David B. Lerner

Dave Lerner, 3x Entrepreneur, Angel Investor, Host of Venture Studio
Entrepreneur, Angel Investor, Director of Columbia University Venture Lab, Blogger, Community Organizer, Golfer-in-Exile.

Mentorship Gone Wrong: Three Things to Watch Out For

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This is part of my Mini-Series on Mentorship

It occured to me that no series on mentorship would be worth much if I didn't make mention of the various forms of bad or faux mentorship I've seen out there. In fact, from what I've observed over the years, the worst advice is actually well-intentioned. 

In a startup context, bad advice is particularly devastating and can actually kill you before you even get started.

So here's a list of some stuff that amounts to "mentorship-gone-wrong":

The "Mentor" Has No Concept of what Mentorship Actually Means:

 An entrepreneur I know once told me he was having some "issues" with a team member. He told me he'd tried to "mentor" him and it "wasn't working". I checked into the situation- basically he'd had a few phone conversatons with the other guy amounting to a cross between a beration and a pep-talk. This is so far from mentorship it's almost comical. Nevertheless, the profundity of his lack of understanding of what basic mentorship involves was stunning. 

The "Mentor" Has Zero Experience or Understanding of the Startup World:

 Often I see fledgling entrepreneurs seek out advice from well-intentioned people who are not in the startup world but have been successful (or perhaps not) elsewhere, (ie. lawyers, bankers, executives, accountants, etc.) Inevitably these folks always feel as though they have a lot to share. Rarely do such folks say: "you really ought to talk to someone in the startup world who knows what they're talking about". These interactions often lead to the worst and most damaging advice I see. They often, for example, make introductions to people they think are "venture capitalists" who are usually unscrupulous broker-dealers. With one single careless introduction they can ruin an unsuspecting person's entrepreneurial life.

The Delicate Category of Certain Lawyers who Fancy Themselves to be Mentors                               

This one's a delicate issue because there are definitely a couple of individuals out there in the startup world who make great mentors and also happen to be lawyers. But make no mistake, this is the overwhelming exception rather than the rule.

If you're an entrepreneur you really should be mentored by an entrepreneur, not by someone billing you by the hour.

In fact, I see loads of easily resolvable transactions destroyed by lawyers who try to insert themselves way too aggressively on the business-side of issues and get into their clients' heads in a big way, especially those clients are new to entrepreneurship.

Nature (and lawyers) abhor a vaccum.

Remember, you are the entrepreneur- you make the deals happen- the lawyer you pay alerts you to legitmate issues and papers the deal. That's how it should work.

That's it for now. If you think I've left anything out please by all means leave a comment!


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As a lawyer I can't say I entirely disagree with the comments re the damage that can be done by even a well-intentioned lawyer, but I think the underlying point isn't don't listen to a lawyer on anything other than how to "paper the deal;" rather seek out people who share your interest and passion, and if they have skills or experience that you don't and that are needed then so much the better. Those with previous entrepreneurial experience are at the top of the list, but if the person meets the first test then isn't legal (or financial, operations, marketing, sales, etc) training and/or experience a bonus - assuming they haven't been entirely corrupted by law school a/or private firm practice?

RC you make some strong points... thanks for weighing in. I bet you and I would agree on a lot of things- as we've both seen some damage done by bad advice. And yes, of course, with the right person and right motivations- all that interdisciplinary experience can be invaluable.

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