Trae Stephens

“I tend to think that that position is pretty morally bankrupt, but I guess you could have that position, but ultimately I think that's what it is.”

“You have to hire a strong government relations team because your customer is not the budget appropriator. Like they're not the same. So you have to be able to work the administration. You have to be able to work Congress. You have to work political appointees …”

“There's a long history in Companies that are doing business with the department where they have these massive advisory boards of retired generals and things like that, and it was just clear that that's never worked, and so that was never really part of our str…”

“Cognition, the AI coding company is a large position for us.”

“The goal is take humans out of dull, dirty, dangerous jobs so we're not putting our, you know, men and women, brothers and sisters, in horribly dangerous situations and become as accurate and precise as possible. And that's really what Just War Theory is all a…”

“Pacifism as an idea is only possible inside of a governing system with a monopoly on violence. Like, you can't be a pacifist without a government monopoly on violence.”

“There's a lot of surveys that show that for the first time in modern civilization, more men in the most recent generation in Gen Z going to church than women. It's like that has never happened before.”

“People in D. C. C. S. You know, a real company, not a startup anymore. And I think that that just gives us additional leverage to go and pick up bigger and bigger contracts over time.”

“Going out and raising these mega rounds at massive prices. It kind of reminds me of the self driving car phenomenon where you had these companies that understandably were capital intensive and it was like, man, if it works, it's going to be great. Everybody's …”

“Everyone agrees that these things are good. But what that means is that the categories end up being hyper competitive. It's like so consensus. There's so many companies being built.”

“Only fans you know, gambling, I think falls in the feels good is bad camp. This is like society has somehow managed to convince ourselves that there's some like freedom of expression or something like that that should be protected. And I agree, like freedom of…”

“It turns out that like, you just, it's basically impossible to get into good schools if your guidance counselor doesn't know all of the admissions officers at the Ivy league schools or whatever.”

“I'm not sure that it is, and I'm willing to go out on a limb and say that spending your life working for a consultant firm is probably not the path to having the most enlightened experience.”

“It takes about 500 pitch meetings before you really know what you're doing.”

“Twenty million sounds low. I mean, if you only lose twenty million dollars figuring out how to do this, then that's pretty good.”

“The first big check that I wrote at Founders Fund was Flexport. And no one was thinking about Supply chain logistics in 2014.”

“So when I wanted to make the flex board investment, I had to kind of go through the gauntlet and answer a bunch of questions from the team and pound the table. But at the end of the day, they were like, we made a bet on Trey. Trey has high conviction in this. …”

“And this is going back to that earlier point I was making about heuristics is that you can't constantly convince yourself that every Exception is actually an exception. Usually it's just wrong. Usually you should just follow your instincts around the heuristic…”

“The thing that I actually like a lot less is the false sense of scarcity and urgency. And that was like what was happening in 20, 21, where the founder was saying like, you have 24 hours. I have a, I have an exploding term sheet. I'm going to pull the trigger …”

“Like I was on the verge of just leaving venture capital.”

“And I think now in 20, 24, looking back on what happened, it's very easy in retrospect to say, Wow. We really let that get out of hand. And now we've got, we have to do a recap. We have to do a down round. We have to do all this crazy structure, but we're doin…”

“Do I think that doing that in the structure of like gather a bunch of investors on your board is the way to do it? No, I think that's really stupid.”

“Our core vision is we just want to invest in the best founders, building the best companies that are going to be category, category defining. And I think you can do that through a very traditional venture model of, can we get a check into the series A and can …”

“This is by the way, the biggest risk of taking seed money from an institutional fund is that like doing your prorata is super lazy, doing more than your prorata is actually a signal in If you're not going to have real signal, if you don't have high conviction,…”

“All upsize maximization. No downside protection silly. Like I think if you go back and you look at our portfolio, like whether or not we got our money back has never impacted fund performance. Like the only thing that moves the needle for a venture fund of our…”

“The biggest lesson that I've learned from these is that there are times where I've gone in and I've said, this has 10 X potential from where it is right now, and therefore it's probably worth making a bet. And I look back on some of those investments that I've…”

“No, because I think the best founders are going to pick Really strong markets and they will increase the probability of success even in like a middling market. So I think the founder has to be the atomic element always, but obviously like there are going to be…”

“If you're like a multi-time successful entrepreneur and you're starting like fairly simple, trivial enterprise SAS company, like shame on you. Shame on you. Like, you need to go big. Like, have some vision for how you can impact humanity.”

“The founder is the atomic element, a really great founder and team are going to be able to pivot their way into strong product market fit. Whereas a great idea with a weaker founding team are going to get stuck and will likely spin out.”

“I would say the most common example is where you have a founder that doesn't build a, like a, Diverse enough set of skills around them with the rest of their founding team or their executive team. And they assume that their, you know, specific superpower will …”

“Definitely in the first six months I think you can get a sense for momentum. There's almost nothing as important as momentum in startups.”

“If you go back and you look at the best companies in any portfolio, they were kind of the best companies at every stage. Like they were incredibly awesome at A, they were incredibly awesome at B, they were incredibly awesome at C. Very rarely do you see a comp…”

“Did I have like some super crazy interest in supply chain and logistics or a thesis in supply chain and logistics before I invested in flex work? No, of course not. Like I needed Ryan to like convince me of the timing to the market.”

“It turns out that the core monopoly investment that won is the only one that mattered in the rest of the category matters a lot less. So if you have some vision for what the future looks like and you're looking for a company to invest in that's doing it rather…”

“Can we afford to shoot a two million dollar Patriot missile at a 150,000 dollar cruise missile or kamikaze drone? No, it doesn't make sense anymore.”

“We have really just allowed Our Western political system to just be destroyed by mediocrity. And, you know, we have our standards for our elected leaders are like bargain basement level. It's really pathetic. And I don't know what it's going to take to convinc…”

“We should keep in mind that the co-founder CEO is Brian Schimpf, who is the most brilliant software engineer I've ever worked with.”

“I think it would be better and more interesting if it were because I think that most of the advice that I've gotten the most out of is from existing founders or former founders or operators. Like they're the ones that have lived in those shoes. They're the one…”

“Hype is not aligned with outcomes. In fact, it's often negatively correlated with outcomes. And so when something feels super consensus, you should be running away, not running toward.”

“And so as an investor, when I look at something and I'm like, yeah, this is a vice investment. Maybe it's probably going to make a lot of money because it leads to addiction or loneliness or You know, whatever. I don't want to be involved in that. I don't want…”

“I am deeply committed to the idea of civil service. And I don't know if it's in five years or 10 years or 15 years, but at some point I want to be back as a public servant working for the good of our nation and our allies and partners.”