Brad Feld

Category: Personal

As I schlep through the San Jose airport at 5:30am to catch a flight to Los Angeles, I have a moment of nostalgia. I haven’t been here in a while since I’ve dramatically cut back on my travel, but I’ve probably wandered through this airport pre-dawn 50 times.

Thirty minutes ago when I got here, the airport was empty. I just had a morning call with Amy and now I’m watching the gate area fill up with mostly sleepy and occasionally noisy people. The smells are a complicated mix of antiseptic, sweat, deodorant, and perfume with cooking food mixed in. It sort of feels crisp and contemporary here, but in a way that I know will feel dated in a decade, like most airports.

Today is only the third day on the road and I’m already exhausted. Monday was a full day that ended with a flight to San Francisco. I spent the night in Sunnyvale and then had an early morning of video conference calls before going to over to Return Path to have a long board meeting followed by dinner.

As I crawled into bed last night, I knew it would be an early morning since I’m on a 6:30 flight to Los Angeles. I have a meeting in downtown and then head back to the airport for a flight to Seattle where I’ll spend some time at Techstars at the end of the day. Thursday I have a morning meeting at Glowforge followed by a Moz board meeting and dinner. Early Friday morning I fly back home to Denver.

I did something resembling this every week for the better part of 20 years. I suppose I enjoyed it for a while or else I wouldn’t have done it. But whatever it was that I enjoyed eludes me this early morning.


I love to sleep. I’m at La Guardia heading to Aspen for the weekend. I got up at 4am to make my flight and I feel like the guy on the left.

Brad and Stan sleeping at airport 1990

The guy on the right is my dad. I don’t know when or where this picture was taken, but my mom sent it to me a few months ago. One of my super powers is to be able to fall asleep anywhere I am almost instantly. This is especially true on airplanes, where the pre-flight ambiance puts me immediately to sleep.

I clearly got this from my dad, who is also a champion sleeper. Whenever we are together, we eat chocolate ice cream at least once a day. And we take a 90 minute afternoon nap, which I have always felt was once of the most delightful experiences a human can have.


Even though I haven’t been in school for a long time, I still have some tenuous link to the idea of summer vacation. Well, not some much vacation, but a mode shift from going to class every day to doing other stuff, such as playing tennis at least eight hours a day (age 10 – 14) or writing software products (age 17 – 21).

A few summers ago I did a hard shift to maker mode. I did some of my most creative work in a while that summer, including writing Startup Communities and getting started with Amy on the book Startup Life. It was also a powerful summer for some of the companies in my portfolio and I was able to spend deep time with several of them on their product rather than just reacting to all the inbound stuff that was flying at me. I also got in the best physical shape of my life. I worked out – mostly running and biking – almost every day. I slept plenty. I ate well. I spend a lot of time reading and hanging out with my beloved.

At the end of the summer, I blew it as I shifted out of this mode. The fall started with a bike accident in Slovenia and ended with surgery to remove an 8mm kidney stone. But that was only the beginning of a slide into a very deep, six month depression which finally ended in the summer. I didn’t plan for an annual cycle, but that’s what happened on that one.

While I feel mentally healthy right now, I realize that I’m extremely tired. Amy and I slept an enormous amount of the time we were in Paris. While we usually have an epic Parisian meal two or three times during the week, we only had one at the beginning of the week and then cancelled the others because we just didn’t feel like it. We had an amazing visit to the Picasso Museum, but then spent a lot of time laying in bed reading or just wandering around aimlessly, and then heading back to the hotel to take a nap. The heavy fog of fatigue, which settled in on the trip, hasn’t lifted. I’m sure the endless rain in Boulder isn’t helping, but I’m aware that it’s time to shift gears again.

On top of that, I’m pretty tired by the noise in the system. I was tired of it all spring and wrote a few things about it, but the gap between real signal in the entrepreneurial world and the endless noise is at a volume that is very high. I filter much of it out so when it eventually breaks through I know I need to add a new filter, or recalibrate my filter.

At the same time, I’m extremely interested in many of the companies we are investors in. So, I know I’m not reacting to the work, or the types of companies I get to work with, but the systemic noise that isn’t about creating, doing, building, and thinking.

I’m using Memorial Day to Labor Day as my marker for recalibrating for this summer. I’m not going to use the 2012 Maker Mode summer approach but I’m going to design something else. I’m going to let this week roll over me without fighting it as I think about what the recalibration for the summer is, but the new mode will start in a week.


