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. Mark W.
    Mark W. says:

    “… you should subscribe to his Twitter feed. Which I love. It's a peek into how a startup unfolds in an entrepreneur's brain.”
    This is funny since I spent a fair amount of time on last weekend looking over their community blog ( where Rebecca (modite) has written a few posts. Then I came across their founder’s blog ( which is documenting the startup process of .

  2. Matt Secor
    Matt Secor says:

    I've been reading your site for a few months and noticed advice in this article that I’d never really thought of before: getting a mentor for a specific purpose (i.e. "mentor for being lighthearted and calm. Or faking it."). If only being calm were as easy as faking it. I suppose I could use a mentor like that as well.

    I understand that it's important to have a few mentors, but is it really a good idea to pigeonhole what type of advice you get from a person? In my opinion you should learn from everyone around you, even if you'd never consider them as a mentor.

    Since you commonly mention finding ways to help a mentor, and a mentor is by definition helping you, do you see a difference between networking and finding a mentor? I'd be interested to hear your thoughts on this, and, like usual, loved this post.

  3. Ian Selvarajah
    Ian Selvarajah says:

    “Did anyone call Deloitte to find out what they are posting on Brazen Careerist next month?”

    Totally off topic, but who is writing the Deloitte stuff for BC? I’ve asked around here and it’s still a mystery to me…

  4. Debby :)
    Debby :) says:

    You’re so funny! I would love for you to share what you would write in 15 e-mails you sent someone. Lately, I have tried some e-mail marketing tactics… sending personal e-mails to people I can’t get on the phone… and it is working! 1/2 the people respond, and 1 out of 20 give me appointments. But I only send 2 e-mails. I am curious about what you would say in 15… That would be a great blog post for you to do!!!

  5. lizriz
    lizriz says:

    For what it’s worth, I haven’t shopped at Target in over a year. It was two things: 1. That bullseye ad and the fact that they blow off bloggers and new media, and 2. it turns out I like shopping at CVS a lot better. It’s easier to park, it’s easier to find exactly what I need, it’s easier to check out, and I don’t buy a ton of things that I don’t need.

    And yet, this month, I’ve been meaning to go to CVS for about three weeks now, and I simply haven’t had the time. So I signed up for notifications on, ’cause it looks interesting. (And I read the words “free shipping,” which is key.)

  6. Jamie Varon
    Jamie Varon says:

    Good to know. I’m quite good at being persistent, but bad in the whole “OH MY GOD, I AM SO ANNOYING, THEY WILL NEVER WANT TO TALK TO ME” area.

    Plus, email is great because you don’t have to see the person roll their eyes. I don’t think there is an emoticon yet for annoyance.

  7. Carrie
    Carrie says:

    Wow Alice looks great! Tell Brian that if he can get some Charmin delivered to my house once a month I am so on board.

    And along the lines of being annoying, Why don’t you blog about my iPhone game, Colorific? Thanks!

    I figure you owe me one, since I checked this blog at work once and the header said in giant letters “Successful women get more Oral Sex” or something along those lines… Now I could write an article about how to blame a stray google result for ending up on a website that says “Oral Sex”.

  8. Karl Staib - Work Happy Now
    Karl Staib - Work Happy Now says:

    I’ve been looking for a mentor and I’ve found some pretty good people. I’ve avoided being annoying as not to chase them off. The things is I haven’t gotten that close to any of them.

    I really need to let the annoying (real me) come out. If I keep giving them the toned down version of who I am they won’t ever really enjoy me.

    My challenge to myself is to start turning up the annoying. Not full blast at first. Just a little then seeing the results. If they like it then I’ll turn it up a little more. When they’ve had enough that’s when it’s too late. I’m completely myself and now they love me.

  9. Ryan
    Ryan says:

    Great post. Finding a mentor is a search. It has to be. Great mentors don’t come to you because the people who go around volunteering their time to help others have very little free time left. I found that the best mentors are at least a few steps away from the lime light. These seem to be the people with lots of energy. As someone who newly entered the workforce I’ve found it’s better to find someone with relatively more time and energy and relatively less special expertise and prestige. Almost anyone has something great to teach you.

    By the way, I work for Deloitte, but this is not how I came across your blog. You better make that phone call.

    I just found your blog tonight through T.Cowen over at Marginal Revolution. I think career and life is a great blog topic and I loved all dozen or so entries I’ve read tonight. Do you have any posts you could point me toward for someone just starting a career?

    Also, you mentioned careers are not for life fulfillment. I agree completely and working has become much more fun since realizing that. But what would you say are the most important things to gain from a career then?

  10. phillygrrl
    phillygrrl says:

    “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.”

