Local startup helps you ‘Squeez’ into last-minute reservations

Chris Ogboke compares his mobile app to a digitized $50 handshake at the door as it makes once-unavailable reservations accessible. 

Ogboke quietly launched Tampa-based Squeez in November 2024. The local startup helps busy people secure last-minute tables or tickets to popular shows and events while maximizing revenue for participating businesses. 

Squeez became part of Microsoft’s Founders Hub in July, and Ogboke launched with Caesar’s Palace, the prominent Las Vegas casino, in March. He said people typically pay $5 to $25 to ensure a spot in a busy establishment. 

“We all want what we want, when we want it,” Ogboke said. “We’re more than happy to pay for the time, access and convenience.”

Squeez users submit how much they are willing to pay for an unavailable reservation. Businesses can then accept or decline an offer. 

Ogboke noted that restaurants typically have slim profit margins and could use the additional money and patronage during off-peak hours or when someone no-shows for a reservation. The platform and business split the fee.

“By the time you park the car and start to walk to see if you can get in somewhere, you’re winging it at that point,” Ogboke said. “If you can send $10, $15 in advance to have no issues when you get there, you’re doing that deal all day long.” 

While the fee is typically nominal, Ogboke said the now-relieved guest significantly contributes to a restaurant’s bottom line. An upscale buffet in Caesar’s Palace offers Squeez as a “skip the wait” mechanism, because even with a reservation, you could be waiting half an hour.” 

“I’ve heard the investor community call it the new Disney Fast Pass,” Ogboke added. “If you can squeeze in, what’s it worth to you?”

He noted that most restaurants do not capitalize on last-minute openings like airlines or hotels. Meanwhile, in the age of on-demand food delivery services, consumers are willing to pay an additional fee to have something “there when we need it.” 

Ogboke, a member of the local Embarc Collective startup hub, called Las Vegas a “no-brainer” market for a pilot phase; he is equally excited to launch in Tampa Bay. “We’re not Miami yet, but everybody’s got disposable discretionary income,” he said. 

The idea for Squeez came to Ogboke when he and his busy colleagues struggled to secure early tee times for a quick round of golf and get home at a decent time to be with their young children. While investors and mentors encouraged him to focus on restaurants, the startup has now entered the world of sports. 

Ogboke is now working with Supreme Golf, which powers Barstool Sports. The popular digital media company now has a platform that enables users to browse and compare millions of online tee times. 

“So, that helps me get those 17 million folks on Instagram,” Ogboke said. “Then we can start figuring out how to put my technology in their technology, and see where we go from there.”

Squeez is welcoming new businesses, and Ogboke said he could onboard any local restaurant or company within 24 to 48 hours. However, he is focusing on securing deals with enterprise point-of-sale system operators and other reservation systems with thousands of clients. 

“But I’m more than happy to onboard an individual couple of restaurants,” Ogboke said. “They can use it for either their membership platform to build out a loyalty network, or use the Squeez functionality for wait lists.

“I’m kind of relaxed now because I’ve got so much good feedback from the Caesar’s pilot. I know people will pay what they need to pay to get what they want, when they want it.” 

The Squeez platform. Image: Screengrab.

Ogboke co-founded Gale Healthcare Solutions, the nation’s first company to offer “on-demand” technology-enabled nursing staffing solutions. The Tampa-based, self-funded startup grew to over $200 million during his tenure.

In August 2022, Inc. magazine ranked Gale among the top 20% of America’s fastest-growing private companies in August 2022. Ogboke exited the company and used some of the proceeds to acquire his own technology company and launch platforms like Squeez.

The experience taught him the importance of creating “your own destiny,” which includes “controlling your own tech.” Ogboke is now “laser-focused” on building out the platform through partnerships and onboarding additional businesses.

“It’s all about relationships,” Ogboke said. “I’m just enjoying the process and being diligent to control my own destiny.”