Brad Feld — The Art of Unplugging, Carving Your Own Path, and More! | The Tim Ferriss Show | Transcription

Transcription for the video titled "Brad Feld — The Art of Unplugging, Carving Your Own Path, and More! | The Tim Ferriss Show".


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Intro (00:00)

At this altitude I can run flat out for a half mile before my hands start shaking. Can I answer your personal question? No, I would have seen it a perfect time. What if I did the opposite? I'm a cybernetic organism living tissue over metal endoskeleton. Leave Tim Ferriss show. This episode is brought to you by Theragun. I have two Theraguns and they are worth their weight in gold. I've been using them every single day. Whether you're an elite athlete or just a regular person trying to get through your day, muscle pain and muscle tension are real things. That's why I use the Theragun. I use it at night. I use it after workouts. It is a handheld percussive therapy device that releases your deepest muscle tension. So for instance, at night I might use it on the bottom of my feet. It's helped with my plantar fasciitis. I will have my girlfriend use it up and down the middle of my back and I'll use it on her. It's an easy way for us to actually trade massages in effect. And you can think of it, in fact, as massage reinvented on some level. Helps with performance, helps with recovery, helps with just getting your back to feel better before bed after you've been sitting for way too many hours. I love this thing. And the all new Gen4 Theragun has a proprietary brushless motor that is surprisingly quiet. It's easy to use and about as quiet as an electric toothbrush. It's pretty astonishing. And you really have to feel the Theragun's signature power, amplitude and effectiveness to believe it. It's one of my favorite gadgets in my house at this point. So, I encourage you to check it out. Try Theragun. That's Thera. T-H-E-R-A-G-U-N. Try Theragun risk free for 30 days. There's no substitute for the Gen4 Theragun with an OLED screen. That's O-L-E-D for those wondering. That's Organic Light Emitting Diode screen. Personalized Theragun app and an incredible combination of quiet and power. So go to right now and get your Gen4 Theragun today. Or you can watch the videos on the site which show you all sorts of different ways to use it. A lot of runner friends of mine use them on their IT bands after long runs. There are a million ways to use it. And the Gen4 Theraguns start at just $199. I said I have two. I have the Prime. And I also have the Pro which is like the super Cadillac version. My girlfriend loves the soft attachments on that. So check it out. Go to one more time. This episode is brought to you by Thrive Market. Thrive Market saves me a ton of money and it's perfect for these crazy times. Thrive Market is a membership based site on a mission to make healthy living easy and affordable for everyone. You can regularly save 25-50% off of normal retail prices with member only prices for anything you can imagine really. Whether it's Keto, Paleo, Gluten-Free, Vegan, whatever. You can sort by that. You can find all types of food. You can find supplements. You can find non-toxic home products. Clean wine, dog food. Just about anything. And let me give you a personal example of just how much you can save. So my last order I ordered Primal Kitchen mayonnaise which is made with avocado oil. It's delicious. Justin's almond butter. And the first was 25% off. The Justin's almond butter was 30% off. Rao's homemade marinara sauce which is awesome. 26% off. All said and done at the end of my shopping I saved $39 on my order. So members, and I'm a member, can earn wholesale prices everyday and save an average of $30 on each order. I'll come back to that. And through Thrive Gives, their one-on-one membership matching program, every paid Thrive Market membership is matched with a free one for a low income family in need. And you can try Thrive Market a few different ways. They have the monthly membership which is $9.95 per month. They have the 12 month membership for $5 a month which is billed at $59.95. And right now, this is exclusive to you guys, you can get up to a $20 shopping credit when you join today. Now remember that I saved $39 on my order so basically with one or two orders I pay for the annual membership which is pretty sweet. So go to to give Thrive Market a try. You can, like I said, choose between the membership models you'd like to test out. If it doesn't work for you, you can cancel for any reason within 30 days for a full refund. And on top of that, you will make back your membership and savings as I have or they give you credits to make up for the difference. So it's really win-win-win all around and I would suggest you check it out. Go to You can receive up to $20 in shopping credit. That's for up to $20 in shopping credit plus all of the other great stuff that I mentioned. One more time, check it out, 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. He's written a number of books as part of the 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. Tim, thanks for having me. It's awesome to be here. I can't wait to dig in. You and I have had a number of conversations and I have never failed to take notes and learn and this is no exception.

Brad'S Journey With Depression And Vacations

The first off-the-grid vacation. (06:24)

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. Let's start with something really calm and relaxed and easy.

The tipping point. (06:48)

I'm married to a woman named Amy Bachelor 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." 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. The arc for me as an investor from about 1996 to 2000 was unbelievably intense on the rise up. If you sneezed, you made money. The stupidest ideas were successful. That all continued until one day that was no longer true. In the middle of 2000, I'm traveling all over the country because I invest all over the country. I'm doing my best to 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. Amy and I were literally just seeing ourselves on the weekend. 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 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, it became called Mobius Venture Capital. I'd stay the night. Tuesday, I'd spend all day in the Bay Area. Then I was co-chairman of a public company on the East Coast in New York and purchased. 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 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 a friend's house.

