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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 at Bealefeld, AFLD. 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 nineteen eighty seven. I've been reading his writing forever, it seems.

Prior to cofounding 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. Felde Thoughts and Venture Deals. Two of my favorite blogs out there, which really are, I think, timeless and a lot of the lessons that are taught. Brad holds a Bachelor of Science and Master of Science Degrees and Management Science from the Massachusetts Institute of Technology MIT.

Brad is also an art collector and long distance runner. He has completed twenty five 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. 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.

Now, let's let's start with something really calm and relaxed and easy. So I'm married to a woman named Amy Batchelor, and we've been together now for almost 30 years. The first off grid vacation I took was the result of a moment in time where Amy said to me, I'm done, and I thought she meant that she was done with the week because it had been a really shitty week for me. But she was actually saying very quietly, you know, 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 two thousand one, but it's definitely deflating fast and in sort of the arc for me as an investor from about nineteen ninety six to two thousand was unbelievably intense on the rise up. Like, you know, if you sneezed, you made money. The stupidest ideas were successful and then that all continued until one day that was no longer true.

And so middle of 2000, I'm traveling all over the country because I invest all over the country.

I'm doing my best to sort of keep everything together. I'm trying to save what is a portfolio that I have that's falling apart very, very quickly. Several companies that I co-founded, along with a lot of companies that I was on the board of or an investor in, and Amy and I were literally just seeing ourselves on the weekends. So my week would start on Monday morning. I'd get up early, usually four o'clock Colorado time. I'd go to Dédé, take six a.m. United flight to the Bay Area.

I'd spend Monday all day and a partner meeting at the firm I was at then, which was during that period of time called Softbank Venture Capital, or Softbank Technology Ventures, ultimately became called Mobius Venture Capital. And I'd stay the night Tuesday. I'd spend all day in the Bay Area. And then I was co-chairman of a public company on the East Coast in New York and Purchase. So I take a read usually on Tuesday night or Wednesday night, spend a couple of days in New York, maybe on Friday, go somewhere else and eventually come back home, crash for the weekend, just out of exhaustion, catch up on whatever I could catch up on.

And then sort of Amy would patch me up and send me back out Monday morning and I'd do it again week after week for a lot of weeks. This particular Friday that this started, she and I had planned a vacation to a friend's house, a longtime friend of mine, a guy named Warren Katz, and his wife, Ilana Katz, who had been my seventh employee in my first company, and Warren and I had been making been entrepreneurial friends forever from when I lived in Boston and just good personal friends.

And they had a house in Newport in addition to Boston. And so I met Amy in Boston. 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. And I'm on the phone like 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, a meaningful way on the outcomes of these companies.

And I probably in between calls, I look 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. Right. I'm on telephone calls. I'm dealing with my email. I'm doing whatever. And eventually, it's six o'clock and we go to dinner and we go to dinner at some restaurant, and I you know, by this point I'm sort of trying to be in the moment a little bit without really realizing what's going on and about how 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 and I come back and they're having dessert. And, you know, you kind of know when you're in a relationship and you're fucking off, signals are not that hard to read. But, you know, we went back to our friend's house and by then we sort of had another, you know, whatever, a little more time together and then eventually go to bed and we're crawling into bed.

And Amy says very quietly to me, she says, I'm done. And I responded, Yeah, this was a brutal week, I'm tired, I got everything so hard right now, all these companies, blah, blah, whatever.

So this week is over. I'm looking forward to having a weekend with you. She says, no, that's not what I meant. She she says you're not even a good roommate anymore. She's I love you. I think you're awesome. But I don't want to live this way and I don't want to watch you do this to yourself. And I had enough wisdom this is in my about thirty five have enough wisdom to know not to go to bed or not to roll over when you're when your wife says that to you.

So we talked for about an hour. And I kind of I'd like to say I talked to her off the ledge of being done. I said to her, you know what? This weekend, no phone, no computer.

I'm done. I gave her my phone. I gave her my computer. I said, put them in your bag. Between now and when we leave here Monday morning, I'm not going to do any work. I'm not going to think about work. And I just want to spend time talking about what we need to do differently, what I need to do differently. And, you know, after about an hour, like, all right, things are calm down.

And, you know, we're we're kind of starting to those a little you know, I I knew better than to sort of nudger and say, you know, so any action happening tonight because, you know, like, all that was going to generate was was more laughter.

So we we go to bed, we wake up the next morning and we go for a walk. And I said, look, I know that you're not happy with the dynamics here, but I don't want to split up. I love you. You're the person I was put on this planet for. I think I was the person you were put on this planet for. I've got an engineer's brain. I just give me some rules and she looks at me.

And her first response is, I don't want to give you rules like that puts it on me and that's not romantic. And then she sort of snaps into focus and she says, You mean I get to control you? And I I said, yeah, yeah, just give me some rules and all right, so walk a little bit more to describe the first thing I want you to do is I want you to keep track each day of how many hours you work, and I want you to report them to me.

Now, she knew that this was pressing a gigantic red button in the middle of my forehead and it's what our significant others do, right. And what we do to them, like, you know, the biggest point of pain or the biggest trigger of your significant other, if you have one and they know of yours. And she was doing it and she was doing it on purpose. My first company, we kept track of time in five minute increments, the software consulting with us and every day.

And we 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 like a paper grid that I filled out nine, ten, nine, twenty five. And then a code for, you know, which client I worked on and then a one sentence description of what I did, just like lawyers do. But we did 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 timing.

And and so my first reaction was, no, I'm not going to do that. And she looked at me just you said I could make the rules. So we ended up having an amazing set of conversations that weekend. 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 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, we make 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 like 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 or 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 Namir. Other thing that two adults do. And my phone would ring and I'd answer it no matter what was going on between us, no matter what sort of interaction 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. Oh, sorry. I've got to answer this phone call. And you could do it with phone calls, you could do with emails, you could do with work, you could be I was late to every single thing we ever did because I just had one more thing to do before I went to the dinner that we had scheduled for the fancy night out or whatever.

So when she said to me, your words don't match your actions and then gave me an example that really snapped into place and that's been foundational. The other part of it was and this is a thing I've learned about Amy, I don't have much of a temper. I suppressed my anger and frustration. I'm like Marge Simpson and I just push it down to my toes. And I have lots of other ways to process it, some that are not particularly healthy, which I expect approached me on at some point, but I don't have much of a temper.

It takes a lot to get me to react with anger, external anger. Amy has a temper and I learned early on in our relationship that there was no value in trying to win. When her temper started to escalate, it was mutually assured destruction. She'd just keep escalating and escalate. She'd escalate, escalate, escalate. I might eventually, like, lay on the ground like like your dog that says, you know, just put 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 I'm she say I'm enabling that. But that would be the language we use today. And so from that came this idea of basically a quarterly vacation off the grid.

