When Business Underdogs Strike It Rich: Hat Tip to 2022 Kentucky Derby Victor

Pop Culture
The iconic Ben & Jerry’s ice cream chain has a location in downtown Saratoga Springs, N.Y. (Wikimedia Commons/Tyler A. McNeil)

Five weeks ago, the racing world was captivated by the underdog story of Rich Strike. He rallied from last place to win the Kentucky Derby Presented by Woodford Reserve in an 80.80-1 upset. He provided a great thrill for owner RED TR-Racing and trainer Eric Reed, but they were not his original owners. Rather, they claimed him for $30,000 out of his maiden win in his second career start at Churchill Downs last September.

With that astute purchase, his connections helped etch Rich Strike’s name as one of the greatest claims in racing history.

Horse racing isn’t the only field where people investing a relatively small amount of money made it big. Here’s some other notable businesses that got started with a small investment.

Tough Mudder

Since 2010, the Tough Mudder endurance event series has put athletes everywhere to the test. The series consists of obstacle course races as long as 12 miles at locales across the country. It was founded by British expats Will Dean and Guy Livingstone in New York City, who put the first event on via word-of-mouth advertising and a $7,000 budget.

Since then, the company’s value has surpassed $100 million.

Cards Against Humanity

A favorite party game of Millennials and Generation Z, Cards Against Humanity was launched in early 2011 through a Kickstarter campaign. Its original goal was $4,000, but it raised more than $15,000.

In its first year, it earned more than $12 million in profit, and has become one of the best-selling board games every year ever since.


Sara Blakely graduated from Florida State University in 1993 and got a job selling fax machines door-to-door. Frustrated with the quality of her pantyhose, she invested her life savings of $5,000 and moved to Atlanta to start Spanx in 2000.

The company’s value was estimated at $540 million in 2021. For a company that strives to “ensure you look as good as you feel,” that’s a heck of a feel-good story.


This trash removal company was launched in 1989 in Vancouver by Brian Scudamore with just $700 in start-up capital. In 1997, the company launched its first permanent franchise, and expanded outside Canada in 2000.

Scudamore, who dropped out of Concordia University to pursue his business, went on to launch Wow 1 Day Painting and Shack Shine. He’s also an author, publishing “WTF?! (Willing to Fail): How Failure Can Be Your Key to Success” in 2018 and “BYOB: Build Your Own Business, Be Your Own Boss” in 2022.

Ben & Jerry’s

The iconic ice cream chain has hundreds of locations, including one in downtown Saratoga Springs, N.Y. The first location opened in 1978 in Burlington, Vt., by Ben Cohen and Jerry Greenfield, who invested $12,000 in a renovated gas station from which they sold their product. The first franchise location opened three years later. The company was sold to Unilever in 2000. By then, the ice cream cham with modest beginnings raked in hundreds of millions in revenues a year.

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