When Will Tams started Road to 4.0, signups were a spreadsheet and payments were Venmo at the court. Two years later: 4,531 players served, 539 sessions hosted, 93% sellout rate. Every pain point he hit, I turned into a fix. This is the platform that runs his business.
I Can Build This For YouWill Tams wanted to start a pickleball coaching business in the East Bay. He'd coached Ultimate Frisbee and baseball for 25 years, but pickleball coaching was new. He wanted to focus on what he's best at, the coaching, but everything else was pulling him off the court.
Signups were a Google spreadsheet. Payments were Venmo when people showed up. Half the time he didn't know who'd paid until the lesson started. Off-the-shelf SaaS didn't fit a small coaching business, and he had no in-house engineering. Every operational problem was his to solve, alone, between coaching sessions.
Then the first clinic sold out. Then the second. The pain points started compounding.
Will brought me in to build the custom software his coaching business needed. He'd run Road to 4.0 and do the actual coaching. I'd build the platform underneath it, one pain point at a time.
No roadmap. No big design phase. Will would hit a wall on Tuesday (a refund chase, a no-show wave, a roster mismatch) and I'd ship a fix by the weekend. Every pain point became its own working session: what's actually broken, what would solve it, and what's the smallest version I can ship before the next clinic.
Before I got involved, signups lived in a spreadsheet and money lived in Venmo. There was no way to actually reserve a spot, and no clean way to keep track of who'd paid for what.
It wasn't a business yet. It was a hobby with money attached.
The fix was the foundation: a real signup flow with Stripe Connect, where paying is reserving. No payment, no spot. Roster auto-built from confirmed payments. Refund policy enforced by code. The day this shipped, Road to 4.0 stopped being a hobby.
"I'm running signups on a spreadsheet and chasing Venmo payments at the court. This isn't a real business yet."
Pay-to-reserve signup flow with Stripe Connect. Players reserve their spot only after payment. Roster builds itself from confirmed signups.
In pickleball, the math matters. You need clean sets of four. One no-show and your courts are off. One late arrival and the coach has to stop and catch them up, which means the players who showed up on time get less of the lesson they paid for.
Will couldn't babysit sixteen people's calendars every week. He needed the system to do it.
The fix was simple, and it worked. Every session got automated reminder emails: one 24 hours out, one 2 hours out. Players actually showed up. The ones who couldn't make it had time to refund or cancel cleanly. Everyone else got a real lesson.
"People sign up but don't show, or show up late. Either way, the lesson is broken. The math doesn't work, and on-time players lose out because I'm catching latecomers up."
Automated reminder emails 24 hours and 2 hours before each session. Zero manual work per session.
Every pain point I had, Chuck turned into a fix.Will Tams · Founder, Road to 4.0
Pickleball players really, really, really want to be matched by skill. When skill levels are mismatched, the better players get bored, the weaker players feel exposed, and the lesson feels off, even when everything else is working.
The very first drill group, sixteen people showed up and there was no way to sort them. Some were total beginners, some were edging toward 4.0. They all played on the same courts, in the same drills, and most went home thinking "that wasn't quite for me."
The fix had two pieces, working together: players self-rated their skill at signup, and the roster auto-sorted them onto courts by skill level. By clinic three, the problem was gone. Reviews went up. Retention went up. Players told their friends.
"Beginners and advanced players on the same court. Nobody's getting the lesson they came for."
Skill self-assessment on signup, plus a roster that auto-sorts by skill onto separate courts. Two pieces, one outcome: players matched correctly from the moment they walk on.
The three above were the biggest. They weren't the only ones. Every week brought a new wall, and every wall got fixed before the next session.
What am I going to call Yelp and ask them for? You'd be lucky if a year later there was functionality that dealt with it.Will Tams · on what makes custom-built different
These are unsolicited emails from players after their sessions. They don't know (or care) what's running in the background. That's the point. When the operations are right, players feel a business that's well organized without ever needing to know why.
"That clinic was great. Well organized, informative and fun. I look forward to taking another one and drilling in the interim."
"Random people come to me to tell me how much better I've gotten…and more importantly, I'm having even more fun! On Saturday someone told me she could not believe I was the same person. She thought maybe I was a body snatcher!"
"Within a week I am seeing a positive impact on my game. Will gave in-depth training on the 3rd shot drop/drive, positioning after the return, dink drills, and paddle position."
Road to 4.0 is what happens when a coach with a real program gets a builder who can take friction out of the business as fast as friction shows up. Every feature on this page started the same way: a wall hit on a Tuesday, a fix shipped by the weekend, permanent infrastructure by the next session.
Will's business kept growing. The platform underneath it kept growing too, supporting his sub-coaches, his tournaments, and a community of players that has now passed 4,500. The platform got so good that other coaches started using it too.
It's now DailyPB, the pickleball event platform for the East Bay. Other coaches and hosts run their own programs on the same infrastructure that started as Will's signup form. Take a look if you want to see what it grew into.
That's the model I bring to every client engagement. Find the pain point. Build the fix this week, not next quarter. Let it compound.
A 30-minute call. No pitch. Tell me your biggest pain point and I'll tell you what an afternoon of work could do to it.
Book a callOr email chuck@startuptosold.com