Brad Feld

Month: June 2016

On Tuesday, Jerry Colonna and I had a fireside chat hosted by the Blackstone Entrepreneurs Network titled Making Mental Health a Priority. We did it at DU in partnership with Project X-ITE and had a powerful afternoon.

Last night I had dinner with a CEO I like a lot where we talked about some of the things he was struggling with. I used a concept with him that I’d been mulling about and tried out publicly at the event with Jerry.

I call it the responsibility glitch.

It’s a glitch I’ve had, and have struggled with, since I was a teenager. It’s also a glitch I see in many founders and CEOs.

I started my first company when I was 19 years old. By that point I felt immense responsibility for what I did. I was at MIT working hard on school. I had spent the previous two years – part time during the school year and full time in the summer – writing software for a company called PetCom. One of the products I wrote for them (PCEconomics) was very popular in the oil and gas industry and sold a lot of copies. I got a 5% royalty on every copy sold so I was getting monthly royalty checks ranging from $1,000 to $10,000 (I think the largest one I got was just over $12,000.) I had a long distance relationship with my high school girlfriend who became my first wife. I was the treasurer of my fraternity. While I had an adequate amount of fun in college, I was very serious. And responsible.

As I drifted into my 20s, as my first business grew, I felt responsible for many things around it. I got married and felt responsible for the relationship, my wife, and her actions. I was in a Ph.D. program and felt responsible for the work I was doing there.

At some point, the glitch appeared. It was likely stimulated by a variety of things, including too much overall feeling of responsibility and no perspective on how to manage or modulate it. I had clinical OCD (although I didn’t know it at the time) and had a need to try to control everything in my environment, although my attempts to do this were often hugely irrational and often entertaining to others. For example, I came up with the notion that if every cigarette butt that I passed on the sidewalks in Massachusetts wasn’t parallel to the street then my mother would die. While I clearly had plenty of spare cycles in my brain to ponder stuff like this, the image of me wandering down the sidewalk straightening cigarettes with my sneakers still causes me to cringe even 30 years later.

Then my circuits overloaded. I got kicked out of the Ph.D. program. My wife had an affair and we ended up getting divorced. My business was fine, but the stress from it, and everything else around me was overwhelming. I suddenly started feeling responsible for things I had no business feeling responsible for. I worried about my ex-Ph.D. colleagues, how they were doing, and wondered what I could do to help them avoid my fate. I was empathetic to my ex-wife when she called to ask for help when she was having problems with her boyfriend. I felt responsible for every client we had and whatever flaws were in our software and every moment.

I felt too responsible.

This eventually overwhelmed me and was part of what trigged my first depressive episode which lasted two years. Fortunately I was in therapy so I had a good solid two years to explore the feeling of being deeply depressed and all the elements around it. While there was no joy in that, it was profoundly important to my character and who I am today.

One of the things I learned about myself during this journey was that by being too responsible, I caused a number of unintended negative side effects. Some of these were easy to identify. For example, I learned that I undermined the people working for me since I allowed them to be less responsible, since I’d overcompensate for them. I realized that I was spending a lot of energy trying to control exogenous forces that I had no influence on. As I understood and resolved my OCD, I figured out that I was exhausting part of myself by continually processing a bunch of irrelevant linkages between things that either didn’t need to be controlled, or that I had no ability to impact.

Over the last 25 years, I’ve seen many other founders and CEOs be in the trap of feeling too much responsibility. Their instantiation of this occurs in different ways. There are often elements that are powerful for short moments of time, especially in a crisis. But when the behavior persists, crazy shit starts to happen. Often, feeling too much responsibility is a destructive force to the people around the founder / CEO, the company, the founder / CEO’s family, or the founder / CEO herself.

When I’m sitting with a CEO who feels anxious or self-identifies as depressed, even when she can’t really articulate why or what it means, I often look for the feeling of being overly responsible. It’s common and comes out quickly. When I dig in, I often find the person feels responsible for everyone and everything around her except for herself. She comes last in the list and rarely even gets to herself.

