Why I Built Tippo: 20 Years in Restaurants Led to Fair Tip Sharing

My name is Jenna, and I have spent more than twenty years in the restaurant industry. I started at twelve years old as a Blizzard maker at Dairy Queen. From there I moved through hosting, serving, cocktail waitressing, and management — and eventually into opening my own establishments.

Across every role and every kitchen I walked through, one operational headache kept showing up: tip out.

What Is Tip Out in Restaurants?

Before I tell you why I built Tippo, it helps to name the problem every operator recognizes but rarely documents well.

Tip Out vs. Tip Pool vs. Tip Share

If you are not familiar with restaurant slang, tip out refers to the portion of a shift's tips that goes to team members who are not primary servers — cooks, dishwashers, hosts, baristas, and everyone else who keeps the floor running but does not take home the credit-card receipts directly.

Tip share (sometimes called a tip pool) is the broader idea that everyone who worked that day deserves a fair cut. The math is simple in theory. In practice, with rotating schedules, mixed roles, and different hours every day, it gets complicated fast.

Twenty Years in Hospitality Taught Me One Thing

That problem followed me through every stage of my career — not because the people running tip out were careless, but because the tools were never built for real restaurant complexity.

From Dairy Queen Blizzard Maker to Restaurant Owner

Managing tip out was consistently one of the biggest pain points I saw — as an employee wondering whether the split was fair, and later as a manager responsible for making the numbers work after a long service.

Opening Bliss Caffeine Bar and Choosing Tip Share

When I opened my own place, I had a chance to design tip share the way I always thought it should work.

Why Fair Tip Sharing Mattered from Day One

When I opened Bliss Caffeine Bar in 2021, I knew I wanted tip share from the start. Everyone who worked that day would get a cut of the tips. That was the easy decision.

The hard part was execution. We have more than twenty-four team members, multiple roles, and people working different hours every single day. I truly believed there would be an easy solution out there — a tip-out calculator that could split tips by position and hours worked without a fight at the end of every shift.

I searched endlessly. There was nothing affordable — or nothing that fit how a real café actually runs. So we built our own system in Excel. And honestly? It worked. But it was time-consuming for managers and opaque for staff. After years of struggling — and hearing the same frustration from others in my restaurant circle — it finally hit me: I need to make a tip-out app.

Why No Affordable Tip Out Calculator Existed

What surprised me was not that tip share was hard. It was that nobody had built an affordable tool to make it manageable.

What I Searched For (and Could Not Find)

What I wanted was straightforward: enter the night's tips, apply rules by role, weight by hours, and produce a breakdown everyone could trust. What I found was either enterprise software priced for large chains, or generic calculators that ignored the nuance of tip share.

Spreadsheets filled the gap, but the hidden costs add up: manager time after close, disputes when staff cannot see the math, and the quiet erosion of trust when nobody knows what to expect in their tip out.

Building Tippo: A Two-Sided App for Managers and Staff

That gap is why Tippo exists — and why we tested it at Bliss Caffeine Bar before offering it to anyone else.

How Tippo Works at Bliss Caffeine Bar

It took years to find the right people to build Tippo. We trialled the app at Bliss Caffeine Bar first, and splitting tip out at the end of each day became a breeze.

Tippo is two-sided by design. One side is for the person doing the work of splitting tips — usually a manager or owner. The other side is staff-facing. Every team member has a profile that shows what they made in tips after a shift and their total tips earned over any period they choose.

The team loves it because they finally know what to expect. No more lingering at the host stand waiting for someone to finish a formula. No more group texts asking, "Did anyone else's tip out seem low tonight?"

Tips Matter — and They Need to Be Fair and Transparent

Getting the math right is not just an operational detail. It shapes culture, retention, and whether your team trusts you after a long shift.

Why Killing Tips Would Hurt the Restaurant Industry

Tips are a crucial part of the restaurant industry. If we kill tips, we will kill the industry. They need to be handled in a way that is fair and transparent for all staff members — and that lets customers know their tips are shared with everyone on the team who made their experience possible.

As a restaurant owner, I know profit margins can be thin. That is why I priced Tippo at $9.99 for the first 100 users — because the tool should pay for itself in saved manager hours and fewer disputes, not become another line item that only big chains can afford.

The Vision: Make Tip Out Easy and Transparent

Tippo is not just software to me. It is the system I wish I had on night one at Bliss.

For Owners and Managers

The vision for Tippo is simple: transform the tip-out process. Make it super easy for owners and management to split tips at the end of a busy shift. Make it transparent and fair for every staff member who showed up and did the work.

If you run a restaurant, café, or bar and tip share is part of how you take care of your team, I built this for you — because I was you, staring at a spreadsheet at midnight, wishing the math would just be done.

— Jenna Oosterholt, Founder & CEO, Tippo