Yo Shirt

Ben Williamson spent nearly a decade at Apple as a senior-level engineer, working on infrastructure handling 360 transactions per second. But after leaving the company, he saw an opportunity to reimagine commerce through mobile devices. Yo Shirt emerged from the insight that millennials no longer wanted to shop in malls—they wanted personalized, unique products delivered on-demand. The app would let users transform their digital memories into custom-printed apparel.

Before raising capital, Ben invested significant time building out the product and supply chain infrastructure. "We spent a lot of time just building the product before we went after raise money...didn't want to make sure that we had adequate supply chain built out to really handle orders," he explained. In February-March 2015, he closed a priced equity round at $5M pre-money valuation, raising $1.1M and giving up roughly 20% of the company. The technology differentiated Yo Shirt from competitors: rather than stamping designs onto blank garments, they printed full-bleed designs on a single piece of fabric before cutting and sewing, ensuring superior quality and no white spots at seams.

By late 2015, the app had been featured by Apple 29-30 times, generating over 3 million downloads. The real breakthrough came through strategic brand partnerships. Working with Fallout Boy (known for their band selfies at concerts), Yo Shirt created a seamless concert-to-commerce experience: fans texted a code, received a text with a photo from that night's show, and could instantly purchase custom apparel featuring themselves in the crowd. "We sold...north of a thousand units off of them," Ben noted, across their multi-stop tour activation.

The unit economics were compelling: shirts priced at $36 with COGS of $16-18, yielding north of 50% gross margins—well above typical off-the-rack apparel. The company took an organic approach to marketing with "very limited Facebook spend" focused on profitable cohorts and retargeting, running content videos (like a woman picking flowers and designing them onto a shirt) at sub-one-cent cost per view. By the end of 2015, Yo Shirt had over 100,000 paying customers and processed $3 million in total revenue. The repeat behavior was strong: customers who received quality garments "typically start going wild," with many making multiple purchases. A venture capitalist in New York even reached out via Twitter requesting a rush order, which the team delivered in 72 hours.

Heading into 2016, Ben projected the company would hit $10 million in revenue. With 13 full-time employees and 95% of orders shipping within five days, Yo Shirt was positioned as a technology company first, not just an apparel retailer. Ben's vision extended beyond impulse purchases: he saw Yo Shirt as translating the social media endorphin hit—the desire for unique recognition—into the physical world. When Nathan Latka asked if he'd sell for $10 million, Ben demurred, arguing the technology's value in a larger organization would "be far in excess of $10 million." His long-term goal was "to see what the team's capable of and how far we can push this," with key inflection points like vertical integration potentially two to three years away.