Brad Feld

Category: Books

Book: Wintering

Apr 16, 2021
Category Books

I listened to Wintering: The Power of Rest and Retreat in Difficult Times on Audible over the past week. It was spectacular.

Danielle Morrill recommended it to me. We had an intense up and down journey together with Mattermark, which was doing great until we made a fundamentally bad decision around the company’s strategic direction. The ride down, especially against the backdrop of what I expect would have been a success if we hadn’t made that strategic decision, was extremely challenging. We both learned from it, and it’s been awesome to see the journey that Danielle has been on since.

While I often run without listening to anything, I’ll occasionally listen to a book on Audible on long runs. I started Wintering last week during a run at Hall Ranch. I did another run at Hall Ranch the next day and listened to some more. I run a long loop from my house around McIntosh Lake in the dark and almost finished it two nights ago. Yesterday, I did a few miles in a classic Boulder spring snowstorm at the end of the day and finished it up.

Danielle recommended that I listen to it rather than read it, which turned out to be a great recommendation. The narrator (Rebecca Lee) was incredible. There was so much emotional impact and resonance that I thought it was the author (Katherine May) for a while until I looked it up.

Our entire species has been wintering since the Covid crisis hit. We are just starting to emerge from a literal winter, although the four inches of snow that fell at my house yesterday one of the last gasps of winter trying to hold on. Of course, whether we want to or not, personal winters often appear out of nowhere, even in the summertime.

There’s a paragraph from an NPR interview that sums up whatever review of the book I could write.

Wintering is refreshingly free of self-pitying navel-gazing and trite exhortations to buck up. In fact, May complains about a culture in which we are “endlessly cheerleading ourselves into positivity while erasing the dirty underside of real life…The subtext of these messages is clear: Misery is not an option.” Although she agrees that “Happiness is the greatest skill we’ll ever learn,” she insists that it’s also important to learn about sadness. What she calls wintering is “the active acceptance of sadness.”

I love the phrase “the active acceptance of sadness.” It’s a thing. It’s part of life. I can be for an hour or years. Passively accepting it or actively denying it makes it worse. Actively accepting it is profound.


I sort of took a Q1 Vacation last week.

2021 didn’t really feel like it started for me until January 21st. Yeah, I took a company public on January 4th, but then January 6th happened. It was a cold, dark, and anxious stretch where January felt like it had about 51 days in it. Then I was deep in SPACland and lots of deals and financings. I definitely had some “I just need to get to March 26th, and then I get a break” in my head.

We got back to Boulder on a Friday, settled into our house on Saturday, and I sort of kind of tried to disconnect (but failed) on Sunday. Monday, I had a full day of work, and a couple of things had landed on Wednesday, so I decided “fuck it” and just worked Monday, Tuesday, and Wednesday before going dark from Thursday to Sunday.

It is delicious to be back in Boulder. The weather is perfect, the birds are singing, and our meadowlark is back in our meadow, chirping away. We missed Cooper (we don’t take him to Aspen), so it has been a fun adjustment to get used to him again (and for him to get used to us.)

I had a monster week of running – mostly on trails. 65 miles with almost 4,300 ft of elevation. That’s the most I’ve done in a long time, and my body absorbed it pretty well.

When I wasn’t running, napping, or eating, I read. A lot. And there are some themes in what I’ve been reading.

Lighten Up!: A Complete Handbook for Light and Ultralight Backpacking: I knew of ultralight backpacking (and have heard the phrase a bunch recently in marketing stuff), but I didn’t really know the parameters or the style. This was a great intro.

Allen & Mike’s Really Cool Backpackin’ Book: Traveling & camping skills for a wilderness environment: Recommended by the previous book. Some new stuff, some repetition. Some ultralight. Some normal backpacking.

Ultralight Backpackin’ Tips: 153 Amazing & Inexpensive Tips for Extremely Lightweight Camping: Again recommended by the first book. I fell into the Kindle content market trap and clicked on links. Mostly repetitive, but good reinforcement on a few things.

Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century: Jeff Lawson and Twilio are awesome. This book is phenomenal, both as the story of Twilio with the underpinning of Jeff’s management philosophy. If you ever use the Marc Andreessen phrase “software is eating the world,” but you haven’t read this book, go read it to understand what the phrase really means. I’m going to host Jeff for two book events: one with Techstars and one with our portfolio. Yes, every entrepreneur and would-be entrepreneur should read this book.

Guantánamo Diary: Now published as The Mauritanian. Amy and I watched the movie a few weeks ago in Aspen when it came out. It was powerful. The book was even more powerful. I wish Guantanamo never existed – it’s a massive negative on American values. I wish Obama had followed through on closing it down. I hope Biden closes it down. If you disagree with me, read the book.

Lost in Startuplandia: Wayfinding for the Weary Entrepreneur: I recently did a talk for a class Ted Zoller teaches at UNC, and he recommended this book. I had it on my Kindle but had never read it. It was a fun memoir-like story of Keller Fitzsimmons’ entrepreneurial journey. Having read hundreds of these by men, I always learn a lot more now when I read one by a woman. It’s excellent.

Living with a SEAL: 31 Days Training with the Toughest Man on the Planet: Another one that had been lingering on my Kindle since 2017. Another recommendation. Hilarious, awesome, fun, and inspiring. I guessed that Seal was David Goggins pretty early on based on what I knew of Goggins. But I had no idea who Jesse Itzler was (now I do.) So, the next book I read was …

Can’t Hurt Me: Master Your Mind and Defy the Odds: Goggins is an epic specimen of a human. But I didn’t really know his story beyond his ultrarunning. It’s an incredible story at many levels. It’s not as fun as Itzler’s book but still awesome and much more inspiring. And it led me to read Itzler’s other book …

Living with the Monks: What Turning Off My Phone Taught Me about Happiness, Gratitude, and Focus: Still funny (Itzler is hilarious and writes well about his own hilarity), somewhat inspiring, but lots of fun. Not as powerful as Living with a SEAL, but now I know Itzler even better.

The Stone Sky (The Broken Earth Book 3): I listened to N.K. Jemisin’s Broken Earth trilogy on Audible while I’ve been running. This series deserves its own blog post and will get that at some point. I think Jemisin may have moved to the top of my contemporary sci-fi writer list. I realized all I was reading were books by white men, so I found a few non-white women sci-fi writers. Jemisin is a world builder at the level of William Gibson and Neal Stephenson and may even be better than them at this point. It was an incredible series.

Not All Fairy Tales Have Happy Endings: The rise and fall of Sierra On-Line: I still remember playing Mystery House on my Apple ][ and being blown away. I spent hours and hours playing Ultima. I felt naughty when I bought Softporn as a teenager, even though the game wasn’t really porn (or even very salacious.) I didn’t know Roberta and Ken Williams, but as an early Apple ][ aficionado, I bought or pirated everything Sierra On-Line did when I was a teenager. And played them all. Choplifter and Olympic Decathlon got more playtime, but Sierra On-Line had a special place in my heart. I loved this book – Ken Williams doesn’t pull any punches anywhere about Sierra On-Line’s rise and fall. It’s a great entrepreneurial software tale from the 1980s and 1990s.

Too Old to Ultra: When a marathon is just not enough: A quick jolt of inspiration from a bunch of storytelling and some advice from a serious ultrarunner who is older than me.

I wish I’d really taken the beginning of last week off. I feel fresher, but after a very busy Q1, I didn’t get the full vacation I needed. Oh well – such is life. At least it’s springtime.


Generation X: Tales for an Accelerated Culture is weekend reading for anyone who wants to understand me and my generation.

I was born in 1965 – right at the beginning of the transition from “Boomers” to “Xers.” I’m glad my parents had me in 1965 instead of 1964, where I’d spend my life arguing (maybe with myself) that I’m not a boomer.

A millennial friend of mine didn’t know anything about Generation X, so I sent her a copy of the book. I suppose I was teasing her too much about being a millennial, which was just me mostly being a typical ironic Gen X slacker.

