John Knific is a serial entrepreneur and investor who has built three venture-backed software companies here in Cleveland. His latest venture, Squad, is a peer discovery platform designed to gamify ratings and rankings for Ge...
Stephen McHale — a long-time Cleveland serial entrepreneur with a 40-year career founding, investing in, and building companies. Most notably, Steve served as Chairman of the Board and Chief Executive Officer of Explorys, whi...
Joe Pulizzi is a serial entrepreneur and deeply passionate about all things content marketing and entrepreneurship — he is the bestselling author of seven books including Content Inc. , selling over 500,000 copies worldwide w...
Laura Bennett and Alex Krooglik, co-founders of Embrace Pet Insurance, which was sold in 2023 for $1.5 billion to JAB Holding Company. The duo founded Embrace Pet Insurance after graduating from Penn’s Wharton School of Busin...
Fred DiSanto, Chairman and CEO of Ancora — the Cleveland-based investment firm with nearly $10B in assets under management and over 100 employees — which he’s led since 2006! Before Ancora, Fred had an expansive investing car...
Matt Buder Shapiro — Chief Marketing Officer at Vytalize Health, Previously Founder at MedPilot (Acquired) I first spoke to Matt on this podcast 3 years ago. At the time, as a co-founder and chief marketing officer of MedPilo...
Azadeh Hardiman — Business Leader of Level20, the new business incubator of Progressive Insurance, one of the largest insurance carriers in the US (which was founded and still headquartered here in Cleveland)! As the new busi...
Jim Pshock , Founder of Bravo Wellness, which he successfully exited to Medical Mutual in 2020. After 20 years working in the insurance industry, Jim observed a need and a niche for employee wellness incentives, as health cla...
Gerald Hetrick (CEO of Docket (formerly Bezlio) & Professional EOS Implementer) Gerald has been on the show once before; those of you who’ve been with Lay of The Land from the beginning may recall Gerald as one of the first e...
Jack Greco, co-founder and former CFO and COO of ACV Auctions, a Buffalo-based wholesale online marketplace for cars (ACV Auctions went public in 2021 and is currently valued at approximately $3 billion dollars) Now an active...
David Levine — Co-Founder/CEO @ Wireless Environment (Acquired by Ring, Acquired by Amazon) & Co-Founder/CEO @ My Home Park Having made a career of invention and serial entrepreneurship, in 2005 David Co-Founded Wireless Envi...
John McKenna, CEO of Peachtree VA, a virtual assistant staffing organization & President of The Emerald Group, a premier mortgage recruiting firm. Based here in Cleveland, John acquired Peachtree VA early in 2022 to grow thei...
Mitch Kroll, co-founder & CEO of Findaway (acquired by Spotify). Mitch started Findaway back in 2004, a time when audiobooks were available only on CD and cassette, in order to revolutionize this business of audiobooks, conne...
Michael Crawford — Chairman of the Board, President, and CEO of the Hall of Fame Resort & Entertainment Company, which he joined in December of 2018. The Hall of Fame Resort & Entertainment company is a publically traded orga...
Kris Snyder — founder of Vox Mobile and Impact Architects & Head of Finance and Partnerships at Ninety.io — on working with entrepreneurial leaders to create impact and pursue a world where small and medium organizations and their employees can become more humane, productive and resilient in order …