Brad Feld

Tag: coach

I’ve long written about the stigma around entrepreneurship and depression / other “mental health-related issues.” I was delighted to see two articles in the last day about others addressing this.

First, Felicis Ventures is committing 1% on top of every check the firm writes in non-dilutive capital earmarked for “founder development” in coaching and mental health. I love the way Aydin Senkut has characterized what they are doing and why they are doing it.

“Felicis’ bet is that by making such resources available and publicly known, founders won’t feel too proud, or too much pressure to seem successful, to address personal and team issues. Tactical marketing help can only go so far, Senkut says, when founders aren’t telling their investors that they’re unable to sleep from anxiety, or not speaking to their cofounders.”

Next, Mahendra Ramsinghani has a long article in Techcrunch titled Investors are waking up to the emotional struggle of startup foundersIn it, he references a bunch of stuff, including work that Jerry Colonna and the team at Reboot have been doing around this issue. He also points to the survey he is doing for his new book titled Depression: A Founders Companion.

If any of this resonates with you as a founder, (a) go complete Mahendra’s survey, (b) connect with Reboot, or (c) send me an email to connect you with Mahendra or Reboot.


Today’s #GivingThanks post is for my dear friend Jerry Colonna. When I make a list of non-family members and non-partners who I would want to be stranded on a desert island with, Jerry is at the top of the list.

Before I tell a story, if you want to participate in #GivingThanks to Jerry, please make a donation to Naropa University where Jerry is the chair of the board. I was going to try to create some kind of complicated matching donation scheme since I hadn’t made a gift to Naropa yet this year but I decided to just gift them $10,000 (which I just did now through the website) so I encourage you to support at any level if you want to participate in my not-so-complicated match.

I met Jerry in 1995. I was chair of NetGenesis, which was the first angel investment I’d made after selling Feld Technologies (my first company). NetGenesis had raised some money and had created three different products – net.Forms (a web form manager), net.Thread (a web threaded discussion board), and net.Analysis (a weblog analysis tool). While our customer for each product was the same (a webmaster or a company trying to build a website), we were having trouble leading with all three products. Allaire was eating our lunch on .Form, a company called eShare was picking us apart on .Thread, and this new company called WebTrends was torturing us on .Analysis. A year earlier, none of this had existed – now we realized we needed to focus on one product. We chose net.Analysis and went about selling the other two products to different companies.

Jerry had just invested in eShare. Somehow Raj Bhargava (the NetGenesis CEO) had connected with Jim Tito (the eShare CEO) and worked a deal to sell him net.Thread. NetGenesis got some of eShares equity, eShare got the net.Thread product, and I joined the eShare board.

That started a 20+ year relationship between me and Jerry that I comfortably use the word “love” to describe.

Jerry became partners with Fred Wilson and they started Flatiron Partners. We all started working with SoftBank as affiliates (along with Rich Levandov). I eventually co-founded SoftBank Technology Partners (which became Mobius Venture Capital) and SoftBank (the corporation) became a 50% LP in Flatiron with Chase. We made more investments together. As Jerry and Fred’s relationship evolved, so did mine (with each of them) as we had different kinds of professional and personal connections.

I remember a moment in what must have been 1999, sitting at Jerry’s desk in NY in a dark office (I never really like office lighting so I work without it on and it had turned into evening in NY.) I was trying to get a deal done and it was a stressful mess. The tension of the Internet bubble bursting hadn’t started yet, but I was already exhausted and negotiating basically all the time with everyone about everything. I hung up the phone and put my head down on Jerry’s desk. I wasn’t crying, but I was probably in a parallel emotional zone. Jerry walked in the room, saw me, and wrapped his whole body around me and just covered me up. It was one of those moments I’ll never forget – total, compete emotional intimacy in the context of support. I’m sure he was feeling the same kind of stress and in the moment we just hugged. And then I cried.

Jerry has a super power – he makes grown men (and women) cry in a business context. But that’s the super power – it’s not a business context, it’s life, and he helps us understand that in powerful, unique, and profound ways.

In 2002 Jerry retired from venture capital and went on his own personal journey for meaning. He was an extremely successful VC but woke up one day hating the work, feeling unfulfilled, and struggling with what became a deep depression. I was fighting my way through my own dark shit then so we didn’t see each other often, but when we did it was extremely helpful to me. There was an immediate sense of comfort, of love, of empathy, and of understanding. It didn’t matter what we talked about – we were just there, together, in the moment.

Today, Jerry runs a CEO coaching company called Reboot. Their mission – front and center on their website – says it all.

“We believe that in work is the possibility of the full realization of human potential. Work does not have to destroy us. Work can be the way we achieve our fullest self. Reboot is a coaching company. We help entrepreneurs and their teams deal with the internal ups and downs of entrepreneurship and support the growth they need to improve their performance and their life.”

I believe that Jerry is the best CEO coach on this particular planet. I’ve seen, and experienced, his magic many times. He’s found his purpose in life, and it’s wonderful to see him practice it every day.

Jerry also moved to Boulder last year. That means I see him a lot more in person that I used to. I still have to make a mental adjustment when Amy and I run into him and Ali on the Pearl Street Mall heading off to different restaurants for dinner, but an enormous smile always crosses my face when it happens.

Jerry – thank you for being you. And for everything you do in this world.


I was catching up on a bunch of reading on the web from last week and came across a post by Lars Dalgaard titled Thoughts on Building Weatherproof CompaniesI don’t know Lars, but know of him as the founder/CEO of SuccessFactors and now a partner at A16Z, and was curious after recently reading a Forbes article about Zenefits a few weeks ago titled ‘A Lot Of Things Went Wrong’: Lars Dalgaard On Zenefits Scandal.

