James is a sales & marketing focused startup guy. At last count James had run seven startups – and is working on his eighth: Cognome, a tech spinout from the Montefiore Health System in New York City. He’s also the founder and a board member of Open Squash a 501(c)(3) non-profit whose mission is to make squash more accessible. They opened their first location in Manhattan in January 2020 and are poised to open two more locations in NYC by Sept 2024 – you should join!

Other fun facts:

At Magnetic (which James ran from 2011→2017) he grew revenue from $1 to $100 million before it was sold to Deloitte.

He ran PVI which is now owned by ESPN and is the technology that ESPN uses to show the first down lines in (American) football and other virtual objects in all their sport programming.

James was CEO of the World Series of Video Games, one of the pioneers of e-sports; and

He got his entrepreneurial inspiration from Steve Jobs whom we worked for at Pixar Animation Studios where he ran marketing and new business development for Steve.

James is happily married with two children despite having made his family live on a boat for a year while they sailed around the world (2010-11).

He graduated from McGill University where he occasionally guest lectures (B. Music – ‘cello), and holds an MBA from the Anderson school @ UCLA.

Key Moments

[00:03:45] Entrepreneur with music background gets MBA at UCLA.

[00:07:22] Successful sale, but sued for patent infringement.

[00:11:10] Being early can be a costly entrepreneurship lesson.

[00:13:35] Nonprofit makes squash accessible in Manhattan.

[00:16:27] Data stays in place, but can be combined.

[00:20:39] Responsibility, transparency, humility as an entrepreneur.

Find James Online:

https://linkedIn.com/in/jamesangreen

https://www.opensquash.org

https://www.cognome.com

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Transcript (Provided by CastMagic.io)

Seth [00:00:00]:

Entrepreneurs Enigma is a podcast for the ups and downs of entrepreneurship, the wins and the fails that we all face being entrepreneurs. How we learn from adversity. Every week, I talk to a different entrepreneur with a story to tell. I’m Seth Goldstein, come with me on the journey. This is Entrepreneurs Enigma. Let’s get started. Hey, everyone. Welcome to another edition of the Entrepreneurs and Think of a podcast. I’m your host, as always, Seth. Today I am here with James Green. He is a consummate entrepreneur. He is a startup guy. He’s on his 8th startup and he’s pretty much done it all. I’m sure there’s still some stuff he’ll figure out that he hasn’t done and then he’ll do. You know, he is quite the renaissance man when it comes to startups. And it’s not just one vertical. With startups, he does everything from squash through biotech, through healthcare. He’s interesting. Dude, I think you’re going to enjoy this. Hey, James. How’s it going, buddy?

James [00:01:13]:

Hey, Seth. I’m good, how are you?

Seth [00:01:15]:

It’s also got the good British accent.

James [00:01:19]:

Yeah, I put it on specially for the podcast.

Seth [00:01:21]:

Oh, there we go. There you go. And also, did I see in your bio that you got to have a bachelor’s in music in cello?

James [00:01:28]:

Yeah, I was originally a musician.

Seth [00:01:32]:

Not surprised.

James [00:01:34]:

I very, very briefly played off stage cello for the Montreal Symphony Orchestra. They needed some extra Cellus for some marla.

Seth [00:01:42]:

Of course, why not? Let’s throw that into the repertoire of what you’ve done.

James [00:01:46]:

There you go.

Seth [00:01:47]:

And he’s not 100 years old either. He’s done a lot.

James [00:01:51]:

You know what? I do feel like I’m 100 years old.

Seth [00:01:53]:

Well, honestly, you do like to snowboard and you did take a tumble. So, before the show, James would show me a picture of his nerve damage, where when he gets flush, only half his face flushes. It’s very interesting. Straight line, right down the middle. It’s very cool.

James [00:02:09]:

Freaky.

Seth [00:02:10]:

Freaky. Hey, you have to have some freakiness in the world, right?

James [00:02:14]:

There you go.