So each quarter since 2000, we take a week, Saturday to Saturday, and we just go off the grid. And I'm fortunate that I can take four weeks of vacation like that a year. And no, 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 for a week, a 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 you with the person I love the most was so hard to do, but it was so worth it. Three or four years later, the muscle that was built was four times a year. I kind of just say to the rest of the world, fuck it and disappear for a week. And as far as I can tell, 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 be I won't close this investment or I'll miss this new opportunity or whatever. Right. Pick your business anxiety. Well, yeah, all those things happened, but none of them were significant. 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 if you follow ups about the quarterly off the grid vacation was the let's just call it one year withdrawal process. I mean, was it was it I use that term deliberately or 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. It's more than a year to detox or to, you know, to to get into a place where it was like flipping a switch. Today, it's 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 seventy five people send me emails first thing Monday morning. You know, it's like, OK, now I'm just dealing with last week and not surprisingly the whatever pick the number, I don't know, a thousand new emails a week or whatever, a couple of thousand emails a week that come in.

You know, it's 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 when I come back to this onslaught and I live again the previous week. So it wasn't as though I got to not experience that week in the rest of my world. I had to go live it again on Monday morning.

And by the end of the day, Monday, all of the things that happened over the week were again in my head versus if I just deleted the week. Yeah, some of them were important and they'd surface again. But the vast majority of them were not important, just cognitive dissonance of overhead.

I didn't second was cheating. Every hotel has a computer connected to the Internet. It's you know, it's really sneaking into the refrigerator at midnight to have the ice cream. Right.

And like, you know, cheating the best diet ever, cheating in a way that undermines everything you're trying to do for yourself.

Right.

So on Wednesday, it's like I just go check in and see and boom, the whole everything you've just done is, 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, you know, kind of like not the contract that we had to your words match your actions. No, that's the foundational thing. So there's like getting through that.

Then there's the I only have this one thing I have to do this week. Right. This one really important thing that that just can't wait the week. In 20 something years of doing this, I don't think there's actually ever been one of those. I mean, I've made them up right. And I've I've had plenty of them that have distracted me, but I don't actually think there has ever been really one of those. If there really was one, you'd move your vacation.

Right. You'd move the week to another week and say, look, I really you know, we're on the road show for taking this company public this week. And I have to be involved and I can't be off the grid. OK, well, let's move the week. So, you know, there are a lot of things like that that took making mistakes, like it wasn't like, OK, 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, the last week of the quarter, is there any pattern to how you think 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 version. It's called V, whatever my age is. So I turn 50 for last December. So I wrote Befouled V five fifty four and the year before I wrote befouled V fifty three. And oftentimes around that we'll sit down and we'll look at the next year and we'll, we'll try to get ahead of the calendar nonsense and just block out some weeks.

But they're not for weeks that are necessarily just convenient for me because Amy has a professional life, she's on the board of the Nature Conservancy, she's on the board of Wellesley College, where she went to school. She's got some other responsibilities that are part of the schedule. So some of it is just navigating our collective schedule. Some of it is also when we need it. So there are moments where we'll have it, you know, and it's a month from now and we'll look at each other and say we're we're frid, we need a break.

And I would say even in sort of 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 twenty. Twenty 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 twenty twenty. And therefore all of this stuff that's a trippier trip.

Their thing, their thing, they're none of that matters. So let's look and think what tempo we really need so that we can maintain the intensity of our normal life pace. We have learned, by the way, that Saturday to Saturday is the trick. We used to come back on Sundays. It didn't it didn't give us enough gear down time. And 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 way. It's just enough space. It just gives you a more gradual off ramp, on restaurant, on ramp or on ramp and off ramp, excuse me, the next question I have for you may be related, may not be related, but there's a there's a line here that I have and my notes, they can't kill you and they can't eat you. Can you provide some context this place?

It's one of my favorite professional moments ever. Maybe one of the most important ones ever. That line was said by Len Fazlur, who is my one of the two guys that bought my first company. Two guys were named Len Faslane. Jerry Parker partners in a company that was called Amerada, which ultimately was a public company co-op up by GE Capital. Len is my closest mentor, is the person I've learned the most about business from over my career. He's in his late eighties.

He is just spectacular, a spectacular human on many, many, many dimensions. We had co-founded a company in nineteen ninety six, so Len and Jerry bought my company in nineteen ninety three. GE bought their Mérida in nineteen ninety five and Len and I started with two other people. Raj Bhargava, an entrepreneur I've worked with a number of times, and Steve Max, who also had had a company bought by Len in nineteen ninety six, and that company was a company that bought Web hosting companies and we did a consolidation of Web hosting companies.

That really was one of three companies that create a category called application service provider. And ASP was a precursor to software as a service or SaaS. And there was like a rise up at the end of the 90s and then a completely collapsed in 2001, 2002. And of course, you know, 20 years later, software is delivered on the web online. That was essentially the business that we were we had created. We just didn't in the end, we didn't execute it correctly.

We bought a bunch of companies, I think about twenty five. We went public in nineteen ninety nine. We had a peak market cap of right at three billion dollars back when a market cap of three billion dollars was a big market cap for a tech company, company was called in Alliant. And when the Internet bubble burst, we had mastered that. We built about a two hundred million dollar your business. So pretty sizable company. Fifteen hundred employees.

And Len and I were co-chairman, so we didn't run it. We had an opera CEO who ran it, but we were he was full time. I was part time because I was also a partner at at the time. Möbius, we mastered the art of losing five million dollars a month. So we have 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 five million dollars 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, you know, our problem was that we've mastered five million dollars of loss a month.

He'd only mastered a million. So when everything reversed, he was able to get to cash flow break even we weren't. So we're now on the downside of the utter collapse of this business that at a moment in time had been the most successful thing I'd ever been involved in. And I was a co-founder, so I had a huge amount of personal value tied up in the stock that then was everyday 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 or as the same time frame. And when I would go to New York, I would stay at Lens House. I had an apartment in the city, but a lot of the office was in purchase. So a lot of times I would just stay in purchase because 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 like take a bagel and I cut it in half and I put in a toaster and I put cream cheese on it. I make a cup of coffee. And then eventually he'd sort of wander in and we 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. Is because beautiful house in Harrison, this little tiny kitchen table in the corner, and I'm chewing on a bagel, I didn't even bother toasting at a pretty grim news this morning, just like gnawing on it, like, you know, a depraved dog or something.

And he comes in and he sneaks up. He just comes in behind me, puts his arms around me, like in that big hug somebody gives you from behind. And then short he's like five five. It's like Yoda, like a Jewish Yoda with your 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 ya and they can't each suit up. And he he didn't need to be doing any of this work, right? He could have said, fuck it, I don't want to do this anymore. Why are we doing this? Like he was he was in that thing till the end.

He felt an obligation to do the work even as it was all falling apart, even even with 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 was a powerful moment for me, and, you know, I've had many, many other up and down experiences since then, but ultimately, you know, 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, what you've got to deal with in your life. But in the context of, you know, the US in business, entrepreneurship, trying to create things, you know, those things are true. They can't they're not allowed to kill you and they're not allowed to. Thank you for explaining the back story.

And there are so many other bullets that I don't want to take you through every turn of the roller coaster for like the first 30 minutes being Bradfield's version of misery, just like putting a cat in a pillowcase and wagging against a tree.

That's usually not what I do on my podcast, but I, I it is leading somewhere. I do promise that. And I'll just 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 now, people might be inclined to think, well, Brad, you know, he has this illustrious bio, has all these successes. I guess when it's bad, it's really bad. And when it's good, it's really good.