I reread Generation X a few weeks ago, and it held up. The definitions in the margins made me flash back to phrases we used in my early 20s. Douglas Copeland’s brilliant imagination shines throughout. And, at 55, I’ve become comfortable saying “Kids today …” which is what I’m sure my parents (and the boomers) said about me and my generation.

This week sucked emotionally. The Boulder shooting on Monday took the wind completely out of Amy and me. It’s Friday, and I’m winding down for the weekend. Work was intense, so I didn’t have a lot of time to feel my feelings. We were in the car for a while this morning driving back to Boulder from Aspen, so I let myself settle into how I felt. Now that I’m not shocked anymore, the best word I can come up with is “sad.” Very sad.

Grunge is my music. Pessimism abounds in Gen Xers. I’ve adopted the mantle of “paranoid optimist,” which I first heard from Madeleine Albright. At 55, I prefer to be happy and optimistic, but underneath it all is cynicism.

I’m glad to be back in Boulder.


Today’s book recommendation, for anyone interested in venture capital, is The Business of Venture Capital: The Art of Raising a Fund, Structuring Investments, Portfolio Management, and Exits by Mahendra Ramsinghani.

A decade ago, I got a cold email from Mahendra. He was investing in Detroit and eager to write a book about the art and science of venture capital. At the time, Jason and I were just finishing up the 1st edition of Venture Deals: Be Smarter Than Your Lawyer And Venture Capitalist and I was enthusiastic about helping anyone else working on a book that demystified venture capital investing.

I immediately introduced Mahendra to a bunch of Foundry Group LPs, partners, and entrepreneurs. He made progress quickly, and I fondly remember the first edition with the green cover.

Mahendra and I kept in touch. During a book tour for the 1st Edition of Venture Deals, Jason and I visited the University of Michigan. Mahendra cornered me in a hallway and pitched the idea of doing a book together around how a board of directors works at a startup. A few months later, we started working on it.

Startup Boards: Getting the Most Out of Your Board of Directors was released in 2014. Soon thereafter, Mahendra started to work on the second edition of the Business of Venture Capital. Given our recent collaboration, he asked me to write the foreword for the second edition, which was an easy yes for me. The 2nd edition had a blue sky cover and was also released in 2014. In the foreword, I wrote that “VC is a business where each investment teaches you something new – the book provides only a basic framework but each one has the ability to carve a different path in this universe.”

Mahendra recently came out with the 3rd edition of The Business of Venture Capital: The Art of Raising a Fund, Structuring Investments, Portfolio Management, and Exits. It’s now 500 pages and includes much-needed frameworks for culture, diversity, and values that are timely topics when we look at the challenges we have seen in venture capital around gender, race, diversity, and sexual abuse. This time the foreword is from Scott Kapor of A16Z who in 2019 wrote an excellent book on venture capital titled Secrets of Sand Hill Road: Venture Capital and How to Get It.

 

If you have suggestions for the fourth edition, please reach Mahendra at mr “at’ secureoctane.com.


After my blog post Book: The Soul of an Octopus I received a flurry of emails telling me I needed to watch the movie My Octopus Teacher on Netflix.

I watched it last night and it was beautiful.

I’m fascinated by which blog posts generate email responses. Sometimes is zero. Sometimes it is a lot. This one was a lot.

Octopuses are crazy interesting. And Craig Foster is pretty awesome.

Thanks everyone for the email with the recommendation.


My favorite animal is a polar bear.

For some reason, I have always related to polar bears. When I’m reincarnated, I hope I come back as a polar bear.

I’ve always like octopuses but never thought much about why. After reading Sy Montgomery’s incredible book The Soul of an Octopus: A Surprising Exploration Into the Wonder of Consciousness, I now know why. It’s simple – we don’t understand how they think.

While a quick throwaway thought is, “Brad, we don’t really know how animals think” or some other assertion around that, there’s such an enormous gap between this question when applied to a dog versus an octopus. This lives in Sy’s subtitle: “A Surprising Exploration Into the Wonder of Consciousness.”

I read the book over a week and had several incredibly complicated dreams, especially around processing stimuli. I had magic superpowers in my hands, arms, legs, and feet in one of them. I remember waking up thinking, “that would be so cool.” And then the dream slipped away.