Any CEO I’ve ever worked with has heard me say “build the company and make decisions as though you’ll be running it forever” many times. While forever is a very long time and so far the idea of running a company forever hasn’t happened, it’s a great frame of reference for a CEO to operate from. So, I found myself nodding at a bunch of things Lars wrote in his post and I encourage you to read it.

Following are a few of the headlines of the points that resonated with me along with my quick thoughts.

Successful companies are bought, not sold: This cliche is said 100x per day by VCs. And it happens to be true. Build something great and important and opportunities to be bought, whether you want to pursue them or not, will come to you.

Develop a perpetual, aggressively help-seeking mindset: A simpler way to say this is “learn quickly, do it continuously, and surround yourself with people you can learn from.” There’s a subtext about sublimating your ego and fears, which appears in several other parts of the post and is a characteristic of everyone I know who is a learning machine.

Invest in a coachMany of the CEOs (and founders, and execs) we work with have coaches. We strongly recommend them. My partners and I have used Nancy Raulston since we started Foundry Group and my extremely close friend Jerry Colonna is someone I describe as “the best startup CEO coach on the planet.” I have a running coach, even though all I do is run marathons, and not competitively. I’ve never understood why people who are trying to be excellent at something don’t recognize the value of a coach.

Build a real board of directors … and use itI’ve long been an advocate of building a real board early in the life of your company. Lars talks about adding non-VC directors early and I strongly agree. I’ve seen too many boards that are just gradual expansions of the number of VCs around the board table with each successive round of financing. While the CEO works for the board, a great board effectively works for the CEO also, doing whatever it can (as individuals and collectively) to help the CEO be successful with one fundamental governance role – that of insuring that if the CEO is not being effective, the board can take action to change this, which often, but not always, means replacing the CEO. If you want to go deeper on this, I’ve written a book on it called Startup Boards: Getting the Most Out of Your Board of Directors.

Kill the monsters of the mind, while preserving your spiritWhile a provocative title, I’m not sure your goal should be to kill the monsters of the mind. In my post titled Something New Is Fucked Up In My World Every DayI tell a short version of the Buddhist saint Milarepa’s story Eat Me If You WishComing to terms with the monsters (or demons) is much more powerful (and efficient) than killing them, since it often makes them simply disappear.

Don’t lie to yourselfI remind you of the great John Galt quote “Nobody stays here by faking reality in any manner whatever.” If you ever stay in my guest condo in Boulder, you’ll see a painting by my mother with this quote incorporated into it hanging on the wall.

It’s Sunday – if you are reading this, take some time to read Thoughts on Building Weatherproof Companies and ponder it in the background, instead of burning brain cells on whatever political crap is discussed on the internets today. Lars, thanks for taking the time to write it.


Our Foundry Group CEO list lit up this morning with a question about CEO coaches and whether they were helpful.

My quick response was:

I think a great CEO coach can be awesome and not-great CEO coach can be very detrimental. Jerry Colonna is the best CEO coach I’ve ever met or worked with. There are others that I’m sure will emerge from this discussion but make sure you know what you are getting / looking for.

Like many of our CEO threads this one filled up quickly with great thoughts and suggestions. Then one just nailed it.

“The key for me is that it was a cross between coaching and therapy. You can talk about business issues *in the context* of how you feel about them. This is a crucial benefit, because no matter how good your relationship with board members, expressing those feelings necessarily affects the business conversation; and no matter how astute your spouse, he or she is likely not to put enough weight on the business considerations. Consequently, the normal mode for a CEO is to have all of it in your head; and sometimes it just rolls around in there and makes you crazy.

I suspect this is true no matter how “transparent” you are.

Consequently, the key for a CEO coach is that they be able to quickly understand the business issues AND the emotional issues, and tie them together.”

CEO coaches aren’t for everyone, but I’ve seen amazing impact when a CEO gets a match with a coach that fits well with what he/she needs. And I’ve also seen the opposite – total mismatches between coach and CEO that drove the CEO over a cliff. Make sure you know what you are looking for, and assess regularly what you are getting from the relationship. But don’t be afraid to try.


A few years ago my running coach – Gary Ditsch of Endurance Base Camp – introduced me to the idea of a “double long run.” In this I do the typical weekend long run on a Saturday and then repeat it on Sunday. At first, I hated these, but they’ve grown on me and are now my favorite run.

Today I did a 16 mile run in San Francisco that followed a 14 mile run on Saturday. I did the same run (Market to Embarcadero to the Golden Gate bridge, over, and then back) but added on an extra mile on the bridge today just because I felt like it. I think this is the furthest double long I’ve done (30 miles) – I know I’ve done some in the low to mid 20’s, but I felt like I broke through to a new level today.

I also covered 45 miles this week. This is the first week I’ve done 45 miles in a decade and remarkably it was only on four days of running (I usually run five days a week, sometimes six). I had two early morning flights (to Kansas City on Tuesday, back home on Wednesday) and didn’t run either day. I also had a rest day on Friday. So, I’m closing in on 50 miles a week, which feels great.

I’m gearing up for back to back weekend marathons in October – Newport, Rhode Island on 10/16 and then St. Louis on 10/23. I was a little nervous about my ability to get these done, but my rapid recovery from the Bismarck marathon two weeks ago and the monster week I just did has me feeling good.

For all of you out there supporting my running, especially Amy, thank you!