But there are also stories about, for instance, some of your best investments like Fitbit, where even in the midst of this meteoric rise, you have these emergency board calls and potential product recalls and product recalls, all for the right ethical reasons, where you're puking into a garbage bin after phone calls and having these really difficult experiences and visceral reactions.

I'm going to use that as a segue to a blog post. And this is pretty recent blog post from twenty twenty. But this is quoting from that blog post. I'm officially DSM five three hundred point three 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 twenty thirteen to talk about these struggles? 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 in a often in a very positive way.

Right. It created focus it an 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, you know, I'm one of those kids growing up. My dad was a doctor. My mom was an artist. We grew up in Dallas, Texas. You know, we had plenty of resources. It was an interesting place to be in the seventies and eighties. I think there were two thousand kids in my high school, 15, I don't know. Fifteen hundred kids in my high school, some big number. And four of them were Jewish.

So, you know, I had funny holidays and I had some moments that were not great moments as a as a Jewish teenager, sort of 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.

And I remember, you know, a month in, everybody has to take physics as a freshman and get a test a month in. And I know I didn't do well in the test and I got my grade. I got twenty. Right. As a kid. Never made twenty out of one hundred. I got twenty.

And I never got I mean, maybe I got to be in some English thing, some like I thought I was really good at physics. I got twenty. And 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 like I closed the door and I know what to do. Like how do even process it? Turns out class AB on that test was thirty two.

So I actually got like A B minus C, like who the fuck gives the first test so that the class is A 30 to amet like that's what they do. They just they they make you very aware that you are you know, there's a 10 percent of the people there are off the charts, but they make the other 90 percent very aware. Yeah, you're smart kids, but you're going to have to work hard. So, you know, college.

I was successful. I started a company. It was successful. I, I married my high school sweetheart, not Amy. I was in a PhD program at MIT at a very young age while running my company. Right. Externally, like everything looked awesome. And then three things happened in fairly short order, remember, I'm anxious all the time, so I have 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 to get kicked out of the PhD 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. Same at all levels, same that I was depressed.

Fortunately, my PhD advisor, who to this day is still, you know, a wonderful substitute, paternalistic figure from a guy named Derek von Hippel, connected me with his therapist who was a classical Boston psychiatrist, turned out that OCD at this time was not well understood. It was just starting to be better understood. Fortunately, I got diagnosed with that. So, you know, the treatment that I had, which was both CBT and medication, was highly effective, cognitive behavioral therapy, certain type of therapy where it's you know, you think about therapy with like, you know, sitting in 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, 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. Like, 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 taking a red eye to New York the night before the towers fell. So I. 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. Right. That was at the tail end of the collapse of the Internet bubble.

So kind of everybody in my business world was completely a mess. And now all of the United States is a mess for a couple of months because we're all struggling with we've been attacked. We've had friends die. What does this mean?

That 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 could really that I really was in the midst of. And in two thousand thirteen 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 run, 50 mile race in April. Of 12, so I overtrained, are trained a lot.

I was working a lot in my business world, was going very well between Foundry Group and TechStars, had a very healthy relationship with Amy. I had lots of things, but I was working really hard 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.

Sounds like a country music song. Sometimes I ended up with a kidney stone that I had been ignoring and just avoiding. Never mind that blood comes out when I pee. No big deal. I'm sure that'll go. I just ate something wrong. And on and on and on. And sort of in the end of this, at the end of twenty twelve, I was physiologically exhausted, just completely kaput. And had this kidney stone surgery, which I had a very big kidney stones, 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, OK, let's get back to it. And I went to CBS in Las Vegas Computer Electronics Show, which is the second week of January. And literally within two weeks of getting into Vegas, getting to my hotel room, I'm in bed with a pillow over my head. And I know I'm totally screwed like I've got I'm in a depressive episode in twenty twelve several.

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 is probably the first love of the stream and there was like a pop of oh my gosh, this person, how could this have happened and then sort of it would drift away. 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 in some other way.

Brad Pozner, 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 that's a really that is not an addiction.

It's a good thing to say. It's a good thing to interrupt with. So in my thirties, I was still pretty ashamed of being depressed, but I realized I was depressed out in the open. By the time I got into my forties 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 it, 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, is I had been in this partnership at at Möbius 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 start in twenty seven with that framing during that period of time, all for 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 Joke, many people like that who supported me through some of these depressive episodes, even if they weren't totally tuned into what was going on with me. As we got older, we had longer conversations around them. And then one person in particular really changed how I approached it, which was Jerry Colonna.

And I know Jerry and he did a great podcast with you not too long ago. Yeah, the coach with the spider to do so.

So Jerry 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 nineties. I knew Jerry when Jerry first started working with Fred Wilson, when they started their firm Flatiron Partners on your Jerry. Much better than I knew Fred and 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 2000, 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, we're where we're 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. You and Jerry finally disappeared for a while. I could handle you. And there's some it was said in jest, but it was 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, you know, as 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, you know, he's coaching now and, you know, he's really pulling out of 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, you know, 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, you know, the depth of the depression is something that we we talk about pretty openly and 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 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 right on the investor there, 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 like I always think I've been a pretty I am what I am and I try to talk about it very openly. But he says you're holding back on this dimension. The fact that you don't ever say you take medication, you're holding back the fact that you don't talk about your therapy, you're holding back.

So I carry that with me. And when I had this depression in 2013, I immediately went back and I had been in therapy since I was in my twenties. 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. Just kind of sucks. And 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, like 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 are like, why are you saying this? The bad guys are going to get you people that don't understand why I'd say something like this. Well, why would you expose your weakness? Plenty of you know, like when when I remember when Fred and I started blogging and 2004 time frame, lots of people said lots of voices.

Lots of our peers said they must have way too much time on their hands to write blogs. Right now, everybody writes blogs, but it's kind of the same thing.

It's like now, you know, I don't really care what anybody else says about it. This is this is going to make me feel better to let myself let go of the shame and I'm going to let go of the 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 or four months, you know, I don't know the number.

Fifty, one hundred people whose names listeners would recognize well known entrepreneurs, well known investors, some 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, you know, because then all of a sudden, Inc magazine wants to write an article about entrepreneurs and depression. OK, find your own irony in that article together, like 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. And that created a positive feedback loop, which over time essentially obliterated the shame, didn't just make it go away, it obliterated it. It's like 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, you know, if you look at the evolution of Jerry and if you read his book reboot, like just understanding that if one wants to have.

Put your adjective in like it doesn't have to be better, more satisfying, more success. 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 craft 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. Right. Because and the Warren Buffett words, I won the genetic lottery. Right. I'm a white male in America. I happened to be in my mid 50s. I got plenty of resources, like 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.

Just a quick thanks to one of our sponsors and we'll be right back to the show.

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You mentioned that Gerry's magic is up front 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 a question. 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 start crying. Right. 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 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 walking 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 doors 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 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 a Harvard Law School waiting for the professor to point at you next, you know, to talk about the case and explain what happened at Harvard Business School or whatever, wherever they do shit like that.

I didn't go to Harvard, so I get 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 in a hostile way, not an aggressive way, not an attacking way, just in this Jerry way. And I don't have a label for that, at least for for my experiences with him.

