top of page

Disclaimer

The previous failure scenarios are fictional case studies developed by Exit Teams for educational purposes. While the businesses, owners, and details are imagined, each story is inspired by common real-world challenges faced by entrepreneurs during the business exit process.

 

These examples are not depictions of actual people or companies, and they are not intended as legal, tax, or financial advice. Outcomes in real transactions depend on many factors, including preparation, market conditions, deal structure, and advisor expertise.

 

Our intent is to help business owners learn from the costly mistakes others have made—and to show how planning, professional guidance, and timing can prevent similar outcomes.

 

Every exit has risks. The key is preparing early, seeking the right help, and learning from the experiences of others.

Losses: When Exit Plans Fell Apart

Not every exit ends the way an owner hopes. These cautionary stories explore what happens when planning comes too late, advisors are overlooked, or key details fall through the cracks. Each scenario is fictional but rooted in real-world mistakes that have cost business owners their legacies, their wealth, or both. Our goal isn’t to point fingers—it’s to highlight the avoidable pitfalls that can turn years of hard work into disappointment. Learning from these failures can be the difference between a missed opportunity and a successful transition.

Hal, 72 - Custom metal manufacturing

The Legacy That Died With Him

Hal built his fabrication shop from a single welding rig in the 1970s into a $12 million-a-year enterprise with 45 employees. His clients were loyal, his margins were strong, and he assumed the business could “sell itself” when the time came...

Amanda, 49 - Natural skincare and cosmetics manufacturing

The Deal That Died in Due Diligence

Amanda grew her skincare company into a nationally distributed beauty brand with $5 million in annual sales. She received an attractive offer from a private equity group that wanted to roll her company into a larger wellness portfolio.

Everything looked promising until due diligence revealed major issues...

Tom and Jake, 58 and 56 - Equipment Rentals

The Family Feud

Tom and Jake inherited their father’s equipment rental business. For decades, they made a good living—steady cash flow, loyal contractors, and a fleet of well-maintained machinery. But when Tom wanted to retire early, Jake wasn’t ready...

Simon, 61 - Medical device manufacturing

The Key Employee Exit

Dr. Patel’s company specialized in orthopedic implant design. He had several engineers who’d been with him for over a decade and handled all R&D and client relationships. When he began exploring a sale, two serious buyers emerged...

Ken, 66 - Regional trucking and warehousing

The Tax Time Bomb

Ken received an offer to sell his logistics company for $10 million. Excited, he signed a letter of intent and began spending like the deal was done—buying a vacation home and new vehicles.

But Ken never consulted a tax advisor...

Paul, 54 - Marketing and web design agency

The Silent Partner’s Surprise

Paul ran a boutique digital agency with 18 employees, specializing in hospitality marketing. He wanted out after 20 years to pursue travel and semi-retirement. He found a potential buyer—a regional firm eager to expand into Florida—and they agreed on a price; however, due diligence revealed a problem

Maria, 59 - Custom woodworking and manufacturing

The Deal That Couldn’t Be Financed

Maria’s handcrafted furniture line had a loyal following and solid financials—$4 million in annual sales and strong profit margins. A younger couple wanted to buy the business and keep her staff and brand intact. It was a perfect fit—until financing became the problem...

Ron, 67 - Commercial HVAC installation and maintenance

The Succession Plan That Never Happened

Ron assumed his long-time operations manager, Tyler, would take over the business when he retired. They’d talked about it for years—but never put anything in writing...

Leah, 43 - Graphic design and branding

The Burnout Exit

Leah was a talented creative who grew her small design studio into a million-dollar boutique agency. But after 15 years, she was exhausted. She planned to sell within a year, but instead of preparing, she simply stopped caring—cutting marketing, delaying hires, and letting clients slip away...

Donnie, 62 - Health and fitness

The Real Estate Trap

Donnie owned three profitable gyms, each in buildings he personally held through separate LLCs. He assumed buyers would love the setup—business plus property...

Dennis, 64 - Roofing and exterior contracting

The Unsolvable Lawsuit

Dennis had built a respected roofing company with over 25 employees and consistent revenue. He was ready to retire and had a serious buyer lined up—a national roll-up firm acquiring regional contractors...

Carol, 57 - Professional photo printing and imaging

The Market That Moved On

Carol ran one of the West Coast’s premier photo labs for professional photographers. For decades, she’d been profitable, and she assumed her niche expertise would make her business attractive to buyers...

Mark, 61 - Logistics and warehousing

The Buyer Who Vanished

Mark thought he had the perfect buyer: a private equity-backed logistics group expanding into the Midwest. The LOI was signed, due diligence was underway, and Mark even announced to his staff that the deal was happening...

