Brad Feld: Founding Techstars, Giving First, and Mentorship
Smart Friends Episode 97: Brad Feld
Today, I sit down with legendary venture capitalist Brad Feld. He’s the Co-founder of Foundry, Techstars, and author of multiple books including Startup Communities and Give First.
Brad reflects on the mentors and moments that shaped his career. He shares stories from his 40+ years in tech and investing, digging into how he thinks about mentorship, success, writing, control, and showing up consistently over time.
We dive deep into the philosophy behind his new book “Give First,” unpacking how generosity and curiosity have guided his journey across decades of venture building and community leadership. Throughout our conversation, Brad shares honest lessons about evolving with time, finding joy in creation, and remaining grounded in the work itself.
Links to Platforms:
We discuss:
The role of heroes and mentors in shaping Brad’s values
How "Give First" transformed startup culture
How to let go of control while still fighting to the end for what matters
Key mentors like Len Fassler and the life lessons they gave him
Why reading, writing, and coding all serve as reflective practices
Quotes from Brad:
"The best way to fly is to throw yourself at the ground and miss." (Zaphod Beeblebrox quote that Brad uses to describe startups)
"I love to help things get started. That’s my favorite part of the journey."
"Fight to the bitter end. You try until it doesn’t work anymore."
"Some things don’t end. Some things outlive you—which is delightful."
"The future does not belong to me. The future belongs to people 40 years younger than me."
"Give First is not a religion. It’s a philosophy."
"Your VC’s are not in control. The board members are not in control. The CEO is in control."
"Books are core to so many things I do. Reading and writing are how I process the world."
"I write books to understand better an idea and work out the idea."
"Mentorship is about ways of being, not about following a set of rules."
"Hibernation from social media gave me the creative space to finish the book I actually wanted to write."
"People said, 'Brad’s the king of the Colorado startup community.' I hated that. I don’t want to be king—I want to be just one of the many leaders."
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Learn more about Brad Feld:
Additional episodes if you enjoyed:
Cal Riley: Special Ops, Grief, and Why Your Business Needs a Heart
Building a Venture Firm From Zero to One, and AI-driven VC Thesis Research
Toby Rush: $100M Exits, Splitting Companies, Timing Startups, and Ideem Killing 2FA
Episode Transcript:
Eric Jorgenson: Let's let it rip then. You are a legend among venture capitalists, having venture capitaled since the 1900s, as it's fashionable to say now.
Brad Feld: 1873.
Eric Jorgenson: Pre-millennium. I like to start, and it's one of my favorite just like get to know you questions at dinner, with like, who are your heroes?
Brad Feld: Oh, I have so many heroes. Zaphod Beeblebrox is a hero of mine.
Eric Jorgenson: Why is that? That's an unconventional choice, but I like it.
Brad Feld: Well, I read Hitchhiker's Guide to the Galaxy when it first came out and I fell in love with Douglas Adams, the writer. I actually saw him once when I was at MIT. He came and gave a talk. He's since passed, but he was 12 feet tall and just unbelievably hilarious. For people who don't know Zaphod Beeblebrox, he was the president of the universe. He was a knucklehead, but he had some great lines. My favorite of his is, the best way to fly is to throw yourself at the ground and miss. For me, so much of creating companies is to throw yourself at the ground and miss. You just try shit, and hopefully, you don't fail. I had an investment in a company called Harmonix that was started by these guys, Alex and Aran. Harmonix did Guitar Hero and Rock Band. They had a huge overnight success that for the first 10 years, they're a massively successful company, for the first 10 years of their life, they tried very, very hard every year to go out of business and were unsuccessful. So that's a Zaphod. I have always loved Albert Einstein as a thinker. His willingness and ability to think on his own was sort of an inspiration to me. Warren Buffett is another business example of a hero for me. He just did his own thing his way. Lots of people didn't get it. Some people did. He held true to his values for a very long time, over a very long time, very consistently. He's open now about some of his ups and downs in life, but he really just tried to wake up every day and do his thing. His partner, Charlie Munger, who passed, would be another one in that category. I find Charlie to be inscrutably wonderful. There you go. And he reminds me of another hero, the guy bought I my first company, his name is Len Fassler. And Len passed a few years ago, but I learned more from Len, not just about business, but about how to comport oneself in life than I think I have from almost anyone else. So, those are some of the heroes on that side. Current, interestingly, current heroes of mine that are contemporary Paula Johnson who's the head of Wellesley College where my wife Amy went to school in my mind is a totally heroic figure in terms of what she's done in life and how she does it. A woman Lucy Sanders who I'm very close with who created the National Center for Women & Information Technology, I was the founding chair of it, probably has had the most to do with girls and women getting involved in computer science over the last 20 years. Amazing what she's done. And another person I'll just call out that's also contemporary is a woman named Wendy Lee who, very successful entrepreneurial career and for the last decade or so has really, first in Cincinnati and more recently in Colorado, dedicated herself to helping at the intersection between public policy and public service and entrepreneurship without being in government. And some of the stuff that she's done has just been awesome.
Eric Jorgenson: Yeah, it's a big and interesting ecosystem of all the people who try to support entrepreneurs. Part of how I came into this was actually through Startup Weekend and through the Kauffman Foundation, which I think are both things that you've worked closely with over the years, just finding happy paths for people starting their own companies or having their own form of success. So many people have their hands on that over time.
