Gregory Shepard

Gregory Shepard


Listen on

Apple Podcast

Co-Founder BOSS Capital Partners | BOSS Startup Science

Advice for founders and investors – Gregory Shepard

“Your vision is a direction. You build to your customer or aquirer’s needs.”


Greg is a 20 year startup veteran and serial entrepreneur with 14 liquidity events under his belt, two of which were sold as part of a $925M transaction that won 4 PE awards for transactions between $250M-$1B. A ForbesBooks author and has written over 100 articles published in 25 national and international publications. A TEDX speaker and keynote speaker for universities, associations and conferences worldwide. He is the Host of Meet The BOSS Forbes Radio show and has been featured as a guest on over 25 popular podcasts as well as numerous network TV and radio shows. Greg Co-Founded BOSS Capital Partners, a global syndicate for investing in tech startups worldwide. Greg Co-Founded BOSSStartupScience the learning center is based on Greg’s Business Operating Support System (BOSS) an open source methodology developed to empower entrepreneurs while increasing startup success rate.



Gregory Shepard

The full #OPNAskAnAngel talk

Jeffery: Welcome to the supporters fund asking investor I’m your host Jeffrey Potvin. Let’s please welcome Gregory Sheppard at boss Capital partners as our investor for today. Welcome. Gregory It’s a real pleasure having you join us.

Gregory: Thank you for having me. I appreciate it.

Jeffery: Well, Gregory, I know we chatted multiple times over the years, but I’m really excited about this podcast. Probably the most nervous. I’ve probably been on a podcast because it’s almost like I’m a fanboy. Of all the things that you’ve done in your career, I’ve watched a lot of podcasts and videos. You’ve done an exceptional job on how you actually work in the startup space, and not a lot of people do that, and a lot of people are kind of the surface level we like to help, but you’ve taken this to a whole different level, and so I’m excited to kind of dive into that and learn all the research and the things that you’ve guys done as a business, but also where you’ve come from. And the way we like to start our show off is we want to learn a bit more about you, so maybe you can share all the way back to your first company, all the way through to what you’re doing today. And then one thing about you that nobody would know.