Take people to a place where they realize, wow, OK, what is important to me? Very, very quickly, yeah, he's 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 posed 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 being said.

You know what what is 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 found really, really fruitful.

What about how are you complicit in the conditions that you've created. Right. Is so powerful to reflect on?

It's a conversation that Amy and I have been having for 30 years. Right. I work too much. I work a lot, I work, you know, 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 like I have completely? I mean, you try to. Right. You have the freedom to do what you want to do, where freedom is a very American word in some ways.

Very poignant word in this moment. But as, again, white men with resources, we have a lot of freedom relative to many other people, most other people on planet Earth, 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 and carve out the time to look at that, think there's a tactical OK, 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 sack and man, even with things that seem so obvious from the outside to, you know, my best friends, I don't see them. And I think that's true for many people, right. When we're in complete denial of how we are creating those conditions that create.

Our unhappiness creator happiness, that's good, but create our unhappiness, create our limitations, create our put whatever box around and put a negative sign in front of it. And he again, he is good at poking through that, not touching it and tapping it and but 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 in this is what often happens when people self select. To interact with someone like Jerry is someone will break the ice and really express vulnerability, which gives you permission and sort of grease the skids for you to do the same.

So in some respects, you might anticipate that that being forthcoming and vulnerable in a group environment would be harder.

But I think for a lot of people to actually easier. So I do think there is something, a good insight.

I mean, it's probably one of the reasons why group therapy is a thing he he and reboot his company reboot have done. They started off doing CEO retreats and then he and I, I hosted a number of VC retreats. I don't know how many we've done now, five or six. And we do 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, you know, nonprofit fundraisers or dinners or whatever. And he and the reboot team would 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 v.C ones, and then having gone for between a meal and a day to the rest of the week, once everybody shows up with their armor on and, you know, imagine a bunch of folks showing up to afford a thing like this and 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. 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 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 call it let's just assume it's a technical founder, right? Someone who has kind of an engineering mind. 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 reminded me that I never answered why three's my magic number.

I will come back to that. So I've 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 our principles therapist, my IPSC adviser, 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. We went to 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 there were malpractice is loaded.

Right. I felt attacked for the entire 50 minutes by her therapist and that was it. We didn't go back in like our our relationship was probably already done before I went to a therapy session or certainly was done before I went to the therapy session. Just got to that point. So I already had a bad experience with Eric's therapist. The other thing is his name was Dr. Mogel. And I thought for an entrepreneur, that was the perfect name for a therapist.

And but I was 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 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 did for four years, I said I. I don't know whether this is a four year thing or a 20 year thing, but I want somebody who can have a 20 year relationship with because I'm in a place in my life. I think I was forty seven. I know I'm in mid-life.

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, you know, it's Boulder. I want somebody who has, you know, classical training. But I want them to be, you know, earthy, crunchy hippie Budha, whatever I said, I want that in my life at this stage.

And he said, I got the perfect person for you. And it it was a, you know, classically trained psychologist, Nurse McAndrew, his last name is his first name and his first name. His last name, which which got me a hello. And he there's a school in Boulder called Naropa that was one of the very first alternative schools in the country. May have been the first one that was Buddhist, you know, and very famous from the nineteen seventies, a key part of Boulder.

And McAndrew teaches at Boulder. So he was a Naropa professor. Jerry may still be has for a long time been chair of Naropa. And, you know, you kind of go on his website and he is for high achievers, for entrepreneurs, for people that are, you know, athletes, serious, again, serious high achievers. And you read it. And it's like the mix of high achiever and Buddhist. And it kind of jumped off the page at me.

And my response was, yeah, OK, what the fuck? I'll try this. And it's been great. By the way, I want to say it's been great.

Like I've had plenty of really crappy sessions. I've had plenty of moments where I didn't want to go know. I've gone through phases where I passively avoided things too busy. I need to cancel this one. I'll see you in two weeks, like lots of my own shit getting in the way. And and MacAndrews is very, very patient through all that. Back to your question, I have recommended many, many people now to him, not to him as a therapist, but to him as a referrer.

So one of the things that I find as a really useful thing is that it 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're, you know, 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 we'll do an hour session or a 50 minute session with the idea that they're not your therapist, but they're trying to make a few referrals for you.

The other place, if you have a good doctor that's general practitioner who you 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 their homework assignment, and that's the key, it's not that, it's what you're really doing is your shopping and you're asking even the people you're talking to who they think you should talk to.

Now, if you're an incredible destress, you might just land with a person. But if you're in a place where, like, I really want to make progress, you're 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.

What is the role of therapist versus coach for you?

Is the therapist, the salvin, the coach, the whip, or you know, it's just like looking for monopoly pieces, right?

The here's how I describe therapy and here's how I describe coaching for therapy. I pay somebody armi. 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, you know, 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, right, 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 would 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 the 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 in 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.

Stop in the whip is kind of OK. I mean, the coach is the whip, right? The coach is the one saying. But a really good coach is also, you know, there's there's part therapy. And I mean, Jerry talks about, you know, to be a great and the reboot way is a combination. Their methodology is 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 injury, 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 really, really great.

I like that really great at doing the wrong thing.

It's the intersection of those two were really great at doing something that you fucking hate.

Right. Well, you hate this, but you're really great at it, so. But I'm not doing any radical self increase, 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 that's no way to live.

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 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 to 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, you know, as a person with OCD to try to control your environment.

Examples would be and this is why one of the the the things that people with OCD have is they're known as checkers or counters, right. To count things. They're constantly checking things. They're arranging and ordering things. And people will say, I have OCD when they're like orderly and clean. Orderly and clean is not OCD. It's only if if the thing is an orderly and clean, my mother will die. Right, 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, you know, it just the last example, the absurdity of it is most people with OCD are very germophobia and very don't like dirt. Wash your hands a lot. And so the whole idea of trying to straighten all the cigarettes on the street and touch all the dirty thoughts on the way to the office is just stupid.

But 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 your 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 home, when I got to my apartment at night, I had to turn the clock three times before I walked in the apartment, I had to close the door handle three times when I closed and I had to turn the clock three times and I closed it when I took a shower, had to turn the shower on, off, on, off, on, off before I could get in.

And then I have to turn it on, off, on, off, on, off. After I got out and then after I got out, because three's my magic number. I'd have to turn it on off on off on off again. And if I and on and on if I didn't do something three times, there's one my engineer brain kicks and I had to do it nine times.

I love three three days of OCD inflicted superstition and nuclear engineering in neurology. All right. So so what happens if I screw it up when I don't do it nine times? It's got to do it twenty seven times. Three times three times three. If you have ever had to do something stupid that is, you know, stupid, the wrong word, if you ever had to do something, you're trapped, right. You can't go do the next thing.

You have to do it. Twenty seven times you get it right, because if you don't get it right, you're going to do it eighty one 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. So if we're talking about links and breaking these 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 in 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 just I just want a commitment for that and know hem and hug, you know, 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 and and I said, yeah, I have it on my 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. Just how about if you make an online recurring calendar appointment from 6:00 p.m. Colorado time to 10:00 p.m. Colorado time on the first day of a month and have it repeat forever. I said, OK, 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. Twenty years of life, 10 years later, so what is it, a thousand something life dinners, which is awesome, by the way, we we have a little flexibility. There's there are definitely nights where we we will have it on the second or third because of what's going on. But we we really commit to it. We used to go out to dinner.