Seth [00:02:15]:

So how did this all get started? You grew up in the UK, you went to school in Canada, you were a cellist. I think that’s what the plural is, right? Or the word is.

James [00:02:26]:

How did it all get started?

Seth [00:02:28]:

How did you get into the entrepreneur space? How does someone get into eight startups?

James [00:02:33]:

Well, so I think that all musicians are entrepreneurs. If you think about a musician’s life, they are forever trying to find gigs, trying to make money and hustling hustling. I don’t know a musician who isn’t an entrepreneur, and I don’t think people think of it that way, but they absolutely are. And in some ways, it’s the hardest form of entrepreneurship because no one gives you money.

Seth [00:03:05]:

When they give you money, it’s not that much.

James [00:03:08]:

Right? And so what happened to me, I realized when I was about 2021 that I was not good enough to be a professional musician. I still gave it a few more years. After that, I gave myself till 24. But at 24, I realized that wasn’t going to work out for me.

Seth [00:03:30]:

That’s very introspective of yourself.

James [00:03:32]:

I remember actually at 19 telling myself that I had till 24, which at 19 felt like a really long time and very older.

Seth [00:03:44]:

Recession speed up.

James [00:03:45]:

Yeah. It feels like I was still in diapers, but there you go. And so then I went because I had nothing but music background. I mean, some DJing. And I was doing other kind of entrepreneurial things like that. I did have a DJ company that was doing about four or five parties a night on the weekend. So had about a hundred freelancers working for me. So I did have some entrepreneurial business. But I went to took an MBA at UCLA.

Seth [00:04:17]:

That’s all. At UCLA. Fantastic school.

James [00:04:20]:

Yeah. And I think I got in because I was a musician. I had done all of these other things. And they were looking for diversity.

Seth [00:04:30]:

The British who studied cant in Montreal.

James [00:04:32]:

Yeah, that was French.

Seth [00:04:34]:

That does a cello, an MBA.

James [00:04:37]:

That was the 1980s version of diversity. Diverse. And that’s how it started. I worked for a company that was doing startups. And then they told me I needed some corporate experience. I worked for the Walt Disney Company. But even in the Walt Disney Company, I did startup things because they divorced Warner Brothers at the time. And then I traveled around the world setting up their subsidiaries for them.

Seth [00:05:04]:

Oh, that’s fine.

James [00:05:05]:

And I learned a lot about how to run a business because each of these countries were little businesses. And I set them up for them.

Seth [00:05:13]:

On the job training.

James [00:05:14]:

Yeah. So spent eight years doing that. And then I had my 15 minutes of fame. We released Toy Story pixar’s first film. Got to know John Lasso, who had directed it, and his wife. And I was sort of the guy at Disney who thought it would do better than everybody else. Everyone thought it would be a little film. And I’m like, dude, it’s going to be massive.

Seth [00:05:37]:

Oh, it was good. The first one was so much better than the next four.

James [00:05:41]:

And the other ones are good. But the punchline is I got to meet Steve Jobs and he hired me. I worked for him directly at Pixar to manage the sort of the marketing of their movies.

Seth [00:05:56]:

We worked directly for Steve Jobs. Wow. That was an did.

James [00:06:01]:

I did.

Seth [00:06:02]:

And you survived.

James [00:06:04]:

No, I did not. I didn’t last very long. I got hired and fired by Steve Jobs in the same year. Steve Jobs.

Seth [00:06:12]:

It’s an experience. It’s something you can check off your bucket list. Working and getting fired by Steve Jobs. We’re going to take a quick break here from our sponsors and get right back to the show.

James [00:06:20]:

Yeah. And then after all of that experience, I decided to start my first sort of what we would think of as a startup. But you can see that all of that experience, I was kind of doing startupy things.

Seth [00:06:32]:

Exactly. So you’re kind of ready to do your own thing, and then you ran something called magnetic.

James [00:06:39]:

I did.

