After exiting a company that you spent years building you have some time to reflect on what you’ve done well and what you could have done better. You can go back and second guess and place blame all you like but in the end that doesn’t change anything. In the end, the only thing you can do is try to evaluate as objectively as possible the decisions that were made and the outcomes that resulted because of them. This is how we learn.
I’ve known many founders over the course of my twenty+ year career in tech. I know founders that I feel should have been much more successful based on what I know about their personality and drive and I know other founders that are wildly successful despite their seeming lack of qualifications. For somebody as data driven as me this really does pose quite a few questions. Even in my own career I look back on things that “should have worked” and other things that never should have but did anyway. I continue to come back to the same answer.
Timing.
This is not something you hear a lot of successful founders discussing. It can be very repetitive to listen to successful founders discuss how it was endless drive, a well selected and curated team and an unwillingness to fail that lead to their success. You never hear them say that they were in the right place at the right time with the right idea. And you DEFINITELY don’t hear them say that the place/time was really the most important part. Somehow, in this founder hero age, there is a point where you’re being told how great you are so often that it appears to be the antidote for humility.
Less successful founders on the other hand are very well aware of the time/place conundrum. I remember the first project I worked on when I graduated college and joined a large multinational tech consulting firm. We were working on a website that allowed individuals the ability to find music they liked and buy it, a song at a time, for $1. On top of that the site was hoping to sell “virtual tickets” to concerts around the world so that fans could watch their favorite bands light up the stage around the globe. I know what you’re thinking...iTunes right? Wrong. This company tried (and very successfully executed) to do what Steve Jobs and iTunes got right just a few years later but the timing was wrong. Napster was still in its glory days and nobody couldn't fathom having to pay for music that they could download for free. Internet speeds were just not where they needed to be in order to provide an online streaming platform. The idea, the team, the drive and the capital were all there and they were all right but yet the endeavor failed. I think back to the person who initiated that project. How they must feel about the eventual success of Apple doing the same thing they had done only a few years earlier.
My point in all of this is that you can’t let whether or not you were “successful” impact how you feel about any endeavor. I think that if you strive to remain humble and learn from all of your experiences, both good and bad, you are bound to have some wins. The wins are never as good as they seem and the losses never as bad but they are all valuable in helping you move forward in a better way.
Stay humble and stay hungry.