From Techstars to AI trends: Brad Feld on building enduring legacies

by Alpha Partners Editorial

What do enduring legacies in venture capital look like? 

Brad Feld, a true icon of the startup world, has spent decades building not just companies but also communities, systems, and generations of investors. His fingerprints are on some of the most influential platforms in tech, including Techstars and Foundry Group.

In this episode of Driving Alpha, host Steve Brotman sits down with Brad for a candid conversation spanning four decades of venture capital. From his early days founding Feld Technologies to scaling Foundry and supporting fund managers as an LP, Brad unpacks the lessons he’s learned and how he’s applying them in his final “third third” of life. Topics include mentorship, venture cycles, AI tools, and how to stay relevant without clinging to power.

Brad Feld brings unmatched credibility to the table. As co-founder of Techstars and a prolific investor in companies like Zynga, Fitbit, and MakerBot, his advice is both deeply informed and refreshingly honest. Whether you’re a founder, VC, or operator, this episode is packed with actionable insights from one of tech’s most trusted minds.

Want more of Brad’s wisdom? Grab his latest book: Give First: The Power of Mentorship,  a must-read for founders, fund managers, and anyone shaping the future of innovation.

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Steve Brotman: Hi, I am Steve Brotman, Managing Partner at Alpha Partners. Welcome to Driving Alpha, where we uncover the visionaries and values that shape the future of venture capital. Today, we’re joined by Brad Feld, Partner and Co-Founder at Foundry Group, and a figure whose impact on early-stage venture investing and tech entrepreneurship spans nearly four decades.

Not only a builder and investor, Brad is a prolific author and thought leader. His books—including Venture Deals and Startup Communities, and his long-running blog Feld Thoughts—have equipped countless entrepreneurs and VCs with tools and frameworks to succeed. He actually just published his latest book, Give First: The Power of Mentorship. I encourage all listeners to pick up a copy—we’ll chat more about what’s in the book in a bit.

Brad’s journey is anchored in academic rigor and entrepreneurial spirit. After earning both his Bachelor’s and Master’s at MIT, he launched Feld Technologies while still a student. That startup was acquired by AmeriData and fueled Brad’s early career as a serial founder, angel investor, and executive. Brad quickly scaled his influence in venture capital, co-founding Mobius Venture Capital, and ultimately Foundry Group in 2007.

At Foundry, Brad helped grow a portfolio that’s defined by multiple tech areas. One of his best-known legacies is the creation of Techstars, one of the world’s top accelerators. Brad was an early investor in transformative companies like Harmonix, Zynga, MakerBot, Fitbit, and Rover, among many others. His investments and mentorship have directly contributed to startups raising billions and pushing the boundaries of what’s possible in consumer tech, health, SaaS, and hardware.

Get ready for an in-depth conversation with Brad Feld, a true architect of modern venture capital—on building enduring communities, investing through market cycles, and what it really means to drive alpha in tech and beyond. Welcome, Brad.

Brad Feld: Steve, thanks for the lovely intro and congrats on everything you’ve done with Alpha Partners. It’s been pretty awesome, and I’m delighted to be here on the Alpha podcast.

Steve Brotman: Thank you, Brad. It’s an honor for us to have you and we’re flattered that you’re taking some time this afternoon to chat at a pretty interesting time in the venture universe.

I didn’t realize you’re operating on your fourth decade. That must be quite a feeling. Do you feel like you’ve gotten to the top of the mountain? Are you at the bottom of the mountain and looking up at another mountain?

Brad Feld: Well, I turned 60 on December 1st, so I’m definitely feeling old and increasingly irrelevant, which is kind of a fun feeling. I’ve been contemplating the length of time that I’ve been doing this for a while. One of the things that occurred to me maybe about five years ago was how I spend the last third of my life—whatever that’s going to be—and what it means compared to the prior two-thirds.