For many years I was often the youngest person in the room. I started my first company at 19 and had already had several bizarre “too young” experiences by the time I was 21. I vividly remember almost losing our largest client at the time because they had taken my partner Dave out for drinks (he is three years older than me) and they somehow pried out of him that I was only 21. That generated a lot of anxiety for a week or so.

I’m at the Big Omaha Conference today for the first time. I’m a big fan of Jeff Slobotski and have been semi-gracefully dodging his invites for years. This year I thought I’d come hang out for a day. So here I am.

Last night I went to the VIP pre-opening party. I hung out and talked to some folks and then realized I was hungry. They only food at the party was meaty stuff (other than some creamy artichoke dip) so I went for a walk around the part of downtown Omaha we were at (11th Street-ish) looking for dinner. I found a Mexican place and sat down for a nice quiet meal before the event started. About half way through I was joined by two others – both locals – who are at the conference and recognized me. Both are younger VCs so we had a nice conversation that was hopefully helpful and interesting to them. I learned a little about the scene in Omaha, so that was useful to me. And I enjoy small dinners a lot, so three people was perfect. And the cheese enchilada was exactly what I wanted.

We wandered over to the opening party around 8:30. I was already tired but I figured I’d give it a try. The entryway was subdued and pleasant as people were checking in and getting name badges. They were all a lot younger than me.

We then walked down a long hall and up some stairs into a huge room throbbing with music. Over the next 30 minutes, I said hello to a few folks I recognized, had a few others introduce themselves to me, and noticed that the room had filled up a lot. The music must have gotten louder because I could no longer hear anything anyone was saying to me without leaning over and putting my ear next to their mouth.

At one point I looked around and noticed that I was one of the oldest people in the room. It was 9:30 and I was tired. So I went home, did email for a little while, and went to sleep.

I’m heading out to the conference now and I’m looking forward to it. But I’m very aware of the age shift today for some reason. Interesting …


At dinner on Sunday night I had a short discussion with a long-time friend about the phrases detachment vs. non-attachment. I don’t remember the specific thing that brought it up, but I stated that I was much more interested in non-attachment in how I react to things. We bounced around words a little and then went back to our Mexican food and the broader conversation with the other people at the table.

I’d been playing around with a framework with my therapist for the concept of attachment, especially around stress and anxiety, and trying to figure out a metaphor around it. I had a long discussion on a car ride to Shambhala Mountain Center with Jerry Colonna about it where he helped me clarify some of the edges of my thinking.

Use the universe as the background for the metaphor.

Attachment is like the activity around a black hole. You are constantly fighting against getting sucked into it. All of your energy is focused on not ending up in the black hole.

Detachment is like being in no gravity. You are just drifting. Nothing exerts any force on you in any direction.

Non-attachment is like being in a swirling galaxy. There is stuff going on everywhere. You interact with it. But none of it pulls on you excessively. You are involved and impact some of it but a lot of it is exogenous to you.

There are many situations that arise that cause me to feel like I’m fighting against being sucked into a black hole. I used to react to these situations as they used to cause immense stress or anxiety, which are different but related things for me. While I have gotten much better at this over the years, one of my motivations for starting to meditate was to try to be more mindful, especially around the anxiety (note – Headspace has a great 30 day meditation routine specifically on anxiety.)

Detachment for me is linked to my struggles with depression. When I’m depressed, I’m completely detached. It’s an extremely uncomfortable feeling for me. I’ve very functional, like I am when I’m non-attached, but nothing about it feels good.

While many people suggest that detachment is the right approach to stress and anxiety, and others feel that it’s the path to enlightenment, it doesn’t work in my case. Now, I’m defining the phrase, so for some detachment might be an awesome way to deal with things, but for me it falls in the category of “indifference” and “disengagement” which I apply to things I don’t care about, but doesn’t work for things I am engaged, interested, or involved in.

Non-attachment ends up being the right word (at least in this framework) for what I’m looking for. I realize that some people view non-attachment as a synonym for detachment, but I like the use of the word, and the notion of “actively non-attaching” to things.

When I apply this filter to a stressful or anxiety-producing situation, where I know that I have to engage with it, but am “non-attached” to it, I’ve found a calm focus comes over me. And that calmness can sustain over a long period of time, even in the face of incredible stress. Like putting your head in the mouth of the demon, it makes the black holes disappear for me.


I spent the weekend in Las Vegas with my dad. He’s almost 77 and I’m 49. We had an awesome weekend which I expect he’ll write about in detail on his blog Repairing the Healthcare System in the next few days since he generally does a really nice retrospective of our annual trip together.

