The Brad Feld interview: Meaning, mentorship, and giving first
- Entrepreneur Brad Feld is a tech industry outlier who has spent a career quietly rejecting the orthodoxies that define much of Silicon Valley.
- Feld is a systems thinker and a long-term optimist who treats business as a kind of philosophical practice.
- Here, among other fascinating digressions, he considers randomness and how to move away from transactional thinking.
For as long as I’ve followed Brad Feld’s work, he’s felt like an outlier — quietly rejecting the orthodoxies that define much of Silicon Valley.
While much of that industry runs on short-term thinking and ego, Feld — based in Colorado — offers a quieter kind of wisdom. He’s a systems thinker, a long-term optimist, and one of the rare people in the industry who treats business as a kind of philosophical practice. In our conversation, we talked about Techstars, sure. But we also digressed into Buddhism, quantum randomness, and what happens when the world spins too fast to feel.
His latest book, Give First: The Power of Mentorship, is technically framed around startup ecosystems, but it’s really about something deeper: how we live, how we lead, and how we show up for others over time. It’s a meditation on complexity and the kind of necessary relationships that don’t appear in a financial spreadsheet.
As I work on my own book about long-lasting companies and enduring systems, I keep returning to mentorship as a vanishing craft. The best systems endure when there’s a foundation of teaching. Feld understands this. His “Give First” philosophy is one I admire deeply, and I wanted to ask him directly: how does he think about apprenticeship, networks, and staying grounded in a world that moves fast (and forgets easily)?
What follows is a conversation about those ideas — and a glimpse into how one of the more thoughtful minds in venture capital sees the long game.
Eric Markowitz: One theme that keeps emerging in my research is apprenticeship. In Japan, the oldest business, Kongō Gumi, has a construction apprenticeship model where craftsmen don’t actually start building until after 15 years of training. This echoes throughout long-lived companies. Why is this theme of mentorship so important to you?
Brad Feld: This isn’t something I just came to recently — it’s been essential to my business arc over the last 40 years. When I was a teenager, I had technology mentors who spent time with me when there was no reason for them to. What I experienced early on was someone being willing to invest time without knowing where it would lead, helping me learn quickly from their experience while also engaging in a way where they could learn from me. It wasn’t hierarchical or obligatory — it was mutually rewarding.
This really crystallized with what I call “the moment” with Len Fassler, who bought my first company. About eight years later, we were co-chairing a public company that was literally falling apart during the internet bubble. I was exhausted, sitting at his house before another terrible day. He looked at me and said, “Suit up — they can’t kill ya, and they can’t eat ya.” That moment changed how I thought about everything. He didn’t have to be there, but he was, side by side with me.
Eric Markowitz: You’ve written about the concept of “give first.” How did that philosophy evolve?
Brad Feld: It emerged from my work on startup communities after the 2008 financial crisis. I believed entrepreneurship could exist anywhere, not just in Silicon Valley. When I wrote Startup Communities in 2012, I put underneath it this idea that you had to give before you get to really move any system forward.
You have to be willing to put energy into a system without knowing what you’re going to get back — though it’s not altruistic. You expect something back; you just don’t know when, from whom, over what time period, or in what form.
Give first is a philosophy, not a religion. In religion, you follow rules to achieve salvation. A philosophy is ideas and theories about how things work, and you pick and choose what to incorporate into your own worldview. I’m essentially an existentialist — I believe we create our own meaning in an ultimately irrational universe.
Eric Markowitz: I’ve noticed a shift in my own thinking from transactional relationships to what you might call network-based thinking. Instead of competing for investors, I help other fund managers connect with potential investors. How do you see this playing out in today’s business culture?
Brad Feld: You’ve hit on something crucial. I think several factors drove us toward transactional interactions. First, the internet eliminated communication friction — suddenly everyone could interact trivially. Second, “networking” became about collecting followers and likes rather than meaningful relationships. Then came the horrific concept of “personal branding,” where people extract wealth through their brand without serving their followers meaningfully.
If you combine being present with openness to randomness — to things that aren’t planned or told to you are good — magical things happen.