My wife, Amy Batchelor, and I really talk about this notion of “third thirds.” The first third: you’re growing, developing, forming your views and values, having early experiences. The second third: you’re deep in work, career, maybe building a family—though in our case, we didn’t have kids—so it was more about building a relationship and a life together.

Then comes the third third. For many people, I think it’s characterized by holding on by your fingernails to power and relevance. We see it especially today in politics—in Washington, D.C.—with people at the very end of their lives still trying to shape and form how society works.

I don’t feel that way about myself. That’s not my role for the last third of my life. I’m fascinated by wisdom traditions, like Buddhism. In Buddhism, there’s even this quarters model where the last quarter is becoming an ascetic and wandering into the woods, disappearing. I don’t think I’ll do that—but the way I think about the rest of my journey, whether I live one day or 30 more years, is very different from the arc I’ve been on these last 30 years. Still figuring that out as I wander into being 60.

Steve Brotman: Fair enough. Some people have a third act.

Brad Feld: I definitely don’t have another act. I’m very clear on that. A venture fund takes a long time to wind down. Having been through the experience of the last fund we raised at Mobius—which lasted for 22 years—and being an LP in funds that are now 18, 19, 20 years old, I’m very clear: the fund we closed in 2023, which we announced in early 2024, will be Foundry’s last fund.

That fund has a long tail ahead, and I’ll be doing that work for quite some time. I’m comfortable with that. I like doing the work at this stage—it’s not about launching yet another fund or a new wave of early-stage companies with long arcs. We have about 80 active companies and about 50 fund investments across all our funds—so we’re in this large-scale support phase, helping those companies navigate whatever comes next.

I’ve also personally been investing in venture funds since 1997, starting with Highland Capital Partners Fund III. We’ve backed a lot of first-time and spin-out funds and new GPs. It’s been a real joy—not just supporting founders and leaders of companies, but also supporting new fund managers as an LP. Whether or not I’m on the LPAC, whether or not we’re a major LP, just being a mentor in that context—whether people listen or not—and sharing our experiences in firm building, that’s really satisfying.

Steve Brotman: Interesting—sort of a meta VC role. Are you going to continue doing that?

Brad Feld: Yeah. One of the things that gives me great joy in a work context—and this is part of why I wrote the book Give First: The Power of Mentorship—was to talk about my personal philosophy around how I engage, which is a “give first” philosophy. But also to discuss how effective mentorship works. I’ve learned a lot over the years, both through Techstars and through my own experiences, about what can be effective—and what’s not effective.

There’s an enormous amount of behavior in venture capital, in angel investing, and in entrepreneurship that’s labeled “mentorship,” but is actually not effective. But there are many techniques and approaches that are very effective. And that’s reflective—it works both ways. Whatever’s effective from a mentor perspective is also effective from a mentee perspective. It’s not a singular dynamic.

Back to what gives me joy: I love and get enormous pleasure from being helpful and additive to a founder. And I consider fund managers who’ve created their own firms to be founders as well, because a fund is a business. So when I’m able to be helpful—whether it’s clearly defined mentorship or just offering experience—it’s deeply satisfying.

One of the contrasts to the last 40 years is that when you’re investing in lots of new things, you don’t know yet which people you’re really going to enjoy working with. You don’t know yet whether the companies are going to succeed. But developing long-term relationships, and then being able to select which ones to invest energy into over time, is very satisfying.

Steve Brotman: In terms of mentorship—clearly, there are a lot of ways to approach it. A book today is super helpful, especially given the experience you’ve built over the years. Did you have mentors in venture specifically, or did you figure it out yourself? Mobius was pretty young. Could you share some of the mentors that impacted you?

Brad Feld: In venture, that arc is interesting. But I also had mentors before I entered venture.

One of the things I like so much about the construct of effective mentorship is that mentors often share stories. Those stories don’t have to be long—but they speak from experience to illustrate a point. It’s something I learned in my early twenties when I joined the Young Entrepreneurs Organization (now called Entrepreneurs Organization). EO Colorado, which I co-founded, is about to celebrate its 30th anniversary. It’s amazing to have done something that long ago and still be connected to it.

