What You Don’t Learn Until You’re in the Deal

Welcome to the JackQuisitions newsletter,

Earlier this month, I published the first standalone edition of JackQuisitions. Today, I’m back with edition #2 and another big announcement:

My first exclusive JackQuisitions podcast episode is now live. 🎉 (watch it and subscribe)

Financing Your First (or Next) Acquisition?

Buying a business can be scary, exciting, and challenging all at the same time. And for that reason, it’s important to surround yourself with the right team.

First Internet Bank’s Alan Peterson specializes in SBA 7(a) loans for business acquisitions, partner buyouts, and commercial real estate.

Whether you're buying your first company or scaling through acquisition, Alan's “how can we” mindset and hands-on approach make him the go-to lender in the skilled trades space.

• Finance up to 90% of your deal

• Get a complimentary deal review and buyside prequal

• Reduced good faith deposit when you mention the show

Alan works fast, knows what small business buyers actually need, and this is all he does.

Ready For Your Next Acquisition?

Finding your next acquisition target can be just as stressful as the process itself. Let me help. Here are some listings for your review:

This $3.24M revenue HVAC and plumbing business nets $612K—70% HVAC, 30% plumbing, 90% residential, 20% new construction, no refrigeration, 400 maintenance agreements, 3,700 active customers, flat-rate pricing, with QuickBooks, a CRM, and CPA-managed payroll in place.

This $1.33M revenue HVAC business nets $274K—55% commercial, 45% residential, no new construction or refrigeration, 263 total maintenance agreements, flat-rate pricing, with QuickBooks and a CRM in place.

This Centre County, PA HVAC business nets $236K—founded in 2021 with strong growth, five-star reputation, and a focus on installs, repairs, and maintenance of furnaces, AC, ventilation, and heat pumps. All equipment is included, and the business is positioned for continued expansion with new ownership.

This $837K revenue HVAC business nets $218K—established in 2020 with multiple revenue streams from installs, maintenance, repairs, and add-ons. Serves both residential and commercial clients, uses premium HVAC and air quality brands, runs on advanced CRM software, and leverages a national call center for support.

Creative Deal Structuring Is More Than Possible

Finding your next acquisition target is only half the battle. The real question is what happens after LOI is where the real lessons start?

Chris Barr thought he was buying a pressure washing business…

What he got was a crash course in recasting financials, managing seller expectations, and uncovering operational flaws he would eventually need to fix himself. The deal is still alive, but not without twists.

Due diligence took longer than expected. The sellers had messy records split across multiple bookkeepers and software platforms. The business ran QuickBooks on desktop, had outdated processes, and provided incomplete documentation. Chris could have walked. Instead, he extended the timeline and leaned into the relationship.

He approached the deal with a three-part due diligence plan: financial, legal, and operational.

Legal was the easiest. Financial turned complex when accrual-based reports painted a better picture than reality. Once they pivoted to a cash-basis view using bank statements, earnings dropped. That triggered a pricing conversation.

Instead of using a traditional Quality of Earnings report, Chris worked with his CPA to build a leaner, more hands-on version—what he called a QofE Light. It gave him the clarity he needed without spending $30,000 on a formal report.

The biggest challenge was operational.

• Scheduling was done on whiteboards

• Job margins were not tracked

• Systems were siloed. Most of it lived in people’s heads.

Still, Chris saw it as an opportunity to build something better.

He used ChatGPT to help identify ops diligence questions and mapped out the gaps himself. He also started recruiting a back-office ops manager before the deal even closed, giving him a stronger foundation for Day 1.

Here are a few of the improvements he plans to implement:

• Move from whiteboards to digital job scheduling with real-time visibility

• Consolidate CRM, accounting, and service tracking into a unified system

• Add margin tracking on every job to identify what actually makes money

• Delegate systems integration to a full-time ops hire from Day 1

The sellers are rolling this into a franchise model and want Chris to be the flagship operator. In return, they’re open to feedback and eager to improve. It’s not your typical owner-handoff.

Takeaway: Chris didn’t get a clean deal. He got a messy one with potential. But instead of forcing the business to fit his expectations, he changed the structure, rethought the risk, and designed the terms to match what was actually there.

Here’s the whole story ⬇️ 

Tell Me What You’re Thinking

Give me your thoughts on today’s newsletter. It’ll allow me to adjust my approach moving forward.

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