EE439 - From 5 Cafés to 800 Locations: How Bobby Kerr Built and Sold Insomnia Coffee

In this episode of The Entrepreneur Experiment, Gary Fox sits down with one of Ireland’s most recognisable business voices, Bobby Kerr — founder of Perk, former CEO and Chairman of Insomnia, investor, broadcaster, and champion of Irish enterprise. Bobby shares his remarkable journey from starting his first business at 39 — remortgaging his house with a newborn at home — to building Insomnia into over 800 locations across Ireland through smart partnerships, relentless drive, and a willingness to bet on himself. He reveals the lessons learned from navigating the arrival of Starbucks, the power of merging with competitors to scale, and why focusing on multiple revenue streams saved the business more than once. Bobby also opens up about selling in 2018 after a cancer diagnosis, the freedom he’s designed for himself since, and the businesses exciting him today, from Bread 41 to Irish tourism. Whether you’re an early-stage founder or a seasoned entrepreneur, Bobby’s story is a masterclass in vision, resilience, and knowing when to play the long game. Show Notes In this episode, we cover: ☕ How Bobby spotted Ireland’s coffee culture shift before it happened 🏪 The first Perk café on Grafton Street — and why a turnover-based rent deal was a game-changer 📉 Surviving Starbucks opening next door (and why it helped sales) 🤝 The three-way merger that became Insomnia — and why owning 30% of something bigger was better than 100% of his own 📈 Growing from 5 cafés to 200+ shops and 600 convenience store locations 💡 Creating three revenue streams: high street, concessions, and convenience retail 🛑 The importance of multiple revenue streams to de-risk a business ⚡ Why Bobby sold in 2018 after recovering from cancer 🍞 Why Bread 41 is his “most exciting” current project 🌍 Opportunities in Irish tourism and the bakery market 🎯 What he looks for when backing founders (and why it’s “the jockey, not the horse”) 📚 Bobby’s top book recommendations, daily habits, and best investment advice Links & Resources Bread 41 – Award-winning Irish bakery: https://bread41.ie/ Endurance: Shackleton’s Incredible Voyage by Alfred Lansing The Spider Covenant by Brian Klein ----- Subscribe to our newsletter for weekly inspiration on Business, Brain and Body, as well as exclusive events, courses and more, straight to your inbox. It's free! https://www.mrgaryfox.com/subscribe-1 --- Visit my partners Enterprise Ireland: https://bit.ly/EIreland Azure Communications: https://bit.ly/azureEE Nostra: https://bit.ly/3HHwSMo