One of the core things I learned in EO was the value of storytelling to illustrate points. There’s a concept called “Forum”—not to be confused with the Forum from Werner Erhard or EST—but rather a structured approach to sharing experience through storytelling. That stuck with me.

One very early mentor was my uncle, Charlie Feld—my dad’s younger brother. He was incredibly impactful when I was learning about computers. I started programming at 12, and Charlie was the first one who really introduced me to that world.

Then there’s the magic trick of mentorship: becoming a peer. That transformation, from mentee to peer, can happen quickly or over a long period. With Charlie, it was gradual. But another mentor of mine, Len Fassler—who bought my first company—was someone with whom that peer transformation happened during the work itself…Len Fassler was partners with Jerry Poch, and they had two very successful venture funds—Pequot Capital, which later spun out and became FirstMark. I would consider Jerry a VC mentor—someone who, in the early days of my venture career, was figuring things out at the same time I was, even though he had already been the founder and co-chair of several public companies.

Len, on the other hand, was a mentor to me in the context of company-building. We ended up starting a couple more businesses together after they acquired my first company. I had a moment with him that taught me what true peer mentorship feels like. We were at a dinner—probably with 15 people—and I overheard him from across the table say, “I’m learning so much from Brad.” I turned to him and said, “What did you say?”

He repeated it, and I said, “That’s bullshit. You’re an unbelievable mentor—I’ve learned so much from you.” He said, “Well, I hope that’s true, but I am learning so much from working with you, being around you, seeing how you think.” He was 32 years older than me, but it was a real moment of mutual respect and growth. He passed away a few years ago, but Len was one of those critical early mentors in venture.

I mentioned Jerry Poch—he and the FirstMark team have built something incredibly successful. Jerry and I are still regularly in touch. Another person who played an enormous role for me was Ron Fisher.

Ron was Vice Chairman of SoftBank, and he was involved when we created SoftBank Technology Ventures, the fund that later became Mobius Venture Capital. That was in 1996. Ron was the SoftBank-side sponsor of the fund. He wasn’t a partner in the same way as the rest of us—he was the administrative partner from SoftBank’s perspective.

But he had special relationships with everyone—Ron is an amazing human being. I think because I was young, and maybe a bit more comfortable in some contexts, I ended up working closely with him. I listened very carefully to him. We worked on a number of deals together. And over time, I came to rely on him in moments when I was confused, disoriented, or when things weren’t going the way I thought they should.

During the internet bubble—when everything was accelerating to irrational heights—and later when it burst, I remember multiple times going back to Ron for grounding. SoftBank had also launched SoftBank Capital Partners, a separate fund, and our Mobius team rebranded because the two were getting confused.

Fast forward: Mobius decided not to raise another fund after our investment period ended in 2005. We had tried in 2004, but the tech markets were still struggling. The internet bubble had popped, and we couldn’t get traction with LPs.

We were managing three funds—SoftBank Technology Ventures IV, V, and VI—and Fund V was a disaster. It was a 1999 vintage, and one of the worst-performing funds I’ve ever seen (though I’ve seen worse). Fund IV was successful. Fund VI was in the middle—invested in 2000 into the teeth of the crash. Not much was mature, and lots of early write-offs.

So when we failed to raise Fund VII, a group of us—five partners—decided it didn’t make sense to keep Mobius going. I was the only original partner left. As part of winding it down, I made a commitment to VPs and to SoftBank—effectively Ron—that I would stay through the end of the fund’s life in 2022. I didn’t realize what that actually meant back then. But I did it.

I wouldn’t have made that kind of commitment unless it was to someone I so deeply respected. Ron was that kind of person—someone I’d do anything for.

Steve Brotman: Amazing. I was just thinking about all the people that I know who sort of effectively spun out of SoftBank. Is there a list?

Brad Feld: There’s probably a long list. It’s a fascinating dynamic, looking back on that time period. The SoftBank arc in the contemporary era was also fascinating—when the Vision Fund spun up.

