#218 Why $20M Doesn’t Mean You’ve Made It

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 or in the weeds of a deal, this episode offers an insider’s look at getting a service business acquisition across the finish line.⚡ What you’ll learnWhat Chris looked for in an ideal pressure washing business—and how he sourced itThe creative structure behind his LOI and financing approachWhy specialization matters: How Chris leveraged his real estate pros for M&A successThe step-by-step due diligence checklist across financial, legal, and operational domainsHow to avoid major pitfalls in banking and legal negotiationsThe must-have advisors you need on speed dial when buying a businessHow to evaluate seller-provided info and spot red flags before it’s too lateIf you’re buying a local service business or scaling your portfolio, this episode gives you a framework to approach acquisitions confidently—with the right strategy and team in place.👤 Hosted by: Jack Carr   👤Episode Guest:Chris Barr  💼 Shoutout to Appletree Business Services HVAC and plumbing pros—ditch tax surprises and unresponsive accountants. Appletree handles your books, taxes, payroll, and acquisitions, and they know tools like ServiceTitan cold.🎁 Get a free tax & financial review or 10% off a QOE report. 👉 Book a call here — tell Patrick Jack sent you.💼 Special Thanks to First Internet Bank! Looking to buy or expand a business? First Internet Bank is a National Preferred SBA lender specializing in acquisitions for the skilled trades. Their SBA loan program offers up to 90% financing for business acquisitions, partner buyouts, and commercial real estate—plus optional lines of credit to fuel future growth. Unlike traditional lenders, they take a “how can we” approach, making deals happen for both first-time buyers and experienced operators.👉 Special Offer: Mention Owned and Operated for a reduced good faith deposit and a complimentary deal review + buyside prequalification.Connect with Alan Peterson from First Internet Bank here to get started Send Us Mail!More Ways To Connect with O&O John's YouTube Channel Weekly Newsletter Leave a Review John Wilson, CEO of Wilson CompaniesJack Carr, CEO of Rapid HVAC📌 Disclaimer:Some links may include UTM parameters for tracking. Episodes may feature paid sponsors, but all opinions are our own. Always do your own research before making business decisions.

In this episode of Owned and Operated, John and Jack unpack what leadership looks like inside a $20–40 million home service business—and why that size still feels small. They explore how companies in this range often remain personality-driven, even with impressive revenue, and what it really takes to level up. From forming HR and marketing departments to structuring a true senior leadership team, they dig into the growing pains and leadership gaps most businesses face on the way to maturity.The conversation dives deep into leadership development, internal promotions, and when to hire key external roles like controllers. John and Jack share why the sophistication of a business doesn’t always match the revenue—and how building the right team early creates long-term stability and growth. If you're scaling past $10 million and thinking about what’s next, this episode lays out a real-world playbook for building a well-rounded, leadership-driven operation.🔹 In This Episode, We Cover: What leadership looks like at $20–40M in revenue Why revenue doesn’t always equal business sophistication The challenges of building a senior leadership team Promoting internally vs. hiring externally When to build HR, marketing, and finance departments How leadership development programs drive retention and growth Creating a stable, mature business beyond personality-driven leadership🌐 More resources💼 Shoutout to Quick Staffers LLC Need trained HVAC & plumbing CSRs at a fraction of the cost? Quick Staffers LLC specializes in placing top-tier global talent with the best SOPs and scripts. 🔥 Get $1,000 off your first placement here 👤 Hosted by:John Wilson Jack Carr Send Us Mail!More Ways To Connect with O&O John's YouTube Channel Weekly Newsletter Leave a Review John Wilson, CEO of Wilson CompaniesJack Carr, CEO of Rapid HVAC📌 Disclaimer:Some links may include UTM parameters for tracking. Episodes may feature paid sponsors, but all opinions are our own. Always do your own research before making business decisions.

