When to Invest Vs. When to Help

A few weeks ago, I auditioned to be one of the new dragons on CBC’s Dragon’s Den. Now, before any of you purists judge me, let me just say: (a) they called and asked nicely; (b) lunch was provided; and (c) I got fake eyelashes in the bargain. Let him who is without skimpy lashes cast the first stone.

The audition was run like an actual episode, which is where things got interesting. There was one pitch in particular that even now, weeks later, stays with me. If you unpacked the pitch from its elevator formula, it became clear that what the person wanted wasn’t a cash investment but, simply, help in realizing a particular dream. Unfortunately, we as a panel were too busy trying to establish our investor chops; we dismissed the pitch for fairly cursory business reasons. Looking back, I think we missed the point entirely: as an investor, what do you do when someone asks for help, not money?

It’s a question that, as lawyers, my partners and I often ask. How much should we do for X business or Y entrepreneur, if we cannot monetize the effort? We don’t have a good answer; we just know that there are some ideas that are so compelling that they need to be served, even if they seem likely to fail. This is a sentiment we’ve heard time and again from our colleagues in California and Boston, too, and I’ve come to think of this as a fundamental part of the soul of any entrepreneurial community. Have you helped tilt at a windmill today?