Cycle Begin (09:18)

A longtime friend of mine, a guy named Warren Katz and his wife, Alana Katz, who had been my seventh employee in my first company. Warren and I had been entrepreneurial friends forever from when I lived in Boston and just good personal friends. They had a house in Newport in addition to Boston, and so I met Amy in Boston. Black car must have 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. 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. 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 friend's house probably around three. Our friends are ready for a beautiful summer evening in Newport, and I'm still working. I'm on telephone calls, I'm dealing with my email, I'm doing whatever. Eventually it's six o'clock and we go to dinner. We go to dinner at some restaurant, and by this point I'm trying to be in the moment a little bit without really realizing what's going on. About, I don't know, 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 away out of the table and go outside, and I talk on the phone for a while. I come back and they're having dessert. You kind of know when you're in a relationship and you're fucking up. The signals are not that hard to read. But we went back to our friend's house, and by then we had another little bit more time together and then eventually go to bed. We're crawling into bed, and Amy says very quietly to me, she says, "I'm done." I responded, "Yeah, this was a brutal week. I'm tired. God, everything's so hard right now. These companies, blah, blah, whatever. 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. 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." I had enough wisdom. This is in my – I'm about 35. I 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.

A Tech VC's Obession & The Challenge (12:16)

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. I just want to spend time talking about what we need to do differently, what I need to do differently." After about an hour, things are calmed down, and we're starting to doze a little. I knew better than to sort of 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. 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." 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." Then she sort of snaps into focus, and she says, "You mean I get to control you?" I said, "Yeah. Just give me some rules." All right, so 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? It's 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.

Tactics & Returning to Family (13:56)

She was doing it on purpose. My first company, we kept track of time in five-minute increments. This is software consulting. And every day—and this was 1980, 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, 910 to 925, 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 it day in, 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 weekend. 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 the interaction 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." Oh, 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, you could be, you know, 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 a 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, I'm Mark 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, you know, mutually assured destruction. She'd just keep escalating. I'd escalate, she'd escalate, I'd escalate, she'd escalate. I'd eventually lay on the ground like your dog that says, "Just pep 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." And 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.

What Brad's withdrawal process was like to kickstart his vacations (18:24)

And I'm fortunate that I can take four weeks of vacation like that a year. And, you know, we screw up some. Sometimes we don't end up doing it or 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. You know, 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, you know, 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? I'll 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. I'd love to ask a few follow-ups about the quarterly off-the-grid vacation. Was the, let's just call it, one-year withdrawal process... I mean, was it, 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. 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, 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 nice to just start Monday morning with nothing in your inbox. 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'd come back to this onslaught, and I'd lived 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. It's really... Sneaking into the refrigerator at midnight to have the ice cream. Totally, right? And that's cheating... The best diet ever. Cheating in a way that undermines everything you're trying to do for yourself. So on Wednesday, it's like, "Ah, 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 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, 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. You'd move the week to another week and say, "Look, 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. It wasn't like, "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. 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 in how you think your schedule is? 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 versioned. It's called V, whatever my age is. So I turned 54 last December, so I wrote B-feld V54. And the year before I wrote B-feld 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 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.

Maintaining your normal pace while vacationing with the help of a slow gear down (25:45)

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. That 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 just stay home. Right? So it doesn't have to be that we go somewhere. It's just enough space. It just gives you a more gradual off-ramp, on-ramp and on-ramp, or on-ramp and off-ramp, excuse me.

"They can't kill you and you can't eat you." Brad expands. (26:31)

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? 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 named Len Fassler and Jerry Pock were partners in a company that was called Ameridata, which ultimately was a public company got bought by G 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 spectacular, 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. Len and I started with two other people, Raj Bhargava, an entrepreneur I've worked with a number of times, and Steve Maggs, who also had had a company bought by Len in 1996. That company was a company that bought web hosting companies. We did a consolidation of web hosting companies that really was one of three companies that created a category called application service provider. ASP was a precursor to software as a service or SaaS. There was 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. The company was called InterLiant. And when the internet bubble burst, we had mastered, we built about a $200 million a year business. So pretty sizable company, 1,500 employees. And Len and I were co-chairmen. So we didn't run it. We had an operator, a CEO who ran it, but he was full time. I was part time because I was also a partner at the time, 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 that had another company people may have heard of called Rackspace. And Graham Weston, who's 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've mastered $5 million of loss a month. He'd only mastered a million. So when everything reversed, he was able to get to cashflow breakeven. 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. I was 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 wasn't purchased, so a lot of times I would just stay in purchase because that was where 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'd take a bagel and I'd cut it in half and I'd put it in a toaster and I'd put cream cheese on it, I'd make a cup of coffee, and then eventually he'd 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. I'm sitting at his little kitchen table. He's got his 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 in that big hug somebody gives you from behind. And Len's short. He's like 5'5". It's 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. He could have said, "Fuck it. I don't want to do this anymore. Why are we doing this?" He was in that thing until the end. He felt an obligation to do the work even as it was all falling apart. He didn't even 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 U.S. 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. Thank you for explaining the backstory. There are so many other bullets that I don't want to take you through every turn of the roller coaster. Thanks so far for the first 30 minutes being Brad Feld's version of Misery. Yeah, just putting the cat in a pillowcase and wagging 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. So even at – 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."