One of my favorite movies of the last decade is Arrival. We’ve watched it a few times, and I think I’ll watch it again.

Time and language play key roles in the film. As humans, we have a very linear view of time and a constrained view of language. Sci-fi plays with time a lot, and Arrival plays with both time and language.

That leads me back to octopuses. Humans often anthropomorphize everything, where we apply our concept of time and language to other species. As I read The Soul of an Octopus, I kept flashing back to Arrival. The book itself is linear through time, but the octopuses in the book don’t feel like they are necessarily operating in a time-linear fashion. The protagonist (the author Sy) hints at this but doesn’t fully embrace it. I wonder what she would have written differently if she approached the experiences she had with octopuses as ones where the octopuses weren’t experiencing things in a time-linear fashion.

Sy embraced the difference in language processing more fully. The octopus brain has around 500 million neurons (similar to a dog) – the most of any invertebrate. However, two-thirds are in their arms. The eight arms appear to process information independently of each other, resulting in octopuses being incredible multi-taskers. Their non-verbal communication has many levels, and they seem to be taking input simultaneously in multiple dimensions.

Combining this with non-linear time is fascinating to me. Other than sci-fi, the only other non-linear time entity I consciously engage with is a computer. It also uses a different approach to language.

And then the rabbit hole gets deep, twisty, and really fun.

Octopuses are now my second favorite animal.


I haven’t been posting about my reading lately. While I continue to read at my typical pace, I think I was a little tired of writing book reports, but that has passed.

Last night I read The 80/80 Marriage: A New Model for a Happier, Stronger Relationship. Kaley and Nate Klemp have written an excellent book that can help any married couple improve their relationship. This is especially true in the time of Covid, given all the additional dynamics about being home together most of the time.

When Amy and I wrote Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur in 2013, our goal was to write something different than YARB (“yet another relationship book”). Whenever I worked on it, I had in my mind, “Do not let this be a YARB.”

The 80/80 Marriage is definitely NOT a YARB. The framework comes from the idea that many marriages are 80/20 with a goal of shifting to 50/50, where the partners are equal in the relationship. Kaley and Nate’s goal is to do better than 50/50, hence 80/80.

Amy and I have had an equal partnership in our marriage from the beginning. However, as any married couple knows, that ebbs and flows and at times doesn’t feel equal. The two of us talk about it often, and when we get out of balance on any dimension, we both own what is going on, discuss what we need to do to get back in balance, and then move forward.

Once you start deconstructing this, many traditional relationship tools fit nicely in the 80/80 Marriage construct. Amy and I are big fans of the Five Love Languages. I like receiving acts of service, she likes receiving praise, and both of our #1 is quality time. We also like giving what we like receiving, and fortunately, we both like receiving acts of service and being together all the time.

But what if instead of each person being at 50% of the relationship, the goal was to exceed expectations? That’s where the 80% comes from. An example would be from this morning. Amy is a huge knitter and has been wrestling with a giant yarn tangle. Rather than throw it away, she spent some time last night unsuccessfully trying to untangle it. Today, while she was on a board call and I was upstairs, I spend 10 minutes and untangled it. When she came upstairs, she was delighted with the minor act of service that she didn’t ask for.

There are hundreds of things like this we do for each other each month. Some are significant. Some are trivial. But they are all unexpected and unrequested. That’s what pushes the 50% up to 80%.

Kaley and Nate cover all aspects of a relationship, including roles, priorities, boundaries, power, and sex. And, they finish with the 5 essential habits of the 80/80 marriage:

  1. Create Space for Connection
  2. The Call-and-Response of Radical Generosity
  3. Reveal Issues, Misunderstandings, and Resentments as They Arise
  4. The Shared-Success Check-in
  5. Create Space from Digital Distractions

This felt great to me, as Amy and I have regular approaches for each of these. Our Qx vacation approach is highlighted in the book as an example of #1. My yarn story above is an example of #2. Our Life Dinner is how we practice #3, although we do it in real-time also. Morning coffee and Life Dinner is #4, along with shared meals (typically lunch in the time of Covid.) And our Qx vacations and Digital Sabbaths are #5. Of course, what we do is more than just labeling the activity, but if you read our book or follow along on this blog, you can probably related to some of the examples I’ve given in the past.