As I was reflecting on our weekend during my flight home yesterday, I remembered a discussion I had with Todd Vernon, the CEO of VictorOps, and a long time friend (we’ve been investors in the last three company’s of Todd’s – Raindance, Lijit, and now VictorOps – going back almost 20 years.)

I was at dinner with Todd, his wife Lura the rocket scientist, Amy, and Krista Marks / Brent Milne a few weeks ago. It was just after we’d closed an investment in Krista and Brent’s company WootMath and the six of us were enjoying a meal at the awesome but very loud Blackbelly. Todd and I were at one end of the table and couldn’t really hear the conversation very well without leaning over so we ended up just talking to each other for a little while. That little while turned into a really intense conversation.

Todd made the assertion that something happens to guys between the age of 47 and 50. We started talking about all of our male friends who had gone through various things between 47 and 50, including all the classic mid-life crisis stuff. We reflected back on what each of us had been through in the past few years and where we had ended up. Some was gossipy, some was introspective, and some was piecing together a puzzle to support the assertion.

After a few examples, it came into clear focus for each of us. Todd said a line that has really stuck with me.

“The age of 47 to 50 is optimizing for what you are. Up to that point, we are optimizing for what you are going to be.”

We both acknowledged that we don’t really know much about the psychology of women (well – generally – but especially in this age range), so I’m focused on what happens to men. When I reflect on my own experience over the past few years, I’ve struggled with depression, had a few health scares and had to come to terms with my older body, practiced the concept of detachment, deepened my relationship with each of my parents, built a sustainable relationship rhythm with my brother Daniel, and developed a new level of deepness in my relationship with Amy.

As we went back and forth, we realized that our time in this age bracket is a confluence of a bunch of decisions we’ve made about life. There’s a classical notion of a midlife crisis, but that cheapens the dynamic. A few of our friends have had relationships, especially with their spouse or significant other, blow up while many others have their relationships deepen. We all bought sports cars in our 30s so that cliche doesn’t really hold, and a group of us were divorced in our early 20s. Bizarrely, many of the guys in the gang of divorcees I’m part of all had their first wife cheat on them in their early to mid 20s, so none of us would ever consider cheating on our current wife as the emotional devastation of a busted marriage from your wife’s affair at that stage in life seems to never go away, at least for us. So, as we rolled it around, it wasn’t really a midlife crisis.

But there is acceptance that we are more than halfway through our lives. Our parents are getting older. Some have passed away, others like my dad acknowledge they are likely in the last decade of their life. If you are courageous like my dad is, you can openly talk about mortality and the implications of it. And, as a son, his mortality immediately reminds me of my mortality.

In Bora Bora when Amy and I were together for a month, we discussed mortality a lot. We talked about having “30 good years left in our normative case.” It could be longer, it could be shorter, and it can’t really be planned for.

As Todd and I cycled on this, we came to the notion of “what you are.” In this 47 to 50 segment, we each have spent a lot of time figuring out what we are and optimizing our lives for it. This notion of what we are isn’t static – we’ll keep learning and evolving – but we are no longer striving for “what we are going to be.” Instead of spending time and emotional energy on this, we are spending our time and emotional energy on what matters to us now. What we care about. Who we care about.

My weekend with my dad was profoundly wonderful. He knows what he is, what he likes, and what he cares about. He’s still learning all the time, but he’s not trying to be something he isn’t. He isn’t striving to be something new. He’s just being him.

Todd and I realized at dinner that we are having a lot of fun and getting a lot of satisfaction out of just being ourselves at this stage of life. We’ve each had lots of ups and downs, but we are each married to amazing women, living in a place that we love, surrounded by people who we love, working on things that give us each meaning, and having time to ourselves and with friends that are satisfying. Sure, we each have crappy moments and lousy days, and we each know that at some point the lights will go out, but for now we are focused on being what we are.


I rarely read physical magazines anymore. I only read in the bathroom and most are things I forget to unsubscribe to or that Amy gives me.

Today, I finished the most recent MIT Technology Review where I was reminded about the amazing MIT Science Fiction Society. As a sci-fi nut, I realized I’d screwed up by not having a lifetime membership. So, I’m now trying to figure out where to send my $260 to be a lifer.

As I was reading the other MIT thingy I get regularly (the MIT Science News and Events) I saw a mindblowing stat from the most recent Putnam Competition (the 74th). MIT took four of the top five places, won the team competition, and had 43% of the top 81 scores (depending on the rounding, that’s either 34 of 81 or 35 of 81.) Either way, it’s nuts.