Depression in the mid-20s. (34:07)

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's personal experience with obsessive-compulsive disorder (OCD). (35:11)

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. 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. And the anxiety manifests itself in lots of different ways. In my 20s, I had three things happen simultaneously. So 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. And 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 a 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. So you show up, you're at the top of your class in high school, and you've done well and everything, and you think you're really good at stuff. I remember a month in, everybody has to take physics as a freshman. And I get a test a month in, and I knew I didn't do well on the test. And I got my grade, I got a 20. This kid never made 20. I got 20. Maybe I got a B in some English thing somewhere. I thought I was really good at physics. I got a 20. What do you do when you're 17 years old at college away from home, and you get 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 A.V. on that test was 32. So I actually got a B minus C. Who the fuck gives the first test so that the class A.V. is a 32? MIT. That's what they do. They make you very aware that you are—there's 10% of the people there are off the charts, but they make the other 90% very aware. Yeah, you're smart kids, but you're going to have to work hard. So college, I was successful. I'd started a company. It was successful. I married my high school sweetheart, not Amy. I was in a Ph.D. program at MIT at a very young age while running my company. Externally, everything looked awesome. And 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 Ph.D. program because I was a lousy Ph.D. student. I was running my company and I wasn't taking it seriously. And three is I was incredibly bored of my business. So my business, while it was succeeding, was not stimulating me in any way, shape, or form. And 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 Ph.D. advisor, who to this day is still a wonderful substitute paternalistic figure for me, a guy named Derek von Hippel, connected me with his therapist, who was a classical Boston psychiatrist. It 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. So the treatment that I had, which was both CBT and medication, was highly effective. Cognitive behavioral therapy, a certain type of therapy, where you think about therapy with sitting on a couch, laying on a couch with your back to the therapist is one type of therapy. This was the 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'd taken a red-eye to New York the night before the towers fell, so 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. And 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.

Recurring depression episodes. (40:31)

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? I know. 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.

High-stress circumstances leading up to a recent depression episode. (40:51)

And in 2013, I had another one. And this time, it was a result of a bunch of things that happened in 2012. And they started with me running a 50-mile race in April of 2012. So I overtrained. I trained a lot. I was working a lot. My business world was going very well between Foundry Group and Techstars. I had a very healthy relationship with Amy. I had lots of things, but I was working really hard. And 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. And a bunch of things happened, including a near-fatal bike accident at the end of the summer. We had one of our dogs die. It sounds like a country music song sometimes. I ended up with a kidney stone that I had been ignoring and just avoiding. Oh, 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. And sort of in the end of this, at the end of 2012, I was physiologically exhausted, just completely kaput. And I had this kidney stone surgery, which I had a very big kidney stone, so they had to actually do surgery to get it out. I kind of took most of December off to recover. I thought I was fine. I'm like, "Okay, let's get back to it." And I went to CES in Las Vegas, Computer Electronics Show, which is the second week of January. And 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. And there was a little bit of conversation around that, but not a lot. Aaron Schwartz was probably the first of the stream. And there was a pop of, "Oh my gosh, this person, how could this have happened?" And then it would drift away.

Introspective Conversations With Brad And Jerry

Brad's struggle and the value of having a few people in your corner (42:51)

And 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, various motivations, a lot of it to be that I think by writing versus thinking some other way. Brad Kaye, pause for one second. 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 the half-life of shame just decayed over time? Because that's a really... That is not an incremental change. No, it's a good thing to interrupt with. So in my 30s, I was still pretty ashamed of being depressed, but I realized I was depressed out in the open. By the time it got into my 40s, and when we started Foundry Group, we made a commitment to each other at the beginning that we would be available to each other, emotionally available to each other as partners. And our effectiveness of that, how well we've done at that, has ebbed and flowed over time. I wouldn't say that we are perfect at that and it'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. 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. And 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, and we had lots of conversations about it. And 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 Jolk, 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. And then one person in particular really changed how I approached it, which was Jerry Colonna. And I know you know Jerry and he did a great podcast with you not too long ago. Yeah, the coach with the spider tattoo. Indeed. So 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. And it wasn't really till the late 90s, almost early 2000s, when Jerry was kind of departing that Fred and I started to really engage with each other at a deeper personal level. And 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. And when Jerry finally disappeared for a while, I could handle you." And 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 sort of going through things, maybe 2010, 2011. And we're having these conversations about how full of shit most of us are all the time. And he's coaching now and 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. And in this conversation that we're having, we talked very quickly about depression and he's been depressed and 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. And 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. And 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 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. So I carried that with me. And when I had this depression in 2013, I immediately went back into therapy. I hadn't been to therapy since I was in my 20s. I immediately went back into therapy. And I remember the day that I had that therapy session, which was the first therapy session with a new therapist is kind of worse than the first day of school at a new school. It just kind of sucks. But I wrote a blog the next day and 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 were 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? I remember when Fred and I started blogging in the 2004 timeframe, lots of people said, lots of VCs, lots of our peers said, they must have way too much time on their hand to write blogs. Right now everybody writes blogs. But it's kind of the same thing. It's like, no, 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. And I'm going to let go of this shame in an active way. And if that's helpful to the people I work with and the people that I support, that's a good thing. And 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 into 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. And that didn't make me feel necessarily better, but it made me feel that what I was doing had value.

