First Time Founder

“It almost gives a new founder an advantage over a multi time successful founder because we have too much rope to hang ourselves. It's too easy to raise money and recruit teams against a big vision before we've gotten to product market fit, but the world doesn'…”

“I think most first time founders or founders who haven't yet had a good exit deep down, they're often playing not to lose. They're not playing to win because the reality is you put so much into a startup. It's your whole life. You're making very little money c…”

“I find first time founders are zero percent calibrated to that type of thinking, and a few years in it is very difficult for them. And then repeat founders, of whom I work with several, always have a very similar logic because they've seen what happens, even i…”

“There's other first time founders that fall into a little bit of a thinking trap, which is they decided that they wanted to get startup experience. So rather than joining a startup led by someone fantastic, they decided that they had to do it on their own. And…”

“Equity is the most expensive currency. This is the lesson almost every founder learns too late, especially first time founders. Every dollar you raise costs you ownership forever.”

“So the second time or multi time founders, we understand the value of structure. We understand the value of rigor. And going about in an organized way, much more, ah, than first time founders. When I was a first time founder, I was, ah, ah, I wanted to jump in…”

“One of the mistakes I've seen a lot of first-time founders make is, is they assume that an hour of coaching is as good as an hour of firing.”

“If you're an early stage startup and you're a new founder, they're going to spend more time doing due diligence that, and you need to be prepared for that. You know, you're a founder of a startup that's had several successful exits and have had several success…”

“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 …”

“One of my top criteria was complicated enough that other people won't copy me too fast. I think that's really important. If I'm a first time founder, I need to have more leg room.”

“You're a first time founder with no game experience. It will take you at least three times more than you think it's going to take because you're going to make mistakes with that money.”

“Sometimes younger, newer founders, first time founders don't fully understand the dynamic around that. And Especially when they're trying to make a case for a higher valuation and that kind of thing. They're not fully understanding that there's a balance there…”

“I think with the first time founder, especially one that went to a second tier school, like a good school, but not a great school. And some of that's in a second tier city. There's that chip on their shoulder. There's that aggressiveness, the pugnaciousness. T…”

“Most first-time founders average age is 39, 40.”

“First time founders. I think the ability to think from a clean slate to do foolish, potentially foolish, but on the other side, potentially visionary and transformative things, the hunger and the naivety that you described and a first time founder, I think out…”

“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.”

“I think for first time founders I am convinced that building a B to B niche media brand is the best way to go make your first buck.”

“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.”

“I don't like first-time founders like I like serial entrepreneurs, because you've just seen it, you know how to do hiring processes, you know what great looks like, you've avoided, you've seen the mistakes, you've made them.”

“I think as a first-time founder, you're actually much more okay, maybe because you don't know any better like me, to take on a lot more market risk, and so you can actually have really large outcomes.”

“You get pushed often by investors to hire executives or to scale the team, or we need, you know, We need, we re you raise all this money. You got to spend it. You know, we got to, you got to show you're serious about growth and building a world-class organizat…”

“But a lot of, in my opinion, raising money, the reason, especially first time founders do it, is it's actually just, it makes them feel better. It makes them feel like they're doing the right thing if they can convince people to give them money. And then they …”

“If you actually look at the research, what you'll find is that super founders, these are multi-time founders who've had material success in the past. Super founders are six times more likely than first time founders to create a unicorn.”

“I think choosing expedience over, you know, the hard things that, that actually Contribute to long-term value. You know, there's sort of quick fixes and sort of feel-good measures that can take the edge off whatever is bothering you at a moment in time. But th…”

“The biggest mistake that I see is that they start very, very late if the PMF is very strong. I've seen a lot of companies that have a very strong product market fit. And because of that, in the beginning, they just start getting a lot of revenue because big co…”

“A third time founder is going to raise ten million dollars out of the gate and they may very well deserve it. Whereas a first time founder may get one.”

“I would much rather invest in a founder who has never been a founder before so that I can teach them how to minimize their suffering.”

“There are a lot of first time founders who are phenomenal. Like I think, you know, you think about Jensen from Nvidia, he's been, I think that's his first startup. It's turned out quite good, right? So that's the sort of thing where you'd also don't want to so…”

“I think first time founders are actually better on average. Most of the best companies I've invested in are first time founders, not all.”

