How Cartwheel found its first 100 customers

Rui Almeida, Founder & CEO at Cartwheel, on the messy early months: what worked, what wasted time, and the one channel that changed everything.

RRui AlmeidaCartwheelJul 29, 20266 min305

The starting point

When Rui Almeida started Cartwheel, there was no launch list, no press, and no budget. The first version shipped to a handful of people who had complained loudly about the problem in public.

What actually worked

"We stopped trying to be everywhere," Rui Almeida says. "We picked one community, showed up every day for three months, and answered questions we were not paid to answer."

That patience compounded. Referrals from those early conversations still drive a meaningful share of signups at Cartwheel today.

What wasted time

Paid acquisition before product-market fit. A rebrand that nobody asked for. Three months building an integration one prospect requested and never used.

The turning point

Customer number 41 wrote a public teardown of how they used the product. It was not flattering everywhere, but it was specific, and specificity travels. Signups tripled that week.

Advice for founders one year behind

"Write down the exact sentence your best customer uses to describe you, then put that sentence everywhere. Most positioning problems are really listening problems."