The Legion of Doom

Growth Through Adversarial Relationships… Part 4

Decision-First AI
5 min readJan 6, 2016

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I began this series of articles with the title Forget A Mentor, Get Yourself An Arch-Enemy. This final installment will start with a pair of relationships where I achieved both. Well, more accurately, where my mentors were often adversarial. I have little tolerance for bosses as arch-enemies since The Madman.

In 2005, I joined a new startup in the financial services industry. Unlike the startups of silicon valley and the bygone days of the DotBomb, this one was a literal who’s who of the late 90’s banking boom. To carry on the theme, I will refer to it as The Legion of Doom. Note-The Legion, unlike the banks of the 90s or pre-2008, had no love for predatory lending, reprice, or other unsavory practices…

The Professor

The first member of The Legion that I would encounter was the Professor. He was the hiring manager and THE most cerebral boss I could ever have. I am an analyst by trade-so this is quite a statement.

The professor drew on decades of experience, prolific reading, a diverse education, and a keen analytic view on everything! He knew the techniques, the shortcuts, the liabilities, the uncertainties, and the likely politics of every other player in The Legion-including the VC group which likely had a better claim to the name.

To walk into the professors office was always a trial, though I don’t think he always intended it to be. If you came with anything less than a B+ game, you were going to leave feeling exposed. To this day, the Professor remains the best boss I ever had. I don’t miss the trials, but I have the utmost respect for what that level of experience and scrutiny did for my career.

Al

The Saturday Morning Cartoon version of the Legion of Doom was led by Lex Luthor. The one I joined was led by a man with a lot more hair and a much more Italian complexion — lets call him Al.

Having just come from my time with The Don, Al’s sense of family was easy to adapt to. His passion and bravado — a little less so… Al was one of those people who had succeeded in numerous roles and numerous environments through a strong set of principles. Go hard, hire good people, and then push even harder!

The Legion was founded by those who had followed Al into battle many times before. His family was known for the same hard driving focus and many owned large portions of their success to his phenomenal drive. Which for me should have begged the question-”What happened to the last analyst in this family?”

Al was and remains a great mentor. To a person, anyone who ever worked for him would agree that his driven style is a challenge that creates some adversity. Few can appreciate the excruciating pain of trying to perform accurate and often complex data analysis and insight development to support him. If Al had asked me to be his pit crew at Indy, he would have demanded I sit on the rear stabilizer and replace the tires as he drove…

The Joker

My final example in this series, I leave for the gentleman who most truly met the definition of Arch-Enemy. He also is responsible for as much of my professional growth as any other nemesis I’ve detailed.

The Joker’s role at the Legion was directly tied to mine. He was tasked with validating, leveraging, and often disputing all of my findings. This is a fairly common construct in banking and financial services. It typically goes one of two ways; a partnership develops or someone leaves after a year or so. The former is typically short-lived as well. Most management prefers checks and balances.

The Joker and I faced off for nearly seven years! And while every once in a while we found some common ground, the relationship defined adversarial. To make matters worse, the debate was more often than not held in public forums — a situation I fought hard to prevent but rarely won. It was too beneficial to the Joker.

Adversarial relationships force you to raise your game. Adversarial relationships in public forums and boardrooms, force you to master it.

Over seven long years, I cannot count the number of times I wanted to ring the Joker’s neck. Frustration was only magnified by the pace at which Al ran the company. The level of pressure and frustration was brutal. Many colleagues who got just a taste were quickly broken and dismissed. But the Joker and I soldiered on…

In the end, the Joker, like so many others, remains a respected former colleague who I would happily work with again. Honestly, I miss him. Together we built a billion dollar company or at least prevented it from pulling itself apart. We shared a very unique experience at The Legion of Doom, a crucible of sorts.

I hope you learned something from my experiences. Hopefully you were entertained as well. I have nothing but respect for the folks I mentioned in this series. Many remain strong friends and colleagues. Adversity and adversarial relationships can bring out the worst in us, temporarily. If we embrace the opportunity and strive to rise to the challenge, it can create personal growth that will last a lifetime.

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