For me, having lived a similar story in the ‘90s—with different dynamics, certainly in how tech investing worked—watching the Vision Fund from the outside felt very familiar. Masa Son started investing in the U.S. by acquiring digital media properties in 1995—Ziff Davis was one, where Eric Hippeau came from. Eric went on to form SoftBank Capital Partners with Ben Lerer, which became a really significant firm.

Masa also bought Comdex, the big trade show business. But of course, the famous moment was when he showed up and committed to buy 30% of Yahoo for $30 million pre-IPO. Everyone thought that was crazy at the time—a $100 million valuation for this company with an exclamation point in its name.

So for me, watching the Vision Fund was like watching the same story again—but with two more zeros at the end. Instead of a $1 billion fund, which back then was ludicrous, now it was a $100 billion fund. Just the scale had changed.

Steve Brotman: But it was ludicrous, right?

Brad Feld: Of course. History gets to write whatever story it wants. Masa is amazing—I don’t think he could pick me out of a lineup at this point. Maybe he could; we’ve met a few times. I’ve been in the room for some very interesting conversations, and I heard the “I’d like to buy 30% of your company” line enough times to recognize it as part of his schtick.

What was amazing about Masa—and a close friend of mine told me this story—is that every day, he woke up with a blank piece of paper. He didn’t carry over the wins or the losses from the day before. He thought fresh every day. That’s incredibly difficult.

If you think about sunk cost fallacy, or just the emotional ups and downs in this business, it’s hard. When things are going up, you’re either being celebrated or attacked. When things are going down, everyone criticizes you. But that’s life—that’s the hero’s journey. Joseph Campbell wrote extensively about it. There’s nothing new here—it just plays out over and over again.

But Masa is unique. He carries through it all with unwavering enthusiasm for what he’s doing. That’s really hard to do.

Steve Brotman: Well, the older, bearded mentor is pretty strong in that hero’s journey, right?

Brad Feld: Yeah, the hero’s journey includes the bearded mentor. I’m comfortable with that. I’m very much Star Wars, not Star Trek. Any science fiction fan knows—you have to be either Star Wars or Star Trek. You can’t be both. I’m firmly in the Star Wars camp.

When Mark Hamill disappeared and said, “I’m done, goodbye,” I sort of embraced that idea too.

Steve Brotman: So why Star Wars, not Star Trek?

Brad Feld: It’s a childhood thing. I must’ve been around 11 or 12. I remember seeing Star Wars with my dad. I walked out of the theater, my mind blown. I said, “Can we go see it again?” He said, “Not tonight.” But I went again the next day, and then again. I don’t normally rewatch movies, but I saw Star Wars multiple times.

At the same time, Star Trek was happening, but I didn’t watch much TV as a kid. My brother and I were only allowed one hour of TV a day. I gave my hour to my brother, so I missed Star Trek growing up.

When I got to college and started watching it, it just didn’t click with me the same way. I had friends who were Star Trek diehards—watched every episode, every season, ten times over. But I didn’t connect to the characters the same way.

Steve Brotman: I was hoping for a deeper answer.

Brad Feld: (Laughs) The deeper answer is this: the things that shape our childhood views really stick. But if you want to go deeper, some people say Star Wars is capitalist and Star Trek is socialist.

Steve Brotman: Right.

Brad Feld: But I’ll take a different angle. Star Wars is simpler—it has clear good vs. evil. Star Trek is more nuanced. In Star Wars, you’ve got team blue vs. team red. It sort of maps to the world we’re in today. Star Trek is more complex; the world-building is broader. So maybe I’m just being a simpleton by preferring Star Wars.

Steve Brotman: No need to dwell on it. Have you seen the new Superman movie?

Brad Feld: I haven’t yet. Is it any good?

Steve Brotman: I asked my kids, and they gave it a thumbs down—judged it by the trailer. But how many times can they refresh that franchise? Talk about mentorship!

