MORE Entry & Exit Hosts Stephen Olmon and Collin Trimble get practical and tactical on winning new logos in security & life-safety. They break down how to niche your ICP, keep your message consistent, split lead vs. sales process, and get multithreaded so you close more deals—without wasting budget on broad, unfocused marketing. From anchor pricing and social proof snapshots to CRM must-haves, this is the field guide to predictable pipeline and higher close rates. ✨ What You’ll Lear...

Should you stay sector-agnostic in ETA (entrepreneurship through acquisition) or plant a flag with a clear buy box brokers, CPAs, and attorneys can remember? After a month sidelined by a home flood, searcher Chris Barr returns to his acquisition entrepreneurship journey—refining a small-business acquisition thesis around B2B services, GovCon janitorial contracts, and Florida/Palm Beach deal sourcing. We dig into search fund tactics, on-market and off-market pipelines, broker outreach, list sc...

Should you start an HVAC business in 2026? This business is hot—sometimes literally—and it’s vital to most Americans. In this episode of JackQuisitions, Jack breaks down what it really takes to start or buy an HVAC company in 2026: how much it costs, what kind of money you can actually make, and why HVAC might be one of the most durable trades to own right now. From licensing and startup costs to cash-flow management, staffing, and seasonality, this one gets brutally honest. If you’ve ...

In this episode of JackQuisitions, Jack flips the mic to bring on seasoned operator, investor, and podcast host Michael Crow. From beating stage four cancer in his 20s to building a 5,000-unit real estate portfolio and then diving headfirst into HVAC and plumbing, Michael shares a frank, field-tested playbook: compounding > flipping, shoulder seasons test your soul, and “permanent equity” works best when you actually plan to hold. They dig into franchise vs. independent, concentration risk...

In this episode of JackQuisitions, Jack flips the mic to bring on… JackQuisitions favorite and Owned & Operated’s own John Wilson. Together they break down two real deals in Ohio: a premium pool service route in Northeast Ohio and a 221-ATM route in Franklin County (Columbus). They dig into seasonality, margins, route density, and the very real difference between buying a cash-flowing job vs. a scalable business. If you’re weighing service routes, LSA arbitrage, or sticky B2B contracts (Y...

In this episode of JackQuisitions, Jack sits down with Patrick Lange of Business Modification Group to unpack what really drives (and drags down) HVAC and plumbing valuations. Patrick has sold 149+ trades companies and shares straight-talk on multiples, owner bottlenecks, service vs. construction mix, and how buyer profiles—and the June SBA SOP changes—are reshaping deals. If you’re eyeing an exit (or your next acquisition), this one’s a masterclass in reality over rumor. Patrick explains why...

In this part two, Jack sits back down with Chris Cisneros of Diamond Plumbing—this time diving deep into acquisitions, market entry strategy, and leading seasoned techs as a 23-year-old service manager. Live from the Miami Meetup, they unpack how to decide between greenfield vs. acquisition, what it really takes to keep teams post-close, and how to think about radius, logistics, and install crews when you’re expanding into Palm Beach County from Miami–Broward. They talk real risks (like “ever...

In this episode of JackQuisitions, Jack sits down with Chris Cisneros of Diamond Plumbing live at the Miami Meetup. Chris shares his incredible journey from selling marketing services door-to-door at just 13 years old to building a fast-growing plumbing business alongside his father. What started with one truck and a thrift store breakroom office has now expanded into a multi-truck operation with a warehouse, a growing team, and lessons learned the hard way. Chris opens up about the struggles...

In this episode of JackQuisitions, Jack sits down in Akron, Ohio with Matt, who just closed on his very first acquisition: a 75-year-old HVAC and refrigeration company outside Pittsburgh. Fresh off the Breaking $5 Million workshop, Matt walks through the whirlwind of his first six weeks as an owner—what it’s like to take on a $2M deal, why he valued stability over chasing top-line growth, and how he’s transitioning from a career in big tech and Amazon Web Services to running a boots-on-the-gr...

In this episode of JackQuisitions, Jack catches up with Chris Barr, who returns with a hard but valuable update: his most recent deal is officially dead. After months of diligence, capital invested, and a strong connection with the sellers, Chris made the tough call to walk away when the risk profile jumped too high. What could have been a dream business became a cautionary tale about what happens when books don’t line up, multiples stop making sense, and the juice just isn’t worth the squeez...

