I think Jerry Colonna is awesome and of course I don’t have to say anything about Fred Wilson. I see both of them as my mentors and coach. I have had the pleasure of being in one of Jerry’s CEO Bootcamps. I wrote about it.  I highly encourage you to subscribe to Jerry’s Podcasts through Reboot.io. I am trying to get Jerry to come to Iceland, maybe we will get that done this fall, if everything goes according to plan. This blog post is trying to get gist of wisdom from the postcast with the same title where Jerry was talking to Fred. Both of them have been friends for over 19 years, they have enough scars and wins under their belt to talk about what really matters being an investor. I find the podcast was authentic and had pearls of wisdom in it. As an investor there are so many subtle things that you need to do, in addition, as an investor there is a moral obligation to do right by the company. Trust is the key thing, you must as an investor establish trust with the entrepreneur, you can only do that by action. You need to demonstrate to the Founder that you are somebody they can trust and you are somebody who is on their side. I think Fred goes into this a lot in the call. We are so fortunate to have people like Fred Wilson, Brad Feld and Jerry Colonna who share openly and be vulnerable in their stories. Here are some excerpts:

Jerry: No one really knows the secret beginning of Flatiron Partners was all about our mutual anxieties.

Fred: I have always been ambitious and really wanted to start my own venture capital firm, but I was scared out of my mind.

I have always wanted to make something happen in the world.

Fred: I went down with the sinking ship

Here is the actual article it has a number of reference links, so I highly encourage you to go to the link and read the links. I am embedding the SoundCloud here to make it easy to listen to it here.


I have learnt so much listening to this podcast and I hope you do as well. Being a good investor makes you a good businessman and founder.