Opinion
Weinberg: Keith Rabois is a "giant doofus" regarding healthcare
“I think the guy is a giant doofus, and I would continue to hold my belief that he's a giant doofus, and I'll be very specific about why. I think Keith Raboy is probably a phenomenal technical investor, software company investor. It seems to me to be an amazing…”
Disclosure
Weinberg: Upper-middle-class family safety nets enable founders to take startup risks
“The reality is if you've got family wealth, and we're not talking about having to have tens of millions of dollars here, you can just be upper middle class wealth, let's call it. It makes it a lot easier to make a leap and to do a startup because in the back o…”
Opinion
Weinberg: It is naive for modern companies to claim complete societal neutrality
“To me, I think it's a little naive to think that a company can just say, we stand for absolutely nothing but our business. And maybe that was true 5060 years ago, but I just don't believe that that's true today.”
Insight
Weinberg: Companies should take socio-political stances before their business is affected
“There are things that eventually have an effect on the business, and you need to make a stand on them before they have that effect.”
Insight
Weinberg: Initial checks drive almost all value in venture returns
“I'm more and more convinced that it kind of doesn't matter. And actually by far the most important thing is did you get into the right great company in the first place? It's the initial check that drives almost all the value.”
Insight
Weinberg: Founders should sell under 5% of equity in secondary sales
“For the founder, I encourage them to take enough money off the table that they're comfortable taking a big swing at a bigger outcome. And for some people, just to put some numbers against it, some people, that's a million dollars. Because remember, you're goin…”
Assertion Supported
Weinberg: Venture fund returns are dropping to 1.5x to 2x
“You're seeing fund returns come down. You're not seeing five X, six X funds. You're seeing one and a half X, two X funds, and some that are probably even one X funds where you pile in and something goes really wrong.”
Insight
Weinberg: Companies can take public stances while prohibiting workplace political debates
“You can say, I believe these things are important, and also say to an employee base, however, don't bring it into the day-to-day office, don't bully people, and if you do bully people, and if you do push people based on their beliefs, we're going to fire you, …”
Insight
Weinberg: Tech companies are not democracies; control rests with CEOs and boards
“And Jeff is completely right. It is not a democracy and it's really up to the CEO. And then ultimately the board who controls who the CEO is.”
Insight
Weinberg: Second-time founders with small first exits are the best investments
“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.”
Insight
Weinberg: Operator Partners targets at least 2x next-round valuation step-ups
“We're looking for things where the multiple on the next round, not because I care about the markup at all, but because it shows Real growth and real value creation is more than like two X, let's call it as a baseline. So if I'm going to fund a company at a 10 …”
Insight
Weinberg: Wealth increases happiness by providing total flexibility over time
“I actually would say the money has made me happier. Maybe I'm not supposed to say it, but it's true, but it's not because, oh, I get to go around like spending it on cars and houses and stuff like that. It's just the flexibility to choose where you want to spe…”
Disclosure
Weinberg: Financial independence enabled me to speak freely on Twitter
“I don't need to ask anybody for anything anymore, I guess, and there's a freedom to that. I don't have to rely on somebody else saying, oh, I like this person, let me help him, and I guess that's a little liberating. And you'll notice I didn't necessarily have…”
Insight
Weinberg: Seed investments must project at least a 2x Series A step-up
“And we're looking for things where the multiple on the next round, not because I care about the markup at all, but because it shows Real growth and real value creation is more than like two X, let's call it as a baseline. So if I'm going to fund a company at a…”
Assertion Not checkable as stated
Weinberg: For every seed win with a markup, three or four fail
“Because for every one of those checks that you write that gets there, there's like three or four that don't. And it's got to pay for the ones that don't get there. And that's the venture math, right? Your winners have to win big and they have to pay for all th…”
Insight
Weinberg: Startup liquidity cycle times are now 10 years or longer
“I think the cycle times on these companies are so long. We used to say seven years, but I think it's actually much closer to 10, if not longer.”
Insight
Weinberg: Shifting existing customer budgets is easier than creating new ones
“It's a lot easier to go after a market where people are already budgeting for that type of expense, whether it's a business is already budgeting for it, And you're just shifting it from where they spend it today to what you're going to do. And that's a lot eas…”
Disclosure
Weinberg: Operator Partners exercises Series A pro-rata rights 100% of the time
“For now, what we're generally saying is if the Series A Is getting done and it's getting done at a price that we feel like is reasonable for the business, which most of them are, by the way, that's 80, 90%. Then a hundred percent of the time we're going to par…”
Prediction Not checkable as stated
Weinberg: Operator Partners almost never sells equity in secondary transactions
“So to be clear, we won't sell. It's just sometimes we may not buy. The prorata. But we're basically never selling in a secondary.”
Prediction Not checkable as stated
Weinberg: Multi-stage seed strategy will only work for top-tier funds
“And my guess, and I haven't modeled this, but my guess is, as with all of these things, there will be a subset of these funds where it works. Because they catch the five companies that they can continue to plow money into and end up putting five hundred millio…”
Insight
Weinberg: Founders considering preemptive rounds must do realistic bottoms-up milestone planning
“The conversation usually with them is a, what I would call like a private one-on-one of, take your sales hat off, For a second, take your hype person hat off. Cause as a founder, you know, you're selling every single day, whether it's to recruits or customers …”
Insight
Weinberg: The best investors accurately quantify their confidence levels
“Some of the best investors, I mean, actually, almost all the best investors I know will tell you, I don't know what I don't know. And here's the thing, they're able to quantify their confidence level.”
Disclosure
Weinberg allocated 20% of his first exit's wealth to startup investing
“After we sold the first business, I would say we tried to come up with a number. I think it ended up being around 20% where it's like, okay, if I lose this, it's not going to be fun, but I'm not going to worry too much. Like I'll be okay. And we felt like 20% …”
Prediction Not checkable as stated
Weinberg targets allocating 30% to 40% of his capital to startups
“This time around, we're looking closer to, like, 30 or 40% over time.”
