At age 36, Greg Alexander decided to start Sales Benchmark Index (SBI), a sales consultancy. Over the next eleven years, Alexander built the business to 30 employees who collectively generated about $30 million in consulting fees per year.

Pete Martin built EntryPoint Consulting to 34 employees when he sold it to KPMG for a staggering 12 times earnings — without an earn-out. 

Jack Rivlin co-founded The Tab, a U.K. based media company that published digital campus newspapers across the U.K.

After ten years, The Tab had earned almost 6 million unique visitors and raised $10 million of capital from the likes of investors, including Rupert Murdoch's News Corp. Things were looking up for The Tab, but when an attempt to crack the U.S. market failed, things started to unravel.

Ryan Daniel Moran built Sheer Strength, a supplements business, up to a run rate of around $10 million per year when he decided it was time to sell. 

Saud Juman built PolicyMedical, a company enabling hospitals to document their procedures and policies, into a software company growing 100% a year when he sold it for 7.2 times revenue. It was a remarkable exit for a business Juman started in his mother’s basement.

Tyler Jefcoat co-founded Care to Continue, which provides in-home care for seniors, in 2012. Jefcoat built the company to more than 100 employees when he got an offer from a private equity group for more than five times EBITDA. Jefcoat was thrilled. The only problem? His partner wasn't ready to sell, which kicked off an acrimonious battle ending with Jefcoat selling his shares back to his partner. 

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.

In 2002, Lee Richter and her husband bought Montclair Veterinary Hospital in Northern California. Californians were embracing alternative medicine, and the Richter’s wondered if their affluent customers would invest in holistic therapies for their pets.

Mark Timm built Cottage Garden, a company selling decorative music boxes, to $8 million in revenue and around $1 million in EBITDA when he decided to sell it. 

Timm sold the business for around 4.5 times EBITDA. He got half of his cash up front, with the other half paid over a five-year earn-out. Timm not only stayed for his earn-out, but when the acquirer decided to move the offices of Cottage Garden, Timm agreed to repurchase the business, only to sell it two years later, for a second time.

If you're feeling exhausted from running your company, you can take a little solace from Michael G. Dash. Dash built Parallel HR Solutions, a staffing company, up to around $5 million in revenue with clients like Overstock.com, Goldman Sachs, and Discover Channel.