When to change careers (for Fred Wilson)

Fred Wilson is wondering when to quit being a VC:

I was thinking about going out on top. So few manage to do it. Shaq is warming the bench in Boston. Brett Favre should have called it quits after he threw the pick in OT against the Saints. The Stones haven’t written a great song in thirty years. The money and the burning desire to “win another one” drives the great ones to stick around too long.

I also look around the venture capital business and I see investors who were at the top of their games in the 90s struggling to remain relevant. And I think about how I want to manage this issue myself.

  1. “Hanging up your cleats” as in “retire” is wrong way to talk about a career change
  2. Career change should be driven by internal issues (barring medical reasons, i.e sports injuries; economic, see the hollowing out of US manufacturing base )
  3. Instead of being “pushed out” look for reasons to be “pulled out” of the current career. Create a passionate interest elsewhere
  4. My rule is every new job must have 50% new things to learn.
  5. The best career is one where you are *bad* at it but *love* to do it.
  6. Variety is key. Voluntary career change is good because it is different
  7. Don’t use outside metrics internally. Internal motivation is what counts the most, not anyone else’s opinion.
  8. Stephan Covey’s statement applies “If you are green you are growing if you are ripe you are rotten”.

I have found no VCs interested in Amplafi, but every prospect that I talk to is interested. The prospects have experienced the problem personally and the VCs haven’t. The prospects can overcome my pitch’s weaknesses.

I think those VCs who have lost their edge need to do something completely different to get a completely new perspective on something outside their current fields.

Some suggestions for Fred:

  • Start your own small business. Start a Subway franchise and work personally at it using funding it with no more than franchise fee plus minimum capital. Go through the bank loan process and artifically diminish your assets for loan purposes to experience the hassles. See what the problems are there for small business owner. Run this business personally for a year taking no additional capital. Just really get into this as if it was the way you were going to make it.
  • Change people’s behavior and thoughts about the social contract of owing taxes

    Spend time and focused money people understand the tax structure. It would take relatively little money to help get local tax measures passed so that our government could function? Don’t focus on the state issues go ultra local so you can understand the issues.

    For example, here in SF the taxes are used to build stuff but no taxes are supplied to run things. The result is Caltrain ( SF Bay Area commuter train ) is in danger of shutdown. A primary cause is that poorly designed BART extensions are draining operating capital from the agencies that also fund Caltrain. Maybe in your area things are too expensive to influence, but what about in other areas?

  • You are passionate about education. Sometimes technology is the anti-solution. Right now, the US despises teachers and educators. The unions are held up as this evil menace. But every teacher I know is there because she (still mostly women) cares. They work long hours just to handle the current class. This leaves little time for self improvement.

    Create and personally run a company that:

    • that frees up the teacher hours.
    • Maybe better grading systems?
    • Find time wasters in the classroom that keep teachers from being able to execute. Stay away from attacks on “evil bureaucrats” How about what Intuit did for checkbooks? Intuit didn’t blame the evil checkbook, they just made the task of managing the checkbook easier.
    • enables teachers to share best practices without being judged.
    • Preferably services that a teacher could use without having to persuade the school or district to buy-in.
    • Teachers need CPE hours maybe leverage that point?

    Make the case for education in the Deep South and the rest of the nation.

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