Resources | S74

5 Steps to Make Your Business Sale-Ready Before Retirement

Written by Darren | Aug 22, 2025 7:01:09 PM

If you’re planning to retire and sell your business, the five key steps to get it sale-ready:

  1. Organize and clean up financial records

  2. Strengthen management and operations

  3. Diversify revenue and customer base

  4. Document processes and systems

  5. Address legal, tax, and compliance issues

John’s Last Summer on the Job

John, a 68-year-old HVAC company owner in Dallas, had been telling his wife for years, “One more summer season, then I’m done.” Forty years of running trucks, hiring techs, balancing books at the kitchen table — it was time for golf trips and grandkids.

But when a broker introduced a serious buyer, John realized he wasn’t ready.

  • His financials were a mix of QuickBooks, handwritten invoices, and mental math.

  • Only he knew how to price certain bids.

  • 60% of revenue came from one apartment complex.

John’s story isn’t unusual. According to the Exit Planning Institute, over 75% of owners who sell their business regret the decision within a year, often because they didn’t prepare — financially, operationally, or emotionally.

At Sixty74, we’ve seen this from both sides of the table. That’s why we approach readiness like we approach an acquisition: methodically, without rushing, and always with the owner’s long-term goals in mind.

Here’s how to start — ideally 3–5 years before you plan to sell.

Step 1: Organize and Clean Up Your Financial Records

Buyers want clarity. Brokers want clarity. Lenders demand it. Without clean, organized financials, even the best business will look risky.

Why It Matters

  • Valuation Confidence: Clean books allow for accurate EBITDA calculation, directly affecting the sale price.

  • Deal Speed: Disorganized financials create delays that can derail a deal.

  • Trust: Buyers will assume operational chaos if they see financial chaos.

What to Do

  • Move all bookkeeping to GAAP-compliant software.

  • Reconcile accounts monthly.

  • Separate personal and business expenses (the SBA stresses this for all small businesses).
  • Keep 3–5 years of P&L, balance sheets, and cash flow statements ready.

  • Consider a pre-sale financial audit to find and fix red flags.

Sixty74 Perspective
When we review a potential acquisition, one of the first things we check is whether the numbers make sense at a glance. If we have to spend weeks untangling the story, we know employees and customers have probably been feeling that same confusion.

Step 2: Strengthen Management and Operations

If your business can’t function without you, it’s worth less. Simple as that.

Why It Matters

  • Risk Reduction: Buyers fear “key person risk” — the business failing when the owner leaves.

  • Scalability: Strong management signals growth potential.

  • Employee Retention: A stable team reassures both buyer and staff.

What to Do

  • Identify key managers and invest in their growth.

  • Begin delegating decision-making well before listing.

  • Create clear job descriptions and performance KPIs.

  • Introduce second-in-command leadership where gaps exist.

Sixty74 Perspective
We don’t just look at the management org chart; we talk to the people. If we see capable leaders who are eager for more responsibility, that’s a sign we can preserve culture and grow without disruption.

Step 3: Diversify Revenue and Customer Base

If 50% of your revenue comes from one customer, buyers see a cliff, not a moat.

Why It Matters

  • Valuation Impact: High concentration lowers multiples.

  • Resilience: Diversified income protects against market shifts.

  • Buyer Appeal: Broad client base = lower perceived risk.

What to Do

  • Target new industries or geographies.

  • Expand service offerings.

  • Create tiered pricing to appeal to different segments.

  • Develop recurring revenue streams.

Sixty74 Perspective
We know concentration risk doesn’t always mean fragility — sometimes it’s loyalty. But buyers still discount it. Fixing it before you sell puts you in a stronger negotiating position.

Step 4: Document Processes and Systems

Buyers pay more for businesses they can understand and operate quickly.

Why It Matters

  • Transferability: SOPs allow smooth handoff.

  • Training Efficiency: New hires ramp faster.

  • Consistency: Reduces variability in product/service quality.

What to Do

  • Create Standard Operating Procedures for all major functions.

  • Document vendor relationships, contracts, and renewal dates.

  • Map workflows visually (Lucidchart, Miro).

  • Store all documentation in a secure, shareable system.

Sixty74 Perspective
When we acquire a company with a clear operations manual, we can integrate our stewardship approach faster — and with far less disruption.

Step 5: Address Legal, Tax, and Compliance Issues

Unresolved legal issues can kill deals fast.

Why It Matters

  • Deal Certainty: Clean legal standing accelerates closing.

  • Negotiation Leverage: Fewer contingencies = stronger position.

  • Post-Sale Protection: Reduces exposure after you leave.

What to Do

  • Review all contracts for assignability.

  • Resolve disputes early.

  • Verify licenses and permits are up to date.

  • Consult a tax advisor on structuring the sale for optimal after-tax proceeds.

Sixty74 Perspective
We’ve walked away from great companies because of messy legal situations that would take years to unwind. Sellers who handle these proactively have a huge advantage.

The Last 12 Months Before Retirement – A High-Level Roadmap

  • Months 1–3: Finalize financial cleanup, delegate daily operations.

  • Months 4–6: Reduce customer concentration, finalize SOP documentation.

  • Months 7–9: Address legal/tax items, prepare broker package.

  • Months 10–12: Engage serious buyers, plan for the first 100 days with the acquirer.

The Bottom Line

Preparing your business for sale before retirement isn’t about selling tomorrow — it’s about controlling the story and the outcome. At Sixty74, we help owners step into their next chapter without sacrificing the legacy they’ve built.

If you’re within 3–5 years of retirement, now is the time to start. 

Let's talk about how we can steward your business into its next chapter.