Freight logistics quietly powers our economy - until it breaks. FreightSimple is a B2B logistics company that solves for these shipping problems. To that end, this episode we recorded before the trade war started in earnest, so perhaps I need to have Natasha Ross, the cofounder, on weekly to follow the twists and turns in her business.

The business may seem dry - spoiler alert: that's the point - but it ain't. We covered the typical startup stuff (problem, solution, etc.), but Natasha was unusually candid about how she looks at her business. Her cofounder exited to Apple previously, which creates an interesting dynamic. I asked her whether she was shooting for an acquisition or how did she define success, and she answered thoughtfully.

I also felt the need in the monologue to talk about enshittification and where I think it will show up next.

In this episode we cover:

The absurdity of freight logistics: "You'd email or call around, hoping someone replies before your shipment misses the truck."
The startup reality check: "Initially, the market was allergic to tech; now they can't get enough."
Natasha’s best lesson: "Solve the boring stuff—complexity hides opportunity."
How to earn an industry's trust and Natasha's advice for entrepreneurs.

00:02:00 – Interview begins: Natasha Ross from FreightSimple

00:08:30 – Life before FreightSimple: struggles with manual logistics

00:14:52 – Empowering businesses to simplify freight decisions

00:22:37 – Why solving logistics problems is uniquely rewarding

00:29:34 – Behind-the-scenes: automating freight bookings

00:37:08 – Eliminating costly mistakes in shipping logistics

00:46:12 – Overcoming startup challenges in resistant industries

00:54:26 – Gaining industry trust: lessons from FreightSimple’s growth

01:02:10 – Natasha’s advice for entrepreneurs navigating complex industries

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