20VC: Chris Sacca, Chamath Palihapitiya, Gary Vee, Brad Gerstner and more on Their Relationship To Money, How It Has Changed with Time and Wealth, How They Bring Up Their Children To Engender the Same Values of Ambition and Hard Work?

**Chris Sacca** (0:00)
Those people look like money fucked them up. Let's go sit with them for a drink and ask them a lot of questions and get to the root of it.

**Harry Stebbings** (0:06)
So how does money fundamentally change a person? And what is the right way to think about one's relationship to money? Now, I've done over 3,000 interviews of 20VC with some of the biggest and best investors and founders. And this is one of the most fascinating questions. And so today we have Chris Sacca, we have Brad Gerstner, Gary Vaynerchuk, Chamath Palihapitiya and more on their relationship to money, how it's changed over time and the wisdom and lessons they have from that experience. This is an incredible compilation. I really would love to hear your thoughts. You can let me know on Twitter at Harry Stebbings and I hope you enjoy it. But before we move into the episode today, holiday gifting for your friends and family can be hard and for your business, it can be even harder. And Open helps companies of all sizes deliver better gifts and they make it super easy. Their platform is filled with best in class brands. There are no bad gifts ever. They source locally and operate globally. You don't even need an address. Simply send an email or DM with a unique gift link ready to put the ease and joy back into your company's gifting. Head over to andopen.co forward slash 20VC. That's andopen.co forward slash 20VC to get started today. And speaking of amazing tools, which really take complex processes and make them super easy, AngelList has been a key partner for me in managing my investments. I love using the AngelList platform because it abstracts away all the complexity and operational burden of fund management. Whether you're running SPVs, a traditional venture fund like me, or even a rolling fund, AngelList has you covered. The team is also just exceptional. They're great, great partners. I'm also super excited about their new product though, AngelList Stack, which is purpose-built for founders. With AngelList Stack, you can create a fundraising-ready startup in just a few clicks. AngelList handles all your company's incorporation, banking, cap table and fundraising process all in a single place. This allows founders to really focus on building. If you're a founder, you can launch your company at stack.angellist.com forward slash 20VC. Whether you're a founder or a funder, you're in great hands with AngelList. And finally, from websites and online stores to marketing tools and analytics, Squarespace is the all-in-one platform to build a beautiful online presence and run your business. There are three things for me that really stood out about Squarespace. First, mobile optimized websites. All websites are optimized for mobile. Content automatically adjusts beautifully, so your site looks great on any device. Second, email campaigns. Squarespace makes it super easy to grow and engage your audience with Squarespace email campaigns, so you don't need any other tools or providers. Such a relief on that one. And finally, SEO tools. You've got to be found on search engines. And Squarespace takes the guesswork out of SEO, so you'll get found by more people more often. And if that wasn't good enough, head over to squarespace.com forward slash 20VC. Not only do you get a free trial, but when you're ready to launch, use the offer code 20VC to save 10% off your first purchase of a website or a domain. But that is enough from me, so now I'm delighted to start with the one and only Chris Sacca at Lower Carbon Capital.

**Cyan Banister** (3:10)
You have now arrived at your destination.

**Harry Stebbings** (3:13)
How do you think about your relationship to Money Stay, Chris?

**Chris Sacca** (3:15)
Yeah, I think I'm lucky in that I don't feel competitive with other investors or other rich people. I have a lot of friends who are tortured by it. They have countless dollars at hand, but feel like the goal line is always moving and they need to keep up with somebody else. So I certainly look at it as what can I do with the money we have? And luckily, we have all the stuff we want. You get to this point where, like in the beginning, I made a bunch of money and I bought houses for family and multiple houses for ourselves. And then my wife and I turn around and we're like, fuck, we're property managers. Our inbox is like, hey, this broke and this is happening. And what do we do? I was like, so we're just prisoners to our stuff right now. Again, it was lucky that I kind of got into that early and realized like, oh my God. And then you start to realize we're fortunate enough to go on vacations, but we don't need to own that chateau. It's amazing. There's some incredible places in Europe where we love to spend time that you can rent. And then when you're done, you walk away from them. You can live luxuriously and then not have to own it. And luckily, we're also not into big boats, thankfully. So that's a great way to light money on fire. But for us, you know, I'm lucky that Crystal and I have been best friends since we met freshman year of college. We didn't date for 14 more years after that. But I'm lucky that we've grown up with this money together. And the thing that we did that I think more people should do is we sat down when it became clear we were going to make some money. And by the way, I didn't come up with this idea. I saw Evan Williams do it. When Evan Williams saw that he was going to make some money, he went out and started interviewing rich people and asking them for tips.