Now a lot of times we just do it at home. Timakova we sure do at home we often not always but often start with a gift exchange and the gifts could be trivial little things once you give me a remote control fart machine.

She's picked up a lot of jewelry and art from from it over the years. And folks, one dinner she gave me a Range Rover.

So, you know, it's a full spectrum of little I really hope it was the same dinner that you gave her that you didn't give her the pharmacy machine. That would have been less probably 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 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 twenty first of the month, I could wait nine more days or 10 more days, and it could be part of seven more days.

That can 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 set in the moment, the forward 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 who's 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 wife dinner part of a conversation might go five or 10 minutes and sometimes it might go three hours. And sometimes there was laughter and sometimes there were tears and sometimes they were both. And it's just such now, 20 some odd years later, a comfortable way to reground ourself as a couple roughly every 30 days in what is a very, very challenging and complicated world.

Now, 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, or at least in my experience, the delivery can matter a lot.

Do you have you guys learned anything about communication style when you're bringing forward grievances or anything along those lines?

I think we we've learned a lot over the years because we we used to not be very effective when we fought because we didn't know how. And a couple that says they never fight is totally full of shit. Right. Because we humans and we we learn 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 like physical striking or you mean pounding the table.

Anything like physical. 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 OK as pounding the table, you know. But but there's a big difference, I think, between pounding your fist on the table out of frustration and doing in a way that, you know, jerking someone's chair. Right, I think pounding fists on a table probably would be OK in our know how that's game.

But but certainly, you know, jerking a chair or shoving the other person or whatever is completely unacceptable. I'm 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. 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 for people who might be inclined to withdraw into themselves and just kind of blank out like Wally shutting down if they're happy, if they feel like they're being pummeled?

How do you counter with what's the countermove? One is I try to stay in the moment with the anger. And again, I think this is 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. One hundred percent. 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, an annoying as shit way, but in an engaging in 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 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 or the other tactic.

By the way, I use this. I try to use humor in those moments. We have lots of stories of us ending this. We're where she gets out of an angry phase. I hate to make her sound like a terrible person. She's awesome and she doesn't get angry very often. So it's not it's not that I live huddled up in the corner of my house waiting for the next outbreak. It quite the opposite. But, you know, in those moments where all of a sudden, you know, I'm jumping up and down with her in the air laughing and making jokes about things and spinning in circles.

Right. 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 gotten stirred up and it's spurted out. So it's kind of like, oh, that's the thing. OK, 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. Not it's not hers to apologize to me and 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. Right.

Which is not an apology. That's all. That's always a winner. Total bullshit, right? It's it's just. I'm sorry. I'm so sorry. You're responsible. It's just simple. It's I'm sorry and I'm sorry and hug and and you go on. Right. And and I should also say, like, I get angry too. It takes a lot. It doesn't happen very often, but I get angry too. And she she does the same.

Right. She reflects it back, engages fully, listens.

Of course I'm sometimes defensive, of course she 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, do you guys take any? And maybe in the early days it would be a better question for reflecting back on the early days since I'm thinking of, say, me and my girlfriend, I'm thinking of couples who are listening to this or partners for that matter, who might want to in some fashion emulate this notes, taking notes, helpful, hurtful.

Otherwise, too many thoughts on taking taking notes if 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 for us? It doesn't. I think it can be very helpful. I think it's very, very individualistic. I am not a note taker. I just not yeah, I have a good memory, but I also I have a memory that's a synthesising 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 learned by reading, so I've sort of learned about myself that the you know, a lot of people say if you write it down, if you take notes, cause you to remember it better. What I 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 has she's I did 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 the relationship, early 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 and 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.

You know, there is there is a reason that there's their sentence structure, paragraph structure, chapter structure in business books that can be tedious and will result in the business book only needed to be about 20 pages long. But for many of us, we have to 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 it's even triggered it. And the person who's angry may be articulating their anger in a way they think resembles what's 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 a, you know, intimate, trusted relationship with, if it's just some random person different in a sort of circuitous answer for me, writing stuff down is not helpful.

But I could see how for some couples it is. I think the practice also, by the way, of of the retrospective. Right.

You had to fight, you know, don't go off into your corners and each sit down with your journal and write what just happened, but agree agree to sit back down, especially early in a relationship.

Agree to sit back down on a couple of days, three days from now. Let's have lunch and let's talk about this. And between now and then, let's each in our own way think about like 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 like that. 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. We're 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. 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 what's your hit rate on undoing that?

You said 80 percent of time. That's incredible. Have three to four or four to five. The it started I didn't used to do it.

I used to work my work. Rhythm was that I would use half a day on Saturday to catch up usually in the morning. And then I do a long run on Sunday mornings usually. And then I work, I work another half day to full day on Sundays and even even into 2013, the number of hours per week.

Again, I stopped. Thankfully, I stopped having to keep track of the hours a week.

I worked at about twenty two. Amy didn't make me keep doing that for the last twenty 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, you know, hour or two hour in front of your computer, just catching up on stuff. Right, which is easy to dismiss that you're actually spending time working versus living a rejuvenating yourself or take care of yourself.

So when I 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? I just don't work a day, week. And by the way, when I was depressed, I was having trouble like getting out of bed. So it wasn't like that was a that was a hard thing to agree to. Yeah, that sounds great. And I'm not religious, but I'm I'm culturally Jewish enough.

The Jewish tradition. I'm like, you know, I know plenty of very successful religious friends, religious Jewish friends who take the Sabbath off completely, you know, Friday night to Saturday night. And so I just said, I'm going to play the week off the grid to Friday night to 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 reference, kind of defeats the purpose.

And we kind of use sundown as the trigger, although it's not a hard boundary. And, you know, Colorado in the summer sun doesn't go down to like 30 right now. So and we have a place in Alaska sometimes when we're in Alaska, you know, the sun doesn't go until 2:00 in the morning, like it's not quite the right trigger, but it's kind of the point where I'm like, you know what? I've had enough. I'm done.

And I'll I'll pick this back up Sunday and what I found over. I've been 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, you know, as we're dealing with a bunch of stuff on both the health side and the economic side and dealing with some stuff for the mental health side, just trying to rally a bunch of people in the private sector to help the state.

And specifically, we have a fantastic governor in Colorado. Jared Polis is a very successful entrepreneur and a good friend. And sort of in that period, I think I skipped three weeks. Right. So I worked all day Saturday, all day Sunday. And by the end of the third week of that, I was broken. Like I could feel I could feel I was done. Like I wasn't going to make it another week unless I took a break.

And so a lot of ways in in it's helped me sustain a pretty heavy work intensity over a long period of time by really completely disconnecting for that twenty four hour period for for some period of time, actually for a long period of time. I was doing screen free Saturdays to the best of my ability and I would use Google Maps for certain things. But outside of that, really texting to coordinate, meeting up with friends and Google Maps, outside of that, it was browser free, laptop free.

