Brad Feld

Month: February 2021

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.


Amy and I have coffee for about 30 minutes every morning. It’s been one of the wonderful positive side effects of the Covid crisis.

Some days we land on a topic. Other days we don’t. Today, after a few minutes, the question “What is your worldview?” popped up, and we bashed that around for a little while.

The last year has had an enormous impact on my personal worldview. My underlying value system and beliefs haven’t changed, but I’ve reconsidered, rethought, adjusted, and modified many external perspectives. But that’s the easy stuff.

Amy said something this morning that caused me to jump out of my skin with delight.

“You have always been the weird kid in the corner with a big book.”

At the moment she said this, we were discussing how we understood others and how others understood or misunderstood us.

My internal perspective is unchanged, but in the last year, it has surfaced much more clearly. About four years ago, Jerry Colonna and I had a conversation described in his book Reboot: Leadership and the Art of Growing Up where I said, “I’m no longer striving.”

I didn’t completely understand what I meant by this back then, but it was the beginning of me bending the arc on my internal worldview. Jerry linked it to equanimity, which has deep roots in Buddhist thought in addition to its traditional definition.

In Buddhismequanimity (Pali: upekkhā; Sanskrit: upekṣā) is one of the four sublime attitudes and is considered: Neither a thought nor an emotion, it is rather the steady conscious realization of reality’s transience. It is the ground for wisdom and freedom and the protector of compassion and love.

I’ve anchored on the phrase the steady conscious realization of reality’s transience which speaks to me and feels reflective of my current internal worldview.


Amy and I just underwrote one-year memberships to the Boulder Chamber of Commerce for 62 Black-owned businesses in Boulder.

Last summer, Aaron Clark started putting together a list of Black-owned Businesses in Boulder. The current list is at 62.

A few weeks ago, John Tayer at the Boulder Chamber mentioned an initiative he was working on with Aaron to get discounted memberships to all 62 companies. The Boulder Chamber is a long-standing and important part of the Boulder business community, and John has been a great leader for many years.

In an attempt to eliminate any friction associated with a decision for these 62 businesses to join the Boulder Chamber, Amy and I decided to underwrite their memberships for a year. I hope that all 62 will join, and the overall Boulder business community will engage deeply with and support these business owners.

I appreciate Aaron and John’s leadership enormously. I’ve gotten to know and work with Aaron on several initiatives over the past nine months, including participating in an equity learning initiative led by his firm Equity Solutions, supporting Justice Reskill, and experiencing a lot of equity activity Aaron has lead for Energize Colorado.

John recently did one of his Chamber Chats with Aaron. It’s a great overview of some of the work Aaron is doing, along with a discussion of Black History Month.

If you’d like an intro to Aaron or John, just email me.


The only time I go outside right now is to go running. I had an awesome run in the dark at 5:30am today in 10 degrees. There were only two cars that passed me and one person near the end of my run walking his dog.

As Amy and I sit in our office in Aspen and grind away, we are blessed with a magical view.

A few moments ago, my EA Annie sent me a link to WindowSwap. It’s a treasure. I felt like hanging out in Ukraine for a bit, so off I went.

Each video is 10 minutes long with sounds, so on a big monitor, it feels pretty close to looking out the window.


Finding Meaning

Feb 19, 2021
Category Personal

A few minutes ago, Amy sent me this to ponder as we head into the weekend after an intense week.

Find meaning. Distinguish melancholy from sadness. Go out for a walk. It doesn’t have to be a romantic walk in the park, spring at its most spectacular moment, flowers and smells and outstanding poetical imagery smoothly transferring you into another world. It doesn’t have to be a walk during which you’ll have multiple life epiphanies and discover meanings no other brain ever managed to encounter. Do not be afraid of spending quality time by yourself. Find meaning or don’t find meaning but “steal” some time and give it freely and exclusively to your own self. Opt for privacy and solitude. That doesn’t make you antisocial or cause you to reject the rest of the world. But you need to breathe. And you need to be.

 – Albert Camus
Notebooks, 1951-1959

I’ve been spending a lot of time with Nietzsche lately. I expect I’ll be adding some Camus to my diet.


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.


We are running the Venture Deals Online Course from March 7, 2021 – April 30, 2021.

We’ve moved the Venture Deals Community from Slack to Mighty Networks where we have much more functionality and flexibility.

Once again, we’ll do a weekly AMA with a variety of people participating.

For now, registration is open. Please sign up if you want to take the Spring 2021 Venture Deals Online Course.


