The Tim Ferriss Show Transcripts: Brad Feld — The Art of Unplugging, Carving Your Own Path, and Riding the Entrepreneurial Rollercoaster (#448)

Please enjoy this transcript of my interview with Brad Feld (@bfeld), an early-stage investor and entrepreneur since 1987 and the author of two new books: The Startup Community Way and the second edition of Startup Communities. Prior to co-founding Foundry Group, he co-founded Mobius Venture Capital and, prior to that, founded Intensity Ventures. Brad is also a co-founder of Techstars. Brad is a writer and speaker on the topics of venture capital investing and entrepreneurship. He’s written a number of books as part of the Startup Revolution series and writes the blogs Feld Thoughts and Venture Deals. Brad holds bachelor of science and master of science degrees in management science from the Massachusetts Institute of Technology.

Transcripts may contain a few typos. With some episodes lasting 2+ hours, it can be difficult to catch minor errors.

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform.

#448: Brad Feld — The Art of Unplugging, Carving Your Own Path, and Riding the Entrepreneurial Rollercoaster
Download

DUE TO SOME HEADACHES IN THE PAST, PLEASE NOTE LEGAL CONDITIONS:

Tim Ferriss owns the copyright in and to all content in and transcripts of The Tim Ferriss Show podcast, with all rights reserved, as well as his right of publicity.

WHAT YOU’RE WELCOME TO DO: You are welcome to share the below transcript (up to 500 words but not more) in media articles (e.g., The New York Times, LA Times, The Guardian), on your personal website, in a non-commercial article or blog post (e.g., Medium), and/or on a personal social media account for non-commercial purposes, provided that you include attribution to “The Tim Ferriss Show” and link back to the tim.blog/podcast URL. For the sake of clarity, media outlets with advertising models are permitted to use excerpts from the transcript per the above.

WHAT IS NOT ALLOWED: No one is authorized to copy any portion of the podcast content or use Tim Ferriss’ name, image or likeness for any commercial purpose or use, including without limitation inclusion in any books, e-books, book summaries or synopses, or on a commercial website or social media site (e.g., Facebook, Twitter, Instagram, etc.) that offers or promotes your or another’s products or services. For the sake of clarity, media outlets are permitted to use photos of Tim Ferriss from the media room on tim.blog or (obviously) license photos of Tim Ferriss from Getty Images, etc.

Tim Ferriss: Hello, boys and girls, ladies and germs, this is Tim Ferriss. Welcome to another episode of The Tim Ferriss Show. And I am thrilled to have a friend as a guest today, Brad Feld, on Twitter @BFeld. Brad is the author of two new books, The Startup Community Way, and the second edition of Startup Communities. He has been an early-stage investor and entrepreneur since 1987. I’ve been reading his writing forever it seems. Prior to co-founding Foundry Group, he co-founded Mobius Venture Capital. And prior to that, founded Intensity Ventures. Brad is also a co-founder of Techstars. Brad is a writer and speaker on the topics of venture capital investing and entrepreneurship. I’m going to extend that sentence in our podcast because you are able to speak and write on many more things.

He’s written a number of books as part of these startup revolution series and writes the blogs, Feld Thoughts and Venture Deals, two of my favorite blogs out there, which really are, I think, timeless in a lot of the lessons that are taught. Brad holds bachelor of science and master of science degrees in management science from the Massachusetts Institute of Technology, AKA, MIT. Brad is also an art collector and long-distance runner. He has completed 25 marathons as part of his mission to finish a marathon in each of the 50 States.

Brad, welcome to the show. It’s nice to have you.

Brad Feld: Tim, thanks for having me. It’s awesome to be here.

Tim Ferriss: I can’t wait to dig in. You and I have had a number of conversations and I’ve never failed to take notes and learn, and this is no exception. This is just a selfish indulgence on my part yet again on this podcast. I thought we’d begin with your first off-grid vacation and the genesis of how that came to be. If you wouldn’t mind rewinding the clock and coloring that in for us.

Brad Feld: Yeah. Let’s start with something really calm and relaxed and easy. So I’m married to a woman named Amy Batchelor and we’ve been together now for almost 30 years. The first off-grid vacation I took was a result of a moment in time where Amy said to me, “I’m done.” And I thought she meant that she was done with the week because it had been a really shitty week for me. But she was actually saying very quietly, “I’ve had enough of living this way with you.” This is mid-2000. So we’re in the middle of the deflation of the Internet bubble. It has not crashed yet. It crashed in 2001. But it’s definitely deflating fast. And in the arc for me as an investor, from about 1996 to 2000, was unbelievably intense on the rise up. Like if you sneezed, you made money. The stupidest ideas were successful.

And then that all continued until one day that was no longer true. And so middle of 2000, I’m traveling all over the country because I invest all over the country. I’m doing my best to sort of keep everything together. I’m trying to save what is a portfolio that I have that’s falling apart very, very quickly. Several companies that I co-founded along with a lot of companies that I was on the board of or an investor in. And Amy and I were literally just seeing ourselves on the weekends. So my week would start on Monday morning, I’d get up early at usually four o’clock Colorado time, I’d go to DIA, I’d take a 6:00 a.m. United flight to the Bay Area. I’d spend Monday, all day, in a partner meeting at the firm I was at then, which was during that period of time called SoftBank Venture Capital or SoftBank Technology Ventures. Ultimately became called Mobius Venture Capital.

And I’d stay the night. Tuesday, I’d spend all day in the Bay Area. And then I was a co-chairman of a public company on the East Coast, in New York — in Purchase. So I’d take a red-eye, usually on Tuesday night or Wednesday night, spend a couple of days in New York. Maybe on Friday, go somewhere else and eventually come back home. Crash for the weekend, just out of exhaustion, catch up on whatever I could catch up on. And then sort of Amy would patch me up and send me back out Monday morning and I’d do it again, week after week, for a lot of weeks. This particular Friday that this started, she and I had planned a vacation to our friends’ house, a longtime friend of mine, a guy named Warren Katz and his wife Ilana Katz, who had been my seventh employee in my first company.

And Warren and I had been entrepreneurial friends forever from when I lived in Boston and just good personal friends. And they had a house in Newport in addition to Boston. And so I met Amy in Boston. A black car must’ve picked her up at the airport, came and picked me up at whatever company I had been spending the morning at. We took the car out to Newport and I was on the phone the entire time. And I’m on the phone having these conversations that with the benefit of hindsight were ultimately futile. Every conversation that I had during that period of time, none of them had any positive impact in a meaningful way on the outcomes of these companies. And I probably in between calls, I looked over at her and said, “Hey, sweetie, nice to see you. Looking forward to the weekend.”

We get to our friends’ house, probably around three. Her friends are ready for a beautiful summer evening in Newport and I’m still working, right? I’m on telephone calls, I’m dealing with my email, I’m doing whatever. And eventually it’s six o’clock and we go to dinner. And we go to dinner at some restaurant and by this point, I’m sort of trying to be in the moment a little bit, without really realizing what’s going on. And about, we order, 10, 15 minutes into dinner just as salads are being served, I get another phone call and I just pick up the phone and I walk out. I’m smart enough to get out of the table and go outside. And I talk on the phone for a while and I come back and they’re having dessert. And you kind of know when you’re in a relationship and you’re fucking up. Right?

The signals are not that hard to read. But we went back to our friends’ house and by then we sort of had another whatever, a little more time together and then eventually go to bed. And we’re crawling into bed and Amy says very quietly to me, she says, “I’m done.” And I responded, “Yeah, this was a brutal week. I’m tired. God, everything’s so hard right now. These companies, blah, blah, blah, whatever. I’m so glad this week is over. I’m looking forward to having a weekend with you.” She says, “No, that’s not what I meant.” She says, “You’re not even a good roommate anymore.” She says, “I love you. I think you’re awesome, but I don’t want to live this way and I don’t want to watch you do this to yourself.” And I had enough wisdom. This is in my about 35, have enough wisdom to know not to go to bed or not to roll over when your wife says that to you.

So, we talked for about an hour and I’d like to say, I talked her off the ledge of being done. I said to her, “You know what? This weekend, no phone, no computer, I’m done.” I gave her my phone. I gave her my computer. I said, “Put them in your bag. Between now and when we leave here Monday morning, I’m not going to do any work. I’m not going to think about work and I just want to spend time talking about what we need to do differently, what I need to do differently.” And after about an hour, all right, things are calmed down and we’re kind of starting to doze a little and I knew better than to nudge her and say, “So any action happening tonight?” Because all that was going to generate was more laughter.

So we go to bed, we wake up the next morning and we go for a walk. And I said, “Look, I know that you’re not happy with the dynamics here, but I don’t want to split up. I love you. You’re the person I was put on this planet for. I think I was the person you were put on this planet for. I’ve got an engineer’s brain, just give me some rules.” And she looks at me and her first response is, “I don’t want to give you rules. That puts it on me and that’s not romantic.” And then she sort of snaps into focus and she says, “You mean, I get to control you?” And I said, “Yeah. Yeah, just give me some rules.” And we walk a little bit more and she says, “All right. The first thing I want you to do is I want you to keep track, each day, of how many hours you work and I want you to report them to me.”

Now she knew that this was pressing a gigantic red button in the middle of my forehead. And it’s what our significant others do, right? And what we do to them. You know the biggest point of pain or the biggest trigger of your significant other, if you have one, and they know of yours. And she was doing it on purpose. My first company, we kept track of time in five-minute increments as a software consulting business. And this was the 1980s. So we kept track on a piece of paper. So for seven years, I ran this company, for seven years. Every day, including weekends, I had a paper grid that I filled out 9:10 to 9:25, and then a code for which client I worked on.

And then a one-sentence description of what I did, just like lawyers do. But we did day in and day out. And when we sold that company, I said, “I am never fucking doing that again. I’m never doing something where I have to keep track of my time again.” And so my first reaction was, “No, I’m not going to do that.” And she looked at me and she says, “You said I could make the rules.” So we ended up having an amazing set of conversations that week. It didn’t solve anything, but there were two things that came out of it. One was a bunch of tactics and I’ll talk about one in particular in a sec, but the other was real clarity for what was wrong. And it wasn’t hard for her to say it and articulate it. And it wasn’t hard for me to hear it, but it had to be said, and it had to be articulated.

And the specific thing that was wrong was my words didn’t match my actions. And that has become a foundational part of my relationship with Amy and a key part of how I try to live. Although we’re human, I make mistakes, I screw up plenty. But I try to have my words match my actions. And in the context of the relationship, I’ll use the phone call as an example. This is before we had iPhones, before there was even on your cell phone, caller ID, you just saw a phone number. And you actually, I think, had to have a caller ID special thing on your home phone. And so somebody would call me on my cell phone and I’d be in the middle of a conversation with her. We’d be at the middle of dinner, we’d be in the middle of a movie, or we’d be in the middle of name your other thing that two adults do.

And my phone would ring and I’d answer it. No matter what was going on between us, no matter what sort of interaction it was, because I prioritized the random person who was calling me over Amy. Yet my words were, “Amy, you’re the most important person in my life. Being with you is the most treasured thing I have. I like to be with you more than anything else. Sorry, I’ve got to answer this phone call.” And you could do it with phone calls, you could do it with emails, you could do it with work. I was late to every single thing we ever did because I just had one more thing to do before I went to the dinner that we had scheduled for the fancy night out or whatever. So when she said to me “Your words don’t match your actions,” and then gave me an example, that really snapped into place. And that’s been foundational.

The other part of it was, and this is a thing I’ve learned about Amy, I don’t have much of a temper. I suppress my anger and frustration. I’m like Marge Simpson and I just push it down to my toes. And I have lots of other ways to process it. Some that are not particularly healthy, which I expect you’ll probe me on at some point. But I don’t have much of a temper. It takes a lot to get me to react with anger, external anger. Amy has a temper and I learned early on in our relationship that there was no value in trying to win when her temper started to escalate. It was mutually assured destruction. She’d just keep escalating, I’d escalate, she’d escalate, I’d escalate, she’d escalate. I eventually like, lay on the ground, like your dog that says, “Just pat me on the stomach, I give up, I yield.”

And in this particular moment, she said, “The reason I’m so angry right now is I’m scared. I’m scared for you. I think you’re killing yourself. I don’t think you’re having fun. I don’t think you’re enjoying what you’re doing. I don’t think you’re creating enough space for you.” She didn’t say I’m enabling that, but that would be the language we’d use today. And so from that came this idea of basically a quarterly vacation off the grid. So each quarter, since 2000, we take a week, Saturday to Saturday, and we just go off the grid. And I’m fortunate that I can take four weeks of vacation like that a year. And we screw up some. Sometimes we don’t end up doing it, or I end up sort of being on or off. It took probably a dozen times before it wasn’t a terrifying experience.

The process, literally, of turning off my phone and leaving my computer at home when we got on a plane and went somewhere for a week of vacation was so incredibly anxiety-producing. The challenge that I had for the first couple of days of disconnecting from the momentum of my work life and shifting into this open space and time in front of me, with the person I love the most, was so hard to do. But it was so worth it. Three or four years later, the muscle that was built was four times a year. I kind of just say to the rest of the world, “Fuck it,” and disappear for a week. 

