Timing isn’t everything in M&A — but it’s damn close.
One of the most common questions I get from founders is:
“When is the right time to sell?”
It’s not an easy answer. But after selling my company Pepperjam to GSI Commerce (which was later acquired by eBay), building and selling multiple businesses, and advising dozens of others through Legacy Advisors, I’ve seen that every great exit shares one thing in common:
It happened at the right time — for both the seller and the buyer.
In this article, I’ll walk you through how to identify the optimal window to sell your company — not based on hype, pressure, or fear — but based on strategy, preparation, and market dynamics.
Let’s dig in.
The Biggest Mistake Founders Make: Waiting Too Long
Most founders think they’ll “just know” when it’s time to sell. The truth?
They usually wait until:
- Growth starts to slow
- Margins tighten
- Team morale dips
- Their energy fades
- Or worse — market demand softens
And by then? The window they didn’t know they had — is already closing.
Timing your exit after your peak is like trying to sell a house after the foundation cracks. The buyers might still come — but the price will reflect the repairs.
How I Got It Right with Pepperjam
When I sold Pepperjam, we were coming off a record year.
- Revenue was up
- Margins were strong
- Strategic partnerships were forming
- And most importantly: I could see ahead
We weren’t desperate. We weren’t coasting. We were growing — but we were also bumping up against a need for scale and infrastructure that I knew we’d need help with.
Enter GSI Commerce. What began as a strategic partnership — integrating with some of their major sporting goods retail clients — evolved into acquisition talks.
The partnership gave them a front-row seat to how we operated. It gave us a window into their playbook.
And it gave both sides confidence to move.
That’s how deals happen when you time it right.
Three Categories of Timing
To find your optimal window, you need to evaluate three types of readiness:
- Personal Readiness
- Business Readiness
- Market Readiness
Let’s break them down.
1. Personal Readiness: Are You Ready?
This is the part founders often ignore — until it’s too late.
Ask yourself:
- Am I still energized by the mission?
- Am I the right person to take this to the next level?
- Do I feel more exhausted than excited?
- Is my identity too tied to this company?
- What’s next for me — after the exit?
One of the best filters is this:
If you could walk away today with life-changing wealth and no regrets — would you?
If the answer is yes, don’t wait for a downturn to prove you right.
2. Business Readiness: Are the Numbers There?
Buyers aren’t just buying your past. They’re buying your predictable future.
Key indicators your business is ready:
- Strong and expanding EBITDA margins
- Predictable, recurring revenue streams
- Clean financials (ideally reviewed or audited)
- Low customer concentration
- Documented processes and scalable operations
- Founder independence — the business doesn’t rely solely on you
If you’re not there yet, that’s okay — but start the exit prep now. It usually takes 12–24 months to fix what’s broken and highlight what’s great.
3. Market Readiness: Are Buyers Looking for You?
This is the part most founders don’t control — but absolutely must understand.
You might be personally and operationally ready… but if:
- Interest rates are climbing
- Valuations are compressing
- Your sector is out of favor
- Buyers are distracted or pulling back…
…you could get stuck in a frozen market.
Monitor:
- Deal volume in your space
- Strategic buyer behavior
- Private equity platform rollups
- Sector-specific M&A reports
- Conversations with bankers, advisors, and investors
At Legacy Advisors, we help clients read these signals early — and align them with internal momentum.
What Happens When You Nail the Timing
Founders who exit in their optimal window tend to experience:
- Fewer buyer objections
- Cleaner diligence processes
- Higher percentage of cash at close
- Shorter time to LOI and definitive agreement
- Less structure (earnouts, escrows)
- Greater personal clarity on what comes next
They’re not just “taking an offer” — they’re running a process.
They’re choosing the exit. The exit isn’t choosing them.
Signs You’re Approaching the Window
Here are a few green lights we watch for with clients:
✅ You’ve had two consecutive years of EBITDA growth above 20%
✅ You’ve launched a new product or feature that’s being adopted fast
✅ Multiple buyers have expressed inbound interest
✅ Your forecast accuracy over the last 12 months is within 10%
✅ Strategic partnerships are turning into commercial traction
✅ You’re building team depth beyond the founding crew
✅ You have clear data on CAC, LTV, retention, and margin expansion
✅ You’ve built the kind of business you would want to buy
Any three of those — and you’re probably closer than you think.
What If You’re Not Ready Yet?
That’s okay — but it’s time to get strategic.
