Henry Hyder-Smith and Steve Denner started UK-based Adestra in 2004. Adestra is a digital marketing software that helps big companies handle email campaigns, among other things.

The company grew nicely. By 2016, it had around $9 million in revenue and a client list that featured some of the U.K.'s best companies. Hyder-Smith and Denner decided it was time to go beyond their borders and enter the U.S. and Asian markets. To fund the effort, they raised $7.2 million from the Business Growth Fund (BGF), one of the U.K.'s largest private equity groups. BGF's investment valued Adestra at around $35 million — a little shy of four times revenue.

Before Zoom, when you wanted to meet with a group of people remotely, you used a teleconferencing service. If you lived in Canada during the early 2000s, you probably used one of Frank Cianciulli's lines. 

These days, you're just as likely to watch a football game on a mobile phone as you are on an old-school TV. The technology that enables you to watch your favorite show on whatever device you have handy was made possible by Jason Flick. Flick co-founded a company called You.i TV with a vision to "own the glass." He struck deals to provide the user interface, which enabled content to be viewed across devices with the likes of the NFL, NBA, and just about anyone else who produces original content.

In 2014, Adii Pienaar started an email marketing platform for retailers, which became Conversio. By 2019, Pienaar had $2 million in revenue and 14 employees. 

In 2004, Cesar Quintero started Fit2Go, a meal delivery service in Miami. The business delivered healthy meals to office workers in South Florida, and by 2017, Fit2Go was earning 12% profit on $3 million in revenue. That’s when Quintero decided to sell half of his business based on a four times EBITDA valuation.

Mike Malatesta built Advanced Waste Services, a company that helped businesses dispose of their industrial waste, to $45 million in annual sales before a fateful lunch changed his life forever. It was with a division president of Covanta (NYSE: CVA) who saw acquiring Malatesta's company as the perfect way to enter the industrial waste industry. 

Despite starting with just $10,000 in 2004, Jon Morris built Rise Interactive, a digital marketing agency, to more than 100 employees before deciding to sell part of the business to Quad, a global marketing services provider. 

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.

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

Rob Walling started an email service provider named Drip back in 2012. Walling bootstrapped his growth to almost $2 million in Annual Recurring Revenue (ARR) when, in 2015, Clay Collins, the founder of Leadpages, came knocking. 

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.

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.

In 2015, Nathan Hirsch and his partner started FreeUp.com, an online marketplace of virtual assistants. Four years later, Hirsch and his partner were billing more than $12 million when they received an acquisition offer from a customer they couldn’t refuse.

In 2001, Adam Torres started Team Dynamix, a software used by colleges and universities to keep their IT department organized. 

David Jondreau built American Sign Language, a company that supplied interpreters on contract, to $2 million in annual revenue when he decided it was time to sell.

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