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Eoghan McCabe is the Co-founder and CEO of Intercom, building Fin.ai, the AI customer service company. This was an extremely candid, two hour conversation going inside every detail of how Intercom was the first late stage software company to successfully re-architect itself to be AI-native. Intercom just announced they’ve built their own customer service-focused AI models, and Eoghan explains why most software companies will have to do the same. We also talk through the lessons he learned coming back to run Intercom in 2022 after stepping back in 2020, why many AI companies have strong negative gross margins despite the narrative, how Intercom designed AI’s first outcome-based pricing model, the challenges of buying AI software today, the importance of brand when building new products, and we get in the wayback machine, talking through the pain raising Intercom’s initial million dollar Seed round, and how venture capital has changed since then. Thank you to Eoghan’s Co-founder Des Traynor for helping me brainstorm topics for the conversation. Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeel Timestamps: 4:18 We’re at peak SaaS 9:11 Inside early days of Intercom’s turnaround 16:43 AI will beat humans at everything 21:17 Making trade-offs building AI products 24:25 Why Intercom trained their own AI models 28:33 Lessons from returning as CEO 34:19 Overcoming initial AI skepticism in 2022 40:02 Creating AI’s first outcome-based pricing 45:15 Intercom’s best-in-class gross margins 49:25 Why its so hard to buy AI software today 51:28 Unpacking AI’s negative gross margins 58:12 Being perfectly positioned for AI 1:07:01 How AI will change org design 1:09:47 Why AI products need their own brand 1:16:13 Founder CEOs vs Manager CEOs in AI 1:21:29 AI startup opportunities 1:24:57 Lessons running a team in Dublin and SF 1:28:25 How media has changed over time 1:37:32 Raising Intercom’s first $1 million Seed round 1:43:53 Why there are so many VC’s 1:47:38 Advice for investors Referenced Intercom: https://www.intercom.com/ Fin: https://fin.ai/ Intercom Careers: https://www.intercom.com/careers Eoghan’s website: https://eoghanmccabe.com Intercom’s first pitch deck: https://www.slideshare.net/slideshow/... Follow Eoghan Twitter: https://x.com/eoghan LinkedIn: / eoghanmccabe Follow Turner Twitter: / turnernovak LinkedIn: / turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/