Digital Hospitality

Digital Hospitality


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

July 30, 2025

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:


About Our Sponsors DAVO:

DAVO automates every step of the sales tax process — from collecting to filing to paying. It works seamlessly with your POS, so there’s nothing you need to do. And because DAVO guarantees your taxes will be paid on time and in full, there’s nothing to worry about either.

Click here to learn more
Marqii:

Digital Hospitality doesn't have to be complicated and our partners at Marqii live that every day. Marqii is designed to create unforgettable customer experiences from first search to latest visit with their one-stop digital operations platform built for hospitality operators.

Click here to learn more