This is the responsibility glitch. If you identify with this, I encourage you to be aware of two things. First, be responsible, but try to stay on the right side of the “too much” line. This is different for everyone, but there definitely is a line where your feeling of responsibility starts to become destructive.

More importantly, be responsible for yourself first. As Jerry likes to say, go on a continuous journey of radical self-inquiry. Understand yourself. Learn about yourself. Take care of yourself. Be responsible for yourself. Only then can you be constructively responsible for others and things around you.

And now it is time to go for a run.


Yesterday Hillary Clinton announced her Initiative on Technology & Innovation at Galvanize in Denver. I skimmed it quickly and was pleased with how substantive it was. I pondered what Trump’s equivalent would be and decided it is likely to be a tweet that says “Technology loves me.” Fred Wilson had a more constructive suggestion this morning, where he listed out the specific topics he felt were important to address and said that Hillary has now weighed in on them and he’d like to see Trump do the same.

I just read Hillary’s briefing carefully to understand what I agreed with, disagreed with, and thought needed more fleshing out. I didn’t fundamentally disagree with anything and was delighted to see a number of the initiatives I’ve been working on included. Regular readers of this blog will see lots of congruency with my efforts around National Center for Woman and Information Technology, Startup CommunitiesStartup Visa, Global EIR Coalition, Techstars Foundation, Net Neutrality, Open Internet, and Patent Reform.

Similar to my post yesterday on the agenda for the The Center for American Entrepreneurship I’m going to list the outline of the initiatives as an easily accessible overview. If this topic is interesting to you, it’s worth spending ten minutes and reading the full text of the Hillary Clinton Initiative on Technology & Innovation. And, in all seriousness, I hope Donald Trump puts out something similar so we can compare them.


Building the Tech Economy on Main Street

  • Invest in Computer Science and STEM Education
  • Building the Human Talent Pipeline for 21st Century Jobs
  • Increase Access to Capital for Growth-Oriented Small Businesses and Startups, with a Focus on Minority, Women, and Young Entrepreneurs
  • Attract and Retain the Top Talent from Around the World
  • Invest in Science and Technology R&D and Make Tech Transfer Easier
  • Ensure Benefits are Flexible, Portable, and Comprehensive as Work Changes

Investing In World-Class Digital Infrastructure

  • Close the Digital Divide
  • Launch a “Model Digital Communities” Grant Program
  • Connect More Anchor Institutions to High-Speed Internet
  • Deploy 5G Wireless and Next Generation Wireless Systems

Advancing America’s Global Leadership in Tech & Innovation

  • Fight for an Open Internet Abroad
  • Promote Multi-Stakeholder Internet Governance
  • Grow American Technology Exports
  • Promote Cyber-Security at Home and Abroad
  • Safeguard the Free Flow of Information Across Boarders
  • Update Procedures Concerning Cross-Border Requests for Data by Law Enforcement

Setting Rules of the Road to Promote Innovation While Protecting Privacy

  • Reduce Barriers to Entry and Promote Healthy Competition
  • Defend Net Neutrality
  • Improve the Patent System to Reward Innovators
  • Effective Copyright Policy
  • Commercial Data Privacy
  • Protect Online Privacy as well as Security

Smarter and More Innovative Government

  • Make Government Simpler and More User Friendly
  • Open up More Government Data for Public Uses
  • Harden Federal Networks to Improve Cybersecurity
  • Facilitate Citizen Engagement in Government Innovation
  • Use Technology to Improve Outcomes and Drive Government Accountability

A few weeks ago I had lunch with John Dearie to discuss a new non-profit he has started called The Center for American Entrepreneurship. Several friends and people I respect a lot are on the board, including Lucy Sanders (NCWIT), Troy Henikoff (Techstars Chicago), Bob Litan (Brookings Institute), Rebecca Lovell (Seattle’s Office of Economic Development), Monisha Merchant (formerly Senator Bennet’s Economic Advisor), Jonathan Ortmans (Global Entrepreneurship Network), Jason Seats (Techstars), Dane Stangler (Kauffman Foundation), and Vivek Wadhwa (Stanford).

