Saluting The 'Misses'

As the market chasing has come back in vogue and ‘return envy ’ is back, I wanted to take a few minutes to salute my mistakes and misses. There are some doozies.

I have major ‘return envy’ these days. In 2008, things were easy. I was out of the market and having a big hedge fund year. I was investing in web start-ups and buying a few stocks when the VIX was 90. Soren and I started Stocktwits in October, 2008. To borrow from a baseball analogy…’The Ball Looked FAT’.

In 2009, I worked 24 hours/day and missed a 60 percent stock market year. The individua misses were right in front of me… Apple $AAPL , Google $GOOG , Priceline $PCLN, Coffee $GMCR….oy.

In 2010, I am just plain confused. Biotech, social gaming and geo-location are in, three areas of zero interest and investment for me. There is ‘hot money’ back in the stock market and hot deals in venture land .

In the last few years I have managed to pass on the following very early financings:

1. Twitter
2. Zynga
3. Foursquare

It has gotten so bad that entrepreneurs feel good about being passed over by me. I heard one of the entrepreneurs at ‘Y Combinator’ say to another:

‘If Lindzon passes….we are a lock!’

For the moment, I am the Cliff Claven of angel investing, but as a long-time stock market participant, I know that it’s mostly about ‘misses’. You need to stay in the game so you can keep swinging and do whatever you can to stay in the flow.

This week I tried to stay in the flow by attending Y Combinator and helping Tech Stars in their selection process.

While I may be cold, I know that the people who I consider my true competitors were not in the room, and have not been in these rooms for a long time.

Missing is part of the long process of winning.

38 comments

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  2. faithmight says:

    It’s hard to be every woman! Plus, the market is always going to be there. You miss some but as long as you stay in the market you’ll always catch the next move. I’m sure your presence at YC had some folks take notice. Thanks for sharing!

  3. faithmight says:

    It's hard to be every woman! Plus, the market is always going to be there. You miss some but as long as you stay in the market you'll always catch the next move. I'm sure your presence at YC had some folks take notice. Thanks for sharing!

  4. julie_poplawski says:

    Thanks Howard! Good words. There’s that batting average analogy people always say that feels conciliatory, yet you do have to stay in the game to play. Gatta get up check in and make it happen!

  5. julie_poplawski says:

    Thanks Howard! Good words. There's that batting average analogy people always say that feels conciliatory, yet you do have to stay in the game to play. Gatta get up check in and make it happen!

  6. Gina Smith says:

    Howard, you never left the game it was always in ur mind and heart. When we see your name or walk in a room and there you are, we can only say he’s a man with great accomplishments. We can all be honored to be in your presence.

  7. Gina Smith says:

    Howard, you never left the game it was always in ur mind and heart. When we see your name or walk in a room and there you are, we can only say he's a man with great accomplishments. We can all be honored to be in your presence.

  8. Mr. Tuxedo says:

    What current information do you have on quantum cryptology and is there a stock that has the inside track?
    I have some shallow thoughts.

  9. Dave Pinsen says:

    You’re modest, but you’ve crushed it as an angel investor, and you’re a successful serial entrepreneur to boot. If I were you, I’d be tempted to take my money out of the stock market and just invest it in more start-ups (your own and those of other entrepreneurs). Maybe I might keep a few bucks in the market for the entertainment value.

  10. Chris Selland says:

    “Missing is part of the long process of winning” definitely gets my vote for QOTD – we’ve all been there – tks for the inspiration.

  11. Chris Selland says:

    “Missing is part of the long process of winning” definitely gets my vote for QOTD – we've all been there – tks for the inspiration.

  12. Dave Pinsen says:

    You're modest, but you've crushed it as an angel investor, and you're a successful serial entrepreneur to boot. If I were you, I'd be tempted to take my money out of the stock market and just invest it in more start-ups (your own and those of other entrepreneurs). Maybe I might keep a few bucks in the market for the entertainment value.

  13. John Kai says:

    I like this post, it helps to know that those I look to emulate have the same self doubt that I have. You may have missed on some of these novel ideas, but you still picked up the bat and are at the plate taking your cuts. StockTwits is the best thing that I’ve ever come across and it’s allowed me to learn from so many other generous people who give of their time, ideas, insight, advice and encouragement. You are the leader of this tribe and I believe in you.

  14. John Kai says:

    I like this post, it helps to know that those I look to emulate have the same self doubt that I have. You may have missed on some of these novel ideas, but you still picked up the bat and are at the plate taking your cuts. StockTwits is the best thing that I've ever come across and it's allowed me to learn from so many other generous people who give of their time, ideas, insight, advice and encouragement. You are the leader of this tribe and I believe in you.

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