Blake Squires began his journey in the mid-90s in Los Angeles, capitalizing early on the convergence of technology and media. He soon returned to his hometown of Cleveland to co-found Everstream with Steve McHale (episode 196...
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 …
Leopoldo Peña — Co-Founder & CEO of Presta ($3.3 million raised) — on startups, his passion for expanding access to those who historically haven't had it, Cleveland's ecosystem, and the trials and tribulations of entrepreneurship — from failures to acquisitions.
Dallas Hogensen — CEO of Felux ($24mm raised) — on marketplaces, importance of culture, and creating the world’s largest operating platform and marketplace to help solve commerce for the steel industry.
Shawn Rech — Co-Founder/CEO/Director at Transition Studios, AGTV & TruBlu — on growing Cleveland's permanent media industry, the importance of factual programming and positively affecting history through truth-telling and documentary production!
Tom Tyrrell — founder and Chairman of Great Lakes Biomimicry & co-founder of Segmint — on the power of biomimicry and harnessing the intelligence found in nature’s 3.8 billion years of R&D (asking questions nature has already found the answers to)
John Wetzel, Alex Hilleary, Brooks Sime — Co-Founders of Gather — on building a company oriented around a future of work that puts people first and streamlines workflows for People Operations teams, and their journey from inception to acquisition by ChartHop
Nolan Gallagher — Founder and CEO of Gravitas Ventures — on building a global all rights theatrical distribution company that has released more than 3,000 films on Video on Demand (VOD) and has since been acquired by Anthem Sports & Entertainment in late 2021.
Drew Kraemer — CEO of Code3 & Founder of Marketplace Strategy — on building a digital performance marketing agency that serves some of the largest digital advertisers globally and the future of marketing across search, social, programmatic, marketplaces, and emerging channels.
Stan Garber & Alex Yakubovich — Co-Founders of Scout RFP (now known as Workday Strategic Sourcing) — on serial entrepreneurship and Scout RFP’s journey to acquisition by Workday for $540mm in 2019, where both of them still work leading Workday’s strategy and growth in the source-to-pay space.