22 Sept 2026
Greg Helbeck | From Hockey to Houses: Greg Helbeck’s Real Estate Journey
In this episode of Pucks to Properties, we sit down with Greg Helbeck, real estate investor, entrepreneur, and content creator, to talk about walking away from hockey at a young age, finding his path in real estate, and building a seven-figure business from the ground up.
Greg’s hockey career ended after junior hockey, when he realized that continuing to chase the game wasn’t going to lead where he wanted it to. At just 18 or 19 years old, he found himself back home, unsure of what came next and dealing with the identity shift that comes with losing the one thing he had spent his life pursuing.
That uncertainty ultimately led Greg to a real estate seminar, where he discovered the world of investing and decided to take action. With very little money and no real estate experience, he and a friend split the cost of the program, and within about nine months Greg completed his first deal—a wholesale transaction that earned him a $5,000 check. From there, he began steadily building his skills, experience, and business.
Greg shares what those early years actually looked like, including putting out 150–200 bandit signs every weekend, cold calling, learning how to find motivated sellers, and eventually developing a system around vacant and distressed properties. His business evolved from a one-person hustle into a company with a team, systems, technology, and roughly 40–50 transactions per year.
One of the biggest themes throughout the conversation is the idea of stacking skills. Greg explains how persistence, discipline, teamwork, taking direction from coaches, and learning to handle rejection in hockey gave him an unexpected advantage when he entered the business world. He also talks about why continually investing in your skills, marketing, systems, and education helped him transition from chasing individual deals to building an actual business.
Greg also breaks down how his real estate strategy has evolved. Today, his philosophy is “keep or flip the best and wholesale the rest,” allowing his team to evaluate each opportunity individually and determine whether to wholesale, hold, or renovate a property. He also shares how technology has completely changed the real estate landscape since he got started in 2015.
The conversation also dives into Greg’s growing YouTube channel, where he shares real deal breakdowns and lessons from the trenches, giving viewers an inside look at the transactions he is actually working on rather than simply discussing real estate theory.
And despite stepping away from hockey for nearly a decade, Greg eventually found his way back to the game. After rediscovering his love for skating, he now plays adult hockey several times a week in Seattle and sees the game differently after building a life and career outside of it.
From losing his hockey identity at 20 to building a successful real estate business, learning to embrace rejection, stacking skills, building a team, and finding his way back to the game, this episode is a conversation about reinvention, persistence, entrepreneurship, and finding your next chapter after hockey.
Connect with Greg:
Greg Helbeck- Real Estate Investing Fast Track (https://www.youtube.com/c/GregHelbeckREI)
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