Leap Academy with Ilana Golan - Techstars Co-Founder, Brad Feld: How to Find Meaning While Achieving Success | E126

Episode Date: September 23, 2025

Despite outward success, Brad Feld struggled with depression, exhaustion, and feelings of emptiness. For years, he hid these challenges while relentlessly pushing forward as an entrepreneur. It wasn��t until his 40s, after seeking therapy and confronting his mental health, that Brad realized success wasn’t just about building companies, but about managing the emotional toll of entrepreneurship. Today, as the co-founder of Techstars and Foundry Group, he leads with a harmonious approach to work and life. In this episode, Brad joins Ilana to share the lessons he learned from early failures, why every successful founder faces ‘near-death moments’, and the mental health practices that helped him find joy again. Brad Feld is a venture capitalist, entrepreneur, and co-founder of Techstars, one of the world’s leading startup accelerators. He is also the co-founder of two venture capital firms, Foundry Group and Mobius Venture Capital. In this episode, Ilana and Brad discuss: (00:00) Introduction (01:07) Growing Up in Dallas and Discovering Computers (07:29) MIT Years and Early Startup Failures (14:17) Why Every Startup Faces a Near-Death Experience (16:54) Battling Fear, Shame, and Depression in His Twenties (26:52) Breaking Down at 47 Despite “Having It All” (29:05) Brad’s Practical Steps for Rediscovering Joy (41:54) The Random Day Experiment and Birth of Techstars (52:47) Writing Venture Deals, Startup Communities, and Give First (59:26) Coming Out of “Hibernation” to Write His Last Non-Fiction (1:13:39) Work-Life Balance vs. Work-Life Harmony Brad Feld is a venture capitalist, entrepreneur, and co-founder of Techstars, one of the world’s leading startup accelerators. He is also the co-founder of two venture capital firms, Foundry Group and Mobius Venture Capital. Brad is the author of nine books, including Venture Deals, Startup Communities, and Give First. Through his books, investments, and philosophy of “give first,” Brad has become a mentor to thousands of entrepreneurs navigating the brutal highs and lows of building a business. Connect with Brad:  Brad’s Website: feld.com Brad’s LinkedIn: linkedin.com/in/bfeld  Resources Mentioned Brad’s Book, Give First: The Power of Mentorship: https://www.amazon.com/dp/1646871324  Brad’s Book, Startup Communities: Building an Entrepreneurial Ecosystem in Your City: https://www.amazon.com/dp/1118441540  Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist by Brad Feld and Jason Mendelson: https://www.amazon.com/dp/1118443616  Reboot: Leadership and the Art of Growing Up by Jerry Colonna: https://www.amazon.com/dp/0062749536 Leap Academy Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.Check out our free training today at https://bit.ly/leap--free-training

Wow, this show is going to be incredible. So buckle up, and I'm sure you're going to enjoy it. But before we get started, I want to ask you for a favor. See, it's really, really important for me to help millions of people elevate their career, fast-track to leadership, land dream rules, jump to entrepreneurship, or create portfolio careers. And this podcast is all about enabling this for millions of people to see a map of what it actually takes for big leaders to reach success. So subscribe and download.

never missed it. Plus, it really, really helps me continue to bring amazing guests. Okay? So, let's dive in. I don't need any more money. I don't need any more success. My business was successful. I got very, very depressed. Redfeld is a trade blazer in the startup world. He co-founded two venture capital firms, Foundry Group and Mobius Venture Capital, as well as multiple companies, including tech stars. Every company I've ever been involved in had a near-death experience. The way a business is, It's just a hypothesis. And most of the experiments fail. So you learn from the hypothesis, you learn from the experiment that failed, you create a new hypothesis, you run a new experiment.

It probably fails again. Every now and then, the experiment succeeds. And when it succeeds, you do a lot more of that stuff. You can be very functional as a business person, as a founder, and you can be really miserable. For me, depression is total and complete absence of joy. It's not that I can't function, but there's just a person. no joy in anything. Was there like a moment that is just like, I have to take care of this? There were a couple of things that intersected pretty quickly with each other. One is,

So today I get to speak to somebody that is very dear to my heart. I want you to lean in. It's going to be an incredible conversation. Breadfell. is a trade blazer in the startup world. He co-founded two venture capital firms, Foundry Group and Mobius Venture Capital, as well as multiple companies, including tech stars. One of the most influential startup excelors in the world. He's also an investor in companies like Zynga and Fitbit. He's also an author of some of the most prominent books for entrepreneurs,

including venture deals as well as startup communities and his recent give first. Brad, so great to have you on the show. Alana, awesome to be here. Oh, so fun. So we are going to take you back in time, and I want you to kind of take me through the MIT life. And you, you know, you kind of grew up and somehow dove into technology and entrepreneurship in a really young age. Why? I grew up in Dallas, Texas, and I never really fought very much about anything other than entrepreneurship.

And the reason I say that is the path for me was in my teenage years, When I was a teenager, I got interested in computers around age 12. And this would have been 1977. We barely knew what computers were. Why? I don't know. I have no idea. Like, I really don't.

I was a nerdy kid. I had some friends that were nerdy kids. You know, Dallas is where Texas Instruments was headquartered. And so there was a computer people around some of my friend's parents maybe. My uncle, a guy named Charlie Feld, who is my dad's younger brother, who I'm really close, with essentially created the idea of a chief information officer in the 1970s and 80s. He worked at Frito Lay. And so, you know, my introduction to computers were through Charlie.

The very first time I sat in front of a computer was in a data center in downtown Dallas that Frito Lay had in front of a green screen terminal connected to some mainframe computer. And he gave me a book. It was a black book with a red label on it called, and the label was a programming language. and the language is a programming language called APL, which was the acronym for a programming language, which if anybody's a programmer

from a long time ago, it's one of the weirdest programming languages that existed, but it's 12 like I'm sitting all day on a Saturday, you know, type and into this thing. So that kind of got me into it. For my bar mitzvah, I got an Apple II computer very early and just, I was just fascinated with

software. I was not a hardware guy. I was a software guy. And, you know, at that stage, you had to like be okay, with the hardware, so you had to sort of mess around with it. But that was like my teenage years. Now, I was a, you know, I was a nerdy kid, but I was also, I ran track. And, you know, sort of a, our social group in Dallas was a pretty good social group. Like, it was, you know, the, in high school, junior high school, high school, like the smart

kids, but the smart kids who also crossed over and were kind of quasi-athletic. I know, which is a very weird combination. We'll also talk about the marathon later. But, I mean, it's like, that's a weird combination. Dallas, Texas, like football was a huge thing. None of us were into football. But, you know, I played tennis. I played soccer. I went running. I got into track. I went to MIT, not for any grand plan. I went because the girl I liked in seventh grade, her name was Karen. And to the extent that you can have boyfriend, girlfriend, in seventh grade, Karen really wanted to go to MIT. And her dad was a computer guy, too. Her dad worked for a company called National Semiconductor. So he had like a, if people were remember the Fairchild video game thing. He had like one of the very video games. I remember playing asteroids or not asteroids.

Space invaders. Oh, yeah. So, like, all of that time period, I was a kid, right, as that stuff was developing. And so she wanted to go to MIT. I didn't really think very hard about where I wanted to go to school. I applied to MIT early admission, got in, and threw away all my other college application. So I didn't apply anywhere else. I'd never been to MIT.

I just had this, you know, like, what's going to be? I never really thought that I would not live in Texas. So when I went to school in Boston, even my freshman year, I was still like very proud of my cowboy boots. I'm very proud of Dallas. And Austin was not quite a foreign country to me, but it felt pretty foreign to me. My wife, Amy now, who's from Alaska, went to school at Wellesley College in Boston. That's where we met.

