100 in 100: Brendan Sheehan-Day 14

The Story

Brendan Sheehan was here before the name was on the wall. He joined in January 2013, just a few months after Prototype opened its doors, back when Wodify didn't exist, the 6am crew was building itself from scratch, and the playlist leaned heavy on Metallica. He hasn't left since.

Over 2,127 sign-ins. Thirteen years. Still showing up four to six times a week — including this week.

But the number that tells Brendan's story most completely isn't a sign-in count or a PR. It's something he said in his own words: "Of all the hours in my day, this is the one hour that I feel like I'm most present."

That's not a small thing for a man whose other 23 hours are accounted for. Brendan is the owner of Waymark Wealth Management, a financial planning firm based in Marlborough, MA — right in the heart of MetroWest — and one of Prototype's community business sponsors. He has a Harvard degree in psychology and a master's in financial planning from Bentley. He manages clients, runs a business, raises a family, and does it all in a world that, as he'll tell you plainly, has never been short on volatility.

From the Charles River to the 6am Class

Brendan grew up in Braintree, Massachusetts — self-described Irish Catholic blue collar, Eagle Scout, kid who ran track in high school and ended up at Harvard. Once there, a roommate pulled him toward the crew team, and Brendan decided he didn't want to be the coxswain — the little guy in the back. He wanted to be one of the big guys in the boat. So he rowed. Six days a week, indoor erg sessions before the river thawed, the kind of workout culture that leaves a mark on how you think about effort for the rest of your life.

Then college ended, and the structure disappeared. The big box gyms came and went. Life happened — career pivots, a growing family, a business to build. By 2012, with daughter number two arriving, he was in the worst shape of his adult life. He had plantar fasciitis bad enough that he couldn't stand up and rock his infant daughter without real pain.

"I remember saying: I wonder if this is what old feels like."

He started doing some personal training sessions at Boston Sports Club. Then Prototype opened. He walked in a few months later and found exactly what he'd been missing since his rowing days: a group, a standard, a reason to show up.

One Hour. Fully Present.

Ask Brendan why he keeps coming back — not just for months but for thirteen years — and he gives you an answer that cuts straight to the thing most people are actually searching for.

The gym is meditation. Not metaphorically. Functionally. When you walk in and a workout is written on the board, your brain has exactly one job. Not seventeen. One. And for someone who spends the rest of his day thinking about market volatility, client portfolios, behavioral finance, and all the weight that comes with being responsible for other people's financial futures — that one hour is irreplaceable.

"Instead of thinking about 17 different things at all times, during that one hour at the gym I get to hang out with my friends, have some laughs, and focus on one thing. It sounds counterintuitive, but it was almost like meditation — and that's what got me through some of the hardest periods of my life professionally."

He lived that truth between 2014 and 2018, when he was studying for the Series 24 — a brutal licensing exam — while simultaneously managing a stressful day-to-day at work and preparing to eventually take sole ownership of Waymark. The 6am class wasn't optional during those years. It was load-bearing.

The Planner Who Tells Clients: Don't Cancel the Gym

Here's the part of Brendan's story that's unique in the 100 in 100 series: he's not just a member who found fitness. He's a financial planner who has seen firsthand what happens to people when stress peaks and they start cutting the things that keep them sane.

He has clients who are also Prototype members. And when things get tight — a job loss, a kid heading to college, a rough market stretch — the gym membership is often the first thing on the chopping block. His response is always the same.

"I always ask them: there's not just the physical part of the gym, but there's also the social part. And if you stop paying that membership, is it going to impact you both physically and socially? And almost always the answer is yes. And it's almost always one of the things I actually tell clients — don't drop that."

Brendan has two degrees, and he'll tell you that right now his psychology degree is coming in more handy than the financial planning one. The core insight is the same in both worlds: behavior drives everything. In finance, the biggest risk isn't market volatility — it's what you do when you're scared. In fitness, the biggest risk isn't missing a week — it's the narrative that follows when you stop and can't find your way back.

"The first thing you tend to drop when stress peaks is your own health. And it's almost the exact opposite of what you should be doing."

Still Going. Still Growing.

Brendan's training data is a thirteen-year arc in numbers. First lift logged in the system: June 2013. Most recent PR: a 325-lb barbell hip thrust in December 2025. He's not winding down — the trend line goes the other way. His attendance has been climbing, with March and April 2026 coming in as his highest-volume months in recent memory.

Over the years the numbers compound: a 375-lb deadlift, a 207-lb clean, Fran in 4:33, a Murph completed, the CrossFit Open entered year after year. And every fall, Brendan returns to the Charles River for the Head of the Charles Regatta — a Harvard alum going back to the water where his athletic story first started. The photo he brought in for this story was taken there in 2023, the Charles River behind him, the Cambridge skyline in the distance. He's done it consistently. Some things you don't let go of.

That's the arc: Braintree kid rows at Harvard, loses the thread for fifteen years, finds it again in a gym in Westborough, and hasn't looked back since.

He also opened up a whole new set of friendships he never would have had otherwise. "I now have this whole new subset of friends that I never would have had without this place. As a Boston kid, you don't just make friends with people just because — but I have my Braintree friends, my Harvard friends, and now this whole other group I got here."