How Silly Pickles Grew to 73 Metros Without Giving Away More Equity

Silly Pickles runs adult recreational sports leagues designed for people who want to meet new friends as much as play. Founded by Tommy Flaim, the business started with a single pickleball league run on TikTok and Microsoft Excel and has since grown to 73 metros across the US, with $6 million in annualised revenue. The league format matches players by skill level and keeps pre-formed friend groups in the minority, engineering the conditions for strangers to actually connect.

The league that started behind a bar

Tommy spent six years building Fox & Robin, a sustainable clothing alternative to Lululemon, before winding it down. He called it an unsuccessful venture, though the TikTok following and the knowledge of consumer brands he built along the way both found a second use. After Fox & Robin, he was bartending at a pickleball facility for extra money and something to do when he spotted the opportunity.

Pickleball facilities were struggling to attract younger people and first-time players. Tommy had the audience and an idea. He convinced the owner to let him run a league and used his TikTok platform to fill it.

The format he built addressed a tension at the heart of pickleball. Unlike kickball, skill level gaps in pickleball are immediately noticeable, and they stop the game from being fun. Tommy's system pairs players by ability each week, adjusting individual rankings after every night based on results. The scheduling logic had a built-in side effect: because you're always matched with different people at your level, you're continuously meeting new faces. The social goal was baked into the mechanics.

He ran the first leagues on Microsoft Excel formulas. They immediately took off.

Equity for the software, Wayflyer for the growth

Scaling out of a spreadsheet took two rounds of capital with very different purposes. There was no off-the-shelf software capable of running Silly Pickles' scheduling logic, so Tommy raised $750,000 in equity financing, most of which went into building a proprietary league management platform. With that in place, the operating model decentralised: leagues across the US are now run by local operators, a hairdresser in Delaware, a scuba instructor in Atlanta, a Chicago lawyer who joined to meet people. Tommy's team handles the platform, marketing, and product; locals handle the nights.

Entering each new market follows a predictable pattern. Paid acquisition in the first season consumes between fifty and sixty percent of revenue. By season six or seven, as referrals, word of mouth, and organic search take over, it drops to five or ten percent. Every new city loses money temporarily and then starts making it. The model was proven. What Silly Pickles needed was capital to fund the early-loss phase in each new market without giving away more equity to do it.

A recommendation from one of Tommy's equity investors pointed him toward Wayflyer.

I want to maintain as much ownership as possible. The more I looked into it, the more excited I got.

The process matched what the business needed: Wayflyer took time to understand the model, asked the right questions, and once the decision was made, moved quickly.

After the initial diligence calls, getting to know the business, getting to know myself, after making the decision to move forward, the process was incredibly seamless and very easy.

Twenty new markets and still expanding

The most recent Wayflyer funding enabled Silly Pickles to enter twenty new markets, taking the total from 63 to 73 metros. Revenue is running at $6 million annually, with the business approaching break-even across the portfolio.

The acquisition mix in each city evolves over time. Paid Instagram and TikTok ads carry the first season; a referral programme, local influencer partnerships, and organic search gradually take over. Each league becomes a source of its own growth through UGC and word of mouth, and the cost of acquiring players in an established market falls well below the early-season rates.

The vision ahead is the top two hundred US metros, with a broadening range of sports. Volleyball is already running. Silly Soccer launches in New York City this spring. The larger ambition is to be the company of choice for anyone trying to meet new people as an adult, whether they have recently moved to a new city, turned thirty and watched their friends scatter, or want to be somewhere that makes showing up alone feel normal.

We try to replicate freshman year of college vibes, where everyone's very receptive to meeting new people.

It's been fun to build. And it feels like we're just getting started.

Interested in following in Silly Pickles' footsteps? Wayflyer has funded over 6,000 businesses worldwide with $6 billion worth of working capital, backed by world-leading financial institutions. Apply in minutes and access funds in hours. Start your application today.