When I know, work with, and respect more than 50% of the board of a new non-profit, I pay attention. I’m glad I did – the conversation with John was stimulating. He has a vision and the experience to create a non-partisan organization to engage and educate people, especially policymakers in government, regarding the critical importance of entrepreneurs and startups to innovation, economic growth, and job creation.

While that might sound like a mouthful, I’ve been railing against the limitations of the way our government thinks about entrepreneurship for a decade. I’ve had a number of meetings over the years with the Small Business Administration (SBA) whose name says it all. I’ve often encouraged them to rename themselves the High Growth Entrepreneurship Administration, or even to create a separate organization, or split the SBA in two, or, in a fit of libertarianism, eliminate the SBA altogether. But, I know that none of that is going to happen because of a number of factors, including the fundamental lack of understanding in government about the difference between small business and high growth entrepreneurial businesses. Oh, and inertia.

Over the last few years, I’ve been exploring the idea that we really have two types of small businesses: local businesses and startup businesses. Both are important, but they have very different needs and contribute to the fabric of our economy in very different ways. As John and I were talking, he slid his book, Where The Jobs Are: Entrepreneurship and the Soul of the American Economy, across the table to me. I turned the pages and then over the weekend I read it while laying on the couch after a run.

It’s a great book that every policy maker in government at any level should read. It’s the first book I’ve seen that lays out an effective set of policy recommendations, with substantiation, for the startup society that we are living in. Against the backdrop of total government confusion about economic growth dynamics, combined with endless shallow rhetoric about what to do, I found it to be refreshingly optimistic.

While The Center For American Entrepreneurship website has a series of pages describing the issues and solutions to them, I didn’t find a crisp summary of the book on the web. So I decided to create an outline of the policies and the recommendations. They follow. If you disagree with any, or have any to add, please toss them in the comments as I evolve this as a list of “ways government can help startup communities.”


“Not Enough People with the Skills We Need”

  • Incentivize STEM Education
  • Launch a Curriculum-Focused Dialogue Between Business and Education
  • Launch an Education Reform Dialogue Among America’s Educators
  • Incentivize Experienced Talent to Consider Joining Growing Startups

“Our Immigration Policies Are Insane”

  • Eliminate the Cap on H-1B Visas
  • Award “Graduation” Green Cards
  • Create a “High-Skill Immigrant” Green Card
  • Create a “Startup Visa”
  • Create CitizenCorps

“Not All Good Ideas Get Funded Anymore”

  • Make the SBA More Entrepreneur-Friendly
  • Incentivize the Formation and Commitment of Angel Capital
  • Fix Venture Capital by Fixing the IPO Market
  • Cultivate the Formation of Viable New Businesses
  • Increase Startups Access to Capital
  • Enhance the Science and Technology Capacity of the U.S. Workforce

“Regulations Are Killing Us”

  • Devise a Preferential Regulatory Framework for New Business
  • Require Third-Party Review of All Proposed Regulations
  • Create a Regulatory Improvement Commission
  • Rank States’ Regulatory Environment

“Tax Payments Can Be the Difference between Survival and Failure”

  • Establish a Preferential Tax Framework for New Businesses
  • Allow Cash Method of Accounting for the First Five Years
  • Allow 100 Percent Expensing of Business Investment for the First Five Years
  • Pass the Startup Innovation Credit Act

“There’s Too Much Uncertainty – and It’s Washington’s Fault

  • Gradually But Significantly Reduce the Federal Budget Deficit and National Debt
  • Enact Comprehensive Competitiveness-Enhancing Tax Reform
  • Increase the Research and Development Tax Credit – and Make It Permanent
  • Return Federal Funding of R&D to 2 Percent of GDP
  • Jump-Start America’s Trade Agenda
  • Negotiate a U.S.-China Free Trade Agreement
  • Combine and Modernize Unemployment Insurance and Trade Adjustment Assistance

Unlike the person with a similar slogan, this one is highly accurate. Sanebox does indeed make email great again.

