How to Sell Your Business at the Right Time: Insights from Lewis Schiff

Timing is everything when it comes to selling your business. On this episode of the $4M Strategies™ podcast, Carl J. Cox, CEO of 40 Strategy and 40 Accounting, welcomes Lewis Schiff, Chairman of The Birthing of Giants, to discuss the art and science of successful business exits. Selling your business can be one of the most critical and rewarding decisions you’ll make as an entrepreneur, and getting it right means understanding the interplay of personal, company, and market readiness.

The Three Pillars of a Successful Exit
  1. Your Readiness
    Lewis explains that a strong exit starts with you. Are you prepared to let go of your business? Surprisingly, the best time to sell is often when you’re most in love with what you’ve built—when the business is thriving, and you’re still fully engaged. Buyers can sense when you’re emotionally checked out, and that can lower your leverage.

Equally important is having a clear vision for life after the sale. Whether it’s starting a new venture, traveling the world, or pursuing a personal passion, knowing your next step gives you confidence and purpose during the transition.

  • Your Company’s Health
    Is your business in the best shape of its life? Lewis emphasizes the importance of ensuring your company is operationally sound, with robust processes, solid financials, and a high-performing team. A growing business with clear systems and strong morale is far more attractive to potential buyers.

Additionally, consider how your industry is performing. Is your sector thriving? Are customer needs being met? A strong business in a promising industry is a winning combination.

  • Market Conditions
    Macro-economic factors play a significant role in determining the strength of the M&A market. Low interest rates, a strong economy, and active private equity markets create ideal conditions for business sales. However, timing is key—waiting too long for “the next big opportunity” can lead to missing your peak.

Lewis describes how small businesses are often the first link in a chain of transactions. Buyers in these markets rely on favorable economic conditions to maintain the flow of deals, from small private equity firms to larger strategic buyers.

Why Business Owners Miss the Peak

One common challenge Lewis highlights is the tendency of business owners to wait too long. Many entrepreneurs believe their company will grow just a little more, increasing its value. However, the highest multiples often occur just before growth begins to plateau. Learning to recognize this inflection point can make the difference between a good exit and a great one.

Another reason owners hesitate is a lack of planning for life after the sale. Without a clear vision of what’s next, it’s easy to cling to the familiar. Lewis suggests taking the time to imagine your next chapter, so you can confidently move forward.

Key Questions to Ask Yourself
  • Am I emotionally ready to sell my business?
  • Is my company in its best possible condition?
  • Are market conditions favorable for a sale?
  • Do I have a plan for what comes after the sale?
Actionable Steps for Entrepreneurs
  • Assess Your Readiness: Take an honest look at your goals and motivations.
  • Prepare Your Business: Strengthen operations, stabilize leadership, and optimize processes.
  • Monitor Market Trends: Work with advisors to identify favorable conditions in your industry and the broader economy.
What You’ll Learn in This Episode

In this episode, Lewis Schiff shares practical advice and real-world examples of successful exits. You’ll learn why selling during a strong market with favorable conditions often leads to better outcomes and how to avoid common mistakes that can derail the process.

If you’re an entrepreneur considering your exit strategy, this conversation provides invaluable insights to help you sell your business at the right time.

Listen Now

Ready to maximize the value of your business? Tune in to the full episode of the $4M Strategies™ podcast to gain actionable strategies and expert advice from Lewis Schiff. Don’t miss out—your best exit could be closer than you think.

Ready to Sell? Take our Free $4M Growth Assessment!

📖 Get Your Copy of ‘Business Brilliant: Surprising Lessons from the Greatest Self-Made Business Icons’ 

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