    I say Facebook the hell out of ’em. That’s how I find mine :)

  11. Rhona Gilmour
    Rhona Gilmour says:

    Just remember that all those cheap clothes need to be made by cheap labour somewhere.

    They don’t look so good when you see a sweat shop staffed by children.

  12. Brian
    Brian says:

    Most candidates for being mentors in my area have questionable business conduct and this has been very frustrating because I ready to build my cadre. Also, rejection is most times deflating but it's encouraging to see that being – €˜annoyingly' persistent really pays off. I am now redoubling my efforts to build bridges online.

  13. Lisa
    Lisa says:

    My brazen new friend, I discovered you on the happiness project blog and look forward to continuing the journey with you. It feels like having an extra fifty bucks in my back pocket. Relationships? I’ll face the conflict; Money woes? I’ll get a mentor and improve the quality of the bullets on my resume; Parenting? I’ll be in the moment–it’s going so fast. Health? Must be first…yeh I’m stuck with a little pink ribbon. Joy? Ice skating, crocheting, reading, and donating my time to promote world peace. I better get on with it. Consider yourself showered with glittering confetti…THANKS!

  14. Barbara
    Barbara says:


    I wish you would post more on how to find local angel investors.

    I feel clueless about this sometimes.

    Maybe it’s a generational thing…even though I took your quiz and came up a Gen Y because I love and use technology, I am a product of the 1960s when people who actually had their own businesses were like remote gods, and middle class people like me were encouraged to work for the government because it was safe. (I actually followed mom and dad’s advice and tried it for a year. Got tired of the brain-dead co-workers who packed up their things at 4 and twiddled their thumbs until quittin’ time at 4:30, so I went back to school).

    Well, I am in Nashville so maybe I should try Trace Adkins…after all, he did come in second on Celebrity Apprentice…

  15. jrandom42
    jrandom42 says:

    Make sure you emphasize the SLIGHTLY part about being annoying. Overzealous persistance in pestering someone often backfires and you’ll get nowhere in finding a mentor.

  16. JT
    JT says:

    I have been a faithful reader of your blog for awhile now and was startng to give up as your posts were getting very stale (sorry for honesty, but I couldn’t read any more about whinning, it seemed as you lost the edge – the main reson why I signed up for your blog) until very recently – your posts have been AMAZING. I have to say, it wasn’t that things suddenly gotten positive, not at all, I am not looking for butterflies and candy, but they suddenly started to make sense and they were THE real advice…almost to the point that you have been giving so many great adivces that I can’t even implement them all. So kudos to you and finding the freshness and bringing back the “EDGE” to your posts – Keep up the great work…

  17. Dannie
    Dannie says:

    Oh Brazen One, you were having a good day. No attitudes, no breakdowns, I proud of you! You seem to have handeled yourself well during the interview and picked up some good insight for yourself and your fellow readers too. Keep up the good work!

  18. Blogs that Make Money
    Blogs that Make Money says:

    Thank you for that.

    It is hard enough that people think they can do everything on their own. You kick ass to by convincing someone they needed to be a mentor. Not just a mentor, but your mentor.

    I’ve learned that mentoring is like giving back, taking care of a debt or similar to karma. Also if you want to shape your market or industry pick up a couple of proteges otherwise some sectors go haywire from lack of direction.

    Great subject for people to really think about.

  19. Minx
    Minx says:

    I know this was probably written to show how much traffic you can defer to Brian’s email, so i signed up. because I support you, and I think you are awesome! Keep up the great work!

  20. Holly Collins
    Holly Collins says:

    Thanks for the information. Very interesting especially for someone who completely understood the statement about social awkwardness and quirky people make you trust them more.. Very insightful and correct…(coming from someone who was thrown into the world of social issues.) It’s interesting because after being in the corporate world for so long, I used to believe that to be truly successful one must be socially capable–never awkward. But the most brilliant people have social issues or Asperger's syndrome.

  21. Bleakspot
    Bleakspot says:

    Aren’t you a little old to be looking for a mentor?

    And seeming to be awkward or a little gauche as a strategy to put people at ease is okay, but then think of the really graceful people in the world, and how they make others feel at ease as well. It’s a total myth that all brilliant people have social issues–perpetuated by the internet.

    I’d be much more interested to read that Penelope is mentoring someone else or volunteering for a high school Jr. Achievement program or coaching some kid for a scholarship. That whole giving back thing–why not try it?

    • Don
      Don says:

      Apparently Brian became a mentor only after ceasing to be a potential investor. But anyway, Brian is Penelope’s ultimate mentor. He is literally who she wishes to be. Can’t blame her for sucking up to the guy. I’m more interested in why he would take the lunch (let alone pay for it.) What’s in it for him?

      Ardent pursuit using an email barrage only works for attractive women. For anyone else, it’s harassment.