What annihilated Brad's shame (50:03)

And that created a positive feedback loop, which over time essentially obliterated the shame. It didn't just make it go away, it obliterated it. It's like, nah, we're human, this is part of the human condition, we can either deal with it or not deal with it, and I'm fine dealing with it. And 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 cruft 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. And I think that was sort of it all clicking into place for me, which is, all right, I'm going to die someday. 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 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.

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What Brad admires most about Jerry (53:15)

By that do you mean the questions that he asks or does that have a different meaning? A little of that. Some of it's the questions. I mean Jerry has a well known superpower which is that people start crying in front of him in a group right away. And people that would never imagine that they'd start crying and let their emotion out, let their emotion out. And 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. You know, 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. And he opens that door quickly. Doesn't take four years of therapy to open that door. He opens that door in the first 15 minutes and all of a sudden the door's open. You don't have to dance around it for four more years. And when the door opens, I mean 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." And so when that door opens, all the barriers just sort of crumble all at once. And 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 had 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. And then he stays with it. And he stays with it not in a hostile way, not an aggressive way, not in an attacking way, just in this Jerry way. I don't have a label for it. That at least from my experiences with him, take people to a place where they realize, wow, okay, what is important to me?

The hard question worth answering (55:58)

Very, very quickly. Yeah, he's very good at honing in, and he skips a lot of the foreplay, which is, 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? And 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 are really, I've found, really, really fruitful. 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 completely, I mean, you do too, right? You have the freedom to do what you want to do, where freedom is a very American word, in some ways, a 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. 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, right? 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? And 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? And is that thing it's satisfying a good thing or a bad thing? And is it a wanted thing or an unwanted thing? And, man, even with things that seem so obvious from the outside to my best friends, I don't see them. And I think that's true for many people, right? We're in complete denial of how we're creating those conditions that create our unhappiness.

Why Jerry can often get away with poking through discomfort where others get a blank stare or backlash. (58:36)

To create our happiness, that's good, but create our unhappiness, create our limitations, put whatever box around and put a negative sign in front of it. And 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." There's something also very special about—I haven't interacted with Jerry in a group environment, but in small group environments, particularly—and 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 sort of 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. So I do think there is something to that. It's a good insight. I mean, it's probably one of the reasons why group therapy is a thing. He and 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. And we 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. And it's two stories, and the upstairs is perfect retreat space, and the downstairs is like a place you could have nonprofit fundraisers or dinners or whatever. And he and the Reboot team would take over the space for four days, and my only request of the people that came is that they don't come to the house. They don't bother—you know, 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. And 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. And 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. And imagine a bunch of VCs showing up to a four-day thing like this, and they've got their armor on. Or CEOs, either one. And 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. And then somebody just takes their armor off and goes for it. And 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. And I've seen this happen every single time, and it usually happens within the first couple of hours. And it's remarkable. And I think of you as having a very kind of 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 kind of 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 and when you went back to choose a therapist or for someone asking you how they should choose or find a therapist?

Therapy And Relationship Communications

How Brad found his two magic number therapists. (01:02:36)

You reminded me that I never answered why three is my magic number. We'll come back to that. So I've chosen two therapists. I chose a therapist in my 20s, and I chose a therapist in my late 40s. And 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. And they did it with no strings attached. So in the first case, in my 20s, it was Eric von Hippel's therapist, my PhD advisor's therapist. And 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. And I had had one prior bad therapy experience, which was before my first wife and I split up. She was going to a therapist, or she'd 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. And we had one session and I don't know, word malpractice is loaded, right? I felt attacked for the entire 50 minutes by her therapist. And that was it. We didn't go back and 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 is his name was Dr. Mogul. And I thought for an entrepreneur, that was the perfect name for a therapist. But I was in shape where I didn't – 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, and so that worked. The second time, my therapist was recommended to me by Jerry. And it was a friend of Jerry's, not a therapist of Jerry's. And 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 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 sort of navigate through this next phase with. And I said, "And 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 earthy-crunchy, hippie, Buddha-y, whatever." I said, "I want that in my life at this stage." And he said, "I've got the perfect person for you." And it was a classically trained psychologist. His name was McAndrew. His last name is his first name, and his first name is his last name, which got me a hello. There's a school in Boulder called Naropa that was one of the very first alternative schools in the country. It may have been the first one that was Buddhist. And very famous from the 1970s, a key part of Boulder. And McAndrew teaches at Boulder, so he was a Naropa professor. Jerry Maystilby 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, 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. 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 McAndrew's just 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.

The utility of referrals in therapy (01:07:18)

So one of the things that I find is a really useful thing is, and then comes from my experience here, if you are 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 that for, 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 a 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. And that's the key. It's not that. It's 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 like, 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.

Coaching versus therapy (01:09:07)

What is the role of therapist versus coach for you? Is the therapist the salve and the coach the whip? No, it's like looking for monopoly pieces, right? 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. The salve and the whip is kind of okay. I mean the coach is the whip, right? The coach is the one saying come on. But a really good coach is also, you know, there's part therapy. I mean Jerry talks about, you know, to be a great, and the reboot way is a combination. Their methodology as 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, right? 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. Or you might get really great at doing the wrong thing. 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. Right? Well, 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.