In this episode of Owned and Operated, John and Jack return to the studio to tackle the real-world challenges of running a successful HVAC business during peak summer heat. They dive into how weather-related service demand, infrastructure upgrades, and a mature home service team contribute to record-breaking weekly revenues and improved operational efficiency.Discover how HVAC businesses can scale profitably by investing in technician retention, labor-saving automations, and strategic overseas staffing. John and Jack break down the processes that drive high performance—from sales training to data-driven decisions—all on the path to hitting their first $1 million in EBITDA and a $10 million annual revenue goal.🔹 In This Episode, We Cover: How scorching weather exposes weak HVAC infrastructure Building mature teams and repeatable procedures for scale Tracking metrics weekly to hit revenue and EBITDA milestones Streamlining sales processes & technician training for efficiency Leveraging data, automations, and overseas staff to cut costs Creating an environment that keeps top technicians around The roadmap to $10 million in revenue—next-year outlook🌐 More resources 💼 Special Thanks to Service Scalers!We’ve been partnering with Service Scalers to maximize our Local Service Ads (LSAs) and optimize our Google My Business profiles, and the results have been incredible. With hundreds of thousands in sales and 900+ calls in a single week, GMBs are now our top-performing organic lead channel. Want to learn how Service Scalers can do the same for you? 🔗Check Them Out Here 💡 Special Thanks to Modernize! We've been using Modernize for our water quality leads, and it's been a game-changer. If you’re serious about growing your business with better water quality leads, HVAC leads, or home improvement leads, check them out: 🔗 Get Quality Leads Here 👤 Hosts:John Wilson Jack Carr Send Us Mail!More Ways To Connect with O&O John's YouTube Channel Weekly Newsletter Leave a Review John Wilson, CEO of Wilson CompaniesJack Carr, CEO of Rapid HVAC📌 Disclaimer:Some links may include UTM parameters for tracking. Episodes may feature paid sponsors, but all opinions are our own. Always do your own research before making business decisions.

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. You’ll get a behind-the-scenes look at how new acquirers can finance service businesses, evaluate seller terms, and structure deals that actually close. If you're buying a business or scaling through acquisition, this episode is packed with actionable insight.⚡ What you’ll learnWhy Chris walked away from an art-framing shop that didn’t fit his criteriaHow a pool-route deal fell through—and the red flags you should watch for with brokersThe numbers behind a $900 K cash-at-close + earnout offer for a thriving pressure-washing businessProven frameworks for earnouts, seller notes, and revenue-share agreements that reduce risk and align incentivesTips for building a credible personal brand (see his Quick Staffers journey) to source off-market dealsStep-by-step due-diligence tactics, valuation shortcuts, and negotiation language you can use todayWhen to pivot, when to persist, and how to decide if a deal really moves the needleWhether you’re a first-time buyer, an operator expanding a portfolio, or a service-business owner curious about exits, this conversation is packed with actionable M&A strategy, deal structuring hacks, and outreach scripts that close.👤 Hosted by: Jack Carr  👤Episode Guest Chris Barr 💼 Shoutout to Quick Staffers LLC Need trained HVAC & plumbing CSRs at a fraction of the cost? Quick Staffers LLC specializes in placing top-tier global talent with the best SOPs and scripts. 🔥 Get $1,000 off your first placement here💼 Special Thanks to First Internet Bank! Looking to buy or expand a business? First Internet Bank is a National Preferred SBA lender specializing in acquisitions for the skilled trades. Their SBA loan program offers up to 90% financing for business acquisitions, partner buyouts, and commercial real estate—plus optional lines of credit to fuel future growth. Unlike traditional lenders, they take a “how can we” approach, making deals happen for both first-time buyers and experienced operators.👉 Special Offer: Mention Owned and Operated for a reduced good faith deposit and a complimentary deal review + buyside prequalifiSend Us Mail!More Ways To Connect with O&O John's YouTube Channel Weekly Newsletter Leave a Review John Wilson, CEO of Wilson CompaniesJack Carr, CEO of Rapid HVAC📌 Disclaimer:Some links may include UTM parameters for tracking. Episodes may feature paid sponsors, but all opinions are our own. Always do your own research before making business decisions.

