Our guest, Raj Aggarwal, was consulting for Apple in 2005 on the iPhone's business model, specifically the telecom side. Mid-negotiation, AT&T (then Cingular) kept raising concerns about the risk they were taking on. Jobs' response: just hand them a billion dollars in cash, and if the iPhone flopped, they could keep it. Someone suggested structuring it as a bond instead. Jobs said no, just write the check.

What stood out to us wasn't the number, it was what it did to the room. It ended the debate instantly and signaled a level of conviction that made everyone else fall in line.

Raj took that experience into his own career:

* Co-founded Localytics in 2008, two weeks before Lehman Brothers collapsed. Bootstrapped through the financial crisis before eventually raising money.
* Scaled past $25M in revenue, raised $60M, eventually sold the company.
* Built a second company, acquired by Snapchat.
* Spent a year at AWS running GenAI, where he watched a lot of Fortune 500 companies build AI demos that never made it to production (his read: they weren't connecting the AI to their actual enterprise data).

Now, he's building something new. 

  
Listen to the full episode on YouTube, Spotify, or Apple Podcasts.

We interviewed a founder who watched Steve Jobs offer AT&T a billion dollars in cash to end a negotiation. Full story on our podcast.