Brad Feld: For me, it's awesome. If somebody says, hey, Brad, where do you fit in in terms of how you think about yourself in the world? I love to help things get started. I've been involved in lots of things for long periods of time, but I really love the inception. If you think about some things, you mentioned two organizations that I care a lot about, Startup Weekend. The very first Startup Weekend happened in Boulder in 2007 during the very first Techstars program, and then for a number of years after Startup Weekend started to become a thing, I ended up on the Startup Weekend board. And then over time Startup Weekend ended up merging into Techstars, which I was a co-founder of and am still on the bord of. Kauffman Foundation which was a very early supporter of Startup Weekend and Lisa Mitchell, close friend, who today is at Alloy Ventures, but was for a while at Techstars, prior to that was at Kauffman, but preceding Lisa in the 1990s, I spent time at Kauffman. I got to know a woman, Jenna Matthews, through kind of a random linkage with some entrepreneurial stuff I was doing at MIT that Kauffman did. I ended up spending about a month, a day a month for a couple years in the 90s in Kansas City at the Kauffman Foundation working with Jenna on a team she had that turned into a very bad acronym called, the program name was Learning Programs for High Growth Entrepreneurs, our acronym was leapfrog. Terrible acronym. But all of these things, the early stages of them, for me, so much joy in having them go... I didn't know you'd gotten involved via Startup Weekend. It just brings me great joy to know that that touched you at the beginning of your startup journey. For me, having to be in control, still be actively involved and drive, that's not important to me. That's never been part of my shtick. It's really fun as I approach, I'm about to turn 60, as I approach 60 to look back and just, obviously, I've had lots of companies and things that have been successful. I've had lots that have failed. I think most of the joy doesn't come from those, the failures don't generate joy, but the successes, I don't even think are what generates joy. What generates joy is all these little seeds all over the place that impacted people on their own journeys in ways that was meaningful. That's really joyful.
Eric Jorgenson: Yeah, I'm definitely one of those seeds. I mean, growing up as a kid in Detroit, Startup Weekend was my path from from like, I won a Twitter contest to go to a Startup Weekend. And the judges introduced me to somebody who brought me to Kansas City, which brought me to Kauffman, which then I joined a company that was born at a different Startup Weekend. And that moved me to San Francisco, and that got me into the ecosystem, and got to meet all these incredible people and kind of create this cohort of people that came through Startup Weekend at the same time. And it's like... Yeah, I'm one of the legions of people that kind of your forest has nurtured over the years, which is a really cool full circle moment. I'm curious, as a starter, like you love starting things, how do you know when to step away from something that you started? I imagine that's hard. You feel load bearing. You feel like your personality is wrapped up in this thing. Like that's a huge decision and you've made it dozens of times now.
Brad Feld: Yeah, well, there's two different dynamics associated with it for me. And I've had to understand how to separate them. They were hard, certainly when I was younger. And I'll separate them between things where I am in a key committed role, and I learned this from Len. A lot of VCs, when things go sideways, kind of walk away or stop paying attention or that's not worth my time. A phrase I hate, which is return on invested time or return on time, I don't like that. I don't like those phrases because they don't really apply. They don't make sense. I understand what people are saying with it, but they don't make sense to me in terms of my own value system. I learned from Len, you fight to the bitter end. I mean, you just try until it doesn't work anymore. And so, for me, from the standpoint of things where I have functional responsibility, I'm a major shareholder because I'm an investor, I'm on the board, I'm a co-founder, I feel in those situations, I feel responsible to stay through the end, whatever the end is. Now, that doesn't mean that if I'm not wanted that I have to stay. There have been some cases where it's clear that my presence wasn't valued anymore, there was no reason for me to be around, so that's different. But my core is fight to the end. I really did get that from Len. But I separate that from holding onto control. So, one of the things that happened in the internet bubble for me, so this is 2000-ish, before the bubble burst, I had co-founded a number of companies, including a few that were very, before the bubble burst, very, very successful. And as co-founder of those companies, I was very deeply and emotionally involved in those businesses. But I also had invested in a lot of companies, both as an angel and then subsequently as a VC. And I was on an absurdly large number of boards. Somebody ended a podcast with it the other day by asking the question, was it true that...? I'm like, geez, really? That's what we're going to end with?
Eric Jorgenson: I mean, what's an absurd number?
Brad Feld: Well, I don't know the actual number. I don't remember. I don't have it.
Eric Jorgenson: That’s high enough.
