What If Everything Goes Right Rather Than Wrong?

In investing, and in life in general, an ability to foresee potential pitfalls has served me well.

However, being able to see what can go wrong can prevent me from seizing an opportunity. I sometimes forget that most of my successes have been the result of believing that I, or someone I have invested in, could achieve seemingly impossible things.

Case in point: We invested in idaciti when the founder had little more than a PowerPoint presentation and an idea. She had previously achieved a successful exit, so we had that to go on, but she was trying to compete in a challenging market, and there were a million reasons why her company should have failed.

But we could see her tenacity, and the outcome she could achieve if things went well. She sold her company to FactSet (NYSE: FDS | NASDAQ: FDS) this year and achieved a meaningful outcome for herself and her investors.  

Ben Capell is the managing director of one of our portfolio funds, Peterson Ventures. He once advised us to remember to ask: "What if this works?" A while back he wrote an excellent article on how to ask this question effectively.

I recently missed out on a personal investment opportunity because I failed to follow his advice. I’m hoping that writing this post will help me to remember to keep asking his question.