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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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My First Experience As A Venture Capitalist

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I often get asked how I ended up becoming a venture capitalist. When people ask me how they can become a VC, I point them to my partner Seth Levine’s excellent blog posts How to become a venture capitalist and How to get a job in venture capital (revisited)But it occurred to me today – after getting another email asking me how I’d become a VC, that I wasn’t really answering the question.

Amy likes to remind me that when I was an entrepreneur, I used to regularly give talks at MIT about entrepreneurship. I’d say – very bluntly – “stay away from VCs.” I bootstrapped my first company and, while we did a lot of work for VCs, I liked taking money from them as “revenue” (where they paid Feld Technologies for our services) rather than as investment.

Feld Technologies was acquired in November 1993. Over the next two years, I made 40 angel investments with the money I made from the sale of the company. At one point in the process, I was down to under $100,000 in the bank – with the vast majority of our net worth tied up in these angel investments and a house that we bought in Boulder. Fortunately, Amy was mellow about this – we had enough current income to live the way we wanted, we were young (30), and generally weren’t anxious about how much liquid cash we had.

Along the way, a number of the companies I had invested in as an angel investor raised money from VCs. Some were tough experiences for me, like NetGenesis, which was the first angel investment I made. I was chairman from inception until shortly after the $4m VC round the company raised two years into its life. Shortly after that VC investment, the VCs hired a new “professional” CEO who lasted less than a year before being replaced by a CEO who then did a great job building the company. During this period, the founding CEO left and I decided to resign from the board because I didn’t support the process of replacing this CEO, felt like I no longer had any influence on the company, and wasn’t having any fun.

But I still wasn’t a VC at this point. I was making angel investments with my own money and working my ass off helping get a few companies that I’d co-founded, like Interliant and Email Publishing, off the ground. I was living in Boulder at this point, but traveling continuously to Boston, New York, San Francisco, and Seattle where I was making most of my investments. During this time, I started to get pulled into more conversations with VCs, helping a few do some diligence on new investments, encouraging some to look at my angel investments, and investing small amounts in some VC funds whenever I was invited to invest in their “side funds for entrepreneurs.”

One of the VCs I overlapped with while in Boston was Charley Lax. Charley was a partner at a firm called VIMAC and was looking at some Internet stuff. I was one of the most prolific Internet angel investors in Boston at this point (1994 – 1995) so our paths crossed periodically. We never invested in anything together, but after I moved to Boulder, I got a call from Charley one day in early 1996. It went something like:

“Hey – I just joined this Japanese company called SOFTBANK and we are going to invest $500 million in Internet companies in the next year. Do you want to help out?”

Um – ok – sure. I didn’t really know what help out meant, but on my next trip to San Francisco I had a breakfast meeting with Gary Rieschel and Jerry Yang. SOFTBANK had recently invested in Yahoo! and presumably the breakfast was to vet me. I remember it being pleasant and ending with Gary saying something like “welcome to the team.”

I still didn’t really have any idea what was going on, but I was making angel investments and having fun. Charley proposed being a “SOFTBANK Affiliate” which had a small monthly retainer, a deal fee for anything I brought in, and a carry on the performance of any investments I sourced. Informal enough for me to play around with it for a while.

I was in Boston the following week so Charley emailed me and said “can you go check out this company Yoyodyne and tell me what you think?” So I went to a generic office park near Boston and met with two people who would become close friends to this day. The first was Fred Wilson, who had just started Flatiron Partners (SOFTBANK was an investor in Fred’s fund) and the other was Seth Godin, the CEO of Yoyodyne. I vaguely remember a fun, energetic chat as we met a few people at Yoyodyne, ran through the products, and talked about how amazing the Internet and email was going to be as a marketing tool.

My formal report back to Charley was short – something like “Seth’s cool, the business is neat, I like it.” SOFTBANK and Flatiron closed an investment in Yoyodyne a few weeks late.

Suddenly I was a VC. An accidental one. And it’s been very interesting since that point back in 1996.

