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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.

Brutal Honesty Delivered Kindly

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In yesterday’s post Mentors 4/18: Be Direct. Tell The Truth, However Hard, Joah Spearman left a very powerful comment about empathy.

“The older I get the more I realize that truth is something that is best coupled with empathy. Ultimately, you have to seek to understand before you can be understood and part of telling the truth is knowing that you’ll never know someone else’s truth until you hear it directly from them rather than assuming you know what someone has experienced or what’s best for them.”

This made me think of a deeply held belief that I hold with my partners at Foundry Group – brutal honesty delivered kindly.

When I invested in Moz, I thought a lot about TAGFEE, which is Moz’s code that reflects their core values.

Transparent
Authentic
Generous
Fun
Empathetic
Exceptional

I especially keyed in on Transparent, Authentic, and Empathetic as these three are core personal values of mine. However, these three ideas often come into conflict. It’s hard to be transparent and empathetic at the same time. Consider the situation where you fire a person. Legally, you likely have some constraints on what you say, limiting your transparency. You want to be empathetic to the person you fired, so this again limits your transparency (or, if you are transparent, you likely aren’t being very empathetic.) And then, at a meta-level, you will have some internal struggles with your authenticity around this situation.

The tension between the concepts is helpful as it makes you think harder about how you comport yourself is difficult, challenging, or complex situations.

The solution between me, Seth, Jason, and Ryan is to be brutally honest at all times but deliver feedback kindly.

While I’m sure we hold back on occasion, especially when one of us is unclear on what is going on, we subscribe to the notion of brutal honesty. We try hard to be fair witnesses in the style of my wife Amy, saying what we believe to be the truth. When it’s a hypothesis, we frame it as such. When it’s an assertion, we state that. When it’s something we feel strongly about, we preface it appropriately. And when it’s a fact that we are certain of, we are unambiguous in what we say.

No matter how difficult, sharp, upsetting, or confrontational something is, we always deliver the message kindly. We are not decedents of the Stepford Wives and we each have our own personalities, so “delivered kindly” means something different for each of us. But we never mean malice, harm, or disrespect. We are quick to own our opinions, especially when we are wrong. And when on the receiving end, we listen, and try to understand the other person’s truth, as well as our own, and then reconcile them.

If you sat in a meeting with us, you’d see no yelling. No pounding on the table. No grandstanding. No aggressive body language. No passive aggressive behavior. But you would hear a lot of brutal honesty, And you’ll hear it delivered kindly.

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.

Sometimes You Just Want To Scream

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I’m on the receiving end of phone calls and video conferences with CEOs all day long. And, at least once a day, I can feel the intense stress on the person I’m talking to oozing through the phone or the screen. The conversation is often calm and rational, but below the surface is a bubbling cauldron of pressure.

Welcome to life as a CEO of a fast growing startup. Every day something new and unexpected comes at you. Often multiple things. Some are awesome. Some are ok. Some are bad. And some are awful.

Ben Horowitz wrote what I think is the best post ever on this called The Struggle. After I read it, I asked him if I could include it in my book Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur. He graciously said yes, so I did.

I felt The Struggle regularly when I was running Feld Technologies in the 1980s. I put myself at a disadvantage – when something went wrong people often called for “Mr. Feld.” My partner Dave carried a lot of the burden as well so I wasn’t alone, but I was on the receiving end of a lot of unhappiness over the years.

While I got better at compartmentalizing it, I never mastered it. I still struggle with it today. I can absorb an enormous amount of stress from the CEOs I work with. But sometimes I get overloaded and end up far out on a deep tree limb trembling with anxiety. I like to refer to this as “inappropriate anxiety” because I know exactly what is at the root cause, but my obsessive mind has a difficult time letting it go.

So I do what I can. I talk to Amy. I walk Brooks the Wonder Dog. I take a bath. I try to sleep a little more. I run more. I let the obsessive thoughts roll around in my head, chasing each other like characters from SpongeBob SquarePants.

And sometimes I just go in a closet and scream for a little while. I let all the bad energy out. I put my all into it – expelling the stress. Trying to reset my mind. Knowing that the inappropriate anxiety will go away and I’ll feel ok again.

When I hear this in the voice of a CEO I’m working with, I offer up myself as a release valve. While I don’t invite it, I want them to know they can vent to me. That they can bare their soul safely to me. That I won’t judge them on the pressure they are under. That I won’t try to solve the problem for them.

But that I’ll be there.

And I let them scream if they want to.

CEO Bootcamp with Jerry Colonna

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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.

Build something great with me