Seth [00:06:40]:

Was that the one where there was the ESPN line judge thing? Where is that the line thing?

James [00:06:45]:

No, I’ll walk you through them.

Seth [00:06:47]:

One that was a fun one that you had this line thing figure out.

James [00:06:51]:

The first one I did was called Sabella. That was like double click. It was an ad server back in Nine. It was good. We sold it to 24/7 Media in a bidding war between them and Double Click, actually.

Seth [00:07:05]:

Oh, wow. You got into a bidding war. That’s fun.

James [00:07:08]:

That was truly dramatic. As I said to you before the call, if you can imagine it, I’ve experienced it at this point.

Seth [00:07:18]:

Imagine hell. You worked for Steve Jobs. That’s a hell of an experience right there. Jeez.

James [00:07:22]:

So that one, although it ended well, we sold it for 75 million, which is not bad for we sold it in January of 2000 for 75 million. I owned 17% of the company. Not bad for a first hit go at bat. But what happened was I was raising a round of financing, was all going great, everything done. The weekend before we were supposed to close, we got sued by Double Click for patent infringement.

Seth [00:07:50]:

Oh, no.

James [00:07:51]:

Two weeks of cash left and they sued me. And then no one wired the money because they said, Change in condition. We didn’t agree to invest while you were being sued by Double Click. And so I had two weeks cash, no money. I did an emergency round of financing. Another little trivia fact. It was led by Malcolm Turnbull, who ended up being Prime Minister of Australia. But there you go.

Seth [00:08:17]:

You’re collecting notable people, like playing cards here.

James [00:08:20]:

Yeah, that’s right. We fought the patent. That happened in the first week in December, and then about five weeks later, we got bought by 24/7 Media because they had a patent that they thought would stand up in court against the patent that Double Click did.

Seth [00:08:40]:

Wasn’t Double Click trying to buy you, though?

James [00:08:43]:

They did. They sued us on Friday and tried to buy us on Monday, but they tried to buy us for $5,000,000.75.

Seth [00:08:51]:

Yeah. Get lost. Double click. And then Double Click was bought by Google anyway.

James [00:08:56]:

So yeah, that IP stuck around somewhere.

Seth [00:08:59]:

In Google, but it’s somewhere out there. It’s probably in Google somewhere. Yeah.

James [00:09:04]:

So then I did another wasn’t hugely successful, I think a wireless startup called Giant Bear. We sold to what was InfoSpace at the day?

Seth [00:09:14]:

Oh, InfoSpace. I remember InfoSpace.

James [00:09:19]:

What did they change their name to? I forget.

Seth [00:09:21]:

Who knows? They’re not here anymore.

James [00:09:24]:

And then the next one is what you were referring to, which was TVI Princeton video image.

Seth [00:09:31]:

That’s the one, yeah.

James [00:09:33]:

Which was famous for inventing the first I didn’t at that point, my career had moved from being the entrepreneur to getting hired by venture capitalists to run their companies, which is really that’s kind of fun, which is really what I have done for the last 20 years.

Seth [00:09:51]:

So up until they drop you in like a paratrooper, you drop in and you say, oh my God, this is a mess.

James [00:09:58]:

Well, life is messy.

Seth [00:10:01]:

Life is messy, exactly. The first downline thing.

James [00:10:06]:

Yeah. So that was exciting. So we did that, and that ended up being sold to ESPN. So it’s still around, which is great.

Seth [00:10:14]:

So you can see that I built that. That’s kind of cool. I built that’s. Cool.

James [00:10:19]:

Yeah. I think the most rewarding thing, not the money and all of those things, but the most rewarding thing is to see the thing that you built continuing to be used and to be useful in the universe. And PVI is a great example of that. I do want to emphasize that I didn’t build that. Someone at some really talented guys, ex intel guys, mostly built it, and I just came in and ran it just.

Seth [00:10:41]:

For the fair enough. But you had your hand in it, which is kind of like you helped get it bought by ESPN, which got them a nice payday. I’m sure. I’m sure they’re happy about that.

