The Exchanges

Q How do you kind of sort the wood from the trees, then, in this very crowded market of noise and talk?

A Um, I've been in long enough that I, I, I'm fortunate that I have friends. Uh, we're all, you know, we all share deals with each other and, uh, you know, and you sort of know when you meet people, you know, you, you, cause I, cause I'm a, you know, I've been doing this and not the VC part, but the entrepreneurship part long enough. I can just talk some, ask someone questions about their company and how they're building and know exactly what they're doing. And if it's, this is a real one or not, you know, like I'm at a, um, what questions would you ask? Well, you know, usually, like, um, I want to understand their product. I want to understand their team. Why do they have this person on the team? You know, what's their burn rate? Like, why is their burn rate like this? You know, how are they going to distribute? I think the basics question is the basics on building a business online, right? And, and, uh, because a lot of people are just very wide-eyed, starry-eyed, and they don't understand, um, the actual, you know, oh, yeah, we'll just build it with our ads on it, or we'll just, you know, we'll just charge a subscription fee. It's, it's, you know, it's, all that simple stuff's been done. You know, it's how, it's how the web, you know, any industry involved is simple stuff. People make a ton of money in the beginning, then, then it becomes complicated as everyone's doing it.

AI assessment note: “ask someone questions about their company and how they're building and know exactly”

Q Who are the up-and-coming ones, then, that you've noticed?

A Uh, like, vast VC in New York is my favorite here. Um, and then outside of, uh, here, like, just in, uh, in San Francisco, in the Bay Area, Silicon Valley, like, just the Angels. Yeah, well, no, there's ones like, um, Kent Goldman. Uh, he left, you know, I'm, uh, he was actually a board observer at my last company. He was such a value add. He's, he went off and started his own, his own fund. There's always like one partner fund starting, you know, where they're like really one guy, they got to make a name for themselves. They're real value add, you know, and then just like the Angela syndicates, you know, like I've heard like Tim Ferriss, he really helps his companies. The syndicates are, you know, like that's the few, that's, uh, Tim Ferriss, Rick Marini, Jason Calacanis, Jason Calacanis, Lee Jacobs, you know, all these guys who were just, who were all entrepreneurs, right? All built stuff, and now, like, through AngelList are basically running, you know, one-off funds. I would take their money over a lot of VCs any day, in a heartbeat, because I've actually been, okay, so Rick Marini, right? He was a CEO of Tickle in the dot-com boom. He sold it for, he built it, it was a really legitimate, like, hard work, built it, sold it for a hundred million. Start another company, Branch Out, that did, that exited recently, and he, he and I were investors in Luxe Valet, and I went to a …

AI assessment note: “vast VC in New York is my favorite here... there's ones like Kent Goldman”

Q How do you kind of sort the wood from the trees, then, in this very crowded market of noise and talk?

A Um, I've been in long enough that I, I, I'm fortunate that I have friends. Uh, we're all, you know, we all share deals with each other and, uh, you know, and you sort of know when you meet people, you know, you, you, cause I, cause I'm a, you know, I've been doing this and not the VC part, but the entrepreneurship part long enough. I can just talk some, ask someone questions about their company and how they're building and know exactly what they're doing. And if it's, this is a real one or not, you know, like I'm at a, um, what questions would you ask? Well, you know, usually, like, um, I want to understand their product. I want to understand their team. Why do they have this person on the team? You know, what's their burn rate? Like, why is their burn rate like this? You know, how are they going to distribute? I think the basics question is the basics on building a business online, right? And, and, uh, because a lot of people are just very wide-eyed, starry-eyed, and they don't understand, um, the actual, you know, oh, yeah, we'll just build it with our ads on it, or we'll just, you know, we'll just charge a subscription fee. It's, it's, you know, it's, all that simple stuff's been done. You know, it's how, it's how the web, you know, any industry involved is simple stuff. People make a ton of money in the beginning, then, then it becomes complicated as everyone's doing it.

AI assessment note: “I can just talk some, ask someone questions about their company and how they're building”

Q And you've said before that now's the best time to be an entrepreneur. Why do you think that is?

A Uh, because you don't have, especially online, you know, even the intersection of online and offline, uh, like, if you think about it, before the internet, you know, you only had specific businesses you could start and to raise capital and so forth, um, you know, and you couldn't, like, start a business and then two years exit for a billion dollars. You know, it just wasn't, you couldn't, unless you're an insider in the oil industry or something like that, but, you know, then after the internet, the dot com boom, you know, you still need to raise a lot of money, And to build, you know, currently, like what we built back in the late nineties with giant teams of 20, 30 engineers and product managers and all, and we have our own servers and our own hardware. You can do that now with one or two guys and Amazon services and all this open source stuff. So. And you can have a, and then distribution, which is the main thing, right? In the end, you can create the best product in the world, but if distribution channels are open to you, you're screwed. So as a writer, like Amazon, you need to self-publish at Amazon. That's where people are, um, looking for books, right? That shit, that's what happened with me, and my book outsells most New York Times bestsellers, and it's only on Amazon, right? That's the distribution. But as far as, uh, if you can build an app, And you've been the app st…

AI assessment note: “Distribution is taken care of. Now you just have to create”

Q And you've said before that now's the best time to be an entrepreneur. Why do you think that is?

