Brad Feld: The detour
The investor, tech leader, and writer talks about legacy, leadership, and learning to live with emotional honesty.
Brad Feld is a longtime venture capitalist, entrepreneur, and author. A founding partner at Foundry Group and co-founder of Techstars, he has played a pivotal role in shaping startup ecosystems across the U.S. Learn more about his perspectives:
Ritika: Brad, thank you so much for taking the time to talk with me and for everybody who's going to be reading, whether they be new entrepreneurs, whether they be career changers, people really looking to find their own path, the path that you've taken in life from using your intellect as your gift to becoming such a force in the venture capital world to empower generation upon generation of founders.
I can't thank you enough for that, and I can't thank you enough for all of the good that you are doing to for the global commercial ecosystem.
It's really wonderful to be talking with you today.
I'd actually love to go back to the days before all of this materialized.
Before you became such a notable venture capitalist, did you ever see this path for yourself, perhaps when you were younger or before you ended up at MIT?
What were you like as a child, as a teenager, and when did things start to become clearer for you as to what your purpose on this planet would become?
Brad: I don't know that I ever had a deliberate plan at any stage along the way.
Even when I sort of reflect about where I am today, I'm not sure that I have total clarity on my forward looking plan.
I don't think I ever do.
I'm sort of constantly allowing the things that I do and the people that I know and the stuff that I'm involved in and places that I'm curious sort of take me wherever they take me.
As a kid, I grew up in Dallas, Texas.
I was really fortunate. I had two loving parents of a younger brother that I'm very close to. My dad's a doctor, my mom's an artist.
It was definitely a privileged American upper middle class upbringing.
My parents had value systems around education and the importance of learning. These cultural norms were very deep.
From a very young age, I was always a very curious learner on a wide spectrum.
My parents held us to standards.
They gave both my younger brother and I lots of space to explore what was interesting to us.
A very memorable example I have…my dad was a doctor. I'd heard the stories from his father about how important it was for my dad, who was the oldest, to be a doctor…just in terms of my grandfather's view of what my father should do.
I hated everything about what my dad did as a doctor.
He would take me on rounds with him to the hospital.
I hated the smells.
But I loved to read.
I'd always curl up in the corner somewhere with a book, oftentimes under a desk to try to hide out of wherever the activity was.
When I was about 10 years, I remember very vividly walking into my dad's office.
He had study at a little office at our house.
At the end of the day, after we'd had dinner together as a family, he'd go into his office. He'd call patients and do the manual part of the charts that you would do as a doctor and sort of catch up on everything.
I was very nervous.
I sat down with him and he could tell I was nervous.
He says, “Brad, what's up?”
I just sort of blurted it out like a little kid blurred something out when they're nervous.
“Dad, I don't want to be a doctor.”
He looked at me and he sort of paused for a second and he said, “Brad, when I was your age, my dad said that I could do anything I wanted to do.”
“Brad, you can do anything you want to do.”
He set me free.
Ritika: What were some of the things that you began to explore after you felt that freedom?
Brad: Winding the clock forward as a teenager…the personal computer came out.
I bought a very early Apple II computer.
I was into computers. I played a lot of tennis. I liked running.
Something I learned about myself is that I love to be alone, and I love to be outside, whether that means going for a long hike or contemplating what’s going on.
I was a typical high school nerd. I was very into math and science. I also have always been and will always be a voracious reader of lots of different kinds of things. I read a huge amount of fiction…and also a lot of biography.
What I’m more interested in is stuff that challenges me intellectually. Science writing, ideas that are unfamiliar or hard to wrap my head around, new concepts that require me to think differently. That’s where I get a lot of energy.
Back in high school, that curiosity kind of set the tone for everything. I went to MIT, but even before that, during my junior year, I really wanted to spend a summer in Europe. So my parents helped me land a job with this little computer company in London. The company was called Tronix, and I spent the summer living with this older couple—a World War II vet and his wife. I was 16, living in London, getting to work and explore and just have that experience. It was incredibly formative.
Then in my senior year, I got a job working for a husband-and-wife team who had started a company in the oil and gas industry. They were writing software for that space, and I came in as a developer. I made $10 an hour, which at the time felt like a ton. And I learned really fast: if I worked 80 hours a week instead of 40, I made twice as much. They didn’t give me equity, but they gave me 5% royalties on all the software I wrote.
