Success in running often comes from hitting rock bottom first. Terence Gerchberg knows this truth intimately. After losing everything to gambling addiction and sleeping on his sister's couch, he discovered that running could be the constant he desperately needed. Twenty-five years later, running hasn't just stayed in his life. It's become the foundation for everything else.

Terence's journey from addiction to 24 consecutive New York City Marathons to three Leadville 100 attempts reveals what sustainable excellence actually looks like: showing up consistently, finding community in the struggle, and redefining success as something far beyond finishing times.

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The story starts with a medal. Young Terence watched his Uncle Joey finish the Los Angeles Marathon and knew he wanted that experience. Years later, working on Wall Street and deep in gambling addiction, he'd pack running shoes for Vegas trips but never actually ran.

When he checked himself into gambling rehab in Baltimore, a friend called: they'd both gotten into the New York City Marathon. Terence had only run two or three miles. The timing was humbling but perfect. He joined a grassroots Nike run group led by Coach Kane, back when run clubs were just emerging in 2002, and the community embraced him in ways he desperately needed.

Growing up in Southern California, Terence always felt like a poser, wanting to skateboard and surf but never quite committing. When he started running, that feeling disappeared. You can't fake putting one foot in front of the other.

His first New York City Marathon was brutal with IT band problems and hobbling to the finish. The moment he stopped, he thought it was the worst thing ever, then immediately the greatest. He got in the next year and kept getting faster. Someone told him about Boston, and suddenly he had a new goal.

The streak began: 24 consecutive years of finishing New York. The consistency became proof he was building something sustainable.

Terence openly acknowledges his addictive personality. Gambling offered quick fixes; running offered delayed gratification and slow progress. His first 3.5-mile race took 28 minutes at eight-minute pace. He thought that was as fast as anyone could run. Then consistency dropped his pace through dedication rather than desperation.

Friends taught him to have fun. Chris, a low-2:40 marathoner, asked if Terence wanted to run Boston for fun (taking pictures, talking to people, stopping to enjoy it). Watching Chris go on to run 300 marathons and 100 ultras while enjoying the journey taught him what mattered: not the time, but who you connect with.

A decade into running, Terence discovered Back on My Feet, an organization that combats homelessness through running. The model is simple: meet at shelters every Monday, Wednesday, and Friday from 5:30 to 6:30 AM. Run, jog, or walk together. After 30 days of sobriety and consistent participation, members enter a program for financial empowerment, resume building, and job placement.

Terence thought he was giving back but quickly realized he received far more. Every volunteer session energizes rather than drains him. Members often don't believe people will show up week after week just to run with them without getting paid. The organization creates true community where you can't always tell who's a member and who's a volunteer. Everyone hugs or fist bumps, introduces themselves, runs together. No one runs alone.

Terence's ultra journey began through friendships with Chris McDougall and Scott Jurek, back before "Born to Run" made Scott a household name. His first ultra was the Old Pueblo 50-miler in Arizona. He studied winning times and figured he'd finish in seven or eight hours. Reality humbled him; he barely broke 11 hours.

Leadville became the white whale. Three attempts, three DNFs, each time making it to the halfway Winfield aid station before time cutoffs ended his race. His wife vetoed naming one of their kids Winfield.

But he keeps signing up. The race has punched him down three times, and he's going back. Not to prove anything, but because the challenge represents figuring out nutrition, cracking the code, training at sea level for high altitude. The perfect race doesn't exist, but the pursuit of improvement does.

Ask Terence what success means, and he won't mention sub-three marathons or Leadville buckles. He'll talk about his three kids growing up to be caring humans who give back. He'll mention his wife Rachel and continuing to grow together as partners.

Success is maintaining the New York City Marathon streak for life by training smart. It's being strong enough to pick up his kids and stay faster than them, at least for now. It's financial stability after knowing what having nothing felt like.

When his six-year-old son learned Terence's Boston time was three hours, he burst out laughing. The moment reminded Terence: it's not about the time. It's showing his kids that even when you fail — even when Leadville punches you down three times — you get back up and try again.

An older man at a bus stop in Ireland once asked Terence: "Why don't you runners ever smile?" The question stuck. Now Terence makes a point to smile while running, to say hello, to remember he chose this. Nobody forced him to sign up for marathons or ultras or volunteer shifts.

That mindset changes everything. Running becomes less about times and more about connections. How many people can you encourage along the way? That's where the real value lives.

Twenty-five years after that first New York City Marathon, Terence has learned what sustainable excellence means. It's showing up consistently, finding joy in the process, and using your story to help others write their own.

Listen on Spotify, Apple Podcasts, or other podcast platforms.

Jon is a runner, cyclist, and podcast host from Boston, MA, who now lives in Boulder, CO. For The Long Run is aimed at exploring the why behind what keeps runners running long, strong, and motivated.

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