I’ve been using email since 1983. I started with MH and Rmail, then cc:Mail, then Microsoft Mail, with Compuserve mixed in. Eventually I ended up using Pine for non-Windows stuff and Outlook for Windows stuff. For a while. About seven years ago I switched to Gmail and never looked back.

Over the last seven years, I’ve tried a bunch of different add-ons and plug-ins and whatever you want to call them to try to clean up my inbox. As investors in Postini, I was able to eliminate my spam problem early on. But I struggled endlessly with bacn. I get 500+ emails a day so the bacn is intolerable in my main email flow and ends up getting ignored, rather than read later.

So I’d go through weeks of unsubscribe fits, where I’d try to mash out my misery by unsubscribing to things I didn’t want. Often, this just resulted in more bacn, sometimes from the same senders but often from others. I once again would go through another cycle where I’d try a different unsubscribe tool, but I’d always end up with better, but not good enough.

Over Memorial Day weekend, I decided to try Sanebox. My partner Seth has used it for a while and several other people I know swear by it. I tried it when it first came out (as one of my endless efforts to tame my inbox) but it didn’t satisfy me then.

This time – about a month later – I can definitively state that Sanebox is awesome. Not sort of awesome. Extremely awesome. It should consider running for president.

Magic trick #1: @SaneBlackHole: If I want to never see a piece of bacn again, I just label it @SaneBlackHole by typing v<downarrow><enter>. Gone, forever. Anything from the sender never ever shows up in my inbox again, kind of like how Ramsay Bolton will never show up in Game of Thrones again.

Magic trick #2: @SaneNotSpam: I trust Gmail’s spam filter so I never, ever look in my spam folder. But Sanebox does look there for me because it knows not to trust it as much as I do. It finds at least one piece of NotSpam every day – sometimes as many as five pieces. Some of the NotSpam is amazing – on Friday a distribution notice from a VC fund I’m an investor in showed up there.

Magic trick #3: @SaneLater and @SaneNews: Sanebox automagically figures out which things I can look at later. It also figures out which email is a newsletter of some sort. It’s easy to adjust these if it gets it wrong, or label an email in my inbox with one of these labels and it then becomes one of these forevermore. At least 20% of my daily email ends up in one of these folders which I can then process once a day.

Within 30 days, with almost no effort, the signal in my inbox has reached about 99%. I read through notifications and news once a day. The crap that I don’t really want shows up once in SaneLater or SaneNews, I relabel it SaneBlackHole, and it’s gone forever.

Suddenly, my inbox is remarkably clean, useful, and free of noise. Thanks Sanebox!


It’s 2am on Friday and I’m awake because Brooks the Wonder Dog is afraid of thunderstorms. His approach to them is to literally try to climb under my body while I’m sleeping, which prevents me from sleeping, which results in me watching the Brexit insanity in real time.

Yesterday, we had our own US insanity around immigration as our Supreme Court voted 4-4 on the legality of Obama’s executive orders on immigration. This means that the issue gets kicked back down to the lower court and nothing is likely going to happen on this until after the election. There are so many ironies in this, especially against the backdrop of the potential immigration implications in England of the Brexit, that one can only wonder if our politicians are taking Game of Thrones a little too literally.

It’s easy to view all of this abstractly, rather than think about how it impacts individual people. Two weeks ago I watched a movie by Rishi Bhilawadikar titled For Here or To Go? It was about a set of Indian software developers in the US on H1-B visas. The main character wanted to start a company, or join a startup, but couldn’t make either happen in the context of the current H1-B visa constraints.

Now, this wasn’t a dry movie. While I don’t know Indian culture very well, Rishi created a rich set of characters, interwoven storylines, and a powerful content – including the challenge of romantic relationships while having an uncertain future around one’s immigration status – that drew me in to the movie.

There were several big twists, including the challenges of a large company co-founded by two Indian immigrants, one who was frustrated with the US immigration system and wanted highly educated Indians in the US to go back to India and start their companies there. This intersected with the main character’s romantic relationship and job search, which came together at the end in a powerful way.