“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…”

“First time founders especially are usually very stubborn about this and they don't want to do it. It's like, look, you tell me what you believe. I don't have to be right. And I want to just double check that you're right. What, by however we do it.”

“I really don't like investing in first time founders. I just feel there's so many mistakes that you make when it's your first time.”

“One of the things you realize about founders is first time founders, they don't realize they have to be great at firing. They just think they have to be great at hiring, but you have to be great at realizing when your talent's not working out and identifying t…”

“Especially for a first time founder, I mean, if you're a proven founder, then this may or may not apply, but for sure, for first time founders, and you're thinking about your first 10 or 20 hires, I think you strategically have to go for the really high potent…”

“I think one of the like magical things about being a first time founder, especially in an industry that you don't know anything about, you're completely naive and you think that everything is going to work.”

“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…”

“I think first is when you start a call as a first time founder and it's your first call, see if the investor is introducing themselves first or not. And if the investor asks you to start pitching, then it is a big no, right? He's always sitting on a higher ped…”

“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.”

“You know, I'm not anti raising capital, but I do think it's a bad bet for most founders, particularly first time founders.”

“First time founders can actually take more risk on the ideas that they pick, because They don't have other startup friends, or they don't care as much. They're just working on stuff they find interesting.”

“Because they're going to have harder times typically raising money or hiring employees, they tend to have to innovate more. Like they tend to have to, they're constrained into building something good. Whereas like the lack of constraints so often lead people a…”

“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.”

“The reality is the kids that make new things work from scratch, it actually turns out that they actually have been deep in the domain for a long time. On almost every case, they've been thinking hard about the problem that they're trying to solve, actually for…”

“Category A is first time founders. Younger folks, you know, free product deals where the risk is significantly higher. Those deals we don't do beyond two, three million evaluation. Three is also a bit on the higher side. Usually it's around two million.”

“Actually, the average age in the United States is 41, I believe, for the, for a first time founder. And generally, the outcomes are better the older you are when you start a business.”

“And the first time founder, I'm like, I just wanted to say yes to everything and then just start building that. And then you end up going in 50 different directions and you're like, does it actually work for anyone specific? And so this time we're more intenti…”

“I think one of the, like, magical things about being a first-time founder, especially in an industry that you don't know anything about, you're completely naive, and you think that everything is gonna work.”

“I mean, plenty of giant companies, most of giant companies were started by first time founders.”

“A lot of founders, especially first time founders, They get to the 15 or the 20 employee mark before they realize that they've created a big hairball and a big mess and no titles and no, and people have overlapping responsibilities and all that.”

“As a first-time founder, especially as you're transitioning from this hunting for product market fit stage to really starting to scale and nurture letting go of product and finding somebody who you feel confident can fill those shoes is incredibly scary as a C…”

“What I believe first time founders really struggle with is sifting between, let's say that the half a million minutes that don't matter and the 10 that do in the year, and that 10,000 hours or 20,000 hours of practice of doing it over and over really gives you…”

“It's the biggest mistake most first-time founders do, right? They think, hey, they are going to fund us. Like, if you just listen to them, things are not going to work out. But it's never the case. You have to believe in what you're doing.”

“About 80, probably 80% of the folks that we back are first-time founders. It may even be 90%.”

“If you're a first-time founder, first-time founder, it's almost always better to start with angels or with the early seed investors. It's, again, contrary to myth and archetype, it's very hard for the first-time founder to raise, raise a straight A round. It's…”

“I don't think that, you know, a first time founder is going to be able to pull something like that off”

“Most first time founders are very bad interviewers, but very good at evaluating someone after they've worked together.”

“I think most founders, or many founders, especially first-time founders, frequently try to hide problems the company is going through, you know.”

“I don't think anyone's market ready from the get go. I think it's a flawed assumption with VCs where they try to imagine that, that these first time founders or any founders are going to just figure it all out.”

“So if it is a if it's a relatively new founding team that's never founded another company my advice is quite simple, which is to bootstrap as long as you can until you see some very clear traction, some very clear product market fit For the offering that you h…”