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Four years ago, Stripe froze Recharge's funds just a week before they were due to pay $1.5M in payroll. That moment set off everything that followed: a $270M raise in the 2021 frenzy, burning $9M/month, and a brutal reset—letting go of 70% of leaders—to rebuild Recharge around outcomes that actually move a brand: retention, LTV, and operational focus. In this episode, Oisin O’Connor tells the founder story without the PR gloss—what nearly broke the company, what saved it, and why the next decade of ecommerce won’t be dashboards, but agentic AI and a practical “Retention OS.” Chapters 00:00:00 – “Stripe froze our funds” 00:02:00 – From Agency to Recharge: 7 attempts before subscriptions hit 00:05:30 – PMF & Early Traction: Why Shopify needed a subscription backbone 00:08:30 – COVID Sugar High: Growth, over-hiring, and the hangover 00:11:45 – The $270M Raise: What changed (control, expectations, burn) 00:15:00 – Burning $9M/Month: The math that forced a reset 00:18:30 – The Reset: Firing 70% of leaders—principles, process, aftermath 00:22::30 – Founder Health: Panic attacks, boundaries, sustainable pace 00:25:45 – Comeback Plan: Focus, accountability, and customer outcomes 00:29:00 – The Retention OS: Offers, credits, upsell, LTV loops 00:32:30 – AI in ecommerce: Agents will take over dashboards (subscriptions, SMS, analytics) 00:35:00 – Why You’re Not Growing (Fixes): data, stack, creative, CAC/LTV ------------------------------------------------- Join 6,000+ DTC marketers who have zero waste on their ad spend and track every conversion for their DTC brands: https://www.linkedin.com/newsletters/... Get our app on Shopify: apps.shopify.com/littledata Follow us on LinkedIn: / littledata Connect with our Founder and CEO, Edward Upton: / edwardupton Check out our website: https://www.littledata.io/ Explore our case studies: https://www.littledata.io/case-studies Follow us on Twitter: @littledatauk