You are in the thick of it: strong revenue growth, new market opportunities appearing every quarter, and perhaps the best team you have ever assembled. Yet, with all this momentum, you find yourself facing a question that can spark anxiety for even the most experienced founders: Should you consider selling your business now?
If you are wrestling with this, you are not alone. Many founders, especially in technology and services, receive increasing inbound interest from buyers and investors as their companies scale. Paradoxically, it is often exactly when things are going well that serious offers begin to appear. That’s when “The Entrepreneur’s Dilemma” comes into focus—how do you weigh the urge to capture the rewards of your effort versus the belief that the biggest gains are still ahead?
Why Buyers Love a Growth Story
Buyers—whether strategic acquirers or private equity—value certainty and upside, and there is no better evidence of both than a business in growth mode. High growth usually means strong demand, competitive differentiation, and the potential for scalability, all of which command premium valuations.
Growth also reduces perceived risk for buyers. They see momentum, a proven track record, and strong teams that can help continue the trajectory post-transaction. This is why you might suddenly find yourself on the radar when your numbers are trending up—and why the offers you receive as you accelerate often reflect far higher multiples than those available in a flat or declining market.
The Dilemma: Sell Too Early, Miss the Upside; Wait Too Long, Risk Missing the Window
Founders often hesitate to sell during a growth phase for understandable reasons:
- “If things keep going like this for just another year or two, the business will be worth double!”
- “There is still so much we want to achieve with the team and the product.”
- “What if a sale now looks like I am giving up too soon?”
At the same time, the greatest risk is waiting too long and missing the market window. Growth inevitably slows, markets change, competitors catch up, and economic shocks can erode even the best-laid plans. Trying to “time the top” is notoriously difficult—many founders look back with regret, wishing they had capitalized on momentum when it was strongest.
How to Think About Selling During Growth
1. Understand That Buyers Pay for What They Can See—Not Just the Future
Buyers pay premiums for visible, realized growth rather than projections or hopes. If you have already demonstrated several quarters (or years) of strong improvements, those are far more valuable than an aggressive five-year plan on a spreadsheet.
2. Recognize That Momentum Creates Buyer Competition
One of the most powerful negotiation advantages is having multiple buyers competing, especially when they see upside in future growth. The best offers—both in terms of valuation and deal structure—tend to come when momentum is strong and validated by your recent results.
3. A Sale Does Not Always Mean “The End”
Many deals (especially with private equity) provide opportunities for founders and teams to continue growing the business with extra resources, sometimes via “rollover equity” or incentives tied to future milestones. Strategic acquirers may also need you to guide integration or new business lines post-acquisition. This means you can, in fact, “sell” and still participate in future success.
4. Be Honest About Risk and Your Appetite
Growth can mask systemic business risks or simply create founder fatigue. Consider your personal goals, your financial security, and your desire to take on new challenges. Sometimes, derisking now—while the business is thriving—is both rational and wise.
Practical Advice for Founders Facing the Dilemma
- Benchmark Your Business: Do honest scenario planning. What if growth slows? What if a competitor enters? Ask yourself what events could trigger a decline in value.
- Stay Curious, Not Committed, to Inbound Interest: Don’t rush to sign exclusivity or share detailed numbers in response to inbound interest. Use the opportunity to test the market without obligation.
- Run a Structured, Competitive Process: If you decide to explore a sale, create genuine competition—don’t rely on a single buyer’s interest. An investment bank or M&A advisor can help you maximize optionality and keep the process confidential so you don’t signal “for sale” to the market prematurely.
- Don’t Let Emotion Dictate the Decision: It’s easy to let pride (or FOMO) cloud your judgment. Trusted advisors—legal, accounting, financial—can offer perspective and data-driven guidance.
- Negotiate for Partnership, Not Just a Pay Day: Well-structured transactions can offer continued upside, team stability, and even future leadership roles within the acquiring business.
The decision to sell during a growth phase is never simple and is rarely black and white. The real risk is not in selling “too early” but in failing to realize the value when your business is at its most attractive. Your job as a founder is to recognize when your momentum—and the resulting buyer enthusiasm—is creating a moment of maximum opportunity.
.webp)