And as far as I can tell, all of those fears that I have — oh by the way, there’s a lot of anxieties that one has when they go away, right? If I’m not here for this meeting, this bad thing will happen, or this will happen or I won’t sell this stock, or I won’t close this investment or I’ll miss this new opportunity or whatever, right? Pick your business anxiety. Well, yeah, all those things happened, but none of them were significant. They weren’t meaningful relative to the meaning and the value of being able to spend this time with Amy and with me, the two of us together doing what we wanted to do rather than doing what the rest of the world wanted to do.

Tim Ferriss: I’d love to ask a few followups about the quarterly off-the-grid vacation. Was the, let’s just call it one-year withdrawal process, and I use that term deliberately, was it just a psychological, heroin-like withdrawal process after which you were more relaxed? Or were there changes that you made to the format or the timing or what you did that helped to reduce the anxiety of taking the week off the grid? And for people who are wondering what that means, just to underscore what you said, that’s no work, no email, no calls, no Web surfing, no news. It is off-grid.

Brad Feld: Yeah. It took more than a year to detox or to get into a place where it was like flipping a switch. Today, I have a ritual. My ritual is on Friday night, I turn on my email responder. My email responder usually says something like, “I’m taking a week off the grid. I’m not checking email. When I get back, I’m archiving all my emails, so I will not see this email. If you want me to see it, send it to me again after day X,” which is usually Tuesday, not the following Monday. Because I come back to Monday and 75 people send me emails first thing Monday morning. It’s like, okay, now I’m just dealing with last week. And not surprisingly the whatever, pick the number, I don’t know, a thousand new emails a week or whatever, a couple thousand new emails a week that come in, it’s kind of to just start Monday morning with nothing in your inbox.

Tim Ferriss: Yeah.

Brad Feld: It took me a while to figure that out. So for the first couple of years, I would put a vacation reminder up and I come back to this onslaught and I’d live again the previous week. So it wasn’t as though I got to not experience that week in the rest of my world. I had to go live it again on Monday morning. And by the end of the day Monday, all of the things that happened over the week were again in my head versus if I just deleted the week. Yeah. Some of them were important and they’d surface again. But the vast majority of them were not important. Just cognitive dissonance, overhead I didn’t need. Second was cheating. Every hotel has a computer connected to the Internet.

Tim Ferriss: Sneaking into the refrigerator at midnight to have the ice cream.

Brad Feld: Totally. Right?

Tim Ferriss: The best diet ever.

Brad Feld: Cheating in a way that undermines everything you’re trying to do for yourself. Right? So on Wednesday it’s like, I’ll just go check and see and boom, the whole, everything you’ve just done is, in terms of your own mental adjustment and mental health, is gone. Independent of whether or not Amy catches me cheating. In which case, then I’m actually cheating on her, which is kind of like not the contract that we had. Do your words match your actions? No? That’s the foundational thing. So there’s like getting through that. Then there’s the, “I only have this one thing I have to do this week, this one really important thing that just can’t wait the week.” In 20 something years of doing this, I don’t think there’s actually ever been one of those.

I mean, I’ve made them up. Right? And I’ve had plenty of them that have distracted me, but I don’t actually think there has ever been really one of those. If there really was one, you’d move your vacation. Right? You’d move the week to another week and say, “Look, I really, we’re on the roadshow for taking this company public this week and I have to be involved and I can’t be off the grid. Okay. Well, let’s move the week.” So, there were a lot of things like that that took making mistakes. Like it wasn’t like, oh, okay, good, cool, let’s just go do this thing. It’s a commitment I made to Amy and a commitment she made to me to build this into our life in a way that would be successful and healthy for both of us.

Tim Ferriss: Do you have any particular pattern to your scheduling? Do you try to do it the first week of the quarter or the last week of the quarter? Is there any pattern to that at all when we think about scheduling?

Brad Feld: There isn’t. Some years we sit down, my birthday is December 1st and I have been for a number of years. I used to do it privately, now I do it publicly. I write a post that’s a version, it’s called v, whatever my age is. So I turned 54 last December. So I wrote BFeld v54. And the year before I wrote BFeld v53. And oftentimes around that, we’ll sit down and we’ll look at the next year and we’ll try to get ahead of the calendar nonsense and just block out some weeks. But they’re not four weeks that are necessarily just convenient for me because Amy has a professional life. She’s on the Board of The Nature Conservancy. She’s on the board of Wellesley College where she went to school. She’s got some other responsibilities that are part of the schedule.

So some of it is just navigating our collective schedule. Some of it is also when we need it. So there are moments where we’ll have it, and it’s a month from now, and we’ll look at each other and say, “We’re fried. We need a break.” And I would say even in this moment of the COVID crisis and the dynamics of work, our entire schedule from March to December, we just deleted. We said, “We’re not going anywhere in 2020. Other people can, but we’re not. We’re just going to stay home.” And I don’t know when I’m going to leave my house again, but it’s certainly not going to be in 2020.

And therefore, all of this stuff, that’s a trip here, a trip there, a thing there, a thing there, none of that matters. So let’s look and think what tempo we really need so that we can maintain the intensity of our normal life pace. We have learned, by the way, that Saturday to Saturday is the trick. We used to come back on Sundays. It didn’t give us enough gear downtime. And we used to leave on Sundays and leaving on Sundays just meant that the weekend, you lost that front end weekend. If you left first thing on Saturday was when it starts. Even if we don’t go anywhere, a lot of times we’d just stay home. Yeah, it’s just enough space.

Tim Ferriss: It just gives you a more gradual off-ramp, on-ramp and on-ramp, or on-ramp and off-ramp, excuse me. The next question I have for you may be related, may not be related, but there’s a line here that I have in my notes, “They can’t kill you and they can’t eat you.” Can you provide some context for this, please?

Brad Feld: Sure. It’s one of my favorite professional moments ever, maybe one of the most important ones ever. That line was said by Len Fassler, who is one of the two guys that bought my first company. Two guys who are named Len Fassler and Jerry Poch were partners in a company that was called AmeriData, which ultimately got acquired. It was a public company that got bought by GE Capital. Len is my closest mentor. He’s the person I’ve learned the most about business from over my career. He’s in his late 80s. He’s just a spectacular human on many, many, many dimensions. We had co-founded a company in 1996. So Len and Jerry bought my company in 1993, GE bought their AmeriData in 1995, and Len and I started with two other people, Raj Bhargava, an entrepreneur I’ve worked with a number of times, and Steve Max, who also had had a company bought by Len in 1996.

And that company was a company that bought Web hosting companies. And we did a consolidation of Web hosting companies. That really was one of three companies that created a category called application service provider. And ASP was a precursor to software as a service, or SaaS. And there was like a rise up at the end of the ’90s and then a complete collapse in 2001, 2002. And of course, 20 years later, software is delivered on the Web online. That was essentially the business that we had created. In the end, we didn’t execute it correctly.

We bought a bunch of companies, I think about 25. We went public in 1999. We had a peak market cap of right at $3 billion back when a market cap of $3 billion was a big market cap for a tech company. Our company was called Interliant. And when the Internet bubble burst, we had mastered, we built about a $200 million a year business. So a pretty sizable company, 1500 employees, and Len and I were co-chairmen. So we didn’t run it. We had a CEO who ran it, but he was full-time. I was part-time because I was also a partner at the time, at Mobius. We mastered the art of losing $5 million a month. So we had built this company and basically we’d grown incredibly fast, most through acquisition, some organic growth, but we didn’t have a cost structure that worked.

And so as a business, we had lots of real estate leases for data centers. We had lots of equipment leases, we had lots of OPEX and basically $5 million went out the door every day. And for a while, that was fine because capital was freely available and the only thing that the market cared about was growth. And so we were handsomely rewarded for growing incredibly fast, independent of the fact that we have mastered the art of losing this money. Now there’s another company about the same time as us, another company people may have heard of called Rackspace. And Graham Weston, who is the CEO of that company, we knew of each other, but we didn’t have a relationship. And Graham ended up, we became friends years later and he said our problem was that we’d mastered $5 million of loss a month. He’d only mastered a million. So when everything reversed, he was able to get to cash flow break-even; we weren’t.

So we’re now on the downside of the utter collapse of this business, that at a moment in time had been the most successful thing I’d ever been involved in. And I was a co-founder. So I had a huge amount of personal value tied up in the stock that then was every day vanishing. We were doing layoffs. We were selling pieces of the business. We were just trying to survive this complete collapse. And I was trying to survive it in the midst of flying across the country every week, having 20 other companies that I was involved in that were all falling apart at the same time, this is the same timeframe. And when I would go to New York, I would stay at Len’s house. I had an apartment in the city, but a lot of the office was in Purchase, so a lot of times I would just stay in purchase because it was just easier.

And I have such a vivid memory of waking up for breakfast at his house, because he didn’t really have breakfast. So I’d wake up and I take a bagel and I cut it in half and I put it in a toaster and I put cream cheese on it, I made a cup of coffee, and then eventually he’d sort of wander in and we’d go to the office. And this particular morning, I was so fried and just so despondent. And I just knew it was going to be another utterly shitty day. I don’t remember exactly what was in front of me that day, but whatever it was, it was going to suck. And I’m sitting at his little kitchen table. He’s got this beautiful house in Harrison, his little tiny kitchen table in the corner.

And I’m chewing on a bagel. I didn’t even bother toasting it or putting cream cheese on it this morning. Just gnawing on it like a depraved dog or something. And he comes in and he sneaks up. He just comes in behind me, puts his arms around me, like in that big hug somebody gives you from behind. And Len’s short, he’s like 5’5, he’s like Yoda, like a Jewish Yoda with ear hair and stuff. And he just kind of hugs me from behind with this sort of heavy hug. And he then grabs me on the shoulders from behind. And he says, “Brad, they can’t kill you and they can’t eat you. Suit up.” And he didn’t need to be doing any of this work. Right? He could have said, “Fuck it. I don’t want to do this anymore. Why are we doing this?”

He was in that thing till the end. He felt an obligation to do the work, even as it was all falling apart, even though he didn’t need the money. He was doing it because I’d asked him to do it with me, that sort of thing. But that moment of I’m at the absolute bottom of this, but I’ve still got shit to do and him just sort of saying, “Just suit up, let’s go,” was a powerful moment for me. And I’ve had many, many other up and down experiences since then. But ultimately, they can’t kill you and they can’t eat you. And now some people may argue that depending on where you’re from and where you live and what you’ve had to deal with in your life. But in the context of the US in business, entrepreneurship, trying to create things, those things are true. They’re not allowed to kill you and they’re not allowed to eat you.

Tim Ferriss: Thank you for explaining the backstory. And there are so many other bullets that I’d want to take you through at every turn of the roller coaster.

Brad Feld: Yeah, thanks so far for like the first 30 minutes being Brad Feld’s version of misery.

Tim Ferriss: Yeah. It’s like putting the cat in a pillowcase and whacking it against a tree. That’s usually not what I do on my podcast, but it is leading somewhere. I do promise that. And I’ll just provide maybe a quick montage that we don’t have to go into the details of necessarily to get to a question. Now people might be inclined to think, well, Brad, he has this illustrious bio, he has all these successes. I guess when it’s bad, it’s really bad and when it’s good, it’s really good. But there are also stories about, for instance, some of your best investments, like Fitbit, where even in the midst of this meteoric rise, you have these emergency board calls and potential product recalls and product recalls, all for the right ethical reasons where you’re puking into a garbage bin after phone calls and having these really difficult experiences and visceral reactions.

I’m going to use that as a segue to a blog post. And this is a pretty recent blog post, from 2020. But this is quoting from that blog post, “I’m officially DSM-5 300.3: Obsessive-Compulsive Disorder. If you know me, you know that I’m a counter, arranger, and checker with some washing (mostly hands) tossed in for good measure. My magic number is three.” So there are a few. This is a multi-parter; I apologize. It’s a sloppy way of asking questions. But you have spoken regularly since 2013 about your struggles with anxiety and depression. Two questions. Why is your magic number three? And why did you begin in 2013 to talk about these struggles?

Brad Feld: Well, let me answer the second one first. I discovered depression in my mid-20s and I’m sure I had been depressed before, but I didn’t have language for it. And I was always anxious. That anxiousness translated itself often in a very positive way. It created focus. It created intensity. It was linked to need for achievement. But there was always anxiety. The anxiety manifests itself in lots of different ways.

In my 20s, I had three things happen simultaneously. I’m one of those kids. Growing up, my dad was a doctor, my mom was an artist. We grew up in Dallas, Texas. We had plenty of resources. It was an interesting place to be in the ’70s and ’80s. I think there were 2,000 kids in my high school, I don’t know, 1,500 kids in my high school, some big number. Four of them were Jewish. So I had funny holidays, and I had some moments that were not great moments as a Jewish teenager surrounded by people who weren’t. But generally I had very easy teenage years. My parents were very supportive, loving, challenging in different ways in different times, but very much there for my brother and I.

I went to college. MIT is a place that is a daily assault on your self-esteem. You show up. You’re at the top of your class in high school, and you’ve done well in everything, and you think you’re really good at stuff. I remember a month in — Everybody has to take physics as a freshman. I get a test a month in. I knew I didn’t do well on the test. I got my grade. I got a 20. This kid never made — 

Tim Ferriss: That’s out of 100?

Brad Feld: Out of 100, yeah. I got 20. I never got — maybe I got a B in some English thing somewhere. I thought I was really good at physics. I got a 20. What you do when you’re 17 years old, at college, away from home, and you got a 20 on your first physics test? I went in my room, and I cried for an hour. I closed the door and I cried. I didn’t know what to do. How do you even process it?