Brad Feld: It was more than 25. The podcast question was, was it true that you're on 35 boards? I'm like, I have no idea if that was the number. And of that, it was of a handful, four public company boards, five international boards, and then just a ton of boards at all levels. When the internet bubble burst, I mean, my world was a gigantic pile of shit. But for me, again, this sort of one part of my brain that's like fight to the end, I separate that from the part of my brain which is hang on to control. So, in the world where I was the co-founder of some of these companies, I felt this overbearing emotional responsibility for the outcome. And so I felt this dynamic around control as an operator. As an investor, from day one, I knew I wasn't in control. The investor's not in control. Your VC's not in control. The board member's not in control. The CEO is in control. The founder is in control. And my job as an investor board member, from my frame of reference, is as long as I support the CEO, my job is to help her be successful. And when I get to the point where for some reason I don't support her anymore, my job is to do something about it, which is not necessarily replace the CEO. It's to try to get back to a place where I support her. And I had these two parts of my brain that were at war with each other. One of them was this sort of inappropriate sense of responsibility in a lot of cases for things I didn't have really the responsibility for or the ability to control. So that was 25 years ago. So in that time period, that's when I really learned how to link these two ideas together. One of them is fight to the end, whatever that is, and some things don't end. Some things outlive you, which is delightful. But on the other side of it, it's to not have this inappropriate responsibility for things, not try to control what's going on. If you fast forward 10 years or a dozen years later to 2012 when I wrote Startup Communities, it was the book that I came out with, this third book that I wrote, one of the things that I wrote in that book was the importance of there not to be- there'd be multiple leaders in a startup community, but not one leader try to control what's going on in the startup community. And one of the experiences I was having by this point in time was I had become very well known both in Colorado, but also outside Colorado for many things I'd done. And people would say Brad's the king of the Colorado startup community or the Colorado- the phrase startup community didn't exist at that point. So Brad's the king of Colorado startups and Brad's the person blah blah blah. And I fought that. I'm like, no, Brad's the leader. No, I'm one of the people who are leaders. I had a paragraph or a section in that book called The Patriarch Problem, and I said one of the reasons that startup communities get stalled over time is that the people in control, which at the time were mostly older white guys, tried to hang on to control well past the point where they should. The key is that you constantly want new energy in the system, you want new people, you want the next generation, you want new leaders. And so, I had this evolution of my own experience where I realized that I was on a bunch of nonprofit boards, I was chair of some things, and I woke up one day, I'm like that's not being helpful. Because people are looking to me to control what's happening versus allowing those things to evolve and grow, and I can be just as influential and just as impactful without trying to be in control. Now, as I approach 60, it's not an ageist statement, but the future does not belong to me. The future belongs to people who are 40 years younger than me. Part of what I can do is participate in constructive and helpful ways, but if you look at our society and you look at all the people late in life still hanging on to power and relevance, rather than contributing in really significant ways, on the path of what the future generations want, it's so easy to say I'm just doing this for my kids, I don't have any kids, but you're saying doing this for my kids and for my kids’ kids. And you look what the person's doing and you say, no, actually you're doing that for your own ego. You're doing that because you're maintaining relevance. You're doing that because you're trying to control the outcome in a certain way that suits you that might or might not be the thing that other people want. And so, in that 2012 time frame, when I made that statement, I really committed personally to being a constructive force that was not having to be in control.
Eric Jorgenson: Yeah, that's a very interesting thing to segment, control and presence and how you show up in an organization and the level at which you choose to engage in it. Will you tell me more about Len?
Brad Feld: Len was wonderful. I miss Len every day. I met Len when I was 28 and he was probably about 60. And I was running a little company in Boston. It was very creatively named Feld Technologies. I like to say I named it after my dad. It had no funding. It was just me, a business partner, a guy named Dave Jilk, and my dad, who was an advisor, and we gave him some equity. We had 10 shares of stock, each a dollar, and we split them up, six to me, three to Dave, one to my dad. When we sold the company, we still had 10 shares of stock, and fortunately, they were worth more than a dollar. And we just built this business that ended up being a really good business. We had a great culture internally. The team was a young team, mostly of software developers, and we were writing business applications for businesses, not just locally in Boston. We had clients all over the country, but we were writing business applications in the late 80s and early 90s when it was really hard on PCs to write stuff, write software, to make networks connect to each other, where packaged applications weren't very configurable, where a lot of people were coming off mainframe or mini computer systems and trying to implement PC and PC-based networks. Our motto as a company became, we suck less. That was our motto because we were often the second or third company a company had hired to do this. The first one or two had failed. And we would sit down in the first meeting and they’d say, well, we've been doing this for two years and we were supposed to have this in production six months ago and we have no more money, but can you fix this? Our line was, yes. Our job is to suck less than the last people. But the problem that you're out of money and you’re past time is not our problem, that was their problem. We'll suck less than them, but we need to reset this. It would set the tone of people would be like, yep, okay, I get it, let's figure this out. I met Len kind of randomly through a company that his company had acquired, that was a company called Allcom, that we had done some work with in Boston. They were a cabling company. So when you set up a network in the 1990s, you used to have to actually cable the buildings and put the cable in the walls, which was no easy feat. So they were like specialized companies that did that. And Allcom was a good company, and Jim, the guy that ran it, had become a friend. And he called me one day and said, hey, we just got bought by this company in Stanford, Connecticut. The chair is coming, the founder’s coming to Boston to do some stuff, and can I take you out to lunch with them? I said, yeah, sure, why not, free lunch. I met Len and I spent the first half of the discussion not having any idea why Len was sitting here. He's this older guy. He's wearing his sport coat and his tie. He's a little formal, not overly so. He's pretty accessible, asking me a lot of questions about what we did. We're having a nice conversation. At the end of the conversation, he said to me, Brad, Jim has said really amazing things about you. Jim Galvin was the guy's name. Jim has said really amazing things about you, and I really like what you guys are doing, and we'd like to buy your company. I looked at him. I said, do you want to think about it? He says, Brad, I learned enough in the first 30 minutes about you to know that I want you to be part of my company. That generated a long conversation and negotiation. We ended up buying the company. But for me, that was such an unbelievably aha moment because I never thought about buying a company or selling our company or anything like that. I was just running a business. And what