Category: Business Strategy

The smartest person in the room?

Early in my career, I made a concerted effort to master work-related topics.

My goal was to ensure I was (or appeared) to be the most versed person on matters important to clients.

Nothing wrong with knowing your stuff, right?

The mistake I made was being the one doing the talking.

As I gained more experience working with clients, it became obvious that:

↳ The most stable client relationships were the ones in which we hardly spoke about work. It was always personal stories and friendly chats.

↳ The trust was strongest with clients I listened to more than I spoke to.

↳ I seldom had to impart my knowledge to clients as they trusted me and seldom asked hard or deep work-related questions.

Research shows that listening makes us seem more intelligent and trustworthy.

When we give others our attention, it signals respect, curiosity, and confidence.

There is a small twist, too. Studies reveal that sharing our point of view honestly without dominating a conversation boosts likability (even among strangers).

For me, I love getting to know people, and there is no better way to do that than to ask questions where I genuinely care to hear the answer.

In those answers are the gold nuggets upon which you can build both personal and business relationships.

The mark of a great leader (and friend) isn’t having the most to say but making others feel heard.

Sometimes the best mentors are the ones everyone tells you to avoid.

Fresh out of the Air Force, I stumbled into financial services by accident. MetLife office, updating my address, casual conversation with the receptionist – job offer.

The first few months were brutal. Cold calling from a phone book, struggling with everyone else in what was a “throw spaghetti at the wall” hiring strategy.

Then I noticed the other guy, the guy with the perfect suit, walking INTO the office at 8 PM when everyone else was leaving. Had the nicest office. Nobody would tell me much about him except “stay away.”

I did the opposite.

Bob was gruff at first. After a few weeks of casual hellos and quick conversations, we grabbed lunch. We shared many common interests and background stories. We became quick friends.

Turns out the office manager exiled him for refusing to follow his system. Called him “not a team player.”

Here’s the kicker, Bob’s sales dwarfed the entire office combined.

Bob had found something that worked. But instead of learning from him, management shunned him.

Not wanting to put our new friendship at risk, I never asked Bob for help. He knew I needed it, though. Out of nowhere, he offered to mentor me. “While this office ignores me, you had the guts to do what I did and go it alone, plus we’re friends.”

That mentorship changed everything. Without Bob, I would’ve left financial services.

He taught me three crucial and simple things that have shaped my career:
↳ Don’t sell – offer to help people who need it
↳ Be comfortable being the black sheep
↳ Make sure clients know you’re the expert (and BE the expert)

The person everyone tells you to avoid might just be the one who changes your life.

Growing up, I thought I was just “bad at school.”

During Pittsburgh winters of the 70s and 80s, the snow piled up on the road sides so high you couldn’t see the houses while walking to school.

❄️ Bundled in boots, scarf, jacket, and snow pants, I always had an end-of-day problem.

I worked more slowly than my classmates in math, and math was the final class of the day. So, when it came time to get ready to go home, I was still feverishly working while others were gearing up. I was often left behind.

I was also a slow reader who always got placed in slower reading groups in elementary school.

Soon, I started rushing through my math work just to avoid walking home alone.

The cost? I sacrificed my understanding of math just to keep up. Grades slipped.

After a while, the stigma of being a slow reader and my math struggles chipped away at my confidence.

The rest of my school career, I was locked in a cycle of Ds turning to Cs in math, and I avoided reading.

I approached my senior year of high school with little faith in my academic ability, which was a large contributor to my joining the military.

But two key things happened over the next four years:
↳I learned to love reading because I finally let myself go at my own pace
↳I built confidence and resilience that helped me overcome challenges

When I left the military, I had one goal: earn my bachelor’s degree.

Math fear still shadowed me. I barely survived college algebra. Then, one class, symbolic logic, finally opened my eyes. Suddenly, math wasn’t just problems on a page. It connected. It clicked.

That confidence carried me into a career in finance, entrepreneurship, and beyond.

Here’s what I learned:
We often label ourselves too early: “bad at math,” “ slow reader,” “not cut out for school.” Truth is, sometimes we just haven’t learned in a way that works for us.

So, if you’re behind or struggling, don’t let speed or comparison rob you of mastery. Go at your pace. Process deeply. That’s how growth sticks.

Let’s hear it in the chat about a label you threw off yourself.

