Know When to Kill a Deal

Welcome to the JackQuisitions newsletter,

As you work through the acquisition process, there’s always a chance that a red flag or roadblock will appear. When that happens, you have a decision to make: do you forge ahead or kill the deal on the spot?

Below, I share thoughts on when it makes sense to kill a deal. It’s never easy, but it’s often the right decision.

The Fastest Way to Make an Acquisition

Want first crack at HVAC, plumbing, and electrical businesses for sale?

Join the Business Modification Group buyer list.

Rather than fight hundreds of prospective buyers for the best deals, get notified the moment a trades business hits the market.

✅ Be the first to see new deals
✅ Get a complimentary deal review
✅ Access exclusive off-market opportunities

Join the list here before the next deal drops. It could be the difference between making a deal and finding yourself stuck at square one.

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 $5.85M revenue HVAC business in Florida nets $1.23M—29% service, 36% residential changeouts, and 35% commercial new construction with less than 3% refrigeration. Operates with flat-rate pricing, QuickBooks for accounting, and a CRM system in place. Holds ~1,000 maintenance agreements and has completed 245 changeouts in the last 12 months.

This $1.3M revenue HVAC business nets $140K—serving both residential and commercial customers with a focus on service, maintenance, and equipment installation. Operates with monthly rent of $1,350 and has shown sustained growth, profitability, and positive cash flow.

This $11.35M revenue HVAC business nets $1.13M—70% commercial and 30% residential, with 80% of revenue from new construction and renovation and 20% from service. Operates with flat-rate pricing, QuickBooks for accounting, and a CRM system in place. Maintains ~3,000 active customers, with the bulk of work focused on multifamily housing complexes and no refrigeration services.

This $1M revenue HVAC business in Riverside, California nets $218K—established in 2012 with over 1,600 loyal customers and 261+ five-star reviews. Operates with monthly rent of $2,555 and a strong maintenance agreement program driving recurring income. Includes trucks, tools, office equipment, digital assets, and professional branding with a well-established online presence.

A Dead Deal is Often the Best Deal

Most deals do not fall apart because the numbers never worked. Nope.

They fall apart because the risk shifts and the price no longer makes sense. That is what happened to Chris Barr.

On paper, it looked like the ideal business.

He loved the sector, got along with the owners, and the fit seemed right. But once the quality of earnings and bank statements came in, the story changed.

The financials revealed drops in SDE, operational discrepancies, and gray areas the seller could not explain. When Chris asked for a price adjustment, the sellers would not budge. That left him with a worse multiple than he signed up for.

I told him what I tell anyone in that spot: ignore the emotion and ask if the purchase price justifies the risk. His answer was no. And that is why he walked.

Why You Walk Away

Killing a deal hurts in the moment, but it saves you from bigger problems down the line.

• You do not lock yourself into a take-home that will not justify the effort.

• You do not gamble on “hidden potential” buried in sloppy books.

• You do not let the sunk costs of lawyers, accountants, and three months of work push you forward.

Instead, you buy yourself freedom. Freedom to reset, refine your process, and take another swing when the right opportunity comes along.

Chris told me it felt like paying tuition. The money, time, and emotion he sunk into the process bought him sharper instincts and stronger discipline. He can now spot risk faster, manage due diligence more efficiently, and lean on the experience when the next LOI comes across his desk.

Lessons for Operators

When you are in the middle of a deal, you need a filter that cuts through the noise:

• Does the purchase price line up with the real risk you are taking? Multiples are just market markers, not gospel.

• Are the books backed up by bank statements and a quality of earnings, or are you trusting the seller’s story?

• Will the take-home you model out be worth the grind once you are in the operator’s chair?

The Primary Takeaway

Too many buyers ride out bad deals because they feel trapped by sunk costs. Chris proved the opposite.

He let go of what looked like a dream business, and that decision will pay off for years. There will always be another deal. The skill is knowing when the juice is not worth the squeeze.

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.

Tell Me What You’re Thinking

I’ll make it simple for you: never be afraid to walk away from an acquisition. You must be 100 percent confident in your decision to sign on the dotted line. If you’re not, put on your walking shoes.

Got questions or require guidance? Get with me on X or LinkedIn.

Disclosure: Some of the content and links in this newsletter are sponsored or affiliate links, which means we may receive payment or earn a commission if you click through or purchase. However, all opinions expressed are entirely my own.

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