151: Matt Gregory – Fast Tracking Future Leaders

Guest: Matt Gregory

Guest Bio:

Matt Gregory's story is one of quiet transformation, shaping the brokerage division from within while never losing the drive to help clients. A strategist and mentor, he co-founded the Office Brokerage Group, launched the firm's Fast Track training program, and has closed 1,200-plus deals worth more than $810 million. Clients value his mix of precision, urgency, and clear foresight; colleagues value his commitment to developing future leaders. Having recently earned his broker's license, Matt now serves NAI Ohio Equities in an official Management-Level Broker capacity, bringing even greater authority to the guidance he provides.

Education: BA Communication - The Ohio State University

Professional Affiliations: SIOR, CCIM

Matt continues to pair strategic vision with hands-on coaching, ensuring both clients and the next generation of brokers achieve their full potential.

Key Points:

Career Background & Path into Real Estate

While studying at The Ohio State University, he interned at Ohio Equities, helping modernize their marketing and tech systems. After graduation, he became Director of Information Technology for the firm. Over time, he was drawn into sales after assisting agents with listing presentations and realizing he enjoyed the client-facing, persuasive side of the business. Encouraged by the company's owner, Sandy Simpson, he got his real estate license and transitioned into brokerage.

View on Selling

Matt prefers to think of sales as education, advising, and consulting rather than traditional selling. His philosophy: "Educate clients so they can make confident, informed decisions." He defines selling as persuading someone of value, aligning with the dictionary meaning of "to sell." He believes in consultative selling—building trust through information, not pressure.

Fast Track Program (Training for New Agents)

Originally created in 2006, revived and redesigned in 2023 under his leadership. Matt discusses in depth the structure of the Fast Track Program he designed and uses to train new agents. The Goal: give three years of experience in one year to reduce new-agent failure and speed up success.

Hiring & Recruiting Philosophy

Matt looks for candidates who are confident but not arrogant, emotionally intelligent and adaptable, self-motivated and resilient, and realistic about the long sales cycle in commercial real estate. The recruitment process he uses is multiple conversations (3–4 meetings), both formal and informal, emphasis on intuition and relationship-building, not just testing, considers diversity in career stages and backgrounds (new grads, mid-career switchers, experienced professionals), and avoids personality assessments; it relies on observation and cultural fit.

Leadership & Management Style

Matt's biggest management challenge is balancing autonomy and oversight. He wants agents to feel empowered but not reckless. Some agents over-communicate; others under-communicate—he strives for a healthy middle ground. He focuses on mentorship, working directly on deals with new agents to model behaviors and decision-making. Matt encourages agents to become future leaders, not just team players.

Outcomes & Culture

Strong retention and development culture—agents tend to stay long-term. Emphasis on learning, collaboration, and shared success. Fast Track alumni are performing well and contributing to the firm's growth. The company's local reputation attracts new candidates organically.

Guest Links:

Website: https://www.ohioequities.com/brokers/mgregory.html

LinkedIn: https://www.linkedin.com/in/mgregoryohioequities/

Facebook: https://www.facebook.com/mjgreg

Twitter: http://www.x.com/officegrp

Instagram: http://www.instagram.com/officegrp

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