James [00:10:51]:

And then I did another fun one, which I really loved. Again, not a huge outcome. The World Series of Video games. We were the first large esports company. This is in like, oh, God, 2008, maybe.

Seth [00:11:09]:

Oh, so you’re before the times.

James [00:11:10]:

Yeah, we were early. This is a huge lesson in entrepreneurship. You can do things early and sometimes they pan out. Sometimes, yeah, you’re just too early. Like way back in the 80s, for example, I had a company called DD Distribution that I was working with that did videotape rentals by those oh, wow. By mail. It was like Netflix before there was Netflix, and it didn’t work before there was DVDs. It didn’t work because the videotapes were too expensive to ship.

Seth [00:11:42]:

And he.

James [00:11:46]:

Can you know, timing is everything was really fun. That was a really good one.

Seth [00:11:50]:

We did sell the company, but you meet something.

James [00:11:55]:

Then I took a year off, actually, after that.

Seth [00:11:57]:

Well deserved, I’m sure. After all, you take a year off.

James [00:12:01]:

I did the thing that probably I’m actually most proud of. It’s not entrepreneurial and it’s not financial. It’s not at all. And the thing my wife, my kids and I took a year, bought a sailing boat and sailed. Lived on it for a year, sailed down to the Caribbean, then crossed the Atlantic and then ended up in Turkey. So sort of winter in the Caribbean, summer in the Aegean, and then came back to work.

Seth [00:12:26]:

That’s a nice little break.

James [00:12:28]:

Yeah.

Seth [00:12:29]:

Let’s talk about getting away from it all.

James [00:12:32]:

Yeah.

Seth [00:12:33]:

When you’re in the middle of the Atlantic. You’re away from it all.

James [00:12:37]:

That is definitively true.

Seth [00:12:40]:

Oh, my God. And so then you’re helping out with open Squash, which is a 501 c three nonprofit. Squash More. We’re not talking about the vegetable people, about the game. Yeah, my dad was very big in squash before he blew out his knees. But he’s like, Racquetball sucks. Squash is the game. And I’m like, all right. Wherever you say, dad.

James [00:13:06]:

I mean, he was right. Squash is the game. Squash is an amazing sport. I loved it so much that when the place that I was playing squash shut down. Squash is really a niche sport in the world, if we’re being honest.

Seth [00:13:24]:

It’s very in New York, too.

James [00:13:26]:

Yeah. It’s certainly big in New York and Philadelphia. It’s also big in England and and.

Seth [00:13:32]:

Everywhere that James has been, it’s big. There you go.

James [00:13:35]:

Big in the English Commonwealth. It’s big in Egypt. Never been really? Yeah, yeah. Egyptians are the best in the wow. But when the club that I was part of shut down really? Squash in the city was restricted only to private clubs, and I kind of hated that idea that I had to apply and go with references. I just wanted to be like a gym, just something that everyone could do. And so myself and a couple of other people founded this nonprofit where the mission of the nonprofit is to make squash more accessible. And we’ve opened our first location right in the middle of Manhattan, 39th between fifth and 6th.

Seth [00:14:20]:

Oh, nice.

James [00:14:21]:

And we’re opening the second one. We’re sold out at that location, by the way.

Seth [00:14:26]:

Wow.

James [00:14:27]:

And we’re opening the second one in the fall, I hope. September 1, maybe it’ll slip 30 days. We’ll see.

Seth [00:14:36]:

So you don’t sleep. In addition to that, you also do Cognome, which is your newest startup.

James [00:14:43]:

That is true. Oh, my gosh. I haven’t even publicly announced it. So here’s the official publicly public announcement, which I’m fine. I’m not trying to hide it, but we haven’t actually you’re not making a.

Seth [00:14:57]:

Huge, big deal about it.

James [00:14:58]:

No, I’m not.

