In this episode, ex-pro tennis player turned DTC founder Jack Oswald joins Adam and Pete to unpack what it actually takes to grow a product brand without sacrificing margins, sanity, or control.
Jack’s built Cancha, a modular bag brand now shipping globally, using a mix of bootstrapping, crowdfunding, fintech loans and angel investment. And he’s brutally honest about what worked…and what he’d never do again.
They cover:
– Why more money won’t fix messy operations
– The real risks of seller-based financing (hello, margin drain)
– How to test products without torching your cash
– Building a brand your customers will actually fund
– And how staying lean often leads to better decisions
This episode is for anyone growing a DTC brand and wondering how to fund it without falling into a cashflow death-spiral.
About the Guest
Jack Oswald – Former pro athlete and founder of Cancha. Navigated bootstrapping, crowdfunding, and external capital (sometimes the hard way) to build a lean, growing DTC brand.
About the Hosts
Adam Pearce – Co-founder of Blend Commerce and eCom Collab Club™, always hunting for what actually moves the needle.
Peter Gardner – Co-founder of Blend Commerce, CRO obsessive, powered by oat flat whites and sharp takes.
Work with Blend
Need your store to convert like your margins depend on it? Book a free “Metric on Fire” diagnostic: https://blendcommerce.com/
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