    • Penelope Trunk
      Penelope Trunk says:

      Oh. Such a great opening here for me. First, my company, Brazen Careerist, is all about mentoring. And I started it because I want to give back. I learn as much from mentoring other people as I do from being mentored myself.

      Second, no one is ever too old to have a mentor. The minute you think you’re too old to have a mentor, then you think you’re too old to learn, and if you’re too old to learn, then you’re dead.


  22. Dan Ray
    Dan Ray says:

    Hi, Penelope. I agree with you on the value of being slightly annoying to your boss, as long as the emphasis is on the word “slightly.”
    As a boss, when someone I’ve hired turns out to be slightly annoying, I’ll work extra hard with that person to teach/mentor/indoctrinate/smooth out the rough edges. When someone I’ve hired turns out to be completely annoying, I’ll work extra hard with that person to make sure he leaves/is uncomfortable/gets fired.

    • Dannie
      Dannie says:

      Dan Ray you are a true Choleric personalitly. I can’t imagine that you would nuture anyone that “slightly” annoyed you. You apparently do not take the time to get to know candidates when you hire for a job. Remember , how you handle yourself is a reflection of you and the company you work for!

    • Penelope Trunk
      Penelope Trunk says:

      Wait. Hold it. This is a great comment, because Dan used to be my boss. And he fired me because I really crossed the line in the annoying category. To the point of disrespect. Dan, in fact, probably taught me the most about being a good employee.

      Dan, I love that you left this comment. And, also, you made me smile.


  23. Daniel
    Daniel says:

    "What are you doing to make sure that everyone in the company is focused on the same vision?"
    I agree with this totally. Great article!


  24. F
    F says:

    Fantastic post, but… you let him pay for lunch?! Why not paying for lunch yourself (even if he insists), that should be a no-brainer!

  25. Rajib Singh(Aldon)
    Rajib Singh(Aldon) says:

    M very very much disappointed with my manager, me n some of my friends are hired in a contract, however he and one of my team leader told us that
    “we will be made permanent”, at last we were told to leave the company. He hired 5 person out of 20, and i’m very much sure that i was doing much better then them, i was following the B.R.A.N.D, yes i agree sometimes the quality goes down, it doesn’t meant that it will happen all the time, I hope this message will go to Holly, target quality mentor, minneapolis. I request Holly to barge the call of representative who were made permanent recently as well as our calls, my id was ZG5105, location:-New delhi(india) Vcustomer.

  26. Elder Abuse
    Elder Abuse says:

    #2 is perhaps the best advice in my opinion. There will always be this “What’s in it for me” when it comes to just about anything people do, including mentoring. If you’re able to identify what exactly that person needs help with, then provide it to him/her unconditionally. More importantly, don’t be discouraged after the first “no”. Inevitably, it will happen. Just need to overcome it and target the person’s weakness, as Penelope mentioned above.

  27. chemotherapy
    chemotherapy says:

    I have had a few mentors in my career up to now… and i can say that article is perfectly right to say that mentors are there to guide us and care about our progress.

  28. chemotherapy
    chemotherapy says:

    forgot to add that for those wondering who my mentors were… my mentors were my own managers… i was very lucky to have the sort of managers that would protect their subordinates… but my current one really sucks… sometimes i’d get “slaughtered” in public by him… but then i’ve developed my skills at defending myself… :)

  29. Luton
    Luton says:

    Wow don’t know if I would have had the courage to approach such a big player initially. I watch dragons den and see so many people crumble when they have to go in front of someone who has already made their name.

  30. Jim
    Jim says:

    First, putting some boundaries around your work time seriously increases your productivity. If you have a sense that you can do it any time, or do it when you get home, you typically aren’t as focused and organized about your work. I particularly noticed this when I started an evening MBA program while working full time. On the days when I knew I had to leave for class by 5:30 and would be home late so wouldn’t have much time to do work after class, I got a lot more accomplished in a shorter period of time, simply because I knew it wasn’t an option to do work at home that night.

  31. diabetic
    diabetic says:

    You know we humans need mentors all our lifetime… it was like that and will be like that for as long as we’re humans(imperfect)… think about your parents as your first mentors, then teachers at school and etc…
    i realized that to be successful i had to have a mentor or at least follow one’s teachings, methods or his way of thinking… and then i met one when i was in my 20s.. it changed my life drastically… the confidence i got, the way things looked differently to me… success has become something achievable… so mentors are always needed..

  32. telepresence
    telepresence says:

    Hey Jim, that’s exactly what i started practicing… creating boundaries.. and i’m so relieved now… i couldn’t imagine how much “other people’s work” i’ve been doing all this while… some of your colleagues can be pretty sneaky and pass on their work to you… so you gotta be careful… i’m a lot happier now and less stressed…


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