Gregory: Sure. First of all, thank you for the kind words as I’m humbled and I really, really do appreciate it. And I’m a fan of you as well. So it’s it’s samesies, I guess. So. I can tell you, starting back when I was young, I grew up pretty poor. You know, we lived in tents for a couple of years while we built our house. And we we’re family have been foster and adopted siblings and different nationalities. There’s two of us that are biological. My mom was a nun, actually. My dad was a priest. And then they left the church to India to take care of children. And then I have autism, dyslexia, synesthesia and savant syndrome. So I had a lot of problems growing up, you know, just everybody making fun of me, getting beat up on racial faces. But I did start selling Rubik’s Cubes and solving them. And I sold rattlesnakes. I used to catch rattlesnakes and so on as exotic pets and antivenom and I mean a lot of different things as a kid, including breakdancing, which nobody knows about. I used to break down for money in San Francisco, but my first business was actually a nobody knows this because I never talk about it. But you wanted something. So I started a bungee jumping company called Pure Adrenaline, Bungee jumping. And we did like the Mountain Dew commercial, you know, where they go in and come out with a Mountain Dew. We jumped up a Chevrolet off of a bridge one time. Lots of celebrities, things like that. And it losing all my money. It was terrible. First business. Then I went into banking and started a non depository bank. I think I was like 20, 20 years old, maybe 21 years old, called American Federal Lending. We sold that. Then I went into it, applied Environmental Biotechnology, sold that to a public company in Canada. We spoke about that a little bit before then when the Internet came out, then it was like paradise, right? Because you could take vapor and just create things. And it was like for me, it was like the most I couldn’t believe it. So I started coding it very early and then I created a whole bunch of websites and I started to learn about the need for websites. There was just like Gold Rush. Everybody was trying to get websites. So I worked with with an investor and created a Automattic website builder, which then morphed into an advertising agency which then morphed into a advertising compliance company, an affiliate, marketing passports and visas and travel insurance. We started the first travel insurance online, the first agency in the ability marketing space. The first ad compliance based product line that was attached to that, that were. And it just went from there, you know. So I’ve done 12 startups and I’m on 13 right now with, well, 14 actually, if you take the fund and then you two are the, the, you know, most capital partners in startup science and you, there’s, there’s two more there and then I’ve done a bunch of investments, I think somewhere around 14 different investments. And all in all, I only lost twice. One was the bungee jumping company and one was a real estate company during COVID, which I did sell, but we didn’t make money, so I counted as lost because it was a fire sale code. It just destroyed real estate for a little while. There. And during that process, I sold two companies to eBay, one for private equity awards for transactions between 250 and a billion ended up being the chief strategy officer for eBay Enterprise for a while. And then we bought all these companies from eBay and then we I became chief technology officer. And then that company sold a couple times after we sold all the pieces and stuff like that. And then I started going into politics and I was trying to get women and people of color into Congress in the United States. And I found that that was a not a probable outcome as long as people can lie. So instead, what I decided to do was go direct to the source and help with wealth inequality, inclusion and environmental issues and sustainable issues by helping founders, because that’s what I had done. So I started a research project and I put 500 grand into a fund, and then I hired a bunch of people. And then we did this starting in 2016, studying why women and how founders failed. When I learned about that, I found the majority of the founders are failing for the same reasons over and over again. And I was like, okay, well, maybe we can’t solve all the reasons why they’re failing, but maybe we can just work on the ones that are repetitive, you know, the things that are reoccurring, problems that happen over and over again. So then I started a school to teach people about why founders were failing and how not to and all of the different things that they needed know about it. And that became startup science. I which is a SaaS platform that we offer to universities, accelerators, incubators, we call them startup assistance programs, and that’s what I do now. The process has been a, you know, over 30 years of of work and a lot of consequences and a lot of I mean, there’s a lot of things that a lot of trade offs. And you know this because you’re you’re like me, right? I mean, you come up and you just keep grinding, you know? So I think I’m sorry for being so wordy, but that’s that’s pretty much a good summary to start out with.

Jeffery: No, this is great and a great start. It all add in that you’ve also got a podcast YouTube channel, so you guys do a lot of different things. But the underlying piece to this is education. Yeah, it’s taking what you’ve known and turning it into something that can bring value for other people. And I know you talk a lot about it even in your shorts or one minute videos that you have on YouTube. Those are pretty good because they’re just one minute of insightful detail that, hey, maybe you’re not thinking about this today, but I’m going to throw this out there anyways. And I think that a lot of these pieces all come back to that educational side. And when you go back to when you started your first company and even the one that you said failed, there was so much learning you gained just from that one business. And what I think the underlying kind of terminology to everything that you’ve got is that you have no limits. And if you create limits, you prevent yourself from moving forward. Is that fair statement?

Gregory: Yeah. I mean, I think that I mean, my life has been full of failure, but failure is just another word of progress. So, you know, if if you find yourself failing, then you’re progressing. If you find yourself not failing, then you’re standing still, right? If you think about struggle as a positive meaning, if you think about just organically the way the universe works right? Plants grow through concrete. They do really healthy when they’re struggling, People will always tell you, yeah, your plant needs to struggle. Your own body doesn’t go through autophagy, which is where the the the bad cells are digested in and reformed into good cells by the good cells. Unless your body’s in struggle as we’re all this cold shower and fasting and stuff comes from. Right. So struggle is a necessary progress, a process to progress. Right. Like it’s important to I think that I look for it, you know, every year I try to find something that I think is impossible. And then I go do it, you know, to prove that even the what you think is impossible can still be done. I mean, I’ve done every kind of happy damn. You know, I ran a marathon. I swam a marathon last year in the ocean. I didn’t even know how to swim before that. So, you know, and I have asthma. So, like, you have to choose these things. Now, being a founder is the ultimate right. Our founders are the friggin Navy SEALs of business. If you can make it as a founder, you are running circles around anybody els