Brad Feld

Tag: jerry colonna

Jerry Colonna spent a few hours with me and Amy on Saturday at our house. Jerry is one of our closest friends on this planet so any time we get time with him is a treasure for us. It was a cold-ish, snowy, gloomy Colorado early winter day. Amy and I were pretty off-balance due to my blood clot so it was especially nice to be with him as he always helps rebalance us.

We talked some about his new company Reboot. I’m a huge supporter of Jerry’s work – recommending many of the CEOs we work with to him, or his associates, for coaching. I attended a recent CEO Bootcamp as a special guest and it was amazing – I recommend it to every CEO.

Jerry mentioned that the recent Reboot podcasts were doing great and really fun. I noticed this morning that the podcast he did with Rand Fishkin, another close friend, titled #7 Depression and Entrepreneurship – With Jerry Colonna and Rand Fishkin, came out today. So I read the transcript (I can read a lot faster than I can list) and thought it was dynamite.

As usual, Jerry goes deep and intimate – very quickly. So does Rand – total, extreme, full transparency. Enjoy!


I was with my close friend Jerry Colonna for dinner last week. We sat outside at the Boulder Teahouse, our favorite place to eat together, and shared a meal, some heavy conversation, and some love.

I love Jerry. I learn something every time I’m with him. He’s one of the first VCs I ever worked with and is my favorite other than my Foundry Group partners. We both struggled openly with depression. I think we have helped each other, and many others, through our openness. I consider him one of my closest friends.

We talked about a couple of heavy, conflict filled situations we were each involved in. He said something profound to me that I’ve been carrying around since we had dinner.

To be adult in a relationship is not to be conflict free. It is to resolve conflicts mindfully.

– David Richo – How to Be an Adult: A Handbook on Psychological And Spiritual Integration

Most of the conflicts in my life are in business. Sure – Amy and I have them occasionally, but I grew up in a pretty conflict free home. My parents disagreed on things but talked through them. When I disagreed with my parents, they listened to me and we tried to work things out. Sometimes I ended up being disappointed or unhappy in the moment, but they taught me to move on to the next thing.

My first marriage has lots of conflict in it, which I’d put it in the passive aggressive category. I think that’s why I find passive aggressive behavior so distasteful – it reminds me of the failure of my first marriage. Of course, we are surrounded by this throughout of lives, even when people have the best of intensions, so I try to bash through it when I see it happening, turning passive aggressive dynamics to conflict, which has to get resolved.

In business, I’ve worked with a wide range of people. I’ve experienced the full spectrum of conflict many different times. When I see conflict emerging, I try to confront it directly, calmly, and thoughtfully. “Mindfully.” I rarely lose my temper. I try to listen carefully. I try to incorporate a wide view of what is going on, rather than just jump into a particular position. I try express my position clearly without excess emotion. I listen and incorporate more feedback. When the conflict is intense, I put myself in the position of driving a resolution, especially in ever-present sub-optimal situations where the “perfect” answer is elusive.

I really love the notion of mindfulness. Wikipedia’s buddhist definition is the one I understand the best.

Mindfulness is “the intentional, accepting and non-judgmental focus of one’s attention on the emotions, thoughts and sensations occurring in the present moment”, which can be trained by meditational practices

My experience this year with meditation has surrounded me with this word. At least half of the stuff I’ve been reading on meditation talked more about mindfulness than meditation. The practice I’m getting from Headspace is opening up a whole new dimension for me of how to think about work, life, and relationships. And when Amy says, “Brad – be present” she is reminding me to be my best, mindful self.

I don’t enjoy conflict, nor do I seek it out, but I’ve never been afraid of it. I just confront it and deal with it the best I can. And now I have a word for how I do it, which is “mindfully.”


I saw a great job title this morning when I was looking someone up on LinkedIn. It was “CTO Whisperer.”

As I’m getting deeper into meditation. I hear the word “teacher” a lot. I’d never thought much about it before, but it’s used in a similar way to how we use the word “mentor” at Techstars. When we started to use the word mentor in 2007, it required defining. Now mentor is getting overused by the broad entrepreneurial landscape. I have no idea whether teacher is overused as well, but the parallel got me thinking about the idea of a CEO Whisperer.

I’ve always been fascinated by the idea of The Horse Whisperer or a Dog Whisperer. A person who has a special, magic skill that certain animals respond to. A unique ability to calm and teach. A style about them that is unique, loving, and kind, even in difficult circumstances.

