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 allowed myself to include all of my “ridiculous” wants and aspirations on my list of 2023 goals, one of which was “finding a coach and co-collaborator who would agree to hold meetings from the chairlift.” Believe it or not, I was actually able to manifest that.
Read more ➞It is amazing what you can achieve if you get out of your own way.
Read more ➞I have learned the important lesson that being mediocre at anything is not a “safe” path to success. I now realize that the “safe” path for others may not be the best route for me.
Read more ➞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 seemingly impossible feats.
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