Economic uncertainty can make even the most confident founders second-guess their timing.
Do I sell now?
Should I wait for the market to rebound?
Will buyers pull back entirely?
These questions are natural. I had them myself when I exited Pepperjam in 2009 — right after the financial collapse. And yet, the deal got done. Not just done — done well.
Because in any cycle — boom or bust — there’s one constant: Prepared businesses exit. Unprepared ones get stuck.
At Legacy Advisors, we’ve helped founders navigate exits through volatility, interest rate shocks, tech downturns, and unexpected black swan events. The deal flow may slow. Buyer behavior may shift. But the need for acquisition targets never disappears.
This article is your tactical guide for building an exit strategy that works even when the market feels uncertain — featuring hard-earned lessons from my own exits, insights from The Entrepreneur’s Exit Playbook, and strategy frameworks we use every week with our clients and podcast audience.
Why Economic Uncertainty Doesn’t Kill Exits
First — let’s dispel the myth that M&A grinds to a halt in shaky conditions.
It doesn’t. It shifts.
- Strategic buyers still buy, but with more discipline
- PE firms still deploy capital, but get tighter on structure
- Multiples may compress, but quality targets stay competitive
What changes is the buyer’s risk tolerance — and your need to position your business as a solution to that risk.
As I write in The Entrepreneur’s Exit Playbook (read here), when markets get uncertain, buyers stop underwriting the future — and start analyzing your present.
You must show them a business that performs today. Not one that might perform someday.
Real Experience: Selling Pepperjam in 2009
Let’s rewind. The financial crisis of 2008 had just rocked the global economy.
Cash was tight. Capital markets were frozen. “Wait it out” became the default founder mindset.
I didn’t wait.
I leaned in.
Pepperjam was a performance marketing platform with real margins, strong recurring revenue, and integrations with retailers that still needed results — even in a downturn.
We had a strategic partnership with GSI Commerce that let them see how we operated. That “try before you buy” experience lowered risk and accelerated trust.
And in early 2009 — we exited. To eBay, by way of GSI.
What did I learn? That a volatile market is not a death sentence. It’s a test of your positioning.
How Buyers Behave During Uncertainty
Here’s what we see consistently at Legacy Advisors when market volatility sets in:
- Valuations compress: Not because your business got worse — because buyers model lower forward multiples
- Diligence gets deeper: Expect tougher questions, longer cycles, and stress-tested assumptions
- Structure shifts: More earnouts, seller notes, and contingent terms
- Risk gets repriced: Customer concentration, churn, and CAC efficiency are under a microscope
Buyers become more selective. That’s not a red light — it’s an opportunity to stand out.
What Founders Must Do Differently
1. Operate Like a Buyer Is Already Watching
If your plan is to “clean things up when the time comes,” you’re already behind.
Start today:
- Accrual-based accounting
- Monthly reporting packages
- Documented SOPs
- Retention and margin dashboards
- Customer segmentation by risk and value
We call this exit readiness — and it’s not optional in a volatile cycle.
2. Emphasize Resilience, Not Just Growth
In hot markets, buyers love your upside. In cold ones, they want to see your core.
Key narratives that work:
- “We have low churn and 3+ year retention.”
- “Our EBITDA margin has expanded YoY.”
- “We’re profitable without further capital.”
- “We’re mission-critical to our customers’ stack.”
Highlight what’s repeatable, predictable, and efficient.
3. Align Your Forecasts With Reality
Buyers are no longer betting on hockey-stick charts.
Use historical performance to guide projections. Don’t overpromise — over-justify.
Add sensitivity models:
- Base case
- Downside case
- Recession case
When you can walk into a room and say, “Here’s how we win even in a flat economy,” you lead the conversation.
Structure Becomes the Variable
In an uncertain climate, deal structure becomes more important than headline price.
You may see:
- 50–60% cash at close
- 20–30% earnout over 12–24 months
- 10–20% seller note or equity rollover
Sound scary? It’s not — if you’ve done the prep.
Structured deals let buyers manage risk — and let you participate in future upside.
At Legacy Advisors, we help founders negotiate win-win outcomes that reward performance without giving up control.
Should You Wait to Exit?
This is the million-dollar question. My answer?
Don’t time the market. Time your momentum.
If your business is scaling, your books are clean, and strategic buyers are circling — go now.
If your margins are thin, retention is shaky, or the narrative isn’t tight — fix those first.
Uncertainty alone is never the reason to wait. Lack of readiness is.
