What if real success isn’t loud, flashy, or viral — but patient, disciplined, and built with family at the center?

That’s exactly what this week’s conversation with Jordan DePuy reveals. Jordan is a longtime banking professional in the Hudson Valley who has quietly built an impressive portfolio of side businesses while maintaining a full-time career, raising a family, and staying grounded in values that too often get lost in entrepreneurship.

Jordan’s story is a reminder that wealth doesn’t have to be rushed — and freedom doesn’t have to come from burning everything down.

A Banker by Accident — An Entrepreneur by Observation

Jordan didn’t grow up with money. In fact, he grew up hearing “we can’t afford that” more times than he can count. That experience sparked two lifelong interests: helping people and understanding money.

After realizing medicine wasn’t his path, Jordan studied finance and entered banking — learning the business from the inside out. Over the years, he noticed a pattern: the people who built real wealth weren’t just earning salaries… they owned businesses.

That realization planted the seed.

Growing a Side Hustle the Smart Way

Jordan and his brother started an ATM business with just a handful of machines and a modest investment. They didn’t chase hype. They reinvested profits, built reserves, and planned for growth.

Today, that business has grown to over 80 machines, alongside real estate investments and other ventures — all while Jordan continues working full-time in banking.

The key wasn’t speed.
It was systems, patience, and preparation.

And when COVID hit, that preparation mattered. The downturn exposed gaps, reinforced the importance of reserves, and reshaped how Jordan thinks about risk — lessons he now brings into every business decision.

Seeing Opportunity Through Patterns, Not Hype

Because Jordan reviews business financials daily, he’s developed an eye for opportunity most people don’t have. He looks past surface-level excitement and focuses on fundamentals: cash flow, sustainability, risk, and margin.

That perspective also makes him a better advisor. Whether he’s underwriting loans, mentoring entrepreneurs, or helping a personal trainer land their first clients, Jordan approaches growth practically — not emotionally.

One powerful theme throughout the episode: opportunity favors preparation. Empty machines, poor systems, or lack of planning aren’t just mistakes — they’re missed chances.

Life, Loss, and Leading With Empathy

The conversation takes a deeper turn when Jordan shares the loss of his mother during COVID. That experience reshaped his priorities and reinforced why he builds the way he does — not just for profit, but for people.

It also made him a more empathetic leader and banker. Jordan understands that numbers don’t always tell the full story — and that sometimes belief, integrity, and timing matter just as much as spreadsheets.

Lessons for Side Hustlers & Builders

Jordan’s advice for anyone building something on the side is simple but powerful:

• Know why you’re building
• Plan for both failure and success
• Build reserves before you need them
• Learn business fundamentals early
• Find mentors who’ve lived it
• Don’t sacrifice integrity for speed

When asked what he hopes people say about the way he built his businesses, his answer was immediate:

Ethical.
Integrity.