Kaley and Nate Klemp have made a significant contribution with The 80/80 Marriage: A New Model for a Happier, Stronger Relationship and written something that is not-YARG.


I love Neal Stephenson. I’ve read all of his books, some of them multiple times. Well, except the Baroque Cycle trilogy, which I’m saving for a special period of time to get lost in them, and from everything.

Last week I read In the Beginning…Was the Command Line. For the second time. This time I read it on my Kindle, which was fitting.

Stephenson wrote it in 1999. As we exit 2020, it’s a great reminder of the place technology was around 20 years ago. It shows how much has changed and how little has changed.

As a continual user of a wide variety of technology, I think our modern computing infrastructure is completely fubared. As we try harder and harder to make the thing we interact with as users better, the complexity increases. Some things work beautifully, while others are a complete débâcle.

After finishing In the Beginning, I decided to clean up my TV setup. I’ve got DIRECTV, Roku, and an Apple TV. I use Savant to control it. I paid a lot of money to have someone set it all up. All I really wanted to do was log in to HBO Max so I would watch WW84, which turns out to be completely not worth it, even if all I needed to do was press a button to watch it.

Ready Player One? Yup – it felt like that. Phone in one hand. Savant remote in another. Apple TV settings. I tried resetting my password a few times. 15 minutes later, I realized that I probably had the wrong username for DIRECTV. I tried a different username. Then it got really messy since Apple TV thought I was one username, and now DIRECTV thought I was another. I finally figured this out after going over to Roku and setting things up there.

Then I decided to try to go clean up all the random tiles on Roku. Of course, I’ve lost track of my Roku controller, so I did this using Savant. But my Savant controller doesn’t have an * programmed into the Roku control section, so I had to do it app by app. I made a document with all the Channels I wanted to delete. I started manually deleting them by Search Channels one by one. Some of them didn’t appear, so they were apparently undeletable, at least until I find an asterisk.

An hour later, I was ready to watch WW84. We watched it last night. It was awful. We then realized we had watched end of the world movies four nights in a row (Tenet, Greenland, Midnight Sky, and WW84). WTF. What’s the point of that anyway.

I’m spending a lot more time at the command line these days. I’ve been learning Clojure, using Zsh and Emacs, struggling with Homebrew, and trying not to be annoyed with GitHub. And my new favorite app is Roam, which is not really a command-line app but sometimes feels like it.

I know when I get back to Aspen, where there currently is no heat due to what appears to be a natural gas line sabotage where I have Xfinity instead of DIRECTV, my Roku settings won’t have synchronized. Maybe AppleTV will, maybe it won’t. At least my Kindle will be the same. That’s because I only have one Kindle.

I haven’t even started to push anything into production.

Nothing is going to look anything like this 20 years from now.


Amy and I watched Tenet the other night. When we finished, she turned to me and said, “That was one big, hot mess of a movie.” I sat for a moment and said, “I’m not sure it was any good, but I’m not sure.”

I just watched the trailer. While these are clips from the movie, there’s no correlation in these clips to anything that gives you a feeling for the movie—more hot mess.

Temporal dynamics are a common trope in movies. While it’s a clichéd part of the sci-fi genre, it is becoming more common in contemporary good vs. evil save the world action movies.

After sitting for a moment, I flashed back to another movie, Interstellar, another hot mess but one that I enjoyed a lot more.

After a little exploration, I realized Christopher Nolan directed them both. As I looked through his filmography, the theme of time was woven throughout.

I’ve seen most of these movies. Memento is my favorite. Interstellar, now that I’ve watched it a few times, comes in second.

https://youtu.be/HDWylEQSwFo

As I read Matthew McConaughey Greenlights last night (excellent, well worth reading), I felt that exploring temporal reality, a core tenet of Tenet, was worth spending more time with, which means I’ll watch Tenet again.