Brad Feld: That’s actually a good metaphor for companies. If you look at companies over a long arc—and you asked me earlier about mentors in venture capital—there are two others I’d consider peer mentors: Fred Wilson and Jerry Colonna.

Fred and Jerry were starting their investing activity around the same time I was, and we overlapped during the SoftBank experience. SoftBank was one of the sponsors of their fund, Flatiron Partners, along with Chase Capital.

I ended up doing investments with both of them and becoming close friends, in different ways. Today, our relationships are still close. I’m extremely close with Jerry. If you can have a non-romantic soulmate, Jerry is probably that for me.

Back in the 1990s, we were all figuring this stuff out together. We learned a lot—through successes, failures, and just doing it. One thing I remember that was foundational to Jerry’s investment approach was a phrase: “analog analog.”

It was an idea that, in the first wave of internet investing, when they saw a digital idea, they’d ask: “What’s the non-digital analogy?” The analog of that idea. So it got shortened to “analog analog.”

So if someone said, “We’re going to build an online classified ads business,” the analog was newspapers. If someone pitched online ticketing, the analog was physical box offices. That framework influenced a lot of what got funded—some of it successful, some not.

Fast forward to 2007 or 2008. We began to realize: a lot of the ideas from the dot-com era were right—they were just too early. We didn’t yet have broadband, mobile, good browsers, cloud infrastructure, APIs—any of the things needed to scale them. Once those pieces were in place, a new wave of those “analog analog” ideas started working.

It’s fun, from an investment thesis standpoint, to look back and ask: “What were the dot-bombs that actually scaled later?” Things like DoorDash or Instacart—they’re effectively new versions of Webvan and Kozmo.

Steve Brotman: Right.

Brad Feld: Nothing new to see here, right? In ticketing, you had companies like StubHub, which after a long journey is still around. We’re investors in SeatGeek, which we think is 10 times better than StubHub. But the core idea? Not new.

So that’s a useful exercise. You could probably write an investment thesis around “let’s find all the dot-com ideas that were too early and now build them with today’s infrastructure.”

And fast forward to today. Let’s make it contemporary. Think about customer support. I think online customer support as we know it is done. It’s now an AI problem—and AI is solving it.

But the real opportunity isn’t chatbots. It’s building the infrastructure that makes AI-driven support actually useful. We’re investors in a company called Help Scout that I think is leading in this space.

A simple example: I’ve started writing code again. I hadn’t written software since the early ‘90s—stopped commercial programming in ‘92. But the tools were evolving so fast, I couldn’t keep up. I write books because English doesn’t change as fast.

Now, with tools like Cursor—where I use Claude as the model—I can actually be productive again. I have Linear running to track work. And with proper rules and prompts, I can get real output from these AI tools. It’s fun.

I’ve noticed that Claude is currently better than OpenAI for a bunch of coding tasks. That might change with the next GPT release. But both still make mistakes. Sometimes they’ll hallucinate or give outdated info.

Even when you ask for the most current answer, unless the tool is truly integrated with fresh data, you might still get old or wrong information. I’ve learned to link to the actual docs when I need the most accurate instructions.

Apply that to customer support: if you go to WordPress.com’s support chat and describe your exact problem, it does a pretty good job at giving you a specific answer using up-to-date data.

Compare that to older systems—FAQs, forums, etc.—which point you somewhere and make you dig. Now, AI tools are actually solving the issue directly. That’s a huge leap forward.

Back in the early internet days, support systems were static. Then came web-based knowledge bases and ticketing. Then live chat. But it always ended with, “Click here to talk to a human.” Now, the AI is often solving the whole problem.

Steve Brotman: Yeah, no, I think you’re absolutely right. I was just thinking about Kozmo—we were an investor. We’re investors in goPuff now. Half the battle was getting over Kozmo to pull the trigger on that deal.

Half my brain was like, “What are you, crazy?” But it does feel like the technology’s there now—what wasn’t there before.

