Serving Up a Startup: How Volleybird Turned Pickleball Frustration into a Scalable Sports Brand

On the premiere episode of Fork in the Road with Perry S. Kaufman, Perry sits down with Cassandra Toroian and Tracy Thomas, co-founders of VolleyBird, to explore how they built two businesses at the intersection of sports and entrepreneurship.

What started as frustration over a 70-page pickleball rulebook evolved into a sports rules app powered by proprietary AI. At the same time, they launched a subscription box company serving passionate players of tennis, pickleball, padel, and golf. Every 60 days, customers receive curated gear, apparel, and sustainable products they will not find in big box stores.

The conversation dives into:
• Why necessity sparked their first product idea
• How they pivoted their rules app from direct-to-consumer to a B2B API model
• The realities of customer feedback as founders
• Building a brand around sustainability and niche sports
• Why working for yourself is both harder and more rewarding
• What young entrepreneurs should understand before launching a business

Cassandra and Tracy also share how they differentiate in crowded markets by focusing on sustainability, women-founded brands, and unique products, including eco-friendly tennis balls designed to reduce waste.

If you are a founder navigating your own fork in the road, this episode offers a candid look at scaling, pivoting, and staying close to your customer while building something you truly believe in.