Jessi Hempel from Backchannel just wrote an amazing profile piece on my close friend Jerry Colonna. It’s titled This Man Makes Founders Cry. Medium estimates that it’s an 18 minute read and I assert that it’s worth every minute.
I’ve known and worked with Jerry since 1996. I now get to call him my neighbor as he moved from New York to Boulder a few years ago. If you want a taste of our relationship, I’ve written a lot about him over the years. Following are a few recent ones.
There are a few people other than Amy and my family who I love. For example, I love my partners. I love Len Fassler, who remains to this day my most influential mentor. And I love Jerry.
There are many choice quotes in the article, but to give you a taste, here are a few.
Go read the entire article on Jerry. And, if you want more, go listen to the Reboot podcast.
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.
On my run this morning (yay – I’m running again) I listened to a wonderful podcast between Jerry Colonna and Bijan Sabet called Investors are Human Too – with Bijan Sabet.
If you follow me, you know that I’m incredibly close friends with Jerry (he’s one of the people on this planet that I comfortably say that I love). I’m also a huge fan of his company Reboot.io. If you want a taste of what they do, listen to a bunch of the Reboot podcasts (I’ve listened to them all and the least interesting one is still excellent.)
I’m also a big fan of Bijan. We’ve had a number of great conversations over the years. While we haven’t sat on a board together, I have deep respect for how he functions as a VC – and as a human.
At Foundry Group, we’ve done a number of investments with Bijan’s firm Spark Capital, including AdMeld (sold – very successful investment), Trigget (sold, but not a successful investment), and most recently Sourcepoint. We’ve also got another one in the works together that should close by the end of August.
Unlike so many podcasts with VCs where you get lots of personal history followed by advice, prognostications, bloviating, and predications, this one was all about being human. Bijan and Jerry explored things in the context of the relationship between a founder and a VC. They covered things generally, had some great examples (including Jerry and Mainspring, which was a blast from the past for me), and then Bijan went deep on his own journey to figure this out over the past ten years.
My favorite line came near then end when Bijan talked about encountering VCs who hide behind the phrase “fiduciary responsibility” to justify their actions, when in fact they should just say:
“I have a fiduciary responsibility to treat you like shit.”
Even though I was huffing and puffing on my run, I laughed out loud.
If you are a podcast listener, spend 45 minutes of your life on this. It’s worth it. Bijan and Jerry – thanks for the conversation and for brightening up my run.
I’ve been very open about my struggles with depression over the years. A few weeks ago, I participated in a Q&A with Greg Avery at the Denver Business Journal titled Brad Feld Q&A: Bringing depression out of the shadows in startups. It was part of a more extensive series on Depression, entrepreneurs and startups.
Since I’m still getting emails about it, I thought I’d republish the Q&A here.
Q: How common is the issue of depression in the startup world?
A: Very common, although it is rarely discussed. While the line between stress, deep anxiety, and depression often blurs, most entrepreneurs struggle with broad mental health issues at various points in their lives.
Q: How hard was it to acknowledge your struggle to yourself? And how hard was it to explain it to your partners and your peers?
A: Initially it was extremely hard. When I was in my mid-20s, running a successful company and clinically depressed, I was afraid to talk to anyone other than my psychiatrist about it. I was ashamed that I was even seeing a psychiatrist.
I was afraid people wouldn’t take me seriously, or would stop respecting me, if I talked about how bad I was feeling. The only people I talked openly about it with was my business partner, Dave Jilk, and my girlfriend — now wife — Amy Batchelor. They were amazingly supportive, but even then I was deeply ashamed about my weaknesses.
Q: When did you start to be so open about it?
A: After I became depressed for the second time, in my mid-30s — in 2001 just after Sept. 11 through the end of the year. The last three months of 2001 were awful for me after an 18-month stretch from the peak of the Internet bubble — spring 2000 through Sept. 11, 2001. That was a relentless slide downhill on all fronts.
