Meet the Kyles

Kyle K has extensive experience building, transforming, and leading services businesses. Prior to co-founding Harbour Heritage, he led operations, marketing, customer service, and transformation for nationwide, investor-backed healthcare companies. He previously advised Fortune 100 healthcare companies on innovative business models to better meet the needs of patients.

In 2024, he was named to Becker's Healthcare 40-under-40. He holds an MBA from Columbia Business School and bachelor’s degrees from the Univ. of Central Florida. 

He resides in his hometown, Tampa, FL, with his wife, Liz, and their daughter, Harlow. 

Kyle I has extensive experience investing in small and medium size businesses. Prior to co-founding Harbour Heritage, he was both an operator and investor for a holding company, building long-term value in businesses across nearly every industry. He has managed deals across sourcing, diligence, valuation, and negotiation.

He holds an MBA from The Wharton School of the University of Pennsylvania and bachelor’s degrees from the University of Edinburgh. 

He resides between Chicago and New York City.

An experienced network of investors & advisors bringing decades of operational & leadership expertise, transaction experience, and growth capital accessibility. Select profiles include:

• Fmr. Chair, Florida Chamber of Commerce; First non-family CEO, Large Retail
• General Counsel & Trial Lawyer, 15-time Best Lawyer in America
• Multi-time acquisition entrepreneur of founder-legacy businesses
• Entrepreneur turned investor with $300M+ of long-term hold transactions