Pilot CEO Waseem Daher, Thursday Nights in AI

Outset Capital's Ali Rohde and Josh Albrecht interview Pilot CEO, Waseem Daher. Special thanks to Pilot for hosting us at their office!

This fireside chat is part of our 'Thursday Nights in AI" series, co-hosted by Outset Capital and Imbue.

Join our upcoming events! Line up here: https://www.outsetcapital.com/thursda...

About Outset: Outset Capital is led by Ali Rohde, Kanjun Qiu, and Josh Albrecht — AI practitioners investing in AI, deeptech, and the future of work. We back companies at the outset and love to be the first check in.

About Imbue: Imbue is an AI research company aiming to rekindle the dream of the personal computer—by creating practical AI agents that can accomplish larger goals and safely work for us in the real world.

Join our upcoming events! Full list here: https://www.outsetcapital.com/thursda...

Read Waseem's Substack, Startup Real Talk: https://waseem.substack.com/

00:00 Waseem Daher
01:52 What is Pilot and how is Pilot incorporating AI?
04:29 Why Pilot focuses on accounting
06:53 Why AI engineers should work in 'boring' industries
08:41 How Pilot's business changed with the rise of LLMs
13:25 On losing Pilot's 'moat' as AI advances
15:46 Whether other 'middle zone' startups will maintain their moat
18:41 How to keep customers: stickiness and convenience
20:18 Waseem's experience using generative AI
23:57 Waseem's one contrarian opinion when it comes to AI
25:07 On raising a kid in an AI world
25:50 Waseem's advice to founders
29:20 Fundraising is not the founder's end goal
30:33 Q&A