Sept. 11 was the trigger point for this depression. I was in New York City after a red-eye from San Francisco, landing at 6 a.m. on 9/11. I was asleep in my hotel room in midtown [Manhattan] when the World Trade Center towers collapsed. While I was never in harm’s way, I was terrified, exhausted, and emotionally distressed.
Once I got back to Boulder, I didn’t travel for the rest of the year. In 2002, when most of my VC and entrepreneurial colleagues were having a terrible year, I acknowledged how much I had struggled in 2001, although I was still relatively discreet about it.
When I got depressed again at the end of 2012, I was open about it this time as it was happening and throughout the process. I knew at this point how to handle it and that it would pass.
I also knew many, many entrepreneurs also struggled with depression but, like I had been earlier in life, were afraid to discuss it.
Q: How much does the issue of mental health differ in startups from the world at large?
A: In general, I don’t know. But leaders and entrepreneurs are programmed to “never show weakness”, so I expect there’s much more pressure to keep it hidden and suppressed, which if you’ve ever been depressed, can make things much worse.
Q: Looking back, how much has your work, or work style, been a factor in your depression?
A: There are many things about my depressions that I still don’t understand. I have been able to identify trigger points for the various depressions, which include physiological exhaustion, boredom, and major life changes [divorce, dropping out of a Ph.D. program].
Most recently, things started with a 50-mile race I did in April 2012 that I never physiologically recovered from, followed by a near-death bike accident in September 2012, a very intense stretch of work which included writing two books in the midst of everything — “Startup Communities” and “Startup Life” — the death of my dog, and ultimately a kidney stone that required surgery.
At one level, I was exhausted. I was also bored — my work was fine, but I wasn’t learning very much. I’m hugely intrinsically motivated and have always believed that I’m fueled and motivated by learning. In this case, I was teaching a lot, mostly around “Startup Communities”. But I wasn’t spending any time learning. After coming out of the depression, I realized this was a huge part of things and have subsequently redefined my intrinsic motivation as a combination of learning and teaching. Now that I’m 49, I realize this makes a lot more sense.
Q: How well does the startup and VC world handle issues of mental health? What would you change about it?
A: Until a few years ago, we generally sucked at it. The philosophy around leaders and entrepreneurs never showing weakness dominated and we were told never to let ourselves be vulnerable. Fortunately, leaders like [venture capitalist and professional coach] Jerry Colonna have helped many leaders and entrepreneurs understand the power of being vulnerable and we now at least have an open and productive conversation around it.
Q: Can an executive afford to show any vulnerability and still hope to succeed in leading employees and attracting funding?
A: Yes absolutely. It’s all about culture, style, and self-awareness. And, it’s much easier to be yourself, allow yourself some vulnerability, intellectual and emotional honesty on your path to being a great leader.
Q: What would you say to a founder who’s grappling with depression but feeling their success might hinge on not letting it be known?
A: I mostly try to listen, be empathetic, and introduce the person to other peers who have struggled with the same thing. I talk openly about my experiences, but claim them as mine, rather than suggest that there are generic solutions.
When ask directly what to do, I offer opinions, but I don’t lead with them, nor do I expect that I will — or that I can — solve the person’s problem. I can simply be a resource for them.
Q: Have you actually had these conversations?
A: I’ve had these conversations many, many times.
Q: What do you suggest to people who need help?
A: Talk to your mentors, your peers, and your partners. Take the risk of being vulnerable.
Q: Are there resources you’ve discovered that are particularly geared or well-suited to entrepreneurs?
This is one of my favorite lines to use to explain the business life I live. When asked what it’s like to be a partner in a VC firm, be on a bunch of boards, and have a continuous stream of random interaction come my way, I like to level set my reality.
It’s simple. Something new is fucked up in my world every day.
Now, just because something new is fucked up, doesn’t mean I’m unhappy. Quite the opposite – I’m usually happy, although when the pile of fuckedupness gets high enough I get tired. And day after day after day of 12+ hour days also make me tired. I used to be able to work through the weekends – now at 49 years old I need them to recover, get patched up by Amy, and get ready to go back out there.