happened over time with Len was not that he- that wasn't impulsive. I mean, he knew what he wanted. He wanted to buy a small- he was buying companies that were systems integrators, companies that would sell hardware and install network. And this was at a point in time where you could still make 30% gross margin selling hardware. And there were a whole bunch of companies that did that sort of thing. They were called systems integrators, I think was what became the name, but there was a name before that. It was mostly Novell Netware for the old people in the audience. Microsoft Windows NT really become a thing yet. There was no Internet. It was hard. It didn't work very well. Most people sucked at it. And he knew... What we saw and what he wanted was he wanted to buy a small company that could write software and do the services thing, and we were very profitable. We had a good business and we're making good money. He looked at it and said, I could build off of this somehow. This guy, Brad, I like. I want him on the team. That started a long relationship where I ended up on the deal team with him and his partner, Jerry Park. I was the technical guy, so I learned how to do deals by watching them do deals. It was in 1994, so I took most of the money that I made and I made a bunch of angel investments in companies at the beginning of the commercial Internet, including some with Len and Jerry. I had no idea how to do an angel investment. All of a sudden, I was doing an angel investment a month, which today is not that fast, but in the 1990s, it was unheard of that somebody would do more than a couple of angel investments a year. And I just used Len's approach. I'd meet with anyone and I'd sit down and within 15 minutes, I'd decide whether or not I really wanted to work with the person or not. And for me, the parameters were, do I have interest in what they're doing? Do I care about the product? And do I want to be partners with the person? And that was it. There was no like, I need to do diligence, and can I see your financials? These were raw startups. These were ideas. They were little baby things. And I would say that was something I learned so deeply from Len, which is, be willing to take risks on people, but make your judgment quickly based on whatever your format is, and then put energy into it and see where it goes, which of course is a core part of my own personal philosophy around being willing to put energy into things without knowing where they're going to go. I don't have to define transactionally what the dynamic is. The other thing that I'll just say about Len is, he was the kind of person who no matter what was going on, no matter how hard it was, he just got up and did the work. He had enormous success. He had a huge following of people from his life that would do anything for him or with him. And that loyalty didn't come from him demanding loyalty at all, saying you must be loyal. It's just from behaving in a way that engendered people want to be with him, want to spend time with him, want to be helpful. And he was incredibly generous with his time, his energy, his emotion. He took on hard problems. He was willing to deal with confrontations. He had some broken relationships, as we all do, as I do, as anybody does. That's life. You're going to have some relationships that break. But no matter what was going on, he just got up and was willing to do the work and willing to engage. The positive side of that was in the joyful moments, they were wonderful. In the difficult moments, and he and I had many of them in one of our companies that we did together that went public and it was worth over $3 billion at one point and then went bankrupt two years after the internet bubble crashed. We'd have days where at the end of the day, all you could do is go for a walk. He loved to smoke cigars. Just go for a walk and he'd smoke a cigar. You'd whine a little about how shitty the day was and how hard this was, that was, and then you'd get done with the walk and you'd sit down and be like, you know what, get back up tomorrow morning and try again. Just that tone of recognizing this life thing, it's full of good things and it's full of hard things. It's just life. Do your best.
Eric Jorgenson: Was he someone who you admired the whole picture of their life? Or was this something that's like- I feel like it's always a puzzle when you're kind of choosing mentors of like, do I admire this person's talent in their domain, or do I admire, I even appreciate all the trade offs that they've made in the whole picture of their life and respect and want sort of the big puzzle that they put together, not just one particular trait that they've over optimized on?
Brad Feld: It's a lovely question. A whole picture of his life. I became good friends with his son, David. I love the relationship that he and David had. I saw how he dealt with really difficult personal situations, including the passing of both, his first wife passed of cancer and then the second wife also passed of cancer many years later, and I watched him deal with Bunny having cancer and then subsequently passing and just the love and grace at which he dealt with that. He was very comfortable in his own skin. He didn't have to be the richest guy in the block. He didn't have to be the most successful guy in the block. He didn't have to be the most whatever. He knew what he wanted and he focused on that rather than something artificial that somebody else maybe wanted or that he thought he should have because. Now, the whole picture, my answer is, I'm not emulating Len, I'm being my own person, but in the context of that and in terms of how he interacted with people over a long period of time, even in situations that were challenging, lovely is the word I used a few minutes ago. It was lovely. It was inspiring. It wasn't like, oh, he was such a humble guy, he had so much humility, blah, blah, blah. It wasn't that. He was just him. He didn't try to be somebody else. And he evolved and grew. I mean, I got him to stop wearing ties and eventually I got him to stop wearing sport coats. He would pull, when I had a ponytail, he'd pull on the end of my ponytail. There was love, and it just made everything, whether it was work or not work, whether it was easy or hard, whether it was successful or not successful, whether it was short or long, it was just, I use the word lovely, it was a lovely way of being. And he and I, I wrote a blog post when he passed that touched on a bunch of things. And I put a picture of it, of a morning we had together. And that morning was, I was in New York for the Fitbit IPO. I was an early investor in Fitbit. I was on the board. It was a huge IPO. It was the largest, I think it was the largest consumer products IPO since sometime in the 90s, for a long, long time. It was a really substantial deal then. Internet companies were still, some companies going public, stuff like that. For me, it was a tremendously successful thing, but it was also just exciting. I came in the night before and you have... I came in the day before and you have the final banker meeting to price the deal and all the nonsense that goes around with that, and then you have a big party. I think it was in the Rainbow Room or something, looking over Manhattan, and everybody's joyful and having a wonderful time. I go to my hotel room, and the next morning, he and I go for a walk before I went to the New York Stock Exchange to ring the bell. It was early morning that the two of us got together. We got together, and we went to- I was staying at the Gramercy Park Hotel, which I stayed at regularly, and it was next to this little park called Gramercy Park. He had gone to Baruch University. Maybe it was the morning before the pricing and stuff, I can't remember exactly. We met for breakfast at the hotel, and he said, you know, Brad, I've never been to that park. I went to college across the street, but I'd never been to that park. I said, Len, fuck it, let's go to the park. I went to the desk and I said, is there any way we can get into the park? I'd never even really thought about the park before. They said, yeah, all the hotel guests can go to the park. Here's the key. We went into the park and we sat on a bench for like 30 minutes. And he said, this is the greatest. I never did this. It was a beautiful day, Manhattan, sunny day, nobody was out yet, and we just sat there and just were together. That was Len.