Natalie, 52 - Commercial landscaping and maintenance

The Overleveraged Expansion

Natalie’s business was thriving—$8 million in annual contracts and a solid reputation. When she decided to sell, she wanted to push the valuation higher first. Her strategy? Rapid expansion...

David & Melissa, 50 - Data consulting and analytics

The Partner Who Wouldn’t Let Go

After 20 years of building Summit Analytics into a $10 million consulting firm, David and Melissa received a strong offer from a major tech integrator. David was ready to exit and enjoy early retirement. Melissa wasn’t...

Hal, 72 - Custom metal manufacturing

Hal built his fabrication shop from a single welding rig in the 1970s into a $12 million-a-year enterprise with 45 employees. His clients were loyal, his margins were strong, and he assumed the business could “sell itself” when the time came...

The Legacy That Died With Him

Amanda, 49 - Natural skincare and cosmetics manufacturing

Amanda grew her skincare company into a nationally distributed beauty brand with $5 million in annual sales. She received an attractive offer from a private equity group that wanted to roll her company into a larger wellness portfolio.

Everything looked promising until due diligence revealed major issues...

The Deal That Died in Due Diligence

Tom and Jake, 58 and 56 - Equipment Rentals

Tom and Jake inherited their father’s equipment rental business. For decades, they made a good living—steady cash flow, loyal contractors, and a fleet of well-maintained machinery. But when Tom wanted to retire early, Jake wasn’t ready...

The Family Feud

Simon, 61 - Medical device manufacturing

Dr. Patel’s company specialized in orthopedic implant design. He had several engineers who’d been with him for over a decade and handled all R&D and client relationships. When he began exploring a sale, two serious buyers emerged...

The Key Employee Exit

Ken, 66 - Regional trucking and warehousing

Ken received an offer to sell his logistics company for $10 million. Excited, he signed a letter of intent and began spending like the deal was done—buying a vacation home and new vehicles.

But Ken never consulted a tax advisor...

The Tax Time Bomb

Paul, 54 - Marketing and web design agency

Paul ran a boutique digital agency with 18 employees, specializing in hospitality marketing. He wanted out after 20 years to pursue travel and semi-retirement. He found a potential buyer—a regional firm eager to expand into Florida—and they agreed on a price; however, due diligence revealed a problem...

The Silent Partner’s Surprise

Maria, 59 - Custom woodworking and manufacturing

Maria’s handcrafted furniture line had a loyal following and solid financials—$4 million in annual sales and strong profit margins. A younger couple wanted to buy the business and keep her staff and brand intact. It was a perfect fit—until financing became the problem...

The Deal That Couldn’t Be Financed

Ron, 67 - Commercial HVAC installation and maintenance

Ron assumed his long-time operations manager, Tyler, would take over the business when he retired. They’d talked about it for years—but never put anything in writing...

The Succession Plan That Never Happened

Leah, 43 - Graphic design and branding

Leah was a talented creative who grew her small design studio into a million-dollar boutique agency. But after 15 years, she was exhausted. She planned to sell within a year, but instead of preparing, she simply stopped caring—cutting marketing, delaying hires, and letting clients slip away...

The Burnout Exit

Donnie, 62 - Health and fitness

Donnie owned three profitable gyms, each in buildings he personally held through separate LLCs. He assumed buyers would love the setup—business plus property...

The Real Estate Trap

Dennis, 64 - Roofing and exterior contracting

Dennis had built a respected roofing company with over 25 employees and consistent revenue. He was ready to retire and had a serious buyer lined up—a national roll-up firm acquiring regional contractors...

The Unsolvable Lawsuit

Carol, 57 - Professional photo printing and imaging

Carol ran one of the West Coast’s premier photo labs for professional photographers. For decades, she’d been profitable, and she assumed her niche expertise would make her business attractive to buyers...

The Market That Moved On

Mark, 61 - Logistics and warehousing

Mark thought he had the perfect buyer: a private equity-backed logistics group expanding into the Midwest. The LOI was signed, due diligence was underway, and Mark even announced to his staff that the deal was happening...

The Buyer Who Vanished

Natalie, 52 - Commercial landscaping and maintenance

Natalie’s business was thriving—$8 million in annual contracts and a solid reputation. When she decided to sell, she wanted to push the valuation higher first. Her strategy? Rapid expansion...

The Overleveraged Expansion

David & Melissa, 50 - Data consulting and analytics

After 20 years of building Summit Analytics into a $10 million consulting firm, David and Melissa received a strong offer from a major tech integrator. David was ready to exit and enjoy early retirement. Melissa wasn’t...

The Partner Who Wouldn’t Let Go

bottom of page