Brad Feld

Category: Entrepreneurship

Last night, during dinner with the Return Path board, Fred Wilson interrupted the discussion we were having to tell us that Steve Jobs had just passed away. All of us were stunned silent for a minute as we reflected on the amazing impact that Steve has had on our lives. While I don’t have a personal relationship with Steve, he’s been a hero of mine since I was a teenager when I bought an Apple II computer with 16K of RAM in 1978 with my Bar Mitzvah money. To this day I still remember the sound the disk drive made when I typed PR#6 and how excited I was when I got a Silentype printer.

After dinner, as I reflected on what I knew about Steve and watched as my Twitter stream revealed link after link in tribute to him, I thought about the contemporary moment that meant the most to me. I recalled watching his Stanford Commencement Speech from a few years back and having chills. So – in tribute to the passing of this amazing man, I encourage you to spend 15 minutes and hear something powerful, in his own words.

Steve – while you didn’t know me, thank you for everything you’ve done that has inspired me and impacted my life.

One more thing…


I’ve often said that two emotions that are irrelevant for an entrepreneur are fear and anxiety. My favorite quote from Dune is “Fear is the mindkiller” and many people get confused and don’t understand the difference between panic and urgency (where panic is just a more extreme version of anxiety.)

Several weeks ago I spent an evening and a day in Colorado Springs. I participated in a number of entrepreneur-related events, but my favorite was a talk that I gave to a freshman class at University of Colorado at Colorado Springs with John Street. John is a long time friend and one of the first entrepreneurs I met when I moved to Boulder (I actually met his wife Mary through YEO’s Birthing of Giants program in 1993 when I was still living in Boston.) In addition to being a good friend, John is a very successful entrepreneur who has had plenty of ups and downs and ups, but has perserved through it all and created several important companies.

The class that we spoke to was a freshman seminar about “Being Your Own Boss.” John and I quickly told our stories and then spent the majority of the time answering questions. One of them was something like “what characteristics have made you successful.”

John went first and stated the two most important things about him were that he is “tenacious” and “oblivious”. Having known John for many years, tenacity defines him. He simply does not give up. While he can appear stubborn, he’s a learning machine, open to any feedback, constantly asking questions – especially when faced with challenges, and searching for better approaches on his quest to solving any problem he encounters. I view this as a perfect example of a tenacious entrepreneur.

I was puzzled by oblivious until John explained it. He said that he’s oblivious to why something can’t be done, or why something is difficult, or why someone doesn’t want something to happen. That made perfect sense to me and is a characteristic of many of the great entrepreneurs I’ve worked with over the years.

I followed up John with my rant on fear and anxiety. I explained that these are normal human emotions that often are helpful, especially when you are in physical duress (fear = fight or flight) or struggling to understand something new or uncertain (anxiety). However, when viewed from a business perspective, my view is that “fear is the mindkiller” and “anxiety slows you down at a moment when you should increase your urgency.”

I added two new thoughts to my view of what makes a great entrepreneur – tenacity and obliviousness. Think of your favorite entrepreneurs – do these apply?


I was reminded of the importance of starting with the customer experience while I was watching this brilliant video from WWDC 1997 of Steve Jobs. In the video, Jobs appears to be responding to attack by a troll, but is actually doing something much more interesting. Rather than take the bait and react, he thinks carefully in real time and makes a critical philosophical point about his – and Apple’s – approach to creating new products.

The punch line happens early when he says “you’ve got to start with the customer experience and work backwards for the technology.” It’s five minutes long and worth watching, if only to see how incredibly durable Jobs’ philosophy has been over the past 15 years.

When I think about the companies we’ve invested in, some of them embody this philosophy deeply in their culture. Oblong, MakerBot, OrbotixFitbit, and Cloud Engines immediately come to mind. The entrepreneurs running these companies are completely and totally obsessed with the consumer experience of their products, even though their products embody an incredible amount of technology (in each case, both hardware and software innovations.)

As an investor, I often lose sight of this, especially when I’m working on non-consumer facing companies (e.g. enterprise software companies). But I believe very strongly in the consumerization of IT – namely the notion that innovation in software is now being driven by consumer applications, and correspondingly by consumers, not by enterprise IT organizations and enterprise software vendors. If you accept this, it means that if you are working on enterprise applications, you also need to be obsessed with the customer experience.

