Let me introduce the first mentor archetype with a cautionary tale. Entrepreneurs, especially serial entrepreneurs, are the mentor rock stars and I know many that are awesome startup mentors. They’ve been there. They’ve done it. They’ve proved they know how to succeed. Sometimes they’re right for your company – and sometimes they’re not.
The good ones have startup experience relevant to your situation. They like giving back to the community. Lots of them are angel investors. They usually have great networks that they can share. Many are looking for their next project. If you find the right one, it could be a match made in heaven.
While good entrepreneur mentors are awesome, but I’ve seen bad ones be disastrous. Their badness comes in many varieties. There are know-it-alls, yesterday’s men, Shark Tank wannabes, limelight seekers, and many more.
Mentors do a lot of talking, but we do try to listen and we try stick to what we know. The entrepreneur mentor know-it-all is quick to cut you off. They say ‘me’, ‘my’, and ‘I’ more than most people. They want to talk about ‘my exit’, ‘my vision’, ‘my cool spouse, kids, car, gadgets’, ‘my amazing offer’, and they know exactly what you should do.
Yesterday’s Man has credibility, because he’s ‘been there’, even if ‘there’ was ten, fifteen, or twenty years ago under completely different market conditions with completely different business models.
Getting lucky once doesn’t make you Steve Jobs. A lot of things have to go right for a startup to be a big success. Jobs was smart, but he worked with smart people in an industry that perfectly matched his talents at a time when explosive growth was possible.
Yesterday’s Man often wants you build your startup the way he built his, but business models have changed since a lot of these people hit it big. Ask yourself whether it makes sense. What did your phone look like ten years ago? You may be able to go further on a six-figure seed round, than Yesterday’s Man did with millions.
‘Shark Tank Wannabes’
I love Shark Tank, but I recognize that it is entertainment. Some mentors think their prior success marks them out as master negotiators. The art of the deal can be complex. If it was simple, there would not be so many books on the subject.
Many Shark Tank wannabes give bad advice on the ‘be a tough negotiator’ theme. They encourage you to make absurd demands and take the hard line. Sometimes standing your ground is the right thing to do, but it’s an easy course to advocate when you don’t have any skin in the game.
Success is intoxicating and a lot of successful entrepreneurs want back in the game once they leave the successful company they started. Some of them are doing it because they like being respected. They like being called rock stars. They like being adored. You don’t want to be their soapbox. Find someone that really wants to help you.
All good mentors are alike; each bad mentor is bad in his own way. There are lots of ways to be led astray that I’ll leave for later. ‘Amazing’ offers, exploding offers, empty promises, long sidetracks, and their many cousins are all time wasters. If you’re unlucky, they are worse.
Look both ways before you cross the road
Rock star serial entrepreneurs can be perfect for your startup. They are great for introductions to mentors, business developers, software developers, corporates, investors, advisors, advisory boards, and more. Sometimes they really do have the answers to your problems. And sometimes they don’t.