Turns out class ave on that test was 32, so I actually got a B-, C. Who the fuck gives the first test so that the class ave is a 32? MIT. That’s what they do. They make you very aware that you are — there’s 10 percent of the people that are off the charts, but they make the other 90 percent very aware, “Yeah, you’re smart kids, but you’re going to have to work hard.”

College, I was successful. I started a company. It was successful. I married my high school sweetheart, not Amy. I was in a PhD program at MIT at a very young age, while running my company. Externally, everything looked awesome.

Then three things happened in fairly short order. Remember, I’m anxious all the time, so I have an incredible amount of anxiety that I’m carrying around with a bunch of things. The three things that happened in order were, one, my marriage blew up, so public failure. Two, I got kicked out of the PhD program because I was a lousy PhD student. I was running my company, and I wasn’t taking it seriously. Three is I was incredibly bored of my business. My business, while it was succeeding, was not stimulating me in any way, shape, or form. These three things tipped me into a very deep depression.

When that happened, I had incredible shame, shame at all levels, shame that I was depressed. Fortunately, my PhD advisor, who to this day is still a wonderful substitute paternalistic figure for me, a guy named Eric von Hippel, connected me with his therapist who was a classical Boston psychiatrist.

Turned out that OCD at this time was not well understood. It was just starting to be better understood. Fortunately, I got diagnosed with that. The treatment that I had, which was both CBT and medication, was highly effective.

Tim Ferriss: What’s CBT?

Brad Feld: Cognitive behavioral therapy, a certain type of therapy where it’s — you think about therapy with laying on a couch with your back to the therapist is one type of therapy. This was a sort of conversational therapy, but it was actionable around certain things.

But I really understood that I was having a major depressive episode, and the thing that had triggered it was my inability to manage my OCD. But on top of all of this is this incredible shame, shame of all those dimensions. I couldn’t tell anybody I was taking medication. Oh, my God. If anybody knew I was taking medication, how awful would that be? So I go through that phase.

In my 30s, 9/11 triggered another really intense depression that lasted about three months. I was in New York. I had taken a red-eye to New York the night before the towers fell. I woke up as the towers were falling, literally. I was in Midtown, so I was never really in harm’s way, but I was terrified.

That depression was kind of in plain sight. That was at the tail end of the collapse of the Internet bubble, so everybody in my business world was completely a mess. And now all of the United States is a mess for a couple of months, because we’re all struggling with “We’ve been attacked. We’ve had friends die. What does this mean?”

No. These were not my only depressive episodes, but these were the ones that were extended, profound, lasted more than a couple of weeks that I really was in the midst of.

In 2013, I had another one. This time it was a result of a bunch of things that happened in 2012. They started with me running a 50-mile race in April of 2012. I overtrained. I trained a lot. I was working a lot. My business world was going very well between Foundry Group and Techstars. Had a very healthy relationship with Amy. I had lots of things, but I was working really hard. I did this 50-mile race. I trained a ton. I did the race, and I didn’t take any time in recovery. I just kept going.

A bunch of things happened, including a near-fatal bike accident at the end of the summer. One of our dogs died. Sounds like a country music song sometimes. I ended up with a kidney stone that I had been ignoring and just avoiding. “Never mind that blood comes out when I pee, no big deal. I’m sure that’ll go. I just ate something wrong.” And on and on and on.

In the end of this, at the end of 2012, I was physiologically exhausted, just completely kaput. I had this kidney stone surgery, which had a very big kidney stone, they had to actually do surgery to get it out. I took most of December off to recover. I thought I was fine. I’m like, “Okay, let’s get back to it.” I went to CES in Las Vegas, Computer Electronic Show, which is the second week of January. Literally within two weeks of getting to Vegas, getting to my hotel room, I’m in bed with a pillow over my head, and I know I’m totally screwed. I’m in a depressive episode.

In 2012 and then also in 2013, several entrepreneurs committed suicide. There was a little bit of conversation around that, but not a lot. Aaron Swartz was probably the first of the stream. There was a pop of, “Oh, my gosh. This person — how could this have happened?” Then it would drift away.

In this moment, I wasn’t ashamed anymore. I had been open about my struggles with depression to my friends. I was blogging all the time about my life, for various motivations, a lot of it to be that I think by writing versus thinking some other way.

Tim Ferriss: Brad, can I pause you for one second?

Brad Feld: Sure.

Tim Ferriss: I just want to — please don’t lose your train of thought, but when you say, “I wasn’t ashamed anymore,” was that because you had been discussing it with friends, was it because of the half-life of shame just decayed over time? Because that’s a really — 

Brad Feld: Yeah.

Tim Ferriss: That is not an incremental change.

Brad Feld: No. It’s a good thing to interrupt with.

In my 30s, I was still pretty ashamed of being depressed, but I realized I was depressed out in the open. By the time I got into my 40s, and when we started Foundry Group, we made a commitment to each other at the beginning that we would be emotionally available to each other as partners. Our effectiveness of that, how well we’ve done it, that has ebbed and flowed over time. I wouldn’t say that we are perfect at that, and that’s been awesome, and it’s never had trouble, but that was a thing that was an important part of my own value system from the beginning is I had been in this partnership at Mobius, where some of the partners were emotionally accessible to each other, but many of them were not. There was a lot of bullshit, and there was a lot of stuff that was not great through that. So we started in 2007 with that framing.

During that period of time, all four of the original partners had plenty of ups and downs. We had lots of conversations about it. So I gradually became less uncomfortable talking to people in a professional context about it.

My closest friends that were outside of a work context, people like Warren, other friends like my first business partner, a guy named Dave Joke, many people like that who supported me through some of these depressive episodes, even if they weren’t totally tuned into what was going on with me, as we got older, we had longer conversations around them.

Then one person in particular really changed how I approached it, which was Jerry Colonna. I know you know Jerry. He did a great podcast with you not too long ago.

Tim Ferriss: The coach with the spider tattoo.

Brad Feld: Indeed. Jerry is one of my closest friends. I regularly refer to him as my soulmate. He and I have known each other going back to the mid-’90s. I knew Jerry when Jerry first started working with Fred Wilson, when they started their firm Flatiron Partners.

I knew Jerry much better than I knew Fred. Fred and I got along and hung out, but I was really close to Jerry, and we did some deals together. It wasn’t really until the late ’90s, almost early 2000, when Jerry was kind of departing, that Fred and I started to really engage with each other at a deeper personal level. There was some point along the way where, all three of us are very close, and Fred said something to me like, “When I was partners with Jerry, I couldn’t handle both of you. When Jerry finally disappeared for a while, I could handle you.” He said it in jest, but there’s some element of it in terms of the emotional engagement.

So I’m sitting with Jerry. This is before I’m depressed, but as we’re going through things, maybe 2010, 2011, and we’re having these conversations about how full of shit most of us are all the time. He’s coaching now. He’s really pulling out of people, without having to do a lot of magic, because his magic is right up front, not the bad, the real.

In this conversation that we’re having, we talked very quickly about depression. He’s been depressed. I’ve been fortunate that I haven’t had the suicidal attempt and really the suicidal ideation activity that he’s had, but the depth of the depression is something that we talk about pretty openly.

I don’t remember exactly what the words were in that moment, again, this is 2010, 2011, but he said something to me that caused me to change my mode with the founders that I was working with and the leaders that I was working with, where I was already, I think, pretty emotionally accessible to them, but I still think many of those relationships are power relationships. I’m the investor, they’re the CEO, so therefore, the level of comfort that they’re going to have, being open about how they’re actually doing at any moment of time, varies a lot.

Jerry’s point to me was “You, Brad, can be a better leader by just being you, and letting go of your constraints around how you present. You already don’t have many constraints around how you present yourself.” I always think I’ve been a pretty — I am what I am, and I try to talk about it very openly. But he says, “You’re holding back on this dimension. The fact that you don’t ever say you take medication, you’re holding back. The fact that you don’t talk about therapy, you’re holding back.” I carry that with me.

When I had this depression in 2013, I hadn’t been in therapy since I was in my 20s, I immediately went back into therapy. I remember the day that I had that therapy session, which was — the first therapy session with a new therapist is worse than the first day of school at a new school, just kind of sucks. But I wrote a blog the next day. I’m like, “You know what? I’m just going to write about how I’m feeling. I don’t want this extra layer of pressure on myself.”

Interestingly, there was a very strong, mostly positive feedback loop that came out of that. Some negative, definitely people like, “Why are you saying this? The bad guys are going to get you.” People didn’t understand why I’d say something like this. “Why would you expose your weakness?” Plenty of — I remember when Fred and I started blogging in 2004 timeframe, lots of people said, lots of VCs, lots of our peers, said, “Oh, they must have way too much time on their hands to write blogs. Everybody writes blogs.”

But it’s kind of the same thing. It’s like, I don’t really care what anybody else says about it. This is going to make me feel better, to let myself let go of this shame. I’m going to let go of this shame in an active way. If that’s helpful to the people I work with and the people that I support, that’s a good thing.

The other side of it, the positive feedback loop is, during this period, three, four months, I don’t know the number, 50, 100 people whose names listeners would recognize, well-known entrepreneurs, well-known investors, a few well-known public figures that I didn’t know, reached out to me for one reason or another. I did a few interviews, because then all of a sudden Inc. magazine wants to write an article about entrepreneurs and depression. Okay, fine, Jerry and I are in that article together. There’s a little of that going on.

But I had a bunch of emotionally intimate conversations with very successful people, many of whom said I was the first person they were having a real conversation with their own struggles with depression with. That didn’t make me feel necessarily better, but it made me feel that what I was doing had value. That created a positive feedback loop which over time essentially obliterated the shame. Didn’t just make it go away. It obliterated it. It’s like, “No. We’re human. This is part of the human condition. We can either deal with it or not deal with it. I’m fine dealing with it.”

Then of course if you look at the evolution of Jerry, and if you read his book Reboot, just understanding that if one wants to have, put your adjective in — it doesn’t have to be better, more satisfying, more successful. I don’t care what you fill in the blank with, but make it a positive word, knowing yourself and continuing to scrape away all the kruft, and continue to recognize that we’re all flawed, and being willing to keep going deep on ourselves, and to the extent that we can do that without fear, without shame, that is even more satisfying.

I think that was it all clicking into place for me, which is, “All right. I’m going to die some day. I hope that I have more good experiences than bad experiences between now and then.” I probably will, because, in the Warren Buffett words, I won the genetic lottery. I’m a white male in America. I happen to be in my mid-50s. I’ve got plenty of resources. Probably lots better than worse for me, and so I should be aware of that, and try to use that as a force for good in the world on whatever dimension I can.

Tim Ferriss: You mentioned that Jerry’s magic is upfront. By that, do you mean the questions that he asks? Or does that have a different meaning?

Brad Feld: A little of that. Some of it’s the questions. Jerry has a well-known superpower, which is that people start crying in front of him in a group right away. People that would never imagine that they’d start crying and let their emotion out, let their emotion out.

One of the things that is so fascinating is he’s not really trying to do that. What he’s doing is he’s locking in on the person in the moment, and being fully present for the person he’s talking to. He’s then instinctively locking in, I’m using that word on purpose, on what is going on with them, and not so much what the surface level stuff is, but two or three layers down, what’s really at their core, what they’re really afraid of, what they’re not saying, what they’re not acknowledging to anyone, but especially to themselves.

He opens that door quickly. It doesn’t take four years of therapy to open that door. He opens that door in the first 15 minutes. All of a sudden, the door’s open. You don’t have to dance around it for four more years. When the door opens, some people run away. It’s terrifying. But for most people, they’ve already committed that they’re going to do the work. They’ve already said, “I want to be here.” So when that door opens, all the barriers just crumble all at once.

He is so good at that, one-on-one, but especially in a group setting, but doing it in a way where everyone feels like they’re part of the experience, rather than he’s singling you out. It’s not like you’re in Harvard Law School waiting for the professor to point at you next to talk about the case and explain what happened, or Harvard Business School, or wherever they do shit like that. I didn’t go to Harvard, so I got to make stuff up about Harvard.

But it’s everybody in the room is all of a sudden teleported to this place where they’re both empathetic to the person who is engaging intensely with Jerry, but it’s reflecting on them. It’s allowing them to let their door crack open a little.

Then he stays with it. He stays with it not in a hostile way, not in an aggressive way, not in an attacking way, just in this Jerry way, I don’t have a label for it, that at least for my experiences with him, take people to a place where they realize, “Wow. Okay, what is important to me?” very, very quickly.

Tim Ferriss: Yeah. He’s very good at honing in. He skips a lot of the foreplay, which I find refreshing. Some of the questions he’s posed to me, or had me pose to myself, have really stuck with me. One being: “How are you complicit in creating the conditions you say you don’t want?” Then you were talking about things being said: “What is not being said?” or “What is being said that you are not hearing, or that is not being heard?” These types of questions I found really, really fruitful.

Brad Feld: The one about how are you complicit in the conditions that you’ve created is so powerful to reflect on. It’s a conversation that Amy and I have been having for 30 years. I work too much. I work a lot. I create time and space for myself. I used to travel all the time. I could complain about it, but how am I complicit in creating those conditions?