When I think about this abstractly, especially in the context of “software eating the world” or my view that the machines have already taken over and resistance is futile, I completely buy the premise that the consumer experience trumps all technical decisions in any context. Apple has proven this throughout the entire customer experience, including being exposed to the product, buying the product, implementing the product, upgrading the product, and getting help with the product. And I think it’s going to get a lot more important going forward.


Amy and I spent the last week in Tuscany with some friends, including Howard Lindzon. Howard is the CEO of StockTwits, a company we’ve been an investor in for a few years. I was an investor in Howard’s previous company WallStrip, met Howard through an introduction from our mutual friend Fred Wilson (it’s a pretty funny story, as are many things with Howard), and have worked closely together on a bunch of things including TechStars where Howard has been a great mentor and investor since the beginning.

We had an incredibly wonderful week last week and Amy has a great post up on her blog titled Our Revels. If you know Howard, you know he’s an always on, mostly hilarious, sometimes crazy (like a fox), super high energy except when on ambien guy. After four days of Tuscany, Howard was completely chilled out and more relaxed than I’ve ever seen him.

But don’t let this totally chilled out Howard fool you. He was on his computer a lot. Whenever I looked over at him, he was on the Stocktwits web site communicating with the stock community he’s helped create and loves. As the market was gyrating around he tweeted up a storm, put up a bunch of content on StockTwits, did some trades in his hedge fund, and wrote a few insightful (and funny) blog posts about the market including his discovery that the Tuscany VIX is always less than 10.

Howard loves Stocktwits. He loves his business. He loves stocks. He loves the community of people that care about stocks. And he’s creating a company – a really interesting and important one – around his passion. It’s wonderful, infectious, fascinating, exciting, and awesome. And yes, today is adjective day.

While Foundry Group generally avoids investing in vertical markets, we make an exception for our Distribution theme. One of the key attributes of this theme is that the company must be led by an entrepreneur who is completely obsessed with a vertical market. They must be thinking – every single waking moment – about how they are going to change the way the world interacts with the vertical market they are attacking.

Howard defines this type of entrepreneur. It was incredibly inspiring to be around. We had a blast doing non-Stocktwits / non-stock stuff, but when he was working he knew exactly what he was going to work on.

We have either recently closed (but not announced) or are about to close several other investments with entrepreneurs who have similar characteristics. None of them are in our Distribution theme, which is pretty cool, as the entrepreneurs are completely obsessed with the problem their business is addressing.

When an entrepreneur is trying to decide between a couple of different ideas, I often ask the question “which one are you in love with?” If there’s a quick response, then the answer is easy. If the answer is none of them, that’s the answer to which one he should pursue.

Howard reminded me of this again last week. Thanks Howard.


Today is Finance Friday and post #2 has been drafted by the Finance Friday team from University of Chicago Booth and is waiting for my edits. I’m procrastinating so I thought I’d write one of my periodic public service announcement for entrepreneurs. This one is more specific than “ignore the macro economy” – instead, it’s “ignore the Dow and the stock market and get back to work on your business.”

Tom Evslin had a post up this morning titled Don’t Watch The Dow! that caused me to say “right on.” In 1999, 2000, and 2001 I had a my.yahoo.com page up with a bunch of stocks, including a number of companies I was an investor in, as my home page. I’d hit refresh 5,321 times a day, generating plenty of CPM-based revenue for Yahoo. I’ve written about the emotional ups and downs in the past so I won’t repeat myself here other than to say this activity had zero impact on the stock market (I couldn’t do anything about it), it didn’t change my short term decision making (I’m not a trader), and all it resulted in was sucking a huge amount of emotional energy out of me.

When the market went down, I felt sad. When it went up I got the emotional equivalent of a sugar high. When it went back down again, I was bummed. Up – smile. Down – depressed. Up – happy. Down – cranky. And this was all before lunch time. Maybe it was too much coffee or not enough sleep, but it got even worse when the market shifted from 1/8s too 0.01s.

As an entrepreneur, this was all noise. As a long term VC investor, it was also all noise. Sure – the broad cycles had impact, although lots of people disagree on what they actually mean (e.g. do VCs actually benefit long term from down cycles, are the best companies started in recessions when everything is cheaper and more available).

