In my “regular” job as a start-up brand consultant and advisor, I get to meet a lot of different investors: angels, dumb money, smart money, venture capitalists, vulture capitalists… and it’s surprising how few of them are not only smart and savvy but also honest, humble and not boring. Most VCs, in fact, just follow other people’s bets and rarely have original ideas, but I digress…
Dan and Paul are two of the good ones. I’ve known them since my days at Yelp (when the company was a part of Max Levchin’s first incubator), so it’s been rad to see their successes (early bets on Uber, Unity, Zappos, and Stripe) pay off over the years. They have fun, too: Paul remains one of my favorite Wikipedia entries while Dan “re-invests” his money by collecting Legos, having earned the title of “cool guy” from my son Dash.
This is the first double interview for In Search Of Lost Answers — and these bros wouldn’t have it any other way.
Nish: What is your idea of perfect happiness?
Dan: A nice weekend bike ride followed up with a home-cooked meal.
Paul: That magical moment when you planned an amazing trip or dinner and you’re about 2/3rds of the way through and it’s on autopilot. You get to start to enjoy and watch everyone in their element.
Nish: What was your worst job ever?
Dan: A short-lived temp job in sales at a church I wasn’t even a member of. I was calling other churches offering courses on how to increase attendance and engagement. I was not good at this job.
Paul: Arthur Andersen… quit within 9 months. Wasn’t bad per se just boring and had a 90-minute commute each way.
Nish: What was your first job ever?
Dan: Caddy at a golf course. I think I worked a total of 2 days.
Paul: I worked at CompUSA in the Accessories department. This was a fun and innocent time and was just as I was getting into computers.
Nish: What was your best job ever?
Dan: Beer Vending, primarily at Wrigley Field in Chicago. Worked there full time for 3 years. I was a union card holder working football games, concerts (Rolling Stones, Bon Jovi, Jimmy Buffet) Nascar, Kentucky Derby. It was awesome! Got to watch my favorite team play for free AND get paid. Plus a great workout.
Paul: Probably my first startup Paragon5. Started it to make my dream come true of making games and got paid handsomely for it. A particular low but funny point was when one of my games was honored with the title of worst game box art! Luckily it was a well-reviewed game.
Nish: What is the trait you most deplore in yourself?
Dan: My procrastination.
Paul: I’m messy and super disorganized.
Nish: What is the trait you most deplore in others?
Dan: Tardiness, canceling plans last minute.
Paul: Lack of ambition & dreams.
Nish: What’s some advice you’d give to yourself at 23?
Dan: At 23 I was living in Hawaii with my brothers sporting a mohawk rattail. Overall I’d say keep it up, you’re doing great. Just don’t go to law school!
Paul: You’re ahead of your time. Stay the course.
Nish: What is your greatest extravagance?
Dan: Lego collecting. First started off buying Star Wars lego sets like the Tie Fighter and X-Wing. Now I’m buying everything from Monkie Kid to Hidden Side sets!
Paul: Only buying one-way tickets.
Nish: You have exclusive dinner reservations for 4, excluding family and close friends, who are the 3 people (alive, dead, or imaginary) you’d invite?
Dan: David Bowie, Howard Hughes, George Lucas.
Paul: Ben Franklin, Genghis Khan, Florian Schneider (Kraftwerk)
Nish: What is the theme song of your professional life?
Dan: Balance by Future Islands. Results in my line of work take years to see if they play out. You definitely need to have an even keel attitude and as the lyrics in the song say, “It just takes time.”
Paul: Around the World. Not only is this a song from one of my all-time favorite groups, but it also describes my global footprint.
Nish: What is your motto?
Dan: Always Be Moving.
Paul: Say Yes, or All I want to do is have cool stories to tell my grandchildren.
Nish: What is something you’re really excited about right now?
Dan: I’m excited about a new restaurant opening up minutes from my home. It’s called Automat.
Paul: Still enjoying the summer.