I Would NEVER Do a Deal With YOU Again!

Posted by Howard
on December 20th, 2009

I have been investing in start-ups for 15 plus years and it’s hard.

It is not easy to lead a deal, it is not easy to be a small angel and it is not easy to syndicate a deal. There is not one way to skin the investing cat.

I believe I have gotten better at all of the above because I have been in every position. I have had big successes and big failures.. I am always amazed at how backwards the whole process can still be in 2010.

Yesterday, Bijan wrote a post entitled ‘We Gotta Do a Deal Together . Fred followed up with ‘Trading Deals…A lost Art? ‘. Brad Feld of Foundry whose firm just led Stocktwits B round also chimes in and he also mentions how they reached out to me during our process . All three are great posts.

I wanted to chime into the meme, as I have been an angel and first investor in many deals only to be completely disappointed by later investors and ‘teams’. The good ones are easy to talk about.

I have been written off Boards and even observer lists in 2010. Large VC’s have tried to stick me with their own due diligence legal bills. One of the largest VC’s stuck it to me good by doing due diligence on one of my companies, only to say not interested and announce an investment in a related business the following Monday (ouch, but I should have been more careful). Because I am entrepreneur friendly first, it always hurts, but I go along to get along because of the size of many of my investments. If you don’t want me on the team, I don’t want to be on the team. I also have a very long memory.

If not for all the work I put in to my angel investments, I would just hit the bid in some instances if allowed.

As The VC industry rapidly evolves, I don’t think the average VC’s will change, they will likely get left behind or stuck with the below average deals they deserve. Today, you need to roll up your sleeves when angel/VC investing. The rolodex helps, but you need to let the entrepreneurs know how to use you and EVERYBODY has to be on the same team.

Software investing legend Bill Burnham chimes in on how the VC industry is evolving in Web/Tech . It’s awesome. I agree with Bill and it feels good to be a part of this change wave.

For the other slights, winning is my motivator.

The information in this blog post represents my own opinions and does not contain a recommendation for any particular security or investment. I or my affiliates may hold positions or other interests in securities mentioned in the Blog, please see my Disclaimer page for my full disclaimer.