So as a freshman in college, I was getting these checks. Sometimes it was $1,000 a month, sometimes $2,000. One month, I got a check for more than $10,000 for something I’d written that they were still selling. It was kind of wild.
That early overlap—between business and entrepreneurship and software—was really powerful. But again, I wasn’t doing it because I had some master plan. I wasn’t trying to “be” something. It was driven by curiosity more than anything else.
Ritika: And at some point, as we’re jumping through time in this conversation, something started to really catalyze for you.
You’d been pursuing these curiosities, exploring these different avenues to find what you loved.
And all of a sudden now you are running multiple VC firms, including Techstars, which is one of the most notable platforms to empower entrepreneurs in the world.
How did this happen?
Brad: Well, first—an important point—I don’t run Techstars. That’s very deliberate. There are two co-CEOs, David Cohen and David Brown. They’re two of the four co-founders. I’m one of the other co-founders. I’m still on the board, I’m involved in strategy, I’m an investor, but I don’t run anything anymore.
And that’s true across the board. I was a CEO once. I started a company in my early twenties, and I ran it for seven years. We were self-funded, had to be profitable—there was no safety net. And we pulled it off. We sold it to a public company. After that, I stuck around for a couple years and got exposed to a whole different world—acquisitions, integration, being part of a much larger business.
That’s when I started doing angel investing, mid-’90s. Writing checks with my own money. Helping start companies. Even as late as 2000–2001, I still had one foot in operating. I was co-chairman of a couple companies, very involved. And then the internet bubble burst.
My world kind of collapsed. It was a mess. That’s when I made a conscious decision to stop operating. I didn’t want to run companies anymore. I wanted to focus entirely on the investor side—but not just writing checks and walking away. I wanted to be involved. Just not in charge.
And that’s where the shift happened. I reframed how I work with founders. Since around 2002, my personal mantra has been: as long as I support the CEO, I work for her. If I don’t support her anymore, it’s on me to either find a way to get back to a place where I do—or help the company make a change.
That mindset has shaped everything. I’m there to help. I’m not there to run things. And that’s been true with Techstars. It’s been true with Foundry Group. Nobody’s the boss. It works because we respect each other and we stay aligned on values.
Ritika: And to that point, I remember reading an article that you wrote a couple years ago, Falling Out of Love with Being CEO.
It struck me deeply. I grew up in Silicon Valley, where the CEO is often seen as the ultimate point of success.
I’ve seen that over and over again—especially in the early stages—this pressure to perform can really mess with someone’s sense of self.
I’m curious… what kind of introspection helped you see leadership differently?
And how did you start to separate yourself from that traditional CEO narrative?
Brad: Yeah… there’s a lot packed into that. The definition of success is always interesting to unpack. There’s the external version—money, power, recognition—but I think when you get to the end of your life, when you’re looking back on everything, none of that really holds up.
But that insight didn’t just show up one day. There were a few moments in my life where I had to really face it. One of the first was right after we sold my first company. I was still in my twenties. I’d been CEO for seven years. And I just… didn’t pay much attention to how I felt about it while I was in it. I was doing the job. I wasn’t really evaluating it.
Around the same time, I went through a divorce—my high school girlfriend and I got married young, and it didn’t last. And I also got kicked out of a PhD program. I wasn’t doing the work. I deserved to get kicked out. I was running a company and just didn’t care about the academic stuff anymore.
So all of that hit at once. Business success. Personal failure. A lot of identity stuff. And I dropped into a deep depression. It lasted a couple years. And I didn’t have language for it back then—I didn’t call it depression—but it was.
That was the first time I really had to reflect. Like: what am I doing? Who am I doing it for? What actually matters to me?
Then again in 2001–2002, when the internet bubble burst, my world just collapsed again. It was brutal. I had another depressive episode after 9/11. It lasted a few months. And that’s when I had this realization: I liked being involved with companies. But I didn’t like running them. I didn’t like being CEO. I was good at it. But it didn’t bring me any joy.
So that’s when I made the shift. Not because I had it all figured out—but because I started paying attention to what felt true for me. That’s really been the throughline ever since.
Ritika: You mentioned you’ve had multiple depressive episodes throughout your life.
One that really stuck with me was the one you wrote about in 2013—where from the outside, everything looked great, but internally, you were unraveling.
Can you walk us through that time in your life?
Brad: Yeah. That one was kind of sneaky. Because if you had looked at everything on the outside—on paper—things were awesome.