I have — you did too, right? You have the freedom to do what you want to do, where freedom is a very American word in some ways, very poignant word in this moment. But as, again, white men with resources, we have a lot of freedom relative to many other people, most other people on Planet Earth. So when I find myself in a modality that I don’t want to be in, working too much, or not having time and space for my relationship, or fearful of something, or whatever, in a relationship with a company, with a founder, with work, with a friend, that’s not healthy for me, what is my responsibility? What is my role in creating those conditions?

A lot of times, when I look at that and carve out the time to look at that — there’s a tactical, “Okay, I’m not going to do this anymore. I don’t want to do that anymore. I’ll stop doing this.” That’s tactical. That’s different than going into it and saying, “All right, I can change that. I can fix my schedule. I can delete some things. Why am I doing this? What is it satisfying in me? Is that thing it’s satisfying a good thing or a bad thing? Is it a wanted thing or an unwanted thing?”

Man, even with things that seem so obvious from the outside to my best friends, I don’t see them. I think that’s true for many people. We’re in complete denial of how we’re creating those conditions that create our unhappiness. Create our happiness, that’s good, but create our unhappiness, create our limitations, create our, put whatever box around and put a negative sign in front of it. Again, he is good at poking through that, not touching it and tapping it, but just barreling into it and saying, “All right. Here we are in this box. Let’s talk about all the mess that’s in this box.”

Tim Ferriss: There’s something also very special about — I haven’t interacted with Jerry in a group environment, but in small group environments, particularly in — this is what often happens when people self-select to interact with someone like Jerry, is someone will break the ice and really express vulnerability, which gives you permission and greases the skids for you to do the same. So in some respects, you might anticipate that being forthcoming and vulnerable in a group environment would be harder. But I think for a lot of people, it’s actually easier. I do think there is something to that.

Brad Feld: It’s a good insight. It’s probably one of the reasons why group therapy is a thing. He and Reboot, his company, Reboot, have done — they started off doing CEO retreats, and then he and I hosted a number of VC retreats. I don’t know how many we’ve done now, five or six. We do them — 

I have a separate building on our, we have 40 acres just on the edge of Boulder, and I have a separate building I call the carriage house. It’s two stories, and the upstairs is perfect retreat space, and the downstairs is a place you could have nonprofit fundraisers or dinners or whatever.

He and the Reboot team would take over the space for four days. My only request of the people that came is that they don’t come to the house. They don’t bother — I have a sort of like, here’s the area around my house, specifically, but you can wander the land. You can wander the property. You can go sit by the swimming pool. You can do whatever. We have a fire pit. They do a fire ceremony at the end of the thing.

I would typically go for a day. The first one I went for the first three days, and it’s a four-day-long thing. My observation, having now been to three or four days of a couple of CEO ones and a couple of the VC ones, and then having gone for between a meal and a day to the rest of the VC ones, everybody shows up with their armor on. Imagine a bunch of VCs showing up to a four-day thing like this. They’ve got their armor on, or CEOs, either one.

The beginning of it is a little group bonding and a little bit like recognizing that you’ve got your armor on, but because it’s so fast, you very quickly realize that your armor is just making you uncomfortable and sweaty, and it’s weighing you down, and it’s hard to sit. So you start taking your armor off. Then somebody just takes their armor off and goes for it. After that first person does it, the next thing that happens is everybody stands up, takes their armor off, throws it out the window, and then you’re off to the races. I’ve seen this happen every single time. It usually happens within the first couple of hours. It’s remarkable.

Tim Ferriss: I think of you as having a very rule-based engineering mind. How do you choose — you can answer either of these. How did you choose your therapist when you got back on the horse and decided to get back in that game? Or what do you say to someone, let’s just assume it’s a technical founder, someone who has an engineering mind, and they ask you for advice as to how they should choose a therapist. Because there is every possible flavor of therapist on the spectrum, every possible style. What are your thoughts for yourself, when you went back to choose a therapist, or for someone asking you how they should choose or find a therapist?

Brad Feld: You reminded me that I never answered why three is my magic number. We’ll come back to that.

I’ve chosen two therapists. I chose a therapist in my 20s, and I chose a therapist in my late 40s. Here’s how I chose a therapist each time. A person who I had immense respect, admiration, love for recommended their therapist, or a therapist they knew well, that they thought would be good for me. They did it with no strings attached.

In the first case, in my 20s, it was Eric von Hippel’s therapist, my PhD advisor’s therapist. I probably didn’t — I was in such a bad spot that I probably couldn’t have done an evaluative process. I just needed some help.

I had had one prior bad therapy experience, which was before my first wife and I split up, we went to — she was going to a therapist, or she had started going to a therapist, and then her therapist or she suggested that I come and we do couples therapy together, which I have subsequently learned is a terrible idea if one of the partners has already been seeing a therapist.

We had one session. I don’t know. The word malpractice is loaded. I felt attacked for the entire 50 minutes by her therapist. That was it. We didn’t go back. Our relationship was probably already done before I went to that therapy session, or certainly was done before I went to the therapy session, just hadn’t got to that point. So I already had a bad experience.

With Eric’s therapist — the other thing was his name was Dr. Mogul. I thought, for an entrepreneur, that was the perfect name for a therapist. But I was in a place where I didn’t have evaluative criteria. I couldn’t have done anything, but he was well suited for me. He was what I needed in the moment. So I got lucky in some ways, but it was because Eric knew me well enough, and I trusted Eric. So that worked.

The second time, my therapist was recommended to me by Jerry. It was a friend of Jerry’s, not a therapist of Jerry’s. I said to Jerry, “I want to do therapy again. I’m not really sure what I want this time around, but I want a longer-term relationship.” The first time I’d done it for four years. I said, “I don’t know whether this is a four-year thing or a 20-year thing, but I want somebody who I could have a 20-year relationship with, because I’m in a place in my life — “

I think I was 40, 47. I know I’m in midlife. I know stuff is shifting. I know my hormones are shifting. I know what matters to me is changing. I know I can’t run a seven-minute mile anymore, even if I’d like to. I want somebody that I can navigate through this next phase with. I said, “I don’t want a psychiatrist. I really want — ” It’s Boulder. “I want somebody who has classical training, but I want them to be Boulder, earthy, crunchy, hippie, Buddha-y,” whatever. I said, “I want that in my life at this stage.”

He said, “I’ve got the perfect person for you.” It was a classically trained psychologist. His name was MacAndrew. His last name is his first name, and his first name, his last name, which got me at hello. There’s a school in Boulder called Naropa that was one of the very first alternative schools in the country, may have been the first one that was Buddhist, and very famous from the 1970s, a key part of Boulder. MacAndrew teaches at Boulder, so he was a Naropa professor. Jerry may still be, has for a long time, been chair of Naropa. And you kind of go on his website, and he’s — for high achievers, for entrepreneurs, for people that are athletes, again, serious high achievers, and you read it. And it’s like the mix of high-achiever and Buddhist. And it kind of jumped off the page at me. And my response was, “Yeah. Okay. What the fuck? I’ll try this.” And it’s been great.

And by the way, when I say it’s been great, I’ve had plenty of really crappy sessions. I’ve had plenty of moments where I didn’t want to go. I’ve gone through phases where I passively avoided things, oh, I’m too busy. I need to cancel this one. I’ll see you in two weeks. Lots of my own shit getting in the way. And MacAndrew is very, very patient through all that.

Back to your question. I have recommended many, many people now to him, not to him as a therapist, but to him as a referrer. So one of the things that I find as a really useful thing is, and it comes from my experience here, if you were thinking about getting therapy, and you don’t know where to go, and you’re scared, or you’re sort of stuck, or you just don’t know where to start, finding a friend or a colleague that has done therapy, asking them if you could talk to their therapist to have their therapist refer you to one of their colleagues. Most therapists will do an hour session or a 50-minute session with the idea that they’re not your therapist, but they’re trying to make a few referrals for you.

The other place, if you have a good doctor, that’s general practitioner who you feel comfortable with, most general practitioners will have a network of a couple of therapists. And one of the mistakes I think people make is they feel like whoever they get referred to first is the person that they should work with.

Tim Ferriss: Their homework assignment.

Brad Feld: Yeah. And that’s the key. It’s not that. What you’re really doing is you’re shopping. And you’re asking even the people you’re talking to, who they think you should talk to. Now, if you’re in incredible distress, you might just land with a person. But if you’re in a place where, I really want to make progress here, asking the referral to the referral is a useful technique.

Last comment I’d make on this. Therapist and coach are totally different things. And it’s really important to recognize that, especially for the entrepreneurs or business people listening to this. Coaches are really valuable, totally different thing than the therapist. And there’s a lot of value, actually, in having both a coach and a therapist, especially if you’re leading something and you’re looking for how to get better at leading something, while understanding yourself better.

Tim Ferriss: What is the role of therapist versus coach for you? Is the therapist the salve and the coach the whip? Or actually I’m being facetious a little bit.

Brad Feld: Like looking for Monopoly pieces. Here’s how I describe therapy, and here’s how I describe coaching. For therapy, I pay somebody or if you have insurance, your insurance pays somebody. You pay them to sit and listen to you for 50 minutes. You’re going to, in my case, I go to Planet Brad. And if I want to talk for 50 minutes uninterrupted, he has to listen to me. And it gets pretty boring, talking for 50 minutes and having somebody look at you all the time. Sometimes it’s not. But if you do it week after week after week, eventually things start to shift, and the therapist is guiding you to go deeper, to explore and understand what’s actually going on, and what’s at the root cause of what’s going on, and how your lived history is impacting your current behavior, and on and on and on. So it’s really very much you showing up and the therapist, over a long period of time, helping you deconstruct yourself across all dimensions, but with you as the central focus.

A coach, and that word deconstruct is important because it’s deconstruct and presumably reconstruct in ways you want. If anybody’s ever done any kind of athletics, it can be junior high school athletics, you had a coach, and that coach helped you train. And that coach helped keep track of what was going on. And that coach gave you exercises. And that coach had an emotional relationship with you, as he or she tried to help you become better at whatever your craft was. And really, the coach is focused on you and your craft, whereas the therapist is focused on deconstructing you and your lived experience. There are many other pieces of that, but that’s generally how I think about it.

Tim Ferriss: Yeah. It sounds like inquiry versus prescription.

Brad Feld: Salve and the whip is kind of okay. The coach is the whip, the coach is the one saying, “Come on.” But a really good coach is also — there’s part therapy. Jerry talks about, to be a great — the Reboot way is a combination. Their methodology as a coaching firm is a combination of two things. One is radical self-inquiry, and the other is practical skills development. And I think this is what’s unique about Reboot is you can’t have one or the other. If you just have radical self-inquiry, that’s therapy. Go to therapy. If you just have practical skills development, you’re probably not going to get that much better. You can read books, you can go to seminars, you can do online courses. It’s the —

Tim Ferriss: Or you might get really great at doing the wrong thing.

Brad Feld: Really, really great. I like that. Really great at doing the wrong thing. It’s the intersection of those two. Or really great at doing something that you fucking hate.

Tim Ferriss: Right.

Brad Feld: You hate this, but you’re really great at it. But I’m not doing any radical self-inquiry, so I’m not going to acknowledge that I really hate it. So I’m just going to be miserable all the time. That’s no way to live.

Tim Ferriss: You mentioned CBT earlier. I just wanted to give note to one book for anyone who wants to explore CBT. Certainly you can find a good summary on Wikipedia, but there’s a book called The Philosophy of Cognitive-Behavioral Therapy (CBT), subtitle Stoic Philosophy as Rational and Cognitive Psychotherapy by Donald Robertson, which I found to be quite interesting. So for people who are curious about CBT as I am, that is a good resource. I want to ask you — and we’re going to get there about Boulder, why Colorado versus the Bay Area, for instance, after Boston. But I first want to ask you first, just to knock this out of the way. Number three. Why number three?

Brad Feld: So here’s how OCD works. We all have obsessions and compulsions, just the normal way our brains work. The problem is when you have an inappropriate linkage between the obsessive thoughts and the compulsive behavior. So you have an obsessive recurring thought, and you then execute a compulsive behavior that has no correlation to it. But it’s your effort, as a person with OCD, to try to control your environment.

Examples would be — and this is why one of the things that people with OCD have, is they’re known as checkers or counters. They count things, they’re constantly checking things or arranging and ordering things. And people will say, “I have OCD,” when they’re orderly and clean. Orderly and clean is not OCD. It’s only if, “If the thing isn’t orderly and clean, my mother will die. If I don’t eat this carrot in three bites, I will lose a client. If I don’t straighten all the cigarettes, so that they’re parallel to the street, as I walk from my apartment to my office in Boston, while touching all the signs with my right hand, my wife will have an affair.” That’s OCD.

On top of it, just the last example, the absurdity of it is most people with OCD are very germaphobic and don’t like dirt. Wash your hands a lot. And so the whole idea of trying to straighten all the cigarettes on the street and touch all the dirty sites on the way to the office is just stupid. But that’s what it is. And you have this immense cognitive load in your head that’s around this anxiety, and it’s really all just this effort to control one’s environment. So the trick to OCD is breaking the link. So we still have obsessions; we still have compulsions.

