Inman Connect Las Vegas returns live, Oct. 26-28, 2021, at the Aria Hotel and Resort in Las Vegas, Nevada. In the lead-up to the big event, we’re talking with scheduled speakers about the moments that made their careers. Consider this just a taste of all the knowledge that will be shared at ICLV. Make plans to join us.

Court Cunningham has been a presence in the startup community for over a decade, first as the CEO of Yodle, then as a board member at companies including InsightSquared, MINDBODY and Emissary.

Today, he is the founder and CEO of the New York-based real estate technology and alternative finance company, Orchard.

The startup serves as a dual-track for consumers who are buying and selling a home at the same time. Through a buy-before-sell guarantee, Orchard guarantees to sell a consumer’s home in 120 days. If Orchard doesn’t sell it, they buy it. The consumer is then able to use the capital promised in the guarantee to buy a new home before the sale of their old one.

Since its start, Cunningham has expanded Orchard into Colorado, Georgia, Texas, North Carolina, Maryland and Virginia. By 2022, the company plans on  adding four more markets to the list.

In an interview with Inman, Cunningham breaks down the three life moments that led him down the road to success.

High school woodworking

Cunningham took a woodworking class in high school and spent about three years building an 18th century mahogany desk.

One day, his teacher, Mr. Brown, came over to him and told him that some of the dividers for the piece were too loose.

Cunningham’s desk.

“He comes over and kind of shakes all the little dividers and says ‘Court, these are too thin, too loose,’” he said.

While Cunningham knew they were loose, he told the teacher that it was good enough, but Mr. Brown didn’t like his answer.

“He pulls every piece out — it was about three weeks of work — stacks it up, cuts it in half, throws it in the scrap box and says, ‘You’re better than good enough, start over,’” Cunningham explained.

That moment, he continued, taught him to hold himself to high standards and demand the best of himself.

Going to work with dad

When Cunningham was a kid, his dad would sometimes bring him into work. He had his own business shipping financial data to computer terminals around the U.S.

Seeing his dad build his own company taught Cunningham that success required dedication, a tireless work ethic and leadership.

In addition, going into work with his dad allowed them to spend time together and taught Cunningham the importance of maintaining relationships while building a company.

Action TNT

Growing up, Cunningham’s mom had a mantra: “Action TNT.” The meaning of TNT: today, not tomorrow.

That mantra still sticks in Cunningham’s head today.

“It just taught me there is real power to forward momentum,” he said.

Cunningham’s mom didn’t want him to be a shoot-from-the-hip type of person, but she encouraged him to tackle tasks right away and make the hard decisions sooner rather than later.

“Her perspective was, forward momentum is really valuable as long as you pivot directions a long the way,” he said.

Email Libertina Brandt

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