Eric Jorgenson: It's amazing the people in our lives who can change our lives just by being themselves, like they don't set an example that we have to emulate but they set an example of what true happy authenticity looks like and someone just like walking their own path, and you're like, oh yeah, that's an inspiration for me to walk my own path, not to walk yours.
Brad Feld: You nailed it, Eric. You summarized my last 10 minutes in 30 seconds. You nailed it. It's the inspiration to be yourself, not to try to be someone else and the courage in today's world to be comfortable with yourself, whatever that is. And that's especially hard with all the stuff. I mean, it was hard when I was a kid. It's probably been hard from the beginning of our species. It's especially hard with the amount of stuff that comes at you every day, all the different stuff about how to be and what you should and what you shouldn't and what's good and what's bad and all the nonsense and the number of people who are, just whatever the bullshit that's coming out of their mouth is, because they're trying to accomplish something. Whatever.
Eric Jorgenson: We've invented some memetic super weapons in the last couple of years that really prey on our natural weaknesses. Are there other key mentors that were inflection points in your life or that gave really important pieces of who you ended up becoming?
Brad Feld: Yeah, I had some big early ones. My dad's younger brother, Charlie Feld, who's still a close friend, was key. When I was 12, I got interested in computers randomly. Charlie was, at the time, the head of data processing for Frito-Lay. Today, he'd be called the CIO. He was one of the dozen or so IT leaders who invented the idea of a CIO. But at the time, when I was a little kid, he was head of data processing. And I was interested in computers, so he would take me to the Frito-Lay Data Center in Dallas where I grew up. That was this giant data center underground in downtown somewhere, and I would sit in front of a terminal. One day, it was a Saturday, he was busy, had a bunch of meetings, and he sat me down in front of a terminal, handed me a book that on the cover was a black book with a red cover. Again, old people might remember this, and the cover said, A Programming Language. The programming language was called APL, which was the TLA for a programming language. It is the weirdest programming language that probably existed at that time. If people don't know APL and you're curious, go look up APL on the web and you'll see that it had this bizarre keyboard. It was a very compact language. In five or six hours of sitting in front of this terminal, I was absolutely amazed by what I could do by typing these keys into this thing and having this thing do stuff. He continued to encourage me as a teenager. Then when I went to college, I was in Boston, and he would regularly come through Boston to meet with Digital Equipment Corp, now DEC got bought by Compaq and then got bought by HP. So, he’d meet with DEC. He’d meet with Lotus which was just down the block from where I was going to school at MIT. And he'd have me sit, he’d invite me and have me sit in meetings that I had no business being in with the leaders of these companies as a 17, 18, 19 year old. It wasn't like, hey, Brad, go sit in the corner and be quiet. He'd let me sit at the table. I wouldn't say much, but every now and then, I'd ask a question, and I met these people, and I really got a sense of some of these things. And that was really powerful. I started my company about five years before he left Frito-Lay and then started his company. By the way, us Felds aren't terribly creative, so his company's name was the Feld Group. And so for a period of time, you had Feld Technologies and the Feld Group. He was starting his business, and all of a sudden, the magic trick of mentorship happened, which... speaking, a mentor and the mentee become peers and you start learning from each other. So all of a sudden, even though I viewed him as a mentor, now he sees me as a mentor because my business is much bigger than his, and he's asking me questions about this, that, and the other thing in terms of getting the business going. That was very powerful. Then subsequently, right around 1999 or 2000, I ended up, when I was at SoftBank, which then became Mobius, we invested in the Feld Group. I joined his board and joined his management company and continued to work closely with him. Then EDS bought the Feld Group at some point. It was a nice exit for everybody, a very nice exit for Charlie and the other founders of the Feld Group. Those experiences were powerful. So, he would be one. Another were the husband and wife Chris and Helena Aves who had a company that was the first company I really worked for. It's a company called Petcom. When I was a senior in high school, I got introduced to them by, I don't remember who, maybe a patient of my dad's or something. I ended up working for them the summer of my senior year in high school, and then while I was in college, I worked part-time for them. When I started working with them, it was just the two of them, so it was the three of us. At their peak, it was a 20-something person company, and then the oil and gas boom in Texas burst. The price of oil went from, I don’t know, 40 down to 10 or something, and all their customers who were petroleum, oil and gas exploration companies all went out of business, and their business shrunk. But they continued to do stuff and to make it happen. I learned so much from Chris and Helena about starting a company and what being in a company as a founder look like. And then I learned two really powerful things personally. One was they paid me by the hour. So I learned pretty quickly that if I worked 80 hours a week, I made twice as much as if I worked 40 hours a week. And they were paying me the princely sum at the time of ten dollars an hour for writing commercial software for them, which was just a job I loved. I mean, I would stay in this office that we had till two in the morning in front of my PC writing software. And then actually, I was an all-nighter kid for a while when I was in college. I would do an all-nighter once a week. So when I would come in the summers and work for them, I would always spend one night a week and stay in the office and pull an all-nighter, and they'd always come in and they'd wake me up, I'd be asleep on a couch somewhere. But the other thing I learned is they gave me 5% royalty on my software. They didn't give me equity in the company. I didn't really know what equity was. But they gave me 5% royalty, which was common in the oil and gas industry. All of a sudden in college, I was getting checks for 1,000 bucks, 2,000 bucks. I got a check once for a little bit over 10,000 bucks because they sold a bunch of my products. You're a freshman in college, you get a check for 10,000 bucks. What do you do? I took my entire fraternity out to Chinese food across the street and I still had 8,000 bucks left. It gave me this different view of money at a relatively young age in terms of, instead of viewing the job in a certain way, I said, I can be creative, I can create these things.
