Union Square Ventures

“I've always been in or around New York, and as a builder, when I was building Anchor in New York 10 years ago, I got to meet USV, and I had an incredible, despite them passing, had an incredible experience. Started a very, very long friendship. I ultimately be…”

“At USV, we're really interested in the Rebel Alliance. This new universe of open weight models and open source harnesses and distributed compute and agents, right? Human aligned agents.”

“So, USV, again, I think has never been afraid to take a position, and I think USV maybe, ah, did not invest in any of the big model layer companies.”

“USV a few years ago invested in a great company called Radiant, which is building small nuclear reactors that literally come off of a factory line.”

“We have a bet in a company called Rune. Amazing company. Have you heard of Rune? They're building micro data centers that sit directly next to generators. You know, wind farms and things like that to solve the portability issue.”

“At USV, we like to bet on businesses that obliterate, that literally obliterate markets and existing business models. And so, you know, we're, we actually don't do a lot of enterprise investing for this exact reason.”

“And I think when you're small, you kind of have to pick Your spots. You have to have constraints and focus on a small number of things, and so I think to the extent that we see things different, it's because we focus really, really deeply, and for a period of …”

“We think it can be a lot bigger than it is now. And so, for this one, we're not gonna be ownership focused. We're just gonna, we're gonna put a check in.”

“For us, the fund that we're investing out of now, the core fund, it's a two hundred seventy five million dollar core fund”

“I asked him, what are a couple of the biggest lessons? And one of them was, never pass on price. So Fred says, never pass on price.”

“Just to bring it back to the USV strategy, I think for us, again, if we're investing a little bit later stage, we need to really believe that it's a market winner, and the multiple can be very, very, very high, and in that case, I think we can be a little bit …”

“You can't project your own ideas on the founder. Sure, you can offer ideas, of course, if the founder wants, but especially as a former operator, you know, you often think, Oh, I know how this business should be built, or I know how this product should work. A…”

“When I first started this job, I would have said product, market, founder. I've completely flipped that. Now, founder, market, product. I think that the founder is the most important thing.”

“Also Union Square Ventures funded, and I'm sure that had something to do with USV being more comfortable with me, because I certainly didn't have a track record.”

“What I would do is I would join Union Square Ventures. I would join an institution that has a really storied name, but doesn't have particularly strong leadership. And I would become the leadership for that organization.”

“The models feel like they're getting fatter every month and they're sort of eating away at the edges of what you can do with them.”

“Like Andreessen Horowitz, USV, Fred Wilson is on our board and a lot of other, like, really, you know, awesome investors.”

“The lawyers quoted him 50,000 dollars, and he was like, I think you should do it for less than five, and when they said no, he took his entire history of his closing binders, uploaded them into his, ah, you know, AI knowledge base, and had the AI essentially f…”

“Union Square broadly, and we're not an investor there, we wish we were, but I think they've perennially been the best at selling, and they've got a very strict protocol that they run through, you know, from years eight to 12 on those funds, and with those foun…”

“We may have to cut this afterwards, but I think we only had one offer. It was Union Square or back to university.”

“We actually did get a lot of interest from Silicon Valley VCs at a time, but they all made it a requirement To move to Silicon Valley. So we're like, you've got to move here, right? Like, when are you going to move here? That was the, always the question. Okay…”

“They, like, they build their firm off the internet. They hire off the internet. They do not hire off of, kind of, personal networks or anything.”

“USV, I think they're good at a lot of things. They are very, very, like, market and idea driven. And, you know, like all investment theses, sometimes it works, sometimes it doesn't, but I think their, like, fundamental world view to me was if you pick, or if a…”

“What I did was I took my bonus basically lived off of it for two years. So that was kind of my grad student living and taught myself to code.”

“And I think again at USV I'd seen that actually starting the company isn't the hard part. That's, you know, shockingly easy. The hard part is like in year four when it's not really working, but you've raised this money and you have employees and you're still d…”

“The other strategy is pick something, go deep in it, and be the expert where no one else is. And in the fall of 20 12, I recommend you choose crypto.”

“Most people actually try a bunch of stuff, and eventually something might work, but it's like, At best thing five, and it might be thing 55, but no one really talks about that because it's both because it's like painful and kind of not fun, and you know, it's …”

“Would Coinbase not have been successful? If they hadn't take money from Andreessen Horowitz and USV. No, I think they would have been just as successful.”

“And then we raised a series A with Union Square Ventures in 20, 22. And then a little over a year ago, we did a series B with Andreessen and raised a forty-five million dollar round. So when you add all that up, we've raised about sixty million in total ventur…”

“USB doesn't really love to invest in companies that require permission to do the thing that they want to do. Like we don't like to have to help entrepreneurs slog through dealing with a bunch of gatekeepers. We like when they can go directly to the end custome…”

“I've seen this firm support companies when they need to be bridged, when they need to, an entrepreneur needs USB to do its prorata in order to look good or to get somebody else on board a hundred percent of the time.”