Brad Feld: There’s no question. And the economic dynamics of these companies are evolving too—especially in the post-COVID, higher-interest-rate era.

Many of these businesses were built on risk-seeking capital—subsidized by VCs and public markets. They had completely uneconomic models. But now, to survive, they’ve had to shift to profitability.

I was in a car with an Uber driver recently in Kansas City. I asked him how long he’d been driving Uber. He said eight years. I asked how it was going, and he said, “It’s pretty grindy.” That was the word he used.

I asked if it had gotten better or worse. He said, “It’s gotten steadily worse every year.” His economics got worse, the algorithm gave him less compelling routes, and his take-home per hour kept going down. More stress, more work, less money.

And that’s what happens when companies go from subsidized growth to having to operate with real economics.

But the next wave of companies—like goPuff—have learned from that. They’re starting from a place of understanding unit economics and infrastructure. And many of the investors who subsidized the last wave aren’t as willing to do it again—because now they’re pouring money into AI instead.

Steve Brotman: Well, there you go. That’s it. That’s the ticket. You mentioned vibe coding—you’re using Cursor. Are you still deploying capital in new deals, or are you done?

Brad Feld: Yeah. Foundry still has a handful of new investments to make—maybe as many as five. Then we’ll have finished making new investments from this last fund.

So we’re still very active in the market, looking around. Of course, like any venture fund with a large portfolio, we have a lot of reserves for existing companies. So we’ll continue to support those.

We also have re-ups for funds we’ve already invested in—probably through the end of next year. But we’re not looking at new funds per se.

As for Cursor, the subsidization model is really interesting. I’m paying $200 a month for the top-tier package now because of how much I use it. There is no way—no way—I’m using less than $200 worth of API costs. It’s not possible.

Steve Brotman: So you’re being subsidized. Is there a business there?

Brad Feld: Time will tell. When I started with Cursor, it was $20 a month. I never hit the limit while building the first project—a game called Dynastrides, which is Asteroids but with dinosaurs. It’s at oids.com. I was a big Asteroids fan as a kid, so I wanted to play around with a project I was familiar with.

Now I’m working on something else. I just released a new book—it’s my ninth book—and I should have my act together by now in terms of all the things to do post-launch. But I didn’t. It was a mess.

So I’m building tooling for myself to manage the process better than with emails and spreadsheets. And it turns out to be a fascinating problem. And now Cursor keeps telling me, “You’ve hit your limit—upgrade!” And I do.

I’ve also tried Lovable, which is one of the hot companies right now. I found that $20 doesn’t get you very far there. You get maybe one serious working session, and then it says, “Give us another $20.” That adds up fast.

So, these companies are subsidizing usage heavily—and that’s changing. The question is whether the foundational model providers are converging on being profitable or still burning capital to scale.

Will user lock-in and scale eventually normalize the economics so light users subsidize heavy users? I don’t know. But just the other day, Anthropic announced they’re rate-limiting Claude for the top 5% of users because people are just running Claude in the background all day now.

Steve Brotman: Why not? You can have an Uber driver outside your home at all times—same idea.

Brad Feld: Exactly. So the question becomes: how do you think about this?

There’s understanding it by living the problem, understanding it by recognizing historical patterns, and understanding it by thinking critically. And as an investor, that matters.

If you have infinite capital—or access to it—subsidizing for scale might be fine. But most investors don’t. So understanding how to assess and underwrite these models matters, especially once you’re out of the hype cycle and into the middle part, where unit economics start to really count.

Steve Brotman: So: live it, know the history, and what was the third one?

Brad Feld: Think about it. Use critical thinking.

Don’t just ask ChatGPT what to invest in. Don’t just follow the herd. We all know the cliché: the investor who jumps into the hot sector because everyone else is.

That’s not about being contrarian. It’s about thinking hard. You’re going to make mistakes—this business is built on that. More things fail than succeed in venture capital. I accepted that a long time ago.

