My first job was in 6th grade - I was a busboy at Sam's Grill.
My best friend Danny and I would bike there after school, clear plates, roll silverware, help the cooks deal dime bags behind the dumpster.
Easy money.
But man oh man, that first paycheck—the way those crumpled bills felt in my pocket. That dopamine hit. That excitement. Some kids get it and some kids just don't.
My Dad may have recognized the spark in me. Maybe he saw himself in it, who knows.
So he did what any good Dad would do—he took me to Beneficial Bank on Lancaster Ave, the same Philly institution where he'd been loyally depositing his own money for decades.
Opening my first savings account didn't just give me a bank book; with it, I inherited his deeply rooted philosophy that equated saving with survival, his quiet obsession with financial security that bordered on paranoia, and the unspoken family doctrine that worth could be measured by how well you've prepared.
That bank book became my scoreboard.
Every neighborhood had its hustles, and my friends and I chased them all.
Snow shoveling, house painting, car washing, hoagie making.
I’m not sure I worked hard because of some noble, to-be-developed-later work ethic, or if it was more of an obsessive-compulsive desire to watch my bank account climb.
The subconscious need to see things move up-and-to-the-right.
Looking back, I see now that while some of this was me, a lot was learned behavior.
My Dad quite literally shaped me—he was the family hero, the sole breadwinner, the heartbeat of our household.
And my Pops was of course a product of his environment, and his father - growing up in poor Philadelphia, in a lower-class, work-before-play household with an immigrant-mentality. Pick yourself up by the bootstraps, etc.
So he did—he went to college, med school, Vietnam, came home a few fractured fingers later, and opened up shop as a dentist in the blue-collar, Italian neighborhood where his parents still lived.
His office was pure 70's fever dream—turquoise swivel chairs, oversized lamps, dog-eared magazines stacked in every corner. My mom worked the front desk, my sister and I did homework in the back as Dad drilled and filled.
He was there at sunrise, left after dark—sixty, seventy hours a week of other people's molars.
Then he'd come home, spread insurance forms across our kitchen table, and wage war against bureaucratic bullshit until midnight, muttering numbers under his breath like prayers.
If it sounded hard—it was.
But make no bones about it, he lifted us up into another stratosphere from where he came. We were solidly middle-class— by high-school, maybe even upper middle-class.
But no doubt it all wore on him.
He was almost always stressed, always grinding, always counting the wad of cash in his wallet.
Money in, money out.
And as a sensitive kid, I watched my Dad with cautious eyes—tracking his long hours, his countless steps.
I had this childhood fantasy of growing up to make 'millions', just so he could slow down, finally take a breath...so his shoulders might drop an inch from his ears.
And then years passed.
I went to college, started my career, went to grad school, started again.
The possibility of making good money - the fantasy of helping my Dad ease into retirement was starting to feel possible, almost within reach.
Then life did what it does: a brain aneurysm took him at 65, just a few years shy of the retirement he'd been counting down to his whole life.
No warning, no goodbye, no chance to rest.
In my grief, I doubled down on the only strategy I knew: make money, save money, rinse, repeat.
As if somehow, by accumulating enough, I could retroactively win a game that had already ended.
So I tried.
I worked hard. I was often in the right place at the right time. I stashed each bonus, each salary increase, each lucky break.
The numbers were tracked like an excel-sheet religion: invest everything, max the 401ks, watch the dollars march up-and-to-the-right. Always up, always right -the sacred direction of success.
Go go go.
The decades blurred. Each milestone triggered a new hunger—what felt like 'enough' at 25 was a joke at 30. What seemed impossible at 35 was inevitable by 40.
The faster I ran, the faster I could run.
Never did I really stop to question the obsession, the burning need to accumulate. The voice in my head just constantly whispering 'more.'
Until last year, I came up a bit for air.
By any normal relative measure, I'd 'made it'—I climbed from a 20-something worker bee to the C-suite at a billion dollar company, landed my dream gig as CEO, first at The Hustle and later at Hampton, building teams and a track record I was actually really proud of.
And Hampton was the dream—we had immediate distribution, solid backing, a chance to build the kind of community I knew founders craved.
I was surrounded by smart and ambitious people, & watching our numbers explode: zero to nearly $10M, a hundred members to a thousand, all in two years flat.
The kind of rocket ship every CEO dreams of.
On paper, this was it—the crown jewel, the peak, the final job I'd ride into the sunset.
But success has a funny way of showing you what you're willing to sacrifice for it.
The all-or-nothing personality that made me good at my job was starting to steal from everywhere else.
To me, it was obvious: there were no more dog walks with the wife, no coaching my son's flag football team, and long gone were bedtime stories and my presence on the weekends.
Even my texts had a ruthless priority system: work first, everything else, whenever.
Each small surrender added up to a larger absence.
The irony was clear: I was a good CEO on my way to being great, and I was a great father on my way to being good.
Two arrows moving in opposite directions.
But walking away from Hampton felt insane - this was the dream CEO job, as good as it gets.
This was literally the kind of opportunity my Dad—who worked six days a week his entire life—would have killed for.
Leaving something so good felt like betraying his legacy, turning my back on generations of pushing forward at all costs.
It felt like a fuck you to all the grinding, all the hustling that had come before me.
But as I sat with it longer, a different truth emerged...
My Dad was quite literally counting down the days until his retirement.
Not because he didn't love hard work, but because he loved being a father more.
If he'd had my chances, my opportunities, he would've closed his practice in a heartbeat. He would have grabbed his recently-discounted YMCA card, his bedside table full of DIY health books, and he’d never look back.
And here I was, staring at my beautiful life—amazing kids still young enough to want me around, a healthy wife, an aging mom who won't be here forever—and suddenly it felt crazy not to walk away.
The real dishonor would be missing the lesson my Dad's death taught me: truly, there is no promise of tomorrow.
That if given the opportunity to chill out a bit, to coach my son's team, to walk my daughter to the bus, to be more calm, more present, more proactive with the people I adore most in my life... if given that opportunity, you better fucking take it.
That each day is a gift.
And that I don't need another up-and-to-the-right chart, I just need time.