The Importance Of A Monthly Cadence With Close Friends

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I’ve been thinking a lot about  Aaron Swartz the past few days. I didn’t know him, but knew of him and have a lot of friends who knew him. I’m still processing it, especially the dynamics around his suicide, and expect I’ll have plenty to say in the coming weeks about depression and entrepreneurship. In the mean time, I thought the USA Today article, Activist Aaron Swartz’s suicide sparks talk about depressionby Laurie Segal, is particularly good. I’m quoted as saying:

Investor Brad Feld, who has battled an anxiety disorder all his life, says one the hardest things for those fighting the disease is opening up about it. “Many entrepreneurs don’t feel like they can talk openly about their depression, as they don’t want their investors, employees, or customers to know they are struggling with it,” he says. “For anyone who has been depressed, not being able to be open about it with the people around you makes depression even harder to deal with.”

I’ve been lucky in that I’ve had a few people incredibly close to me that I could talk openly about my depression with. The two closest are my wife Amy Batchelor and my brother Daniel Feld. In Amy’s case, she’s my early warning system for my depression. She knows me better than anyone on this planet and is able, in a way that doesn’t set me off, make observations about what she is seeing in my behavior whenever it shifts toward a depressive episode. She goes into a mode that I call “observer” – she’s not critical, doesn’t tell me to “snap out of it”, but also doesn’t get overly concerned. She watches, gives me feedback, and observes. Usually this is all I need since I’ve learned that with my own struggles, merely knowing that I am struggling is often enough to start a shift back to normalcy.

As part of this, I’ve set up a monthly cadence with Amy and Daniel. In the case of Amy, we have “Life Dinner” on the first night of every month. We talk about this in our new book, Startup Life: Surviving and Thriving in a Relationship with an Entrepreneurbut I missed that nuance that in addition to a monthly reflection both backward and forward, it also serves as a touch point on “how I’m feeling.”

Daniel and I do something different. We love the relationship our dad (Stan Feld) has with his brother Charlie Feld. A number of years ago we committed to each other that we’d never get hung up on bullshit between us and if anything came up, we’d clear the air each month. So – we have an “almost monthly” dinner (probably six to nine times a year). I can’t remember the last time we actually had any emotional dissonance of any sort. It’s a casual couple of hours for us to check in on each other.

This morning I was emailing with Fred Wilson about some stuff. He asked me how it was to have Jerry Colonna living part time in Boulder. Jerry is now chairman of Naropa University and is one of my closest friends. He and Fred used to be partners at Flatiron Partners and are still very close. My response was “It’s awesome to have Jerry here. I love every minute I get with him.” Fred responded “i do a monthly lunch with him and its awesome.” There’s that monthly cadence thing again.

Yesterday, I had my monthly meeting with my partners at Foundry Group. We have a quarterly offsite where we spend a day and half together and have recently instituted a monthly day long meeting ending with dinner to go deep on our portfolio now that it’s about 60 companies. We spend the day on the portfolio and the evening on ourselves. It’s yet another version of the monthly cadence that let’s the four of us check in with each other.

I’ve always found rhythms like this to be extremely helpful to me, especially around my depression. Amy, Daniel, and my partners are safe people to talk to about it. They don’t judge me, or coddle me, but they listen and, if nothing else, give me empathy. And, in many cases, they check in regularly to make sure I’m in an ok place, until the phase passes.

Being an entrepreneur, or anyone pressing the boundaries of society, can be incredibly lonely. Make sure you are surrounding yourself with people who can help. And don’t be afraid of being open about being depressed, or anxious, down, or sad. There is no crime or shame in that.

Feld / Calacanis Interview on This Week In Startups

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I always enjoy hanging out with Jason Calacanis. We first met in the mid-1990s when Jason was hanging out in NY doing Silicon Alley Reporter. I can’t remember who initially introduced us – it was probably Fred Wilson.

We covered a lot in the hour+ interview for This Week In Startups. Things like why I didn’t retire at age 30, what Amy’s ring tone is, Startup Communities, Boulder, what motivates me, the different between mentors and advisors, my biggest failures in the Internet bubble, the Foundry Group investment strategy, my angel investment strategy, why Fred Wilson and USV has been so successful, why the objective of a VC is a straightforward and how to define success as a VC, why the answer to “how is a VC fund doing” is “check back in a decade”, hiring for culture fit vs. competence., why entrepreneurs get to – and should – define their culture, why you can’t change people (and how my first marriage blew up), why investors are like D&D characters, examples of bad behavior of VCs and entrepreneurs, more stuff about VC and entrepreneur interactions, what the best board meetings are, a reminder that people lie, Lance Armstrong and ego, CEO coaches, the first person I ever fired, and a bunch of other stuff.

