BTC037: TECH ENTREPRENEUR TO BITCOIN INVESTOR

W/ JAY GOULD

04 August 2021

On today’s show, Preston Pysh sits down with tech entrepreneur and Bitcoin Investor, Jay Gould. Jay talks about the lessons learned from founding numerous companies and his thoughts on having Bitcoin as part of his investment portfolio.

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IN THIS EPISODE, YOU’LL LEARN:

  • How Jay Gould got his start as an entrepreneur.
  • What Jay thinks is a replicable part of entrepreneurship.
  • What tech ideas has Jay excited now.
  • The legal battles Jay faced after starting one of the most popular websites in the world
  • Advanced negotiations against people like billionaire Mark Cuban.
  • Jay’s Bitcoin story.
  • Jay’s concerns with the speed of Bitcoin’s adoption.
  • Jay’s thoughts on Elon Musk entering Bitcoin.
  • A discussion of the macroeconomy impacting Bitcoin’s speed of adoption.

TRANSCRIPT

Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.

Preston Pysh (00:00:03):
Hey, everyone. Welcome to this Wednesday’s release of the show, where we’re talking about Bitcoin. Today’s guest is a friend, entrepreneur and fellow Bitcoiner, Jay Gould. Jay has been a tech entrepreneur for more than two decades. On today’s show, we get into a detailed conversation about many of those experiences that shaped his thinking on founding, building, and selling businesses. The last tech business that he sold, he sold for $33 million, and today he’s an active venture capitalist and a Bitcoiner. For the first half of the interview, we cover his lessons learned, trials and tribulations with raising money from billionaires, like Reid Hoffman and much, much more. And then in the second half, we cover his thoughts on Bitcoin and how he thinks about it as an investment in his overall portfolio.

Preston Pysh (00:00:46):
I thoroughly enjoyed this conversation with Jay. He’s just so open and candid with what he knows and what he’s learned through the years. And so, it’s just an incredible lesson for people to hear from this firsthand experience of all these different businesses that he’s created through the years. So with that, let’s go ahead and dive in with Jay Gould.

Intro (00:01:07):
You are listening to Bitcoin Fundamentals by The Investor’s Podcast Network. Now, for your host, Preston Pysh.

Preston Pysh (00:01:26):
All right. So like I said in the introduction, I’m here with Jay. Jay, welcome to the show. I’m pumped to talk to you. I love talking to entrepreneurs, so I’m excited to do this, man.

Jay Gould (00:01:36):
I’m excited to be on. Thanks for bringing me on.

Preston Pysh (00:01:38):
I guess let’s start here. My understanding is that you started your very first website business whenever you were in college. I guess my question for you is, are you a self-taught programmer? Were you outsourcing the code base to somebody else? Just give us some insights on how you got your start with your very first company.

Jay Gould (00:01:57):
Believe it or not, it wasn’t programming. People always think I’m a programmer. I wasn’t a programmer. I had these ideas. I use the internet just like everybody else. I’m a power user. You see me on Clubhouse and stuff and all these other things. I saw my behavior and I’ve always felt I’m very average. I don’t think I’m any different than anybody else. I think most people are just very similar to each other. By the way, when you go down a path in school like for pre-law, you take a lot of psychology classes and sociology and that kind of stuff too, right? And so, you understand the mindset of people by taking these types of classes a little bit. So when I started to use the internet, I thought I was using AOL and the chat rooms, like the early days in the ’90s. I was like, “You know, I think this is going to be really big.” Because of the way I felt using it, I was compelled and sucked in, and drawn into this. It was addictive to me. It was like playing a video game. I was a big gamer as a kid. I was like, “You know, I think this is a thing.” This was in the late ’90s in college, right? I graduated in ’01. So in ’97, ’98, ’99, I’m having some friends that I met in CS classes and that were programmers and I really didn’t have the bug for that. I wasn’t really into it, but I was into wanting to build. I really wanted to build something that people wanted to use, and I saw the opportunity to build something where it could be massively scaled before I even thought of the term scale, just lots of people using it.

Jay Gould (00:03:13):
I just knew how I felt about using these products and I thought I could draw people in if we added certain types of features [inaudible 00:03:18]. So the first thing I built early days was not social, believe it or not. I was into e-commerce kind of websites, selling things and all that kind of stuff, ICM, SEO. Learned that. That was a good foundational base from the marketing side of it, understood the users. When I started to get into building social media sites, that was the first thing I really did after the e-commerce stuff to make a little money. The first thing I did was I built a dating site. I built that site and had a real early success there, sold that, or like 2003, I guess.

Preston Pysh (00:03:49):
Were you hiring the programmers, or what were you doing?

Jay Gould (00:03:53):
You could do that back then. Today I say to people, “My path, the way I went, I don’t think you can replicate that path.” Today everybody who’s a good programmer and the way the world is with the 0% interest rates will probably go in and out of Bitcoin as you said. With the 0% interest rates today, money is almost free. So if you’re a good, talented developer, you don’t need to work for me. Just go get money from somebody and build it yourself and have your own company. That was not the case in the late ’90s, right? People didn’t understand how to raise money. It wasn’t widely available. There wasn’t YouTube yet. There weren’t blogs, people like Naval Ravikant teaching people how to raise money and how a term sheet works, and all this kind of stuff. So we’ve democratized the information for people to freely understand how to do this, which is great because we’re getting better products and lots of companies are being created. Amazing things come out of that. But when I did it, it was not as competitive as it is today.

Jay Gould (00:04:41):
So when I started to do it, I could hire people to work for me and not even pay them a lot of money, right? American people find people in India and Pakistan, all parts of the world through like Elance and stuff like that, and that’s what I did. In the beginning, it was kids in college that I knew. And then over time, I found people through the internet and became friends with these guys and still friends over 20 years with some of these people and we built some of the earlier stuff together.

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