As I was mulling this over, my friend Jerry Colonna popped into my mind. While Jerry is referred to as a CEO coach, he most certainly is a CEO Whisperer. And for those who don’t know Jerry’s past, he was an extremely successful venture capitalist, founding Flatiron Partners with Fred Wilson in the mid-1990s before retiring from venture capital in the early 2000’s.

I count Jerry as a very close friend. As a mentor. As a teacher. And, with all great mentor / teacher relationships, we learn from each other. Which led me back to the idea of a CEO Whisperer.

In the 1990’s, Jerry and I worked together on several investments and were on a few boards together. Our styles were very complementary – we both had a soft touch and were supportive of the CEO, but had different things we could help with. I know that my involvement on these boards deeply shaped my role and approach as a board member and investor, as I thought Jerry was the best board member I’d ever worked with at that point in time.

I’ve met – and worked with – a few other people who I’d consider CEO Whisperers, but none compare to Jerry. And when I think about how I want to be viewed by the CEOs I work with, the idea of mentor and teacher immediately comes to the forefront of my mind.

The world of entrepreneurship needs more CEO Whisperers. Thanks Jerry for leading the way. On multiple fronts.


It’s really hard to be a CEO. Becoming a great CEO takes a lot of time, work, focus, coaching, and introspection.

My very close friend Jerry Colonna is hosting his second CEO Bootcamp from April 2 – April 6. Several CEOs from the Foundry Group portfolio went last year and each had an amazing time. This year I’m going to be attending as a special guest and participating throughout the four day program.

I’ve learned an enormous about from Jerry over the past 20 years.  We first met in 1994 when I was a chairman of NetGenesis. Jerry had recently invested in a company called eShare, which ended up buying a product called net.Thread (one of the first, if not the first, threaded discussion group system – which was written in Perl) from NetGenesis. I joined the eShare board as part of the deal and a very deep friendship and working relationship ensued.

When Jerry told me about the first CEO Bootcamp a year ago I encouraged a number of CEOs in our portfolio to attend. Each one came back saying some version of “it changed my life”, which wasn’t really a surprise to me knowing Jerry but was a strong positive affirmation of the experience.

This year, when Jerry told me the dates for CEO Bootcamp and asked me to spread the word, I asked if I could come and participate. It’s in Colorado at an awesome place called Devil’s Thumb Ranch so I can drive to it and is a topic that’s front of mind for me given my relationship with the various CEOs in our portfolio.

I try hard to develop a deep personal relationship with the CEOs I work with. I’ve written in the past about Being Vulnerable and think it’s one of the most important qualities of a leader. As Jerry says so well in the overview of the requirements for attendees, “you may be tired, but you must be vulnerable, curious and courageous.” The full list of requirements follows:

  • You’re the CEO of a tech start­up that has employees.
  • This is the first time you have been a CEO within a company of this scale.
  • You’ve logged immeasurable hours and have made tremendous sacrifices.
  • You’ve had success with your company. You realize there is more to this game than “success.”
  • You may be tired, but you must be vulnerable, curious and courageous.

I’m planning on participating in the entire event. The agenda is still being finalized, but the current plan is for me to do a joint talk with Jerry on Friday, fireside chats with Jerry on Friday and Saturday, and hikes after the main sessions.

I know two of Jerry’s three partners in this endeavor and think Sam Elmore and Ali Schultz are dynamite. To be clear, I’m volunteering my time and participating – this is Jerry, Sam, Ali, and Michael’s gig so I’m going to do whatever they want me to – or not to – do.

Registration is open until 2/9/14 at midnight MST. 20 CEOs will be accepted. I hope to see you there.


We’re just under one month until Defrag, and if you’re a startup founder, a VC, and IT exec, or anyone that wants to have their brain stretched, I hope you’ll join me in being there.

The agenda is now about 90% complete (check the google doc for real-time updates) and Eric tells me that he’ll be finalizing everything in the next week or so.

For those of you who attended two years ago, you may remember my “Resistance is Inevitable” talk about the rise of the machines. This year, I’ll be leading two different sessions.

First, Jerry Colonna and I will be having a discussion about the emotional challenges of entrepreneurship. I’ve written about Jerry many times on my blog. He’s a huge resource to entrepreneurs, a great mentor and confidant of mine, and I’m looking forward to a public conversation about some topics near and dear to both of us.

Second, I’ll be having a conversation with Boris Sofman of Anki. Hopefully he’ll bring some toys for us to play with.