Rishi is planning on formally releasing the movie at the beginning of next year. I’ve offered to help, and – like I did with Code: Debugging the Gender Gap – am providing some financing for that effort. If you care about the immigration issue and want to help with the movie in some way, email me and I’ll get you set up with a free full preview screening of the movie so you can watch it and decide if you want to get more involved.


This cliche, which has uncertain attribution (Winston Churchill, Rahm Emmanuel, M. F. Weiner) is a priceless line that gets tossed out periodically, especially in the middle of a crisis.

Over the years I’ve been involved in many business crises. I qualify this, since my crises have never involved life and death or the survival of the human race. But they are still crises. Some have lasted moments while others have lasted months, and I can think of one that went on for three years – or at least took three years to dig out of.

I’ve only occasionally been in the CEO (or equivalent) role during a crisis. Most of the time I’m a board member or investor. As a result, I’ve participated in dealing with the crisis, but I’ve also been able to observe the behavior of the leader during the crisis. While I’ve had to go throw up in the bathroom after a particularly distressing conference call more than once, I’ve been fortunate to be able to be one level removed from the essence of the crisis.

A typical leader has a natural tendency is to be defensive in the face of a crisis. The first reaction is to blame someone – or something – else. Often the blame is aimed at something abstract or non-controllable, which often has nothing to do with the crisis, but is adjacent to whatever is going on so it’s an easy target. As soon as the blame is out there, the attack begins, which often causes others to be defensive, generating a vicious cycle of anger, hostility, frustration, and obfuscation at the beginning of the crisis.

Over time, I’ve learned that the best leaders take a completely different approach. When the crisis erupts, rather than immediately go into action, she pauses and takes a deep breath. She starts collecting data about what is happening. In parallel, she communicates the crisis to the key people who need to be involved – the board, the leadership team, and anyone specifically engaged in the crisis.

If the crisis lasts moments, rapid action is critical. But if it’s simply the beginning of a broader issue, especially one where the root cause isn’t known yet, the worst thing a leader can do is act immediately. As a teenager, my dad taught me about the idea of unintended consequences and I’ve had the experience, and how to deal with it, pounded into my soul over the years.

If you want to understand this better, I encourage you to read Charles Perrow’s classic book from 1984 – Normal Accidents: Living with High Risk Technologies. I often forget to mention it when asked which books have influenced me the most – Normal Accidents is in the top 10.

So, you are now in the crisis. As CEO, you feel an immense need to address whatever is causing the crisis and resolve it. But that’s only half of it. If all you do is focus on solving the crisis, you are missing the big opportunity, which is to learn from it and integrate it into the fabric of your company. It’s not that you won’t ever have a crisis again – you most certainly will. But if you can change the way your company functions in the context of a crisis in a positive way, you can actually get some value out of the crisis.

Don’t forget to breathe.


Jerry Colonna and I are having a fireside chat and Q&A about leadership and mental health on Tuesday, June 28th at 3pm at The Josef Korbel School for International Studies. It is being co-hosted by Blackstone Entrepreneurs Network and DU’s Project X-ite. Please register and join us.


By definition, as a company scales rapidly, it adds people quickly. There are many things about this that are difficult, but a vexing one has to do with the leadership team.

Often times, the wrong people are in senior positions. The faster a company grows, or the less experienced the CEO is (e.g. a first time founding CEO), the more likely it is a problem. Per Fred Wilson’s famous post What A CEO Doesthis is one of the three key responsibilities of a CEO.

“A CEO does only three things. Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Makes sure there is always enough cash in the bank.”

I’ve slightly modified in my brain to be that a great CEO has to do three things well. These three things. They can be great at many other things, but if they don’t do these three well, they won’t be successful long term.

Let’s focus on “recruits, hires, and retains the very best talent for the company.” This is where the vexing part comes in. As a company grows from 25 to 50 to 100 to 200 to 500 to 1000 people, the characteristics of who is the very best talent in leadership roles will change. It’s rarely the case that your leadership team at 1000 people is the same leadership team you had a 25 people. However, the CEO is often the same person, especially if it’s a founder.

