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Hi, I’m Brad Feld, a managing director at the Foundry Group who lives in Boulder, Colorado. I invest in software and Internet companies around the US, run marathons and read a lot.

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The Deep, Dark, Emotional Challenges of Being a Leader

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I got to spend a lot of time with my close friend Rand Fishkin the past few days. The first was at Denver Startup Week, where we did a panel discussion with Ben Huh and Bart Lorang where we discussed the pact between CEO and Board, the pact between Founder and Investor, and how to be transparent and direct.

The next day, Rand led a full day offsite for a number of CEOs in our portfolio.

In between, he wrote an epic blog post titled A Long, Ugly Year of Depression That’s Finally Fading. Go read it now – I’ll wait.

I love Rand – not in that surface “I love you man” kind of way. Ever since I met him and his wife Geraldine, I’ve adored them as a couple and each as individuals. I often develop deep personal relationships with the people I work with which can be challenging when businesses struggle and difficult decisions have to be made. I’ve had a few friendships fail as a result of the pressure, stress, and intensity of working through certain situations, but far more have strengthened as a result. It’s a risk I decided to take a long time ago and I’ll continue to do it, even when I have to cope with my own anxiety, emotional struggles, and even depression, as a result.

We invested in Moz in April 2012. Rand wrote so extensively about it in his post Moz’s $18 Million Venture Financing: Our Story, Metrics and Future that almost all of the major tech blogs declined to write about it “because all the news was covered in the post.” Whatever.

The first nine months were great – the business grew as planned as I started to get to know everyone and how things worked at Moz. The company was working on a major rebrand (from SEOMoz to Moz) as well as a huge software expansion which was started before I invested. But by mid-year 2013 things were not going as planned. Rand has written extensively about it, but when he and Geraldine visited us in Boulder for a few days around that time both Amy and I thought Rand was depressed.

By the winter time, Rand had decided to hand the CEO roles to his longtime partner and COO Sarah Bird. Shortly after, he acknowledged his depression in his post at the end of 2013 when he wrote Can’t Sleep; Caught in The Loop. Regardless of his struggle, he continued to work incredibly hard, but we started having a different conversation, this time as friends rather than investor / board member and CEO / founder. I was more concerned about Rand’s mental health than his activity at Moz, and our conversations were generally around this. At the same time, Sarah grabbed the CEO reins firmly and has done an outstanding job, which I knew would ultimately be helpful to Rand.

Rand looked better in the past few days than I’ve felt he looked in several years. I was thrilled to see his post come out between our rambling Denver Startup Week discussion and the full day of the CEO offsite.

Most of all, I’m delighted that my friend Rand’s depression is finally starting to fade. Rand – you are amazing – and loved by me and many. Carry that with you all the time.

Negative Maintenance

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I had a fun email exchange with an investor I’ve worked with for almost 20 years in response to something a CEO send out from a board we are both on. I said “fucking awesome.” He said “that’s an understatement.” I said “CEO is such a delight.” He said “CEO is negative maintenance.”

I loved this. So I’m going to use this post to think through the idea out loud and I’d love your feedback since it’s still a messy / blurry concept in my mind.

My hypothesis is that the opposite of high maintenance is not zero maintenance but rather it’s negative maintenance.

There are days that I’m high maintenance. Everyone is. But if you subscribe to my “give before you get”, or #givefirst, philosophy, you are constantly contributing more than you are consuming. I’ve talked about this often in the context of Startup Communities, but I haven’t really had the right words for this in the context of leadership, management, and employees in a fast growing company.

Suddenly I do. When I think about my role as an investor and board member, I’m often tangled up in complicated situations. I’ve often said that every day something new in my world gets fucked up somewhere. This used to be distressing to me, but after 20 years of it, if I don’t know what the new fucked up thing is by 4pm, I start to get curious about what it’s going to be.

We all know that creating companies from nothing is extremely difficult. The problems that arise come from all angles. Some are exogenous and some are directly under your control. Some are random and some are obvious. Some are compounded by other problems and mistakes, resulting in what my father taught me at a young age was the worst kind of mistake – one that was a mistake compounded on a mistake compounded on a mistake – which he called “a complicated mistake.”

Personally, when I find myself in a complicated mistake, I stop. I step back and pause and reflect. And then I try to figure out how I can change the dynamic into something positive, not continuing to build on my complicated mistake, but instead getting clarity on what the right thing is to do to get out of the ditch.

Negative maintenance people do this. I’ve seen, been involved in, and made some epic mistakes. The CEO I’m referring to above has a great company, but has also experienced some epic mistakes. How he handles them, works through them with his team, and his board, is exemplary. There is work involved by me and the other board members, but it’s not inappropriately emotional. It’s not high maintenance. It’s just work. Decisions have to be made and executed. And there are impacts from these decisions, which lead to more decisions. Ultimately this CEO is putting energy into the system as we work through the issue, which is where the negative maintenance (as opposed to high maintenance) behavior pattern arises.

I like this idea of negative maintenance people. I’m obviously trying to think it through out loud with this post, so weigh in and help me understand it better.

The Colorado CEO Jobs List

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A few years ago, David Cohen and I started a Colorado CEO Jobs list in response to the regular stream of inbound email we got from folks looking to move to Colorado and interested in tech-related jobs. We seeded this list with CEOs from companies Foundry Group and Techstars had invested in. As other CEOs requested access to the list, we added them.

