The Entrepreneur Experiment EE442 - From Side Hustle to €10M: The Mystery Shirt Story
In this episode of The Entrepreneur Experiment, Gary Fox sits down with Rory, the 22-year-old founder of Shirt in a Box, the mystery jersey startup on track to hit €10 million in revenue. What began as a lockdown side hustle selling vintage shirts has exploded into a full-blown e-commerce machine — with 200,000 shirts sold, 2,500 US subscribers, and viral moments like a surprise shoutout from Gary Neville on the UK’s biggest football podcast, The Overlap.
Rory breaks down how that single moment led to a 5x revenue day, why influencer marketing only works when it’s authentic, and how he's pivoted from student entrepreneur to full-time CEO building a creative agency within his business to produce 400+ ad creatives a month.
From boxing mishaps and marketing fails to future expansion plans in the US and new sports like basketball, this is an unfiltered look at what it really takes to build and scale a modern DTC brand.
“That Gary Neville shoutout was probably worth £150,000 to us… and we didn’t even ask him to do it.”
🧠 Show Notes – In this episode, we cover:
📦 How Shirt in a Box works — and why the mystery model taps into childhood nostalgia
🎯 The Gary Neville effect: a €150k shoutout from The Overlap
💥 The power (and problems) of viral growth: stock delays, customer service chaos & staff turnover
🧠 Why managing people is the hardest founder skill to master
🇺🇸 How Rory identified the US as a key market & grew subscriptions 100% from Ireland
👕 New sports, new supply chains: launching mystery basketball jerseys
🎥 Why they now produce 400+ pieces of ad creative every month
🧪 The best performing ad formats right now (including “fake podcast” ads)
🔄 From TikTok to Meta: what’s working (and what they’ve given up on)
🏪 Bricks & mortar dreams: future pop-ups and immersive retail experiences
Resources & Links
🎽 Shop Shirt in a Box
📚 The 4-Hour Work Week by Tim Ferriss
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