Enjoy!

Jason – you are the Internet’s Charlie Rose. Well done.

Hit Reset, It’s 2013

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Fred and Joanne Wilson Looking HappyMy long-time friends Fred Wilson and Joanne Wilson each had powerful posts about saying goodbye to 2012 and welcoming in 2013 yesterday.

Fred’s is titled Putting 2012 To BedI know many people who don’t know Fred other than via his online presence, public actions, and reputations. I expect that 99% of them, when asked if Fred had an awesome 2012, would say “of course – he has an amazing life.” But my answer would have been more nuanced based on the time Fred and I spent together. I would have said “some great things happened but it was a tough and complex year for him.” Fred’s response was characteristically blunt.

“I’ve wanted to write a year end post for days. I actually wrote one and stored it as a draft. But it comes across as a whiny complaint about the shitty year that 2012 was. And it was in many ways a shitty year for me. But the reason I couldn’t publish that post is it didn’t capture the greater picture that 2012 represents for me.”

The entire post is well worth reading. As is Joanne’s titled See ya 2012. Two big stressors from Joanne’s perspective were the damage to their house with their subsequent displacement from Hurricane Sandy and the shift to being empty nesters as their third kid gets ready to go to college. Her punch line is as powerful as Fred’s.

“This year I am hoping for a constant. I just want to live our lives under our own roof with no major disruptions. I could go for a real year of normalcy. 2013 is going to be a year for moving forward. Reflecting on the past and using that to move me forward. Not sure what that means but I will find out. The last few months we have lived out of more than 7 hotels and it is seriously thrown me off. Where it throws me, I will see. 2012 has taken me out of my game. I am hoping 2013 brings me back.”

My dad (Stan Feld) reminds us in his year end post that life is inches with a wonderful story of his from January 1, 1957.

All three of these posts brought me back to my December 3rd post titled Wow – That Was Intense which summarized a really tough period I went through last year between the start of September and the end of November. My dad’s post was especially poignant since if he had died on 1/1/57 I wouldn’t be here. And I so empathize with Fred – it’s hard for me to complain since overall my existence on this planet is awesome, but I had a really shitty three months at the end of the year.

I hit reset every year on my birthday (December 1) and describe it as “booting up a new version of myself” – in this case, v47. A month later I get to reflect on the reboot as everyone rings in the new year with hope, optimism, and renewal. If you had an Apple II, you know that hitting Reset rebooted the computer, so I’m not of the Ctrl-Alt-Del generation, but rather the Reset PR#6 generation. Either way, use whatever method you fancy and hit reset.

Welcome 2013. I’m looking forward to getting the most I can from the experience.

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Simply Awesome Leadership in Computer Science Education

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I woke up this morning to a post from Fred Wilson titled The Academy For Software Engineering. In it Fred announced a new initiative in New York City called The Academy For Software Engineering. Fred, and his friend Mike Zamansky (a teacher at Stuyvesant High School) helped create this with the support of Mayor Bloomberg’s office and Fred and his wife Joanne are providing initial financial support for the project. If successful, it will have a profound impact on computer science education in the New York public high school system.

Fred’s looking for additional support. I haven’t talked to Amy yet about magnitude, but I’ve already committed via Fred’s blog and sent him a note separately. If you are interested in education in general and computer science / software education in high school in particular, I’d strongly encourage you to reach out as well.

I’ve been working on this general problem (dramatically improving computer science education, both in K-12 and college) for a while through my work at the National Center for Women & Information Technology. More than ever I believe we have a massive education pipeline problem – whether you call it computer science or software engineering or something else. There are several fundamental problems, starting with the curriculum and lack of teachers, but including a total miss on approach and positioning. I expect efforts like The Academy For Software Engineering to take this on directly.

I’m involved in the nascent stages of two projects in Boulder going by the code names “CodeStars” and “The Software School.” I’m excited about each of them and Fred’s initiative and leadership just pumped up my energy by a notch.

Fred / Joanne / Mike (who I don’t know) – thank you! And Mayor Bloomberg – we need a lot more politicians like you who speak their mind and get things done.

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