Venture Capital & Private Equity Episodes

What does it take for AI to matter inside a real operating business? Not as a demo, not as a dashboard, and not as a generic productivity tool — but as something that answers calls, reduces clicks, quotes freight, improves service, and helps people spend more time doing the work that actually moves the business forward. Today we're republishing an episode from The O.H.I.O. Fund Report with Mark Kvamme — co-founder, CEO, and CIO of The O.H.I.O. Fund — Peter Coratola, founder and CEO of EASE L...

This is the 250th episode of Lay of The Land, and to mark it, I wanted to do something a little different. Most episodes of this podcast are centered on founder stories — what drives someone to take the very difficult leap of trying to build a company, what problem they feel compelled enough to devote their life to solving, and what they learn along the way. But for this milestone episode, I wanted to step back and talk about the thing that ties these stories together… the community itself. A...

Will Zell — Founder and Managing Partner of Vessel, founding CEO and now Executive Chair of AssetWatch, and a leading voice in rethinking how venture capital works across Ohio. Will’s path into technology and venture isn’t conventional. He grew up — and still lives — in Bellefontaine, Ohio. At 17, he ran for city council under the slogan “A Voice for the Future.” He spent time in ministry, built a real estate portfolio during the financial crisis, and ultimately found his way into technology...

Scot Lowry — Managing Partner and Co-Founder of PromiseONE Companies Scot is the Managing Partner and Co-Founder of PromiseONE Companies, a Cleveland-based investment firm that helps purpose-driven entrepreneurs acquire and grow established businesses through Entrepreneurship Through Acquisition, or ETA. Prior to launching PromiseONE, Scot acquired and led Fathom, a digital marketing firm he grew more than 450% over a decade — an experience that became both the financial engine and talent inc...

Today’s episode was recorded live at Ohio VC Fest, where I hosted a panel on AI, joined by an incredible group of investors, including: Peggy Roberts, Managing Partner at The Riverside Company; Candice Matthews Brackeen, Founding Partner at Lightship Capital; Hardik Desai, Managing Partner at JumpStart Ventures; Jamie Weston, Managing Director at Spring Mountain Capital. Together, we walk through where real value is being created with AI, how founders can best leverage it in the...

Craig Newmark is the founder of Craigslist and someone whose work has shaped the modern internet as we know it. Long before Craigslist became one of the most enduring, important, and frequented platforms on the web, long before the internet even connected all of us, Craig was a computer science student here in Cleveland at Case Western Reserve University — tinkering with early programming languages, studying neural networks and AI, and exploring the frontier of software engineering. The res...

Brad DeHays — Founder and CEO of Connect Real Estate and Connect Housing Blocks. Brad’s journey spans from buying small distressed properties while still in college to leading one of the most ambitious housing manufacturing platforms in the country. Through Connect Real Estate, Brad has revitalized some of Ohio’s most overlooked landmarks — transforming abandoned power plants, trolley barns, and historic buildings into vibrant new community anchors. That same entrepreneurial vision inspi...

Chaya Slain is the Founder, President, and Chief Investment Officer at Virtera Partners. After studying mathematics at Columbia University, she discovered her deeper interest in investing at Goldman Sachs. After several years in New York, she returned to Cleveland and joined Parkwood, the Mandel family investment office, where she spent more than a decade immersed in institutional investing. At Parkwood, she developed a disciplined, process-driven investment philosophy; built relationships w...

On this special episode of Lay of the Land, I’m joined—for the first time—by the two co-founders of The O.H.I.O. Fund, Mark Kvamme and Ray Leach, as well as the fund’s two founding partners, Jill Meyer and Mike Venerable, to share the inside story of how a bold idea became reality. We explore the inspiration and origins behind a first-of-its-kind strategy designed to generate returns while accelerating prosperity and shaping Ohio’s future. We discuss how, in our first year, we closed on over...

Dale Wollschleger is the Founder and former CEO of Cleveland-based ExactCare Pharmacy and the developer of the ExactPack™—a patient-specific medication packaging system designed to simplify complex medication regimens. This O.H.I.O. Fund Report conversation with Dale dives into the unlikely journey of a pharmacist-turned-entrepreneur who started in the back of a small Cleveland pharmacy and built a billion-dollar organization serving patients across the country. ExactCare’s meteoric growth—fr...

TJ Dembinski is the co-founder and CEO of Eagle Electronics, dedicated to on-shoring America’s critical technology supply chain, starting with the IoT and automotive-grade cellular modules! This journey traces a fascinating arc — one that begins with the macro and geopolitical forces shaping global commerce and lands in a Northeast Ohio advanced micro-electronic manufacturing floor where Eagle Electronics is domestically building one of the most critical pieces of our digital infrastructure: ...

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) and Charlie Lougheed (episode 42, and also my co-founder at Axuall). Blake served as COO until Everstream’s acquisition by Concurrent Computer Corp in 2005. Next, he co-founded Findaway, a global leader in digital audiobook distribution and creators of PLAYAWAY, a line ...