Eric Jorgenson: You experienced leverage.
Brad Feld: That's right. Get paid for it in a way that is linked to the thing that's done. I could give a handful more others, but those are some that jump out at me.
Eric Jorgenson: ...It's no secret that this is all probably a lead-up to your most recent book, which is Give First, and it's all about the power of mentorship. Was Len the original inspiration for that? Has this book been brewing for a while? What's the origin story?
Brad Feld: No. The dynamics around this book was in 2012, the way the orientation of the book happened, this is my ninth book, so in 2012, I wrote this book called Startup Communities. That was my third book. In that book, I created the phrase startup community. It didn't exist before that. People called them entrepreneurial ecosystems and innovation, something inaccessible to people. And I'm like, eh, need a better phrase. And I talked about a bunch of things in that book about how to create startup communities anywhere in the world. Like my view was this whole idea that you had to be in the Bay Area to create a startup was stupid. I was tired of hearing it. I was involved in something different. I grew up in Dallas. I lived in Boston. I now lived in Colorado. I created this thing, Techstars, that was now investing in companies all over the world. I personally invested all over the US with a venture fund. I was part of founder group. And I'm like, you know what, I want to put a wrap around this. And I used Boulder as the example and what was happening in Boulder, Colorado, at the time. In that book was one paragraph, it's a short paragraph, and the heading of the paragraph was, Give Before You Get. I wrote that paragraph as an afterthought. I didn't really put a lot into it, but I was trying to say with that paragraph, look, if you're a leader in a startup community, and I defined leaders in that book as the founders, entrepreneurs, and you want to be a leader in a startup community, you have to just be willing to put energy into the startup community without knowing what you're going to get back. I'd say it's not altruistic. It's not philanthropic. You expect to get something back. You just don't know when, from whom, over what time period, in what form, in what consideration. And so I wrote this paragraph. I didn't really think much about it. That paragraph had some pickup. There were a lot of conversations as the book came out, and people were talking about startup communities everywhere. Come on, we got to put energy into the startup community. Give before you get, sort of thing. And then about six months later, Adam Grant came out with a book called Give and Take. I didn't know Adam at the time and I read his book and I'm like, holy shit. Adam was or is a Wharton professor. He's an organizational psychologist. He did real research. My book had no research. It was just Brad Feld anecdotes and experiences, which is all what I do, conceptual frameworks, but it's stuff from my experience. Disagree with it, tell me you disagree with it. You don't like it, challenge it. It could be wrong. It's just experiences that I've had. I tried to frame stuff around that. But Adam had this book that was extraordinarily readable. The first character that he talks about is a guy Dave Hornick, who I also knew as an example of somebody who was a giver. And he defined givers, takers, and matchers. And he did this academic research that showed that over the long run, the most successful people, he actually did it really well, it's a good hook. He says, after he sets it up, over the long run, the people who are the least successful are givers. And he said, and the people who are most successful are givers. And then, the book talks about like what are the characteristics that separate the most successful from least successful and where do takers fit, and matchers are people, I'll give you this if you give me that or I'll do this for you. And I read this book. I'm like, yep, there's a thing here. And this is how I'm behaving. And I thought about it. And there were other people in my world that behave that way. Len was one of them, like in terms of personality and style. But there were others. David Cohen, who was one of the co-founders of Techstars, was behaving this way and how he engaged. A lot of it was philosophical and conversations that we had with each other about how Techstars should grow and evolve at the time. And then one day, at some Techstars event, remember there used to be this thing called Twitter and everybody used it. It used to be limited to 140 characters, including the hashtag. And #givebeforeyouget uses up a lot of those 140 characters. A guy named Gregg Cochran at Techstars one day was at a Techstars event and started tweeting #givefirst in front of stuff, and then all of a sudden, that became give first. That was the origin. This is 2012, 2013, 2014. It was a consolidation of some ideas that then evolved. It evolved into, I describe it very clearly today as a philosophy, not a religion. A religion has rules. If you follow the rules, well, if you're Buddhist, if you follow the rules, you're not going to get it right, then when you die, you get reincarnated and get to do it all over again. For other religions, if you follow the rules, you go to heaven or whatever. And like, it doesn't matter what your religious tradition is, there are rules. And for me, mentorship's not about rules. It's about ideas and it's about ways of being. It's about things that are effective versus things that are not effective. Give first is not, here's how you have to behave 100% of the time. It's, here's a philosophy. And I'll just give an example. I mean, the tongue-in-cheek thing that happens periodically is somebody will say to me, oh, you're that Give First VC. How about you give me $5 million, and I'll give you something. And I'm like, no, no, no. I have transactions in my world, too. But you take a part of your framing and your philosophy as, I'm willing to put energy into things without knowing where they'll go. And all of these things evolved over time. And I would say about three years ago, I wrote the first draft of this book. And when I wrote it, it was still COVID. I was tired. I was pretty tired of a bunch of stuff. When I say it was still COVID, the lockdowns were off, but there was still a COVID hangover in the air. I was tired of a bunch of stuff that was going on in the world. I was tired