Behind The Deal

In this episode, we sit down with Brian Dukes, founder of Exitwise, to unpack the real mechanics of selling a business in the lower-middle market—before an investment banker ever gets involved. Brian works hands-on with founders to help them understand value, prepare for liquidity events, and avoid the costly mistakes that derail outcomes long before a deal is on the table.

We dive into how Exitwise helps owners think clearly about timing, readiness, and optionality; the most common blind spots founders have when approaching a sale or recap; and how today’s buyers are underwriting risk in a more selective M&A environment. Whether you’re years away from an exit or quietly evaluating your options now, this conversation offers practical insight into how smart preparation drives better outcomes—and better leverage—when it’s time to transact.

In this episode we sit down with Ariez Dustoor of NB Group to go behind the curtain of lower-middle-market M&A and private equity investing. We dive into how Ariez evaluates founder-led businesses, structure transactions that align both seller and buyer incentives, and build sustainable value post-acquisition. If you’re an entrepreneur preparing for an exit, an investor looking at control or growth buy-outs, or an advisor seeking to understand what really matters in deal execution — this conversation offers real-world insight into how deals get done and how to partner for the long-term.

In this episode, we sit down with JR Gilley of Trinity Hunt Partners, a Dallas-based private equity firm focused on building market-leading service businesses through strategic acquisitions and hands-on partnership. JR shares insights on Trinity Hunt’s investment approach and how the firm helps founder-led companies scale through disciplined growth and M&A.

In this episode we speak with Todd Taskey of Tower Partners about the real mechanics of deal-making in the lower-middle market. We dive into how he advises business owners on positioning for acquisition, structuring deals to capture both upfront value and long-term upside, and what he’s seeing in the digital-services and transformation sectors. Whether you’re an entrepreneur thinking about your exit, an investor evaluating a buy-out, or a deal advisor navigating the process, you’ll get practical insights into how transactions really get done.

In this episode, we sit down with Scott Bartnick and Josh Bilmes of Oceans Equity to explore the underside of deal-making: How they source and evaluate targets, how they partner with founders and executives, and how they build growth engines post-acquisition. We talk shop on buy-outs, add-ons, management alignment, and value creation. Whether you’re a founder, investor or advisor, you’ll gain actionable insight into the deal process and what distinguishes successful private equity partnerships.

In this episode, we host Marc Utay, Founder and Managing Partner at Clarion Capital Partners, to dive deep into the art and science of middle-market private equity and structured credit. Marc shares lessons from over four decades in dealmaking: how he picks control investments, how Clarion balances growth vs risk, why the firm moved into the CLO/structured-credit space, and what being an independent player brings in today’s volatile financial environment. If you’re interested in PE deals, credit, deal structure, or scaling investment firms, this episode gives you first-hand insights. (ION Analytics)

Mike Bourgeois is a dealmaker and leader at Skyline Partners LLC, where he works on corporate development and growth strategies, helping technology-firms refine their business development, product initiatives, and sales expansion. He leverages long-standing relationships across lenders, transaction advisers, and management teams, with an orientation toward pragmatic scaling of portfolio companies through both stable and challenging market cycles.

In this episode, Joe sits down with Guillaume Lussato,  Associate Director of saas.group, to explore the world of SaaS acquisitions and growth. They discuss how saas.group partners with founders, the unique challenges of scaling B2B SaaS businesses, and what the future of dealmaking looks like in the software space. Whether you’re an operator, founder, or investor, this episode offers insights into the evolving dynamics of M&A in SaaS.

In this episode, we sit down with Joshua D. Wild, Managing Partner at The ELEVATED Companies, to dive into the inner workings of building a vertically integrated real estate business in Boston. JD shares his journey from home construction to launching elevated residential developments, talks about sourcing and executing luxury condo and multi-family deals, balancing the risk and rewards of development, and what it really takes to execute complex real estate transactions in today’s market. If you’re interested in real estate dealmaking, development, or scaling a full-stack real estate business, this episode has a lot to offer.