Lee Geiger

Wish I didn’t know now what I didn’t know then

Bob Seger, “Against the Wind” (1980)

August 4, 1986 – The sweat comes first. After a thirty-minute hike to midtown Manhattan, my monogrammed Brooks Brothers shirt is already surrendering to a sweltering sunrise worthy of a Cambodian jungle. Then comes the swagger. I march into the headquarters of The First Boston Corporation, arguably the hottest investment bank on the planet, with the cockiness of a first-round draft pick. I’m a 26-year-old Ivy League MBA, armed with more confidence than common sense and convinced I’m destined to conquer the world. It’s my first day on Wall Street. What could possibly go wrong?

August 4, 2026 – I’m winding my way through the quiet streets of Orinda toward Penserra’s corporate headquarters, a boutique financial services firm that’s been my professional home for the last 17 years. Thank goodness the commute is just 12 minutes, because I’m half-awake and desperately in need of caffeine. My daily uniform consists of rumpled jeans, wrinkled polo shirt, and slip-on sneakers. Such is the life of a 66-year-old compliance officer with a sore back and small bladder, and the unsettling realization that today is my 40^th anniversary on Wall Street.

For the love of Mike, how did I get here?

I promise not to drag you through a four-decade highlight reel of my career, especially those tiresome myths about “when I used to be somebody.” Those stories are shaggier than my dog Brody. Nor am I about to serve up another dubious helping of career advice from Mount Geiger. If I had all the answers, I’d be writing this from my villa in Tuscany.

This missive was inspired by a group of college interns who spent six weeks at Penserra soaking up everything they could about the investment business. Somewhere between the financial markets, career conversations, and free lunches from Gordo’s, they convinced me my questionable career choices might be worth learning from. Given that I have underwear older than every one of them, it’s easy to see why they treated me like Wall Street’s version of Yoda.

Humor me for a minute. Imagine the greybeard version of Lee hijacks an elevator ride with his 26-year-old presumptuous self on his first day at First Boston. It’s August 1986. Traders still smoke big cigars on the trading floor, and suspenders and gold collar bars pass for high fashion. Here’s what the Wheezer of Wall Street might have whispered to the smug kid who thought he was God’s gift to finance before the elevator doors opened.

• “The S&P 500 is at 235. Forty years from today it will be around 7,500. That’s roughly a 9% annual return, just like it’s averaged for the last hundred years. Don’t overthink this.”
• “Dial down the arrogance. You’re not that smart. Or that good. This business will humble you faster than the Millennium Falcon jumping to lightspeed.”
• “Don’t be afraid to make mistakes. Nobody learns anything by being right all the time.”
• “At least once, you’re going to get knocked on your financial ass. You’ll probably deserve it, too. You’ll be okay so long as you have the guts to stay in the game.”
• “Learn to spot BS. Age and experience don’t automatically make people smarter than you. In fact, it’s often just the opposite. The world is full of pompous ‘experts’ who are truly certifiable idiots.”
• “Be patient. Careers are marathons, not sprints. Some days you’ll swear you’re running in quicksand.”
• “Rare is the career chart that only goes north by northeast. Yours will wander south, west, and everywhere in between. Don’t panic. Just keep learning.”
• “Find a mentor. Careers accelerate when a cheerleader has your back.”
• “You’re going to make a lot of money. You’re also going to lose a lot of money. Live by the mantra that money is a lousy way of keeping score.”
• “Nothing drains financial capital faster than lending money to family. When they ask, tell them you’re saving for their inheritance.”
• “Remember who you are. More importantly, remember who you aren’t. You’re a sales guy, not a CEO.”
• “Buy and hold is a much better investment strategy than trading every market trend like your hair is on fire. You already know you’re not that smart—no need to prove it twice.”
• “There are only two ways to get rich in this business: make a lot of money, or don’t spend a lot of money. Do both and you can retire before Medicare.”
• “Get a dog. They’ll love you no matter which way the market goes. Or what your boss has to say.”

Whether 26-year-old me would have listened is another matter. Probably not.

How did forty years disappear so quickly? Beats me. I’ve tried to retire three times, and every attempt has ended the same way—I get bored and wander back to work. I have no discernible hobbies, and I refuse to spend every day on a golf course. As for pickleball—there are some lines I just won’t cross.

Fortunately, I work with terrific people at a dynamic company, most of whom were born after the Reagan Administration. No kid grows up dreaming of a career in financial services compliance, yet I’ve found the work both moderately rewarding and endlessly challenging. Which is probably fitting for a guy who has spent forty years learning exactly which rules are worth following—and which ones are worth questioning.