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11 Hard-Earned Lessons From Selling a Struggling Business

January 15, 2021 |  

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Cracking the Amazon e-Commerce Code

Sophie Howard built and sold a 7 figure Amazon e-Commerce business in less than two years. Here’s how she did it.

The Pivot

Andrew Yang had built Manhattan GMAT into an $11 million business when Kaplan Test Prep, an 800-pound gorilla in the education business, threatened legal action against his company.

The 50% Bump

Stephen V. Smith built WordSouth, a marketing communication agency to 30 employees before a rare condition landed him in the Intensive Care Unit of his local hospital for seven weeks. Close to death, Smith gathered his team and began the heart-wrenching process of delegating his business's critical pieces to trusted employees. Little did he know at the time, that decision would be an essential element of building a sellable company.

The Backstory Behind Dream Water's $34.5M Exit

David Lekach started Dream Water; a natural sleep aid bottled in a 5 oz shot similar to the famous 5-Hour Energy Drink. Lekach built Dream Water up to almost $10 million in annual revenue before selling it to Harvest One, a cannabis company, for $34.5 million in cash and Harvest One stock.

When the Hunter Becomes the Hunted

Tom Farinacci II built Houston Green Leaf up to 35 employees when he solid it to Grounds Control, a national landscaping company, for around four times EBITDA.

The 8-Figure Trigger

Lee Gregory built Sir Lines-A-Lot, a company that paints lines on highways, to 40 employees. It was blue-collar work, so when Gregory learned his company could be worth north of eight figures, he decided it was time to sell. During this interview, Gregory drops dozens of knowledge bombs for aspiring value builders.

3 Ways to Untangle Yourself from Your Business

Debbie King was running on a treadmill so familiar to service company owners. Her company, Association Analytics, helped associations make sense of their member data, and she was wasting time on proposals that often did not get accepted. Then, when King did win a project, she was creating a custom solution for every job that required her to hire senior-level staff and personally get involved in client work. The model put a cap on her business, and when she reached 20 employees, she decided it was time to get out.

How To Overcome Owner's Guilt

Todd Kaufman and his partner Justin Searls started Test Double, a custom software development company, in 2011. The business was a success from the start and grew more than 25% a year. By 2019, Kaufman and Searls were generating more than $10 million in annual revenue and putting more than $3 million to the bottom line each year. An outside valuation consultant suggested if they ever wanted to sell, Kaufman and Searls could get around 6.5 times profit for their business or around $20 million.

Avoiding The Commoditization Rat Race To The Bottom

Jean-Eric Plamondon was in the scrap metal business where the stereotypical operator is a shady character buying metal by the ton with a blow torch in one hand and a wad of cash in the other.

How To Lose $200 million

Procrastinating the sale of your business? One entrepreneur shares a cautionary tale that reveals the best time to sell your company may be when someone’s willing to buy it.