A Uh, because you don't have, especially online, you know, even the intersection of online and offline, uh, like, if you think about it, before the internet, you know, you only had specific businesses you could start and to raise capital and so forth, um, you know, and you couldn't, like, start a business and then two years exit for a billion dollars. You know, it just wasn't, you couldn't, unless you're an insider in the oil industry or something like that, but, you know, then after the internet, the dot com boom, you know, you still need to raise a lot of money, And to build, you know, currently, like what we built back in the late nineties with giant teams of 20, 30 engineers and product managers and all, and we have our own servers and our own hardware. You can do that now with one or two guys and Amazon services and all this open source stuff. So. And you can have a, and then distribution, which is the main thing, right? In the end, you can create the best product in the world, but if distribution channels are open to you, you're screwed. So as a writer, like Amazon, you need to self-publish at Amazon. That's where people are, um, looking for books, right? That shit, that's what happened with me, and my book outsells most New York Times bestsellers, and it's only on Amazon, right? That's the distribution. But as far as, uh, if you can build an app, And you've been the app st…

AI assessment note: “You can do that now with one or two guys and Amazon services”

Q And you said you've been invested in by amazing VCs and Angels. What do you think makes an amazing VC or Angel? What do you try and emulate?

A You know, honestly, it's, It's genuine help, whatever the entrepreneur needs, you know, whether it's, you call me in the middle of the night because you're having a rough day to, like, you know, I have to walk you off cliffs, because, you know, because I've been there. I've, I've seen it all. I've been, I've done it all, you know, but down to the part where they actually help, like real help, and not bullshit advice, which is my pet peeve, you know. A lot of people, VCs or investors call themselves value-add, and it's just garbage advice like that. You know, I've got advice as a, as a CEO where I've thought, You gotta be shitting me. Like, you call me to tell me this? Like, you don't think my engineers, like, have the best engineers in the valley working for me? You don't think they thought of this? Like, you know, that kind of stuff, or, um, and then the worst, the worst are the ones who actually, like, get in the way, and then start, like, um, uh, basically forcing you to reconsider your decisions, but not in a healthy manner, but, like, really, like, yelling and screaming and getting other investors involved, you know, like, In the end, I really believe it. It's not the investor who makes a company. It's always the entrepreneur.

AI assessment note: “It's genuine help, whatever the entrepreneur needs”

Q And you said you've been invested in by amazing VCs and Angels. What do you think makes an amazing VC or Angel? What do you try and emulate?

A You know, honestly, it's, It's genuine help, whatever the entrepreneur needs, you know, whether it's, you call me in the middle of the night because you're having a rough day to, like, you know, I have to walk you off cliffs, because, you know, because I've been there. I've, I've seen it all. I've been, I've done it all, you know, but down to the part where they actually help, like real help, and not bullshit advice, which is my pet peeve, you know. A lot of people, VCs or investors call themselves value-add, and it's just garbage advice like that. You know, I've got advice as a, as a CEO where I've thought, You gotta be shitting me. Like, you call me to tell me this? Like, you don't think my engineers, like, have the best engineers in the valley working for me? You don't think they thought of this? Like, you know, that kind of stuff, or, um, and then the worst, the worst are the ones who actually, like, get in the way, and then start, like, um, uh, basically forcing you to reconsider your decisions, but not in a healthy manner, but, like, really, like, yelling and screaming and getting other investors involved, you know, like, In the end, I really believe it. It's not the investor who makes a company. It's always the entrepreneur.

AI assessment note: “honestly, it's, It's genuine help, whatever the entrepreneur needs”

Q And do you find your investment strategies much more strenuous now you're investing with someone else's money instead of your own?

A Of course. I actually have, I don't invest my own money. I, um, You know, like, I, you know, the story, like, I lost all my money in my last company. I was in, you know, blew up, and I was in, like, serious credit card debt and everything, and, you know, I've been able to change my life around, um, and, uh, it's amazing where I am now than where I was just, like, you know, three, four years ago, uh, but if it's someone else's money, you know, there's a whole level of responsibility. It's just like taking money when you're building a company. I feel the same way, You know, it's not your money. You know, you don't go around throwing crazy parties and wasting money. It's not your money. You took money from someone, so now your job is to actually allocate it to the best possible use for building the company.

AI assessment note: “if it's someone else's money, you know, there's a whole level of responsibility.”

Q So, can you kick us off today with a little bit of background about you and how you made your start as an entrepreneur? And then made your transition to investing.

A Yeah, I'm not your traditional VC. In fact, uh, you know, if I was to say as a VC, I've only been doing it for a couple of years. Um, as an entrepreneur, you know, I always like to say I wasn't like, you know, your standard national entrepreneur who's always, you know, selling things. I, what I, what I did was I moved out to Silicon Valley in the late nineties when the dot-com boom was happening. And I, um, ended up joining a startup called Healtheon and helped build that. Healtheon became WebMD. And, uh, you know, like, I started as a product manager there. I got known as the can-do kid, because in those days, you know, if you could just take anything, I'd run with it, and that was fun, because we were building things that had never been built before, right?

