The Ledger, every show

“No, not a chance. They go to five to six percent. Every real estate investor that we know is bankrupt. They're not hanging on. They're broke and dead. And every home builder in America has no customers. That's a fact.”

“I don't think that the way you build a big company or the way you get a big exit is by investing in the most ambitious companies, growing the fastest. Those are also the companies that crash into it.”

“I think if you're, from the get-go, if you're talking about creating a category, you're making a mistake. I think a lot of times when we talk about category creation, it's in retrospect that we see that a category was created. It wasn't started that way.”

“No, at seed I don't think so. I think it distorts everything. Everything from the go-to-market model to how you hire, to the offices and the culture you're creating, it's all wrong. I, so I completely disagree.”

“There's no question that, at the end of the day, you, most of your returns are gonna come from very few deals. It's not gonna be spread evenly. That's a fact. The question is, can you recognize it early on, or can you recognize it really at any point? And I do…”

“Being more ambitious, raising more money, a higher valuation. But that's actually not the way in which you build something bigger.”

“I invest in people who I think can raise money even when they're not, even when they don't meet their plan.”

“I try and make sure my companies I back never raise at valuations that they want to sell the company at, and I warn them of that.”

“No, I don't. I don't do them, but for different reasons. I don't do them because the way they rationalize needing twenty million dollars is because their six competitors also raised twenty million dollars, and in that sense, they're absolutely right.”

“Well, I know it's hard to sit out in an entire market, and it feels like AI is like the equivalent of cloud, and so I'm not suggesting sitting out of anything related to AI. Of course not. I'm talking about some of the very mainstream type AI use cases, especi…”

“I don't mind having missed an opportunity to invest three more million dollars in a company that could have generated another thirty million dollars of gains, but I do worry a lot about doubling down in a company, investing another twenty million dollars, and …”

“When you invest a lot more money at a lot higher valuations you actually end up behaving a little bit different as a board member even when all of a sudden you have a hundred million of cost basis in a company, in which I do have several companies where that's…”

“100%. That is exactly what's going to happen over the next 24 months. Various ways in which to get, you get your one X. And when you know that you want your one X, you want it now. You don't want to wait two, three, four years from that.”

“You always want the previous deal. This is the stage where you always want the previous deal. You want what they off, what you could have had before, and you have to preempt that, meaning you have to realize that it only gets worse from here, and so you actual…”

“And so I would say at least six or seven times I've had exits where, I mean, the company Was almost worthless. You know, less than two million dollars of revenue, and we had offers that shockingly good.”

“Central banks, in their zeal to destroy volatility, they've created so much correlation that it's really hard to find anti-correlation is kind of a way to think about it.”

“I worked back then at a time where it was much more adversarial relationship with entrepreneurs. The VCs kind of acted as if they knew what they were doing, that they knew the right way. A lot of these VCs were former Maybe entrepreneurs themselves, or at leas…”

“There's a higher likelihood that that partner from that VC will be on your board than your co-founder will, just statistically.”

“But if they're so certain about the idea at such an early stage, to me, that's a bad signal.”

“Like I said before, there are two types of second time entrepreneurs. There are those that don't recognize the luck that was involved. They think that building something big is just more ambition. And I steer clear of those.”

“Insiders are just blinded by convention, by knowing a little bit too much of what hasn't worked in the past of where others failed. Naivete is a strength in these cases, and if you have the right entrepreneur who, again, is self-aware and perhaps also has a ce…”

“I think where category creation makes sense is when they've identified a new type of customer or a new type of buyer.”

“That that it's a better arbitrage opportunity to be the lone player or the first mover in a even in a smaller market, even in a niche market, than to be the number two or three in a large market. Because a number two, it's like a gladiator competition. Number …”

“I mean, any early stage company that's raising fifty million dollars, I don't know what stage that was that you were thinking about, it's inappropriate. Those are not the type of invest, of entrepreneurs that I back.”

“It's rarely growth at all costs in my book that just doesn't last, and it's very painful when it's, when it stops.”