I used to love the Matrix’s Red Pill / Blue Pill metaphor and still use it occasionally to try to make a point around dealing with reality in an entrepreneurial context. Several years ago, I became deeply bummed out about how this metaphor was being used in politics and gender equity situations. It’s gotten worse since then, and I find many of the cases it is used in and the people who use it reprehensible, so I don’t use it much anymore.

However, I used it today for a company that is doing well and has exceptional strengths and some fundamental weaknesses.

This is true of every company that is doing well.

But it’s hard to deal with reality all the time. When things are going well, leaders (and boards) often avoid dealing with weaknesses. Some board members and investors are great at motivating a CEO to level things up. Others aren’t. Some CEOs want to embrace the challenge of leveling up in areas where they, and the business, are fundamentally weak, even if it’s emotionally and functionally challenging. Others don’t, or their own behavior and wiring get in their way.

There are many points in a company’s life where the CEO and the board can either deal with or deny reality. When dealing with reality, a key factor is embracing the business, team, and individual’s weaknesses and then deciding how to address them. Collectively. With empathy and emotional support for each other.

This isn’t easy. Over the past 30 years, I’ve been in this position many times, often multiple times as a board member in a particular company. These are different than crisis moments, where everything is on the line. It’s often when many things are going well, but there are prominent areas of the business that aren’t keeping up with what’s working.

I’ve never figured out magic words to say as a board member in these moments. Instead, I say what is on my mind, take responsibility for my participation in any weaknesses, dysfunction, or challenges, and focus on where I think we need to put additional energy in improving the business.

This is often an acknowledgment that we need to add a few experienced people to the leadership team. The CEO has to drive this. When the right people are added, notable positive shifts in the weaknesses can happen extremely quickly. But, in the absence of them, the talk generally continues, without action. Reality is not dealt with – just poked around the edges.

One of an effective board’s roles is to speak clearly about the weaknesses and hold the CEO accountable for addressing them. When I am effective as a board member, I do this well. When I’m not, I don’t. I’ve got plenty of cases of both in the last 30 years.

My mantra as a board member is:

“As long as I support the CEO I work for her. If I don’t support her, my job is to do something about that, which is not to replace her, but to try to get back to the place where I support her.”

Ultimately, as a board member and major investor, I can participate in replacing the CEO. While I’d prefer not to do that, I’m not afraid of doing it. But dealing with reality with the existing CEO is much more enjoyable and has generally been a more successful path for me.

All of this is extremely challenging, as it has to do with personal growth in the context of business growth. It’s easier to have entrenched thinking, play out the exact historical patterns that worked or be resistant to addressing whatever the current reality is. It’s compounded by the fact that exogenous factors are constantly changing and often change extremely fast.

The probability of long term success increases with a CEO, a board, and a leadership team is tuned into whatever the current reality is, their strengths and weaknesses, and focus on continually leveling up the weaknesses while continuing to play to their strengths.

If you are a CEO, spend a few minutes today contemplating whether your board is highly effective at helping you grow, scale, and evolve the business. Are you systematically and continuously addressing your weaknesses as an individual, leadership team, and company?

Are you dealing with reality?


On my run yesterday, I listened to Tim Ferriss interview Naval Ravikant on Happiness, Reducing Anxiety, Crypto Stablecoins, and Crypto Strategy.

I know both Tim and Naval. I have a mostly virtual relationship with each of them (I think I’ve been in the same physical space with Tim twice and never with Naval), but they are two people I’ve learned a lot from over the past decade.

When I run, I listen to one of four things.

  • Nothing
  • Podcasts
  • Audible Books (mostly science fiction)
  • Music, but generally my long time standards (Pink Floyd, Boston, Red Hot Chili Peppers, Rush)

I go through phases, and I’m in a Podcast / Audible phase. I’m a little bored of Diamond Age (I’m halfway through in a slow spot), so I fired up a random Tim Ferriss podcast. I noticed he’d done one recently with Naval, so that was it.

The crypto stuff was good, but I was much more intrigued by everything else. I’m a big fan of Richard Feynman, so when Naval started rolling out Feynman quotes, he had me. There was a ton of wonderful in the back and forth between Tim and Naval, and when Naval got on a roll on a topic, the running just vanished into the background.

A fun sleeper idea in the middle of things was that Naval, who has over a million followers, doesn’t follow anyone on Twitter. I only use Twitter to broadcast things these days, so I think I’ll try that hack for a while and see if it works.

I haven’t been blogging much lately – on purpose. I’ve been trying to reset a few things in my writing and decided to go inward for a few months, starting around my birthday. I believe the reset has happened and listening to Naval and Tim helped reinforce a few things I’ve been playing around with now that I’m 55 years old.

Tim / Naval – thanks. I enjoyed listening to y’all.