venture capital

“We were not a venture backable business. We got venture backing, which happens often, but we were a services business. We had no technology component, even over the three and a half years after raising money, we built very little technology.”

“I would see founders take when they were scaling a company with venture money was that it was really undisciplined and they were just spending cash all over the place. But at the end of the day, it didn't matter because they would end up like crashing the comp…”

“The VC podcasts that are out there, the tech crunches of the world, which are fascinating stories, but they're just stories and they're so far out of reach and so far out of context that they just don't really do anything for me.”

“The first year to two years of spend with a VC money is so wildly inefficient, by definition, because you're experimenting like crazy, right? So you have this massive amount of inefficiency between validating the idea, getting the right team, trying all these …”

“I often refer to that as, like, asking permission to start a company. Like, that's how I have viewed venture capital for a decade or more.”

“There was also just like a stress shift. Like we just became a lot less stressed out. I still worked extremely hard. We still all worked extremely hard, but there was a lot less pressure of like, Hey, you have to hit this one tiny home run of convincing one ou…”

“We had someone apply to tiny seed and we made them an offer and they verbally accepted and it took us a couple of weeks to get paperwork together. And in the meantime, they decided to take venture capital.”

“You can be a bootstrap founder and run yourself into the ground and work 90 hour weeks. I've seen folks raise 20, thirty million dollars of venture capital and work eight hour days. It happens, like, and be happy with their business.”

“Out of those, you know, average hundred investments that VCs make, the stuck in the middle is a really significant percentage. It's probably like 20 of those hundred, and a lot of those end up being some combination of, like, fire sales, or for more aggressive…”

“Venture capital is essentially an asset class that only makes money because rich people in the sixties and seventies lobbied the federal government to get capital gains tax rate applied to this certain type of investing, right?”

“Money can accelerate in the wrong direction also, which is something that we're seeing at my new company. We have competitors that are raising a ton of money, some that are good at what they do, and some that the money has twisted up their approach because it'…”

“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…”

“In fact, I saw a number somewhere and it was about, it was like 80% or 90% of venture capital goes to someone who graduated from Harvard or Stanford, or at least someone who attended one of those schools.”

“There was a study published in, and I forget the exact numbers, but it was like, 80% of venture capital, it might even be 90% of venture capital in any given year goes to people who have attended Harvard or Stanford.”

“And once you raise that level of money that they did, true venture, not tiny seed money, right? Not angel money. The clock starts ticking, right? You have to have a liquidity event. So they needed to IPO or they needed to sell at a certain point.”

“Like you can raise with just an idea or a deck or just a It's a team or whatever, but then the vision has to be big, and that does usually exclude you or preclude you from actually doing the kind of exit where like at 20 or fifty million bucks, because just th…”

“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.”

“A lot of VC ideas there, they don't work at small scale. That's the point of them, right?”

“VCs have the right, the information right, so they can look at your books, but do they want to every quarter comb through it and look at every expense? No, they don't.”

“I hate it when people raise VC on an idea. I hate it when they raise five million dollars when they're at 20 K a month, and they still don't have product market fit, and they're just gonna, they're gonna burn through the money, right?”

“Being anti-funding is like being anti-Hammer. Hammer is just a tool, and it's right sometimes, and it's not other times”

“So it is a category. It's not just a feature, but it's pretty small in terms of it is not a venture scale category. So if somebody came to you and said, hey, I want to build an entire company or lead scoring and I want to raise five million bucks. That doesn't…”

“I'm married with three kids, and I'm 39 now, so when I quit, you know, I was mid-thirties, I wasn't going to be someone that's going to go venture and work eight-hour weeks. I'm never going to do that.”

“Should at least consider venture. They're probably venture ready. And then about nine percent, I think, should consider some type of funding because it just makes it a little easier to get off the ground. And that maybe is angel friends and family. Maybe it's …”

“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…”

“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…”

“That was a big thing, was for them to start, A, generating deal flow, but B, to get the trust, I think, from people so they weren't a commodity, because they were a commodity before. It's kind of like, if I'm gonna go borrow money for my house, who's gonna giv…”

“And because of the length of these funds, most of the time, like a successful VC can raise several funds without returning any money at all.”

“I talk about my one nine 90 rule where I say around one percent of startups should go after venture, about 90% should bootstrap, and I think about nine percent should raise probably some type of funding. Maybe that's tiny seed, maybe it's angels, but it's like…”

“Yes, it does, without a doubt, and I think that this is the one thing that me and my co-founders hummed and hawed on the most. As I sat them down, because I deal with all the fundraising and talking with investors as the CEO, and I told them, guys, This change…”

“The VC, like, treadmill never interested us at all. We've all, all of us have worked at startups, and it's just very dreadful idea to me, honestly.”

“Prediction number four is that the AI VC bubble will not burst in 2026. Massive investment will continue without a dramatic crash.”

“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…”

“And I think this is one of the huge bootstrapper advantages that people don't deeply understand that doesn't get talked about enough is as a bootstrapper, I can run a business that let's say it like maxes out at two million. Let's say it never gets higher than…”

“Do you have to be venture fundable? I don't think so. If you triple, triple, double, double, I still think, yeah, you'll be overshadowed by those that are doing the lovable and the NN growth curves, right? The one to 15 to a hundred. But can you still raise ro…”

“So the fact that we had great human support is something like no VC wants you to have that because that's expensive and it comes out of your gross margin. Maybe it means you're not, you're quote unquote, not a software company because your gross margin is less…”

“I think that we've benefited from the millions of dollars that this competitor is pumped into advertising in the market. And then when they Stumble and fall and aren't as good of a solution, then they go looking for another point of sell system. And so we've b…”