July 30, 2025

No More Math at 2AM: The Tip Tech That Let This Leader Build Bigger

After 26 years at Applebee’s, Denny LiPira made the leap from corporate stability to entrepreneurial growth. Now overseeing operations for Island Wing Company and The Toasted Yolk Café, he’s building something new with leaner teams, stronger culture, and smarter systems. In this episode of Digital Hospitality, LiPira shares how Kickfin helped eliminate the chaos of nightly tip-outs and gave staff instant access to their earnings. Integrated with Toast, it streamlines operations and builds trust

Interview Takeaways:

Kickfin Replaces End-of-Shift Chaos with Confidence: Before Kickfin, nightly tip-outs were time-consuming, error-prone, and cash-heavy. Now, Denny LiPira’s managers close faster, and staff still get paid the same day—without the stress.

Fewer Mistakes, More Trust: With Kickfin automatically calculating and distributing tips, human error is off the table. That means fewer headaches, cleaner books, and a smoother experience for both staff and leadership.

Betting on Yourself Isn’t Reckless—It’s Required: After nearly three decades at Applebee’s, LiPira walked away from a stable corporate career to build something new. His advice: “If you’re gonna do it, you’ve got to do it today.”

Episode Links:

Island Wing Company Online: https://www.islandwing.com/

Island Wing Company Instagram: https://www.instagram.com/islandwingcompany/

The Toasted Yoak Cafe Online: https://thetoastedyolk.com/

The Toasted Yoak Cafe Instagram: https://www.instagram.com/thetoastedyolk/

Kickfin Online: https://kickfin.com/

Kickfin LinkedIn: https://www.linkedin.com/company/kickfin/

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