And she actually describes living in Boston and going to school in Boston. Boston as basically being in a foreign country that speaks English compared to Alaska. Oh, compared to Alaska. Okay. And she also tells me that whenever I talk about Texas being, you know, significant, she would say, well, if you cut Alaska and half, Texas is now the third largest state in the United States. And so we had lots of jokes about that. But I went, I went to Boston. Within a year, you know, I was pretty deep into a bunch of different things at MIT. And the word entrepreneurship didn't exist, into computers and into, you know, business stuff. My senior year of high school,

I worked for a husband and wife software company called Petcom, and I learned two very important things. One was that they paid me by the hour, 10 bucks an hour. So I learned if I worked 80 hours a week, I made twice as much money as if I worked 40 hours a week. But more importantly, they paid me a royalty on all the software that I wrote. I wrote two products that they sold commercially, their company sold commercially. It was in the oil and gas business. One was for something called well log analysis. And the other was economic analysis of oil and gas wells and what they produce and the money to make over time. And it was in the oil boom still in 1982, 83 in Texas was a huge boom. And then there was a huge bust in 84, 85. And so for the first year or two,

I was the first employee. I wrote these two products for them. They grew to 20, 25 people, and then the bust happened, and they shrunk back down to the husband and wife team. And so I had this very early entrepreneurial experience. Wow.

Chris and Aves were their names. So again, I got not just my playing with the computers, but also building real software. But they paid me a 5% royalty on the software that I wrote. So I'm in college, and I get checks. I was still working part-time for them as a freshman. I get checks in the mail that would have, you know, I worked for him 15 hours this month, and so I get 150 bucks for the

$10 an hour they're paying me. And then I get $1,500 for the royalty. And then one month, I got, you know, $2,500 for the royalties. And then the month I remember so meaningfully, because it would probably really stuck in my head was I got over, a little bit over $10,000 one month, which was a mind-blowing amount of money for, you know, a freshman in college in 1980, 83, 84, I took across the street from where I lived was a Chinese restaurant that we went to all the time called the Mandarin. I took my entire fraternity to the Mandarin for lunch. For dinner, I can't remember which one. And at the end, I still had $8,000 left over. It gave me this taste, right, very early on of this entrepreneurial. Yeah, and so I never really

thought of working for somebody. I never really thought of, you know, going and getting a job, like at the time, graduating, you know, the seniors that would graduate, you know, they would get great engineering jobs, sometimes, you know, in Massachusetts, sometimes in California, sometimes in Oregon, sometimes in other places. You know, when people broke $30,000 a year, that was a huge number, kind of looked at it, and I'm like, yeah, whatever. Like, there wasn't, there wasn't a pull towards that as a path. Wow, that's incredible. And you did found, like, failed technologies still. in school, I think? What was it?

I found it that in school. So Felt Technologies, I put the official start date when I was a senior because a partner of mine, Dave Jilk, joined me. He was a senior when I was a freshman. So he'd already left. He was working for a startup that ultimately went public. But then he and I joined up. A couple of years prior, I was using that to do consulting for petcom and for a few other

companies. is that. But Felt Technologies was actually the first successful company I started, but it was the third company I started. Oh. The first one, I started as a freshman with three other friends, including Dave. Dave was one, a guy, Andy Mina was one, a guy Samir Gandhi, who's been an extremely successful venture capitalist now at Excel. The four of us started a company called Mark Gell Software. And it was the year the Mac came out. And we had this idea, to write a piece of software. We knew what the Mac was going to be.

It was going to have a graphical thing. And you're going to be able to do stuff with this graphical user interface. And so our idea was we were going to make a piece of software that was like a grid with X and Y columns and little squares. Because spreadsheet, people knew what a spreadsheet was. And you were going to add your numbers into it. And because it was graphical, you could then

make graphs out of the numbers in the spreadsheet. Like a separate product. I think by this, there were a couple of things like Harvard graphics or something where you could enter numbers into a thing and make tables, but it was really lousy. And we were going to have this be on the Mac. And to make software on the Mac at the time, you had to actually get a Lisa, which was another Apple computer that was ill-fated.

But it was their first graphical user interface computer. You programmed on the Lisa and spit out floppy disks and, you know, like this whole torturous process. Wow. What year is this? 1984, you take the little disk, you stick it in the map. Mac, and the very first thing that happens almost every time is a little bomb shows up in the middle of the screen is real TV. And we're trying to do this while we're, you know, freshman, Dave was a senior

and he was finishing up. We were freshman. We just, we were unsuccessful. It was a disaster. And of course, when the Mac came out, there was this product called Excel from this company Microsoft that thought it was, that thing we were talking about doing. So that was, that didn't work. But take me there. Take me there for a second, because it's the first failure, right? Like, I feel like for somebody that, I mean, I'm sure you ticked a lot of boxes of success in MIT, like to get to MIT, et cetera. Like, does it feel like failure? Did it feel like, oh, well, like, like, because you were young? Or what did it feel like? It felt like failure. Yeah, it was hard. I mean, it was the excitement on the front end. And I found, um, I found a box full of a bunch of our old

Martin Gale stuff a year or so ago and some storage thing that we had. And I look through it. Like, you know, the letters that we, the memos that we wrote to each other and like the vision memo that we had and some other things. And it was really pretty profound to think of like a 17, 18 year olds sitting around talking about the stuff. Again, today it's not that different. It's not that unusual in 1983. It was a big deal then. Weird. I mean, that was not like the norm. And so it was exciting and it was visible. And we lived in the same fraternity with, you know, there were 60 of us. And everybody knew about it and people were talking about these different things. And this was a moment in time, right? Like, again, Lotus 1-2-3 was getting started in Boston at this time, or maybe it was

already started and really kind of accelerating. You know, there were a bunch of companies in the area that were PC companies. Actually, Lotus was pretty far along at this point. So that culture was already there, but it wasn't like, you didn't really understand it. It wasn't woven as a 18-year-old. Like, it was weird. It was different. But even then, you decided to continue as entrepreneurship, you decided that this is not the time to hang the towel and go to work. No, the failure was interesting because it was navigating through, like I say it was visible, like it was visible to our friends, but it wasn't like we had closure on it in the end. What ended up happening was we did sell all the equipment that we had and we did

find a customer that paid us some money to write some software for them. And we had one investor that had, we only had one investor. He'd given us $10,000 because we needed to buy some stuff. And we gave him back $7,000. So while it was a failure, we kind of gave him back $0.70 on the dollar. Of course, he didn't care one way or the other. But the emotional experience of going through this thing and then having to be done with it, that was powerful. I did another company a year later that had kind of a similar ending. It was with a different set of people. And we built a product. And it was a really cool product that we built to do. do this thing called cephalographic analysis. And the reason that nobody, you say, what's

cephalographic analysis? We had one customer. It was a person who told us that this was important. He was a Facebook surgeon at Louisiana State University that somehow we found randomly, the guy that was my partner that was actually on more of the business than I, I was the developer. He found all this stuff. We wrote this software. It worked. It did pretty good stuff. And we sold exactly zero more copies of the software because there was no argument for nobody cared this is not a thing and that was another really powerful lesson early on which was you know not not even about knowing what you're going to do in advance i did i care about cephalographic analysis not really you know was it a cool piece of software right yeah it was kind of cool to work on with you know the other guy i worked on a

guy named John Dr. Koffler worked on it with me. He actually wrote all the hard stuff. I wrote the easy stuff. But, you know, same thing. Like, okay, this is hard. This is not like, you know, you just do it. And it just magically works. It's like, yeah, this is going to be a grind. And I appreciate your sharing actually these, right? Because, again, I think sometimes we tend to look at somebody like you and say, oh, it's easy for Brad. But for me, it's really, really hard. Right? Like, it's just so easy to look at kind of where you are. Yeah, I think any founder, no matter where and what age they are, maybe there's some edge cases, but I think anybody who says this, yeah, it was easy, it's full of shit. I agree. It's just, it's not easy. And, you know, every company I've ever been involved in that was a success. So I should say more simply, every company I've ever been involved in had a near-death experience. A bunch of them died. Yeah, a bunch of them. Yeah.

And all the successful ones had at least one near-death experience. Really, like that moment where you're like, this thing is over. This is not going to make it. Like something happened. It could be that the company was doing really well. And then, you know, long list of things. But, you know, I think that early experience for me, I couldn't say it when I was in my early 20s or even probably in my 30s.

Today, I can say it very comfortably. The way a business is, a startup, it's just. a hypothesis and you then run an experiment around your hypothesis and most of the experiments will fail yeah so you learn from the hypothesis you learn from the experiment that failed you create a new hypothesis you run a new experiment it probably fails again every now and then the experiment succeeds and when it succeeds you do a lot more of that stuff but it's useful to know that it doesn't just doing more of that stuff forever doesn't necessarily work That's not going to work.

