Where this was said
AI Startup Examples: Stuut, Harvey, and Pylon
At 9:50 · chapter starts 6:35
With the framework established, Elena pushes for concrete examples and Joe delivers two that crystallize the distinction. [1] — Joe Schmidt "Stuut went after accounts receivable — unglamorous, but with an established budget and a clear ROI story. Their pitch was pure math: AI col…" 13:40 Stuut, the AI accounts receivable company founded by Tarek and Ben, attacked a market nobody glamorizes — collections — but with a decisive advantage: an existing budget and demonstrable math showing AI could outperform human teams at the task. They went to mid-market buyers, showed the numbers, and stacked wins. Harvey took the opposite path into legal AI, a high-exposure market where buying the wrong product could expose a law firm to regulatory or ethical risk. Their playbook was to identify the specific handful of law firm lighthouse accounts whose endorsement would make the entire legal industry feel safe — and once those fell, proof traveled automatically. Andy McCall then adds Pylon, an AI-native customer support company in the a16z portfolio, as another land-grab example climbing the ACV ladder by directly replacing existing workflows with a faster, AI-powered alternative.
The US government's 2016–2019 electronic logging device mandate forced every trucking company to buy telematics hardware — overnight, an entire industry had both mandate and budget. Samsara was a new entrant competing against AT&T and Verizon, but the rising tide created space for a challenger with a better product.
Samsara was founded in 2015 with a vision of internet-connected sensors across value chains; Andy McCall joined in 2017 and helped build the sales organization through the ELD mandate tailwind.
The US government's electronic logging device mandate created a mandatory, time-boxed buying event across the entire trucking industry, giving Samsara a powerful tailwind as a new entrant.