In this episode of Owned and Operated, we’re exploring how to grow your career inside a home service company. From internal promotions to mindset shifts, John and Brandon Niro break down what it really takes to move up and lead.Brandon shares how 30–40% of the Wilson team has been promoted from within—and what separates those who grow fast from those who stall. They dig into Wilson’s 52-week Emerging Leaders program, the role of emotional intelligence and financial literacy, and how team members can take initiative to become future leaders.If you’re looking to grow your role or build leadership in your team, this one’s packed with real, actionable advice.🔹 In This Episode, We Cover: How to get promoted inside a home service business What Wilson looks for in future leaders The Emerging Leaders program: structure and impact Why a growth mindset and proactivity matter How communication and responsibility open doors Transparency around career progression at Wilson🌐 More resources: ownedandoperated.com👤 Hosted by: John Wilson👤 Guest: Brandon Niro 💼 Shoutout to Appletree Business Services HVAC and plumbing pros—ditch tax surprises and unresponsive accountants. Appletree handles your books, taxes, payroll, and acquisitions, and they know tools like ServiceTitan cold.🎁 Get a free tax & financial review or 10% off a QOE report. 👉 Book a call here — tell Patrick Jack sent you.💼 Shoutout to Quick Staffers LLC Need trained HVAC & plumbing CSRs at a fraction of the cost? Quick Staffers LLC specializes in placing top-tier global talent with the best SOPs and scripts. 🔥 Get $1,000 off your first placement hereSend Us Mail!More Ways To Connect with O&O John's YouTube Channel Weekly Newsletter Leave a Review John Wilson, CEO of Wilson CompaniesJack Carr, CEO of Rapid HVAC📌 Disclaimer:Some links may include UTM parameters for tracking. Episodes may feature paid sponsors, but all opinions are our own. Always do your own research before making business decisions.

 In this episode of Owned and Operated, we're digging into what it really takes to lead a growing home service business. From SOPs to scaling strategies, we’re spotlighting the habits and leadership traits that drive operational clarity and empower teams.We’re joined by Brandon Niro, who shares how his role evolved since joining the company in 2019—navigating growth from 30 to over 60 employees, integrating acquisitions, and shifting from tactical execution to strategic coaching and development.Whether you're a team lead or an operator scaling fast, this episode offers actionable insights into building systems, coaching talent, and creating autonomy inside a service business.🔹 In This Episode, We Cover: How SOPs streamline operations and unlock autonomy Coaching vs. doing: leadership in a growing team Transitioning from tactical roles to strategic leadership Navigating the growth curve—from 30 to 60+ employees Open-book management and building a transparent culture Why documenting processes fuels long-term scale🌐 More resources: https://www.ownedandoperated.com👤 Hosted by: John Wilson 👤 Guest: Brandon Niro💼 Special Thanks to First Internet Bank! Looking to buy or expand a business? First Internet Bank is a National Preferred SBA lender specializing in acquisitions for the skilled trades. Their SBA loan program offers up to 90% financing for business acquisitions, partner buyouts, and commercial real estate—plus optional lines of credit to fuel future growth. Unlike traditional lenders, they take a “how can we” approach, making deals happen for both first-time buyers and experienced operators.👉 Special Offer: Mention Owned and Operated for a reduced good faith deposit and a complimentary deal review + buyside prequalification.Connect with Alan Peterson from First Internet Bank here to get started!💡 Shoutout to Avoca AI! Avoca is helping home service companies level up with 24/7 AI call handling, performance insights, and targeted coaching. 🔗 Book a demoSend Us Mail!More Ways To Connect with O&O John's YouTube Channel Weekly Newsletter Leave a Review John Wilson, CEO of Wilson CompaniesJack Carr, CEO of Rapid HVAC📌 Disclaimer:Some links may include UTM parameters for tracking. Episodes may feature paid sponsors, but all opinions are our own. Always do your own research before making business decisions.