Jerry Colonna at Reboot.io tells a wonderful story about the crucible of leadership on Fred Wilson’s blog with a section titled Eat Me If You Wish (read the whole post but the parable is about half way through.) It’s worth repeating here. Take your time reading it.
“One day,” begins a story re-told by Aura Glaser in the latest issue of Tricycle Magazine, “[the Buddhist saint] Milarepa left his cave to gather firewood, and when he returned he found that his cave had been taken over by demons. There were demons everywhere! His first thought upon seeing them was, ‘I have got to get rid of them!’ He lunges toward them, chasing after them, trying forcefully to get them out of his cave. But the demons are completely unfazed. In fact, the more he chases them, the more comfortable and settled-in they seem to be. Realizing that his efforts to run them out have failed miserably, Milarepa opts for a new approach and decides to teach them the dharma.
“If chasing them out won’t work, then maybe hearing the teachings will change their minds and get them to go. So he takes his seat and begins… After a while he looks around and realizes all the demons are still there…At this point Milarepa lets out a deep breath of surrender, knowing now that these demons will not be manipulated into leaving and that maybe he has something to learn from them. He looks deeply into the eyes of each demon and bows, saying, ‘It looks like we’re going to be here together. I open myself to whatever you have to teach me.’
“In that moment all the demons but one disappear. One huge and especially fierce demon, with flaring nostrils and dripping fangs, is still there. So Milarepa lets go even further. Stepping over to the largest demon, he offers himself completely, holding nothing back. ‘Eat me if you wish.’ He places his head in the demon’s mouth, and at that moment the largest demon bows low and dissolves into space.”
I put my head in a demon’s mouth every single day. Often, it’s a different, or new, demon. Sometimes it takes me a few days to get ready for this so the demons back up. Other days two or three new demons appear and I can only deal with one of them so the others hang around.
I learned how to deal with this in 2001. That year started out miserable with companies I was involved failing all around me. I did everything I knew how to do to help. I’d go to bed at the end of the day thinking, “Ok, that totally sucked, but tomorrow will be better.” It wasn’t – each day was worse. By about June I realized that every single day of 2001 had been worse than the previous day. I finally metaphorically threw up my hands and internally said, “Fuck it, let’s see what the world can bring on today.” That’s when I started to sit with the demons.
Up to that point, I was fearful of what the day would bring. I would fight against it. I would thrash around looking to solve every problem, chasing the demons around my cave trying to get them to leave. And then 9/11 happened, on a beautiful morning in New York, while I was fast asleep in a hotel room in midtown Manhatten at The Benjamin Hotel after taking a redeye from San Francisco. As the planes crashed into the World Trade Center towers, Amy frantically called me from the road as she was driving to the airport to come visit me in New York. I had turned off my phone so I expect I snored happily away as the first tower fell. When I finally woke up I to whatever station the clock radio was on, I thought it was all a joke. For about a minute, I struggled through the post redeye haze that enveloped me, along with the existential fatigue I was feeling from nine months of companies failing everywhere, people being angry, unhappy, depressed, stressed, scared, and under immense pressure, and then I realized it wasn’t a dream.
When I finally woke up enough to turn on my phone and call Amy, I was lucky enough to get through. She pulled over to the side of the road and cried. She was sure I had been on one of the planes that had crashed. After a few minutes, we realized a trip to NY was silly so she turned around and went home. I then took a shower and tried to process what was going on and figure out what to do next.
There’s a lot more from that day that shaped me, like it shaped so many others, but suddenly many of my demons just disappeared and went to torture other people. I realized that as fucked up as my world was, it was trivial compared to what was going on 60 blocks away. While I was terrified and trapped in The Benjamin for a while, I had at least four hours before I took action to just sit and process things.
Dealing with the particular set of demons in my cave at this point to another three months. That period was my second of three clinic depressions that ended around my birthday on December 1st. I spent these three months sitting with all of my demons, welcoming more into my world, and just learning from them.
When the really scary ones showed up, I didn’t fight. I just placed my head gently in each of the scary demons’ mouthes and said “eat me if you wish.”
Just like with Milarepa, it worked. And it’s now how I live every day.