AlleyCorp

“The real use of AI in the short term is going to be much more mundane. It's optimizing customer support, you know, making your coding more efficient, things like that. We're a long ways before, you know, true AI companies are coming”

“Where is the world going to be in 10 years? That's the North Star for what we're doing. If something's gonna happen next year, it's too late. I need to bet on a ten-year trend.”

“You know, you can't truly be CEO of multiple companies, but you can be chairman of multiple companies, but you got to start with one. And if you try and do two or three at the same time on your own, it's not going to work.”

“All in on private companies. So probably 90% of my net worth is just in my own farm in, in investing in various companies and things. I have a li, I have some in, in some VC and private equity firms, you know, as an LP. You know, and I do have some real estate…”

“So we started each company with a million dollars. So 500,000 from each one of us. And that was for Gilt, Business Insider and Mongo. And then we, I did after that Dwight semi-retired. And so I did that with Nomad. I did that with Zola. And now, by now I put a…”

“Because we started off with a million and a half dollars, but we raised forty million dollars about a year to a year and a half later in two tranches at eighty million free.”

“Another company we invested in is, so driverless cars is, as you know, not legal in most countries, most states, but having a remote driver is.”

“You got to think of yourself as you are the coach. You are not the player. And if you're a coach and if you manage to persuade, you know, LeBron James and Kevin Garnett and a bunch of people on your team, your team's going to do well. That's actually the job.”

“No, the people are on my marketing team know that the goal is that we are very successful. And that when I walk into a restaurant, no one knows who I am.”

“We're an investor in a company that gives robotic massages. There's 17,000 open positions for massage therapists in this country. And so, you know, there's hotels that just can't offer massages because they don't have the people.”

“And I have companies right now that we've cut 30% of the people in the last year because given this market and what they were doing, we had too many people.”

“So I chair 12 companies. So about half my time is spent focusing on those 12, which are 12 of our most valuable companies to really guide them and make sure that they do as well as possible.”

“I have 70 engineers who work for me. I have my own in-house outsourced engineering company, which helps us build product now very quickly, which we've had the last three years. I own a big chunk of a search firm, a 10 person executive search firm that we set u…”

“Now there's still risk, but that company is, you know, we currently have a fifty million dollar position based on our five million that we've invested so far, and we think it has a lot of potential.”

“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've invested probably two hundred fifty million dollars into the various companies over the years.”

“Six months ago, you know, the pricing on AI was insane. You know, three people walk in and say we're worth a hundred million dollars because we're going to put together an AI company. Just didn't make sense. So we didn't make any direct investments there.”

“They just raised twenty million dollars from General Catalyst and Kevin Ryan from Alicorp.”