Leverage Strategic Partnerships as Entry Points
Just like we did at Pepperjam, strategic partnerships can de-risk the M&A conversation.
- Integration projects
- Joint go-to-market campaigns
- Channel partnerships
- White-label agreements
These partnerships let the buyer test your systems, culture, and alignment — while you get inside access to how they think.
And when the time comes, the acquisition often feels like the natural next step.
What We Share on the Legacy Advisors Podcast
On Episode 10, we talked about how founders should prepare for due diligence during periods of macro volatility.
Key themes:
- Be able to explain how your customer base holds up in a recession
- Show vendor and cost rationalization discipline
- Highlight pricing power and gross margin protection
- Prepare for longer time-to-close — but also more thoughtful buyers
The best founders embrace this environment. It’s a sorting mechanism. And the serious buyers rise to the top.
Kris’s Playbook: Exit Best Practices in Uncertain Markets
Here’s what I recommend founders do now — not later:
✅ Run a mock diligence process
Get your CFO or advisor to act like the buyer. Fill the data room. Find the cracks.
✅ Model different exit scenarios
What if the deal takes 12 months? What if it includes an earnout? What if valuations fall 20%?
✅ Start tracking buyer interactions
Even casual inquiries tell you where market interest is — and what your category’s appetite looks like.
✅ Position for certainty
Cut the fluff. Make your numbers sing. Document everything.
✅ Align with advisors who’ve exited in all cycles
Legacy Advisors exists because we’ve done this in recessions, bull markets, and black swans. You shouldn’t be doing this alone.
Final Thoughts
Economic uncertainty is no longer an excuse — it’s a filter.
It filters out the unprepared. The hopeful. The reactive.
But if you’re building intentionally, operating transparently, and telling a story rooted in durability, discipline, and momentum…
Then buyers will come.
And when they do — you’ll be ready.
Just like I was in 2009.
Because markets change. But readiness? That’s on you.
📘 Want to go deeper?
- Read The Entrepreneur’s Exit Playbook to learn how to build, position, and sell with confidence — even during uncertainty.
- Listen to the Legacy Advisors Podcast for weekly insights from real-world buyers, founders, and M&A experts.
Frequently Asked Questions About Exit Planning During Economic Uncertainty
How do I know if it’s the right time to sell during economic uncertainty?
It’s rarely about perfect timing — it’s about business readiness. If your company is financially healthy, operationally sound, and you’re receiving inbound interest, that may be the right window regardless of macro conditions. Waiting for the economy to stabilize could cost you momentum or valuation leverage. At Legacy Advisors, we advise founders to look at internal signals — strong EBITDA margins, high customer retention, predictable growth — as a more reliable indicator than economic headlines.
What deal structures are most common when the market is volatile?
During uncertain periods, acquirers often prefer deals that share risk. This includes structured components like earnouts, seller notes, equity rollovers, and staged payments. These structures protect the buyer against future downside while offering the seller additional upside if the company performs post-close. Founders should prepare for these deal types and work with experienced advisors to negotiate terms that are fair and aligned with business fundamentals.
Will buyers still pay strong multiples during a recession or downturn?
Yes — for the right businesses. While headline multiples may compress industry-wide, companies that demonstrate durability, efficient operations, and healthy margins still command attractive valuations. In fact, many buyers seek recession-proof businesses precisely during downturns. The key is to highlight what makes your business essential and to present financials that show resilience, not just growth potential. Buyers reward clarity and confidence, especially when uncertainty clouds the rest of the market.
How should I change my positioning if I plan to sell during uncertain times?
Shift your narrative from future potential to present performance. Emphasize margin stability, customer loyalty, cash flow visibility, and cost control. Explain how you’re insulated from macro shocks or how your solution becomes more critical in a down market. Forecast conservatively and back it up with proof. Buyers are looking for signs of risk management, adaptability, and strategic foresight. Telling a story rooted in realism, not hype, gives them confidence to move forward.
What are the biggest mistakes founders make when trying to exit in volatile markets?
The most common mistakes include waiting too long to prepare, relying on outdated valuations, resisting structured deals without understanding them, and failing to present a buyer-ready narrative. Some founders go quiet during downturns, hoping conditions improve — only to miss great opportunities. Others approach buyers with messy financials and unvetted assumptions. The solution is early planning, honest self-assessment, and working with an M&A team who’s navigated turbulent markets before. Your readiness matters more than the market.