Seth [00:15:00]:

That’s the cool one. What is Cognome? Can you explain it briefly? Because I am not even going to try I understand it, but trying to reiterate it, I’ll forget it.

James [00:15:08]:

So Cognome is a spin out of the Montefiore health system, which is a large health system here. When I say here, that’s because where you’re calling me from in the Bronx, in New York. So I actually, as part of this, moved to the Bronx.

Seth [00:15:24]:

Oh, wow.

James [00:15:25]:

And they built some tech. They decided to spin it out, and they hired me as the CEO to spin it out. So it’s the first time that I’ve been hired by a non VC to.

Seth [00:15:34]:

Run a company, which is that’s exciting.

James [00:15:38]:

And what they do at a high level with sort of the ideas of privacy and control, first, keeping the data in the hands and control of the individuals and the providers. So if you’re in healthcare, there are two people that generate data. It is the patient, it’s obviously your data, and the doctor. They’re also helping create the data. Right. So keeping that concept first, we are basically trying to do for healthcare data what Google did to the Internet, which is safely but safely to make it.

Seth [00:16:15]:

Unlike Google, seems to trip over itself constantly. How much do they trip over? Or they’re just evil? One or two.

James [00:16:21]:

So ours is we use what’s called a Federated model.

Seth [00:16:26]:

I know, Federated.

James [00:16:27]:

Yeah. So that means that all of the data stays resident in the place it was created. But the tech can bring it all together. So you can query multiple places, but unless the place gives you permission, you can’t see it. And there’s multiple levels of permission. You could see it in only aggregated. You could not see it. You could see it only in aggregated form. You could see it deidentified, or you could see it at the patient level. Sometimes you do need to see it at the patient level. If you’re going to do a clinical trial, for example, you need to reach out to the patient to say, would you like to be in this?

Seth [00:17:00]:

Cool. It sounds like fun.

James [00:17:01]:

So it’s kind of awesome. And if people want to sort of look up what it is an extension of, then there’s an open source system that we’ve built, a huge set of extensions. And I’m saying that the extensions are so big, it’s like comparing a go cart to a Formula One car.

Seth [00:17:20]:

Oh, wow.

James [00:17:21]:

Weather formula one car.

Seth [00:17:22]:

Yeah.

James [00:17:24]:

There’s an open source movement called Odyssey, which is oh, D si.

Seth [00:17:29]:

Of course. It can’t spell correctly. Of course.

James [00:17:31]:

No. But they use a data format called OMOP and a query tool called Atlas. And we’ve taken all of that and done some incredible things with it to make all of this possible. I’m super excited about it. We have a couple of clients that we’re just sort of testing with. Totally unannounced.

Seth [00:17:51]:

Yeah, we’ll make sure it.

James [00:17:55]:

Super. I mean, it’s really from zero, except for the fact that it’s already being in use by the Montefiore health system.

Seth [00:18:02]:

So it’s kind of been dog fooded a little bit.

James [00:18:06]:

Yes, 100%.

Seth [00:18:08]:

That’s very cool. So you’ve done the entrepreneur thing, you’ve done the fly in and manage the company thing, you’ve done the corporate thing, you’ve done the internal entrepreneur thing, you’ve done it all, pretty much. What is the scariest thing about being an entrepreneur head of Things guy?

James [00:18:25]:

The scariest yeah.

Seth [00:18:26]:

What’s the scariest thing about it? Because you go in there to me.

James [00:18:29]:

That’S actually super easy. The scariest thing is being responsible for payroll. Multiple times in my life, I have seen that cash is shorter than the runway that I need. And for sure, the scariest thing is seeing these people that you I’m going to say that you love this ends up being your family and you don’t know what’s going to happen. I’ve had to fire friends just to give you the worst example of that. One of the companies I was running, it was called Giant Bear. It was this mobile data company that was sold to InfoSpace. We lived through 911.

Seth [00:19:09]:

Oh, wow.