The hypotheses, and some of the experiments that work for a while don't work anymore. I don't know, maybe you can hear it my voice. I was fascinated by this process, and even in the things that didn't work, when the experiments failed or when the thing was hard, and it wasn't always like I had a good attitude about it, like there was a long stretch of time where the struggles were a real challenge for me to understand how to think about them. as I've gotten older, I understand that it's just part of the experience. And it's a fascinating part of the experience if you're willing to learn about the thing and about you. Tell me more about that because I think, first of all, when you're in that near-death experience, you know, for those listening and not to what we're talking about is sometimes it is so freaking hard that you can't breathe. Like you literally feel like this is going to die and kind of. together was your shame and your embarrassed, right? When that happens, how do you continue and how do you

still fall in love with the process instead of giving up? Yeah, well, fear and shame are really good words. And there are different emotions in the context of it. So we'll play with that first, which is, I think fear comes from lots of different places, including one's own internal understanding of oneself. And, you know, a lot of people are driven by fear in terms of their behavior. A lot of people are driven by achievement. A lot of people are driven by learning. Like, there's different things that drive us. And sort of fundamentally as a species, right? Probably everybody that's listening knows the fight or flight response. And, you know, when you feel threatened, you know, either you attack back or you run away. And it's very, very hard to evolve. It evolves the wrong words. It's

hard to change your reaction to those situations because of evolution, of how it's sort of wired into our self as a species. Shame is a different emotion that has similar characteristics where shame creates a lot of behavior, some positive, some negative. And, you know, one of the things that I think early on that was very hard for me is when I was a teenager, I didn't understand what was going on physiologically. And even as a young adult, early 20s, I didn't understand what's going on physiologically. But in my mid-20s, I started to understand it. And what happened, you know, I would kind of, you know, describe myself as a classic American Jewish kid, put whatever cliche you want on.

that. But I was anxious and my anxiety was a positive motivator in some cases it motivated me to get stuff done, but it was also a burden. But I didn't understand like what any of it meant or how it fit together and I didn't know where it came from and I didn't understand what, you know, how much of it was biological versus environmental versus, you know, what I grew up with. And I was very fortunate. My parents are still around, but I'm very, very close to them. But But everyone that's a child has experiences from their parents that impact in their environment that impact on these things. In my mid-20s, I had a very, very deep depression.

I had a very deep depression at the confluence of three things. One was I dropped out of a PhD program. I like to say I got kicked out. I was a terrible PhD student. So I was running my business. My business was successful. It was doing well, but, you know, like I was just phoning it in for being a PhD student, and I had no business being in that program.

So, you know, MIT likes to say that they gave me a leave of absence. I like to say it was like a bouncer at the bar, like picked me up and hauled me and I deserve that. So that was a very public failure because up to that point, I was this very smart kid that very young age achieved a lot of stuff intellectually, including it at this place called MIT. And I was ambitious. Like, I wanted to achieve it. It wasn't like I was driven. Like, it was very positively reaffirming to me.

Second, I got married to my high school girlfriend, not Amy. And we had a long-distance relationship in college. And then, you know, we really only were living together after we got married right after college. You know, we should have never gotten married. We didn't have kids. So it was more like a young breakup in your early, you know, 23, 24. We had like that boom, that big breakup that you had. But that was a tough one for me for lots of reasons, including a bunch of internal reasons about how I had thought about relationship and marriage and, you know, one of my weaknesses at that time, I would say that translated into a lot of behavior that was successful, but it was a weakness, was I felt an overly involved sense of responsibility for things that I shouldn't be responsible for.

And that was just my nature, but it, again, in some places, very helpful, but in some places it's harmful. And then the last was, while my business was doing well, I was pretty bored. Yeah. I was bored because the business wasn't really changing that much. My partner and I were had a business. It was about 20 people. It was making plenty of money. It was successful. Made money every month on the bottom line. You know, like, it wasn't like I, I'm put on planet Earth to do this thing. Yeah. I didn't have that feeling. I had the feeling of like, okay, I got to get up.

I got to go do my work again. I got to go find another customer. Okay, we've got to solve these problems. It was interesting, but it wasn't stimulating. And my partner, Dave, I think, felt the same way. So neither one of us was like lifting each other up. So these three things collided. I got very, very depressed.

I was very functional. I was able to show up each day and go to work. I was able to do a reasonable job of my work. If you knew me well, you might say, eh, he seems a little off, he seems a little tired, seems a little flat. Those would be the words. I would get done at the end of the day, and I would just lay on the couch and stare at the ceiling. I mean, total, and for me, depression is total and complete absence of joy.

It's not that I can't function, but there's just no joy in anything. And I got lucky. My doctoral advisor connected me with his therapist, his psychiatrist, and I started therapy, And it was a time frame, early 90s, late 80s, early 90s, a lot of stuff wasn't well understood. And the particular diagnosis I got was obsessive compulsive disorder, classic anxiety disorder. But in 1990, nobody had any idea what to do or how to treat it, except for a few people. And one of them happened to be this psychiatrist who was also at Harvard and did childhood stuff. He specialized in kids and he specialized in kids that had anxiety disorders and OCD was worried.

I just got lucky, right? Because I could have gotten like anything. And what happened was even just having a label for me was helpful. It's like I didn't know what the answer was, but I'm like, oh, this way I'm feeling, which feels awful, and I don't like it. And I'm scared. I'm not going to feel differently. Okay, I got it. There's a label. Like there's a thing. And okay, I can work on this. The reason I say that is if you map that to the comments you made about fear, you know, shame. By the way, during this period of time, I was incredibly ashamed of being depressed, of going to a psychiatrist. I took Prozac of taking medication. Like these things, I was incredibly ashamed of it.

So I kept this stuff inside. I didn't share with anybody except my then business partner, Dave, and now wife, Amy, who eventually my girlfriend and then wife. but like nobody else, which is also a problem in these kinds of cycles. And so one of the things at that point, like if I think about it, like you can be very functional as a business person, as a founder, as a CEO, as a leader, and you can be really miserable. Right. And that misery, even if it's internal, can extend, come out in lots of different ways. It can come out in hurting other people.

it can come out in dominance, they can come out in anger, it can come out in control. Drinking, whatever, yeah. All kinds of, you know, self-medication, whatever. And for me, in my 20s, I had like one wave of working through this. And then in my late 40s, having now been very successful at a number of things, including at this time period, this was 2013, most of the external measures in my world were going great. If you looked at things like my business,

the venture fund I was part of Foundry, was doing great, a number of the companies I was involved in doing great. What happened was in 2013, again, age 47, and you know, you think about men, this idea of a midlife crisis is kind of a real thing. And for me, I wouldn't call it a midlife crisis. What I got very depressed. Again, very functional in the context of work.

This time, I had a different experience with therapy. I went back into therapy with a different person. I did 10 years. And this time, I'm like, I'm 47. I'm going to figure this out now. Time to understand Planet Brad and understand what this means in the context of an adult who's had success, who, is in a good place, is healthy and wants to spend time on planet Earth in a place that's

joyful, not in a place that has absence of joy. And one of the things that that link back to, that's really powerful, is I had to work through understanding what actually mattered to me in the context of all of the things that up to the age of 47 I had been doing, but that I had never really understood why they mattered. If you're feeling stuck, underpaid, or unappreciated, or you're simply ready to take your career in life to the next level, I have the perfect solution for you. We have a program that helps you fast track and leap your reputation and career. Become the best version of yourself. Get the dream role you deserve, move up to leadership, jump to entrepreneurship, or even build a

portfolio career. This program helps hundreds a year, and it will help you gain the income, influence, and impact that will transform the second part of your life. Watch our free training today at leapacademy.com slash free hyphen training. The link is in the show notes. Now back to the show. Is it just it? That's so powerful, Brad. I want to take you there. I want you to go deeper there with me because I think the worst situation is not necessarily a bad career, because in a bad career, everything screams at you, fix it, fix it, fix it, it's many times it's the good career that isn't yours. It's the path that you're climbing on this ladder, but it's not necessarily the ladder that is the right ladder for you, right? And it's like, there's usually like a moment where

