JackQuisitions - Small Business Acquisitions in Home Service

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JackQuisitions - Small Business Acquisitions in Home Service

Jack Carr

36 episodes

4 days ago

In this episode of JackQuisitions, Jack sits down with Ian Smith, partner at South River Capital, to break down what it actually looks like to scale through acquisitions in home services—when the “platform” you thought you bought turns out to be pen, paper, and magnets on a board. Ian shares how his partners bought Terraform Landscaping in 2021 (~$2M revenue), then turned around and acquired an equal-sized landscaping company (Robins Landscaping)—only to learn the hard way that the owner was ...

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Entrepreneurship

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In this episode of JackQuisitions, Jack sits down with Ian Smith, partner at South River Capital, to break down what it actually looks like to scale through acquisitions in home services—when the “platform” you thought you bought turns out to be pen, paper, and magnets on a board. Ian shares how his partners bought Terraform Landscaping in 2021 (~$2M revenue), then turned around and acquired an equal-sized landscaping company (Robins Landscaping)—only to learn the hard way that the owner was ...

Show more...

Entrepreneurship

Episodes (20/36)

JackQuisitions - Small Business Acquisitions in Home Service

From $2.5M to $7M in 12 Months: Landscaping Roll-Up + Irrigation Acquisition Lessons

In this episode of JackQuisitions, Jack sits down with Ian Smith, partner at South River Capital, to break down what it actually looks like to scale through acquisitions in home services—when the “platform” you thought you bought turns out to be pen, paper, and magnets on a board. Ian shares how his partners bought Terraform Landscaping in 2021 (~$2M revenue), then turned around and acquired an equal-sized landscaping company (Robins Landscaping)—only to learn the hard way that the owner was ...

4 days ago

45 minutes

JackQuisitions - Small Business Acquisitions in Home Service

Watch This BEFORE You Buy/Start a Pressure Washing Business

In this episode of JackQuisitions, Jack breaks down why pressure washing is one of the most misunderstood businesses in America—and why the “low skill, low overhead, easy money” narrative is exactly what traps most operators in unscalable jobs. Jack explains how pressure washing looks simple from the outside, but in reality is a sales, marketing, and operations business disguised as a trade. He walks through the real cost structure most people ignore, why underpricing kills otherwise busy ope...

2 weeks ago

10 minutes

JackQuisitions - Small Business Acquisitions in Home Service

Is Rolling Up Alarm Companies the Best ETA Play in 2025?

In this episode of JackQuisitions, Jack sits down with Collin Trimble of Alarm Masters and Entry & Exit to dig into what it really looks like to roll up commercial fire and security companies—and why recurring monthly revenue (RMR) can be a cheat code for ETA operators. Collin walks through his jump from petrochem finance to security sales, then into Salesforce and revenue consulting, and finally into buying his own alarm company with longtime friend and partner, Steven. Collin breaks dow...

3 weeks ago

35 minutes

JackQuisitions - Small Business Acquisitions in Home Service

Your First Acquisition Will Probably Be Your Worst (Here’s Why)

In this episode of JackQuisitions, Jack sits down with Nathan Lindley of Done Right to dig into what it really looks like to roll up small HVAC companies—and why acquisition can be the smartest growth channel in the trades. Nathan shares his jump from Christian book publishing to home services, the “HVAC is non-optional” thesis that pulled him from Oregon to Dallas in early 2020, and why he knew his first deal would be his worst. They get into the gritty middle: buying tiny mom-and-pops out o...

1 month ago

38 minutes

JackQuisitions - Small Business Acquisitions in Home Service

Should YOU Buy a Business or Build One First?

In this episode of JackQuisitions, Jack sits down with Stephen Olmon to unpack one of the spiciest ETA questions out there: should you buy a business or build one first? Stephen shares his non-traditional path into entrepreneurship—from a pastor/teacher household to telecom consulting, then into the world of software, NewCo businesses, and eventually acquisitions. They dig into Stephen’s early failed independent sponsor deals, how those bruises shaped his approach, and why he ultimately went ...