When I was a freshman, I thought I was hot shit at math. I was the star of my high school Mu Alpha Theta team and as a senior had an unexpected first place finish in a Rice University national competition for Algebra. I was pretty damn good in the calculator competitions on my TI-58C. Yes, I was a nerd then, and I’m still a nerd now.

While I got an 800 on the math SAT, I booted all the AP tests except Biology (to place out at MIT you need to get a 5) – I can’t remember what I did the night before the tests but it clearly wasn’t something that I should have been doing if I wanted to pass them.

So, when I got to MIT, I took 18.011, which was the “advanced first calculus course.” It was straightforward. I then took 18.021 (“advanced second calculus course.”) It was less straightforward. If I had placed out on the Math AP test, I would have taken 18.02 and 18.03 instead. So I felt a little less like hot shit.

My friend (and future business partner Dave Jilk) knew I liked math so he encouraged me to take a course called 18.701: Algebra. I figured “Algebra – I’ve got that.” I don’t know if Dave was serious or just fucking with me, but when I got a 12 on my first test I knew I was fucked. I dropped the class shortly thereafter. Dave, of course, got an A in that one. He’s much better at math than I am.

While I ended up being “fair” at math by MIT standards, I developed a weird savant like numeric skill. I can remember crazy amounts of number and data pairs. I can also do a lot of math in my head, although I’m often off by an order of magnitude, which of course either matters a lot or is easy to adjust when you realize it.

Mitchell M. Lee, Zipei Nie, Bobby Shen, and David Yang – y’all are math studs. Well done representing the Beavers in the 2014 Putnam.


Yesterday I wrote a post titled Life Is Messy For Everyone building off of Nick Grossman’s great post Everyone is broken and life is hard.

I was in a nice rhythm after being back four days from my month long sabbatical. I felt completely relaxed, I had an awesome day long offsite with my partners, I was generally caught up with things and was loving being home. I’d scheduled a Monday trip to San Francisco to do something important with one of our portfolio companies and overall felt like I was ready to roll through the rest of the year, including committing to ramping up my running with a goal of doing another marathon in Q115.

The only thing that was bothering me was a sharp pain in my calf. I coincidentally had my annual physical yesterday afternoon. My doctor and I talked about it and she took a look at it. It wasn’t obvious what it was and she decided, after we went back and forth, to have me go to BCH (our local hospital – which is just awesome) and have an ultrasound.

I went over at 4:30pm. They finished at 6:00pm and put me on hold (e.g. wouldn’t let me leave until I talked to my doctor). That made me a little nervous. At 6:30pm I was at the ER in triage for a blood clot in my leg. I was supposed to have dinner with my friend Raj at 6:00pm – he left the restaurant and just came and hung out in the emergency room with me. Amy drove in. By 9:30pm, I had a full regiment of blood thinners, prescriptions, I’d learned to to give myself an injection since I have to do that for a week, and knew what all the risks were in the short term given the size and location of the clot.

I’m doing fine, but it’s yet another reminder that there are many uncontrollable things in life. I’ve got a good attitude about it, everyone in my office was amazingly supportive, Amy and Raj helped me stay mellow, and I learned something new yesterday (how to give myself an injection). Obviously I won’t be ramping up for a marathon (the cycle I’m going to be on is a three to six month one) and I’ve now got something new in the chain of health stuff that happened this year to process.

Even when things are amazing in your life, they are still messy.


Bora BoraI’m back after a one month sabbatical with Amy. We spent the month in Bora Bora, completely disconnected from everything. It is one of the best things I’ve ever done for myself.

At the beginning of 2014, my partners and I had a discussion about ways to sustain the pace of how we’ve been working. We were all tired and were searching for something to try. We decided to each take a one month sabbatical, completely off the grid, during the year. While one person was gone, the other three would cover for him on anything that needed to be taken care of or decided.

Seth went first and went to Europe and studied French with his family. Ryan went next, traveled all over Europe, and won the grand prize in a Lego-building competition. Jason went next, got married, and took a honeymoon for a month in Europe. Amy and I just returned from a month in Bora Bora.

I’ve had a fantasy for a long time about taking a month off. Since 2000, Amy and I take a week off the grid every quarter. It’s been a marriage saver for us. One week – just the two of us – no phone, no email, no work. But we’d never done it for longer than a week.

I’ve also had a fantasy about going to Bora Bora, staying in a hut over the water, and reading a book a day. I don’t know where Bora Bora came from, but the book a day was an easy one for me since I usually read about a half-dozen books on our week of the grid vacations.