Over time, I’ve learned that none of the short term moves in the stock market matter at all in my life. It’s occasionally entertaining to turn on CNBC and see my friend Paul Kedrosky in the octobox telling all the other people that they don’t actually understand macro-economics, but it’s no different than watching McEnroe when he’s announcing a Nadal – Federer match. It’s just sport.

So – for all the entrepreneurs in my world, take Tom’s great advice. Don’t Watch The Dow! And if you think Scott Kirsner is being sarcastic in his post titled How the players in the innovation economy rationalize away stock market dives, take a deep breath and consider whether the use of the word rationalize is correct or not.

Now, get back to work on something you can have an impact on!


I heard a great phrase the other day: “he’s a 99% committer.” It was in the context of trying to get something to closure where I felt like someone had committed but it was ambiguous. The person ultimately committed and all was good, but there was some question about outcome for a few days. To be clear, I separate this from a process issue – where the person is on board personally but going through an internal process with a partnership, an investment committee, or a decision making group. Rather, I’m focusing on the person who is able to make a unilateral decision, gets 99% of the way there, and then leaves it a little open.

I pride myself on making quick and definitive decisions. However, when I reflected on this phrase, I realize that I’ve played out the 99% committer role a few times in the past year. In each case, I made things more difficult for everyone, including myself, but not simply taking the extra time and energy up front to get to 100%. In one case that I can think of I let things drag on at the 99% point for several months; in another it was only a few weeks. In both cases, I let plenty of extra anxiety build up on my end as I wasted time churning on the 99% decision rather than figuring out what I had to do to get to 100%, running things to ground, and being done one way or the other.

Now, I’m not criticizing the 99% committer – it’s a very effective style for some people as it generates a lot of control and option value in situations. Specifically, from a control perspective, by not fully committing the 99% committer gets to keep playing out things on the edges, poking, prodding, and getting more information. As long as the other party doesn’t disengage, this is effective, although it definitely runs the risk of creating real fatigue on both parties. Furthermore, there is a lot of option value associated with being a 99% committer. You are almost there, but you stall, so the other party feels compelled to give you more information and hold the door open as long as they can.

But this isn’t me. And when I reflect on the few cases where I’ve played the role of a 99% committer, I’m not unhappy with the outcome, but I’m annoyed with my own behavior. By not being a 99% committer, I’m always able to make a decision, deal with the consequences (good or bad), and move on. As a result, the velocity of what I get done is extremely high and I have very little emotional decision backlog stored up.

It’s a great phrase. I expect I’ll use it plenty in the future.


I thought I’d start off father’s day with a tribute to my dad. I’ve learned an amazing amount from him and to this day he’s one of my best friends.

When I was a teenager, I remember a number of Stanley-isms that stuck in my mind. One of my favorites was “if you aren’t standing on the edge you are taking up too much space.” As I type this, I can remember being in my bathroom at home taking a shower thinking about this, which is part of how I remember I first heard it as a teenager.

My dad pushed me, firmly but gently. As a kid I did very well in school, loved to read, and played sports (tennis and then running). When I was 13, I bought my first computer (an Apple II) with my Bar Mitzvah money (and a little help from my dad). I was a typical nerdy, inquisitive teenager – I hung out with “the honors gang” but also liked plenty of time alone to read and explore new things. I sucked at anything mechanical so almost everything I explored was “in my mind.”

Before I could drive (so I must have been 15) my dad introduced me to a patient of his named Gene Scott. Gene had been a technology executive in the 1960’s and 1970’s and – when I met him – was running a technology startup with his son Brian called Scott Instruments. Gene and Brian had created one of the first consumer voice recognition systems – it was called the Scott Instruments VET-2 (for “voice entry terminal” – I think the 2 was because it worked on an Apple II.) Gene was my second mentor (my dad was my first) and he introduced me to the wonders of technology entrepreneurship.

One day when driving home with my dad from lunch in Denton, TX with Gene, I was overflowing with ideas. Gene had given me a VET-2 and I was bringing it home to plug into my Apple II and create all kinds of stuff with it. I’m sure medical dictation was one of them because my dad was always using his business – that of running a thriving endocrinology practice – to give me business and software problems to work on.

I don’t remember exactly what prompted him to say the line, but I remember him saying “if you aren’t standing on the edge you are taking up too much space.” Thirty years later that line continues to be a defining characteristic for how I live my life. I’m constantly pushing, looking for the edge of whatever I do. I’ve internalized this as an endless quest for learning and virtually everything I do is motivated by my desire to learn something new, understand something better, or experience something completely.

