☀️Summer in Full Swing, News on Snooze, and a Reality Check for Business Buyers

We just came off one of those golden summer weekends here in Wisconsin - the kind that reminds you why we endure the winters. Sunny skies, temps in the 90s, and all the grilled brats and lake time you could ask for.

Meanwhile, on the news front? Pretty quiet. In fact, the global cycle has been moving about as slowly as the SBA’s lately - no big updates, no new policy shifts, no curveballs from D.C.

But here’s the upside: slow news = focused buyers.

This is the perfect time to zoom in on a part of the acquisition process that often gets overlooked - how well your personal and professional background matches the business you’re buying.

Because here’s the truth:

A business can look perfect on paper. But if you’re not the right person to lead it, you’ll feel that disconnect fast.

Let’s unpack how to assess fit - and why it matters more than you think.

A Story That Happens More Than You Think: Sarah and the Plumbing Company

Meet Sarah.

She’s a highly accomplished tech exec fresh off a great run managing engineering teams at a Fortune 500. She’s smart, strategic, and ready to buy her first small business.

Sarah finds a plumbing company with steady cash flow, a strong team, and decades of customer trust. From a numbers standpoint, it’s a great deal.

But there’s a catch:

The company requires a licensed plumber to stay compliant - and Sarah isn’t licensed. She’s never worked in the trades and doesn’t know the technical side.

Fortunately, there’s a master plumber on staff willing to stay on - and possibly even take some equity to help smooth the transition and keep the bank comfortable.

So… is this still a smart move?

That depends on what Sarah does next.

What Sarah Brings to the Table (And What She Doesn’t)

She may not know plumbing, but Sarah does bring a lot:

• Leadership: She’s led teams, built culture, and developed high performers.
• Financial Management: She understands P&Ls, budgets, and profitability.
• Strategic Thinking: She knows how to streamline, scale, and innovate.

Those are powerful, transferable skills. But here’s the real question:

Can they overcome her lack of technical expertise and still make her a strong, credible owner?

Before You Write the LOI: Ask the Right Questions

Pre-LOI due diligence shouldn’t just be about the financials. Sarah—and any smart buyer—needs to get into the weeds of the day-to-day.

Key questions to ask:

• What does the current owner actually do on a daily basis?
• Which tasks require technical knowledge vs. business acumen?
• How often is the license-holder involved in key decisions?
• What happens if that person isn’t available?
• How much of the workload is hands-on vs. administrative?

These answers will help Sarah figure out whether she’s stepping into a leadership role - or a technical role she’s unprepared for.

The Business Plan: Not Just for the Bank - It’s for You

At some point, Sarah will write her SBA business plan. And in it, she’ll need to clearly lay out:

• Who’s running daily operations
• What her background brings to the business
• What skills are transferable—and how they’ll be applied
• How she’s filling the gaps she doesn’t cover personally

This isn’t just a hoop to jump through - it’s a real test of whether her story holds up under pressure.

If she can’t articulate her plan with clarity and confidence, that’s a red flag she (and the lender) should pay attention to.

SWOT Yourself

Every buyer should do a personal SWOT analysis before closing a deal. Sarah’s might look like:

• Strengths: Strategic thinking, financial savvy, people management
• Weaknesses: No plumbing experience, not license-qualified
• Opportunities: Retain key staff, modernize ops, grow service lines
• Threats: Losing key staff, lender concerns, operational blind spots

If her plan addresses those weaknesses head-on, she’s in good shape. If not? It’s time to slow down

One Last Myth to Bust

“Business is business” is not a strategy.

Every industry has its quirks, regulations, and pressure points. What works in tech doesn’t always translate to blue-collar service.

Buying a business you don’t fully understand isn’t brave—it’s reckless. That doesn’t mean you can’t do it. It just means you need a clear-eyed plan, the right partners, and a willingness to learn what you don’t know.

Takeaway This Week

Use this summer slowdown to reflect honestly:

• Am I the right person to lead this business?
• What do I really bring to the table?
• Where am I weak—and how do I fill that gap?
• Does my plan pass the lender test, the seller test, and the gut test?

There’s no shame in walking away from a deal that doesn’t fit your experience. In fact, that’s one of the smartest moves a buyer can make.

Because the goal isn’t to know everything—it’s to know yourself, build around your strengths, and own your weaknesses with clarity and confidence.

Want to Talk Through Your Target Acquisition?

If you’re working through a deal and want help thinking through experience fit, deal prep, or SBA strategy, my team and I would love to connect.

Ready to get started?

​Schedule a Buyer Strategy Call​

or reach out anytime at matthias@pioneercap.com

Thanks for reading. If there's a specific topic you're interested in, feel free to reach out - I'd love to hear your suggestions!

Disclaimer: The information in this newsletter is for informational purposes only and should not be considered legal or financial advice. Business buyers are encouraged to consult with their legal counsel and accountant to ensure the proper structuring of their transactions and to fully understand the tax implications of seller financing.

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