I read 45 books since we left on November 7th. Our typical day looked like:

  • wake up
  • run (maybe)
  • eat breakfast
  • read
  • eat lunch
  • read
  • nap
  • lift weights (maybe) or get a massage (maybe)
  • eat dinner
  • read or watch TV

We did 30 days of this. We sprinkled plenty of adult entertainment into the mix, along with lots of long discussions about all kinds of things.

After a week, we were each a little restless. I ate something weird around day five and didn’t feel good for three days. But once we got into the middle of the second week we forgot that the world existed. We woke up each day, did our thing by the turquoise blue ocean, and went to bed at the end of the day.

We headed into week four feeling completely transformed.

I’ve never taken a month off before. During school, I always worked in the summer time. After I sold my first company (on a Friday), I went back to work first thing Monday morning. I’ve been investing ever since and when I stopped working at AmeriData full time, I already had more than a full time job worth of consulting to the startups I’d funded via Intensity Ventures lined up. While doing that, I started working at Softbank/Mobius, and while doing that co-founded Foundry Group.

I find it incomprehensible that I’ve never taken a break like this before. Given my comfort with one week off-the-grid vacations, it was easy to just disconnect and leave everything in my partners’ hands. I trust them completely and having already been through the one month off cycle with each of them earlier in the year, I knew that whenever something came up, good decisions would be made and things would be handled.

As a result, I feel like I’ve completely reset my brain. I read what I wanted – I had over 200 books on my Kindle – so I just picked randomly when I didn’t have “next book” in mind. Some of the business books were skimmers and I only dropped out of one fiction book a quarter way through because I lost interest. The rest was like being transported to the magical reading planet.

Amy and I never grew tired of being together. I could spend all day, every day, with her, all the time. I feel like we’ve mastered being together, but letting there be enough space when one of us needs it that we never get frustrated with each other. Sure, there are moments, but they are very short ones, and usually solved by laughter by one of us.

After 30 days, we are ready to be back. We miss our friends. I miss my partners. We both miss our work, which is something that neither of us has said out loud for a while. And most of all, we miss Brooks the wonder dog!


Kasa SushiI arrived home from Boston last night at 5:30pm and realized I had no plans for dinner. Amy was still in Boston since her Wellesley board meeting doesn’t end until mid-day today so I voxed Seth, Ryan, and Jason to see if any of them were around for dinner. Seth was just landing from Vermont where he had been at Ello for the past few days, Jason was in NY at dinner, and Ryan was already at home having dinner with his family.

I thought about who else I might want to have dinner with, since I rarely eat dinner alone. I love eating dinner with Amy or one other person. Four people is my natural limit – me / Amy / another couple, or a small-ish business dinner. Six is my max – I can handle it – but I always feel at my limit. Once we get over six people at dinner, I end up focusing on the person to the left of me and the person to the right of me and that’s it.

I realized I just wanted to be alone for dinner last night. As I got to downtown Boulder, I pondered where I wanted to eat. The TV show Cheers popped into my head and I realized that the closest place in Boulder I have to Cheers is Kasa Sushi. I adore the owner Mimi and think her husband Mr. Kim is great. I know most of the wait-staff at this point and recognize the sushi chefs. Their specials are unique and outstanding and there is often something off menu for me. When I don’t feel like ordering, they just do Omakase and bring me whatever they feel like.

I wandered into Kasa, gave Mimi a hug, said hello to everyone (they responded with konbanwa), and was ushered to the sushi bar. They know which sake I like so a flask of it showed up. I asked for a few things and the food started coming. I’d brought my Kindle to read, but one of the sushi chef’s was new so we started talking about his first two months in Boulder (he was from New York and was loving Boulder.) The conversation expanded to including everyone around, since I was the only person in the restaurant for the first 20 minutes.

I had a small-ish dinner but big conversations. I felt completely comfortable “dining alone” and was more in the moment during the meal than I often am. I as walked home, I felt lightness in my step, probably some from the sake, but a lot from the conversation at Kasa.

As I walked Brooks the Wonder Dog around Boulder’s Central Park for his nighttime walk, I thought about how I rarely spend my alone time in the context of others but without electronic devices. When I’m truly alone – in the car, on a run, meditating – I’m alone. But when I’m on a plane, on a train, or waiting in a busy place for someone I’m almost always buried in my laptop or my phone as a way to avoid all the humans. But last night, just being alone, with others, where I felt comfortable, with no electronics, was really nice.

Mimi, Mr. Kim, and everyone else at Kasa – thanks for making we feel at home whenever I’m with you. It’s nice to go somewhere for dinner where everyone knows your name.