When Till Schmidt booked his first pickleball court, it was just four friends trying out a new game. Fast forward a year, and he’s running multiple sessions across 20+ courts every Sunday.
That kind of growth doesn’t happen by accident. Till combined smart hosting, a little structure, and the right tools to turn casual games into a thriving pickleball community.
Here’s how he did it, and what you can learn if you’re just starting to grow your own group.
Discovering the sport
Till grew up playing tennis and ping pong, but pickleball wasn’t on his radar until a friend dragged him to a game in spring 2024.
He thought it was kind of silly at first. But once he played, he was hooked.
The next week, Till booked a court himself and invited three friends. Everyone had a blast. Soon, he was booking multiple courts and inviting more people each week.
At the same time, he had just started a career in real estate. Pickleball became both a passion and a way to meet people. “I started inviting people everywhere I went,” he told us. “It just grew from there.”
The early days: Instagram, Google Forms, and Venmo
Like a lot of new organizers, Till’s first systems were a patchwork:
- Weekly group chats on Instagram
- Google Forms to manage RSVPs
- Venmo to collect payments
It worked fine at first, but once he hit 20 players, things got messy. “The no-shows were tough, and I was spending too much time on logistics," Till said.
Moving to Pickleheads
Till mentioned in his group chat that he was looking for a better system. A player suggested Pickleheads.
“It was exactly what I’d been looking for. Now I can create sessions, set them to recur automatically, and track who’s really in or out.”
He still uses Instagram to attract new players (follow him here!), but once they’ve come out, they join his Pickleheads group and start signing up through the app.
The turning point: Charging for sessions
A few months in, Till’s games were up to 3–4 courts and costing $130+ per week. The no-shows were also piling up.
That’s when he started charging.
“Charging solved two problems at once,” he said. “It covered my costs, and players took the sessions more seriously. The drop-out rate went way down.”
He started by charging just above cost to give himself a small buffer. Over time, the sessions became not just sustainable, but profitable.
Scaling up: 60+ players every Sunday
Today, Till runs three sessions every Sunday:
- 1 advanced session
- 2 mixed-level sessions
- 6–8 courts per session (20+ courts total)
Depending on the week, between 60–100 players come out. His biggest turnout so far? Nearly 100 players in a single day.
Recurring sessions and built-in payments on Pickleheads keep things organized without endless back-and-forth.
Building community: What makes it work
Not every group wants structure. Till’s players prefer a social-first setup where they can pick partners and rest when they want. Instead of rigid formats, Till uses wristbands to sort players by level:
- Black = advanced
- Blue = intermediate
- Orange = beginners
Other little touches make the experience special: music, water, and weekly group photos that he posts to Instagram. “That’s been my #1 growth driver.”
Advice for new organizers
When asked what he’d tell someone just starting out, Till kept it simple:
- Keep it invite-only at first—focus on quality, not quantity
- Be a good host—welcome people, make it social
- Start charging early—you need to cover costs and reduce no-shows
- Take group photos and share them—social proof drives growth
- Invite people who are fun and welcoming—culture is everything
What’s next?
Till isn’t slowing down. His dream is to build his own courts so he’s not dependent on outside venues.
“Court availability is the bottleneck,” he told us. “If we had our own courts, we could expand without worrying about getting bumped.”
From four friends on a single court to a thriving 100-player community, Till’s story shows what’s possible when you combine passion, consistency, and the right tools.
