Brad Feld

Month: October 2022

I made my move at mile 22.

I’d been trailing my nemesis for a dozen miles. The half-mile cutoff was 2:50, and I rolled through at 2:43, so I had plenty of room to spare, although, by this point, I’d given up on my goal of 5:30.

My nemesis was wearing a red shirt. I could see them a quarter to a half-mile ahead of me for several hours. I’d get a little closer, and then they’d pull away.

At mile 14.5, a timing device was set up, presumably to ensure the marathoners were on the second loop. I noticed the guy monitoring it (who later I learned was named Nate) picking up the cones after I went through.

I asked, “Am I in last place?”

“Yes”

“That’s a new experience for me. I guess I have a goal besides finishing.”

“What’s that?”

“Not coming in last.”

I knew I had several hours to catch the person in the red shirt. There was no rush. I took it easy and just cruised through miles 14 to 22. My new friend Nate the Great was at each water stop, packing things into his U-Haul after I passed. Since Red Shirt wasn’t really pulling away much, I’d stop, fill up my water bottle, and chat with Nate.

At mile 22, I picked up the pace. The last three miles of the course were on the Rail Trail. The nice people in New Hampshire considerately paint all the rocks and tree roots on the trail white, so it was a particularly delightful place to pass Red Shirt. As I went by, Red Shirt kind of groaned, and I said, “You got this,” which seemed to be the mantra for this race.

Nate was waiting for me at mile 23, ensuring I was still on the trail.

He said, “Looks like you did it.”

“Yup. Second to last place is more fun than last, but I’ve still got a few miles to go.”

“You got this.”

Yup. I sure did. New Hampshire is State #26 on my quest to run a marathon in every state. I haven’t done many in the past few years, and I’m getting slower as I get older. But I know how to get 26.2 miles done, no matter what the pace (I haven’t had a single DNF in all my efforts.)

The small marathons are my favorites. Other than looking at Red Shirt’s back for a long time, I was alone for most of the marathon, which is one of my favorite ways to exist on your planet.


Since Matt Levine is so effectively covering anything interesting in the world of the Twitter deal (and all kinds of bizarre, random, and complicated crypto, fraud, debt, and other financial stuff), I think I’ll stick with book reviews for the time being.

Andy Dunn, who I only know indirectly, wrote an important book titled Burn Rate: Launching a Startup and Losing My Mind. While it covers the story of Andy’s company, Bonobos, it’s really about mental health and entrepreneurship.

While there might be other entrepreneur autobiographies like Burn Rate, I can’t think of any. The closest is Tracy Kidder’s awesome book titled A Truck Full of Money about Paul English, an entrepreneur I do happen to know.

Tracy’s book is a mix of Paul’s entrepreneurial story combined with his experience being bipolar. Andy’s book is his entrepreneurial story combined with his experience of being bipolar. Both are remarkably brave books. Andy’s autobiography is particularly powerful since he is extremely detailed about several of the manic experiences that he had while running Bonobos.

While I don’t know Andy, I know several of his investors. His description of how they handled the situation of discovering Andy’s mental health diagnosis made me proud to know them. Andy decided to proactively hold a board meeting to describe what had happened that resulted in him ending up in the hospital and jail. One of his board members, Joel Peterson (who I don’t know), is remarkable.

“When I got out of the hospital, I walked straight into handcuffs. The City of New York charged me with misdemeanor assault and felony assault of a senior citizen.”

“Has there been a diagnosis?” Joel Peterson asked.

“The diagnosis is bipolar disorder type I. I was originally diagnosed when I was twenty, and I’ve been in denial about it for sixteen years.” A brief silence.

“I know a few folks who have dealt with what you’re dealing with, Andy,” Joel said calmly, holding true to his role as my professional father figure, “including more than a couple of entrepreneurs. It’s entirely manageable. I have full faith in you to take care of yourself, and I have full confidence in you as our CEO.”

Andy covers the rest of the board meeting discussion, including questions from board members about whether he was getting appropriate treatment, his legal situation, and the game plan for addressing any publicity around the situation.

A while ago, I was at a dinner with a bunch of VCs and entrepreneurs, including several very famous ones. One of the entrepreneurs stated clearly that if he ever talked openly about his struggle with depression, his board would immediately fire him. Fortunately, this was not the response of Andy’s board, as they took in the situation, asked questions about it, and made rational and deliberate decisions about what to do going forward. It’s worth noting that Andy was still the CEO of Bonobos when Walmart acquired it several years later.

I’m hopeful that Andy’s book will continue to help destigmatize mental health in entrepreneurship. Thanks, Andy, for being willing to write such an intimate story about your experience.


Steve Case’s new book, The Rise of the Rest: How Entrepreneurs in Surprising Places are Building the New American Dream, is out. I read it on Sunday, and it is outstanding. If you are interested in understanding how high-tech entrepreneurship has evolved from a primarily coastal phenomenon to one that covers the entire US in the past decade, grab this book now.

Steve is a great storyteller. While he tells the entrepreneurs’ stories, he has been part of helping create them. He created Rise of Rest and did the first of many bus tours in 2014. I was part of the one in Denver, and my partner Chris Moody was part of the one in Birmingham. They were each awesome experiences.

This is the story of what happened on those bus tours, people who were connected, companies that were amplified, financings that happened, and cities that were energized around entrepreneurship.

For the past dozen years, I’ve spent plenty of energy on democratizing entrepreneurship. I’ve worked with Steve and his team on multiple initiatives, including Startup America and Up Global. Steve’s supported me on several things I’ve done, including writing the foreword to Startup Communities: Building an Entrepreneurial Ecosystem in Your City.

When I was a young entrepreneur in my 20s, Steve was a hero of mine. My AOL username was bfeld, which was where my Twitter handle (and everything else I signed up for on the web came from.) Now that I’m a middle-aged something or other at 56, Steve’s still a hero of mine. I expect this is true for many other entrepreneurs.