Here’s what I recommend:
- Conduct a mock QofE (Quality of Earnings)
- Build a board of advisors (or M&A-prep team)
- Track buyer activity and benchmark data quarterly
- Clean up your financials and reporting systems
- Build a 12- to 18-month forecast tied to strategy
- Identify and reduce single points of failure (tech, people, customers)
- Read The Entrepreneur’s Exit Playbook for the full tactical roadmap
And don’t forget — you can always run a stealth pre-market process. Sometimes the act of preparing unlocks opportunities you didn’t know existed.
Legacy Advisors Podcast Insight
In Episode 8 of the Legacy Advisors Podcast (listen here), Ed and I talked about founders who got burned waiting for “just one more year.”
The reality?
“There’s no ‘perfect’ time to sell — only windows where the upside outweighs the risk.”
That’s why we advocate exit readiness — not just exit dreaming.
What I Teach in The Entrepreneur’s Exit Playbook
In the book (available here), I lay out a framework for exit readiness that includes both internal and external indicators.
We teach founders to think in 3 horizons:
- 0–12 months: Get clean, predictable, and profitable
- 12–24 months: Get scalable, team-driven, and data-rich
- 24–36 months: Get market-aware and position for process
The best exits happen not because the founder wanted to sell — but because the business was ready to be bought.
Final Checklist: Are You in the Window?
- Do you have 2+ years of clean financials with growing margins?
- Are your growth drivers repeatable and de-risked?
- Could your team operate without you?
- Are buyers active in your sector right now?
- Do you have strategic differentiation — not just scale?
- Could you confidently answer 30+ diligence questions today?
- Are you more excited about what comes next than what you’re doing today?
If yes — you’re in the window.
And if you’re not?
Start preparing.
Build discipline.
Create optionality.
Because exits don’t just happen.
They’re engineered.
And when you engineer yours with intention, the window opens exactly when you want it to.
Frequently Asked Questions About Identifying the Optimal Window for Selling Your Business
How do I know if I’m personally ready to sell my business?
It starts with clarity around your goals and emotional readiness. Ask yourself: Are you still energized by the work? Are you building for legacy or lifestyle? Do you feel confident in what you’d do after a sale? In The Entrepreneur’s Exit Playbook, Kris Jones emphasizes that personal readiness is just as important as business metrics — if not more. Founders who exit with purpose, not panic, walk away with fewer regrets. A strong signal that you’re personally ready is when you feel excitement, not fear, about what comes next and have the financial literacy to assess life after liquidity.
What are the key business signals that I’m in the “optimal window” to exit?
There are several leading indicators that your business is in prime exit shape:
- Consistently growing EBITDA margins (ideally above 15–20%)
- Two to three years of clean financials
- Recurring or contracted revenue
- Strategic partnerships converting into revenue
- Clear forecasting discipline and minimal “surprises”
- A leadership team that can operate independently of the founder
These signals show buyers that your business isn’t just growing — it’s stable, scalable, and transferable. As Kris often tells founders, “Buyers want proof they’re buying a machine — not just your hustle.”
What role does market timing play in the decision to sell?
A major one. Even if your business is in great shape, timing your sale when buyer demand is high and deal volume is active gives you better leverage. Conversely, trying to exit in a buyer’s market — when capital is tight, interest rates are high, or sector valuations are compressed — often leads to lower offers and more structure (like earnouts and escrows). Founders should keep an eye on deal comps, buyer behavior, and macro signals. Legacy Advisors helps founders align internal readiness with external opportunity — because the best outcomes happen when both are in sync.
What happens if I wait too long to sell?
Waiting too long often results in declining growth, shrinking margins, leadership fatigue, or lost buyer interest. Founders sometimes “fall in love” with their business and miss the opportunity to exit at peak value. Then when they’re finally ready to sell, the narrative becomes harder to defend: the numbers are down, momentum has slowed, and buyers sense they have the upper hand. Kris Jones has seen this pattern too often — founders trying to time the “perfect” top, only to realize it passed six quarters ago. You don’t need to be perfect. You just need to be prepared.
Can I test the market before committing to a full sale process?
Yes — and in many cases, you should. Testing the waters can involve:
- Having informal conversations with strategic buyers
- Sharing teaser decks with trusted PE firms or bankers
- Getting a valuation range from a qualified advisor
- Running a “pre-process” with NDAs and selective outreach
- Exploring strategic partnerships (like Kris did with GSI Commerce before Pepperjam’s sale)
These steps don’t commit you to a sale — but they give you signals about timing, valuation, and interest. Sometimes, just preparing for exit opens doors that accelerate it. That’s why The Entrepreneur’s Exit Playbook focuses on optionality — not pressure.