Andy Tran has lived more lives than just about anyone I know. He’s a serial entrepreneur who has started multiple businesses across industries, including tech, ammunition manufacturing, defense contracting, and tequila, among many others. Andy is a true modern Renaissance man whose path defies convention and serves as a testament to his deep curiosity, creativity, ability to execute, and humility. He has alpine mountaineered in Patagonia and Tierra del Fuego while living out of the back of a...

Welcome to a special bonus episode of the Lay of The Land podcast. Today, we're doing something a bit different as I take on the role of guest on other podcasts to discuss recent developments in my journey and offer a glimpse of what lies ahead. As some of you may know, I've recently embarked on a new professional path by joining the founding team of The O.H.I.O. Fund. In the near future, I'll be recording a dedicated episode to delve deeper into The O.H.I.O. Fund alongside some of my part...

Hanna Kassis — founder @ Babylon Asset Management — who has deployed over $1.5 billion in capital throughout his career in alternative lending. Starting with Tim Ryan's congressional campaign in Youngstown, Hanna went on to build OAREX Capital Markets while still in law school, securing seed funding from Dan Gilbert's Bizdom and later an additional $100M in institutional credit, to build an innovative online ad revenue exchange. After a successful exit in 2022, he later launched Babylon Asset Management, recognizing an opportunity after the Silicon Valley Bank collapse. Under his leadership, Babylon has invested in 170 alternative loans and helped dozens of companies access growth capital. His entrepreneurial drive also led him to expand into new ventures, including acquiring and revitalizing Whistle Taproom (formerly Whistle & Keg), which has become a Downtown Cleveland premier game day destination. In this episode, we explore Hanna's journey from campaign manager to financi…

Welcome to a special bonus episode of the Lay of The Land podcast. Today, we're doing something a bit different as I take on the role of guest on other podcasts to discuss recent developments in my journey and offer a glimpse of what lies ahead. As some of you may know, I've recently embarked on a new professional path by joining the founding team of The O.H.I.O. Fund. In the near future, I'll be recording a dedicated episode to delve deeper into The O.H.I.O. Fund alongside some of my part...

Andrew Rising, CEO of Encore Ventures Labs. As someone who believes deeply in the opportunity for Cleveland’s future, I find Andrew’s journey to be an inspiring and optimisitc one… …Deeply rooted in the heart of Cleveland’s west side where he grew up before embarking on a decade-long adventure in the Bay Area—a place where innovation and venture capital converged to create world changing technologies. Andrew has spent his career at the intersection of talent and venture capital — from Google to...

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 Business in 2003 and moving to Cleveland, where they built and grew this e-commerce, specialist insurance company selling pet insurance directly to pet owners — from their first policy sold in October 2006 to insuring over 500,000 pets across the country and handling over 4.6...

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 career, most recently overseeing investment management, private banking, and Trust and Banking Services at Fifth Third Bank. Fifth Third Bank acquired Maxus Investment Group in 2001, which previously merged with Gelfand Partners Asset Management back in 1997, where Fred ser...

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 angel and venture investor through his fund Far Out Ventures, Jack runs a weekly newsletter called Buffalo Bridge which tells the stories of Buffalo’s startup community and has made nearly 200 investments in other founders and startups! Jack is the first guest to com...

Michael Sirpilla, co-founder and CEO of Society Brands. Under Michael’s leadership as CEO, Society Brands has raised $205 million in capital to continue their rapid consolidation in the e-commerce sector with many completed and successful acquisitions since inception. Society Brands, based in Canton, Ohio, is a tech-enabled consumer products company that acquires e-commerce native brands and powers them with a global growth platform, scaling and evolving them into household brands. They provi...

Stewart A. Kohl is Co-CEO of The Riverside Company — a $14 billion global private equity firm founded to invest in premier companies at the smaller end of the middle market, with headquarters in Terminal Tower in Tower City here in Cleveland! Since 1988, Riverside has invested in more than 960 companies globally, growing assets under management from $1 billion in 2004, to as much as $14 billion dollars under management today, employing more than 300 people in offices across North America, Eu...

Bill Manby, Founding & Managing Partner at Interstate Fusion Ventures. An entrepreneur at heart, Bill grew up in NEO and has always been passionate about working every day to make his home better through investments, philanthropy, and whatever else it takes. In late 2016, this vision led to the creation of his first fund – Akron Fusion Ventures (later rebranded as Interstate Fusion Ventures). While Bill knew the benefits of living in NEO and the strong entrepreneurial spirit, he felt he ...

Michael Goldberg, Executive Director of the Veale Institute for Entrepreneurship, as well as an Associate Professor of Design and Innovation at the Weatherhead School of Management at CWRU where he teaches courses on entrepreneurship. Notably, Goldberg created a massive open online course — also known as a MOOC — for CWRU called "Beyond Silicon Valley: Growing Entrepreneurship in Transitioning Economies", a course which has attracted over 175,000 students from over 190 countries across the w...