Why does Brad frequently refer to himself as "Number 3?" (01:12:29)

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 is 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? So here's how OCD works. We all have obsessions and compulsions. It's 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, they're 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 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, right? 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 signs 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. 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 when my engineer brain kicks in, I had to do it nine times. Right? I love the combination of OCD-inflicted superstition and engineering. And engineering and numerology. All right, so what happens if I screw it up when I don't do it nine times? Got to do it 27 times, three times, three times, three. If you have ever had to do something stupid, that is, you know, stupid is the wrong word. If you ever have to do something, you're trapped, right? 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, you know, interestingly, I care a lot about symmetry. So in some ways, four would have been a better number than three. And 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.

What is a life dinner? (01:16:54)

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? 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 him and her, "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 p.m. Colorado time to 10 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. At the time of COVID, we for sure do it 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 bit. I really hope it was the same dinner that you gave her the – no, no, no, you didn't give her the fart machine. That would have been less popular. 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 and anything. Just retrospective. This is 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 ten more days and it could be 11 more days and 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 ten minutes and sometimes it might go three hours. And sometimes there was laughter and sometimes there were tears and sometimes there were both.

Communication tips for someone in a relationship with a partner who has a temper (01:21:26)

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. Nate, you mentioned earlier that Amy has a temper. 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? 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. Any couple that says they never fight is totally full of shit, right? Because we're humans. And we learned, 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 violence ever in any scenario. Red line is the word, right? It's just an uncrossable line, no physical violence. Now by that you mean physical striking or you mean pounding the table, anything like that? Yeah, I think a 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. It's pounding the table, but there's a big difference between pounding your fist on the table out of frustration and doing it in a way that potentially, you know, jerking someone's chair. Right? I think pounding a fist on a table probably would be okay in our, I don't know how to, that's gamey. But certainly, you know, 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 can't, 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, right? 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. What do you do instead, if I may ask, instead of shutting down, do you have an alternative, right? So for people who might be inclined to withdraw into themselves and just kind of blank out like Wally shutting down, if they feel like they're being pummeled, how do you counter, what's the counter move? One is I try to stay in the moment with the anger. And again, I think this is a function of trust, right? 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%. So I know that she is angry at me, and I know that the anger will run its course. 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 try 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, right? That kind of stuff, which is a 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 the whole situation. They don't really know what's going on. And the third then, so staying deeply engaged, then leads to the third.

The tactics Brad uses with Amy during conflict to help diffuse tension (01:25:59)

The other tactic, by the way, I try to use humor in those moments. We have lots of stories of us ending as where she gets out of an angry face. 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 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 hers to apologize to me and me to apologize to her, but we both apologize. And it's a real apology. It's not a "I'm sorry you got angry at me" kind of apology, which is not an apologize. That's always a winner. Right? It's total bullshit. I'm so sorry you're responding so poorly. Right. It's just simple. It's "I'm sorry," and "I'm sorry," and "hug," and you go on. Right? 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.

Communication tools Brad and Amy used early on in their relationship and since (01:27:53)

Do you guys take any—and maybe in the early days, it should 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. So, notes, taking notes, helpful, hurtful, otherwise? Do you have any thoughts on taking notes? If there's any sort of looking forward, planning, etc., is it helpful to have notes, or do you guys prefer to do it all verbally? Yeah, for us it doesn't. I think it can be very helpful. I think it's very individualistic. I am not a note-taker. I just not. I have a good memory, but I also have a memory that's a synthesizing memory versus a factual detail memory. And so taking notes actually clogs up my ability to synthesize things. And so I'm also a very good reader, and I learn by reading. So I've sort of learned about myself that 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. For Amy, she is an extremely good, she's an 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 have 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, right? 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. 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. And 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.

The practice of retrospectives and the Peltz occasion (01:31:12)

I think the practice also, by the way, of the retrospective, right? Okay, you had to 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 in 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, by the way, the other end of the spectrum, feel really good. There's all sorts of stuff that I want to cover, and I think we're going to probably run out of time.

Digital sabbath (01:32:10)

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? 80% of the time, four out of five, three out of four, four out of five. I didn't used to do it. 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'd work another half day to full day on Sundays. 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. 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 a week." By the way, when I was depressed, I was having trouble getting out of bed, so that was a hard thing to agree to. I was like, "Yeah, that sounds great." 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 Jewish friends who take the Sabbath off completely Friday night to Saturday night." I just said, "I'm going to apply the week off the grid to Friday night, and I do it to Sunday morning," because I found that if I got back on the grid Saturday night, that was kind of silly. For my frame of reference, it kind of defeats the purpose. We kind of use sundown as the trigger, although it's not a hard boundary. In Colorado in the summer, the sun doesn't go down until 830 right now. We have a place in Alaska. Sometimes when we're in Alaska, the sun doesn't go down until 2 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. I'll pick this back up on Sunday." 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, just trying to rally a bunch of people in the private sector to help the state. Specifically, we have a fantastic governor in Colorado, Jared Polis, who's a very successful entrepreneur and a good friend. Sort of in that period, I think I skipped three weeks. 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. 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. For some period of time—actually, for a long period of time, I was doing screen-free Saturdays to the best of my ability. 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. You really do notice the gear shift, or I should say the gears grinding when that gets removed for any extended period of time. 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. 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. I had gone for a run, and I had taken a nap. I was kind of bored, which almost never happens to me because I fill up my world with stuff all the time. I don't allow myself the luxury of being bored because I always have too much to do, which is a whole other version of—it's basically boredom aversion. 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. I said to Amy, "I kind of feel a little bored." She laughed, and she said, "Isn't it wonderful?" 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." For many people in today's world, it's hard to do. 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."

