Andy Russell, 42, founder of Trigger Media, was the lead investor in DailyCandy and Thrillist under Bob Pittman’s Pilot Group. Focusing on digital media, Andy has invested in more than 50 companies over the past 15 years, including TastingTable, Ideal Bite, VitalJuice, GeekChicDaily, Zynga, Betaworks, Silicon Alley Insider, GroupCommerce, Room77, Huddler, Spongecell, HomeRun and AdRoll. His newest ventures include InsideHook and Host Committee, which help people get the most out of New York City and all it has to offer—and party like rock stars before 9 p.m.
Tell me where this entrepreneurial journey began. It all started before college, when I threw parties for kids here in the city. I rented out ballet studios, hired DJs and bouncers and charged 20 bucks a head. We had all the cool kids on the list from each school.
How did you know where all the cool kids were? I was really social and a shitload of fun. I was also a tremendous flirt—I knew what time the girls at schools like Spence and Chapin got out, and I was always outside their building.
What’d you do after college? I was working over 100 hours a week in investment banking and throwing parties on the side. I raised $1 million and opened Moomba, a restaurant and club, with investors including Oliver Stone and Laurence Fishburne. It became the hottest club in the city. I was 25 and started growing my long hair and wearing leather pants, hanging out with Leonardo DiCaprio, Madonna, Sting, Donald Trump, Mike Tyson, Puff Daddy …
And the next logical step was to link up with the guy who founded MTV. Bob Pittman, yes. We started Pilot Group and raised $800 million.
Early on, you invested in some companies that didn’t do too great, though. One of the Israeli companies I invested in was called EverAd. It was basically Spotify, but I launched it in 1999, and it was too early for its time. The music labels weren’t ready to play ball with digital music. Then I invested in Pay2Card, which was basically PayPal, but again, it was before its time in 1999. When PayPal came around, they ate our lunch.
So what kind of company catches your eye and makes you think that’s going to make me money? It’s all about the entrepreneur. For example, if he’s mediocre-looking and he has a ridiculously hot girlfriend, that means he’s a good salesman. The same goes for women.
And once you’ve established that they can land a dimepiece, how do you weed out a good business model? It’s not about something that creates a ton of users, followers or “likes.” I invest in companies that make money the old-fashioned way. I don’t like betting on companies where I’m hoping some “strategic” is going to overpay for my company. I want real companies that build real relationships with consumers that solve real problems. What problem are you solving for the consumer? That’s the question.
What companies have spoken to you in that way recently? InsideHook is a city guide email for adventurous and established men—guys who have limited time but discerning taste and a thirst for experiences. We recently signed Ed Burns, Rob Lowe and Tim Ferriss as partners and curators. The problem they’re solving is this. Guys like me, we fall into a rut in our own city. When people go out with their friends, they go to the same steak joints, drink a little too much, tell the same funny stories, and the memories blur. Why not go on a boat with friends in the harbor at sunset and go striped bass fishing? Those are things you remember, and those memories exist in New York City.
And the other big one is Host Committee. In a city that never sleeps, it’s ridiculous that there’s nothing to do between 7 p.m. and 12 a.m. Everything’s closed. There’s nowhere to party and dance. It doesn’t exist. Then, at midnight, if you want to go with seven to 10 friends, it’s a hassle at the door. You won’t all get in, or none of you will, or you’ll have to throw down $2,000 for a $20 bottle of alcohol and be hungover the next day.
Is that how you ran the door at Moomba? Nope, you couldn’t even buy your way into Moomba. You had to be that fabulous. It was nauseating.
But back to Host Committee. Right. So the problem is: What do you do after dinner? With Host Committee parties, you can gather as many friends as you want, and you have something to do after dinner. It’s like Uber for nightlife. It opens up the best of New York City nightlife in places that were previously closed before midnight. Basically, anyone can host their own private soiree for free at the most in-demand venues in the city, like Marquee, the Darby, Jimmy, Dream Hotel, etc.
What do you collect? Any art? No. I collect young entrepreneurs, and I collect businesses. They are my art, my toys and my game.
Invest in any stocks? Yes.
What stocks? Apple.
What else? You know what? I don’t know, because I’m not an expert. I send all of my money to my dad to do it for me, because he’s a professional. If you’re going to invest capital, you’d better be an absolute freakin’ expert, or you’re going to be beat.
You’ve invested a lot in your house in North Salem. I would say multiple seven figures, yes. There’s a pond that we canoe in, an 80-foot zipline, a movie screening room with seats that sculpt to your body, and I have a barn that I turn into a nightclub, with a pool table, a full-on sound system and a—what do they call it? A reflective ball?
A disco ball. All in all, would you say partying is your greatest investment? From the age of 16, I have been studying the psychology of partying, networking, socializing. By building up a great reputation, everyone will always want to work with you, for you and invest in you. I don’t care how much money someone has. Without a good reputation, you have nothing.
Anything else you invest in? Well, I recently lost 37 pounds after investing in my trainer, Calvin. I don’t even know his last name, but I pay him a lot to kick the shit out of me.