of some stuff going on in venture specifically. I was just worn out of a public persona of talking, doing stuff like this, being in public, and things like that. After I wrote this first draft, what happened was I got feedback, which I always get, I send it out to 20 people or so, and there were two big pieces of feedback. One was, Brad, you jammed together two ideas, give first and mentorship. You didn't really weave them together into a coherent narrative. The other was, hey, way too many Techstar stories, not enough Brad stories. We want to hear more from your experience, which was an obvious thing for somebody to tell me, but I hadn’t really... I got lazy in the writing of it. I knew what to do because I'd taken a lot of first drafts to a book that was good, a lot of mediocre to crummy first drafts to a good book. I'm like, you know what, fuck it, I don't feel like doing the work right now. Then I'm like, you know what, fuck it, I feel like taking summer vacation. And so, I stopped doing everything public. I continued to do all my work, but I stopped blogging, I stopped doing podcasts, I stopped writing, I stopped tweeting, I stopped all social media, everything. Then summer vacation turned into fall. Then the next summer, I'm like, yeah, I'm going to do another- I like this. I'm enjoying this. I eventually came up with a label for it, which I called hibernation. I hibernated for a couple of years. Then when David Cohen came back as Techstars’ CEO about 15 months ago or so, I told him, hey, David, I'll engage really deeply to help you with everything going on around Techstars, but I don't want to have any public stuff. I'm staying in hibernation. It's like totally cool. Engaged deeply with him on a bunch of stuff. I took the book off the shelf. I just read through the digital version of this mediocre first draft. I'm like, there's good shit in here. Let me see if I can turn this into a good book. I spent the last half of last year doing that. Then when I finished, I felt really like I want to get this book out in the world. Then I decided, if I'm going to put this book out in the world, putting it out in the world and not putting any energy in, it's stupid. I decided to come out of hibernation, but for a finite amount of time. I'm going back into hibernation. At midnight on Halloween, I turn into a pumpkin, just to mix metaphors. Maybe it's for a couple of months, maybe for a couple of years, maybe it's for the duration, I don't know. But it's been fun and gratifying to be involved in this for the last six months. It's really been the last four months when we're doing this, been gratifying and interesting because it's forced me to think about some of these ideas and some of the philosophy and really turn it into something more tangible.
Eric Jorgenson: Yeah, I like the idea of treating it like a season. It's burnout if you try to live your life that way, but I'm glad you're out of hibernation, for this conversation, certainly. But I think there's a lot of people that spend their whole lives hiding, hoarding their lessons instead of sharing them. And so, I'm very grateful when people are open with what they've learned. I'm curious, as both a burgeoning author and a burgeoning investor, what the role of books has been in your career as we close this out? I think that's a fun way to tie it all together. You've written a lot of books. You've done a ton of investing, started multiple funds, started a fund of funds. How has being an author impacted your investing career and vice versa?
Brad Feld: Books are core to so many things I do. I have been a reader since I was a little kid. I don't know when I first started reading, but young single digits. One of my favorite things to do as a preteen and teen, so go back to your preteen and teen years, one of my favorite things to do was lay on my bed, now I do it on a couch, and read. I like to read all kinds of stuff. I like to read science fiction, I like to read fiction, I like to read non-fiction. I used to love to read biographies. Now I read Wikipedia. Every now and then I'll read a biography if I'm really interested in the person. I love to read stuff that I know nothing about, whether it's philosophy or science or whatever. I like to read things from people I know, especially friends. I try not to get stuck in ruts. So I realized, for example, that the science fiction that I was reading was all written by men. At some point, I realized there weren’t that many, when I realized that there weren't that many women who wrote science fiction, when you ran into it, it was more fantasy, but all of a sudden there were some women, really amazing women, writing science fiction. I'm like, you know what, I'm going to not for a while read science fiction from men. I'm just going to read from women. It was interesting to have the shift. I try to be all over the place in terms of what I cover. For people that are interested in what I read, I log it all on Goodreads. Pay no attention to my stars. My stars are five stars if I finished a book, four stars if I started skimming the book, and three stars if I didn't finish the book. Because I think the star system is useless, so I just use it for myself. As a writer, the inverse of it is I figured out a while ago, I started blogging in 2004, my wife Amy is also a writer. So words really are like a central part of a lot of what we do. And of course, I write a lot of emails as a professional investor and all the work I've done. But I started writing, and at some point, I realized that I love to write in the same way I love to read. And for me, idea processing happens while I'm reading and writing, not while I'm talking, not while I'm listening. So listening and talking is what I like to describe as idea reinforcement. So it solidifies the ideas that I have. If it's a new idea and the first time I run into it as a lecture, it's really hard for me. If somebody has PowerPoint slides up on the screen or slides up on the screen and they have words on them and they're talking, I can't do both. I have to either listen or I have to read the words. So, I realized that at some point. I'm like, wow, the writing is connected. Then there's a through line all the way back to when I wrote software. I loved writing software, loved it. As a hobby, I'm about to turn 60, as a hobby, I'm doing it again. So, I'm now writing software again, which is just a blast, especially with contemporary tooling