Brad Feld

Category: Entrepreneurship

Seeking Alpha has started a new interview series on their site.  Dick Costolo – the CEO of FeedBurner – has an excellent one up.  Seeking Alpha readers have a window to ask questions online and then Dick (or the interviewee) answers them.  Dick’s interview is a superb window into the mind of the brilliant, creative, and often hilarious guy running FeedBurner and writing the Ask the Wizard blog.  It’s not quite Being John Malkovich but close.


Every great investor has made some investments that he wishes he’d never made.  Occasionally he’ll make another one like it.  And another one like it.  Eventually you learn.  Or maybe you don’t.

I heard the following quote today attributed to an extraordinary successful investor (I’ve editorialized a little.)

“I’m fascinated with airplanes and the airline business, but every time I invest in them I regret it and lose money.  I finally set up an 800 number, and every time I feel like buying an airline I call it, and it is a recording of me, telling me not to do it.” 

There are several areas that I’ll never invest in again.  Maybe someone can make money in them, but I can’t.  And I eventually learn.  Time to go set up a few 800 numbers to remind me.


I had a long phone call with a CEO of a company on Friday.  He’s had an intense few weeks and was clearly stressed out.  His summary was “my stomach hurts.”  My objective view of his business is that it’s fine – lots of things are going well – but there are plenty of issues he needs to address and they don’t necessarily have a short term time horizon for resolution.

This reminded me of a question I received from another friend a few months ago:

I thought of you yesterday as I was speaking with a new business acquaintance.  She was telling me about all her new business ventures, including a talk show concept. She has already made a connection with an industry source who is helping her fine tune and sell it. As I congratulated her on the progress she’s made, she said, “This is so new to me. I try to listen to my gut instincts, but the fear gets in the way.”  Assuming that your entrepreneurs (particularly first-time entrepreneurs) are aware of at least some of the risks involved with starting any company, do you ever have to advise them how to manage their fear so it doesn’t get in the way of their potential success?

I have long believed that fear, anxiety, and guilt are useless emotions in an entrepreneurial context.  When I get into an existential discussion with some people about this, they argue that there are contexts where these are useful emotions, but I still haven’t found them.  So – my first advice is “let go of the fear and anxiety (and guilt) – immediately.” 

In my first company I was an anxious entrepreneur.  I felt the full burden of the business and even though I had a great business partner, I internalized all the ups and downs of the business.  I pushed through the anxiety regularly, which I imagine impacted my current style (which I like to think of as intense/playful) – much of which was forged from my experience with my first company and some of my big successes and failures from the 1998 – 2002 time frame.

“Letting go of fear and anxiety” isn’t trivial – nor is it automatic – but it can be done.  During my Friday afternoon CEO conversation, my friend acknowledged that he wasn’t panicked, but he felt close.  It was clear he was physically and mentally exhausted from the effort he was putting into his company.

When I’m tired, things go to hell.  My first indicator is that when something good happens I feel happy and when something bad happens I feel unhappy.  I used to just accept this as part of my reality – now I know this means I need a break.  Sometimes it’s just a weekend; other times it’s a week.

“Fear is the mindkiller” is my favorite quote from Dune (one of the all time greatest sci-fi books.)  Fear – at least for me in an entrepreneurial context – almost always comes from fatigue.  It’s really difficult to rationally address the issues that cause you fear when you are tired – which just makes the cycle more difficult.

I told my friend to take the weekend off.  He should turn off his computer, don’t try to “catch up on email”, don’t try to “fix anything, let the thoughts about his business roll through his head, but spend time with himself and his wife.  And sleep.  As much as he wanted to (I got up at 10:24am this morning.)  On Monday, he should come back refreshed, not anxious, and ready to address the issues that he’s facing.

Remember that fear is the mindkiller.


It seems like there’s a regular rhythm to the magnitude of “great posts from entrepreneurs and VCs” – Wednesday is the magic day.  I woke up to a bunch of great stuff in FeedDemon – including:

  • Dick Costolo (FeedBurner) on Legal Fees: Start Swearing Now – Dick’s views of lawyers.
  • Matt Blumberg (Return Path) on Highs and Lows, Part II – Once you get big enough, you get to share the “high/low whiplash” with others on your leadership team.
  • Matt McCall (Portage Ventures) on Using Scorecards with Your Board – report early and consistently.
  • Josh Kopelman (First Round) on Do You Need to Switch Your Pitch – what type of pitch should you use when presenting to new potential investors?

The sun is up, Camden Yards is out my window, I had a great run, and it’s time for another day.


Reuters had an article out today titled US reaches visa cap, skilled workers out of luckAs someone who is constantly trying to recruit great software developers for companies I’m an investor in, this is an insane situation.

The US Immigration Service apparently “reached its annual quota for visa applications in one day.”  The article summarizes the situation:

“The Citizenship and Immigration Services received a record of more than 150,000 applications for the H-1B visa on Monday, nearly double the number of visas it can grant for the fiscal year beginning October 1, 2007. Individuals cannot apply for the visa. The employer must apply or submit a petition on the worker’s behalf. The visa is good for up to six years. The government will grant 65,000 visas to those who hold the equivalent of an undergraduate degree and possess the technical expertise in a specialized field, such as engineering and computer programming. Another 20,000 visas will go to people with advanced academic degrees who have technical expertise.”

There is just no reason why there should be a quota on this type of H-1B visa.  I don’t want to delve into the more generic immigration policy issue, but we are talking about highly educated employees in a segment that is seriously supply constrained, especially if you believe anything about demand over the next 10 years.  One of the main reasons I’ve been as involved as I have been in the National Center for Women & Information Technology is because I believe that we don’t have enough qualified software developers in the US and one way to solve for this is to get more women interested.  

It certainly doesn’t help when the government artificially constrains the supply of H-1B visa, especially from people that are already employed.  Maybe a few of our presidential candidates gearing up for a 2008 run will understand this issue.


I’m a huge Warren Buffett fan and have been for as long as I can remember.  Buffett has recently posted his annual blog post (also known as the Berkshire Hathaway’s 2006 Chairman’s Letter (thanks Alex for the pointer that it is up on the web.)  It should be required reading for anyone in any business.


Dick Costolo, the CEO of FeedBurner, has another awesome post up titled Too Many Companies?? 

He starts with the observation:

“There aren’t “too many companies in the market right now”. Even if there are 90,000 more companies, there still aren’t too many companies. Neither is there too much capital or too little capital or not enough engineers in this market. There are only specific market forces that you should weigh vis-a-vis your specific company.”

and ends with the conclusion:

“The key is to just get on the bike, and the key to getting on the bike is not the confidence in knowing you will be successful if you do x,y,z. The key to getting on the bike is to stop thinking about “there are a bunch of reasons i might fall off” and just hop on and peddle the damned thing. You can pick up a map, a tire pump, and better footwear along the way.”


Jason Wood has an interesting post up titled Failure: Can fearing it impede professional greatness?  It’s consistent with the title of his blog (The Ponderings of Woodrow) – really good ponderings on failure here.


Business 2.0 has a good article titled A startup’s best friend? Failureon how to succeed by paying attention and responding to failure.  Dogster, Google, and Riya (Like.com) are profiled.  I got plenty of chuckles after I made an investment in Dogster.  I look forward to the day when I can say “look who’s barking now.”