Amy and I were great. We were living in Colorado, which we both love. Foundry Group was doing well—my partners and I had a super close relationship, our funds were performing. Techstars was growing like crazy. I was in good shape physically. I had two golden retrievers. Like, everything you’d use to check the boxes was there.
But I had just worn myself out in 2012.
It started with an ultra-marathon in the spring. A 50-mile run. It took a huge amount of training to get ready for it. And I did it, which was great—but then two days later, I was on the West Coast working again. No recovery.
And then I just kept going. Traveled constantly that year. Didn’t slow down at all. In the summer, I went on this bike trip in Slovenia with my partner Seth and a few friends for his 40th birthday. On the second-to-last day, I had a near-fatal bike crash. Hit someone, bounced off them, landed wrong—if I’d gone over the guardrail, I probably would’ve died. Matter of inches.
I was pretty banged up, but I didn’t take the time to recover. I went straight to New York with Amy, and we spent the next month there celebrating her birthday. September is Amy’s birthday month, and we go all out for it. So we’re out every night, I’m still working during the day, and I just kept pushing through.
Then in October, I ran a marathon I had no business running. I hadn’t been training properly since the crash, but I did it anyway, mostly to support my partner Jason who was running his first. And I finished it, but… again, no rest.
In December, I got a kidney stone. Needed surgery. Went through that, and I remember thinking: okay. 2013, clean slate. Let’s go.
I flew to CES in January. Got there, walked into the hotel… and within two hours, I was lying in my room with a pillow over my head and the shades drawn. I couldn’t deal with people. Couldn’t deal with noise. And I thought: something’s really wrong.
That’s when the depression hit.
Ritika: So what did you do after that? When you realized it wasn’t just exhaustion—that you were really depressed?
Brad: The first thing I did was just acknowledge it. To myself. That’s step one. If you’re struggling with your mental health—whether it’s depression, anxiety, mania, whatever—you’ve got to be able to say, “Okay, this is real. I’m in it.”
That doesn’t solve anything. But it gives you a place to start.
So I started making changes. Tactical things. Not big philosophical shifts, just daily stuff. I stopped drinking. Cut out caffeine. No more coffee. I made sure to go outside every day—at least an hour—to walk or run.
I canceled a bunch of travel. Looked at my social commitments and just said no to the stuff I knew I wouldn’t enjoy. Not everything. But enough to give myself space.
I also stopped waking up with an alarm clock. That was a big one. For almost 20 years, I was that guy who got up at 5am no matter what time zone I was in. It was like part of my identity. But I let it go. I told people: I’m not starting my day until noon.
And I slept. A lot. Like 12 hours a night. For months. My body just needed it.
I also told the people close to me what was going on. Amy, obviously. My partners at Foundry. A few other friends. I wrote about it on my blog, too—by then I was comfortable being open about it publicly.
One of the best things that happened was my old business partner, Dave. He’s known me forever—probably better than anyone besides Amy. He didn’t ask, “How can I help?” He didn’t make me explain anything. He just showed up.
He’d check in with my assistant, find a time when I had a free hour, and then he’d come by and say, “Let’s go for a walk.” And we’d walk. Sometimes we didn’t say a word. Sometimes we talked the whole time. But he knew…it was about showing up, not fixing anything.
Ritika: You’ve been on both sides of this—going through it yourself, and supporting other people who are struggling.
What’s something you’ve learned about how to actually show up for someone who’s in a dark place?
Brad: Yeah… I think the biggest mistake people make is thinking they can fix it.
Like, you see someone struggling and your instinct is to say, “Hey, how can I help?” And that seems nice, but honestly—when you’re in it, when just getting out of bed feels like a win—that question is overwhelming. It gives the person another thing they have to figure out. “Now I have to come up with an answer that makes you feel better about what I’m going through.”
So one of the best things you can do is just be there. Don’t try to solve anything. Just show up. Sit next to them. Go for a walk. Be quiet if you need to. If you know them well, do something you already know helps—without asking for permission.
And if it’s serious—if you think they might be in real danger—don’t try to be their therapist. Encourage them to talk to a professional. Get help that’s appropriate for what they’re going through.
But yeah, a lot of it is just about being available. Being empathetic. Not judging. Not cheerleading either. “Come on, the sun is out! You’ll feel better soon!”—that stuff doesn’t help. It might actually make someone feel worse.
Instead, it’s about timing. Being steady. So that when they do finally peek their head up, when they reach out—even a little—you’re already there.
Portrait illustration by Kat Cao