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—including pool services and a high-end art framing company.Whether you're just starting your acquisition journey or already mid-process, this episode is packed with practical insights for sourcing deals and building a compelling presence in the marketplace.🔹 In This Episode, We Cover: Strategies for off-market deal sourcing using freelancers How personal branding attracts brokers and deal flow The value of a credible buyer persona in competitive markets Updates on two live deals: pool services and art framing How Chris is approaching broker and seller interactions🌐 More resources 👤 Hosted by: Jack Carr 👤 Guest: Chris Barr 💼 Shoutout to Quick Staffers LLC Need trained HVAC & plumbing CSRs at a fraction of the cost? Quick Staffers LLC specializes in placing top-tier global talent with the best SOPs and scripts. 🔥 Get $1,000 off your first placement here💸Sponsored by CFO Made EasyBuilt a strong trades business? Let’s take it to $10M and beyond. CFO Made Easy offers part-time CFO services for home and trade service businesses—helping you boost cash flow, maximize profit per tech, and make clear growth decisions.📈 Free Offer: Book a 45-min Financial Insight Session to uncover growth blockers.Send Us Mail!More Ways To Connect with O&O John's YouTube Channel Weekly Newsletter Leave a Review John Wilson, CEO of Wilson CompaniesJack Carr, CEO of Rapid HVAC📌 Disclaimer:Some links may include UTM parameters for tracking. Episodes may feature paid sponsors, but all opinions are our own. Always do your own research before making business decisions.

In this episode of Owned and Operated, we’re diving into innovative lead generation strategies that are reshaping how home service companies attract local customers. From niche local newsletters to AI-powered tools, we cover real-world tactics that are working right now.We explore how hyperlocal publications in places like Annapolis, Maryland and suburban New York are driving leads for services like power washing and home inspections—and why owning your communication channels (email lists, Facebook groups) is a game-changer.Whether you're just starting or scaling up, this episode will give you actionable insights on using community engagement, AI tools like Avoca, and Facebook group sponsorships to fill your pipeline and take control of your local market.🔹 In This Episode, We Cover:Real examples of local newsletters driving leads for home servicesWhy owning your audience (email + groups) beats renting attentionHow AI tools like Avoca help manage leads and customer serviceFacebook groups as high-conversion lead generation platformsCommunity sponsorships as a brand-building strategyAn upcoming workshop for local lead domination🌐 More resources here👤 Hosted by: Jack Carr John Wilson 💼 Shoutout to Avoca AI! Looking to train your call center and improve technician performance? Avoca AI helps teams identify issues, improve call quality, and drive results from start to finish. 🔗 Schedule a demo here!💼 Shoutout to Quick Staffers LLC Need trained HVAC & plumbing CSRs at a fraction of the cost? Quick Staffers LLC specializes in placing top-tier global talent with the best SOPs and scripts. 🔥 Get $1,000 off your first placement here Send Us Mail!More Ways To Connect with O&O John's YouTube Channel Weekly Newsletter Leave a Review John Wilson, CEO of Wilson CompaniesJack Carr, CEO of Rapid HVAC📌 Disclaimer:Some links may include UTM parameters for tracking. Episodes may feature paid sponsors, but all opinions are our own. Always do your own research before making business decisions.

