Making the Most of Mentorship (Or Help Me Help You)

Did the emperor in “The Emperor’s New Clothes” actually think he was decked out in the latest fashion? He had every reason to believe, since all who saw him complimented his new “outfit.” Or did he realize deep down that he was naked? This tale often comes to mind when I meet young founders who have been fed nothing but flattery by potential investors and seem to think that means something.

Carey Smith | Founding Contrarian

A wise man once said, “When you want to help people, you tell them the truth. When you want to help yourself, you tell them what they want to hear.” Obviously, a heck of a lot of investors are only interested in helping themselves. How else to account for the fact that they offer words of encouragement to so many founders with cockamamie ideas?

I think about this a lot, because in addition to talking to founders who contact Unorthodox Ventures hoping we’ll back them financially, I also have frequent mentorship calls with people seeking only advice. And in those calls I often get the feeling I’m the first person who’s ever cast a skeptical eye on their projects or told them anything remotely critical. But the way I see it, I wouldn’t be doing my job as a mentor if I didn’t point out flaws in their thinking or missteps in their execution.

Every founder who seeks mentoring should come prepared with questions, just as everyone who agrees to mentor a founder should not hesitate to speak their mind. The term “mentor,” after all, derives from the character Mentor in Homer’s Odyssey, a trusted advisor. It’s not from the French and Spanish word “mentir,” which means to lie.

So if, for example, someone comes in with a product that will never find a market because it doesn’t solve a problem, I tell them so. Or if their intention is to sell to government agencies, I say they’re in for a heap of bureaucratic heartache.

Or if they come to the office, prototype in hand, and it’s immediately broken by one of our not-so-gentle colleagues, I don’t gently say, “Come back when your product is further along,” like many VCs might. Instead, I point out the need to test their prototype on real users. And if a quick search turns up several strong competitors already selling a similar product online, I tell them they should have spent more time on market research before building a prototype in the first place.

These people are, for the most part, inexperienced; they need real help, not a pat on the back — that’s what friends and family are for. They need to hear honest, constructive feedback, from an objective outsider. Otherwise they can spend years pursuing a dream, only to wake up one day and realize they’ve gotten nowhere. I found myself in a similar situation with the first company I started, which is why I want to do whatever I can to help others avoid it.

I don’t know how many times I’ve heard, “You are the first person who has told me that.”

Well that’s just wonderful. But the reason VCs make it a habit to encourage founders and urge them to stay in touch is because from their perspective, there’s no financial upside to being honest. As they see it, even if a founder’s current idea sucks, their next one might be brilliant. And if that happens, VCs want to be first in line to get in on the action. So they don’t want to alienate founders or burn any bridges. But telling the truth should never set a bridge on fire. Under the right conditions, it can actually build it stronger.