you're like, oh my God, I need to fix it. Was there like a moment that is just like, I have to take care of this? Yeah, I think there were a couple things that intersected pretty quickly with each other. One is life is this endless series of crisis. I mean, It's cliche, but it just is. And, you know, when I was in my 30s, a friend of mine who had a kid that was 20, their kid died was an older, older friend. And he said to me, after he processed it, he says, you know, Brad, life is a fatal disease, right? And like, you know, it's heavy, but it is. Like, you know, we grow old, we die. You know, things don't work as expected, as planned. We all have obsessions and compulsions, but you're trying to use the linkage between them

to control what's going on in an irrational way. If I touch this door handle a certain number of times before I leave my house, my mother won't die. Like totally irrational, disconnected, have nothing to do with each other things. And your brain's doing that all day long to try to manage your own anxiety. And so one thing for me in this moment was,

fortunately I had not just great support of Amy, but several other close friends. A guy named Jerry Colonna would be in the mix here who were incredibly, like, in the moment, helpful. My business partners, by the way, at Foundry were also fantastic, Seth, Bryant, and Jason at the time where I just said, here's what's going on. And they're like, we got you.

You know, and I, you know, I said, I'm functional, but I just want you know how I feel. And they're like, it's, we understand. You know, we're here for you. This time around, number one, I just didn't want to feel this way. And so I wanted to get to the root cause of it and understand what was going on. Second, Amy, the only thing she really cared about was that I was taking action. She was totally fine with me being depressed as long as I was depressed. But if I wasn't taking action to understand myself better, that was a problem.

So I did a bunch of tactical things right away. I stopped drinking. I stopped using an alarm clock. Turns out I was exhausted physiologically. So without alarm clock, I was sleeping 11, 12 hours a night every night. Like, you think that pretty quickly you're like, oh, I see. You know, this bullshit of I fall asleep on planes and so I can just fly all over the country all the time. I did that. Guilty stars. No. It doesn't work.

Not getting extra. Right. And so I'm wearing myself. So like a bunch of things like I started doing something on Saturday called Digital Sabbath. I, you know, I'm not religious. But I, you know, strong Jewish identity. I'm like, I know a whole bunch of Jewish people that are very successful and don't work on Saturdays. I'm not working on Saturdays anymore. And so Friday night to Sunday morning. I just. No electronics. Turn them off. Do I do that religiously? No, I don't do it religiously. But, you know, I just, I changed that mode. Tactical things, but then, like, go deep. Understand what's at the root of these things and what's causing what is not a helpful function and not helpful behavior, which in my case, you know, was linked to things like taking responsibility for things I don't need to be responsible for having no governor at all on my physiological effort, like literally not saying enough. I need a break. I need to give myself some time. I use running as a release valve for many of these things, but running is not rest. Right. So it's one thing to,

I mean, I love running and I love being lost in the woods, but at the same, I lost in the mountains, but at the same time, like not taking care of yourself, not giving yourself rest, not creating enough detachment from things was a problem. And then one other thing that happened was I was really finding myself in this success cycle, but also with the philosophy that I developed in the way I comported myself, which instantiated in this book and give first, because give first is a philosophy. And at this point, I was starting to have language for it. I was calling it give before you get, which is a terrible hashtag. So somebody had tech stars eventually turned it into gift first because much shorter if you only have only 40 characters. But I really, I didn't

know how to put boundaries on what I was doing. And so I was constantly depleting myself against the backdrop of achievement for what purpose. What happens when I step back from all of that, and I'm almost, I'm about turned 60. So, you know, I feel like I went through this experience where I really learned and frankly set myself up comfortably for the third third of life emotionally, whether that lasts, you know, whether I have a day left or 30 years left. We don't know, right? It's indeterminate. But I feel like I understood this set of things that for the 40 years of business and the prior part of my life, I can translate into behaviors that are healthy for me and that are useful and productive for the people I choose to engage with

and who choose to engage with me versus where I was before, where I really didn't have a good handle on that for many, many, many years. And I appreciate your sharing all of this because I think, again, there's still shame around anything mental. I think anxiety, depression, all of this is incredibly common, especially in entrepreneurship. Like, I feel it's so lonely. But then I think there's still, it's not like a wound that you can see in your arm, right? It's like it's something that it's not visible. And when it's not visible, it's hard for us to admit it.

You know, I remember waking up in the middle of the night and feeling like I'm getting a heart attack, right? Like I think sometimes it gets into like, oh my God, I need to do something because I'm going to kill myself. Whatever the negative emotion is that you're describing that one has is so extreme that you almost can't stand it. And lots of people that are not entrepreneurs struggle with that, but entrepreneurs, particularly in moments, there are many moments where you have no way to process what's going on other than to try to feel that. The cliche of the entrepreneur at three o'clock in the morning, lying at bed at night, you know, trying to solve the problems is the nice version of that. We kind of make heroes out of that behavior. It's like that's heroic behavior. And yet it's actually

really not. It's terrifying. It's awful. It's not, you know, it's not what you want and how you can engage with things even when they're not working or relationships or people or the business or whatever in ways that are positive and constructive. And when you look back on, you'll be proud of even if the thing didn't work is very hard. And one of the things, you know, you asked me what were the things that came together at this point in 2013, and one of them was this, which was I wasn't ashamed this time of being depressed. I had enough depressive episodes. I was old enough. I had a couple of friends, Jerry Colonna being one, another one Dave Moran, who was early at Facebook, who had been public about their own struggles with depression. Another person who I think has been incredibly

brave about what he's modeled is a guy named Paul English, very, very successful founder of Kayak as a bipolar disorder, and had let Tracy Kidder, who's a magnificent writer, follow him around for a year or two and write a book. It's called something like, you know, getting hit by a dump truck of money or something like that. And Paul, over time, understanding how his bipolar disorder was both additive, really helpful, but also really hurtful to him and a lot of people. around him and him understanding himself in the context of it. So there were some people that were now very successful talking about it. And I said, you know what? There have been a few founders that have committed suicide in the preceding 12 months. And the tech community does what the tech

community always does with these things, which is, it sort of says, oh, look at this thing. It's horrible. We must do something about it. And then it's like, you know, a dog with a rabbit. Oh, rabbit, squirrel. You know, like, on some other thing. There's like no continuity. of like, let's change something. You know, why, why did these brilliant people decide to take their lives? And kind of my response to it was, you know what, I was already blogging, you know, I've been blogging every day since 2005. I talked about 2004, I talked about all kinds of stuff.

Like, if I don't talk about this, I'm actually hurting myself. Forget about anybody else. I kind of was creating this internal dissonance where I was basically like bullshitting myself. Look over here. Everything's great. Don't worry about this. And then internally, I'm like, I'm just really down. And so I just decided like, you know what?

You know, I'll let it out. And then what happened was kind of wonderful in a weird way. You know, I don't know the number, 100 people that were well-known, many of them well-known entrepreneurs that I didn't know, reached out to me because I showed up in ink magazine and a big expose that Jerry and I did around health and I was blogging about it and a show up in this article and that article. And people would just sort of email me and say, can we talk? I'm like, yeah, sure, you know, because that was my nature.

And for many of them, I was the first person they'd ever talked to. They didn't talk to their significant. It's like they couldn't acknowledge what that was going on. Some people were very helpful. Like they'd work through their own stuff. And so, you know, it wasn't, hey, Brad, let's have a conversation I can fix you. It was, hey, Brad, let's have a conversation. Let me tell you about me and about.

about the stuff I went through, and maybe my experience can be useful to you. And so in a pretty 12-month period, that depressive episode lasts about six months, but about a 12-month period, it helped me coalesce some other ideas around what turned into mentorship that was already in the system with texters,

but this notion of the importance of not telling people the answer, but of giving them stories from your own experience that they could either decide to do something with or to totally ignore. Now, I've learned this in the early 90s in my first company through something called Young Entrepreneurs Organization, now called EO, and a program called Forum that was part of YEO and Young Presidents Organization.