Dad – thanks for so many things, but most of all thanks for being my dad!


A decade ago I didn’t pay much attention to the VP of HR position. Today, I view it as a key role if you are growing headcount at least 50% year over year and have more than 20 people in the company. And, title inflation notwithstanding, I prefer to call it “VP of People” since we are people after all, not “human resources” or “HRs”.

Over the past five years, I’ve had the privilege to work with a handful of amazing VPs of People. And, as several of our portfolio companies continue their incredible growth rates, I’ve been involved in recruiting a few new ones to these companies. I have three basic principles for each of them.

1. The VP of People must be part of the executive team and report to the CEO. Many companies that I’ve been involved in have viewed the VP of HR as “key recruiter and HR administrator.” This is not very useful and – in a startup that is growing quickly – dramatically under positions the VP of People as you’ll see in my next principle. If the CEO isn’t willing to have the VP of People on his executive team, I think it’s worth asking the question “why not – aren’t people the most important resource you are adding to your company?”

2. The VP of People is the go to person on the executive team for other executive team members. Every CEO I’ve ever worked with either pays too little attention or too much attention to the dynamics of the people on the executive team. This isn’t just the CEO to VP interactions – it’s the VP to VP interaction dynamics. When VP issues blow up, CEOs often lose huge chunks of time to trying to figure out how to manage through or mitigate the issues. The CEO often becomes camp counselor, parent, therapist, or bitching post. While this is a time sink, it’s also a huge emotional energy drain. The solution – the VP of People is responsible for this. The first stop of any VP – whether it is to talk about issues with another VP or the CEO – should be the VP of People. It’s the VP of People’s job to (a) help everyone work through the issues and (b) summarize what’s going on to the CEO. There will be cases where the CEO needs to get involved, but by having another executive in the mix, it focuses energy on solving the problems, rather than stacking up, or avoiding, issues.

3. The VP of People is responsible for helping everyone on the executive team, including the CEO, level up. Since I believe that life is one big video game, leveling up in your job should be the goal of everyone, especially executives in a company. This used to be called “professional development” but, like “HR”, I think it misses the broader point as I’m not just talking about professional development, but emotional, intellectual, and personal development.  There is no possible way a CEO can focus on this effectively across his team. The VP of People can do this assuming he is on the executive team and is a peer with the other executives.

If you are a CEO of a fast growing company with more than 20 people, do you have a VP of People?


I had several conversations with entrepreneurs this week who were struggling with a specific issue that had plagued them for a while. In each case these are strong, capable entrepreneurs who I’ve known for a long time. As with all entrepreneurs (and humans), they have strengths, weaknesses, and blind spots. In each case, I felt like self-doubt had crept into their brains around the specific weakness they were struggling with.

On the way to the airport, I had call with another entrepreneur that I work with. Same tenor – something that he’s struggled with for a while was causing him to lose confidence. We talked most of the way to the airport and by the end of the conversation, it was clear that, while this is an issue that has been a struggle for a while, it’s one that this person has actually done a good job on, but just has never crushed it. The frustration – over a period of time – started to morph into self doubt.

When I realized this, I gave him some specific suggestions, using the frame of reference of “inquiry.” This is how I deal with my own self doubt. Whenever I find myself struggling with something that I think is important, I go on an inquiry to learn as much as I can about the issue, figure out what I’m struggling with, figure out a solution that works for me, and then implement it. I’ve done this numerous times in my life – sometimes the inquiries are short (24 hours); other times they last a decade or more.

When I thought about what might be generating this self doubt in otherwise successful, smart, and intellectually / emotionally strong people, I realized that the context that we are in is often a driver. Suddenly lots of companies are having what appears to be success and rapid growth. If you are an entrepreneur and you are not running one of these, even if you are experienced and successful, it’s easily to start to doubt yourself. This is especially true when you find yourself in a bumpy spot in your business.

Perspective matters a lot at these moments. I’ve had a lot of successes and failures. Whenever I fail at something, I just get up, try to learn something from it, and try again. But I don’t benchmark myself against others – I don’t care where I am on any particular list, I don’t care what other people are saying, I don’t care what is written about me (good or bad). I just try to learn from each experience and get better. And, when I realize that I’m doubting my ability to do something, I double down on the notion of figuring it out and use an inquiry to get me there.