For a taste of some of the other topics, ponder:

  • The Rise of the Citizen Explorer (which about the happenings at OpenROV)
  • The History and Future of Calm Technology
  • One Billion per Second: The Rise of Designer Data Architectures
  • Lighting up the world with sensors: using data to effect change

Add in great WiFi, amazing people, an intimate and welcoming atmosphere, and three days of impact-filled ideas, and you’ll quickly find out why Defrag is one of my favorite events of the year.

If you register before Friday, the code “brad15” will take 15% off of your registration.

See you there!


A classical relationship problem is the dichotomy between solving a problem and providing empathy. If you really want to understand this, spend two minutes and watch the awesome “It’s Not About The Nail” video below.

Amy and I have figured this out extremely well in our relationship. We talk about it in Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur using the example of the scene from the movie White Men Can’t Jump to frame the situation.

There’s a delightful scene in the movie White Men Can’t Jump. In it, Billy Hoyle (played by Woody Harrelson) and Gloria Clemente (played by Rosie Perez) are in bed together. Gloria says to Billy, “Honey, I’m thirsty.” Billy gets up without saying word, goes to the kitchen, fills up a glass of water, brings it back to the bed, and gives it to Gloria. As Billy is crawling back into bed, Gloria tosses the water in his face. Startled, Billy says, “What?!” A long conversation ensues, which can be summarized as, “Honey, when I say I’m thirsty, I don’t want a glass of water. I want empathy. I want you to say, ‘I know what it’s like to be thirsty.’”

But this isn’t limited to personal relationships, or the difference between men and women (lots of men need empathy, even if they don’t know how to ask for it.) I see this all the time in my interaction with entrepreneurs and CEOs. I see it in the board room. And I see it in the way a CEO works with her leadership team.

The natural reaction in many of these cases is to immediately jump in and solve the problem. Granted, this is male-centric, as the ratio of men to women in these meetings at startups and entrepreneurial companies is very high. But it’s also CEO and entrepreneur-centric behavior; most CEOs and entrepreneurs are heat seeking problem solving missiles.

If you are an entrepreneur, CEO, or VC take a moment and think. Do you ever focus on “empathy” rather than “problem solving.” If you want to see an example of this in action, watch Jerry Colonna’s brilliant interview with Jason Calacanis. There’s a lot of incredible things on display in this interview, including plenty of empathy.


I did Digital Sabbath #4 yesterday. I spent the day on Coronado with my dad at Lindzonpalooza, the annual retreat put on by Howard Lindzon. We had a nice time hanging out Friday night as people arrived and then spent Saturday morning hearing short pitches from many of the companies Howard has invested in. I went for a two hour run in the early afternoon and then read Let Your Life Speak: Listening for the Voice of Vocation by Parker Palmer while my dad took a nap and practiced his snoring.

I haven’t been reading much the past six months. Usually I’m a voracious reader – 50 to 100 books a year is not unusual for me. But for some reason I haven’t felt like reading lately. I know some of it is my general mood and some has been the mental exhaustion from writing two books, but I’ve decided to start reading again as part of Digital Sabbath.

My good friend Jerry Colonna recommended Parker Palmer’s book to me. Jerry and Parker are doing a seminar in Boulder on 4/19 called Surviving the Startup Life: The Toll of Merging Identity and Work and, while I’ve heard of Parker numerous times, I’d never read anything by him.

Let Your Life Speak was really good. I read it at a good time for me as I continue to struggle with a depressive episode. Parker covers a lot of stuff but goes deep in one chapter about his own struggles with depression. It’s powerful – and very helpful to me – to read the first person stories about other people who sort through a real clinical depressive episode. Parker covered it bravely – and openly.

I had an excellent talk on Friday afternoon with my dad about what I’ve been struggling with since October. My dad is one of my heroes and closest friends. It’s hard to really connect deeply about this stuff over the phone so we sat for two hours in the sun outside a gelato store, ate our chocolate gelatos together, and talked. I’ve been processing a lot of the root cause of what’s going on and feel like I’m getting underneath some of it, and our conversation helped me get deeper into some of the issues. Parker’s book was a good reinforcement of several of the things I was struggling with.

We finished last night with a nice dinner with everyone overlooking the water and a very lit up San Diego. I just got back from a short run on the beach and am heading out for breakfast with my dad. Then, I’m off to the airport to spend a week in New York.


My close friend Jerry Colonna is giving an extraordinary seminar in Boulder on 4/19 with Parker Palmer called Surviving the Startup Life: The Toll of Merging Identity and Work. Jerry is the best CEO coach I know, a dear friend, and one of the best investors I ever have gotten to work with (we did a lot together in the 1990s when Jerry was partners with Fred Wilson at Flatiron Partners.)