and using AI as essentially a pair programmer. I think a lot of people talk about it as AI agents and vibe coding, and it's really, it's analogous to me as having a pair programming setup where there's two people in front of one computer and one person happens to have their fingers on the keys, and one person's saying, this is what we should do next, and reading and looking at it all, and the AI is actually the one with the keys, and they type a lot faster than I type. And they get a lot- they get plenty of things wrong, but they get a lot of things right a lot faster than I'm going to get them right. All of these things are linked. So, reading and writing, whether writing is non-fiction, fiction, blog posts, code, and reading for me are a broad arc around learning and creating. And so, they're very interconnected in that. The talking and listening is not that part of learning for me. It's the reinforcing and solidifying and knocking the edges off some of the ideas. The other thing, Amy and I, we don't have kids. Going back to when I was a kid, one of my favorite things to do with Amy is both of us lay on our own separate couches and read. Many evenings, especially as we're getting older and becoming less social or maybe more antisocial, more and more of our evenings, having had a lifetime supply of fancy restaurants, I never have to go to a fancy restaurant again. I've had enough. I am happy to every now and then, but it's not core and central. I love the idea of just laying on a couch and reading for a couple of hours until I get tired and then going to sleep. These things overlap, and I maybe end with this idea of books, the arc of creating books, which of course now with what you're doing on a daily basis with Scribe, the idea of being with other people who go through the creation process. If you've never written a book, this won't mean anything to you. If you've written a book, it's really fucking hard. No matter how many you've done, it's still really fucking hard. Now the production of it's... like there's parts of it that are not... like starting with nothing and making something that actually is any good is really hard.
Eric Jorgenson: And having the confidence to put it out, even if you think it's good, you're just afraid other people won't.
Brad Feld: Yeah. Okay, great. So now you wrote the book. Now what? And there's a whole bunch of stuff to do. Like, wow, that's a lot. So, like if somebody says, are you making money off your books? It doesn't matter. That's not why you do it. You do it for other reasons. People have very clear reasons. Sure, of course, some people make money off books, and yeah, I have made some money off some of the books like Venture Deals, which has been a hugely successful book. I've made some money. It's not relative to the other things I could have spent the time on, probably not. A lot of people create books as a platform for whatever it is they do. A lot of people write books for ego reasons. For me, I write books to understand better an idea and work out the idea. I write blog posts to work out an idea. Not every blog post is this deep intellectual work out an idea. A lot of blog posts that I write are crappy and stupid. Some of them are fluffy and fun. Some of them don't make any sense. A lot of them have a nugget or two that I can then keep pulling out and teasing on. For me, writing in public has been always more fun than writing in private. I've tried doing it in private. It's not as satisfying to me, partly because it doesn't feel as committed. For me, when I write in private, I’m kind of like eh. When I write in public, there's a little different piece for me that somehow it doesn't make me try to get it better, but it makes me think a little harder about the idea.
Eric Jorgenson: Yeah, and it gives you surface area to create new relationships and test those ideas and refine them and find your people based on them. It's rewarding.
Brad Feld: Well, that's such a great comment. The blog post I wrote today was about reading some books over the weekend from some friends. I really love reading books from friends. I read a lot of books before they get published. Whenever a friend publishes a book, I buy a copy, I read it, I try to always... I put up my five stars next to their name on Goodreads and Amazon on the review because all authors love more reviews. But in the essence of it, it is a different layer of connection. You and I don't have a super deep relationship, but when we show up in the same place, it's a little different because we've both written books and I've written a book on your platform before you owned the platform, so I wrote a book on an old version of Scribe. I know what matters to you. When I talk to Ryan Holiday, I know what matters to him. One of my business partners at Foundry, his wife, Greeley Sachs, created a bookstore, owns a bookstore in Longmont. You don't do that unless you love books. If you love books, that's cool. That's a category. By the way, anybody listening that writes books, has written books, loves books, wants to talk to somebody else about books, brad@feld.com. Send me a note. I love people who write books. See if I'm full of shit or not that I read a lot. You don't have to send me your books. Send me the link to your book and I'll buy it and then I'll send you the receipt to show you that I actually buy books from people that I know. Again, it's just woven into the fabric. It helps me think and be in a way that's satisfying. Maybe I'll end with, I probably should have the history, but the Gutenberg Press changed the world. That was 1,400, some 1,500, 600 years ago, 700 years ago, and people said, books will be obsolete, whatever. Maybe, I don't know. AIs will take over. Okay, whatever. I don't care. I got somewhere between a day left and 30 years left on this planet. I think books are going to matter until I expire. If they stop mattering before I expire, okay, well, that's life. But I'm going to let it be a joyful part of mine until I expire.
Eric Jorgenson: Thank you. Thank you so much for taking the time, sharing your story, sharing stories of Len, all the sharing that you do and all the things that you founded that help other people find their path and for the inspiration to be ourselves. I appreciate you very much.
Brad Feld: Thanks for having me, Eric, and thanks for being you and doing everything you're doing at Scribe. It's great.
Eric Jorgenson: Take care.