If you haven’t accepted that, you’re in the wrong business. And if you have a track record where that’s not true, good for you—but it probably just means you’ve only been a VC for a short time.

Steve Brotman: Or they’re lying.

Brad Feld: Or lying. I remember in the ‘90s, a very famous VC said in an interview, “I haven’t had a single company fail.”

And I was like, “That’s bullshit.” I was on a board with him, and the company failed. So yeah—accept that many of your investments will fail. And understand why. Was it the market, the model, the execution? Was it a board decision? Was it just bad timing?

It’s important to be a critical thinker about your own investments—especially when a category is out of favor. Like DTC—direct-to-consumer—after 2020, every VC jumped on that train: “No one will ever go to stores again.” Tons of money flooded in.

Now? Ask those same investors if they’ll do DTC and they say, “Nope. Doesn’t work.” That’s not true. It just requires understanding why some of those models failed—and which fundamentals still matter.

Steve Brotman: That’s the thing. DTC wasn’t a bad idea—it was just overfunded, with flawed assumptions. Or maybe bad timing.

Brad Feld: Exactly. And when the tide goes out, you see who’s swimming naked. But that doesn’t mean the ocean is broken. There are still good swimmers out there.

It’s the same with AI. We’re in a cycle right now where every pitch deck mentions AI, whether it’s relevant or not. But the question remains: is this a business or a feature? Does it have defensibility? Can it scale?

Many of these companies are features, not standalone businesses. Some will get acquired. Some will never find product-market fit. But that doesn’t mean AI as a category is a bust. It just means we have to apply discipline.

And this isn’t new. This is what investing through cycles teaches you. It’s one of the few advantages of aging in this business. You’ve seen enough to recognize patterns—but you still have to do the work.

Steve Brotman: Right. And the discipline piece—it’s easy to forget when you’re chasing hot deals or following the crowd.

Brad Feld: Totally. And look, I’ve made plenty of mistakes. That’s part of what I try to share when I mentor younger investors or fund managers. I’ve made mistakes at every level—picking companies, managing relationships, building firms. You name it.

But the mistakes are where the real learning happens. And if you can share those lessons with others—especially people earlier in their journey—you create leverage. That’s the idea behind Give First.

Steve Brotman: Let’s talk about the book. Why now?

Brad Feld: I’ve been thinking about writing this book for a while. The idea of “give first” has been central to how I operate since the early days of Techstars. It became a core value of the accelerator and, eventually, of Foundry too.

But I realized we never really explained what it means. People would say, “Yeah, give first—sounds nice,” but they didn’t always understand the depth. It’s not just about being nice. It’s about being intentional. It’s about playing the long game.

So I wanted to codify that. I wanted to share the philosophy, the mechanics, and some real stories from people who live that value. People like David Cohen, who co-founded Techstars with me, and many others in the ecosystem.

Steve Brotman: And mentorship is the core of that philosophy?

Brad Feld: Yes. Mentorship is the vehicle. But it’s more than that—it’s about how you show up in the world. It’s about giving without expecting anything in return, but trusting that the universe has a way of balancing things out.

And to be clear: it’s not martyrdom. I’m not saying “give and get nothing.” I’m saying: give because it creates a better system. Give because it builds trust. Give because it’s the right thing to do. And over time, that comes back—though not always how or when you expect.

Steve Brotman: That really resonates. Especially in this industry, where transactional thinking is so dominant.

Brad Feld: Yeah, and I get it. We’re all operating within incentives, structures, fund cycles. I’m not naïve about that. But what I’ve seen is that the people who truly play the long game—who build relationships based on trust, not extraction—those are the ones who have lasting impact.

And honestly, they tend to have more fun too.

Steve Brotman: Amen. Brad, this has been amazing. Thank you for sharing your wisdom—and for continuing to lead by example.

Brad Feld: Thank you, Steve. It’s been a joy. Appreciate the thoughtful conversation, and congrats again on what you’re building with Alpha Partners.

Steve Brotman: Thanks again. Take care.

 

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