My favorite five books by Brad Feld and where to begin with them (01:37:45)

You mentioned reading. All roads lead to Colorado, and this question I keep promising. 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 Piers Egg, Battlestar Galactica by Ronald D. Moore, Snow Crash by Neil Stevenson, Neuromancer by 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 non-fiction purist for a long period of time, is there one that jumps to mind as the starting point? Let me resegment that a bit because they're not all books. Battlestar Galactica is an online community that I just started a couple, maybe ten 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 it in 2012 when the phrase "startup communities" didn't exist. 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. Nobody had ever created it, so I just decided to create one using a tool called Mighty Networks that's really quite interesting and well done. In a very short order of opening it up to people, 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, Peirceg's book, Zenden 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. I 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. While it's fiction, it's sort of fiction, memoir-y philosophy. It's fiction like memoir is fiction, right? Fiction's the wrong word for it. It's memoir-y philosophy. 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, the narrator, who is the author, over a period of time where he descends into madness against the backdrop of classical philosophy. 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. I think that's a book every human being should read.

Brad's three book recommendations (01:41:03)

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

Various Literary And Cultural References

Will Your Toaster and Thermostat Befriend Or Betray You First? (01:41:26)

Neuromancer was first. It was written in 1984. If you read it today, you kind of go, "Eh, whatever." But if you read it, if you time travel back to 1984 and read it, given our world in 1984, it will blow your mind how he predicted.

Glassec (01:41:44)

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.

Hyperion (01:42:10)

Snow Crash is written in 1992, so just before the World Wide Web begins. 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 were not going to be able to travel, you were 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, Hyperion, Kantos, 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.

Battlestar Galactica (01:44:15)

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 like 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 put them so much at the top of the list for 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 them, but they cause you to think about your own world in a totally different way. 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 ten, that's really emerged now, I think, as a really great writer. I mean, becoming a great writer of any sort is a craft. You've got to do a bunch of it, as you know. And you write a bunch of shit, you write a bunch of shit, and 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. And the next thing you do is a guy named Elliott Pepper. And Elliott has become in a category called near-term science fiction writers that guys like William Hurtling and Daniel Suarez are in, which are things that you can 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. 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 worldbuilding, I just want to throw another book in, if people aren't overwhelmed already, which is Dune. Frank Herbert, in terms of worldbuilding. It's a mind-blower. Well, it's classic. It's the beginning of that genre. Yeah. I feel like you can learn almost all the leadership lessons you need from Dune. It is just truly spectacular work. 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, you know, everything goes away and we're back to normal, 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, you know, the current pandemic in 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 dystopic ending, really, really dystopic ending. But, you know, the first 25% of the book is about where we are right now.

Ted Chiang (01:49:14)

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. 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 two collections. The book 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 structures 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 Automatic, M-A-T-T-I-C. You might see Matt Mullenweg, Automattic, in any case.

Ken Liu (01:50:07)

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 play in the shallow end with deep meaning, without getting over-committed. 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 to 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? There'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'm more of a loner than a joiner. I am more of a detached or disconnected from a sort of in-the-middle-of kind of person. 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. When you're in your college and you're in your early 20s, the definition of home is tricky. 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." 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.

Transition From Boston To Boulder

"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" (01:52:22)

I think our friends just thought we were wrong. Like, "Yeah, whatever. We hear you, but whatever. You're not seeming to take action against that." 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.

Brad's decision to move to Colorado (01:52:35)

We traveled a lot together, and we liked to explore different places. She said her requirements were ocean or mountains. Growing up in Dallas, I didn't have either. I didn't totally get that, but I'm like, "Okay, well, not both either." She's like, "Either. I need one or the other." Growing up in Alaska, she had both. 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." That's a strong hand. We married, right? I had sold my company. I was still working. I was doing lots of angel investments around the country. 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. I had come here skiing as a kid some, and then as a young adult some. Colorado was just the fantasy of it. It was a cool place. The 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. 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. So not the epicenter. That kind of appealed. We went to Colorado for a two- or three-week trip. We'd been in Boulder on a December/January day that was 50 degrees on the Pearl Street Mall. It was a beautiful winter day that was not really wintry. I was 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. We flew out. We rented a house. We flew back. We told all our friends we were moving to 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 in 1995. Our view, our goal was nothing, zero to do with work. Our goal was to build a life here. Let's evaluate whether this is the place we want to build a life, and if it isn't, try something else. If it is, this is our place. 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 El Dorado Canyon, behind the El Dorado 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 100 acres there. We lived there for 17 years. 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. Now we're looking at the mountains rather than being in the mountains. We have this real sense of expansiveness as we look at Long's Peak each morning. 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.