My favorite number is three. I don’t know why. However, it became my number. And so I had to do everything three times. When I got to my apartment at night, I had to turn the lock three times before I walked in the apartment. I had to jiggle the door handle three times when I closed it. I had to turn the lock three times when I closed it. When I took a shower, I had to turn the shower on, off, on, off, on, off, before I could get in. And then I had to turn it on, off, on, off, on, off after I got out. And then after I got out, because three is my magic number, I’d have to turn it on, off, on, off, on, off again. And on and on and on.

If I didn’t do something three times, here’s one of my engineer brain kicks in, I had to do it nine times.

Tim Ferriss: I love the combination of OCD-inflicted superstition and engineering! That’s great.

Brad Feld: Engineering and numerology. All right, so what happens if I screw it up when I don’t do it nine times?

Tim Ferriss: Oh, no.

Brad Feld: 27 times. Three times three times three. If you have ever had to do something stupid, that is — stupid’s the wrong word. If you ever had to do something, you’re trapped, you can’t go do the next thing. You have to do it 27 times. You get it right. Because if you don’t get it right, you’re going to do it 81 times. And there’s just some things in life you don’t want to do 81 times in a row.

So that’s how three became my number. And for some reason, interestingly, I care a lot about symmetry. So in some ways, four would have been a better number than three. Obviously, two would have been an easier number, but somehow it ended up being three. So I just carry it around with me. It’s my magic number.

Tim Ferriss: So if we’re talking about links and breaking these artificial causal links, let’s talk about another, what seems like a pattern interrupt, and that is your life dinners. Can you describe what these are?

Brad Feld: Yeah. This was another thing that came out of me and Amy’s weekend in Rhode Island. So she said to me, as we’re walking, “I want to have dinner with you once a month. Not a date night, but let’s do dinner once a month. Let’s do it on the first night of every month. And I just want a commitment for that.” And I hem and haw, “Oh, gee, I don’t know whether I’ll be in Boulder or Boston or New York or the Bay Area or whatever.” And she looked at me and she said, “Do you have a calendar, an online calendar?” Knowing full well I did, of course. And I said, “Yeah, I have an online calendar.” She says, “Does it have the ability for you to make a recurring calendar appointment?” I said, “Yeah, the online calendar lets me do that.” She says, “How about if you make an online recurring calendar appointment from 6:00 p.m. Colorado time to 10:00 p.m. Colorado time on the first day of a month and have it repeat forever?” I said, “Okay, I guess I can do that.”

So we did that. And so every month on the first day of the month, we have what we call life dinner. Now, 20 years of life dinners later, so what is that, 1,000-something life dinners, which is awesome, by the way, we have a little flexibility. There are definitely nights where we will have it on the second or the third because something’s going on. But we really commit to it. We used to go out to dinner. Now, a lot of times we just do it at home. Time of COVID, we for sure do at home. We often, not always, but often start with a gift exchange, and the gifts could be trivial little things. Once she gave me a remote control fart machine. She’s picked up a lot of jewelry and art from it over the years and books. One dinner she gave me a Range Rover. So it’s a full spectrum of little to big.

Tim Ferriss: I really hope it was the same dinner that you gave her the — oh, no, you didn’t give her the fart machine. That would have been less popular. Right.

Brad Feld: I think the Range Rover was to make up for the fart machine, but the fart machine was years earlier. And we sit down, and if you’re a fan of software development, and you know what Agile is, we essentially do — the first half is a retrospective of the previous month, and the second half is sprint planning for the next month. So again, very deliberately not a date night. We have plenty of those. This is let’s talk, each of us, you go first, or I go first, doesn’t matter, about the last month, and what happened, and what was good, and what was bad, and what we were unhappy about, and what we wish we’d done differently, and what we regret, and what we’re really satisfied with, anything. Just retrospective.

This powerfully interesting — because we started to learn that if Amy did something that really annoyed me on the 21st of the month, in the moment, I didn’t have to react and cause us to have a three-hour personal meltdown on the 21st of the month. I could wait nine more days or 10 more days, and it could be — 11 more days. It could be part of our life dinner. And it gave us a marker for being able to resolve the conflicts that we would have with each other or express things, positive and negative, that we hadn’t said in the moment.

The forward sprint planning part of it is not go through the calendar for the next month, but talk about goals, aspirations, what we might want to do differently, what we’re feeling in the moment that’s making us uncomfortable about the future, what we’re not afraid of, what we’re worried about happening in the future, what’s causing us, in the moment, real anxiety about the future. And anybody out there has had any therapy or done meditation, literally just naming the thing oftentimes gets rid of a lot of the anxiety. Just labeling it, just calling it out, and saying it out loud.

And so these dinners, sometimes the conversation, the life dinner part of the conversation might go five or 10 minutes, and sometimes it might go three hours. And sometimes there was laughter and sometimes there were tears and sometimes there were both. And it’s just such now, 20 some odd years later, a comfortable way to reground ourselves as a couple, roughly every 30 days, in what is a very, very challenging and complicated world.

Tim Ferriss: Now you mentioned earlier that Amy has a temper, and in my relationship, I suppose I’m the one with the temper. Do you have any ground rules for the details here? Or communication style? Because certainly, in any relationship where one person has a temper, at least in my experience, the delivery can matter a lot. Have you guys learned anything about communication style, when you’re bringing forward grievances or anything along those lines?

Brad Feld: Yeah. I think we’ve learned a lot over the years because we used to not be very effective when we fought. Because we didn’t know how. And any couple that says they never fight is totally full of shit. Because we’re humans. And we learn — I think there’s probably three things to pull out, as I think about them in real-time. The first is no violence ever. No physical ever. In any scenario. It’s whatever the — red line is the word. It’s just an uncrossable line. No physical violence.

Tim Ferriss: And by that, you mean physical striking or you mean pounding the table? Anything like that? Just that physical manifestation of anger?

Brad Feld: Yeah. Physical manifestation, pounding the table, throwing something, even if you don’t throw it at the other person, a sincere threat of violence, those things are not okay. Pounding the table, but there’s a big difference, I think, between pounding your fist on the table out of frustration and doing it in a way that — jerking someone’s chair. I think pounding a fist on the table probably would be okay in our — I don’t know if that’s — but certainly jerking a chair or shoving the other person or whatever, completely unacceptable. Not even sort of not acceptable, just completely unacceptable.

Second is don’t shut down while it’s happening. If you’re the one that’s being attacked by the angry person, it’s extremely easy to shut down. And I find myself, by the way, in many situations that I have outside of my relationship with Amy, including work situations, when I’m experiencing someone who has what I think is extreme or inappropriate anger in a moment, I find myself shutting down. I don’t know how to deal with it in the moment. And we’ve made a commitment to each other that you don’t shut down in the moment. I don’t storm off and slam the door and lock myself in the room. You sort of have to let it play its course and let the person — 

Tim Ferriss: What do you do instead, if I may ask, instead of shutting down? Do you have an alternative? So for people who might be inclined to withdraw into themselves and just kind of blank out, like WALL·E shutting down, if they feel like they’re being pummeled, how do you counter — what’s the countermove?

Brad Feld: There’s a couple. One is I try to stay in the moment with the anger. And again, I think this is a function of trust. The more you trust the person, the more you can do this. If you don’t trust the person, it’s impossible to do this. And there’s a spectrum. I completely trust Amy 100 percent. So I know that she is angry at me, and I know that the anger will run its course. So I also happen to know that when she’s angry at me, she’s usually scared for something that’s going on around me or her. And so in a lot of ways, it’s better for me to listen carefully, to try to figure out what it is that’s causing her to be scared, versus apologize for the thing that she’s angry about. And so in the moment, rather than trying to fix the problem that she’s angry about, I try to bring my full attention to the situation, to understand and ask questions, not in a Socratic and annoying as shit way, but in an engaged in the moment way, to try to understand what’s really going on.

Versus trying to defend myself. I didn’t do that. I didn’t mean that. That’s not what I said. That’s not what I meant. That kind of stuff, which is pretty natural reaction and really hard to hold back on, especially when you’re feeling falsely accused, which happens a lot when somebody else is angry at you. They don’t understand this whole situation. They don’t really know what’s going on.

And the third, then — so staying deeply engaged then leads to the third. Or the other tactic, by the way, I use is I try to use humor in those moments. We have lots of stories of us ending, as she gets out of an angry phase — I hate to make her sound like a terrible person. She’s awesome. And she doesn’t get angry very often. So it’s not that I live huddled up in the corner of my house, waiting for the next outbreak. It’s quite the opposite. But in those moments where all of a sudden, I’m jumping up and down with her in the air, laughing and making jokes about things and spinning in circles. Or I’m doing something silly, and she can no longer keep being angry because I’m just being silly in this moment. But I’m being silly, not as a reaction, I’m being silly because I’ve kind of landed finally on what’s got her stirred up, and it’s spurted it out. So it’s kind of like, oh, that’s the thing. Okay, here, let’s see how many potato chips I can stuff in my mouth now. And that’s going to cause you to stop being angry. Or whatever. Something cute.

And then the third, and this is critical, is that when it’s over, we both apologize. It’s not it’s not hers to apologize to me, and me to apologize to her, but we both apologize. And it’s a real apology. It’s not an, “I’m sorry you got angry at me,” kind of apology. It’s not an apology!

Tim Ferriss: It’s always a winner.

Brad Feld: Right. It’s total bullshit. Right?

Tim Ferriss: “I’m so sorry you’re responding poorly.”

Brad Feld: Right. It’s just simple. It’s “I’m sorry,” and “I’m sorry,” and hug and you go on. And I should also say, I get angry too. It takes a lot. It doesn’t happen very often, but I get angry too. And she does the same. She reflects it back. Engages fully. Listens. Of course, I’m sometimes defensive. Of course, she’s sometimes defensive. But you try to let that work its way out without disengaging. And then at the end, when it’s calmed down, you apologize to each other.

Tim Ferriss: Do you guys take any — and maybe in the early days, this would be a better question for reflecting back on the early days, since I’m thinking of, say, me and my girlfriend, I’m thinking of couples who are listening to this, or partners for that matter, who might want to, in some fashion, emulate this. Notes, taking notes. Helpful? Hurtful? Otherwise? Do you have any thoughts on taking notes? If there’s any sort of looking forward, planning, et cetera, is it helpful to have notes or do you guys prefer to do it all verbally?

Brad Feld: Yeah. For us, it doesn’t. I think it can be very helpful. I think it’s very, very individualistic. I am not a note-taker. I’m just not. I have a good memory, but I also have a memory that’s a synthesizing memory, versus a factual, detailed memory. And so taking notes actually clogs up my ability to synthesize things. And so I’m also a very good reader, and I learned by reading. So I’ve sort of learned about myself that the — a lot of people say, if you write it down, if you take notes, it’ll cause you to remember it better. What I’ve found for many things, not all things, but for many things, it actually interferes with my ability to synthesize what’s going on in the moment.

And for Amy, she is an extremely good — she has eidetic memory — an extremely good memory — which works to her advantage most of the time, because she’ll remember the incident better than I will. But also works to her disadvantage because it’s often not the details of the incident that is the issue. And we’ve learned that remembering and keeping track actually gets in our way of synthesizing and figuring out what’s going on. I think that’s a function of a long relationship, too. And just very, very deep trust. I can imagine earlier in a relationship or earlier in our relationship, that might’ve been helpful.

The other thing which comes from that is a lot of people, and we see this in business all the time, you see this in — hey, you read a book, you see it in someone’s book. It’s not that they make the point one time. They have to make the point three or four times. And sometimes, you have to read the point three or four times before you actually understand the point. And there is a reason that there’s sentence structure, paragraph structure, chapter structure in business books that can be tedious and result in the business book only [needing] to be about 20 pages long. But for many of us, we have to cycle through a few times.

And I think that’s especially true in conflict, because when you’re confronted with conflict, the first thing that you see or respond to often is not the source of the conflict. It is often not either the root cause, the thing that’s even triggered it. And the person who’s angry may be articulating their anger in a way they think resembles what’s going on. But you’re probably not hearing what they’re saying properly in that first moment, because you’re trying to get oriented in dealing with your own fight or flight reaction. Especially if it’s someone that you have an intimate, trusted relationship with. If it’s just some random person, different.

So I know that’s sort of a circuitous answer. For me, writing stuff down is not helpful, but I can see how for some couples it is. I think the practice, also by the way, of the retrospective. Okay. You had the fight, don’t go off into your corners and each sit down with your journal and write what just happened. But agree to sit back down, especially early in a relationship, agree to sit back down on a couple of days. Three days from now, let’s have lunch, and let’s talk about this. And between now and then, let’s each in our own way think about what was really going on and have those conversations.

And I know that Amy and I have had many of those types of conversations over the last 20 years on our life dinners, on our week off the grid. That is part of the content. We’re no longer talking about is our relationship going to work and why our relationship isn’t working. We’re talking about the next level of it, where we’re actually exploring what’s going on with each of us as individuals, in these moments where things don’t feel good or when things — oh, by the way, the other end of the spectrum, feel really good.

Tim Ferriss: So there’s all sorts of stuff that I want to cover, and I think we’re going to probably run out of time. I am going to come to the Colorado versus other options, but just very quickly, the digital Sabbath. Going without email, without phone from Friday night to Sunday morning, how often do you guys — what’s your hit rate on doing that, would you say?

Brad Feld: 80 percent of the time?

Tim Ferriss: That’s incredible.

