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  • Jack Fleming

Choose Your Boss, Not Your Job

“The leader you work under is the future you." - David Salyers, Marketing Executive Chick-Fil-A

Mike Budenholzer worked for the San Antonio Spurs under Gregg Popovich from 1996-2013, now Head Coach of the Milwaukee Bucks. In Budenholzer's moving 2015 coach of the year speech he said this:

"I can't even begin to articulate how thankful I am and all the things I've learned. The thing that Pop did for me, and did for a lot of coaches, is that he let me coach. And it seems really simple, and that's part of the beauty about being with Pop, sometimes the things that are most successful.. are very very simple." - Mike Budenholzer

Pop is mentioned from 9:30 onwards.

He doesn't talk about how great it was to work for the Spurs, he talks about Pop. The person he spent the day to day with, learned from and was guided by.

Social status is what drives most people. The trap of the short term title, to put up on your Linkedin.

What do most people complain about? Their boss.

Peter Thiel said this about his first corporate career - "From the outside, everybody wanted to get in.. but on the inside, everybody wanted to get out."

This can often be seen in high status jobs, the big name or brand in the industry. You get that job, but sometimes your boss is a pain in in the ass and every day becomes miserable.

Conversely, you have a job with a wonderful manager who cares deeply about your progress your experience is wonderful even though others might not understand why you work there.


Jim Collins calls that 'who luck' - there's there's significant compounding interest when working with great people.

Working under Kevin Goorjian for me, was one of the best decisions I've ever made for the reasons written in the article linked. When you work for somebody who you admire, wants the best for you and your own growth there's a non-observable compound interest involved.

How to Find Who Luck

I say these things as somebody who has made all of these mistakes and hope that they can be valuable. I have sent way too long e-mails to people, stayed with the people I know at conferences, asked for advice without giving first and sounded egotistical on social media.

Who luck is based on generosity and loyalty.

  1. Be Proactive - share with others, call people up and ask questions, DM them on Twitter, go and watch practice, introduce yourself. Don't sit in the corner with the people you know all day at the coaches conference.

  2. Get outside your circle - the fortunate part of 2020 is people all over the world willing to talk, there are coaches Zooms going on everywhere who can you get to know?

  3. Help first - before you go asking a million questions about your industry. Ask how can I help that person I want to know? Send them notes, video, a resource you have created, information on players they might want.

  4. Don't be annoying - If you have a question via DM, don't make it super super long. Don't pepper these people consistently to where you become a pest. Be direct, be grateful, then get out.

  5. Don't be a self promoting ass - if you ask for advice, listen more than you talk. If your social media looks or sounds like it's all about you, or if you have already figured it out people won't want to help you.

“Most fundamental work principle: Make your passion and your work one and the same and do it with people you want to be with.” - Ray Dalio

Who do you want to work for?

Other Resources

If you have any thoughts or enjoyed this article, please share on Twitter or shoot me an e-mail at

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