marketing and not too much with the product and let's see if it gets traction there. Wher…”

“Dude, if you have a hundred million dollars in ARR and you're bored, you should go roll your own hardware. You know what I mean? Have we, have you and I already talked about this on the podcast or has it just been private where it's like, come on, man, don't, …”

“Versus a book like Shoe Dog or Zero to One. I enjoy those books. I've read them both. They're both entertaining. Neither of those will help you as a bootstrapper. You'll probably take away almost nothing From them.”

“My experience is that the bootstrappers tend to be market insiders who have identified a problem, go out, hire a dev team, and they already have their go-to-market figured out. That's how they're able to bootstrap. They can get cash flow from day one, do it on…”

“And I think, you know, I think we're about to see kind of the renaissance, the bootstrapper.”

“This is why freemium, it's not a never for bootstrappers. It's a by default, don't do it. What do you do if there are many free signups and not many paid conversions? Don't do freemium. Listen to this podcast and in general, don't do freemium.”

“The only SaaS company I ever have seen that actually split tested pricing was Zapier, and I'm sure someone else has done it, HubSpot maybe. I mean, there's a few, but as a rule, like bootstrappers, you don't test pricing. You take your best guess, and you make…”

“These days, all, almost all of those reasons still apply about it being less competitive, about you don't need to be the best marketer in the world, you just need to be a better marketer than the other folks in your niche.”

“People don't judge bootstrappers for raising money like they used to. They would call them sellouts and you know, that kind of stuff. And I just don't see that happening.”

“And so if the legacy trade organizations and associations you're talking about have network effects, as a bootstrapper, I personally would be very wary of trying to unseat those.”

“Trying to be a bootstrapper and rely on luck is super dangerous, and we see some people doing it. We see in our space some founders who kind of get lucky, and then when they go to do it a second or third time, they can't, right?”

“This isn't something that you can just try for 90 days or 60 days and expect a result. This is something that You have to have a serious timescale. Like, I don't know if it's five years, but you know, at least 12 to 24 months of like, hey, I'm going to go and …”

“I think it's totally feasible to spend 20% of your time in your first year of entrepreneurship as a bootstrapper building the product that's going to one day liberate all the rest of your time, right? Like it can really be, you might spend 80% of your time jus…”

“If you want to stay small, you're a bootstrapper, you're an indie hacker. It's only good if a competitor builds something like you, because they have the money to create awareness.”

“Usually you just can't afford owner level thinkers. They're just very expensive. They often become co-founders because you need to pay them in equity.”

“That was the bootstrapped model, and I think that makes a lot of sense for bootstrappers, especially if you're a solo bootstrapper, because, you know, do you want to support a large number of customers that are on free Plans. Or do you want to support a smalle…”

“With that being said, there's one disadvantage, I believe, what all bootstrappers have. We're kind of like a lonely wolves, you know, we don't have any experienced board of directors, sometimes we don't have many people we could talk with, and this is like com…”

“Bootstrappers are some of the most miserable people I've ever met. And I don't mean like they're bad people, but they never take the time to enjoy the fact that they've built some amazing things. Like I know people who've had nine figure exits who are just mis…”

“That's the pattern that we've seen in bootstrappers who get it done. Usually it's one or two-person teams.”

“These are senior level people who can get a lot of things done, but they're very expensive. They tend to be a hard to find and be out of, you know, the price range of a lot of bootstrappers. You know, if you're going to hire a contractor or someone who's going…”

“If you're a bootstrapper trying to just get your initial version of your product off the ground, you do not want to be like mimicking what those teams are doing because they're implementing things so that they can scale it up to a team of 500 engineers handlin…”

“I think the bottom line is, you know, most startups and most SaaS apps do sell at some point. I mean, the vast majority, they do sell within whatever timeframe we could define seven to 10 years. There are very few bootstrappers who are still running the same S…”

“Most of the successful founders I know don't have a lot of patience when it comes to their business. I might go so far as to say that for a bootstrapper, patience can be dangerous. It can lead to complacency and comfort with the status quo. There's something a…”