And you really do notice the gearshift or I should say the gears grinding when that gets removed for an extended period.

There's the flip side of it. I that I think is so amazingly wonderful in some ways. I like to take naps in the afternoon, so I pretty much take a nap every Saturday afternoon. And I remember this is a long time ago. I remember a Saturday afternoon. And I I'm a big reader and I, I just didn't feel like reading. And I had gone for a run and I'd taken a nap. And I was kind of bored, which almost never happens to me because I fill up my world with stuff all the time writing, I don't allow myself the luxury of being bored because I always have too much to do, which is a whole nother version of it's basically boredom aversion.

Right. Like, 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 some plenty of grist for the therapist mill. And I said to Amy, I kind of feel a little bored. And she laughed and said, Isn't it wonderful?

And it is really helpful to sometimes just sort of look out the window or, you know, sit in your backyard and feel like I actually don't have anything I have to be doing right now other than be right here. And for many people in today's world, it's hard to do. And so I've let that be part of it, which is, OK, 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, you know, take a deep breath, reflect and let the day unfold. You mentioned reading. I'm going to I'm going to have all roads lead to Colorado in this question I keep promising. But you mentioned reading.

I have a list here of some of your favorite books, and I'm just going to go through them real quick and then ask a quick question on this Zen in the art of Motorcycle Maintenance by piercing Battlestar Galactica Ronaldsay More Snow Crash by Neal Stephenson, Neuromancer, William Gibson. And if I'm getting this title correctly, the startup community community. Is that right by Mighty Networks. If we're looking at the first four, which are all fiction and you are recommending one of them to someone who has been a nonfiction purist for a long period of time, is there is there one that jumps to mind as the starting point?

So let me let me let me read segment that a bit, because they're they're not all books. So Battlestar Galactica, I wasn't sure if a TV show, Battlestar Glocke wasn't sure if it was based on a TV show. So but but but but it's worth it's worth touching on that. And then the startup community community is an online community that I just started a couple, maybe 10 days ago. From the time we're talking, that's part of the new book that I've got coming out at the end of July called The Startup Community Way.

I've been obsessed about the idea of startup community since I wrote the first book around it in 2012 when the phrase startup communities didn't exist. And so a thing I've wanted to exist since I wrote that book was a community for anyone around the world that was interested in startup communities, which is most entrepreneurs, but then lots of other people. And nobody had ever created it. So I just decided to create one. And I'm using a tool called Mighty Networks.

That's really quite interesting and well done. And in a very short order of opening it up to people, 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 of those three books. So Pearson's book is essentially a motorcycle maintenance is a book. I think anybody who makes anything should read. I recommend it to all entrepreneurs, I read it when I was in high school, and I've read it every couple of years since, probably read it every three or four years.

I listened to it on tape, book on tape once when I was training for a marathon just to see if it sunk in in a different way than it did.

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

So it just 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 it's easy to move through. So so I just I think that's a book every human being should read. The the two books I listed there, Snow, Crash and Neuromancer, are important books because they essentially are the books that created the precise age, the context we have today. And Stevenson, Stevenson and William Gibson are two of my favorite and two of the best contemporary science fiction writers.

Neuromancer was first. It was written in nineteen eighty four, and if you read it today you kind of go whatever, but if you read it with, if you time travel back to nineteen eighty four and read it, given our world in nineteen eighty four, it will blow your mind how he predicted and you know whether it's two thousand or two thousand and ten or twenty twenty. I just, just the number of things that he got right. As a predictive force in our not too distant future, not just technology, societal issues, humans against interaction with artificial intelligence, the dynamics of society, how politics work, how drugs work.

Long, long arc of things. Snow Crash is written in 1992. So just just before the World Wide Web begins, and I think the technology part of snow crash is brilliant, but even more powerful is the geopolitical part of snow crash and the geopolitical part of snow crash is so incredible against the backdrop of 20 20 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're not going to be allowed into New York. And so, I mean, this book goes way more granular than that in terms of the boundaries, but it's it's awesome. By the way, another book in that vein that I think is is. As good or better a book also the first book was written in the early 1990s, I believe, by a guy named Dan Simmons, is a book called Hyperion.

It's actually four books, the Hyperion Kantos, and it takes place over about three hundred year period. And again, all of these things that are folded together, it's not just science fiction, but it's A.I. versus human, it's religion, its society, its gender, its augmentation, it's a geopolitical all over use. 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 it's a pilgrimage where the first book that's the setup for the whole series is the seven protagonists in the first book telling their stories as they're going on a pilgrimage that, of course, has a very meaningful climactic end that motivates you to read the second book. The recent 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, my brother and I have one hour a day.

I'd like to give my hour to my brother. I'd rather read a book. However, I like to watch TV that our 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 ten years. And Battlestar Galactica, 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 whatever you want and then everything that happens around all the boundaries of humanity and society as a result. And the reason I like this so much and I'd put them so much at the top of the list for somebody who's not who's a nonfiction reader or anybody that just wants to begin, is that the best part of science fiction is worldbuilding? And science fiction authors that get the world building right and really know how to do it. The books that they ripped, 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. And Kate Jemison, who's a black woman who's, you know, 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 who's become a close friend, I, I helped sponsor him when he was writing his first couple of books. He's now, I think on book eight or nine or 10. That's 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 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 and then sometimes you write something and it's not so good and then you try again on, the next thing you do is a guy named Elliot Pepper. And Elliot has become in a category called near term science fiction writers that guys like William Hurtling and dinosaurs around, 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 Crashes, a spectacular book. It's such a fun book to read. Also on top of it and for for worldbuilding. I just want to throw another book in. If people aren't overwhelmed already, which is doing for Herbert Antwerp's world building. It's a middle class lower class.

It's it's the beginnings of the beginning of that genre. Yeah, it's I feel like you can learn almost all the leadership lessons you need from doing it is it is just truly spectacular work.

I'm going to toss one else on the one other on the pile too, for fun. This 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 twenty twenty.

And so he had to be done with it in February. So before the current pandemic, probably had income, it 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 twenty five percent of the book is about where we are right now. And for anyone who likes again, I put this in the category, it's it's 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 to last one 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 Chang and his 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 can live like you. The Paper Menagerie, which was gifted to me by Matt Mullenweg, really accomplished tech founder, CEO of a company called Automatic Mattiske.

You might see that MULLENWEG Automatic and then case. Both of those are short story collection.

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 Dooen. I still recommend it. But the Paper Menagerie and exhalation are easy ways to kind of play in the shallow end with with deep meaning without getting overcommitted. Colorado.

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

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 it's not my thing. I'm more of a loner than a joiner, I am more of a detached and are disconnected from a sort of in the middle of a kind of person. So. I think epicentres, 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 three hundred and sixty four days too many. It was never, never it never, ever felt like home to me and, you know, when you're in your college and you're in your early 20s, like the definition of home is tricky.

Like, what does that actually mean? What 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 like my third year of college or moving back Dallas. And I know 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 some day. And 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. And when I sold my first company, I was twenty eight and I told Amy that by the time I was thirty we'd be out of Boston. And we traveled a lot together and we like to explore different places, and she said her requirements were ocean or mountains and growing up in Dallas.