When you get into a system where the feedback loop rapidly accelerates transactional dynamics around power and money, you follow that feedback. We’re now spinning in that loop faster than ever, and it’s disconnected people — especially the next generation — from what they actually want to do with their time.
Eric Markowitz: What caused this shift toward short-term, transactional thinking?
Brad Feld: It’s not a single thing, but I can point to key areas. Pre-1995 versus post-internet commercial availability created a massive shift. Social media turned interactions into transactional signals. The emphasis on “creating your personal brand” commodified relationships. And we’ve taken the governor off distinguishing opinion from fact, with enormous money behind promoting anything regardless of its validity.
If everybody took a longer arc — 30, 40 years, or thought multi-generationally — the dynamics would be completely different. When people ask about my legacy, I say I don’t care. What I do now matters, not what people remember me for 300 years from now, which they won’t anyway.
Eric Markowitz: You mention being present and open to randomness. Can you give an example?
Brad Feld: Techstars literally started because of something I called Random Day — a full day of 15-minute meetings with whoever wanted to meet with me, which I did eight times a year for about a decade. David Cohen took three months to get on my calendar. He slides a one-page brochure across the table about this idea called Techstars. I read it and said, “I’m in.” I walked out, called Jared Polis [now Governor of Colorado], and said, “Hey, I’m putting money into this thing called Techstars. Want to do it with me?” He said, “I’m in. What is it?”
Eighteen years later, Techstars has funded over 4,000 companies worldwide. You can’t get more random than that.
Eric Markowitz: There’s this obsession with growth in business culture. How do you reconcile venture capital’s growth imperative with sustainability?
Brad Feld: I don’t think you can control complex adaptive systems from a top-down perspective. What happens regularly is both micro and macro collapses — lots of little failures like parts of a forest burning down, allowing the system to grow back stronger. I learned this lesson with Techstars when we brought in a CEO to scale us bigger, which was exactly the wrong thing to do. More wasn’t generating better companies or outcomes.
We recommitted to the principle that “better is better” — the only reason Techstars exists is to help founders succeed. One longtime mentor would say, “Brad, better is better. Cut it with this more, more.”
Eric Markowitz: You talk about living in the present. How does this apply to business and investment decisions?
Brad Feld: Our ability to live in the moment and be fully present is extremely hard because of all the stimuli around us. But if you combine being present with openness to randomness — to things that aren’t planned or told to you are good — magical things happen.
Take a longer view. Be present. Give first without expecting immediate returns.
We’re conditioned to think in very short, transactional ways. But most of the truly important things that create value are serendipitous and unmodeled. Like your story about meeting your wife, or my Random Day that created Techstars. The key is being present enough to recognize and act on those moments.
Eric Markowitz: After my health crisis, I experienced profound presence — feeling more alive than ever the night before brain surgery. How do we cultivate that without crisis?
Brad Feld: That’s beautiful and exactly what I’m talking about. In Jewish tradition, there’s the concept of tikkun olam — repairing a broken world. I devote a section of my book to “Entrepreneurial Tzedakah,” because tzedakah doesn’t mean charity — it means righteousness. Maimonides‘ highest level of giving is essentially angel investing: giving someone money to help them become self-sufficient.
The most meaningful relationships in my life are peer relationships, not hierarchical ones. Even this conversation exemplifies that — it’s been a back-and-forth where we’re both learning, rather than a one-sided interview. That’s what great mentorship looks like: when both parties learn from each other.
Eric Markowitz: What’s your advice for people wanting to move away from transactional thinking?
Brad Feld: Start by focusing on what you can control — how you behave, how you engage with others. Ask yourself: Are you trying to be the person with the most success, or are you trying to contribute meaningfully to the things you’re involved in? I’d rather have a wonderful hour of conversation that nobody ever sees than optimize for some external metric of success.
Take a longer view. Be present. Give first without expecting immediate returns. And remember — there’s no winning in the end anyway. We’re all going to be gone. So what kind of experience do you want to have while you’re here?
