Second Time Founder

“And I think overall we've done a little better on second time founders who didn't do that great up front. They didn't, they did okay, right? It's life changing. Like the first million dollars is so life changing. But they're really hungry. They've learned some…”

“A second time founder is like, forgive all my weaknesses. I'm just not even gonna try. I'm just gonna be really good at my strengths. And I'm gonna hire other people to do all the things I'm not good at. And that is way more effective.”

“And like, I think that probably a second time founder is kind of the sweet spot. Like if I were a VC, I would often be looking for like second time founder where the first thing they'd gotten some traction, it wasn't like a total dud, but it wasn't like a runa…”

“And as like second time founders, you know more. And so you sort of believe that these ideas are better.”

“I think that is another trap is that as second time founders, there is no shortage of capital that is chasing you. And if you're not discerning, the capital won't be.”

“In case of second time founders, they are more conscious with choosing problems. They're more conscious with building teams. Right. And very picky about both of these things. Whereas first time founders are very, very eager to build the product and give it to …”

“Lots of second time openers that were able to raise lots of money very quickly came down with a top down thesis on, on a market. Right. And Never really got to product market fit because the team that they were able to build because the capital they could rais…”

“In our portfolio we see equal number of second-time founder companies not working out, and these are like super second-time founders built fifty million ARR companies. Right. Right. Their company's not working out as equal to first.”

“So I think when you have that reasonable win and you're coming at it again, you come really prepared and you come with this feeling that like, I'm going to make a difference, an even bigger difference.”

“So the second time founders, you've already seen them do something so they can raise, as we've seen, second time founders raise huge seed rounds. First time founders, if they do well, raise better series A and B.”

“First time founders brag about how many employees they have, second time founders brag about how few employees they have.”

“First time founders are looking for investors that add a lot of value. Those that are second time around understand it, bias, and skew wildly towards the passive.”

“Again, one of the reasons second time founders do so well is they would be less affected. No one is unaffected, but they would be less affected.”

“I would bet your second time founders don't they hire slower is my guess because I just think it's an easy way to like burn up opportunity and ultimately lead yourself in a position where you might have to riff.”

“First-time founders think that the best way to get their team to follow them is to be liked, but really second-time founders recognize that the best way to get their team to follow them is to win, so that's more important than being liked in the moment, and th…”

“I always say, like, I would so much rather invest in second-time founders and pay a premium, because I think the lessons that you've learned prevent you from making so many very significant mistakes”

“I find like second time founders, especially, I get it, you're selling cash with some advice, which is great, but it's a deal.”

“You shouldn't undermine the benefits of being a second-time founder and the benefits of having money in the bank so that you can put money to work in some ways may not be as efficient, but are going to help you get to market faster or build a better product or…”

“Second time founders are in more self doubt than first time founders, because as first time founders, you have nothing to lose except your time. And the opportunity cost. In second time founders, they are overthinking on their reputation. So if they fail secon…”

“There's plenty of capital available for people who are second time founders and the first one was not a successful exit.”

“And if it's not the right fit for whatever reason, you just, you move on it. And I think that's something a second-time founder will do that a first-time founder has a lot of trouble doing.”

“As a second time founder, it's just as hard to talk to your users But it's 10 times easier to talk to experts. So almost by extension, it's like even harder to talk to your users.”

“You know, one of the things we've been saying is like the lows are just as low, but the highs aren't as high.”

“Whereas a first time founder, the only way you're getting your first few users is having a really great product and being really great at selling it. And I think you can just get a little bit lazy on that front as a second time founder.”

“What I've also seen for second time founders is that oftentimes for an investor, it's more of a catch. It like helps you build your reputation in your firm, or it helps you get the deal approved. And like, so oftentimes there's like internal political reasons …”

“I'll say you find that eventually though, it's a little bit like taking out debt, honestly, where it's like maybe early on as a second time founder, like maybe the seed rounds easier, maybe even a series A is easier, but the later, the longer you work in your …”

“Whereas if you have some financial independence, like a lot of second time founders, you can think bigger and actually like play out the implications of the business that you're going after and try to build something that's optimized to get big from day one.”

“Another very specific type of startup that seems to be suited to second time founders are capital intensive businesses. And by that I mean, you know, any startup where like more money raised or just more money is a strategic advantage. Second time founders who…”

“I have found that second time founders who had a good but small first outcome are by far and away the best people to invest in.”

“Second time is always better because they have either become very successful, or they have learnt at somebody else's cost.”

“In reality, two things are different. Investors, I don't think for a good reason, significantly bias for second time founders. Significant bias towards second time founders. And there's something you have to understand. Second, if you've been in the valley for…”