What Brad has learned to like about Boulder over the years (01:55:59)

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. 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 Rosen's house in Atherton. I mean, it's a beautiful place. It's not my place. It's not where I feel at home. 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. 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. One of the things that's been most powerful to me about Boulder, at least from the time period 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. 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. Different dynamic. And I was aware of that. I was aware of the overwhelm that I felt when I was in Los Angeles. Just, you know, Los Angeles isn't a city. Somebody told me once the number of its 80-something cities in one thing called Los Angeles. 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.

Welcome to Homer, AK (01:59:23)

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 8. And we used to go to Homer for a month every year. We still go to Homer 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 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 love 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 until after we had a place there and were living there on a part-time basis, that it was an enclave as well. 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.

Living outside of big tech (02:01:22)

And then most interestingly, how our technology today has changed all that. Pre-COVID, if you had said to somebody, "90% of people who work in office buildings or 95% of people who work in office buildings are going to be working from their houses for the next three months," the person would have 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. It 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 is 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.

Topophilia: Love of a place (02:02:57)

He was one of the people that basically helped create the microbrewery industry and the idea of a microbrewery in the first place. I remember the first time I heard this word from him. 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 almost said 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 enclave-y 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. Let's talk about, I think I would be remiss, or it would be remiss, I'm missing my grammar, but if I were to ask you about something that's come to mind for me because you and I have kind of chatted briefly about it, and that is complexity theory. And I'd like you to even just define that. But in the startup community way, well, 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 your problems. You've written a bunch of books, and I believe I own and have enjoyed all of your books. Thank you. 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. I think that's every book I've tried. Right? It's not just partial shit. It's total shit. And that was the experience that my co-author Ian Hathaway and I had about a year into working on the startup community way.

Entrepreneurship And Parenting Perspectives

Raising a Kid as a Complex System (02:05:38)

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 long discussions. And he said to me, "Have you ever thought about writing a sequel?" And I said, "I hadn't really thought about it." He said, "You know, I think the world of startup communities and all the people I'm talking to, 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. So we decided to write a book that was a sequel. So we started writing the sequel. And we wrote, I don't know, a book like The Startup Community Weighs, 50,000, 60,000 words, probably wrote 25,000 words. And we were both unhappy. And it was hard. And there was no rhythm. There was no cadence to anything we were doing. And Ian called me. He'd moved to Boulder for a while and then moved to London. And he called me, or sent me a note, and he said, "I have come up with a framework to use to describe what The Startup Community Weigh is." I said, "Okay." He said, "What a startup community really is, is a complex adaptive system." That's all I said. I said, "Silence." And I said, "100% agree." So 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 Weigh and for how people think about it, I think the idea of complex systems is 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 Madeline Obrad'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 really liked and respected. Seth was one of them. He talks in the podcast, you all talk about how he makes a cup of coffee and his obsession with a cup of coffee and 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. Yeah, 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. You 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 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 are 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 cardiologist, dot dot dot dot dot, 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. But 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 aha, 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... M. Mitchell Waldrop, does that sound right? M. Mitchell Waldrop. Yeah, complexity, subtitle, The Emerging Science at the Edge of Order and Chaos. So that book I read, I remember laying on my couch in my apartment on Bay State Road reading that book and just sort of, it must have been 1990 or 1991, and just having my mind blown. It was just like, yup, yup, yup, and Conway's Game of Life and sort of all the stuff from that around emergent behavior, contagion, positive and negative feedback loops, words that we throw around, and 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 regret 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, but 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. What does that mean, and especially what does that mean over a long period of time, because again, if the inputs are becoming the outputs, etc.

Successful Founders and Entrepreneurial Recycling (02:12:05)

I mean, the thing that today to this moment is kind of 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. And 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, and 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. And 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 the things we're doing affect everything else we're doing. And back to this notion of, I love contagion in this context, right? 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. And if you scale it up to society, that's what we're talking about in the startup community way. I mean, 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. I can't wait to check it out. I've watched these communities, vibrant communities pop up in some of the last locations I would expect. Like, for instance, Ottawa, Canada, when Shopify, which 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 graduates/alumni and the factors that made it such that it could develop this vibrant ecosystem are really fascinating. And I mean, 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. But what 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.

The most important characteristic of entrepreneurial recycling. (02:15:09)

Thanks. That last statement is exactly correct and super important. Your Ottawa example and your Shopify example is an example of what we refer to as entrepreneurial recycling. And the idea is that over time, it takes a long time, right? 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. And if they care, if they have topophilia, if they care about their city, it's not just the entrepreneurs, it's also many of the early employees. And 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 and 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. And if you go back to the initial conditions of Silicon Valley, that happened a lot over a long period of time. And 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. And 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 is powerful. I can't not say this because it's a fundamental part of what I call the bolder thesis around startup communities is that you have to take a very long-term view. I used to say you have to take a 20-year view from today. Now I say you have to take 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. And 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. Yeah. It's been cool to watch. I mean, 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. And 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, a Duolingo in Pittsburgh, although Pittsburgh certainly has Carnegie Mellon and incredible talent recruitment if you're looking at technical talent. So it's been really cool to see how… I think an important part of it, Tim, is that 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. They're very active investors in Ottawa. They're definitely a rising tide raises all boats. And 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. And so, 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 go do a thing in Boulder?" Nice mountains. And 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 entrepreneurial recycling from companies like Zayo and Rally Software and DataLogix 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. And it's really not that distinct from 100 or whatever 150 years ago as cities were starting to really be developed. And 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 the actual business institutions, the sports teams. Mark Cuban owning the Mavericks is an investment that he makes in Dallas. I mean, 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.