And it's a structured process, a three-hour thing that you do once a month with a confidential group of the same dozen or so people that get together every month that are your peers. and a key part of the process is you don't, a person presents the problem to the group, and the group doesn't respond by saying this is what you should do. The group starts by asking a bunch of clarifying questions.

So you start by asking a bunch of questions to try to get to the root cut. That's a big one. You ask questions. But they're asking questions with a purpose. We've all run into the person in a boardroom or in a meeting. That's just asking questions. They don't go anywhere. You're like, you know, Mr. Socrates is who I call that person. I'm like, just go away. You're not helping here, right? Versus like asking questions with a purpose, trying to get to the root cause. And there's techniques like the five whys and others. And after that process and you sort of people got the stuff on the table through the questions, each person would go around and tell a story from their own experience that they thought related to the issue being discussed. And for me, like those two things.

really clicked in to a lot of the mentorship we were seeing that was effective at TechStars and useful versus ineffective mentorship where a mentor that would show up and say, Alana, you should do this. You should do that. Oh, that's your problem. Here's the solution. That's actually not helpful. And by the way, like 50% of humanity, whenever somebody says you should do this, they immediately go run and try to do the opposite. But if you say, look, here's some data from my own experience. I had this happening in a couple of places, right? One was in this whole experience I was having with mental health and depression and my own exploration. One was happening in tech stars with mentorship. One was happening with my own behavior and how I was engaging

with people. And then as I reflected several of the most influential mentors on me along the way had behaved that way, where they weren't being directed. It was supportive, but it wasn't supportive in the absence of the thing. It was in the presence of the problem I was facing and giving data to help me think through and come up with my own solution. And I love this because I think you're verbalizing to some extent why Leap Academy was successful, right? Because it started from a deep pain, what I started, right? And then it suddenly changes thousands of lives because we're going deeper into this. Because again, I think what you're describing, Brad, and I think the audience and the listeners will really resonate with this, because I think sometimes when we tick all the boxes

of success, it's harder to admit that there's a problem because theoretically we should be grateful, right? I have a beautiful home. I have a beautiful husband and kids and whatever, and I should be just grateful. And the truth is, it was incredibly painful to feel so depressed, right? So, There's a little bit of that that is coming, you know, as well. How do you even ask for help? There's a great talking head song that you made me think of that. I just looked up from the 1980s. This is a regular rotation.

I couldn't remember the name of it. It's called Once in a Lifetime. Do you know this one? Oh, I think so. I'm going to check it out. You may find yourself here. You may find yourself living in a shotgun shack. You may find yourself living in another part of the world.

You may find yourself behind the wheel of a. large automobile, and you may find yourself in a beautiful house, the beautiful wife, and you may ask yourself, well, how did I get here? It sort of relates to this notion of this idea of what does it mean? And if you approach, like, I'm successful, this is great, I'm not going to acknowledge that there's hard shit going on or things I don't like going on, or the other, I'm successful and I'm angry at all these other things. All of it comes back to you, like start with you. Like what's going on with you, not what's going on with everything else?

Well, there's a reason on planes we put our own oxygen mask on, right? I mean, there's a reason. So take me, just a couple more because I want to, like, that kind of ties into your book. Like, you started tech stars from a meeting. Speaking of giving, you liked giving and that became tech stars. Can you share that story? is beautiful. Well, precisely, what I, what I did was as I became more visible and more known, especially in Boulder and in Colorado, everybody wanted to get together with me,

whether they were local or whether they were flying through Colorado or coming to Colorado for any reason. Could be business, could be work, could be relevant to me, could be coming to see you to see their kid, could be going skiing. I started being on the receiving end of this infinite number of emails saying, can we get together for coffee? And at some point, like if I said yes to everything, which was my kind of default mode, I'm a default yes person generally. If I said yes to everything, all I'd ever do is have coffee and go to the bathroom. Like I get nothing done. And so I had to come up with a way to deal with that. And a way I decided to deal with that. And still, I had a deep value of being very accessible. I don't have a gatekeeper. I answer my own emails. I always have.

My email is bradettefeld.com. I'm very easy to find. It's just the way I am. It's a value I like, and it's the way I like to be, and I like to be thought of. I'm sure it feeds some element of myself at this stage of my life. But it's just, it's the grooves in my record are pretty deep around being accessible. And in this context, I'm like, I want to still be accessible, but I can't say yes to all these coffee meetings. So I came up with this idea, and what I did was I started having once a month random day.

And random day for me was 15 minute meetings with anyone who wanted to meet with me. And the way I did it was I created before there were like online calendars and calendally and all that sort of stuff. I created a very simple online calendar on the web. And when somebody would email me, I'd point them to the calendar. And a bunch of people would never get on the calendar because they didn't really want to meet with me. Or what I don't know what their motivation when they didn't know what their motivation was. Eventually what I wanted to do out of each of these 15 minute meetings. I do like 10 to 20 of them in a day, once a month.

And my goal was two things. One, learn one thing for me. And two, figure out one way to help the person so that every meeting I was in, the person would have one thing to be leaving the meeting to be helpful with. I did this for about 10 years, and it was really fun. And a lot of very interesting things came out of it. One of them was tech stars, and it was not at the very beginning of this. It was in the, I've been doing this for a couple of years.

David Cohen, who I didn't know, lived in Boulder, had been a successful founder with his co-founder, David Brown, knew of me. And we had actually, he had made an angel investment, a couple of them, and he and I had made an angel investment in the same company. So we were both angel investors in this company, Solidware. So we wanted to get together with me, and somehow he, you know, he learned about a random day, and he just learned about the calendar. He didn't even reach out to me in advance, and he just signed up. It took about three months, and so we get together, and he's in the middle of my random day, and we sit down, don't know him. He slides a piece of paper across the table to me that, you know, it's a nice little sort of almost

brochure-like thing, and he starts talking kind of in a soft-spoken way, and I said, hey, I can't read and listen at the same time, so let me just read. You know, you clearly put some effort into this. Oh, good, like all the different effects. Hey, if you're in YouTube, there's some bad. We're listening. We just had fireworks go off with whatever hand signals I did. Or maybe I said David Collins.

Oh, who knows? Yeah. And so he said, okay. And I said, I read the thing. And it basically was a description for this thing that became tech stars. It's like, you know, I'm unhappy making angel investments. I'm not really having fun with it. I don't feel like it's engaged enough with the founders.

It's 2006. You know, angel investing is not like this super hot thing that everybody's doing all of a sudden. It's still sort of emerging from the dot. com rebel and he says you know what i want to do is i want to put together a little money uh i want to invest in 10 companies i want to have them all eat together in boulder over the summer for 90 days run a program surround them with some people that are other experienced people to help them and just try to help them get their company started that was the basic idea which evolved into the idea of of a mentor driven accelerator and i said i asked them a couple questions mostly

trying to understand where it was. He says, well, look, I'm putting in $80,000 and my partner, David Brown, is going to put in 50, but he wants somebody else to put in 50 so that he's not just putting in 50 with me. And we kind of want to raise, you know, $200,000 or so, maybe a little bit more, you know, $20,000 times 10 companies plus a little money for like pizza and maybe some office space for the summer or whatever. And I looked at them and I said, look, as long as you're not a flake or a crook, And I can find that out with a couple of emails. Count me in for $50,000. I walked out of the room.

I called a friend of mine, Jared Polis, who's the fourth co-founder, is the punchline, but he was now a governor of Colorado. He was a very successful entrepreneur. And we'd done a few things together. And I called him up. I said, hey, Jared, I'm putting $50,000 into this thing called TechStars. Can I tell you about it? And his response was, Brad, I'm good for $50,000.

What is it? All right? So now, you know, I told him, he's like, that sounds great, let's do it. So I walked back in the room and I told Dave, I said, all right, you're done. Jared, Jared's going to put in 50. Jared who? Jared Polis. Oh, really? And so the four of us started this thing.

And the idea was, it's an experiment, right? It's a startup experiment. We didn't spend years trying to figure out what the market was. We didn't spend a bunch of time doing, you know, diligence on whether it would work or not. We're like, you know, we'll try it for a year and it'll either work or it won't work. And if it doesn't work, it'll be a fun experiment. And if it does work, we'll have investments in 10 companies of which one or two of them might be successful. And worst case, we're going to have a fun time in Boulder for 20 days with a bunch of founders, turned out to be about 25 founders and about 50 mentors, some of whom were local founders, but some of whom were people on the East Coast or the West Coast who were friends who came to Boulder for the summer.

