The Exchanges

Q prove that they can run those businesses. And so they, their concerns were similar where they're like, yeah, you know, they, they didn't have both of the founders hadn't previously opened a business. And I said, You know, how do you, you know, justify buying a business when you don't really have experience running a business? He's like, but my, my PE firm is a business. I'm running a business.

A It is a business. So our venture capital firm is a business. You know, we had to go out and raise capital. We then had to like deploy it into entrepreneurs who we really believed in. It's just a different type of business. If you are fortunate enough to be a venture capitalist, it's the best business model ever. You get paid a fee to manage the money and you get a piece of the upside, typically, 20% after you return your capital. Our buying businesses, that's all our capital. It is, we're responsible for the teams. We feel like we're part of the team. So it's just a different type of business. But if you look at people who've built great venture businesses or PE businesses, they're entrepreneurs. So you can't say that whether it's Devin Parekh at Insight or, you know, Josh Kushner at Thrive, they've Built businesses as an entrepreneur, but they're very unique in their space.

AI assessment note: “It is a business. So our venture capital firm is a business.”

Q What's been the thing that you've enjoyed the most working on? Which brand?

A Man, oh man. I mean, we have a hundred deals on the venture side, both personally and through the fund. And I think the most enjoyable part of that is working with entrepreneurs and seeing them succeed. So there's nothing better than seeing an entrepreneur grind it out, suffer, get to the other side and reach their dreams, whether it's being a public company, which we've, you know, done or, you know, big exit, like the five billion dollar exit. Um, that's scopely one of our seed investments had to Savvy Games. You know, Liquid Death is a really great example of here's a creative director, Mike Cesario, who comes up with an idea to market a wellness product, water, in a very novel, innovative way across social media. Did we think it was going to be a billion dollar plus company? We thought it could be a big company, but seeing him succeed, Has given us a lot of just personal enjoyment since we were there from pre-launch in the beginning. And then on the owning business side, it's really seeing people reach their full potential. So it's all about people. It's all about, you know, where are you today? Where do you want to be? And we've just worked with great people like Dina Uffberg, who's the COO of that business, who came from tech and wanted to run her own business. And, you know, she's just done a phenomenal job. So it's, you know, it's just seeing people succeed and we love t…

AI assessment note: “Liquid Death is a really great example of here's a creative director”

Q lost my sense of purpose in a way, like I don't need to work anymore. Should I? Uh, what should I do? How should I feel? Like, what should I do about this? And, you know, I, I know that you had really large exits. So I was wondering if after one of those exits, you kind of felt lost. You felt disconnected or you felt numb or, you know,

A So yes, I mean, all the above, and I've spent a lot of time with founders and their organizations like chapter X that actually are focused on like founders post exit. I was at one of their events in LA earlier this year, and a very big founder sold the business for, you know, over a billion dollars and made hundreds of millions. He said flat out, I'd give the money back in a second just to get my company back and find my purpose again. I said, Would you really? Let's be serious about this. And what happens is, you know, and you hear about this, but when you experience it, it really hits hard. The money doesn't change you for the most part. You realize that life is not about the money. It's about the passion, the purpose, the waking up in the morning and having a place to go. And we all feel lost. I did. So I haven't talked about this, but after I left Salesforce, we sold to Salesforce close to a billion dollars. I spent close to four years there, loved it, still love the company. And then I'm, I was burned out and I went to Mark Benioff. I said, You know, I'm gonna take some time off, and I got a painting studio in New York City. Cass, my wife, actually got it, and I was just miserable because I was bad at painting. I wasn't doing what I was put on this earth to do. I didn't have any sort of purpose, even though I was working on a series of paintings based on my entrepreneurial…

AI assessment note: “So yes, I mean, all the above”

Q Are you taking the profit from the VC firm to fund the PE firm?

A I mean, it's all in one bucket. So Cass and I have worked together for 30 years. We have, you know, done eight businesses. And so, you know, I wouldn't say we're taking one to fund the other. I would say that our success as an entrepreneur, where we made, you know, boatloads of cash, that has powered our ability to then go find deals and buy companies. Whereas the venture capital business, even though, you know, Big portion of the money is our money. We also have outside investors. So, you know, success breeds success, but what we like about is on one side, it's all about innovation and the future and deep tech and software and AI and, you know, and liquid death and some other brands that we love. And then on the other side, we're talking about boring businesses. So an executive search business that's been around for 25 years with 2200 Your client and 6500 successful placements, you know, that's a business that generates cash that if you just serve the customer well, do what you say, and in that case, hire A-list talent, you'll continue to grow it, which is why we love it. So it's this barbell approach that as investors and entrepreneurs, we love.

AI assessment note: “I wouldn't say we're taking one to fund the other.”

Q What are you most excited about for the future?

A The number one thing I'm excited about is boring businesses that use AI to streamline processes, to find new customers, to communicate in a better way, and we just think that although all of this discussion about AI has been focused on open AI and these multi-billion dollar platforms, it's the plumbers, it's the painters, it's executive search firms, it's the accountants, it's the small law firms that are going to use the This technology, and if you are owning a business today, even if you have three employees, how do you use this technology to automate a lot of the stuff that frankly you hate doing? Like, stuff that you don't love doing, whether it's cold outreach, whether it's kind of inventory, right? So I was just talking to a small business owner who, you know, has a retail store in New York City, and they're automating all of their rebuying of inventory. So it used to be, you'd spend hours, like, walking through the store, and this company has, like, thousands of SKUs. So I'm not going to talk about what it is, but it, you know, it's in kind of, like, The crafting space and has a lot of stuff, and so now he gets four hours a week back because he's able to say, oh, we're low on this. We should order this, and then using the technology to understand, like, what's selling fast? What should they ramp up? What areas of the store should they re, you know, repurpose for other th…

AI assessment note: “The number one thing I'm excited about is boring businesses that use AI”