Brad Feld: Four to five, three out of four, four to five. It started — I didn’t use to do it. I used to work — my work rhythm was that I would use half a day on Saturday to catch up, usually in the morning. And then I’d do a long run on Sunday mornings, usually. And then I probably work another half day to full day on Sundays. And even into 2013 — the number of hours per week, again, thankfully, I stopped having to keep track of the number of hours a week I worked. In about 2002, Amy didn’t make me keep doing that for the last 20 years. But I would go through phases where the total number of hours a week I worked probably diminished, if you didn’t count things like travel, and you didn’t count things like all of those hour or two-hours in front of your computer, just catching up on stuff. Which is easy to dismiss that you’re actually spending time working, versus living or rejuvenating yourself or taking care of yourself.

So when I had this depressive episode in 2013, I had done plenty of, again, weeks off the grid. Amy said, “Why don’t you take a day a week off? Just don’t work a day.” By the way, when I was depressed, I was having trouble getting out of bed. So it wasn’t like that was a hard thing to agree to. It’s like, yeah, that sounds great. And I’m not religious, but I’m culturally Jewish, the Jewish tradition. I’m like, you know what, I know plenty of very successful religious friends, religious Jewish friends, who take the Sabbath off completely. Friday night to Saturday night. And so I just said, I’m going to apply the week off the grid to Friday night too. And I do it till Sunday morning. Because I found that if I got back on the grid Saturday night, that was kind of silly. From my frame of reference, kind of defeats the purpose.

And we kind of use sundown as the trigger, although it’s not a hard boundary, and Colorado in the summer, the sun doesn’t go down until 8:30 right now. We have a place in Alaska. Sometimes when we’re in Alaska, the sun doesn’t go down till two in the morning. It’s not quite the right trigger, but it’s kind of the point where I’m like, you know what, I’ve had enough, I’m done. And I’ll pick this back up on Sunday. And what I’ve found over — I’ve been now doing this for many years. When I go out of phase with it for any period of time, and I had a period at the beginning of the COVID crisis where I was spending a lot of my time working on stuff on the private sector side, but for the state of Colorado, as we were dealing with a bunch of stuff on both the health side and the economic side and dealing with some stuff on the mental health side, and just trying to rally a bunch of people in the private sector to help the state. And specifically, we have a fantastic governor in Colorado, Jared Polis, who’s a very successful entrepreneur and a good friend.

And sort of in that period, I think I skipped three weeks. So I worked all day Saturday, all day Sunday. And by the end of the third week of that, I was broken. I could feel I was done. I wasn’t going to make it another week unless I took a break. And so in a lot of ways, it’s helped me sustain a pretty heavy work intensity over a long period of time by really completely disconnecting for that 24-hour period.

Tim Ferriss: Yeah. For some period of time, actually for a long period of time, I was doing screen-free Saturdays to the best of my ability. And I would use Google Maps for certain things. But outside of that, really texting to coordinate, meeting up with friends and Google Maps, outside of that, it was browser free, laptop free. And you really do notice the gear shift, or I should say the gears grinding when that gets removed for any extended period of time.

Brad Feld: Here’s the flip side of it that I think is so amazingly wonderful in some ways. I like to take naps in the afternoon. So I pretty much take a nap every Saturday afternoon. And I remember, this is a long time ago, I remember a Saturday afternoon and I’m a big reader and I just didn’t feel like reading. And I had gone for a run and I’d taken a nap and I was kind of bored, which almost never happens to me because I fill up my world with stuff all the time, right? I don’t allow myself the luxury of being bored because I always have too much to do, which is a whole ‘nother version of, it’s basically boredom aversion, right? I don’t want to be bored, so therefore I will find more stuff to do because I’m afraid of not having anything to do. That’s, in and of itself, got plenty of grist for the therapist mill.

And I said to Amy, “I kind of feel a little bored.” She laughed and she said, “Isn’t it wonderful?” And it is really helpful to sometimes just sort of look out the window or sit in your backyard and feel like, “I actually don’t have anything I have to be doing right now other than be right here.”

And for many people in today’s world, it’s hard to do. And so I’ve let that be part of it, which is, “Okay. I’ve got my day off on Saturday. Here are the three books I’m going to read and I’m going to go for a run. I’m going to make sure I get all these things done and I’m going to — ” That’s not what it’s for. It’s for just take a deep breath, reflect, and let the day unfold.

Tim Ferriss: You mentioned reading. All roads lead to Colorado in this question, I keep promising, but you mentioned reading. I have a list here of some of your favorite books and I’m just going to go through them real quick and then ask a quick question on this. Zen and the Art of Motorcycle Maintenance by Pirsig, Battlestar Galactica, Ronald D. Moore, Snow Crash by Neal Stephenson, Neuromancer, William Gibson, and if I’m getting this title correctly, The Startup Community Community, is that right, by Mighty Networks.

If we’re looking at the first four, which are all fiction and you are recommending one of them to someone who has been a nonfiction purist for a long period of time, is there one that jumps to mind as the starting point?

Brad Feld: So let me re-segment that a bit because they’re not all books. So Battlestar Galactica — 

Tim Ferriss: I wasn’t sure.

Brad Feld: No, TV show. 

Tim Ferriss: I wasn’t sure if it was based on a book.

Brad Feld: But it’s worth touching on that. And then The Startup Community Community is an online community that I just started a couple, maybe 10 days ago, from the time we’re talking, that’s part of the new book that I’ve got coming out at the end of July called The Startup Community Way. I’ve been obsessed about the idea of startup community since I wrote the first book around that in 2012 when the phrase “startup communities” didn’t exist.

And so a thing I’ve wanted to exist since I wrote that book was a community for anyone around the world that was interested in startup communities, which is most entrepreneurs, but then lots of other people and nobody had ever created it. So I just decided to create one. And I’m using a tool called Mighty Networks that’s really quite interesting and well done. And in a very short order of opening it up to people and it’s public, so anybody can join it, it’s been amazing to see some of the conversations and the level of engagement.

To your question, of those three books. So, Pirsig’s book is Zen and the Art of Motorcycle Maintenance is a book I think anybody who makes anything should read. I recommend it to all entrepreneurs. I read it when I was in high school and I’ve read it every couple of years since, probably read it every three or four years. I listened to it on tape, book on tape once when I was training for a marathon, just to see if it sunk in in a different way. It did.

And while it’s fiction, it’s sort of fiction memoir-y philosophy, and it’s fiction like memoir is fiction, right? Fiction is the wrong word for it. It’s memoir-y philosophy. And the essence of the book is the notion of what the definition of quality means, but using a series of different things that are happening to the protagonist and narrator, who is the author, over a period of time where he descends into madness against the backdrop of classical philosophy.

So it just combines a bunch of things in a very powerful way that you don’t get the full value of it the first time, but it’s easy to move through. So, I just, I think that’s a book every human being should read.

The two books I listed there, Snow Crash and Neuromancer are important books because they essentially are the books that created, that presaged the context we have today. Neal Stephenson and William Gibson are two of my favorite and two of the best contemporary science fiction writers.

Neuromancer was first. It was written in 1984. And if you read it today, you’d kind of go, “Ah, whatever.” But if you time travel back to 1984 and read it, given our world in 1984, it will blow your mind. How he predicted, and whether it’s 2000 or 2010 or 2020, just the number of things that he got right as a predictive force in our not too distant future, not just technology, societal issues, humans against interaction with artificial intelligence, the dynamics of society, how politics work, how drugs work, long, long arc of things.

Snow Crash is written in 1992, so just before the World Wide Web begins. And I think the technology part of Snow Crash is brilliant, but even more powerful is the geopolitical part of Snow Crash. And the geopolitical part of Snow Crash is so incredible against the backdrop of 2020 and nationalism. And the idea, for example, that states, if you had said to somebody a year ago, states in the United States of America are going to start closing their borders to other states, the person would say, “You’re fucking out of your mind.” That if you were from Texas, you are not going to be able to travel, you’re not going to be allowed into New York like, “Huh?” And so, I mean, this book goes way more granular than that in terms of the boundaries, but it’s awesome.

By the way, another book in that vein that I think is as good or better a book, also the first book was written in the early 1990s, I believe, by a guy named Dan Simmons is a book called Hyperion. It’s actually four books, The Hyperion Cantos, and it takes place over about a 300-year period. And again, all of these things that are folded together, it’s not just science fiction, but it’s AI versus human. It’s religion. It’s society. It’s gender. It’s augmentation. It’s geopolitical, I’ll overuse, right? But the idea of all of these things happening and the first book is so wonderfully fun because it’s written in the style of The Canterbury Tales. So it’s a pilgrimage where the first book that’s the setup for the whole series is the seven protagonists in the first book telling their stories as they’re going on a pilgrimage that, of course, has a very meaningful climactic end that motivates you to read the second book.

The reason Battlestar Galactica is on that list is I don’t watch TV that’s broadcast TV. I didn’t watch TV as a kid. My parents let Daniel and my brother and I have one hour a day. I liked to give my hour to my brother. I’d rather read a book. However, I like to watch TV that are series and I like to watch dramatic TV.

And there’s a few shows that are now classics that I missed the first time around that I watched in the last 10 years and Battlestar Galactica, or BSG, is one of them where it’s a great space opera, but it’s not about being a space opera. It’s once again about humans and machines and the interaction between humans and machines and the dynamics of the evolution of our species, the human species and the machine species, call it whatever you want. And then everything that happens around all the boundaries of humanity and society as a result.

And the reason I like these so much, and I’d put them so much at the top of the list for a somebody who’s a nonfiction reader or anybody that just wants to dig in is that the best part of science fiction is world-building and science fiction authors that get the world-building right and really know how to do it, the books that they write are just truly, truly incredible. And it’s not even that you lose yourself in it, but they cause you to think about your own world in a totally different way.

Here’s one more, I’ll give you two more contemporary writers to play with that are in this category. N. K. Jemisin, who’s a black woman who’s unusual in the world of science fiction because I think most people think of science fiction as the domain of white men, has emerged as one of the absolute best world-builders ever. And her ability to construct these engaging incredibly complex narratives that don’t just get you lost in the story, but cause you to really reflect on your own existence and what it means, and what’s meaningful or not meaningful about certain elements of it, off the charts.

Another person who’s become a close friend, I helped sponsor him when he was writing his first couple of books, he’s now I think on book eight or nine or 10 that’s really emerged now, I think, as a really great writer, and becoming a great writer of any sort is a craft. You got to do a bunch of it, as you know. And you write a bunch of shit, you write a bunch of shit and then eventually it starts to be better, and less shitty. And sometimes it’s really good. And then sometimes you write something and it’s not so good. And then you try again on the next thing you do. There’s a guy named Eliot Peper. And Eliot has become in a category called near-term science fiction writers that guys like William Hertling and Daniel Suarez are in, which are things that you could almost imagine are happening right now, almost, like just around the corner.

And so it’s so accessible, but then it’s so provocative because of the thing that happens and the way it causes you to think and reflect back on how your current existence is. So there’s some books for you.

Tim Ferriss: Plenty, plenty to start with. I want to underscore a few that you mentioned. Snow Crash is a spectacular book. It’s such a fun book to read also on top of it. And for world-building, I just want to throw another book in if people aren’t overwhelmed already, which is Dune.

Brad Feld: Yeah.

Tim Ferriss: Frank Herbert, in terms of world-building, it’s a mind-blower.

Brad Feld: It’s classic. It’s classic, right? It’s the beginning of the beginning of that genre.

Tim Ferriss: I feel like you can learn almost all the leadership lessons you need from Dune. It is just truly a spectacular work. And two other — 

Brad Feld: I’m going to toss one other on the pile, too, for fun, that’s contemporaneously relevant for anybody that wants to explore how badly things could go in the time of COVID if this turns into the dystopic future reality, rather than the optimistic everything goes away and we’re back to normal of magical thinking.

It’s a book called The End of October. It’s written by a guy named Lawrence Wright, and it came out in April of this year, April 2020. And so he had to be done with it in February, so before the current pandemic probably had, and COVID had probably very little to do with the book.

It is so good and so terrifying and so real on so many levels in terms of what we’ve dealt with and how we’re dealing with it. And of course he goes and tells the whole story, right? So it ends up in this dystopia ending really, really dystopic ending. But the first 25 percent of the book is about where we are right now.

And for anyone who likes, again, I put this in the category, it’s not science fiction, but it’s near-term, right? It was written about a global pandemic that could happen in the future. Oops. It got published as that global pandemic was starting.

Tim Ferriss: It’s eerie, isn’t it? Kind of spooky. Two last ones, just because you’re definitely pressing all the right sci-fi buttons here. Two more authors who were recommended to me that I’ve just fallen in love with, one is Ted Chiang, C-H-I-A-N-G. He has his two collections. The [movie] Arrival, which I think is fantastic, was based on one of his short stories, which for a language-obsessed person like me is just how language structure is thought was brilliant. He has a new collection called Exhalation that I highly recommend to people.

And then Ken Liu, L-I-U, The Paper Menagerie, which was gifted to me by Matt Mullenweg, really accomplished tech founder, CEO of a company called Automattic, M-A-T-T-I-C. You might see Matt Mullenweg, Automattic. In any case, both of those are short story collections so you can dig in and you don’t have to commit to a marriage of a reading marathon, which you might feel if you pick up Dune, I still recommend it. But The Paper Menagerie and Exhalation are easy ways to kind of play in the shallow end with deep meaning without getting overcommitted.