And so that was the instantiation of it. And I describe it that way because it's such a canonical example, like the random day in and of itself is give first, right? I'm just being accessible. The try the experiment. Yes, sure, I invest. It was a transaction. I invested money in it. He invested money in it.

David and Jared invested money in it too. But we sort of all looked at it as let's see what this, if this works or not. And then when we ended up having about 50 minutes. that first year. And most of them were friends of mine, not all of them, but most of them. And the pitch was pretty simple. Hey, we're doing this thing. Will you come and hang out with – and we didn't really have the mentor word yet locked in because mentor wasn't that well used in 2006. So come spend time with them, spend time with these companies, hang out, meet with them, spend a day. You know, and for people coming out of town, I would say, look, I'll take you out

to dinner. We'll hang out. If you want to see other stuff in and around Boulder in Denver, or I'll make other linkages or whatever. And so for most people, they're like, that sounds cool, sure. For a few people, they'd say some version of what's in it for me. And my response would be, you know what? I don't know. Don't worry about it. It's cool.

And off I went to the next person and those people were not involved in the first program. Most of those people after the first program were jealous. For me, reached out, hey, can I do that? Because it was just so much fun. And the other piece of it that's interesting in the origin story that came from this, that's, I think, again, embodied in this idea of give first, is that we had a lot of people from around the country reach out to us, and actually around the world, a few people internationally saying, hey, this tech stars thing's pretty cool, you know, like, can we do a tech stars in Chicago?

Can we do a tech stars in London? Can we do a tech star is in this place? And our response was, we have no idea if this is a good idea. We just don't know. We'll tell you everything we did. We'll give you our documents of how we did it. We'll come, and for a couple of the programs, the one that I remember the most was in Chicago was called Accelerate.

We'll come be mentors if you want and participate in the thing and come to your demo day. And that was the beginning of other accelerators kind of popping up in different places. And there were some other things that we did early on around that. But part of the thing that was really fun in hindsight was we didn't have an ask of those other people. We didn't say, we'll tell you how to do it if you give us this. And a story that comes around is that TechStars had now started to expand into other geographies. We expanded into Boston, Seattle, New York. And we're starting to think about the other cities we want to go into. And I went and had dinner with Troy Hennikoff in Chicago. Troy was the managing director of Accelerate. And we're having

dinner. And I said, hey, Troy, you know, would you ever consider like turning this into Techstar Chicago? And he's like, you know, well, that's kind of fun, like, interesting. Like, let's talk more about it. And what we ended up doing was it became Techstar Chicago. So we just rebranded and became part of the TechStars Network. And now all of a sudden, that's part of what we're doing as we expand. You know, a lot of it came from the relationship that was already developed. It wasn't like this heavy negotiation of what are you going to give me to be part of Techstar Chicago.

And it was, is this an idea or not that makes sense? Yes, this makes sense. Okay, let's go. So, you know, the dynamic of how things come back around, Troy as a dear friend, Techstar Chicago have been hugely successful, both for the investors from Chicago that are investors, but also for TechStars as an investor in the things that it's done. I sort of lay out that landscape as an example of like a different way of approaching the business interactions. Sure, there's still transactional components to them, but it's very much from an inside-out relationship dynamic.

It's, I'm interested in just doing stuff with you. Let's see where it goes. Okay, let's figure out what the parameters are if we need to have parameters. But, you know, for a lot of this stuff, you don't need a parameter. You can just get going. And I love it because even if you look at your books, it was all about give, give, give, right? Like, venture deals were all about giving, right? Like, it's all the things, all the mistakes the founders do, basically, when they don't know what they're doing. So that literally saved me so much because I I had no clue. Like, what is a term? Like, what should I look at? What, you know, like, you guys just spell it out, which is exactly what we need. And startup communities is also, it's like based on everything that you've built and the communities that you've seen and what's important. And I think now you're giving give first, which is essentially that same pattern that is so

symbolic of how you do everything, Brad. You're landing on it really well with those books and with all the other ones I've read. and, you know, for anybody that cares or knows me for a long time, I think that this book give first, which is my ninth nonfiction book, will be my last nonfiction book. So I think I'm, after nine, I think I'm done. It's very interesting as I've, you know, written more books and spent more time, you know, understanding the publishing industry, the good and the bad of it, and understanding why people write books and having lots of people who write their first time books reach out to me and say, I'm writing my first book. And one of my first questions is why. Like, just tell me

why because I'm kind of curious what your motivation is. Of course, for many people writing a book is creating basically the instantiation of a platform that they then can build a consulting or speaking or whatever kind of business around. It's, you know, this is my thing. And it's a revenue generating activity, not as a book. Because books are, you know, if you want to make money. As a funnel. Yeah, don't write. I mean, you might get lucky and make some money if you write a book, but most books don't make any meaningful amount of money in the grand scheme of things. Every The venture deals has been a hugely successful book for its category. Somebody once told me, if you sell more than 5,000 copies of a nonfiction book, you've done well. And my response was,

what the fuck you're talking about? Well, mine is in the making, so I don't want to hear that. No, I'm kidding. The issue is less like, how many books did you sell? And like, what's the reason you did it? Well, for a lot of people, the reason is it's, it is codifying, in a way, a lot of the things you're doing. And that's very valuable for a business. For a lot of people, it's ego. And you really find ego when you ask people like what around this is the you know you pick it a little bit and ego is a bad reason to write a book I think in general because not because it doesn't satisfy your ego because it's really hard there's lots of better ways to satisfy your ego so you know we all

have egos and egos are fine if you want to stoke it don't don't make the book the way you stoke it's very long and audacious and a lot of podcasts Brad but interestingly when when jason and I wrote venture deals, we already had reputations that we had. Sure, it got us exposed to more people, but we didn't write it for deal flow. We didn't write it for our venture business. We didn't write it for money. We didn't write it because we wanted to be speakers about how to do venture deals. We wrote it because it came from a series of blog posts that the two of us wrote together

on my blog three years earlier, that were a function of being incredibly frustrated with the information asymmetry in term sheet negotiations. I mean, we would be constantly as VCs who did lots of terms, we'd be working with entrepreneurs who had lawyers. Some of them were lawyers who were, you know, good venture lawyers, but many of them were not and didn't really know venture, how to do venture deals. And like the opacity of how some of these things worked

and the things that people were negotiating over. And like, I can't tell you the number of times early on about people marking up. like registration rights and changing the registration rights clauses on this you know this doesn't matter like why is this in here and so we decided to understand that and explain it and try to do it in english which i appreciate it very much really de-struck the whole thing so that was like the motivation book and from that that was very it was the second book i wrote but it was very helpful to me because when i wrote startup communities what the motivation for that book

was I was done listening to people say, if you're serious about building a tech company, you should move to the Bay Area. Nothing negative about the Bay Area, but I'm like, look, you can build these companies all over the world, and in fact, you should. And the world needs these things. And people all over the world in all the cities they live in,

people live in cities for lots of reasons. And a lot of them are because they love the city they live in. And the idea that you could be able to start a company anywhere in the world, and you could have a startup community that was vibrant as part of a city anywhere in the world was important to me. And, you know, if you look at that book, you know, it's a book that's anecdotes, it's stories, its examples. It's got a thesis behind it, but the thesis that's behind it is a pretty simple thesis

that at the time was pretty controversial. Like the way I laid out what I called the Boulder thesis and some of the things I said were not the natural ways that people talked about what you had to do to have entrepreneurial ecosystems or innovation clusters or whatever. And I gave voice to founders of doing it a different way. Why did I do that? Well, yeah, okay, there's a link to tech stars because we were doing that stuff with tech stars and expanding. And sure, for me, some of the other things I was doing that I was involved in like startup America at the time, which was a public-private partnership with the Obama administration, was trying to get more startup stuff in different places in the

United States. I was fascinated at the startup weekend, which at this point had become a pretty big thing that was happening all over the place. And I was on the board of it, I think, by now, and supportive of it. And so I had this sort of notion of the importance of codifying it. But as an example, like, you know, I did, I don't know how many talks on startup communities I did in the last couple of years. I did talks for anybody I want to talk about it. I didn't charge money for it. It wasn't a business. It was an evangelism of an idea. I thought was an important idea that I wanted to get it out in the world for people to take and build it.