The list was managed in Yahoo Groups and had about 100 CEOs on it. It was simple – emails from people looking for jobs came to me or David and we forwarded them to the list. The hit rate was very high – I regularly get feedback from people that they’ve ended up with multiple interviews and a job from the introduction.

Both David and I felt like the list was pretty tedious to manage in Yahoo Group so about three months ago we restarted it and made it a Google Private Community. We culled the list a little and re-invited everyone, ending up with 56 active CEOs. We’ve been using the Google Private Community for a while and are comfortable that it’s a significant improvement over the Yahoo Group.

We are still keeping it private for now but are looking for any CEOs of tech companies in Colorado who want to join the list as we expand it from Foundry / Techstars related companies. Our goal is to have a wide audience of CEOs for anyone coming to Colorado who is looking for a tech related job.

We are keeping the list ONLY to CEOs for now as we plan to expand some of the things we are doing with the list.

So, if you are a CEO of a tech company in Colorado and want to be on our Colorado CEO Jobs List, just email me (brad@feld.com).

And – if you are looking for a job in a Colorado tech company, email me also and I’ll forward your info to the list.

Improv and Entrepreneurship – Playback Theatre West

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I spent the last few days at CEO Bootcamp – Leadership Reboot. It’s run by my close friend Jerry Colonna with an awesome team of four. The next one is going to be in Tuscany, Italy from 6/4/14 – 6/8/14 and I expect it will be amazing. I encourage you to explore it and apply – the deadline for applications is 4/20/14. I arrived at Devil’s Thumb Ranch on Wednesday afternoon.

The first evening was a wonderful dinner and introduction to each other (about 20 of us) along with an evening session with a taste of what was to come. I attended as a special guest (I’m the only non-CEO / entrepreneur here) but participated as a peer.

Thursday was extremely intense with the focus on what a CEO does and the five challenges of a CEO. Everyone opened up, the discussion was incredible, and emotions were high, and yes, there were tears, as  one of Jerry’s superpower’s is getting the tears to flow.

If you need a taste of Jerry and haven’t seen him in action before, the following TWIST Interview on The 6 Biggest Mistakes Founders Make is dynamite. By Thursday evening, we were deep into it. Some people were tired (I ended up taking a nap for 90 minutes during the late afternoon break), others were confused, and some were inspired. A word that was repeated regularly was grateful. Grateful to be with peers. Grateful to realize one wasn’t alone. Grateful to be able to be human in the midst of a group of other entrepreneur/CEOs.

A magical thing happened after Thursday dinner. The gang from Playback Theatre West came and spent two hours with us. I’d experienced Playback Theatre West last year at Boulder Startup Week. I was one of the stories they performed – I shared my story of moving to Boulder with Amy and they re-enacted it – interpreting things in real time – magnificently. Since I knew what we were in for, I knew that once things started happening the collision of improv and entrepreneurship would be a wonderful capstone to the day.

After a warm up, Rebecca asked for volunteers. Sam, who had been with us all day (as he’s one of the CEO Bootcamp founders as well as a member of Playback Theatre West), was one of the actors.There was a lull – everyone was unsure what to do next. So I stood up and went first.

When I stood up, I had no idea what story I was going to tell, so there was some meta-improv going on. By the time I sat down next to Rebecca to start telling my story, I decided I’d tell the story of my 50 mile race. The emotional fallout from the race, which I only mildly understood two weeks after I finished it, has had a profound impact on how I’m currently living my life given the deep depression that set in for me about seven months after the race and then lasted six months.

I told the story of the race. Rebecca and the gang asked questions along the way, pulling out pieces of my motivation for the race, along with the implications of the race. Some of the questions were simple, like “Why”, but set me off on a tangent that had nothing to do with the race. Then I sat back and watched them perform for five minutes. I laughed. And then I laughed some more. And then I had tears in my eyes. And then a wave of emotion flowed over me as I made a connection to something I hadn’t realized before. And then I settled down and smiled as they tied together some threads around my own motivations that had eluded me.

They did several more performances for different CEOs in the room including one about a hiring story that was happening and was unresolved and one about starting a company. Each was a hilarious and absolutely beautiful interpretation of the story told. After a super heavy and intense day, it was a perfect way to wrap things up. To realize we are all humans, by acting out the reinterpretation of our human stories.

I’ve become a huge fan of Playback Theatre West. I hope to do a lot more with them in the future.

The Duo

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I’ve been thinking about the concept of “the duo” a lot recently.

Many of the companies I’m involved in have either two co-founders or two partners who partner up early in the life of the business. Examples of founding partners including Andrei and Peter (Kato.im), Keith and Jeff (BigDoor), James and Eric (Fitbit), and Matthew and Cashman (Yesware). Of course there are many other famous founding duos like Steve and Steve (Apple), Jerry and Dave (Yahoo!), Larry and Sergey (Google), and Bill and Paul (Microsoft). My first company (Feld Technologies) had a duo (me and Dave) and the company that bought Feld Technologies did also – Jerry and Len (AmeriData).

But many of the companies I’m involved in have duos that develop over time. Sarah and Rand (Moz). Bre and Jenny (MakerBot). Matt and George (Return Path). David and David (Techstars).

Now, these duos are not the leadership team. But there is a special magic relationship between the duo. I like to think about it like the final fight scene from Mr. and Mrs. Smith where Brad and Angelina are back to back, spinning around in circles, doing damage to the enemy.

This is not just “I’ve got your back, you’ve got my back.” It’s “we are in this together. All in. For keeps.”

It’s just like my relationship with Amy. We are both all in. It’s so powerful – in good times and in bad times.

Build something great with me