OpenAI just acquired Odessia, the AI travel agent Francis Davidson started less than a year ago, and he’s joining OpenAI to keep working on travel. The pod sat down with him right before the news broke. It’s a full circle moment, about ten years ago, Francis thought about starting an AI company, saw that a nonprofit called OpenAI was already on it, and went back to building his hospitality startup. Francis was a philosophy major at McGill with a near-perfect GPA who couldn’t land a single hedge fund interview, so he started renting out students’ empty apartments to travelers for the summer. He showed up in SF to fundraise with zero connections, a CRM of 50 VCs, and one strategy: ask everyone he met for intros to the top three people they knew. By 2019 Sonder was worth $1.1B and had signed leases to triple its supply. Then COVID hit and tanked revenue so much it literally broke their financial model. What followed was five years of operating in turnaround mode. Francis warned of impending bankruptcy to get out of leases, organized a “go public or die” SPAC, and a Marriott deal that finally got the business to break even after four years of struggling through Covid. Then the board fired him from his own company he started at 19. Four months later, Sonder filed for bankruptcy. The pod also gets into: Tokenmaxxing is not dead: Francis used 70 billion tokens last month and says his team got about 3x faster once he removed their token limitsBy his math, the world’s current compute can only support 500K to 1M people using AI the way he does, so he thinks we’re underbuildingHis biggest Sonder lesson: he should have let the turnaround guy take over. If your industry gets nuked, walk awayWhy he doesn’t expect mass job loss from AI, and why tour guide might be the job of the futureThey dig into what OpenAI just bought. With Odessia you can plan and book flights, hotels, trains and experiences over iMessage, WhatsApp, email or the browser. Behind the scenes, background agents have written a detailed report on every four and five-star hotel in the world, so it can rank 1,200 New York hotels in under a second on things no filter covers, like which floors are quiet or whether the gym has a squat rack. Finally, Francis talks about his wife Maria Davidson’s new $50M solo fund, Relational Capital, and what the best investors actually do for founders. 00:00 Dropping out of college as a philosophy major02:40 Making it in Silicon Valley with ZERO connections04:22 How Silicon Valley has changed over the last 10 years05:31 Managing 1,000+ employees08:19 Does Francis "believe" in philosophy after studying it11:22 COVID killed his hospitality company Sonder14:03 Trying to recover from a 100%+ drop in revenue14:59 How do labs project compute demand17:01 Hot take: tokenmaxxing works20:24 Taking a company public even though he didn't want to21:56 Fired from the company he started at 1927:10 Why he started a company a second time28:36 How do you decide to put an AI agent in a browser vs iMessage38:17 Who will actually use personal agents40:02 The future of work and labor economics46:11 Wife Maria's $50M solo GP fund Relational Capital This episode is brought to you by Kalshi. This week Jensen Huang publicly confirmed having an affair and over 50%+ traders on Kalshi think he’s out by the end of 2029 as the CEO of the world’s most valuable company. Sign up at kalshi.com/sign-up?referral=getthecheck and get $10 when you trade using our code GETTHECHECK.