Whatever they can, yeah, from it. And I own startup communities, trade, you know, TM, you know, it's like, no, kind of the opposite. Will you please start calling these things, startup communities? It wasn't a phrase prior to it. Please use this. Please talk about it way. So we have a common language for doing it. thing that for me was important and exciting and interesting. And the reward, back to give first,

the reward for me, both financially and non-financially have come in many ways that I couldn't have expected on the front end of it. And that's the essence of it. It's you do things because they're interesting, because you think they'll have impact, because you care about them, because you were put on planet Earth now to work on it. And if you do it and you do it, well and you do it in a way that's accessible to others and you don't try to control where it goes the things that come around are wild and wonderful awesome so why give first why sit now that you take all the boxes of success why slave over another book this book had a had a little bit of a bumpy ride so i've been thinking about it for a while and i wrote a draft about three years ago i'll do a draft

kind of by myself. And then I toss it out to 20 people or so and just say, I share a Google Doc. I don't try to control it. And I just say to everybody, just comment, whatever, send me email, leave me voicemails, whatever. But it's kind of just like out to this group. And some people, you know, give me very, very detailed edits and some people just send me back, you know, an email with a couple of thoughts. And what came back from this was a couple of things. One, I kind of jammed together these two ideas of Give First and mentorship. I hadn't really interwoven them, happened before in other books that I've written. So I knew what I need to do to interweave them. But that's a lot of work. It's deconstructing the book, refactoring it, putting it back together

again, adding a lot of connective tissue so it's actually a book. But like, you know, the bones are there, but I got to take it, I got to tear it apart, throw it on the ground and put it back together. The second was people said, Brad, in this book, there's way too much text stars than not enough Brad. And, you know, you talk about mentorship and you talk about telling examples from your own experience to support the point. And you do some of that, but you do too much that's not from your experience, anecdotes and stories that are tangential.

And I took that to heart. And that intersected with a moment in time for me where a couple of different things were happening. This was in the midst of COVID. And I was tired. I was very tired of a bunch of different things. And this was not depressed, fatigue. And I decided, as I thought about it,

about it that instead of finishing the book, I was gonna stick it on the shelf. And I did something else instead, which is I did something that I now have a word for, which is I called I hybridated. And what I did was I just stopped anything public facing. You know, I've been blogging for now 15 plus years, 16, 17 years, I just stopped blogging.

I didn't write a blog post saying, I just stopped blogging now and check back in here. I just stopped. I stopped doing any sort of public anything. I stopped going to public things. I stopped doing video conference, public events. I stopped doing podcasts. I just kind of hibernating.

And what I did was I shifted all of my energy to doing things that were interesting to me in the context of my work. So I still was very busy and very active with my companies and with the things I was involved in. But I just eliminated, I peeled off this public profile and this public engagement. And I shifted from default yes to default no. And I didn't know how long I was going to do that for a summer.

Like at first it was take summer off. And then it was like, you know what? I kind of like this. I'm going to take the winter off. And then it's like, I kind of like this. I'm going to take the spring off. And oh, it's summer again. And it turned into two years of hibernating.

And after that sort of time period, what happened was, David Cohen had left tech stars. He was still at tech stars. He was chair, but we'd hired a CEO to scale tech stars that I would describe the best. The kindest way to describe it is we had our awkward teenage years.

And everyone's been an awkward teenager. We had a year, 15, a year 18. We made a lot of mistakes. We did some stupid things. We heard some people's feelings. We did some good stuff. But we also made some errors. And David had come back as CEO.

And I said to him at the time, I said, look, I'm really enjoying being not having a public profile. I didn't have the hibernation work yet. I said, I'll do anything I can to help you from behind the scenes. Like, I'll do anything inside tech stars with founders, but I just don't want to do anything publicly. And he said, no problem. And, you know, that, we engaged in that. And, you know, about a month in, I took the book off the shelf metaphorically. Like, I went to the Google talk that it was in and I opened it up and I read it. And I actually printed it out and read it. And I like, you know, some good shit in here.

And so I decided I didn't commit to finishing it, but I took the second half of the year last year and I worked on it for about six months. And by the end of the year, by the holidays, I felt like it was really good. Like I'm like, yeah, this is good. And so I talked to Amy a lot about it. I said, look, if I'm going to publish this book and by that point I was starting to say to her, I think this is it. I'm going to start writing fiction and I'm writing software again.

I love to write software. So, you know, I'm playing around with that again. I said, I think this is going to be a real book, and maybe it's the last one. Like, I'm going to come out of hibernation, put some energy into it, and do that for a period of time. And what we did, and she was really helpful in me defining it, is we bounded it. I said, six months. And actually, in hindsight, I wish it was three months instead of six months for a variety of reasons. But six months is fine, and I'm about four months into it.

At Halloween, at mid-day and I'm done. back into hibernation. But what I decided to experience, you know, kind of out of hibernation engagement again with this. So kind of that was the arc of the book. And then there's a why behind that, which is as I wander up to 60 that I'm in what I call the third, we call the third third of life. For Amy and I, it's very much, you know, I said to Jerry Colonna, who I mentioned earlier probably seven years ago he wrote about this episode in his book we were just sitting around talking one afternoon and i said just blurted out you know jerry i'm done striving like i mean i'm not going to get anything i'm not going to accomplish anything but i'm just

like i don't need to like whatever that's i just don't need it i don't want it i don't want to spend time with people i care about i want to work on things i care about i want to do things i care about you know like when somebody says well what impact do you want to have on the world i'm like the world doesn't give a fuck about me. Well, you already made a mark in the world. Like, let's put it in context. Where you want some legacy to be, I don't care him to be dead. You know, I just want to shift out of that kind of thinking.

And I want to, you know, I just want to have the experience of the time I have on this planet. And I want that to be meaningful. It doesn't have to always be joyful. And it's not. I'm going to have things that don't feel good. I'm going to have things that are disappointments. I'm going to have relationships that break. I'm going to have things that fail.

That's part of the experience. I want to experience that for the rest of the time that I have, putting a book out around that in this moment and time, you know, that talks about these values that really is a culmination for me of what I've learned from people like Jerry, from people like Len Fasler, who I bought, you know, bought my first company and passed a few years ago, but was incredibly close. People like my uncle Charlie, my dad's younger brother, who introduced me to computers and was an incredible mentor and still a very close friend. People like Chris and Helena, Aves, we talked about at the very beginning that, you know, I really learned the first founders I worked

with. People like David Cohen, who 20 years ago, we didn't know each other. And, you know, like the level of, I mean, emotional intimacy that we have through the ups and downs of our experience together, completely independent of financial reward, of success, of any of those labels, just like that experience. And I wanted to somehow pull that together in a book that wasn't a memoir, because I don't want to write a memoir, but of course, if you are a mentor, tell me stories from your own experience is very valuable. So there's elements of it.

I didn't want it to be a, you know, you should book because that's not mentorship. And frankly, you know, I like to say people, if you like it, tell all your friends and if you don't like it, throw it away. Don't tell anyone. Like to the extent that people in the same way some of my other books have been impactful on the way people follow their journey, if this is going to be impactful on some people, that's reward enough itself. But I decided if I was going to do it, I was going to do it rather than something else. So that's the why. Oh my God, Brad. This is so powerful because I think we have a lot of listeners and kind of like that late stage career trying to figure out what's next, right?

Like, do I want to keep on going? Do I want to create impact? Do I want to just enjoy life and whatever and drink mojitos on the beach? Like, I think there's a lot of like, what do I want to do next? And how do I see my life, you know, which is a big portion of what we try to help them with. But I think it's not an easy question because there's a lot of options on the table. It's very hard.