AI assessment note: “I moved out to Silicon Valley in the late nineties when the dot-com boom”

Q So, can you kick us off today with a little bit of background about you and how you made your start as an entrepreneur? And then made your transition to investing.

A Yeah, I'm not your traditional VC. In fact, uh, you know, if I was to say as a VC, I've only been doing it for a couple of years. Um, as an entrepreneur, you know, I always like to say I wasn't like, you know, your standard national entrepreneur who's always, you know, selling things. I, what I, what I did was I moved out to Silicon Valley in the late nineties when the dot-com boom was happening. And I, um, ended up joining a startup called Healtheon and helped build that. Healtheon became WebMD. And, uh, you know, like, I started as a product manager there. I got known as the can-do kid, because in those days, you know, if you could just take anything, I'd run with it, and that was fun, because we were building things that had never been built before, right?

AI assessment note: “I moved out to Silicon Valley in the late nineties when the dot-com boom”

Q So if you wanted to found a tech startup in today's environment, what would you advise an entrepreneur who maybe doesn't have the technical coding skills to build a product today?

A Uh, first, um, don't do something that you, because you think a market's hot, because markets, uh, cool, and, you know, like, uh, you know, when, when YouTube first launched, there were like, you know, 30 YouTube clones came out, right? Now, the, the YouTube guys, I knew them in the beginning, they were doing something that they really cared about, and they were able to, you know, recruit the best people, you know, because they networked in what they were doing. Um, it always has to be something you really care about, because fundamentally, you may be giving, more often than not, Here's the thing. You're going to give about three to five years of your life, and your odds of failing are 90 plus percent. Right? So if you're going to do that, you better be in something you care about. It's a problem you want to solve. That is the fun, the first most important thing. Then, when you do that, Then, you know, like, uh, the best ones actually don't sit around and saying, well, I need, uh, you know, cause I meet people all the time. Oh, this great idea. I just want to sell it to someone. They do it. That does not happen. You know, it's, it's, it's, uh, it's, it's actually no one value values ideas and rightfully so ideas and nothing is ideas in action that actually make any difference. Right. So that's application. So if you don't know how to code, you know, like, Take, go join Coding A…

AI assessment note: “So if you don't know how to code, you know, like, Take, go join Coding Academy.”

Q So if you wanted to found a tech startup in today's environment, what would you advise an entrepreneur who maybe doesn't have the technical coding skills to build a product today?

A Uh, first, um, don't do something that you, because you think a market's hot, because markets, uh, cool, and, you know, like, uh, you know, when, when YouTube first launched, there were like, you know, 30 YouTube clones came out, right? Now, the, the YouTube guys, I knew them in the beginning, they were doing something that they really cared about, and they were able to, you know, recruit the best people, you know, because they networked in what they were doing. Um, it always has to be something you really care about, because fundamentally, you may be giving, more often than not, Here's the thing. You're going to give about three to five years of your life, and your odds of failing are 90 plus percent. Right? So if you're going to do that, you better be in something you care about. It's a problem you want to solve. That is the fun, the first most important thing. Then, when you do that, Then, you know, like, uh, the best ones actually don't sit around and saying, well, I need, uh, you know, cause I meet people all the time. Oh, this great idea. I just want to sell it to someone. They do it. That does not happen. You know, it's, it's, it's, uh, it's, it's actually no one value values ideas and rightfully so ideas and nothing is ideas in action that actually make any difference. Right. So that's application. So if you don't know how to code, you know, like, Take, go join Coding A…

AI assessment note: “if you don't know how to code, you know, like, Take, go join Coding Academy.”

Q And then in terms of going back to your days of WebMD, and you said you learned a huge amount back then, what was your biggest takeaway from that experience?

A It was all we, we learned by doing, because whatever we were doing, no one had built before. You know, I helped build the first EMRs, the stuff that they're building now, we were building them in the late nineties. No one had done it before, so we just figured it out. That was the best education, because you'd learn as an entrepreneur. You know, I was talking with a friend of mine yesterday. She's a very successful entrepreneur in New York City. She, she runs the biggest, uh, Pole dancing studio in the country, right? I got a tour of that, and let me tell you, as a man to watch, you know, all these pole dancing, women pole dancing, it was a lovely tour.

AI assessment note: “we learned by doing, because whatever we were doing, no one had built before.”

Q And then in terms of going back to your days of WebMD, and you said you learned a huge amount back then, what was your biggest takeaway from that experience?

A It was all we, we learned by doing, because whatever we were doing, no one had built before. You know, I helped build the first EMRs, the stuff that they're building now, we were building them in the late nineties. No one had done it before, so we just figured it out. That was the best education, because you'd learn as an entrepreneur. You know, I was talking with a friend of mine yesterday. She's a very successful entrepreneur in New York City. She, she runs the biggest, uh, Pole dancing studio in the country, right? I got a tour of that, and let me tell you, as a man to watch, you know, all these pole dancing, women pole dancing, it was a lovely tour.

AI assessment note: “we learned by doing, because whatever we were doing, no one had built before.”