The Story Behind OvationCRM (And the Time I Got Locked in a Trunk on Stage)

Let me start with the trunk story, because it sets the tone for everything that follows.

My wife and I were performing at the New Jersey Magic Funday conference — real stage, real audience, real stakes. We were doing the Metamorphosis, which if you don't know it, is the illusion where my wife gets locked in a trunk, I stand on the trunk and throw a curtain up and my wife appears on top, and I'm supposed to emerge from inside. Great illusion. Spectacular when it goes right.

We had this thing rehearsed cold. The keys to the padlocks lived on our small rolling cart, same spot every time, every show. Before I stepped into position, I noticed a stagehand move the cart out of the way — it looked like I was about to bump into it. I thought nothing of it. We executed the switch, now I'm in the trunk waiting my wife to unlock it, I heard the applause, I heard the music go off.

And then I waited for the trunk to open.

Nothing.

Knock, knock, knock.

"Where are the keys?"

I am sweating inside a locked trunk on a stage in New Jersey, a thousand thoughts racing through my head, the audience laughing and having what appears to be a genuinely great time, and somewhere offstage a stagehand is sprinting back to my — I mean, my wife's — rescue.

We got out. The audience loved every second of it. But that particular brand of organized chaos? That is performing. That has been my life for most of my life.

I did my first magic show at nine years old. Since then, I've performed as a close-up and stage magician, a professional Santa Claus, a comedy hypnotist and mentalist, at fairs, schools, libraries, corporate events, private homes — across more venues and crowd sizes than I could give you an honest count of. The craft shifts, the audiences change, but the core of it is always the same: you show up, you create something in the room, and then you go home and figure out how to do it again.

The business side of performing, though. That's where things get messy.

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The Problem Nobody Was Really Solving

I've also spent decades in software — starting as a developer in the late nineties, growing into engineering leadership and technology executive roles over the years. My first real project was building a website for my Boy Scout troop. That grew into helping small businesses, then bigger ones, then eventually into a long career running technology at scale.

So I've always seen the entertainer world through two lenses at once: the performer who lives the business problems, and the builder who understands what it actually takes to solve them.

What I kept watching, year after year, was the same pattern.

Talented, busy, professional performers running their businesses on legal pads, email searches, and memory. Not because they didn't care. Because the tools available to them were built for a different kind of business and asked a lot in return for not very much.

In 2019, my Santa career was picking up steam and I started attending more training sessions and conventions. Almost every single one had sessions on business management — good teachers, genuinely trying to help. They'd go around the room and share what they were using. ManagerSal. Party Pro Manager. Spreadsheets. Various combinations of tools stitched together that, if you were patient and technically comfortable, kind of sort of worked.

But here's what I kept thinking about: the Santa community skews older, with an average age somewhere around 65. These are not people who want to spend a weekend configuring software fields and setting up integrations. They want to take the call, book the gig, show up, do something genuinely magical for a child, and get paid. The tools that existed were asking a lot for what they gave back.

I was sitting in one of those business sessions, half-listening to a presentation on contracts and deposits, when the thought finally crystallized: I should probably just build the damn app I've been sitting on for a decade.

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An Idea Ten Years in the Making

Here's the real backstory.

Back in 2011, I was performing magic full time and I wanted something to manage my bookings, my clients, my follow-up schedule. Nothing off the shelf fit the way I needed it to, so I did what any stubborn person with a software background does: I cobbled together a FileMaker Pro application for myself.

It worked well enough. Then performing slowed down, other things took priority, and the idea went to the back burner.

Where it sat for the better part of a decade.

I'd think about it occasionally. I'd file the idea away again. And then 2019 arrived and I was watching a room full of Santa performers try to navigate tools designed for, I don't know, dental practices — and the idea came roaring back.

The difference this time was that I had a plan. Rather than try to build something for everyone at once, I'd start small. I'd validate the concept in a tight community — one where I knew people, understood the workflows, and could get real feedback quickly. If the foundation was solid, I'd know. If it wasn't, I'd find out before it cost me too much.

The Santa community was that community. Small enough to learn from fast. Honest enough to tell you when something doesn't work.

I started talking to people about the idea. One person told me directly: "I think that is a waste of time and isn't needed. The community is too small."

That person is one of our power users now.

What changed their mind was a single afternoon. I walked them through the system — how it worked, what it tracked, how the pieces fit together. And then Stripe payments went live. Within an hour of getting a call, they had a contract signed and an invoice paid. In March. They told me they had never been paid before July for gigs booked months in advance.

That was the moment everything clicked.

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Launching Kringle Tracker

Kringle Tracker launched July 25, 2022. Built from the ground up, on less than five thousand dollars in startup capital, with a small team I trusted. No venture capital. No funding rounds. No pitch decks to investors who'd never been to a holiday party in their lives.

The marketing approach was equally unflashy: show up at Santa conventions, talk to performers, let the product do the convincing.

Within the first two and a half years, we crossed 100 users. Santas, mostly. Mrs. Clauses, elves, a handful of magicians and balloon artists and other performers who found their way in and decided to stay.

And as those performers from other parts of the entertainment world started using the platform, something became hard to ignore.

The problems were identical.

Magicians dealing with double bookings because they were tracking everything across three different systems. Fair performers losing client history between seasons because it was all in their head. Clowns chasing invoices. DJs managing multiple gigs with no central record of who hired them or what they'd paid before. The operational chaos I'd watched in the Santa community wasn't a Santa-specific problem.

It was an entertainer problem.

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From Kringle Tracker to OvationCRM

That realization drove the evolution into OvationCRM — a platform built for the broader community of solo and small-to-midsize performers who deserve tools designed around how they actually work.

The Kringle Tracker roots are still there and they always will be. That community is where the idea was proven, where the real feedback came from, where I first watched a performer get paid in March instead of the day of the event in December. But the scope is wider now because the need is wider.

I want to be clear about something. I'm not an outside observer who developed an interest in the entertainment industry and decided to build software for it. I'm a performer who got tired of watching talented people struggle with problems that had workable solutions. I understand what it costs when a double booking happens — not just the lost revenue, but the relationship damage, the embarrassment, the phone call you don't want to make. I understand what it feels like to get a call from a returning client and realize you have absolutely no record of who they are or what they booked two years ago.

I have been there. More than once. Across more than one performing identity.

That's why I built this.

This blog is going to be about the real, unglamorous, occasionally-locked-in-a-trunk business of being a professional entertainer. Business management, booking strategies, client relationships, the stuff that doesn't get talked about at the after-party but probably should.

OvationCRM is written and built by a performer, for performers. I hope you find it as useful as my loyal users and I.

In Time, Roger Minton