Colorado. Why move to Colorado? You’re in the tech game, you’re a tech investor, you’re a tech entrepreneur. It would seem that all roads, in fact, should lead not to Rome, but Silicon Valley if you want to be in the epicenter of all the activity and deal flow and blah, blah, blah, all that stuff. Why move to Colorado from Boston?

Brad Feld: It’s a couple of reasons. One is I think actually the word epicenter is a good one. I’ve never really wanted to be in the epicenter of anything. It’s not my thing. I am more of a loner than a joiner. I am more of a detached or disconnected from a sort of in the middle of a kind of person. So I think epicenter is an interesting word to sort of underscore in the context of this.

I grew up in Dallas, Texas. Amy grew up in Fairbanks, Alaska. We met in Boston. We lived in Boston for 12 years. Boston was very good to both of us, but I like to describe living there for 12 years as living there for 11 years and 364 days too many. It was never home. It never ever felt like home to me. And when you’re in college and you’re in your early 20s, the definition of home is tricky, right? Like what does that actually mean? What is home?

When I was in college, I actually would say things like, “After I get done with college, I’m going back to Dallas,” which my parents would love, but I had zero interest once I got to my third year of college of moving back to Dallas. I’m like, “Nope, that’s not happening.”

So we complained as a couple, we complained to our friends regularly about Boston and how we were going to leave and get out of Boston someday. And I think our friends just thought we were all like, “Yeah, whatever, we hear you, but whatever. You’re not seeming to take action against that.”

And when I sold my first company, I was 28. And I told Amy that by the time I was 30, we’d be out of Boston. And we traveled a lot together and we liked to explore different places. And she said her requirements were ocean or mountains. And growing up in Dallas, I didn’t have either. So I didn’t totally get that. But I’m like, “Okay, well, not both, either, right?” And she’s like, “Either. I need one or the other.” And growing up in Alaska, she had both. And about two months before I turned 30, she said to me, “I’m moving to Boulder and you can come with me if you’d like.”

Tim Ferriss: That’s a strong hand.

Brad Feld: We’re married, right? And I’d sold my company. I was still working. I was doing lots of angel investments around the country. I was still, I was traveling a lot West Coast, East Coast, Boston, New York, Seattle, San Francisco, L.A. Occasionally somewhere else. We had been to Colorado a lot. She’d lived here when she was in third grade and I had come here skiing as a kid some and then as a young adult some. And Colorado was just sort of the fantasy of it was a cool place.

The rugged, rugged West is kind of a thing in our culture, independent of what you think about Atlas Shrugged as a book or Ayn Rand as a philosopher, like the whole idea of Galt’s Gulch being in Colorado sort of stays with you. And this idea that it’s away from all the other stuff, right, so not the epicenter. That kind of appealed.

And we’d been to Boulder. We went to Colorado for a two or three-week trip. And we’d been in Boulder like on a December, January day, that was like 50 degrees on the Pearl Street Mall and it was a beautiful winter day that was not really wintery, kind of like, remember this, this is pretty awesome.

So she told me we were going. I had a staff job for the company that I worked for so I could go anywhere. This was AmeriData, so it was easy for me to just relocate from Boston because I didn’t have anybody working for me anymore. And we flew out. We rented a house. We flew back. We told all our friends we were moving to Boston, we packed a truck — or Boulder. We packed a truck and we drove to Boulder. We knew one person, a guy named Vern, and he moved away within a year. So we really moved out here not knowing anybody.

1995. And our view, our goal was nothing, zero to do with work. Our goal was to build a life here. We said, “Let’s evaluate whether this is the place we want to build a life. And if it isn’t, we’ll try something else. And if it is, this is our place.” And within six months we knew unambiguously that Boulder was where we wanted to build our life.

We bought a house behind a state park in a place called Eldorado Canyon behind Eldorado Springs State Park. We initially bought a piece of land with 40 acres and a house on it. Over time, we ended up buying the pieces of land around us and ended up having a little bit over a hundred acres there. We lived there for 17 years.

And eventually as we started to get a little bit older, we moved to the other side of Boulder, right on the edge of Longmont. We again have 40 acres and the land is an important point of this story, so I’ll get to it in a sec. And now we’re looking at the mountains rather than being in the mountains. And we have this real sense of expansiveness as we look at Longs Peak each morning. And we have two big golden retrievers and they just kind of run wild on our 40 acres whenever they feel like it. Although one is old and not running so wild anymore.

Today, I would be able to answer your question. When I was 30 I couldn’t. Today my answer is I don’t like cities. I don’t like being around a lot of people. I can do it. I can put up with it for a couple of days. We had an apartment in New York for three years and I probably spent a week a month in New York between ’97 and ’99, not necessarily a consecutive week, but over the course of a month. Two days, three days, that was okay. Same thing with San Francisco, three days, San Francisco, then I just want to get out of there. I can’t stand it.

But then the peninsula, I spent an enormous amount of time on the peninsula during my SoftBank and Mobius time. I lived most of the time between 1999 and 2006, when I was coming out all the time, I lived at my partner Heidi Roizen’s house in Atherton. I mean, it’s a beautiful place. It’s not my place. It’s not where I feel at home.

And I had formed with Amy, I think the two of us formed it together, a pretty deep belief that it was important to pick the place you wanted to live and build your life around it rather than go to a place that you felt like you should go to because there was an opportunity there.

And I’ve had this very long-standing belief, partly because I’ve started and invested in countries all over the US that you can create and build companies anywhere. That the ability to build startup communities and really vibrant entrepreneurial ecosystems, not just are important, and are you able to do them anywhere, it’s actually an imperative that any city with any critical mass, 100,000 people have a vibrant startup community.

And one of the things that’s been most powerful to me about Boulder, at least from the time period in 1995 to probably 2015, so a 20 year period for me, maybe a little bit longer, was I was in a place that was big enough to be interesting, 100,000 people or more, but small enough that I could get my mind around it and what was going on as I tried to understand the dynamics and the characteristics of building a vibrant startup community.

The last comment on why Boulder and there’s positives and negatives that I understand today having lived here for 25 years is both Amy and I are very socially liberal and Boulder is a very socially liberal place. So, in some ways it was a very comfortable place to come. There’s plenty of other socially liberal places in the country. And, of course, being in Boston is very polyglot so it’s pretty easy to be socially liberal there. But growing up in Dallas, not so much, right, different dynamic, and I was aware of that.

I was aware of the overwhelm that I felt when I was in Los Angeles, just Los Angeles isn’t a city. I had somebody tell me once the number of it’s 80 something cities in one thing called Los Angeles, like it’s just overwhelming in the same way to me that Manhattan is just overwhelming. And so it felt like a place that could be very comfortable against that backdrop.

Amy and I also have a house in Homer, Alaska, which is a town of 5,000 people. That’s where she grew up until she was eight. And we used to go to Homer for a month every year. We still go to Homer, but not as often, maybe every couple of years. And it’s again, a totally different yet another thing to live in a town of 5,000 people that’s 60 miles away from the next town that has 10,000 people in it. I like that so much better.

The negative, which I’m very aware of today, is something that Amy and I started to label a few years ago as an enclave. We just started to use that word. And we realized that it’s not a filter bubble. It’s not that, but it’s an enclave. It’s a very privileged place to live.

We built a house in Aspen a couple of years ago, and there was something that, we had a house in Keystone, Colorado for a long time. I love running in the mountains. We loved being in the mountains. There’s something about Aspen that we were drawn to because of the restaurants and the town, but also the ability to be in the mountains and just be disconnected from it all.

And we pretty quickly, we didn’t realize it till after we had a place there and were living there on a part-time basis that it was an enclave as well, right? And a whole different level of enclave in terms of privilege and the dynamics around it. And while there are elements of that that are appealing, there are many elements of it that are very disorienting, confusing, and not necessarily healthy for the city. And I understand those things much clearer today than I did even three or four years ago.

As I find myself living on the edge of Longmont, which is still a pretty comfortable place to live, but much more of a normal town than Boulder, I find myself spending more and more time away from big cities because of pre-COVID even lack of travel and sort of reflecting on what and where I like to be. And then most interestingly how our technology today has changed all that, right?

Pre-COVID if you had said to somebody, “90 percent of people who work in office buildings — or 95 percent of people who work in office buildings — are going to be working from their houses for the next three months,” the person would’ve looked at you and said, “Never going to happen. Impossible. Can’t happen. The technological infrastructure doesn’t exist.”

Well, guess what? All those people that said it couldn’t happen were wrong. We just lived that experiment and it worked just fine. Yeah, worked just fine, yeah. Incredibly challenging for many people, super disruptive on many levels. For some companies, really negative. For some companies, really positive. But from a structural sense could one who likes to be physically disconnected from others still be digitally connected to society in a meaningful way? I think we just proved that the answer to that’s yes.

So that then changes again the importance or relative importance of place in terms of how you build your life and what you build your life around and where that place is. I’ll end this rant with — there’s a word that I learned from John Hickenlooper, who was our governor for a number of years, now running for Senate and is also an entrepreneur. He was one of the people that basically helped create the microbrewery industry and the idea of a microbrewery in the first place.

And he, I don’t remember the first time I heard this word from, I think it was one of his state of the state speeches. He used the word topophilia and topophilia is love of place. And I think to be truly satisfied, I would say happy, but I don’t think that’s the right word. And I’m not sure satisfied is the right word either. So I don’t have the right word, but something that has that flavor, as a human, you have to end up living in a place you have topophilia for, that you have a love of.

Interestingly, if you can find a place that you have a love of that the constraints of living in that place are lowered because of the way that our society works, in a positive way that gives you even more flexibility. If you’re able to find places that are not as enclavey and are more inclusive, and that have different dimensions of diversity, including being able to time-travel to other geographies while still having that love of place for the people that you’re interacting with, so it’s not the physical love of place anymore that becomes the dominant. It’s a characteristic, an important one, but not the dominant, that gets even more interesting.

And I think we’re at the beginning of that shift in our society.

Tim Ferriss: Well, let’s talk about, I think that I would be remiss, or it would be remiss. I’m missing my grammar, but if I weren’t to ask you about something that’s come to mind for me because you and I have chatted briefly about it, and that is complexity theory, and I’d like you to even just define that. In The Startup Community Way, I mean, maybe it’s not in The Startup Community Way, but I’d just love to hear how you think about applying complexity theory, defining it first to life, to what you do, to problems.

Brad Feld: You’ve written a bunch of books, and I believe I have — I own and have enjoyed all of your books.

Tim Ferriss: Thank you.

Brad Feld: The thing that you know as an author is that a lot of times when you start working on a new book, you work on a new book for a while, and then you realize it’s total shit.

Tim Ferriss: I think that’s every book I’ve tried.

Brad Feld: It’s not just partial shit. It’s total shit. That was the experience that my co-author, Ian Hathaway, and I had about a year into working on The Startup Community Way. We had started talking in 2017, we met each other. I liked Ian. We’d done a few things together around startup communities, talked about a few things, had a couple of long discussions. He said to me, “Have you ever thought about writing a sequel?” I said, “I hadn’t really thought about it.” He said, “I think the world of startup communities and all the people I’m talking to, like the book, the 2012 book The Startup Communities, was really helpful, and it was foundational for a lot of basic thoughts about building startup communities.”

But I know you, Brad, get the question, and I know I, Ian, even though I’m not deep in this, get the question of, ‘What now? I’ve been at this for five years.'” Or you’re in a conversation with somebody in a city where their startup community has gotten to a certain level, according to their framing of it, but they’re really struggling with what to do to get it to the next level.

We decided to write a book that was a sequel, so we started writing the sequel. We wrote, I don’t know, a book like The Startup Community weighs 50,000, 60,000 words, probably write 25,000 words. We were both unhappy, and it was hard and we weren’t — there was no rhythm, there was no cadence to anything we were doing. Ian called me, he was living — he had moved to Boulder for a while and then moved to London, and he called me or sent me a note.

He said, “I have come up with a framework to use to describe what The Startup Community Way is.” I said okay. He said what a startup community really is, is a complex adaptive system. That’s all he said. I said, silence, and I said, “A hundred percent agree.”

Let me define that, and we have in the book and in general taken the liberty of, instead of calling it over and over again “a complex adaptive system,” we’re calling it a complex system. A complex adaptive system is a particular type of complex system, but for purposes of The Startup Community Way and for how people think about it, I think the idea of complex systems plenty, it doesn’t have to be the exact precise academic thing.

Think of three types of systems, simple, complicated, and complex. A simple system is making a cup of coffee. I listened to Seth Godin’s podcast with you recently, which was from a long time ago, but for some reason it popped up and I wanted to listen to it. I love Seth. I listened to Madeleine Albright’s podcast with you, and that really inspired me. I went back and I poked through and went looking for some other podcasts of people that I knew and I liked and respected and Seth’s was one of them.

He talks in the podcast, y’all talk about how he makes a cup of coffee and his obsession with how you make a cup of coffee. Making a cup of coffee is a simple system. There’s a recipe, there’s a set of rules. You can make a really shitty cup of coffee if you don’t follow the recipe quite right, or if you’re not good at the pieces of the recipe, but it’s a pretty straightforward thing. There’s different types of coffees, and there’s different modifications to the recipe, but it’s a simple system. You have an input and a deterministic output. Might not like the thing you taste when you taste the output, but it’s a deterministic output.

