Meet the people behind Pinnacle, making an impact every day in Central New York.

This video series brings you inside the Pinnacle Family of Companies through real, unscripted conversations led by former Syracuse University Men’s Basketball Coach, Jim Boeheim. Each episode highlights the individuals behind the work—diving into their stories, perspectives, and the impact they’re making across our community.

Blending insight with personality, these conversations go beyond business to showcase what drives our team, how they think, and what it truly means to be part of Pinnacle.

New episodes monthly!

Episode 2: Mike Schmidt

In this episode of Playing to Win, former Syracuse Basketball Coach Jim Boeheim sits down with Mike Schmidt, CEO of Bent Ear Technology Partners, to discuss cybersecurity, technology strategy, and why defense is just as important in business as it is in basketball.


Drawing on parallels between building a championship team and protecting an organization from cyber threats, Mike shares insights on cybersecurity preparedness, the growing risks facing small businesses, and the importance of partnering with experienced professionals to stay ahead of evolving threats. The conversation also explores technology planning, business growth, and how organizations can build a stronger foundation for the future.


Episode 1: Mike Figler

In this episode of Playing to Win, former Syracuse Basketball Coach Jim Boeheim sits down with longtime friend Mike Figler, Senior Vice President & Portfolio Manager at Pinnacle Investments, for an honest and entertaining conversation about investing, planning for the future, and navigating risk over time.


Drawing parallels between coaching and portfolio management, Jim and Mike discuss the importance of having a long-term strategy, avoiding emotional decision-making, and understanding the value of working with experienced professionals you trust. The conversation touches on diversification, market timing, aggressive versus conservative investing, and why starting early,even with modest amounts, can make a meaningful difference over time.


With their signature back-and-forth humor and decades-long friendship on full display, the episode balances practical financial insight with personal stories, including reflections on early career earnings, fundraising memories, and the mindset required to “play to win” both on the court and in life.