Digital Transformation Episodes

Kris Rudeegraap—co-founder and co-CEO of Sendoso—joins me to talk about what happens when email stops working and you have to find another edge. Kris was a top seller who got 90% response rates in the early 2010s using mail merge. Then email sequencing tools flooded the market and response rates tanked. So he started sending handwritten notes, dog toys, and swag from the marketing closet—and booking more meetings than anyone else.

That curiosity—hearing a dog bark on a call and sending a dog toy—became the foundation of Sendoso, now the largest direct mail and gifting platform in the world. We cover the psychology of reciprocity, why the open rate of a FedEx box is 100%, and why dimensional mail is the channel that never stopped delivering.

The Kansas City ribs story is one you won't forget: a prospect broke a rib skiing, so the Sendoso team sent a rack of BBQ ribs to his office. He shared the story with his whole company, and they got the deal.
Kris's motto—"people buy from pe…

Juan García—co-founder of Tuio, an AI-native insurer based in Spain—joins me to talk about what happens when you rethink an industry from first principles. Juan started in engineering at Cisco, moved through strategy consulting, and then built Orange Insurance—where he saw just how broken the insurance industry really was.
The 25-55 customer segment is digitally native. They buy groceries online, manage finances on their phones, and don't want to call anyone. But legacy insurers weren't built for them—and worse, this segment was unprofitable because they're too informed. They use price comparison sites. They read Trustpilot. They know what they're buying.
So Juan and his co-founders built Tuio: a self-service, data-driven platform where customers actually buy insurance themselves. They went against the industry mantra—"insurance is not bought, it's sold"—and proved it could work.
The AI applications are fascinating. They can see which device you're browsing from and adjust risk pri…