FreightSimple’s Solution to Shipping's Biggest Headache with Natasha Ross

But First, A Note

What a time to be alive. It's been a while, so there's lots to catch you up on! Went on a revelatory trip to SXSW, which included recording not one but two shows, supporting a startup pitch winner, Xatoms, and eating a lot of BBQ. But that's for the next episode.

FreightSimple

Freight logistics quietly powers our economy - until it breaks. FreightSimple is a B2B logistics company that solves these shipping problems. To that end, we recorded this episode 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.

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