I've spent 30 years as an entrepreneur, and every time I've missed an opportunity to make tons of money, it's been due to a lack of curiosity.
1) I co-founded IGN in 1996 inside Imagine Media. Two years later, it was the 49th largest property on the web. Shortly after, I met with a consultant Imagine’s CEO hired to “ask questions and see if he could be helpful.” I took that at face value and unloaded all the problems I was struggling with. He got a truly unvarnished look at where I was weakest as a founder and leader.
If I had been curious, I might have asked about his background, how he knew our CEO and what *he* was focused on in his own career. With curiosity, I might have pieced together that he was actually being brought in as a CEO to spin IGN out into a separate company. In doing so, I might have given a better accounting of myself.
When IGN spun out a few months later, I wasn’t given an executive role (or even a management position) nor any meaningful equity. I soon quit in frustration. When IGN eventually sold for $650M, I made nothing.
2) In October of 2008, I met with Jack Dorsey and Ev Williams to discuss partnering with my company Gnip to syndicate their “firehose”. Though Jack was CEO, Ev ran the meeting and asked, “why should we continue to give this data away?” Man, did I have opinions, and, man, did I share them. I spoke at length about why Twitter should keep their data free.
If I had been curious, I would have asked Ev for his perspective. In doing so, I would have learned that Ev had some pretty strong (and ultimately correct) beliefs that Twitter’s value was a function of their unique data. A better response from me would have been, “Ev, at the end of the day, it’s Twitter’s data and whether you give it away or sell it, I don’t care – we just want to make that easier for you.”
Two days later, Ev fired Jack and took over as CEO and for the next 18 months, Twitter would have absolutely nothing to do with Gnip. I eventually left my startup and gave back 12% of the company that I had already vested. Shortly afterward, my co-founder went to Twitter, said what I should have said, got a partnership, and a few years later sold Gnip *to Twitter* for $154M. You can do the math.
3) I have so many of the stories. Officing next to Uber in 2010 and incuriously thinking it was the dumbest idea I’d heard (a $5k check in 2010 would have netted $25M at their IPO). Passing on an offer to become Zynga Chief Product Officer in 2007 because I didn’t like the way Mark Pincus critiqued Grand Theft Auto 4!
Belatedly, I have learned that when I feel the strongest about something, that’s the exact moment I’m probably silently punching myself in the face. In those moments, I try to take a deep breath and a step back and ask, “what does the other person know that I don’t?”
Have you ever made a costly mistake due to overconfidence? Consider the comments your safe space. I’d love to hear your own stories :)
#startup #strategy #curiosity