Jeffery:
you know what? Today we’re going to chat about startups and all that good stuff, so I’m excited that we’re getting to chat and learn a little bit more about yourself and what you’re up to today. And like we like to do, we just jump right into it. So welcome to the Supporters Fund and the OPN ask an angel and today we’re getting the opportunity to chat with you jim. And at the best way for us to start is if you can share a little bit about your background, kind of where you’ve come from, where you’re at and where you’re going. And then one thing about you that nobody will know.

Jim:
Oh boy, I’ll come to that later, I’ll do the easy part first. Let’s see. So I grew up in the northeast of the United States, was born in New York city, raised the burbs and did all my school in the Northeast and um followed a lot of different paths.

Got married very young, uh really hung and and we had a little boy little then and uh ended up in banking really because of necessity I was really more interested in the arts, but you know I had the mind for it, so I just decided that I was going to bankrupt myself, my family was going to starve unless I did something more practical, so became went straight to work with the savings bank and then went to work at AIG a subsidiary of AIG And then went to business school at night. So I went to Stern school, I got my business degree, was a banker for a while and then kind of hit a bad timing, wrong place wrong time. And um you know, having had a pretty good career, I was doing latin America, which was very, things had to be right. And then um instead of like sticking with it, actually did a little startup work for some different companies, not really from the bank of perspective. And then instead of just staying in and went back, moved down to Florida, just kind of packed up, I was divorced, moved down to south beach Florida and was managing some money for my family.

So I was in the investing side of things and then fell into really the wrong way into startups and I say the wrong way because I wasn’t doing it directly. I was listening to other people and made some big mistakes early as a lot of angels do. I’m sure you’ve talked to a lot of people and you know, some people will make a mistake and run and others will say, shoot, I gotta figure this out and I got to make it back. So that’s what I did. And this is a long intro, but I’ll finish it in a couple of sentences. So basically what happened was I decided that, you know, having done more, reading that the way to do it was to make lots of smaller bets, which is still our strategy at Barrister Ventures.

And then, um, I found some other people like me um, after I tried the angel group, which I didn’t like and then I found people like me is that we formed, we formed this, um, this company and so that’s it. We’ve invested in 103 companies so far.

Jeffery:
Awesome. Yeah, that’s brilliant. Uh, and what’s the one thing about you that no one would know.

Jim:
Oh my gosh, can I come back to that? Little occurred to me. I don’t, I’m terrible at like recall. Um, I’ll tell you one that’s venture related and actually some people do know this and he probably would hate to hear me say it.

But I played on the JV baseball team and the varsity football team at Andover phillips academy and over with Tim draper.

Jeffery:
Sick.

Jim:
Yeah

Jeffery:
That’s pretty cool.

Jim:
That’s a good story for you here. I mean, you know, we weren’t like close buddies or anything, but you don’t know, we got that close to those days, but um

Jeffery:
Anything that you remember from then, like a story that you’re like?

Jim:
Yeah, I do actually, I’ll tell you one story that’s kind of fun and the reason I’ve always remembered it, but it was actually in his book. So his dad was a famous, look, I don’t want to be, you know, comparing myself to Tim Draper. Let’s just get that clear.

But Tim is super successful, has been doing it for decades, is where billions of dollars. Um But you know, I’m I’m very much an amateur by comparison, but you know, I I did I did go to high school with him and so I did read his book and his father’s book and his father was actually one of the original venture capitalist in America and he worked for the XNM. Import bank. I was actually when I was a banker did work with them. Um so I understood that and he, you know, he was a big deal in the Bush senior, you know whatever HW Bush administration and elsewhere and so um and so I read his book and Tim’s book, which is you know, it’s a little different tips book, but he mentioned an anecdote from football in high school about his friend, I forget his name, but his best friend growing up, they were inseparable how he went to Deerfield and when Deerfield was playing Andover, his friend broke his nose because they were opposite each other.

And I remember being on the bus going back and Tim had left the field with a broken nose and he was on and he said to us, I think he was a little bit woozy, you know? He said um I asked the doctor if I’d be able to play lacross the spring and he said sure. And he said that’s amazing, you’re amazing doctor because I played baseball there, but neverplayed lacross my life. So it’s stuck with me. It’s not that’s hysterical, by any stretch. It’s not exactly, you know, I comedy, but I do remember that.

Jeffery:
And did you remember because he became famous or just happened to be?

Jim:
No, no, it’s stuck with me. No, no, I, you know, I don’t really have so many distinct memories from high school. It was a long time. I hate to tell you we graduated in 1976. Long time ago. So no, certain things stick with you and I don’t know why that did. I couldn’t tell you anything else about that day.

Jeffery:
Amazing. Well, it’s still pretty cool. Um, well, I love to, to kind of go back and talk a little bit about, um, down the investment side where you said you ran into the problems and the main things that everybody seems to face and I’m not sure everybody faces them, but they face the, and what you did mention, which is that they usually bolt. Um, and that’s because I think that there’s this perception that I’m gonna fly into this new category.

I’m going to make a couple investments, make some big money and then fly out. And it always seems to be the opposite of that. Maybe you can share a little bit about that experience. And what was the downside that you came across and how did you overcome it? Because it sounds like you were doubling down. You’re like, you know what? I screwed up and no one’s taking my money, I’m going back and I’m gonna find a way

Jim:
I’ll answer question number two, and the easy answer is stupidity, right? I mean, stubbornness and stupidity is why I double down. You know, there’s nothing really I’m not really proud of of anything.

You know, I can say on, on your podcast, I