This week on “The Exit Strategy” we talk about how when you create a business, you have to know when the right time to exit is. This is a talent not too many entrepreneurs have mastered. It’s hard to “go out” on top!

Peter Shankman’s first major exit, The Geek Factory, stemmed from a realization that both he and the market had become complacent. He knew it was time to move on when the work started feeling “too easy.” This sense of ease, while comfortable, was actually a warning sign that innovation had stalled.

If you find yourself coasting through work without challenge or excitement, it may signal stagnation, either in your own engagement or in the market itself. Complacency often precedes decline, particularly in fast-changing industries. Shankman also paid close attention to market trends, recognizing the early signs of the dot-com bubble’s burst. Staying attuned to these shifts and being honest about your business’s growth potential is essential.

When Vocus, HARO’s largest advertiser, made an offer to buy his company, Shankman didn’t wait for a “perfect” deal that might never come. He advises founders not to reject a great offer while holding out for an imaginary better one. Regularly assessing both your business’s trajectory and your own passion ensures you’ll recognize the right moment to make your move. When either begins to wane, it’s time to consider an exit.

Navigating the Sale: Due Diligence, Earn-Outs, and Letting Go

Selling a business is as much an emotional process as a financial one. Shankman’s experience highlights how critical it is to balance preparation, patience, and perspective. During due diligence, founders often feel personally attacked by the level of scrutiny. But as Shankman points out, the process isn’t about you, it’s about the business. Trust your lawyers and advisors to safeguard your interests rather than micromanaging every detail.

When it comes to earn-outs, clarity is key. Shankman’s agreements were based on measurable metrics such as revenue, audience growth, and service continuation, making progress easy to track. Once the sale is completed, remember that control shifts to the buyer. Accepting this new reality, and your new role, if you have one,is vital.

Letting go can be one of the hardest parts. Feelings of loss are natural, but once the deal closes, the business is no longer yours. Prepare emotionally for this transition just as carefully as you prepare financially. Have a plan for what comes next,  whether that’s a new venture, a sabbatical, or a personal project, to help you move forward with purpose.

Balancing Founder Involvement and Business Independence

Buyers are drawn to businesses that can thrive without their founders, yet founder involvement often remains crucial for maintaining quality and vision. Shankman advocates for building systems and teams that can operate independently, while still allowing the founder to “nurture and protect” the brand, especially when it carries their name.

He suggests finding the balance between oversight and autonomy. Even a few hours a day of involvement can preserve standards and culture. However, knowing when to step back is equally important, if you’re unable to emotionally detach, it may not be the right time to sell.

Before your exit, document systems thoroughly, delegate effectively, and gradually reduce your daily role. This transition period not only reassures potential buyers but also helps you adjust to a life beyond day-to-day operations.

The Power of Personal Branding Beyond Your Business

Many entrepreneurs struggle to let go because their identity is too tightly bound to their business. Shankman avoided this by cultivating a personal brand that extended far beyond any single company. By sharing his interests, such as skydiving, travel, and public speaking, he showed that a founder’s influence doesn’t have to end with a sale.

A strong personal brand can open doors to new ventures and make transitions much smoother. Stay visible after an exit by writing, speaking, or consulting to maintain momentum and relevance. The key is to start early, long before you plan to sell, so you’re already known for your broader expertise and passions, not just your company.

Neurodiversity as an Entrepreneurial Advantage

Shankman’s is very open about his ADHD transformed since what was once seen as a challenge into one of his greatest strengths. His experience underscores that neurodiversity can be a competitive advantage in entrepreneurship. Many groundbreaking innovators, from Steve Jobs to Elon Musk have similar “different wiring,” which drives creativity and out-of-the-box thinking.

Leaders should recognize neurodiversity as an asset and build inclusive workplaces that value diverse cognitive styles. Companies like Morgan Stanley, Adobe, and Google have seen clear benefits from hiring neurodiverse talent, as these perspectives foster innovation and stronger problem-solving.

Combatting stigma early is crucial, Shankman’s own story of feeling “broken” as a child until reassured otherwise highlights how powerful positive messaging can be. For teams, education and flexibility are key. Offer training on neurodiversity, design adaptable roles, and share stories of successful neurodiverse individuals to normalize different approaches to work and thinking.

For neurodiverse founders, the takeaway is simple: embrace your wiring as your superpower. For leaders, make it your mission to identify, support, and champion neurodiverse talent.

Actionable Takeaways for Founders

• Regularly assess your engagement and market position to recognize when it’s time to exit.
• Don’t hold out for a mythical “perfect” offer, great opportunities rarely come twice.
• Prepare emotionally and practically for due diligence, earn-outs, and the loss of control post-sale.
• Systematize your business while maintaining enough involvement to preserve brand integrity.
• Build and nurture a personal brand that transcends your company.
• Embrace neurodiversity within yourself and your team, it can spark extraordinary innovation.
• Support neurodiverse individuals with encouragement, flexibility, and awareness.

Listen or watch the entire episode.

This article, “Peter Shankman Knows When to Exit” was first published on Small Business Trends