The only thing I know for certain about early-stage companies is that there will be uncertainty. Even the best opportunities often twist, turn and pivot thousands of times before they produce a return for their investors.
As an angel and the Chief Investment Officer at MergeLane, I focus most of my angel investing diligence on the team. I look for founders that are tenacious enough to break through walls and clever enough to figure out how to go around them.
When I meet with entrepreneurs, I rarely ask conventional questions. Sure, I look at the pro forma, review their business model, check out the competitive landscape, etc., but I typically send those types of questions by email.
When I talk with them, I want to learn how they think and what makes them tick. These are my favorite questions to that end:
I’ve spent most of my life learning how to turn off my passion for just long enough to eat and sleep. I’ve never had to learn how to turn it on. After a recent long stretch without that passion, here's my hypothesis as to why I think it is coming back.Read more ➞
I tried for many years to maintain a jam-packed schedule with zero margin for error, but life never seems to fit into perfectly scheduled boxes. After a straw-that-broke-the-camel’s-back moment, I’m learning to live off of the brink of disaster.Read more ➞
I've spent more time than necessary on our fund administration and reporting, in part because of some of the easily avoidable administrative mistakes I’ve made over my 10-year journey as a startup investor.Read more ➞
Over these past two months and throughout all of 2020, I've learned something that I want to record to make sure that I remember: My anxiety about the potential outcomes is almost always worse than the actual outcome.Read more ➞