Episode #5: The Hidden Costs of Waiting Too Long to Sell Your Business

Episode #5: The Hidden Costs of Waiting Too Long to Sell Your Business

Most small business owners believe their business is their retirement plan. Fewer than one in four will ever sell it successfully. And the reason usually isn’t the market—it’s preparation. Today’s guest has seen thousands of deals from the inside and knows exactly why some businesses sell for top dollar and others don’t sell at all. Sometimes, it's a matter of timing.  I’m talking with Jessica Fialkovich, author of The Exit Factor, about what really drives value, what kills deals, and what small business owners should be doing now- even if they’re not planning to sell anytime soon. If you own a business and someday want options, this episode is for you. Find more episodes here. [https://htttp//www.isellyoursmallbusiness.com]

#3: Selling Your Business: Is It Like Breaking Up or Winning the Lottery?

What happens when you sell your company for $100M, but then find you have lost your identify and sense of belonging as a result? This shift happens for many exiting founders and can cause real problems in their lives.  My guest on the show is Dan J. Berger who is the Founder and former CEO of the Washington, D.C.-based Social Tables, which was acquired in October 2018 by Cvent for $100mm. Founded in 2011, Social Tables is an event planning SaaS platform used by over 50% of all full-service hotels in North America. At the time of sale, the company had $20M in bookings, 120 employees, and over 6,000 customers. Social Tables raised a total of $27mm. Dan is the author the book, "The Quest: The Definitive Guide to Finding Belonging You". Find more episodes here. [https://htttp//www.isellyoursmallbusiness.com]

#4 Is Selling Your Family Business Like Selling Your Childhood Home?

What happens when you are asked not to sell your business but sell your aging parents' business? Is it like selling your childhood home? How much more pressure does this put on you to get a successful deal done? My guest is Michelle Pippin who is the Founder & CEO of Women Who WOW, an online community and coaching platform for ambitious women entrepreneurs. She talks about navigating the sale of her family’s multi-million dollar construction business after a personal loss. Michelle shares the challenges of maintaining operations, negotiating with buyers, and ensuring a smooth transition for employees and clients. She emphasizes the importance of clean financials, clear communication, and emotional resilience. Find more episodes here. [https://htttp//www.isellyoursmallbusiness.com]

#2 How Peter Shankman Knows When to Exit

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! After 3 exits, this is exactly what my guest Peter Shankman knows how to do.  He is a top keynote speaker in marketing, social media, customer service, and neurodiversity in the workplace. The New York Times has called Peter Shankman “a rock star who knows everything about social media and then some.” With three startup launches and exits under his belt, Peter is recognized worldwide for radically new ways of thinking about the customer experience.   He three exits include The Geek Factory and Help A Reporter Out (HARO). Find more episodes here. [https://htttp//www.isellyoursmallbusiness.com]

#1 Behind the Scenes of a $140 Million Sale: Keith Schacht's Journey with Mystery Science

The Exit Strategy is a podcast where founders share the real stories behind selling their businesses—the good, the bad, and the ugly. From tough decisions to unexpected wins, we dive into what it really takes to walk away and what they did next. It's the good, the bad, and the buyout. Keith Schacht is one part inventor, one part explainer, and one part entrepreneur. He has started many companies and sold a few. his first was in college; He sold it his junior year and dropped out. His "first love" was a company called Inventables. It opened many doors like speaking at TED, meeting amazing people, and it had a modest outcome. His  biggest success was Mystery Science, he co-founded this with Doug Peltz, better known as Mystery Doug, and it became the most widely used science curriculum in American schools. I was privileged to be involved in the sale of this  company to Discovery Education in 2020 for a reportedly $140M. Here is a behind the scenes look at this sale.  Find more episodes here. [https://htttp//www.isellyoursmallbusiness.com]