A Domer swims with the sharks

How startup Rent Like a Champion lured a pair of billionaires on Shark Tank

Blinding stage lights. 
Pin-drop silence. 
Ten fierce eyeballs trained on my freshly shaved head.

And I couldn’t speak.

I was poised to deliver a pitch on ABC’s hit reality show Shark Tank to multi-millionaire business magnates including Kevin O’Leary and Mark Cuban — but first I had to wait until makeup artists appeared to powder the shine on my own golden dome. Abruptly, the producer signaled me to dive in.

This was my make-or-break chance to pitch our startup company, Rent Like a Champion. Potential outcomes ranged from getting our home-rental concept demolished on national television, to landing a megawatt investment deal and propelling our business to new heights.

To secure a deal, I knew it would take passion, enthusiasm, resilience and energy. I brought it all — whooping, gushing, self-deprecating, blowing a slide whistle and even signaling a touchdown — while our CEO, Mike Doyle (ND ’12), methodically laid out our basic business model.

“Rent Like a Champion solves a very real lodging problem in college towns like South Bend, Ann Arbor and Tuscaloosa by connecting fans with homes near campus for big-event weekends,” he explained.

While we delivered the pitch, I got as worked up as I would on an ND Game Day. But O’Leary stalled me, blurting, “Slow down! I’m afraid you’re going to spontaneously combust!”

An interruption like that would leave many people dead in the water. But I laughed it off (I thrive on humor). I grew up just outside Minneapolis, snowboarding and goofing off in a blended family of six attention-hungry and competitive children. Getting parental attention required being vocal, daring or funny. Just like in my childhood, I had to grab the sharks’ attention in order to get the deal. Think American Idol for capitalists; I needed to do a little song and dance.

Like many success stories, Rent Like a Champion was born by accident. I enthusiastically attended Notre Dame as an undergraduate, studying finance and computer applications. By age 21, I became the youngest employee at IBM’s headquarters in Armonk, N.Y. Later I was hired as the 100th employee at a young startup travel company called Orbitz.

Upon returning to South Bend in 2006 for an MBA, I found home prices to be extraordinarily low and rents unusually high. My pal Derrick Shenk (FIN ’01) agreed, and with visions of becoming real estate magnates, we bought four houses before I even showed up to my first class.

But we’d goofed big time by failing to recognize that students typically lease housing a year in advance. After buying and rehabbing the homes, finding tenants just as classes were starting felt like snowboarding uphill. Desperate, Derrick and I thought we could keep the lights on by renting our houses for football weekends. Nobody was doing it; Airbnb didn’t even exist yet.

After furnishing our properties with free Craigslist finds, we posted rental auctions and pictures on eBay. With the free market at work, we soon generated more cash in a single weekend than in a normal month’s rent. A new business model was born: Buy a home, rent it out online for football weekends, and then move students in the following year. In addition to my MBA diploma, I left South Bend in 2008 with deeds to 35 homes. Talk about a rebound!

The Gigot Center for Entrepreneurship helped us incubate our idea, refine our pitches and avoid pitfalls. As part of the MBA course Funding New Ventures I prepared a solicitation for investment. My friend, serial entrepreneur and IrishAngel Jordan Curnes (FIN ’01) saw it and was interested, and he became our third founding partner. Jordan implemented an undergraduate internship program, which led us to then-sophomore, now-CEO Mike Doyle.

Our team complete, Mike pitched the partners on an expansion of the weekend rental model to Penn State. It worked famously, and we subsequently mapped out a dozen more college towns for future expansion. After he graduated, we hired Mike as CEO. By 2015, Rent Like a Champion listed more than 1,000 homes nationally, with gross receipts in excess of $6 million.

Mike applied to Shark Tank with his typical go-for-it verve, but didn’t hear anything for months. Then one day, our phone buzzed with an unknown L.A. area code: “Shark Tank producer here. We want to fly you out to pitch in the tank.”

To prep, I decided to devour as many Shark Tank episodes as possible. But on the first episode, the entrepreneur froze up. With sweat streaming from his forehead, he lost the track of his pitch and completely blew it.

I cringed. I didn’t want that image in my head. We pivoted and started pitching to real angel and venture capital investors, often with Notre Dame ties. They peppered us with tough questions, especially zeroing in on weak spots. We felt ready.

On the eve of our pitch, we learned of a surprise addition to the panel of sharks: billionaire Chris Sacca. Between Twitter, Instagram, Kickstarter and Uber, Sacca is a legendary angel investor. But more importantly, Mike had listened to a podcast where Sacca revealed a huge regret — he’d turned down a chance to invest in Airbnb, which is now worth more than $20 billion. He had been too worried about renters literally burning down a house.

Knowing about Sacca’s one-that-got-away, Mike emphasized our tiny (1.9 percent) incident rate over thousands of rentals and instead pointed to our great growth potential. Satisfied, Sacca convinced Cuban to partner up, and collectively they offered to invest $200,000 for a combined 10 percent stake in Rent Like a Champion.

Irrepressible as I am, I further negotiated, thinking we could create a multiple-offers situation among the sharks. Bad decision. Nearly fatal.

“Just be careful — you look a gift horse in the mouth, you might get your nose bit off,” Sacca warned me.

“When I get advice like that I know when to stop talking,” I said with a nod and gulp. We agreed to the deal. Not until we were strolling off the set would I holler, “Touchdown!”

We appeared on Shark Tank in mid-June and closed the deal in August. In that 10-week window, we had to become a Delaware-based, share-issuing C-corporation and find an affordable attorney who could go head-to-head with Cuban’s attorneys in areas such as convertible notes, option schedules and voting rights. Plus, under a strict confidentiality agreement, we couldn’t disclose the outcome, which was hard because I sing like a canary. Finally, the money hit the bank, the show aired on October 30, and the cash register really started ringing.

Sacca and Cuban have been very supportive and surprisingly accessible. Both are pushing growth acceleration while providing assistance with non-core business activities, allowing us to focus on results. For instance, we no longer sink time into accounting or payroll as Cuban’s corporate group picked up these functions. We hope to repay our noteworthy sharks by setting up an epic tailgate at a “neutral” site that both SUNY and Georgetown alum Sacca and Pitt and IU graduate Cuban will enjoy.

On the horizon we’re planning to bring Rent Like a Champion to large, non-collegiate events in small towns (think NASCAR or PGA), and we’re enlisting our more famous investors’ help. Can you imagine what happens when someone like Mark Cuban, the owner of the Dallas Mavericks, calls and asks for a meeting?

I may look a gift horse in the mouth, but I’m not afraid to swim with these sharks.