Bringing Depression Out of The Shadows In Startups

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?

A: Jerry Colonna’s Reboot.io is the best organization in the world for this.

Cash Policies for Startups

I heard a rumor on a call the other day that some startup companies are starting to keep balance sheet cash in higher yield instruments such as corporate debt. This is apparently becoming trendy again as private companies do $25m+ rounds and end up with a bunch of cash on their balance sheets.

This scares the shit out of me. As a high growth startup, I think you should be focusing on maximum protection for your cash, even if the yield is 0%.

In 2001, we had several companies lose over $1m (including one that was public that lost $7.5m) in corporate bonds, which were being pushed on startups by the various banks as “safe.” We also had at least one case of a mess in the 2008-2009 time period with someone with one of those fancy action rate securities that froze cash for a while (they eventually got it.)

And when I say “lose”, I mean the cash just vaporized. I remember seeing the email about the public company that had $7.5m disappear from their balance sheet. No one on the board was even aware that cash was tied up in corporate bonds, let along risky yield seeking ones. It was a powerful signal, at which point I actually spent time learning about the corporate debt market. It’s a good case of “it’s nice until it isn’t, and then it’s really not nice.” It’s probably even more severe today.

Don’t fall into this trap. It’s worth double checking your cash / treasury policy at your next board meeting and making sure your board knows where your cash is. And, more importantly, if you are CEO, knowing where your cash is.

Be careful out there. The scary monsters are starting to hang out at the bar again. They look really cute, cuddly, and intriguing, until they don’t and chomp down on a random body part.

Hint: US Government Treasuries are good.

The Full Day Quarterly Board Meeting

Mattermark team hanging out in KeystoneI’ve been to a gazillion board meetings. I’ve written a lot about them including a book called Startup Boards: Getting The Most Out of Your Board of Directors and piles of board meetings posts on this blog. I still do a lot of them, but I’ve definitely been on a quest the past few years to (a) figure out what works best and (b) try to organize my world around more effective board meetings based on what I’ve learned.

On Friday, I had a Mattermark board meeting. It was our second one since we invested in Q414. Danielle Morrill wrote a post in February about our first board meeting. It was a long board meeting as I’d reserved from 11am until the end of the day for it, followed by dinner together, but it was very different than the one we just had as we search for our rhythm as a board.

At the first board meeting, Danielle, Kevin, and Andy came to Boulder and spent a few days here together. In addition to the board meeting, they spent a bunch of time with founders in other Boulder-based portfolio companies of ours.

This time the Mattermark leadership team, including Sarah, BT, and Beau came to Colorado. They arrived Thursday night and drove up to my house in Keystone (about 90 minutes away). I got up early Friday morning and drove up there, getting there around 10:00am. The Mattermark gang was up, had just finished breakfast, and were doing what lots of startups do when they are hanging out waiting for an investor to show up (queue photo of people sitting around on their laptops.)

We got a little more coffee and then went downstairs into our big, comfy TV room. Last time, we worked directly in a Google Doc. This time, Danielle made a deck summarizing everything we’d been doing back and forth in via the Google Doc over the past week leading up to the board meeting. The deck looked good on our 75″ TV and we fired up Skype on a laptop at the front of the room for Lisa (who couldn’t come) and Megan (our outside counsel.)

We proceeded to spend until almost 8pm going very deep on various aspects of the business, product, product strategy, organizational dynamics, and goals for Q215. During this time, we took 90 minutes off for lunch and had a bunch of Mexican food at Fiesta Jalisco. At about 7pm we shifted into an executive session of just founders and board and then Danielle and I spent 30 minutes just doing a 1:1.

We then jumped into cars and went out to a late dinner. My favorite Sushi place Kemosabe Sushi had an hour wait so we went to Silverheels Bar and Grill next door. We were done talking business so we talked science fiction, crazy obsessive habits, fun ways everyone had met each other, and the stuff you talk about after a long day together.

They then drove back to my Keystone house to spend the rest of the weekend together. I drove home because I really wanted a weekend with Amy just hanging around and chilling out (she’s taking a nap as I write this.)

Overall, I’ve tried to shift my board meeting rhythm to once a quarter. My favorite board meetings are the ones that including the entire management team. I like to have a meal with the entire management team as part of the board meeting. I like to have social time and give the team time and space to get to know me better, and themselves better, outside the normal pressure of the day to day grind that is startup life.

I’m a very deep believer in continuous engagement with companies I’m an investor in. As a result, I do not like a monthly board meeting rhythm. I think it’s too much overhead on a leadership team and lets investor / board members off the hook for continuous engagement. More specifically, I know many investors who only really engage with companies either around the board meeting, when a transaction is going on, or when there is a crisis. While this might be useful for some people, it’s not my style nor how I like to engage.

I’ve only had a few of these “full-day retreat at my house in Keystone followed by management taking over the house” type board meetings and I really like them. I expect I’ll do more in the future and encourage any of the companies I’m on the board of to take me up on them.

Desperately Seeking a Solution to Google Hangouts Errors 212, 213, 214, 215, 216

Google Hangouts ErrorI’m a huge Google Hangouts user. It’s typically a multi-day occurrence that I’m on a hangout and one of the devices connected to the mega-video-conferencing setup in my office is a Chromebox.

A few months ago I got Google Hangouts errors intermittently for a few weeks but it magically cleared up. I noticed it again on Sunday and it has been constant on all my computers in multiple locations on different networks.

I’ve tried clearing the cache, logging out, and resetting the browser / computer, which seems to be the only constructive solutions I can find on the web. The other solutions, that are not so constructive, are “wait for a while for it to clear up” and “use something different.”

Strangely, this problem only exists in Chrome. My iOS Hangouts works fine as does my Chromebox.

Does anyone have a clue how to solve this nagging problem? The screen shot I’m getting in Chrome when Gmail is open is on the left.

Something New Is Fucked Up In My World Every Day

In The Cave of DemonsThis 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 thelatest 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.