Thinking about deals

InvestingI have been spending a lot of time in my head these days thinking about the deals I am in, the deals in the pipeline and what kind of companies we will see in the next couple of years. 

No surprises that we spend a lot of time talking about the future in our house.  Fred gave a talk at Le Web last week which is worth watching.  He spoke about what the next ten years will bring in regards to the investments that his company, USV is talking about. 

When I think about the deals I am in and the decision I made to be in them I think about the past (when I made the investment) and the future in regards to jumping in at the right time and place to move forward.  I am far from a passive investor and so I do need to have a connection with the person I am investing in.  I sometimes think I am betting on an incredible jockey that happens to be riding a fantastic horse. 

There are more than a handful of companies that I am invested in where I gave them their first dollar.  It is bold to do that without any conversation with a group of partners but to be solo.  I have certainly figured out how to be solo while building a wonderful group of strategic investors that I work with in the angel arena including the VC's at all different levels who do early stage and later stage.  It has worked for me.  Yet there are definitely some times where I think I am out of my mind investing in all the companies so early.  Then there are the days when I have a bunch of amazing meetings with companies I am invested in and think wow I am so psyched that I jumped in on this deal.  I love this entrepreneur. 

It is all part of the investment roller coaster.  Exhilarating, intellectually challenging, crazy and exhausting.  I guess that is how I like it. 

This past year has been a turning point.  I lost a company and through that experience I learned a tremendous amount.  It is painful fo lose a company that you believed in but unfortunately it is a part of the risk one takes when investing early.  I also had a big exit which was exhilarating and wonderful for everyone involved.  I am kind of sad not to spend time with that company anymore but again that is part of the world I live in.

There will be lots of changes in the start-up world in the next year.  Money is changing hands as more angels come into the arena.  There are more companies being started in every single vertical and we are seeing investors put money into areas that they never thought they would before.  Technology companies that have a bend towards a medical platform.  They are companies that have a life science and medical component but they really have a technology foundation so investors who would not usually go into this space find themselves comfortable in it.  We will probably see more large companies buying smaller companies who are nimble and provide something that the large company needs but could never build themselves. 

This time of the year is a good time to reflect about the past and think about the future.  Investing in start-ups is all about the future and as I close up a the year )with a few in the pipeline) I am really looking forward to 2014.