In this episode of JackQuisitions, Jack sits down with Jeff Bates, a Michigan-based operator who went from running trucks in the heat to owning and growing multiple HVAC companies. After years at Lennox and a crash course in small business while working for his father-in-law’s trucking company, Jeff and his partner decided to jump into ownership themselves. Their first deal came in 2022 with RNL Heating & Cooling, a legacy business with real estate included. But the story didn’t stop ther...

In this episode of JackQuisitions, Jack sits down with Matthew Railla, a former wine industry operator turned termite company owner. After years running his family’s winery, Matt discovered business brokerage through his brother-in-law—and eventually listed a highly profitable termite inspection company. When buyers kept passing due to its relationship-driven, project-based model, Matt had a realization: What if I bought it myself? From that October 2023 “aha” moment to closing in June 2024, ...

In this revealing episode of JackQuisitions, Jack sits down with his good friend Scott Horman, who attempted to build an HVAC business from the ground up. Just ten months later, the doors closed for good. Scott opens up about the hard truths—misaligned partners, poor service quality, and unpredictable lead flow—that ultimately sank the venture. If you’ve ever wondered whether to start a trades business from scratch or buy an existing one, this is a must-watch. 💡 What You’ll Learn: Why choosi...

📉 Lessons From the Trenches: The Real Cost of a $1.9M Plumbing Acquisition In this brutally honest episode of Owned and Operated, John sits down with Jameson Wildwood, who bought Sweetwater Plumbing in North Carolina for $1.9 million. Six months post-close, Jameson reveals what actually happened—from bad deals and cultural clashes to scaling a service division 5X in half a year. If you're eyeing a plumbing or trades acquisition, this one’s a must-watch. 💡 What You’ll Learn: The hidden o...

In this episode of Jackquisitions, Jack sits down with Alan Peterson from First Internet Bank to demystify the world of SBA lending for business acquisitions. Alan shares what most acquirers miss when evaluating loan options—including why gut instinct matters just as much as financials, how to approach deals with transparency, and when to prioritize prequalification over perfection. Whether you're exploring the 7(a), 504, or SBA Express, Alan breaks down the programs in clear terms—and how to...

In this episode of Jackquisitions, Jack sits down with Chris Barr—an aspiring business owner deep in the trenches of due diligence after signing an LOI to buy his dream company. What follows is a transparent, tactical breakdown of the financial, legal, and operational hurdles Chris is facing. From recasting sketchy financials to prepping for a potential retrade, this episode strips away the romanticism of acquisition and lays bare the gritty work that goes into closing a deal. If you're...

Buying a service business with the idea of passive income? In this episode of Jack Acquisitions, host Jack interviews Thomas Beebe, a financial advisor who stepped into ownership of his family’s HVAC company. What started as a hands-off investment quickly turned into a hands-on leadership journey. From remote team management to turning around a messy acquisition, Thomas shares the tactical decisions, operational missteps, and growth strategies that shaped his perspective on what it really ta...

Want to buy a small business using smart deal structures like earnouts, seller financing, and low-risk offers? In this episode of Jackquisitions, host Jack Carr sits down with Chris Barr, a first-time buyer navigating the ups and downs of business acquisitions—from walking away from bad fits to crafting a $900K cash-plus-earnout offer for a pressure washing company. Learn how Chris is sourcing off-market deals, avoiding shady broker tactics, and building a personal brand that attracts sellers...

Buying a small business? In this episode of Jackquisitions, we follow Chris Barr’s journey to acquiring a pressure washing company using smart financing—combining cash, earnouts, and trusted advisors. From submitting the LOI to executing deep-dive due diligence, Chris shares what it really takes to close a successful acquisition. You’ll learn how to build the right team, evaluate financials and legal risks, and structure a deal that fits your vision. Whether you're just exploring acquisitions...

In this episode of Owned and Operated, we’re diving into real-world strategies for sourcing and securing small business acquisitions. From outreach to private equity firms to using freelancers for off-market deals, we break down how acquisition entrepreneurs are getting creative and staying competitive. We explore how personal branding can help attract brokers, how to craft a buyer persona that actually stands out, and how Chris Barr is navigating live negotiations for niche businesses—includ...