The Entrepreneur Experiment

EE433 - Raising €4M To Automate the Painful Side of Business


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In this episode of The Entrepreneur Experiment, Gary Fox is joined by Ross and David, the powerhouse duo behind Outmin, a game-changing AI bookkeeping platform. What starts as a conversation about longevity, biohacking, and raw vegetable breakfasts quickly evolves into a masterclass in building a deep-tech startup from scratch.

From rejecting vanity metrics and confronting brutal truths in fundraising, to rebuilding the accounting infrastructure and quietly revolutionising an unsexy space, Ross and David reveal how Outmin went from an idea to a VC-backed company with 350+ customers across Ireland and the UK. With €4 million in fresh funding and a bold roadmap for the future, they’re not just talking about AI - they’re redefining what it actually takes to automate one of the most painful parts of running a business.

This is a must-listen for founders, operators, and anyone curious about what building a truly differentiated startup looks like in the age of AI.

Show Notes

In this episode, we cover:

🧠 Ross’s “Cheat Death” document: longevity, raw vegetables & bioavailable supplements
💥 Why Outmin rebuilt the general ledger from scratch
🧮 Automating the “toothbrush task” of bookkeeping
🔍 How their dataset became their competitive advantage
📊 Why the AI wave is really a “plumbing” revolution
📈 Fundraising lessons from €0 to €4M
🧪 The importance of testing over storytelling in early-stage startups
💡 How they used public data to book 100+ customer discovery calls
📉 Why tech startups are harder to automate than hospitality
👥 The underrated power of building for 100 people who love you

💬 “If I could inject how I feel every day into someone else—they’d never go back.” – Ross

Links & Resources

Outmin: https://outmin.io

Enterprise Ireland HPSU Program: https://www.enterprise-ireland.com/en/innovative-hpsu-fund

The Data Collective VC analysis: https://dcvc.com

Singularity University: https://su.org

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