Markets don’t send polite warnings. One quarter looks stable, then sentiment flips, lending tightens, and buyers start asking harder questions. I’ve watched founders freeze during this phase, not because their businesses were failing, but because uncertainty made every decision feel heavier. That hesitation can quietly cost millions.
Exit planning during volatile cycles is less about timing the perfect peak and more about building options. The last time I worked with a founder preparing for sale during a messy economic patch, we didn’t chase a headline valuation. We focused on buyer confidence. Cleaner reporting. Predictable revenue. Documented processes. Boring stuff. The stuff buyers love.
Here’s the truth most people hate hearing. You rarely control the market, but you absolutely control how attractive your business looks when someone opens the hood.
Valuation Is Emotional, Not Just Financial
Numbers matter. Obviously. But buyers are human first, analysts second. If they sense chaos, they discount risk hard. If they see structure, they lean forward.
I once saw a strong service business lose 18 percent of potential value because the owner couldn’t explain customer churn patterns clearly. Nothing catastrophic. Just messy data. Fixing that would have taken two weeks.
Uncertain markets magnify small weaknesses. Cash flow timing. Customer concentration. Leadership dependency. Buyers assume worst-case scenarios if you don’t prove otherwise. That’s why preparing early beats reacting late.
Some founders try to hedge personal risk during exit prep by diversifying assets. One conversation I remember drifted into commodities, and the founder mentioned they planned to sell gold or silver in Melbourne to free liquidity before negotiations. Not typical dinner talk. But smart. Liquidity creates negotiating confidence.
Timing the Exit Versus Timing Your Readiness
Everyone obsesses over timing the market. I get it. Headlines drive anxiety. But readiness beats timing nine times out of ten.
Buyers still buy during downturns. Private equity still deploys capital. Strategic acquirers still hunt for capability gaps. What changes is selectiveness. They become picky. Brutal, sometimes.
I lean toward a simple stance. If your business is buyer-ready, you can move when opportunity appears. If you’re not ready, even a strong market won’t save a messy operation.
Ever noticed how deals move fastest when founders aren’t desperate? Buyers smell urgency instantly. Preparation removes that scent. It lets you walk away if terms feel wrong. And walking away is power. Real power.
Building a Business That Can Survive Without You
This one stings. Founders often build companies that depend on their personality, relationships, or decision speed. That works until exit talks start.
The first question serious buyers ask is simple. What happens if you leave tomorrow?
I once saw a founder laugh at that question. Two months later, the buyer reduced their offer after realizing the sales team relied on the founder’s personal network. That gap cost seven figures. Brutal lesson.
Removing yourself from daily operations is not about ego. It’s about transferability. Document sales processes. Train leaders to make decisions. Build reporting dashboards anyone can read without translation.
If your business needs you to survive, buyers treat it like a risky startup, not a mature asset.
Financial Strategy Still Matters, But Clarity Matters More
Founders sometimes drown in advice during uncertain markets. Accountants. brokers. analysts. Everyone has an opinion.
Strong operators cut through noise by focusing on clarity. Clean balance sheets. Predictable forecasting. Realistic growth assumptions. Not optimistic fantasy math.
I remember sitting in a strategy session where a founder debated whether to hire external advisors or keep planning internal. They eventually consulted some of the best financial advisors in Sydney to pressure test their exit structure. What surprised them was how much value came from simple tax sequencing and timing, not complex restructuring.
Clarity reduces surprises. Surprises kill deals. Every time.
The Psychology of Letting Go
Nobody talks about this enough. Exiting a business feels weird. Even when you want it.
I once thought I’d feel pure relief selling a company I helped scale. Instead, I felt restless for weeks. Founders often tie identity to the business. When exit planning starts, identity questions creep in. Who am I without this thing?
Planning your next chapter early sounds fluffy. It’s not. Buyers can sense hesitation. If you look emotionally conflicted, negotiations slow down. Momentum disappears.
Future planning also changes how you negotiate. If you know your next move, you stop chasing every extra dollar. You focus on deal structure, lifestyle outcomes, and risk protection.
Making Decisions Without Perfect Information
Here’s the uncomfortable part. You will never have perfect clarity in uncertain markets. Ever.
You’ll have signals. Partial data. Gut instinct. That’s normal. The founders who exit well don’t wait for certainty. They build resilience. They prepare financials monthly. They maintain buyer relationships long before selling. They track leading indicators, not just lagging revenue reports.
Momentum matters. If you wait for everything to feel safe, you’ll miss windows that only stay open for months, sometimes weeks.
Uncertain markets reward prepared operators. Not lucky ones. Not reactive ones. Prepared ones.
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Ryan Terrey
As Director of Marketing at The Entourage, Ryan Terrey is primarily focused on driving growth for companies through lead generation strategies. With a strong background in SEO/SEM, PPC and CRO from working in Sympli and InfoTrack, Ryan not only helps The Entourage brand grow and reach our target audience through campaigns that are creative, insightful and analytically driven, but also that of our 6, 7 and 8 figure members' audiences too.