I didn't have either, so I didn't totally get that. But I'm like, OK, well, not both either. Right? And she's like, either I need one or the other. And growing up in Alaska, she had both. And about two months before I turned 30, she said to me, I'm moving to Boulder and you can come with me if you like. The strong hand. We're married, right? And I sold my company, I was still working.

I was doing lots of angel investments around the country. I was still I was traveling a lot West Coast, East Coast, Boston, New York, Seattle, San Francisco, L.A., occasionally somewhere else. We had been to Colorado a lot. She'd lived here when she was in third grade and I had come here skiing as a kid some and then those young adults and I and we always Colorado was just sort of the fantasy of it was a cool place.

You know, the rugged the rugged west is kind of a thing in our culture, you know, independent of what you think about Atlas Shrugged as a book or Ayn Rand, a philosopher, like the whole idea of Gold Gulch being in Colorado sort of stays with you, you know, and this idea that it's away from all the other stuff. So not not the epicenter that kind of appealed. And we'd been to Boulder. We went to Colorado for a two or three week trip and we'd been in Boulder like on a December, January day that was like 50 degrees on the Pearl Street Mall and a beautiful winter day that was not really wintery.

Kind of like remember this this is this is pretty awesome. So she told me we were going I had a staff job for the company that I work for so I could go anywhere. This was Amerada. So it was easy for me to just relocate from Boston because I didn't everybody working for me anymore. And 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 can Inverne and he moved away within a year. So we really moved out here not knowing anybody. Nineteen ninety five and 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, we'll try something else. And if it is, this is our place. And within six months, we knew unambiguously that Boulder was where we wanted to build our life.

We bought a house behind a state park in a place called Eldorado Canyon behind Colorado Springs State Park. We initially bought a piece of land with 40 acres and a house on it. Over time, we ended up buying the pieces of land around us and ended up having a little bit over a hundred acres there. We lived there for 17 years and eventually, as we got started to get a little bit older, we've 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 the story. So I'll I'll get to it in a sec. And now we're looking at the mountains rather than being in the mountains. And we have this real sense of expansiveness as we look at Long's peak each morning. And, you know, we have two big golden retrievers and they just kind of run wild on our 40 acres whenever they feel like it. Although one is old and not running so wild anymore.

Today, I would be able to answer your question when I was 30. I couldn't today. My answer is I don't like cities. I don't like being around a lot of people. I can do it, I can put up with it for a couple of days. We had an apartment in New York for three years, and I probably spent a week, a month in New York, you know, between 97 and ninety nine, not necessarily a consecutive week, but over the course of a month, you know, two days.

Three days. That was OK. Same thing with San Francisco, three days, San Francisco, then I just want to get out of there. I can't stand it. But then the peninsula, I spent an enormous amount of time on the peninsula during my Softbank and Moebius times. I lived most of the time between nineteen ninety nine and twenty six. When I was coming out all the time, I lived it. My partner, Heidi Rosens house in Atherton.

I mean, it's a beautiful place. It's not my place. It's not where I feel at home. And I had formed with Amy, I think the two of us formed it together, a pretty deep belief that it was important to pick the place you wanted to live and build your life around it rather than go to a place that you felt like you should go to because there was an opportunity there. And I've had this very long standing belief, partly because I've been, you know, started and invested in countries all over the U.S., 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, one hundred thousand people have a vibrant startup community. And one of the things that's been most powerful to me about Boulder, at least from the time period in nineteen ninety five to probably 20, 15. So 20 year period for me, maybe a little bit longer, was I was in a place that was big enough to be interesting.

One hundred thousand people are more but small enough that I could get my mind around it and what was going on as I tried to understand the dynamics and the characteristics of building a vibrant startup community. The last comment on why Boulder and there's positives and negatives that I understand today, having lived here for twenty five 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 Los Angeles isn't a city. And as somebody told me once, the number of its 80 something cities, you know, in one 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, Amy and I also have a house in Homer, Alaska, which is a town of five thousand people. That's where she grew up until she was eight. And we used to go to Homer for a month. Every year. We still go to Homer, not as often, maybe every every couple of years. And it's, again, a totally different yet another thing to live in a town of five thousand people, you know, that's 60 miles away from the next town that has ten thousand people in it.

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

We built a house in Aspen a couple of years ago, and there was something that we had a house in Keystone, Colorado, for a long time. I love running in the mountains. We love being in the mountains.

There's something about Aspen that we were drawn to because of the restaurants and the the town, but also the ability to be in the mountains and just be disconnected from it all. We pretty quickly we didn't realize it till after we had a place there and were living there on a part time basis, that it was an enclave as well. Right. And a whole different level of enclave in terms of privilege and the dynamics around it. And while there are elements of that that are appealing, there are many elements of it that are very disorienting, confusing and not necessarily healthy for the city.

And I understand those things much clearer today than I did even three or four years ago. You know, 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 prie covid even lack of travel and sort of reflecting on, you know, what and where I like to be. And then most interestingly, how our technology today has changed all that.

Right. You know, pretty covid. If you had said to somebody, 90 percent of people who work in office buildings are. Ninety five percent of people who work in office buildings are going to be working from their houses for the next three months. Know 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. Work just fine. You know, 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. He was one of the people that basically helped create the microbrewery industry and the idea of a microbrewery in the first place. I don't remember the first time I heard this word from I think it was one of a state of the state speeches.

He used the word dope Ophelia and took Ophelia is love of place. And I think to be truly satisfied, 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 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 to have feelings 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 an enclave 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 it 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 just love to hear how you think about applying complexity theory to finding it first to life, to what you do to 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 write. 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.

We had started talking in twenty seventeen. We met each other. I like the end. We done a few things together around startup communities, talked about a few things, had a couple of 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, like the book that 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 get the question and I know I mean, even though I'm not deep in this, get the question of, you know what now, right.

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 a book like A Startup Weighs fifty thousand sixty thousand words, probably wrote twenty five thousand words.

And we had we were both unhappy and it was hard and we weren't there was no rhythm, there was no cadence to anything we were doing. And Ian called me, he moved to Boulder for a while and then moved to London and he called me and he said, I have come up with a framework to use to describe what the startup community was said, OK? He said what a startup community really is, is a complex adaptive system. It's all I said, I said silence, and I said, one hundred percent 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 way and for how people think about it, I think the idea of complex systems, plenty, it doesn't have to be the exact precise academic thing. Think of three types of systems, simple, complicated and complex.

A simple system is making a cup of coffee. Right. I listen to Saskatoons 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 and I listen to Madeleine Albright's podcast with you. And that really inspired me. And I went back and I poked through and went looking for some other podcasts that people that I knew and I really liked and respected.

And he talks in the podcast. You all talk about how he makes a cup of coffee and his obsession with cupcakes. And may 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 it's a simple system. You have an input and a deterministic output might not like the thing you taste when you taste the output, but it's a deterministic output. A complicated system, again, has a recipe or a playbook, but it's got a lot of different steps and the steps can be done in different order. But you end up with a deterministic outcome doing your monthly, quarterly or financial annual financial statements.

