One of the many roles thrust upon us midlife males is learning how to say grateful goodbyes to those who’ve had a notable impact on our lives. Each time I say these goodbyes, I’m reminded of how fragile and inevitable my own future is.
This funeral was for one of my mentors of more than 40 years. He kept tabs on my career, advised me with wise counsel, keen wit, tireless optimism, and an endless supply of one-liners. He began as a retail stockbroker, went on to found his own advisory firm, and became one of the best money manager talent scouts in the business. His skills earned him seats on the boards of some of the most successful financial companies of the past 50 years, and his old-school Rolodex was a treasure chest of helpful friends.
He was a master at spotting opportunity and building relationships—two keys to creating wealth for himself and others. A voracious reader with strong opinions, he was both a fascinating person to visit and a sought-after guest. I always felt lifted when he shared his insights with that mischievous smile and laugh.
He taught me to look for the hidden story and humor behind financial headlines. With his sharp communication and interrogation skills, he reached second-level insights. His view was clear: think, don’t overthink. Do the homework. Place larger bets on fewer investments. Most investors, he argued, are over-diversified because they’re too lazy to dig deep enough to form a real opinion.
His mantra was simple: think for yourself. He read widely, interviewed constantly, listened carefully, but always made up his own mind. With just a few questions, he could test the depth of your knowledge and spot whether you were junior varsity or the real deal. I often felt less informed, which pushed me to work harder and surround myself with smarter people, hoping some of it would rub off.
He laughed at my early marketing efforts with wealthy clients. “Don’t you realize what rich people really want? It’s what they can’t have.” He criticized me for being too polite and available. And when I finally retired from professional money management, he asked if I was tired of giving “hand-jobs” to wealthy folks. That was his old-school, off-color humor.
He believed in the American dream, our financial markets, and the mix of creativity, greed, and excess that fuels them. He likened Wall Street to a giant frat party and simply wanted to outplay the bros. Politics, to him, was just comedic material—not part of the larger thesis. He stayed focused on what mattered.
His advice for us midlife males would be this: in your lifetime, only a handful of life-changing opportunities will cross your path. Most people miss them because they’re not paying attention, not willing to put in the work, or too distracted. But if you’re willing to do the research, make the calls, show up in person, and put skin in the game, exceptional outcomes await. He would push us to manage our mindset around risk and volatility, and avoid the common mistakes of human behavior.
While he loved seeing success and financial gains, he also carried the sharpest pin to puncture inflated egos. He reminded us often how lucky we are to live in America during such prosperous times, and how quickly a fool and his newfound wealth are separated.
When I once asked for fatherly advice about raising my boys, he paused and said, “Lower your expectations.”
Michael, you will be greatly missed.
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Ron Speaker
Financial Consigliere
Midlife Male Contributor
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