Sometimes, reinvention isn’t a choice; it’s a lifeline.

I was about to turn 52 when my partners and I sold our wealth management practice. It wasn’t planned, but when PE-backed firms start buying up businesses like ours at valuations you can’t ignore, you take the deal.

👉 Financially, it was a win for us. Personally? It felt like everything I knew was floating away.

My role, the core of my career identity for 20 years, was being phased out. Leaving was an eventuality. The kicker? A strict non-compete meant I couldn’t just jump ship into another like role. At 52, with three sons and in the midst of my peak earning years, doubt about the future crept in. Could I really do something new? Would it work?

I fought back imposter syndrome by diving into learning new skills – project management and UX Design.

It wasn’t about adding credentials; it was about proving to myself I could adapt.

But the real breakthrough came when I stopped forcing my old skills into unfamiliar roles and instead focused on what felt like a natural fit. A little work with AI helped me uncover something I was overlooking – bookkeeping.

Turns out my equity analysis skills translated perfectly to helping small businesses understand their finances.

👍 Reinvention isn’t a detour; it’s a continuation of your purpose in a new form.

If there’s one thing I learned, it’s this: confidence to reinvent yourself and the patience to see it through is the secret weapon every founder, owner, or entrepreneur needs to embrace.

Reliability isn’t taught in classrooms.

I learned it standing in a hangar, staring at a mess nobody wanted to touch.

I was raised by a father who was a WWII Navy veteran. Reliability wasn’t a word in our house; it was the baseline for who you were expected to be.

However, reality set in when six massive aircraft pallets, full of jet parts, arrived in disarray. They were mine to fix.

For five months, I sorted, counted, rebuilt, and organized a War Readiness Spare Kit for F-16 fighter jets. At the time, I was the new guy and also the lowest-ranking member of the team. Hence, my assignment for the job. No help offered, no shortcuts, and zero complaints.

What I didn’t know? The kit was headed to Norway. When my supervisor picked who would deploy with it, he picked me.

The side eyes and grumbling about why the new guy followed.

My supervisor’s response has stuck with me to this day. He asked three questions.
↳ Who saw the new guy show up early and stay late? All hands went up.
↳ Who offered to help the new guy? No hands.
↳ Who heard him complain about the job? No hands.

He only added, “In my 10 years, I’ve never met anyone more reliable. His reliability is our unit’s reliability. Rank and time here doesn’t matter, reliability does.”

Real reliability isn’t about skill or titles, or who’s been around longest. It’s about showing up, especially when nobody’s watching.

And one day, someone will.

Everyone thought I was off my rocker for starting a business in the Great Financial Crisis.

Fall 2008. The financial world was collapsing. I was running a successful investment advisory office in DC with 100 clients and $90 million under management. Life was going well.

Then my corporate overlords started second-guessing trades that were made to protect my clients’ life savings. My overlords thought they knew better than me, the guy actually sitting across from the clients.

I refused. But I also started planning my exit.

The situation: My wife and I were expecting our third son. I had a 3-hour daily, round-trip commute that was killing me. All the while, we were in the midst of the worst economic environment in a century.

My wife’s vote? “ Stay put, this is crazy.”
My vote? “I’m going on my own.”
Final decision? I started my business.

I built everything from scratch on a shoestring budget. I taught myself web design, filed all the regulatory paperwork, and built my investing tech stack. When my son was born in the fall of 2009, the economy was still raw.

Then my old company sued me for taking clients.

So there I was: new business, new baby (3rd son), new lawsuit, and bills to pay. You know what I did? Swallowed my pride and took a night job at a restaurant for 10 months to keep cash flow coming while I built my business.

In real time, I looked like a complete idiot for leaving stability for chaos. Almost sank my marriage as well. But I was willing to bet on myself and busted my hump to make it happen.

The lawsuit was settled for the original terms of the non-solicitation I signed. A scant amount compared to what I gained in money and time.

Fast forward to 2021. The business I built merged with another entity in 2012, where I became a partner. We sold our wealth management business in July 2021 for a tidy sum. 👍

Along the way:
👶 I got to see my kids grow up.
✈️ Worked on my own terms.
🏦 Built something I was proud of.
💰 Achieved financial independence.

Lesson = The biggest career risks often look reckless until you’re viewing them in the rear view mirror.