Through my husband, Bradley and I have been friends for several years -- plus we also had the chance to work together briefly on an issue related to organ donation. Bradley has an unusual combination of qualities: he's highly thoughtful and contemplative, highly effective, and extremely comfortable with conflict.
He's had a very colorful career. Among other roles, he was Deputy Governor of Illinois, campaign manager for New York City Mayor Michael Bloomberg, worked with startups like Uber and Lemonade, and is the founder and CEO of Tusk Holdings, a multi-faceted platform that includes multiple businesses. I knew some of the highlights of his history, but I was excited to learn more of the details by getting my hands on my copy of his new book The Fixer: My Adventures Saving Startups from Death by Politics.
Because he's thought so much about happiness, habits, and productivity, I couldn't wait to interview Bradley on these subjects.
Gretchen: What’s a simple activity or habit that consistently makes you happier, healthier, more productive, or more creative?
Bradley: I never end a workday without having finished the day’s to-do list, made the next day’s list and returned or at least dealt with every incoming call, text and email. It’s not like things automatically stop happening once I do those things but it makes it a lot easier to enjoy the evening.
Gretchen: What’s something you know now about happiness that you didn’t know when you were 18 years old?
Bradley: That the cliché about “it’s the journey, not the process” ended up being right. I spent way too long chasing specific achievements and then wondering why I wasn’t happier when each one happened. I still have a pretty ambitious list of goals but I now get that the work we do to achieve them is far more interesting, fulfilling and important than that one moment at the end when you check the box. Writing my book – The Fixer: My Adventures Saving Startups From Death By Politics – also helped me figure this out since it forced me to look back at my life and career and lay out how things happened.
Gretchen: You’ve had fascinating experiences. What experience surprised or intrigued you – or your readers – most?
Bradley: That nothing comes easy – and that there’s no secret book of knowledge or answers. Everyone’s mainly making it up as they go along and doing their best. The people who put the most into it, take the most risk, are willing to have the biggest ideas, and are willing to be held accountable tend to be the people who succeed. That was true even when I worked for Mike Bloomberg as his campaign manager. Mike’s a genius but it wasn’t like he inherently just knew everything. He put the work in. Every single day.
Gretchen: Have you ever managed to gain a challenging healthy habit – or to break an unhealthy habit? If so, how did you do it?
Bradley: My kids – like all kids – never got ready for school when they were supposed to. I’d ask nicely half a dozen times and then start yelling. That never actually moved anything along, it just made everyone really upset. I realized what I was doing, spent a lot of time thinking about it, a lot of time working on it in therapy, a lot of time reminding myself and eventually, I stopped doing it altogether. They’re still usually late for school.
Bradley: According to this, a Rebel, which is a relief since I work in technology and am supposed to disrupt things.
Gretchen: Does anything tend to interfere with your ability to keep your healthy habits or your happiness? (e.g. travel, parties, email)
Bradley: Boredom is the biggest problem. If I’m really busy and focused on whatever I’m trying to do, I’m usually good. But if I’m bored, that’s when I start causing the kind of trouble that’s counter-productive (although sometimes fun). The other is obsession. I get so focused on whatever I’m doing that I’ll wake up at 3am every morning just to check my email. That’s not healthy – whatever’s on there will still be there at 5am.
Gretchen: Have you ever been hit by a lightning bolt, where you made a major change very suddenly, as a consequence of reading a book, a conversation with a friend, a milestone birthday, a health scare, etc.?
Bradley: I spent four years as Deputy Governor of Illinois. My boss was the now incarcerated, frequently insane Rod Blagojevich. About halfway through, I couldn’t take it anymore. I flew home to New York for a week with every intention of never going back. My friend Rob Galligan and I spent around three hours walking through Central Park, talking about why I hated Rod so much. And by the time we were done, I realized the job wasn’t about Rod. He was just an impediment. The job was about the ways we could help people and do things differently and what I could learn from it. Not shockingly, Rob went on to become a very successful therapist.
Gretchen: Is there a particular motto or saying that you’ve found very helpful? (e.g., I remind myself to “Be Gretchen.”) Or a quotation that has struck you as particularly insightful?
Bradley: There’s a sign on the wall of my kids’ school that says “Character is what you do when no one is watching.” Whether it’s going home to get more bags and then back outside to pick up our dog’s poop off the street or making the extra effort to recycle or tipping every Uber driver even though the trip is over, you’re out of the car and will never see them again, I think about that sign — and do things I don’t really feel like doing — all the time.
Gretchen: Has a book ever changed your life – if so, which one and why?
Bradley: When I was in elementary school, I read a novel about politics called Advise and Consent by Alan Drury. The minute I finished the book, I knew I wanted to work in politics. Most of real life in politics wasn’t as exciting as the book but enough of it was that I’m grateful to the librarian who handed it to me.
Gretchen: In your field, is there a common misperception or incorrect assumption that you’d like to correct?
Bradley: As a venture capitalist, people outside the field tend to focus on the capitalist part and assume the point of the job is to just make as much money as possible. That’s obviously part of it, but every good VC I know cares far more about building new companies, launching new ideas and disrupting the status quo than just making a good return. You don’t become a VC to get rich. You become a VC because you like blowing things up.
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