What Your Worst Bosses Can Teach You, About You


After 15 years of being a Monk, I found the light. And left the monastery. 

I went from an environment of simplicity, cooperation and humility, into a corporate world of complexity, duplicity and ego. I swam with sharks, got shredded by them and reached the beaches of success - in spite of each of them.

I broke local, regional, national and unimagined sales records. Over and over again. I did what no one thought could be done.

I outsold all who sold on the street. I came in to turn around companies in advanced stages of revenue to rigor mortis and revived them to prosperous health. I fast-turned a failing media company with gross revenues of under $300,000.00 to just shy of $10,000,000.00 in less than four years.

Everything I did was in spite of the bosses I had. Everything I achieved was in direct contrast to the support I was promised but - never, ever given.

.My bosses became my teachers. Each one taught me. They became my Gupa or little Gurus. They showed me my own darkness. They lead me to dispel them and my own inner darkness as well. They nearly killed me but in the end I won. I'm about to tell you why and how.


Each boss, I made insanely unexpected and unimagined amounts money for - were worse than bad, Far worse. Darker than dark. Far darker, They enjoyed, relished in, were invigorated by and took pride in their toxic being and acting. They were trolls.

My worst bosses brought out the best in me. And how to help people and companies do the same for themselves.

My worse bosses showed me the value in helping turn dysfunctional business cultures into health ones.

They showed me how to turn toxic waste into rich green company wealth.

They drove me to start and grow a successful consulting company (WinThinking). They showed me how to leverages behavioral science, emotional intelligence and organizational acumen and direct it into profitable individual, team and company growth.

I’m still working out the worst they brought out in me. I nearly lost my wife, family and sense of self. I never though, lost my reputation. I did though come scary close to abandoning my sense of sense and self-esteem.

Unlike others who unexpectedly fell prey to my bosses real nature lying below their charm, I knew exactly what I was getting into. The aura of their darkness was as evident to me as their reputation was to savvy others within and across our industries.


Here’s 26 things I learned from my worst bosses. I hope they can encourage you learn from your trolls as well, They're there and ain't going away. It's about our take-a-ways.

1.    Monsters can be teachers. Even if they don’t intend to be.

2.  I determine good and bad.

3.    Who others are has nothing to do with who I am - unless I let it.

4.    Everything is neutral. My thinking colors everything.

5.    The worst of human nature can show me what best looks likes like.

6.    Toxic cultures are. I allow them to affect me or not.

7.    Fear does not have a hold on me, unless I allow it to.

8.    Fear based cultures are for the weak and afraid. Not my self definition.

9.    Fear suppresses innovation. Over time.

10. Fear suppresses profit margins and gross revenue capture. Over time.

11. Fear suppresses market share. Over time.

12. Fear is for those who seek security over excellence.

13. Facing fear is facing our school yard bullies, real or imagined.

14. Succumb to fear and become it.

15. Original thinking thrives in fail forward cultures.

16. Creativity is more about possibility than judgement.

17. Freedom of expression is the richest transactional value.

18. Having a say about value doesn’t necessarily you create it.

19. I create value. No one can take away what I create, unless I create permission.

20. Focusing on anything other than creating value only creates selfish value.

21. Selfless value has greater bitcoin value that pumped up self-filled value.

22. When I know my role, and do my job - everything else is distraction.

23. Ugly troll bosses exist. They are not my problem.

24. I am finished attracting troll bosses just to justify my unexpressed anger.

25. The ugliness I see is a reflection of me.

26.  I create meaningful, purposeful and relevant value. That is in itself enough.


While I may want revenge, my worst bosses taught me I don't need it to define myself.

What are your worse bosses, colleagues and relationships teaching you about you and what's needed for your success and well being?