The Ledger, every show

“Web three comes along, which is basically just a new stock market, right? And which is why the argument about whether the securities or not is silly. They're just stock, like they're securities for sure. People are buying and selling them, and everybody's argu…”

“This whole angel investing phenomenon is partly due to this Vanguard S&P 500 and the way the public markets are working. So people that call this a bubble I don't really understand the full scope of money and money flows and the whole ecosystem of investing, b…”

“So basically all that's happened in the last 12 years and beyond is the unbundling of Vanguard. Right? I want to own the S&P, 400, less these six destructive, I'll own the S&P, two 94.”

“There should be no Robin Hood. There should be no any of this stuff. It should all still be CNBC and Vanguard and Goldman Sachs. They just didn't give their technology. They hoarded the technology.”

“There's no such thing as passive investing. Vanguard is a very active portfolio. Every month or quarter, they kick out poorly performing companies, so it's a quant fund. So people are really buying an active portfolio. It's just packaged as passive.”

“If you like the CEO, and you like the opportunity, and you like the market, and every single thing about this says yes, and the only reason you say no in a private, this is private stuff, not public check, and the only reason you say no is the price, well, you…”

“I don't think community is a VC fundable idea, much like media has been, in general, a terrible, these, we need community, we need media, is that, does that mean it should be VC funded? No”

“If you build on someone's platform, or if you build on someone's roads, or if you build inside, you know, in someone's backyard, be prepared to be sued or screwed.”

“Speculation has become entertainment, and so gladiators, when the Romans had all this time, And they were fighting wars and moving people. People in Rome just said, you know what? We got a lot of fucking time. Let's have people kill each other and we'll watch.…”

“The last 20 years, you gotta be really, make really bad decisions to fail. Doesn't mean, there's no shame in it, but you gotta make more bad decisions to fail in an internet era than in a retail fixed world era. The cloud expanded the playing field. And then y…”

“Sometimes the, you can't get the information even if you ask the right people. And so Manscaped worked so well is because they offered a product that people wanted and no one was admitting to it. And that's just when you get outlier wins.”

“You have to be, you can't just be some fat bond trader. You have to understand community, you have to understand technology, you have to understand How to behave. You have to have social skills. You don't have to be on a high rise. You don't have to be in New …”

“And so it's destroying creativity and it's also you're going to start to see some massive fallout i can't predict when but you're starting to see cracks companies misbehaving again because you know it's okay for wells Wells Fargo as part of the S&P 500 to misb…”

“Where startups versus the stock market differ is that in the stock market, I don't think you need 500 stocks, the S&P 500. I think an average person can own 12 companies. I call them eight to 80 brands that you use from eight years old to 80 years old have a d…”

“In the private markets, I totally believe that the more the merrier, and not so much spray and pray, but having a hundred startups is not bad.”

“In 99, 2000, I'm sure Fred Wilson and Brad Feld and a lot of the VCs wish they understood the stock markets because they would have sold, because they could have sold. Instead, they wrote everything to zero in 2001.”

“And so I really had committed to Zynga, passed a month later based on the price that was set. A big mistake.”

“So there's just so many subtleties to the whole, I would call it more of an art than a skill. I think, everybody's trying to teach people how to raise money, and I would say, hey, listen, not everybody can be an artist.”

“Raleigh Road's like training wheels for a digital world, right? So Raleigh was too far ahead. And now the time is theirs, but it took NFTs for Rally Road to be cool, because for people that can't Go full digital, but let's just say that's 99.5% of the populati…”

“First rule of thumb, follow smart people, right? Because just like in sports, in the Tour de France, if you can keep up with the smart people, then you can just draft behind them.”

“People need to lose money to really understand how the markets work, and you can lose that money in a private deal or in the public markets, but until you're cut and bleed and see how co-investors behave with you and how the entrepreneur feels, I don't think y…”

“I never have fear of missing out. The stock market's taught me never to chase.”

“The difference between, between paying two pre and 20 pre can be massive, especially if you're not going to have the capital to follow on.”

“We've been building StockTwits for 12 years, it's a big company, it's profit, big company in terms of revenue and profits, and you know, we haven't raised a ton of money”

“Free trading had been around for a while. Zappo. Zekko. And I passed on it because it was, but it was desktop, and it just didn't, it was before the iPhone in many ways”

“We were actually, Tom and I, my partner, were one of the first checks into AngelList in 2010.”

“Luckily for me, I probably lost on my first four back in 99 when everybody lost money in the bubble. But when I really started investing after I sold Wallstrip I caught a great crop of entrepreneurs in 2006, 2007, 2008, and I would say 50% of the companies wor…”

“Back in 2006, one of my first angel investments was a company called LifeLock, which is now a couple billion dollar company, and they're out of Phoenix.”