“Trying to focus on KPIs when a company has half a million dollars of ARR also doesn't make much sense. Those numbers are, if it's, if they're fantastic numbers, I say it's anecdotal. And if they're horrible numbers, I say, well, we need a bit more scale to get…”

“In both cases, I received what would be politely say very lukewarm feedback from the partnership. In fact, in the case of Wix, it was outright negative feedback.”

“The best thing about pattern recognition over time is that you recognize what won't work. It's not what will work. Now, if you recognize what won't work, it will help you avoid spending time on, on bad deals, or bad entrepreneurs, or if you're on the board of …”

“So I'm much more interested in not making a mistake with a hire than making sure that this is the Best possible candidate we could hire.”

“I make it very clear to the entrepreneur that I'm choosing them more than I'm choosing the market or the particular product, and that I'm choosing them because I'm also not just choosing somebody that I hope will succeed or want to succeed, but somebody that I…”

“Down rounds are not problematic. Much more problematic, again, are valuations that that are essentially in exit territory, or far in excess of exit territory. It's really hard to recover from that.”

“In the context of Israel and business, I think business has bottomed out and things are getting better for now.”

“I do worry, for instance, in venture capital that there's still far too much capital to make this a business that we can all do, or even a lot of us can do well in.”

“Oftentimes, 90% of the value that Is created in the company happens in the last 12 or 18 months of the company's life”

“When they're starting out, I tell them, just get points on the board which is to say again, don't try and back the biggest thing. That's just not the way it works. Just get some exits.”

“I think it's more about thinking that you could be number three or four or five in a market and still succeed. I think that's such a mistake on the part of entrepreneurs, investors, and even employees who join these companies. Obviously there are exceptions, a…”

“All of us look at this now that I'm in this seat is yeah, let them go work at like one of these bolts bracket firms. Let them train these people for us. And then we'll take them, right? Like, we don't want to train any of these people. Like, that's a waste of …”

“I think it's not that great for the sponsor. It's great in the sense that you get a huge amount of capital in our management, you get all these asset management fees and all this other stuff, but I think it makes you do stupid things. The alignment's all off, …”

“I think it's still a worthy debate for the entire industry to have as to whether or not the drive into these extreme risk management parameters is a good thing. I believe it causes everyone's returns to go down, but I think that's a choice.”

“Frankly, except for very few traders in our industry, I think it's kind of where macro people should try to turn to. I mean, I have a strong view that discretionary people Should really push deeper that direction, not shrink away from it.”

“So that sort of coquates to like a .75 sharp, which is probably as good as one can hope and macro. I mean, everyone wants to do a one, but nobody will get there.”

“Your excess returns are going to come through Timing, asset allocation, and then leverage. Timing's the hardest. It's what hedge funds basically are asked generally to do, and I think we can all agree with the number of managers that exist today, and then they…”

“One of the things that I eventually, ah, did myself when I started at Bessemer, ah, this is in 2000 and seven, was to, Take a very different approach to take this kind of partnership type of approach with the entrepreneur, because I realize what they really ne…”

“The key for looking at first-time entrepreneurs is, is, is identifying somebody that you have chemistry with that you have back and forth from, that they can learn from you, you're learning from then. It's also people who progress very fast on the learning cur…”

“As much as I am willing to be contrarian, I'm not willing to invest in something that others are not going to fund. So I need to find, it's a fine line, but I need to find something That perhaps is not mainstream, perhaps is not and yet a headline in TechCrunc…”

“The easy ones are Wix and Fiverr for me, because at the time, You know, I was the first institutional investor to come in both of those.”

“I accept that sometimes I have a lot of biases towards certain types of entrepreneurs, and I can't always invest in the same Adam Fisher typecast entrepreneur that even though that works for me, it doesn't scale and I'll probably miss out on some very good one…”

“The analogy that I use is that we're not like you know, the entrepreneur is the captain of the ship, but we're not next door, you know, shouting which way to go. We're like the lighthouse. We just tell them where the rocks are so they don't crash, but we actua…”