James [00:19:10]:

And we had to shrink after 911 because the economy was shrinking and you couldn’t sell diddley squat anything. I ended up having to fire a guy who lost his brother who was a firefighter.

Seth [00:19:25]:

Powers oh, that’s painful.

James [00:19:29]:

We’re both crying, for sure. It’s being responsible for payroll and the fallacy that sometimes you’re in control of it because not so much, that’s for sure the scariest thing.

Seth [00:19:47]:

But then the flip side, what’s the best thing about being an entrepreneur?

James [00:19:51]:

I’ve sort of said it already. The best thing is being able to step back and look at what you’ve built and see it standing by itself. It’s quite like parenting. Yeah.

Seth [00:20:00]:

It’s your babies are out there. Your baby the downline thing is like.

James [00:20:04]:

Yeah, you want to help your babies grow, and then you want to help them be self sufficient. And to me, that moment when they become self sufficient and they don’t need you anymore and you can see what they’re doing, that’s priceless.

Seth [00:20:18]:

That’s awesome. And so what’s the most important thing to carry with you all the time?

James [00:20:23]:

The most important thing to carry with you all the time? Not your phone.

Seth [00:20:27]:

No, that’s definitely something you have to carry with you especially. Yeah.

James [00:20:33]:

The most important I’m going to say something a little cliche.

Seth [00:20:37]:

I’ll go for it.

James [00:20:39]:

My only defense is I’ve been saying this longer than it’s been cliche to say it, which is your honesty and your transparency. I think the thing that you need to carry and maybe your humility to go with it, if you’re an entrepreneur, you are responsible for theoretically, at least one other person. It’s pretty rare. Unless you’re a musician, you’re all alone. It could be one, it could be 100, it could be several hundred. And these people’s lives are as important, maybe one could argue more important than yours, and you hold a large portion of it in your hands. And I think that people allow that to go to their head when what should happen is the know, you should have humility about it. You should sort of admit when you don’t know what’s wrong. There’s vanishingly little of that in the world. Know, I used to be an admirer of Elon Musk, but now he can’t seem to admit when he’s wrong, which to me is the know Donald Trump’s the same. These people cannot admit they actually see admitting of failure or admitting that you’re wrong as a weakness.

Seth [00:22:07]:

No, it’s a strength.

James [00:22:08]:

And I see the opposite. I just see the opposite. And so absolutely, that openness and transparency and honesty, authenticity and humility. And you asked for one thing, but I kind of think of their they.

Seth [00:22:23]:

Kind of all go together.

James [00:22:24]:

Yeah, that’s the one thing that I do my best. I’m by no means perfect at it, at carrying with me all the time.

Seth [00:22:33]:

And then best place to find you is probably you hang out on LinkedIn. This is your online watering hole, right?

James [00:22:38]:

Yes. So best place to find me, sure. Message me on LinkedIn. But I answer every email, every text he does. The worst place to find me is cold. Call me.

Seth [00:22:49]:

No LinkedIn email. We’ll do that.

James [00:22:52]:

You can text.

Seth [00:22:53]:

Yeah, calling is overrated it’s so interruptive.

James [00:22:58]:

I got a lot of stuff going on and you call and need I need the setup to be asynchronous.

Seth [00:23:06]:

Amen. Amen. James, this has been so much fun. Thank you for coming on. I’m glad we got this rocking and rolling. I know it’s been a little bit time in the works getting you on the show, but I’m thrilled. This has been so much fun, my friend.

James [00:23:20]:

I can’t believe the time is up already.

Seth [00:23:22]:

Oh, I know. It’s been so much fun. So we will see everyone next time. Okay? That was a great show. If you’re enjoying entrepreneurs Enigma, please view us in the podcast directory of your choice. Every review helps other podcast listeners find our show. If you’re looking for other podcasts in the marketing space, look no further than the Marketing Podcast Network at marketing podcasts. Net. Hopes you have enjoyed this episode. This podcast is one of the many great shows on the MPN Marketing Podcast Network.