In this episode of Owned and Operated, HVAC business experts Jack Carr and John Wilson break down the sales strategies that drive revenue growth at every stage of a home service company’s journey. Whether you're running a $1M shop or scaling past $50M, understanding how to structure your HVAC sales team is critical—and it starts with knowing the difference between marketed leads and technician-generated leads.Jack and John explore why top HVAC companies like Four Seasons, Logan Services, and Peterman Brothers separate their sales teams based on lead source, and how that impacts close rates, efficiency, and scalability. From peer groups and sales training to seasonal lead flow and process refinement, this episode delivers real-world strategies for owners looking to increase HVAC revenue, optimize sales performance, and build scalable systems that actually work.🔹 In This Episode, We Cover:The difference between marketed leads vs. tech-generated leadsWhy large HVAC companies often split sales teamsSeasonal weather’s impact on lead flow and performancePeer groups as a catalyst for refining sales strategyChallenges in scaling marketing-led sales for smaller operatorsSales process breakdowns from Four Seasons, Logan, and PetermanThe role of efficiency and closing rates in mature orgsStrategies for training techs to sell in the field🌐 More resources: ownedandoperated.com👤 Hosted by: Jack Carr  John Wilson 📣 This episode is sponsored by Owned and Operated Pro The private, vetted community for serious home service business owners. Inside OAO Pro, you’ll get matched with a small peer group of operators facing the same challenges, access behind-the-scenes content from top businesses, and tap into exclusive events and vendor deals.It’s not just a community—it’s a growth engine. 👉 Learn more here💼 Special Thanks to Service Scalers!We’ve been partnering with Service Scalers to maximize our Local Service Ads (LSAs) and optimize our Google My Business profiles, and the results have been incredible. With hundreds of thousands in sales and 900+ calls in a single week, GMBs are now our top-performing organic lead channel. Want to learn how Service Scalers can do the same for you? 🔗Check Them Out Here Send Us Mail!More Ways To Connect with O&O John's YouTube Channel Weekly Newsletter Leave a Review John Wilson, CEO of Wilson CompaniesJack Carr, CEO of Rapid HVAC📌 Disclaimer:Some links may include UTM parameters for tracking. Episodes may feature paid sponsors, but all opinions are our own. Always do your own research before making business decisions.

 In this episode we’re back with part two of the Chris Barr series on Jackquisitions. Chris is three months into his journey to acquire a business in Florida, and he’s bringing real updates from the trenches. From opportunity cost and deal dynamics to cold outreach and broker networks, this episode is packed with hard-won insights from an active business searcher. We dive into the pros and cons of a pool service business he’s evaluating, the realities of navigating employee classification, and how acquisition imperfections are often just part of the game. Chris breaks down the lessons learned so far—from generating leads to refining search strategies—and why growth, not just debt repayment, should be the north star in any acquisition strategy.If you're in the search phase or thinking about acquiring a service business, this is a front-row seat to the messy, insightful, and exciting reality of buying a company.🔹 In This Episode, We Cover:Navigating the first 90 days of a business searchWhy opportunity cost is a real consideration in searchBehind-the-scenes of evaluating a pool service businessKey pros and cons of industry-specific acquisitionsHow Chris is using cold outreach and networking to source dealsThe tradeoffs between growth and early debt repaymentWhy no acquisition deal is ever perfect—and that’s okayRefreshing broker pipelines and learning from every interactionLessons in lead generation and seller conversations🌐 More resources 👤 Hosted by: Jack Carr 👤Episode Guest Chris Barr 💼 Shoutout to Appletree Business Services HVAC and plumbing pros—ditch tax surprises and unresponsive accountants. Appletree handles your books, taxes, payroll, and acquisitions, and they know tools like ServiceTitan cold.🎁 Get a free tax & financial review or 10% off a QOE report. 👉 Book a call at Appletreebusiness.com — tell Patrick Jack sent you.💼 Special Thanks to First Internet Bank! Looking to buy or expand a business? First Internet Bank is a National Preferred SBA lender specializing in acquisitions for the skilled trades. Their SBA loan program offers up to 90% financing for business acquisitions, partner buyouts, and commercial real estate—plus optional lines of credit to fuel future growth. Unlike traditional lenders, they take a “how can we” approach, making deals happen for both first-time buyers and experienced operators.👉 Special Offer: Mention Owned and Operated for a reduced good faith deposit and a complimentary deal review + buyside prequalification.Send Us Mail!More Ways To Connect with O&O John's YouTube Channel Weekly Newsletter Leave a Review John Wilson, CEO of Wilson CompaniesJack Carr, CEO of Rapid HVAC📌 Disclaimer:Some links may include UTM parameters for tracking. Episodes may feature paid sponsors, but all opinions are our own. Always do your own research before making business decisions.