Stress on fast growing companies comes from a lot of different places. The one that is often the largest, and creates the most second order issues, is the composition of the leadership team. More specifically, it’s specific people on the leadership who don’t have the scale experience their role requires at a particular moment in time.

Take a simple example. Imagine a 50 person company. Now, consider a VP Engineering who has never worked in a company smaller than 5,000 people. His last job was VP Engineering on top of a division representing 25% of the development resources of a very large company, reporting up to the division president. By definition he has never worked in a company that grew from 50 people to 100 people in a 12-month period. He might argue that he’s seen that kind of growth within a segment of the company, but he’s never experienced it working directly for a CEO of a small, rapidly growing company.

In comparison, consider a VP of Engineering who has worked in three different  companies. She started with one that grew from 20 to 200 and was acquired. The next one grew from 5 to 100 and then shrunk again to 10 before being acquired. The one you are recruiting her from grew from 100 to 1000 while she was in the role and is still going, but she’s now tired of the larger company dynamic and wants to get back to a smaller, fast growing company.

Which one sounds like a better fit? I hope you chose the second one – she’s a much better fit in my book.

Now, here’s the magic trick – if you are a CEO who is interviewing for a new member of your leadership team, ask the person you are interviewing if they have every been in the same role as a company that grew from size -50% to +200% of yours. So if you are the CEO of the 50 person company, you are looking for someone who has been in at least one company that grew from 25 to 100 people. Ideally, they participated in growth to a much larger scale, but at a minimum they should bracket these numbers.

Now, ask her to tell you the story of the company, the growth experience, how she built and managed her team, and how she interacted with the rest of the team. Keep digging into the dynamics she had with the CEO, with other executives, and with the people who worked for her. Focus a lot on a size you will be in a year so you know how she’s going to handle what’s in front of her.

Remember – you are looking for competence fit and culture fit. By using this approach, you are exploring both, in your current and near term context.


Yesterday was not an awesome day.

I was tired from my run on Saturday and a late-ish night so I slept in. Amy got up with the dogs. When I woke up, our country was deep in the fallout from the worst mass shooting in the history of the U.S. I was shocked by the shooting, then angry about some of the responses, and then ultimately – with Amy – just sad about the whole thing. Love is so much more powerful than hate, and there is so much hate in the world right now.

So I went for a long run. That didn’t help much so I took a nap and laid down on the couch and read the book at the top of my pile of infinite books. Other than being with Amy and seeing Mark Pincus and Dick Costolo in a cameo on Silicon Valley, reading The Curve was the best part of my day.

Jeremy Blachman, the co-author, wrote a book a decade ago called Anonymous Lawyer which I loved. It almost inspired me and my partner Jason to write a book titled Anonymous VC, but Jason decided to make the video I’m a VC instead. Jeremy sent me an advanced reader copy (ARC in the book trade) of The Curve so my simple task was to read it.

I enjoyed it a lot. I’m not a lawyer, but I’m surrounded by them (Jason used to be a lawyer and some of his best friends are lawyers). I didn’t go to law school but I’ve become very involved at CU Law and Silicon Flatirons around their entrepreneurship initiatives (Phil Weiser and Brad Bernthal are close friends.) I’m not deeply involved in politics, but about 25% of the people I interact with in politics went to law school.

The Curve is a super snarky take on law school. It chronicles the year of a fictional law school in New York – one at the bottom of the barrel. One of the protagonists is a first year law school teacher who quit his job as a high powered New York corporate lawyer to achieve more meaning in his life. The cliche “be careful what you wish for” comes immediately to mind.

It’s a fun, quick read. I enjoyed the dramatic twists, the sarcasm, and the characters, especially as the book cranked into the second half. Once it hit it’s full speed around page 100, there was no stopping it.

If you are a lawyer, or a law school student, or just know a bunch of lawyers and law school students, this book is for you.

And … this just in. Microsoft to buy LinkedIn for $26.2 billion. Nice job on the marathon Reid and Jeff!