1 month ago

32 minutes

JackQuisitions - Small Business Acquisitions in Home Service

Buying a Business: How Entrepreneurs Build Real Deal Flow

In this episode of JackQuisitions, Jack sits back down with Chris Barr to talk about what real leverage looks like in a self-funded search: building systems instead of just refreshing BizBuySell, working your broker network, and turning your geo + niche into an actual acquisition brand. They break down how Chris is rebuilding his search infrastructure after round one, why tech leverage (CRM, scraping, cold outbound) matters more than you think, and how conferences, LinkedIn, and local presenc...

1 month ago

31 minutes

JackQuisitions - Small Business Acquisitions in Home Service

Why No One Is Looking at Septic… and How to Buy One Cheap

Buying a septic company is one of the highest-ROI moves in home-service M&A… if you know where to look. In this episode of JackQuisitions, Jack breaks down exactly where real septic deals come from — from the obvious online marketplaces to the off-market gold mines almost no one talks about. If you’re serious about buying your first septic business (or adding one as a high-margin tuck-in), this roadmap will save you weeks of searching and tens of thousands of dollars. Jack covers why sept...

1 month ago

7 minutes

JackQuisitions - Small Business Acquisitions in Home Service

The Biggest Red Flags in Home Service Acquisitions

Buying a company is hard. Buying a job by accident is worse. In this roundtable, John Wilson (Owned & Operated) and Jack Carr break down the biggest red flags they’ve seen across nine-plus home-service acquisitions—from septic and trash routes to HVAC, plumbing, and electrical. They dig into the “is it a business or a gig?” test, how to sniff out customer concentration that’s hiding in plain sight, why low gross margin is the one warning sign you should never ignore, and the leaders...

2 months ago

37 minutes

JackQuisitions - Small Business Acquisitions in Home Service

From a $15K Acquisition to an $8M Home Service Business (In Just 14 Months)

Today on JackQuisitions, Jack talks with Dustin Marx, founder of Mother (Modern Plumbing) — the Texas-based plumbing company that went from $15K a month to an $8M run rate in just 14 months. Dustin isn’t your typical plumbing entrepreneur — he’s a former tech founder who turned a small, two-person shop into a fast-scaling, culture-first powerhouse. In this episode, he breaks down how he found his first acquisition through a podcast, why brand and mission matter more than ever, and how a 50% p...

2 months ago

36 minutes

JackQuisitions - Small Business Acquisitions in Home Service

How to Build a Security Company That Actually Closes New Deals (Entry & Exit Feed Drop)

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...

2 months ago

54 minutes

JackQuisitions - Small Business Acquisitions in Home Service

How Regular People Get Rich Buying Boring Businesses

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...

2 months ago

32 minutes

JackQuisitions - Small Business Acquisitions in Home Service

#25 Watch This BEFORE You Buy/Start an HVAC Business

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 ...

2 months ago

11 minutes

JackQuisitions - Small Business Acquisitions in Home Service

#24 What NOBODY Tells You About Being an Entrepreneur!

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...

2 months ago

35 minutes

JackQuisitions - Small Business Acquisitions in Home Service

#23 Would You Buy This? $2M Pool Business vs. 221 ATMs

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...

3 months ago

44 minutes

JackQuisitions - Small Business Acquisitions in Home Service

#22 Why Most Plumbing Businesses Get Stuck at $1 Million!

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...

3 months ago

47 minutes

JackQuisitions - Small Business Acquisitions in Home Service

#21 What Happens When Your Boss Is Younger Than You?

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...

3 months ago

16 minutes

JackQuisitions - Small Business Acquisitions in Home Service

#20 What We Wish We Knew Before Our Business Journey

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...

3 months ago

15 minutes

JackQuisitions - Small Business Acquisitions in Home Service

#19 Is Buying A Small Business Worth It In 2025?

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...

4 months ago

32 minutes

JackQuisitions - Small Business Acquisitions in Home Service

#18 SBA Acquisition Gone Wrong? Here’s Why the Deal Collapsed

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...

4 months ago

37 minutes

JackQuisitions - Small Business Acquisitions in Home Service

#17 From a Truck to $10M+ HVAC Empire

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...

4 months ago

39 minutes