It's a complicated system, doing a financial audit is a complicated system, it's replicable. Building an airplane is a complicated system. It's really hard to figure out how to do it the first time. But once you've done it, you just keep doing it. A complex system does not have a deterministic outcome, you cannot predict the outcome from the starting point and the inputs along the way generate outputs that become inputs. Into the system, there are lots of fun examples of complex systems, but the one that I think a lot of people immediately get is raising a kid, because even if you don't have kids, you were a kid.

And if when you're born the day you're born. Your parents say. This kid is going to go to Harvard, become a doctor, become a cardiologist, dot, dot, dot, dot, this is 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 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 recipe or sequence of steps to 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, I knew we both knew a fair amount about complex systems and complexity theory prior he had and had been fascinated by this, which is why he landed on it. I had been fascinated by it going back to the 19 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 the early books that came out of the Santa Fe Institute research and talked about Brian Arthur and the idea of increasing returns, which are really just exponential curves, talked about flocking behavior talking. And Mitchell Waldrup does that. Sandra and Mitchell Waldrup, the complexity subtotal, the emerging science at the edge of order and chaos.

So that that book I read, I remember laying on my couch in my apartment on Baystate Road reading that book and just sort of must have been nineteen ninety or nineteen ninety one and just, you know, having my mind blown like it was just like yup, yup, yup. And you know, Gamefly Conways came alive and sort of all the stuff that 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.

As 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.

And what does that mean? And especially what does that mean over a long period of time, because of the inputs are becoming outputs, et cetera? I mean, the thing that today to this moment is 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 Cuban crisis is not a crisis.

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 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 love, contagion in this context, right. There is an idea of positive and negative contagion, and covid is obviously extremely negative contagion. But in business, we talk all the time of positive contagion.

The whole idea of a viral loop, you know, for anybody that runs any business that's consumer facing is is positive contagion. And if you scale it up to society, that's what we're talking about in the startup community. 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 adviser as opposed to an investor, you've seen how one company with the graduate slash alumni and the factors that made it.

Such that it could develop this this vibrant ecosystem are really fascinating and I mean, you've 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.

Right. But you can't architect it based on the current view. So I'm looking forward to the Serb community way.

That last statement is exactly correct and superimportant. Your Ottowa example in your Shopify example is an example of what 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 top Ophelia, if they care about their city, and 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, you know, 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 its 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 and 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. And I can't not say this because it's a fundamental part of my what I call the Boulder thesis around startup communities is that you have to take a very long term view.

Like to say, I used to say you have to take a 20 year view from today or give or take a 20 year view. Now, I say you have to take a 20 of you 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. You're not part of it anymore. But that's OK because the next generation of people are taking that long term.

Yeah, it's 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 kind of talent.

Poaching and musical chairs of talent is so prolific. Whereas if you are the game in town and you are the 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. I mean, you might even say the same of, say, a Duolingo in Pittsburgh, although Pittsburgh certainly as Carnegie Mellon and incredible talent recruitment if you're looking at a technical talent.

So it's it's been really cool to see an important part of the team.

Is it I don't know the Shopify founders well enough, but my guess is they're not playing a zero sum game either.

Right? 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 they've said they've seeded apps and they're very active investors in Ottawa like they are. They're definitely a rising tide raises all boats.

And that's that's such a powerful moment. Right. Think about that, though, in the community. Right. 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 describe the essence of it now in two thousand seven, I don't know anybody that talk that way.

And I remember when we started TechStars and Boulder, people like Boulder, why would I ever go to do a thing in Boulder and the nice mountains?

And, you know, today, if you look at at Boulder as a startup community, you look at Denver as a startup community, they're connected. But there are two distinct things. You know, the amount of that positive feedback loop, that entrepreneur or recycling from companies like Zao and Rally Software and Data Logic's and send greed and now twilly after they bought Sandgren and on and on and on. I mean, it's you know, 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, you know, a hundred or whatever, 150 fifty years ago as cities were starting to really be developed and the people in the cities who had generated economic wealth. Continue to invest in the institutions in their cities, right? The schools, the museums, symphony, the cultural institutions, a lot of cases, the actual business institutions, the sports teams. Right. Mark Cuban owning the Mavericks is an investment that he makes in Dallas.

I mean, it's a satisfying investment for him, but it's he didn't make an investment in a sports team, not in the city he loved. He did it in the city he loves.

Yeah. Michael Dell in Austin. Siringo Asatru.

Brad, I feel like we could talk for 70 more hours and maybe sometime we should. But I think for around 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 Tim Dell blog Forward Slash podcast. You're going to search Felde afield and it'll pop right up. People can find you. It felt thoughts fell dotcom. There's Foundry Group, Foundry Group dot com for the social.

Is Twitter the the best social location for you at Befouled.

Yeah Twitter is fine and people tweet at me, I'll, I'll respond to them totally fine. My emails pretty easily discoverable. So just Bradwell dotcom people have things they want to reach out directly about. I'm always happy to email. You may get a few. I'd actually rather I'd rather get emails and the random tweets. I look forward to my call. I look forward to the Tim Ferriss flood of emails and just read in the subject line, WTF, so I know who to be annoyed with.

I'm I'm just I'm just going to forward them all to Seth Godin. So so we're good. So anybody, anybody that wants to get an email to Seth Godin just sent it to me or Jerry and I'll send some to Jerry randomly. Maybe I'll toss Fred in for good measure, Fred. You handle this for me. Subject line forward, WTF? What the hell is going on? But it's unfair to blame.

I don't really besmirch my good name. Obrad, this is this has been a lot of fun. I want to ask one last question, which is one of my favorites doesn't always sometimes difficult one to answer, but if you could put a message on a billboard, metaphorically speaking, to get something out to billions of people, let's just say it could be a word, could be a sentence, could be an image, could be a question, anything a quote, anything noncommercial.

What might you put on that billboard? I would say, can I have two billboards, one in the Bay Area and one everywhere else you are billboards.

I think my billboard for the world would probably be. I like that. Just breathe. Another billboard, which is not probably the Bay Area billboard, but for place, there's plenty of places would be some version of don't believe your own bullshit and maybe the sequence breathe or don't believe your own bullshit.

And then 30 seconds later breathe. And then I come back to they can't they can't kill you and they can't take it.

Which one for Silicon Valley would it be? The the don't believe your through. I'll let them choose probably our dotcom 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, 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 in things like this out for other people to the extent that anything is useful anywhere. I think you have your master of your craft and it's wonderful to it's wonderful to watch. And it's an incredible honor to participate. Thank you, Brad. I look forward to our future conversations, hopefully more than a few. And to everybody listening, I will have Schnitz, as mentioned to everything we've discussed, teamed up Longboards podcast, just search for Felde Field and it'll pop right up with all the goodies, including links to the new book Startup Community Way in the second edition of Startup Communities.

And until next time, Briese experiment will be safe.

And thanks for tuning in. Hey guys, this is Tim again. Just a few more things before you take off. No. One, this is five Bullett Friday. Do you want to get a short email from me? And would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend and five? Black 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 into the world of the esoteric as I do. It could include favorite articles that I have 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 four hour work week dotcom.

That's four hour work week dot com 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. 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 twenty five to 50 percent off of normal retail prices with no only prices for anything.

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