A complicated system, again, has a recipe or a playbook, but it’s got a lot of different steps and the steps can be done in different order, but you end up with a deterministic outcome. Doing your monthly, quarterly, or financial annual financial statements is a complicated system, doing a financial audit is a complicated system. It’s replicable.

Building an airplane is a complicated system. It’s really hard to figure out how to do it the first time, but once you’ve done it, you just keep doing it. 

A complex system does not have a deterministic outcome. You cannot predict the outcome from the starting point, and the inputs along the way, generate outputs that become inputs into the system.

There are lots of fun examples of complex systems, but the one that I think a lot of people immediately get is raising a kid. Because even if you don’t have kids, you were a kid, and if when you’re born, the day you’re born, your parents say, “This kid is going to go to Harvard, become a doctor, become a — dah, dah, dah, and we’re going to follow the rules for how to do that.” Chances are, the kid is going to be the opposite of that, just because of natural human being kid, or they’ll need a lot of therapy, one of the two.

There are many, many things that are complex systems, and the idea that you can apply a playbook or a rule book, or a recipe, or a sequence of steps that get a deterministic outcome, doesn’t occur. Interestingly, when we wrote this, and we had this a-ha, so we spent another year working on this. Now we both knew a fair amount about complex systems and complexity theory prior.

Ian had been fascinated by this, which is why he landed on it. I had been fascinated by it going back to the late ’80s, early ’90s, when I read a book called Complexity by, and I’m going to lose the author’s name. I want to say Marshall or Malcolm something, but it was one of the early books that came out of the Santa Fe Institute research and talked about Brian Arthur, and the idea of increasing returns, which are really just exponential curves. Talked about flocking behavior talking and — 

Tim Ferriss: M. Mitchell Waldrop, does that sound right?

Brad Feld: M. Mitchell Waldrop.

Tim Ferriss: Yeah, Complexity, subtitle, The Emerging Science at the Edge of Order and Chaos.

Brad Feld: Great, so that book I read. I remember laying on my couch in my apartment on Bay State Road, reading that book and it must’ve been 1990 or 1991, and just having my mind blown. It was just like, yep, yep, yep. And Conway’s Game of Life and sort of all the stuff that, from that around emergent behavior, contagion, positive and negative feedback loops, words that we throw around. Many people, by the way, throw around as though they know what any of it means, but then don’t act in any way whatsoever that reflects what those words mean.

I was always fascinated with it. If I have a r egret in terms of engagement, I regret that after I sold my first company, I didn’t go figure out how to get involved in the Santa Fe Institute, because I think it would have been super stimulating to me based on things that I like.

We went really deep on complex systems.

In the end, we came up with a book that uses the notion of complexity and the idea of complex systems as the fundamental core for understanding how startup communities grow and evolve, and differentiating very clearly a startup community from an entrepreneurial ecosystem, because they’re very different things. And what does that mean, and especially what does that mean over a long period of time, because again, if the inputs are becoming outputs, etc.

The thing that today to this moment is baffling to me in a horrifying and wonderful way, we are living in the middle of a crisis like none other I’ve experienced in my life. That is the essence of a complex system. The COVID crisis is not a crisis, right? It’s a health crisis. It’s an economic crisis that was generated by the health crisis. It’s a mental health crisis. 

In the US now we have a racial equity crisis, by the way, none of these crises are new. 

The intersection of these things is part of the essence of the complex system. Each of them on their own are complex systems. You do not have a deterministic outcome. There is not a playbook to follow. There is not a set of things that we can do that if we do them in the proper sequence, all will be good and we will finish.

In fact, the whole idea of finishing, and in some ways, the idea of defining good at any moment of time is temporal, because all of the things we’re doing affect everything else we’re doing. Back to this notion of, I love contagion in this context. There is an idea of positive and negative contagion, and COVID is obviously extreme, negative contagion. But in business, we talk all the time of positive contagion, the whole idea of a viral loop for anybody that runs any business that’s consumer facing is positive contagion.

If you scale it up to society, that’s what we’re talking about in The Startup Community Way. Literally, that’s what we’re talking about. You can scale it up to that level, or you can scale it down to how the startup community in Birmingham, Alabama is growing and developing in positive and negative ways.

Tim Ferriss: Yeah, I can’t wait to check it out. You mentioned The Startup Community Way. The second edition to Startup Community is I’ve watched these communities, vibrant communities, pop up in some of the last locations I would expect. For instance, Ottawa, Canada, when Shopify, which it was certainly one of my most successful investments, although I was an advisor as opposed to an investor.

You’ve seen how one company with the graduate/alumni, and the factors that made it such that it could develop this vibrant ecosystem are really fascinating. You’ve made the point before that, and please correct me if I’m getting this wrong, but you have many people out there who are trying to create the next Silicon Valley by looking at the current Silicon Valley. On some level, they should be looking at are the initial conditions, say 60 years ago, that provided the opportunity for all of these emergent properties to form what we now think of as Silicon Valley. But you can’t architect it based on the current view, so I’m looking forward to The Startup Community Way.

Brad Feld: Thanks. That last statement was exactly correct and super important. Your Ottawa example and your Shopify example is an example of what we refer to as entrepreneurial recycling. The idea is that over time, it takes a long time, as you have success in a geography, in a city, in a startup community, all of a sudden entrepreneurs have a new resource, which is wealth. If they care, if they have topophilia, if they care about their city, and it’s not just the entrepreneurs, it’s also many of the early employees.

In fact, many of the not-so-early employees end up with wealth, and an understanding of how economic wealth gets generated by creating something where nothing previously existed. Right before Shopify existed, there wasn’t a thing called Shopify. It was the product of a couple of founders and then a team, and then more people, and then more people and more people. Eventually today, an incredibly valuable company. Those people then reinvest not just their wealth, but their expertise into new companies in that community, and that recycling then follows generations.

The first generation of it’s interesting. The second generation, so when some of those companies become successful and those entrepreneurs and employees and people that work for them and leaders recycle their time, their expertise and their money, it continues to expand. If you go back to the initial conditions of Silicon Valley, that happened a lot over a long period of time. I would argue that — a line that Ian and I like to use is that, even Silicon Valley today couldn’t recreate Silicon Valley. It would be, by definition, a different thing.

That’s the essence of a complex system. You are creating a new and different thing and understanding the initial conditions and understanding the inputs, and not necessarily focusing on the people or the activities themselves, but the connections between all those things and how that then influenced where things went. It is powerful. I can’t not say this because it’s a fundamental part of my, what I call the Boulder thesis around startup communities, is that you have to take a very long-term view.

I like to say, I used to say, you have to take a 20-year view from today, or you have to take a 20-year view. Now I say you have to make a 20-year view from today, literally you always have to have a long-term view from the moment in time you are at. It never can get shorter. Then one day you die and you’re not part of it anymore, but that’s okay, because the next generation of people are taking that long-term view.

Tim Ferriss: Yeah. It’s been cool to watch. You’ve been involved for so much longer than I have, but let’s just say since 2007, in my case, what has happened with the distribution of these tools and cloud infrastructure, where you have, say a Shopify, where someone could look at Ottawa as a liability. Ends up being this enormous strength in terms of talent retention, because they’re not in an environment like Silicon Valley, where everyone at Facebook is getting poached by people at Google and Apple and fill in the blank.

That type of talent poaching and musical chairs of talent is so prolific. Whereas, if you are the game in town, and you are the promising rocket ship in the form of say a Shopify in Ottawa, your ability to retain talent is infinitely better than a lot of the companies who are dealing with a more cutthroat, dense environment. You might even say the same of, say, Duolingo in Pittsburgh, although Pittsburgh certainly has Carnegie Mellon, and incredible talent recruitment if you’re looking at technical talent. It’s been really cool to see how — 

Brad Feld: I think an important part of that, Tim, is that, and I don’t know the Shopify founders well enough, but my guess is they’re not playing a zero-sum game either. If they’re long-term enlightened, they’re playing a positive-sum game, where what they’re not trying to do is be the only company in town. They’re not trying to be the only game in town.

Tim Ferriss: They’ve seeded — they’re very active investors in Ottawa. They’re definitely a rising tide raises all boats.

Brad Feld: That’s such a powerful moment. Think about that though in the community. In the absence of that, if you have a city where one company is trying to dominate, that won’t be a successful startup community. If you have a city where the dominant, successful startup is enabling and investing and helping make that city better, and really stoking the innovation engine of the city. That’s awesome.

Again, great example, because you totally described the essence of it. Now in 2007, I don’t know anybody that talked that way, and I remember when we started Techstars in Boulder, people were like, “Boulder, why would I ever do a thing in Boulder? Nice mountains.” Today, if you look at Boulder as a startup community, you look at Denver as a startup community, they’re connected, but they’re two distinct things.

The amount of that positive feedback loop, that entrepreneur recycling from companies like Zayo and Rally Software and Datalogics and SendGrid, and now Twilio, after they bought SendGrid and on and on and on. The characteristic of the health of the cities is that much stronger because of the investment of the entrepreneurs back into the innovation cycle of their city. It’s really not that distinct from a 100 or whatever, 150 years ago, as cities were starting to really be developed.

The people in the cities who had generated economic wealth continued to invest in the institutions in their cities, the schools, the museums, symphony, the cultural institutions, a lot of cases that actual business institutions, the sports teams. Mark Cuban owning the Mavericks is an investment that he makes in Dallas. It’s a satisfying investment for him, but he didn’t make an investment in a sports team not in the city he loved. He did it in the city he loves.

Tim Ferriss: Yeah, Michael Dell in Austin, certainly. Also true. Well, Brad, I feel like we could talk for 17 more hours and maybe sometime we should, but I think for a round one, we’ve covered a lot of ground and I’ll certainly link for everyone listening to everything we’ve talked about in the show notes at tim.blog/podcast, you’re going to search Feld, F-E-L-D, and it’ll pop right up. People can find you at Feld Thoughts, feld.com. There’s Foundry Group, FoundryGroup.com. For the social, is Twitter the best social location for you @bfeld?

Brad Feld: Yeah. Twitter is fine. If people tweet at me, I’ll respond to them, totally fine. My email is pretty easily discoverable, so just brad@feld.com. People have things they want to reach out directly about, I’m always happy to get email.

Tim Ferriss: You may get a few emails.

Brad Feld: I’d rather get emails than the random tweet, so I look forward to the Tim Ferriss flood of emails, just put it in the subject line TF, so I know who to be annoyed with.

Tim Ferriss: Oh, great.

Brad Feld: Tim, I’m just going to tell him I’m just going to forward them all to Seth Godin, so we’re good there. Anybody that wants to get an email to Seth Godin, just send it to me or Jerry Colonna, I’ll send some to Jerry randomly. Maybe I’ll toss Fred in for good measure.

Tim Ferriss: Fred, can you handle this for me? Subject line: Forward TF, what the hell is going on? What? I have Tim Ferriss to blame! It’ll really besmirch my good name.

Well, Brad, this has been a lot of fun. I want to ask one last question, which is one of my favorites. It doesn’t always — it’s sometimes a difficult one to answer, but if you could put a message on a billboard, metaphorically speaking, to get something out to billions of people, let’s just say it could be a word, could be a sentence, could be an image, could be a question, anything, a quote, anything noncommercial, what might you put on that billboard?

Brad Feld: I would say, can I have two billboards? One in the Bay Area and everywhere else.

Tim Ferriss: You are allowed to have two billboards.

Brad Feld: I think my billboard for the world would probably be “Breathe.”

Tim Ferriss: I like that.

Brad Feld: Just “Breathe.” Another billboard, which is not probably the Bay Area billboard, but there’s plenty of places would be some version of, “Don’t believe your own bullshit.”

Tim Ferriss: Maybe it’s a sequence, “Breathe” or “Don’t believe your own bullshit,” and then 30 seconds later, “Breathe.”

Brad Feld: Then I come back to “They can’t kill you and they can’t eat you.”

Tim Ferriss: Yeah, that’s a good one. Which one for Silicon Valley? Would it be the “Don’t believe your own bullshit?” All three?

Brad Feld: I’ll let them choose. It would probably have a dot com at the end of it.

Tim Ferriss: Yep, what a world, amazing, beautiful world full of delight and suffering and everything in between. I appreciate you being a companion on the path and sharing your own struggles and your own lessons learned, Brad, so thank you so much for taking the time.

Brad Feld: You’re welcome, and, Tim, I appreciate you a great deal for both all the things you do, but also investing your energy and bringing things like this out for other people, to the extent that anything is useful anywhere. I think you have — you’re a master of your craft and it’s wonderful to watch, and it’s an incredible honor to participate.

Tim Ferriss: Thank you, Brad. Well, I look forward to our future conversations, hopefully more than a few, and to everybody listening, I will have show notes as mentioned to everything we’ve discussed at tim.blog/podcast, just search for Feld, F-E-L-D, and it’ll pop right up with all the goodies, including links to the new books, The Startup Community Way and the second edition of The Startup Communities. Until next time, breathe, experiment well — 

Brad Feld: Indeed.

Tim Ferriss: Be safe, and thanks for tuning in.

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 500 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

Leave a Reply

Comment Rules: Remember what Fonzie was like? Cool. That’s how we’re gonna be — cool. Critical is fine, but if you’re rude, we’ll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration.)