Get your next mentor by being slightly annoying

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Brian Wiegand is a very low-profile guy who has sold three companies, most recently to Microsoft. He is big enough that TechCrunch writes about him as a good bet for anyone betting. But the bane of Brian's existence is that his exits have all been for under $50 million.

This is enough for him to have a private jet and be King of Madison (Wisconsin), but not enough for him to get a lot of respect in Silicon Valley. A quote from my advisory board member who lives in Silicon Valley: “For big VCs, $50 million is a rounding error.”

So Brian is not looking for people to mentor or boards to sit on because he is consumed with running his fourth company,, which will compete with Wal-Mart and Target.

I do not tell Brian that I will have a hard time ever missing a trip to Target to shop at Alice because Target has such great clothes that are so cheap they are almost free.

Well, actually I did tell him that. And I told him a bunch of other stuff, because I decided that I need him as a mentor. Eventually, I got him to agree to be on the board of my company. Here's the process I took to convince him to help me. And these are good steps for anytime you have someone you'd like to ask to be your mentor:

1. Don't be discouraged by lack of response.

The way Brian operates is that he doesn't talk to anyone in Madison and I had to send him fifteen emails before he'd have lunch with me.

Later her told me that he gets so many invitations for lunch that he doesn't even respond until someone sends him two emails. “They have to show a little tenacity,” he says.

2. Find the person's weakness, so you know where you can help him.

When we had lunch I opened by regaling him with stories of my dating life, to make him feel a little unstable and vulnerable. And then I launched into how he needs to help more entrepreneurs and he is helping no one in Madison and it's not enough to be great at building companies. “You need to be great at building communities of people building companies,” I told him.

He looked at me with an incredulous stare.

“It's more fun that way,” I said. “We're doing this for fun, right? I mean, you do not need more money. So there is no rational reason for you to be working insane hours for another company. And I do need a lot more money. And it would be much safer for me to go to a Fortune 500 company and draw a big salary than take a risk on a startup. So we're both doing this for fun, right? And it's more fun if you help more people.”

Brian pointed out to me his companies made several people in Madison millionaires.

Immediately I wish I had met him earlier. Like, when I was scooping ice cream at 31 Flavors and I could have been getting him coffee in exchange for stock options.

We come to an agreement that he will help me because he wants to be a good and giving person and I promise him that I will be fun.

3. Be real. No one wants to mentor someone who is perfect.

I then proceeded to be totally not fun by running out of money, being moody and difficult, and totally pissing off my lead investor who is also one of his investors. To the point where Brian told me that he couldn't be associated with my company. Because we were in too much trouble.

He would not agree that he said that. I am summarizing. But this is really the crux of the whole problem: He is the paragon of diplomacy and I am not. And I need to be. Because we live in a small town. And all angel funding is local.

But while I was melting down, he was paying attention. For the first time, I didn't have to chase him — he was genuinely interested in how I was getting out of my mess.

4. Remember that good advice is harder to find than money.

Speaking of melting down over money, you'd think it would be totally annoying to me that he's not putting money into my company. Because money is local. And he is local. And he is money.

We talk about this over lunch. And he is paying for lunch. That's a good start.

It's our third lunch. I pace myself for topics to cover. I try not to think about the fact that he gets a little antsy at the end. Like, he just sort of gets up when he's done. Other people kind of wind down the conversation. Or do something like fold their napkin. He just stands up. Sometimes I'm mid-thought.

I am one of the most socially awkward people I hang out with, so it takes a lot for me to be making remarks about someone else's social retardation. But the truth is, though, that entrepreneurs are often described as quirky, and Brian's weirdness makes me trust his advice more.

Brian gives great advice about the nuts and bolts of running a company. After all, once you've done three, you have to have sort of a system for going the distance, right? He is great for keeping me focused. I am always thinking about the future — where is human resources going? Where is generation Y going? Where is blogging going? I am asking the huge questions instead of “Did anyone call Deloitte to find out what they are posting on Brazen Careerist next month?”

Brian says something like, “What are you doing to make sure that everyone in the company is focused on the same vision?”

5. In the end, you want the mentor to care about you as a person.

I knew things were going well when we were talking about how to make payroll and Brian said, “Wait. One more thing. You have to get rid of that farmer.” (And I'm thinking, “Brian, when you are walking through the parking lot for your private jet, why don't you look around for someone better for me to date?”)

The great thing about Brian is that he's exited enough startups that he can afford to be light. For isolated moments. Most entrepreneurs are anxious during the early phase of a startup. Obsessively focused. Tweaking models often. Praying something sticks.

Brian is steady though — he knows he'll figure it out. When it comes to building a company, Brian has the perfect combination of calm and excitement. And in the end, I think he might be my mentor for being lighthearted and calm. Or faking it.

You should try to get a mentor like Brian. But since you probably won't get one right away — after all, you need at least fifteen emails — you should subscribe to his Twitter feed. Which I love. It's a peek into how a startup unfolds in an entrepreneur's brain.

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  1. Jonha
    Jonha says:

    Hi Penelope,

    Does it mean it’s okay for people to ask you “Hey Pen I want you to be my mentor” for the Nth time? You sure you won’t get annoyed by regular emails asking you to be someone’s mentor because I think I’d want you to be my mentor. I’m not sure where you could help me though (though I know I admire you and all but my life is too messed up I still couldn’t figure out where exactly your quirkiness and wit could help me the best). I know I gotta help myself because someone else or someone like you would. I’m still working on the first phase so you won’t be expecting dozens of emails from me anytime soon, lol. But I gotta commend at how fast you respond on anyone, just like how you DM me on Twitter. Too bad you walked out when I started talking about Tim Ferris, lol. Don’t worry, I am not one of his angels, lol.


  2. david d
    david d says:

    Although this article was posted a couple of years ago, the timing for me to find this couldn’t be better. It actually has guided me in another direction to find a mentor and it’s someone I wouldn’t have thought about unless I read this. He cares, has influence and will be perfect for my venture.

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