“Part of it is it's a small fund, which means that like, we don't do heat seeking things. Like if a company is extremely hot and kind of down the middle and consensus, and it's, you know, someone wants to write a thirty million dollar series, a check another th…”

“I mean, they've now told me, look, we'd never thought this would work, but you had a really good track record. So why not?”

“It's 3.3 million, which at the time, this was a normal series A. So it's three million dollars from Union Square Ventures and 300,000 from a combination of Tim Ferriss and Ashton Kutcher.”

“In many of the best examples that I studied from USP's history, it was very much not the case, and so I think a lot about where can I develop strong perspective that may not be the hottest thing of the moment.”

“Impact in the portfolio has actually come from existing portfolio companies application of it, which has for many of them changed trajectory or meaningfully evolved their business.”

“I think we have way increased mortality rates.”

“I think we might see a little bit of M&A, but I actually think that M&A is really hard right now. I think you're just going to see a lot of them unfortunately die because M&A works if some other piece has a lot of cash, right? Or has a lot of asset and you're …”

“I met one investor during our seed round, Albert Wenger from Union Square Ventures, who wouldn't invest at that point in time, but we really, like, hit it off, and he's also from Germany, and we, like, just decided to stay in touch, and I think it was more of …”

“I'm purely just investing my own money, but I have all infrastructure and a whole firm that does that. So it's like, it has historically been a single LP fund. Everyone has carry. It's no different than you and Square Ventures or Thrive or anything else. Just …”

“I think USV doesn't get the credit that it deserves. I think it should be in that pantheon of greatness that sort of Sequoia and Benchmark are typically put in.”

“This is how Union Square Ventures became Union Square Ventures. Our Foundry Group became Foundry Group because blogging, blogging, and then Brad and Jason writing the book on venture deals.”

“We don't have a growth fund, for example, we have a fund that we call the Opportunity Fund. And why do we call it the Opportunity Fund? Because things we put in there need to feel like they're actual opportunities. And so it doesn't have any revenue requiremen…”

“Because it forces discipline. Like if you raise one big fund, you can be less disciplined than if you have three vehicles where you have a very specific thesis for each vehicle. And each time you can ask yourself, does this fit with the thesis? Or am I just, y…”

“No, I mean, look I think we have brand new, 20, 22 funds. We have a new opportunity fund, a new core fund, a new climate fund. And so we're probably not going to be in market for a while because we've kept our funds very small.”

“If you have raised at a high valuation, you, and you have a lot of money in the bank, you have to get a cash flow positive. It's the only safe place. Literally the only safe place is cash flow positive.”

“By not hogging the economics.”

“I just, I follow a lot of honestly what USV does of like try to learn. I think they're the best pound for pound fund in the world both operationally and in every way.”

“And while both can certainly work and there are certain, and there are notable exceptions here, like union square ventures, for instance, which works very well as a partnership structure, the more durable firms in my experience often have very clear leadership…”

“I think there will be a lot of folks that go away in this cycle. I watched it in the last go round. You know, Spark and USV and all these firms didn't exist before the last cycle. And they really made their names coming out of the O eight crisis. And on the ot…”

“There are a couple of people out there like Chris Dixon at Andreessen Horowitz, Fred Wilson at Union Square Ventures that they're making these things. But anybody else, I don't think any of us knows which one is going to win long term.”

“Your union square ventures. If you're Sequoia, the fact that you did the deal is the reason it's no longer contrarian.”

“Brad and I tried to raise a fund together after the .com bubble burst and we couldn't get it done. And so he had to bide his time a little bit. I had to bide my time. And then he teamed up with Fred to in 2003 to raise USV, the first fund, which got going in 2…”

“And I think today, if you look at the investments we've made in the last few years the vast bulk of those revolves around subscription businesses where we think the incentives between the company and the end user are actually aligned, right?”

“It was 3.3 million, which at the time, this was a normal Series A. So it's three million dollars from Union Square Ventures and 300,000 from a combination of Tim Ferriss, and Ashton Kutcher.”

“Over the last 12 years, Gabe has scaled DuckDuckGo to doing over 1.6 billion searches every month, a team of 83 fully remote full-time employees, and also raising funding from some of the best in the business, USV, and also, most importantly, being a profitabl…”

“We were funded by Union Square Ventures, and the average founder at Union Square Ventures is older, and more than half of them already had kids”

“90% of the companies Maybe 95% of the companies we back are built on AWS.”

“That's why largely we're not investing in a lot of dApps. I mean, we are playing around with NFTs and games for all the reasons you raised.”

“Union Square Ventures, Benchmark, or some other exceptions to what I said.”