I met Ryan Holmes, founder and CEO of Hootsuite at a Twitter Developer API promotion event (ha! in hindsight) probably in 2009.

So many apps like his had been funded, including Tweetdeck (which I was an investor).  Nobody cared for another one.  I am pretty sure Ryan was trying to raise some money on a $1 million valuation.  We hit it off. I wanted to invest, but definitely had conflicted feelings about being an investor in 2 similar apps.  I passed.

I had many other opportunities to invest along the way as we met and discussed the social space at events, but I passed.  I still had no good reason to pass other than some internal feelings of conflict (note to self…as Fred Wilson always reminds me…no conflict, no interest!).

Ryan in the meantime was building a killer enterprise business off the freemium software model and dancing the good dance with Twitter.  Probably better than anyone.

Today was Ryan’s big payoff.  A $165 million investment at lord knows what valuation ($1 billion plus I assume).

Could not happen to a nicer guy in our business.  It is amazing what the social web has sprung on the world since the market bottom in March 2009.

I will just add it to the millions I keep leaving on the table. It’s thrilling to see this stuff happen to contemporaries and not quite as thrilling to be so close but so far from that kind of payday (conservatively I would estimate that a $100,000 angel investment is today worth $4 million).

The markets are opportunity machines, you need to just stay in the game, hustle yourself into position and repeat for about 30 years.