The importance of a long-term view for startup communities. (02:21:41)

Yeah, Michael Dell in Austin. Bingo. It's also true. Brad, I feel like we could talk for 17 more hours and maybe sometime we should, but I think for 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 You can just search "Feld," F-E-L-D, and it'll pop right up. People can find you at FeldThoughts, There's Foundry Group, For the social, is Twitter the best social location for you at B. Feld? Yeah, Twitter's fine. If people tweet at me, I'll respond to them totally fine. My email's pretty easily discoverable, so just If people have things they want to reach out directly about, I'm always happy to get an email. You may get a few emails. I'd actually rather get emails in the random tweets, so I look forward to the Tim Ferriss flood of emails. Just bring the subject line "TF" so I know who to be annoyed with. Tim, 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 Colon. I'll send some to Jerry randomly. Maybe I'll toss Fred in for good measure. Fred, can you handle this for me? Subject line forward, "TF." What the hell is going on? Tim Ferriss to blame? That'll really be smurch my good name.

Brads billboard. (02:23:04)

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, sometimes it's 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 non-commercial, what might you put on that billboard? I would say, can I have two billboards? One in the Bay Area and one everywhere else? You are allowed to have two billboards. I think my billboard for the world would probably be "breathe." I like that. 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." Maybe it's a sequence, "breathe," or "don't believe your own bullshit," and then 30 seconds later, "breathe." And then I come back to "they can't kill you and they can't eat you." Oh, yeah, that's a good one. Which one for Silicon Valley? Would it be the "don't believe your own bullshit"? I'll let them choose. It would probably have a dot com at the end of it, so... Yeah, it's... what a world. Amazing, beautiful world full of delight and suffering and everything in between. And I appreciate you being a companion on the path and sharing your own struggles and your own lessons learned, Brad.

Parting thoughts (02:24:47)

So thank you so much for taking the time. 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're a master of your craft, and it's wonderful to watch, and it's an incredible honor to participate. Thank you, Brad. Well, I look forward to our future conversations, hopefully more than a few. And to everybody listening, I'll have show notes. As mentioned, to everything we've discussed at, just search for Feld, F-E-L-D, and it'll pop right up with all the goodies, including links to the new books, Startup Community Way, and the second edition of Startup Communities. And until next time, breathe, experiment well, be safe, and thanks for tuning in.

Additional Resources And Supporting Services

Additional resources: StartUp Community Way and more (02:25:42)

Hey guys, this is Tim again. Just a few more things before you take off. Number one, this is Five Bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend? And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered, it could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short. It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out. Just go to That's all spelled out. And just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it. This episode is brought to you by Thrive Market.

This episode is brought to you by Thrive Market (02:26:45)

Thrive Market saves me a ton of money and it's perfect for these crazy times. Thrive Market is a membership based site on a mission to make healthy living easy and affordable for everyone. You can regularly save 25 to 50% off of normal retail prices with member only prices for anything you can imagine, really. Whether it's Keto, Paleo, Gluten Free, Vegan, whatever, you can sort by that. You can find all types of food. You can find supplements. You can find non-toxic home products, clean wine, dog food, just about anything. And let me give you a personal example of just how much you can save. So my last order, I ordered Primal Kitchen mayonnaise, which is made with avocado oil. It's delicious. Justin's Almond Butter. And the first was 25% off. Justin's Almond Butter was 30% off. Rao's Homemade Marinara Sauce, which is awesome, 26% off. All said and done, at the end of my shopping, I saved $39 on my order. So members, and I'm a member, can earn wholesale prices every day and save an average of $30 on each order. I'll come back to that. And through Thrive Gives, their one-on-one membership matching program, every paid Thrive Market membership is matched with a free one for a low-income family in need. And you can try Thrive Market a few different ways. They have the monthly membership, which is $9.95 per month. They have the 12-month membership for $5 a month, which is billed at $59.95. And right now, this is exclusive to you guys. You can get up to a $20 shopping credit when you join today. Now remember that I saved $39 on my order. So basically, with one or two orders, I pay for the annual membership, which is pretty sweet. So go to to give Thrive Market a try. You can, like I said, choose between the membership models you'd like to test out. If it doesn't work for you, you can cancel for any reason within 30 days for a full refund. And on top of that, you will make back your membership and savings, as I have, or they give you credits to make up for the difference. So it's really win-win-win all around. And I would suggest you check it out. Go to You can receive up to $20 in shopping credit. That's for up to $20 in shopping credit, plus all of the other great stuff that I mentioned. One more time, check it out.

Sponsorship And Advertisement

This episode is brought to you by Theragun (02:29:14)

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