Context on the event comes from Jerry’s blog post titled The Hand of A Friend:

“A distraught client emailed me the day after Jody [Sherman] died. So many people were hurt by the news–whether or not they knew him. I tweeted, emailed, reached out to friends. I wrote to Parker [Palmer].

My request was simple: Help me help them. We decided the best way to respond was to embody what we believe: that speaking about the existential difficulties, being authentic even in our collective guilt, pain, and fear, is–as Parker coined it in Let Your Life Speak–Leading from Within.  We would have a conversation about the ways in which this merger of self and work exacerbates the pain as well as Parker’s notion of the Tragic Gap. We’d invite others to join us.

The conversation is sponsored by Cojourneo and the Center for Courage and Renewal and will be in person on April 19 at 2 p.m. at Naropa University in Boulder.

It’s free. Register here.


I’ve been thinking a lot about  Aaron Swartz the past few days. I didn’t know him, but knew of him and have a lot of friends who knew him. I’m still processing it, especially the dynamics around his suicide, and expect I’ll have plenty to say in the coming weeks about depression and entrepreneurship. In the mean time, I thought the USA Today article, Activist Aaron Swartz’s suicide sparks talk about depressionby Laurie Segal, is particularly good. I’m quoted as saying:

Investor Brad Feld, who has battled an anxiety disorder all his life, says one the hardest things for those fighting the disease is opening up about it. “Many entrepreneurs don’t feel like they can talk openly about their depression, as they don’t want their investors, employees, or customers to know they are struggling with it,” he says. “For anyone who has been depressed, not being able to be open about it with the people around you makes depression even harder to deal with.”

I’ve been lucky in that I’ve had a few people incredibly close to me that I could talk openly about my depression with. The two closest are my wife Amy Batchelor and my brother Daniel Feld. In Amy’s case, she’s my early warning system for my depression. She knows me better than anyone on this planet and is able, in a way that doesn’t set me off, make observations about what she is seeing in my behavior whenever it shifts toward a depressive episode. She goes into a mode that I call “observer” – she’s not critical, doesn’t tell me to “snap out of it”, but also doesn’t get overly concerned. She watches, gives me feedback, and observes. Usually this is all I need since I’ve learned that with my own struggles, merely knowing that I am struggling is often enough to start a shift back to normalcy.

As part of this, I’ve set up a monthly cadence with Amy and Daniel. In the case of Amy, we have “Life Dinner” on the first night of every month. We talk about this in our new book, Startup Life: Surviving and Thriving in a Relationship with an Entrepreneurbut I missed that nuance that in addition to a monthly reflection both backward and forward, it also serves as a touch point on “how I’m feeling.”

Daniel and I do something different. We love the relationship our dad (Stan Feld) has with his brother Charlie Feld. A number of years ago we committed to each other that we’d never get hung up on bullshit between us and if anything came up, we’d clear the air each month. So – we have an “almost monthly” dinner (probably six to nine times a year). I can’t remember the last time we actually had any emotional dissonance of any sort. It’s a casual couple of hours for us to check in on each other.

This morning I was emailing with Fred Wilson about some stuff. He asked me how it was to have Jerry Colonna living part time in Boulder. Jerry is now chairman of Naropa University and is one of my closest friends. He and Fred used to be partners at Flatiron Partners and are still very close. My response was “It’s awesome to have Jerry here. I love every minute I get with him.” Fred responded “i do a monthly lunch with him and its awesome.” There’s that monthly cadence thing again.

Yesterday, I had my monthly meeting with my partners at Foundry Group. We have a quarterly offsite where we spend a day and half together and have recently instituted a monthly day long meeting ending with dinner to go deep on our portfolio now that it’s about 60 companies. We spend the day on the portfolio and the evening on ourselves. It’s yet another version of the monthly cadence that let’s the four of us check in with each other.

I’ve always found rhythms like this to be extremely helpful to me, especially around my depression. Amy, Daniel, and my partners are safe people to talk to about it. They don’t judge me, or coddle me, but they listen and, if nothing else, give me empathy. And, in many cases, they check in regularly to make sure I’m in an ok place, until the phase passes.

Being an entrepreneur, or anyone pressing the boundaries of society, can be incredibly lonely. Make sure you are surrounding yourself with people who can help. And don’t be afraid of being open about being depressed, or anxious, down, or sad. There is no crime or shame in that.