And I think that was a lot of the challenge I had at 14. which was I don't need, at 47, I don't need any more money. I don't need any more success. Why am I working 80 hours a week? Why am I flying all over the place all the time? You know, like why? I didn't have an answer. Now, was I required to have an answer? No, but the lack of an answer was the problem. It would be easy to say, well, I'm trying to have an impact on the world or I'm trying to put it down from the universe or I'm trying to whatever the cliche is. Like, why were you put on this planet at this time? What were you put on this planet at this time to work on? What gives you joy and fulfillment. Well, I want to make the world a better place and I feel obligated to do this thing to make the world a better place is not really complete. I think a lot of it is also having no regrets or as little regrets as possible, right? I mean, which is also part of it. And sometimes it is about the fun, the experience. Regret is such a powerful world. It links back to early part of the conversation about fear and shame. I have understood now, and I talk about it in in give first. I understand now what I regret. I didn't when I was 47. I didn't when I was

55. I don't regret anything that I failed out. I don't regret any failures. They're just experiences. I don't regret the hard things that I had to deal with or have to deal with or will have to deal with. I don't I'm not afraid of those things. That's just part of the experience of life. The things I regret, the only real thing I regret, and I would say in business, there's some personal regrets that I would put around responsibility. But in business, My only real regrets are situations where I was passive avoidant. And frankly, in my personal life, too, when I was passive avoidant. And I described passive avoidant really simply, and I separated from being actively avoiding,

which is something that I now choose to do, which I didn't for a long time choose to do. Passive avoidance is you see a problem somewhere, and you understand that there's a problem. And it might be a direct problem that impacts you. It might be an indirect problem. but it's a problem in the sphere of influence of a thing you're involved in. The severity of it could range from not that big a deal to something that could be a really big deal. Passive avoidance is looking at it, acknowledging it, knowing it's there, and then consciously, or sorry, not consciously, of not dealing with it.

Active avoidance is consciously deciding, I'm not going to do anything about that. And in fact, for me, now active avoidance is often saying it out loud. You know what? there's a problem over there. There's a giant pile of dog shit. And I'm not touching it. Not only am I not touching it, I'm not going to go near that corner anymore because there's a giant pool of dog shit in that corner.

And if one of you would like to clean up that pile of dog shit, I'll come to the corner again. But until somebody cleans up that pile of dog shit, I'm out. I'm not just not cleaning it up. Bye. Right? That's active avoidance. Passive avoidance is, eh, stinky, smelly thing in the corner.

I think I probably just wander. over there. That's passive avoidance. And that's what I regret. When I think about the broken relationships I have, when I think about the things that didn't work, when I think about the things that I knew were problems that got worse. It's the passive avoidance is the regret. You weren't intentional about saying yes or no, but you just weren't intentional, period. It's so intentional. And sometimes you have an excuse. I'm too tired. I got too much other stuff to do. It's not really my problem, whatever. But you're sort of avoiding. And oh, by the way, I've cleaned up plenty of piles of dog shit.

Lots of them that weren't mine to clean up, right? But that's different. The inverse of that, which you see over and over again, are people, and it's especially tiresome for me in today's society. You see a style of leadership where people are creating piles of dog shit in the corner and then blaming it on other people. And, you know, it's the inverse of my own value system. And so it's tiresome.

but one of the interesting things about active avoidance versus passive avoidance is that there's some of that that I look at and I'm like, you know what, I'm not going to do anything about that. You know, it's not mine. But you've got to that maturity to say that. Human beings are going to be human beings. People are going to be what they are. Like, I'm not going to solve all of them. I'm going to choose where I'm going to put my energy on the things that I actually think I can have

impact on with people who I want to spend time with and I want to engage with. Like, that kind of thing is interesting, which if you think back to fear and shame and how that impacts a lot of people, especially as you get older, especially as you find yourself in this position where you've had success and relevance. And, well, if I don't keep doing those things, am I going to still be relevant? And that's scary. Are people still going to care about me? Are people still going to want my opinion?

And, you know, like, there's a great peacefulness in saying, I don't care. Like, if nobody thinks any of this stuff is interesting, awesome. Go do your own thing. It's cool. Getting to that place was really hard. And Brad, I loved every minute of this conversation. I think this is like gold, gold, gold, especially because a lot of our people are trying to figure out what's next. How do I create either more or, you know, more something, more balance, more impact, more finance, whatever, more something, right?

What would be the last kind of like question? what would be maybe a tip for your younger self if kind of looking back? I'm going to play with a word that you just use that I would tell my younger self, which is balance. It's true through all of life, but I think especially for younger founders and for my younger self, there's this whole thing about work-life balance, and there's one end of the spectrum where people say,

there's no such thing as work-life balance if you're an entrepreneur. Don't even try to have work-life balance. The other end of the spectrum is this endless search for work-life balance and try to figure out how to navigate all that. Amy and I decided a long time ago to delete the word balance from our vocabulary. Balance is kind of not the right word because balance means things are actually in balance. Like think of a scale where things are balanced. And that is never the way life works.

Nothing ever is like that. You can have it all just not at the same time. So now pick. Right? There's no point. So what we said is, you know, we're not going to go for balance. We're going to go for harmony. And harmony is such a useful, wonderful word.

I mean, it sounds beautiful as a word, too. But, you know, listen to improv jazz just randomly sometime. Listen to a live recording on Spotify of something. And just let it play in the background. And what you'll notice is you'll sort of lose, you know, it'll fade into the background when it's in harmony. And then when it gets out of harmony, all of a sudden, it'll move to the foreground to be like, whoa, that's not quite,

someone, the drummer's off, you know, or the guy playing the sax, like, what's going on with that? And then it'll kind of get back into harmony and then it drifts back into the background. And so for us and for me, I'm, I'm interested in harmony. I don't need balance in my day. I don't need balance in my week, my month, my life, anything. I just want most of the time it to be harmonious. And when it's not harmonious, it's a signal to me to sort of step back and pay attention.

I wish my 25-year-old self understood that. It would have saved that 25-year-old self 25 years of a lot of stress and tension and frustration and wrestling with, like, what to do. So lucky that I ended up with Amy, who was relentless in her own way of not putting up with things that were not okay in the context of harmony. for us in the relationship, the disharmonious part, getting back to my 25-year-old self, was simply when my words and my actions didn't match up. In an example I'd give of that, as I would say to Amy regularly, deeply in love, you're the most important person to me, you're the priority in my life, whatever. And then in the middle of the dinner, the phone would ring.

And I, in the middle of a conversation, he'll pick up the phone. Or I'd be 30 minutes late to dinner on a night we're going out together, just one more email, you know, which is an endless joke. Like we look at each other. Just one more email, right? Like it can be a joke now lighthearted, but it was like, no, actually, if your partner is the most important person or if your kids are the most important, they're the most important.

And yes, of course there's moments where you have to prioritize something else. But you can say, I got to prioritize this other thing right now. And oh, by the way, if for five years you say, I have to prioritize this other thing every time Like I didn't understand that until I was in my 50-something. So that would be a note. That would be what I reflect back. Search for harmony, not for balance. Listen to things when they're not in harmony.

Really listen and understand what's not in harmony. I love this because I think a lot of it is just about being okay, being its piece with what's yes and what's no. Like I think that's the harmony piece is like saying okay. Like, this is, I'm going to be present now. So, Brad, this was so powerful. Thank you for showing up for the time. We're going to have all your links down in the thing. But how do you want them to reach you or to reach and to obviously buy the book and what else?

Reach me is easy. It's bradetfeld.com. Just give me context. I mentioned at the beginning before we started, I have another friend named Alana. So people can say, the other Alana. You're on Alana's podcast, just sort of context, but just I'm happy to get notes. And then if this is inspiring or interesting books available, you know, Amazon, any other online bookseller.

And, you know, very serious statement. If you like the book, tell your friends. Leave a review on Goodreads or Amazon or something like that. Do that. And if you don't like the book, just throw it away. I love it. So reach out. We want to hear from you.

And I hope you enjoyed it and let us know. And thank you, Brad. This was incredible. This was a delight. I hope you enjoyed this as much as I did. If you did, please share it with friends. Now also, if you're feeling stuck or simply want more from your own career, watch this 30-minute free training at leapacademy.com slash training. That's leapacademy.com. slash training. See you in the next episode of the Leap Academy with the Ilan and Golan Show.