UNTUCKit: Chris Riccobono

How I Built This with Guy Raz

Guy Raz | Wondery

Business

4.8 • 31.1K Ratings

🗓️ 23 June 2025

⏱️ 79 minutes

🔗️ Recording | iTunes | RSS

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Summary

On a trip to Las Vegas, Chris Riccobono found himself wearing the same J.Crew shirt over and over; it was the only dress shirt he had that looked good untucked. All of his other button-downs were too long and looked sloppy. His buddies all said they had the same problem, so Chris decided to seize the opportunity and launch UNTUCKit with a friend. Keeping his day job as a GE salesman, he embarked on a crash course in how not to make a shirt. Thousands of defective button-downs later, UNTUCKit hit its stride, and the big fashion brands began to copy the untucked look. In 2020, UNTUCKit came within inches of a lucrative acquisition, then nearly went bankrupt, but today has grown into a thriving brand.

This episode was produced by J.C. Howard, with music by Ramtin Arablouei.

Edited by Neva Grant, with research help from Kerry Thompson.

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Transcript

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0:00.0	Wonderie Plus subscribers can listen to how I built this early and ad-free right now.
0:05.7	Join Wonderie Plus in the Wondery app or on Apple Podcasts.
0:10.4	AI might be the most important innovation ever.
0:13.5	It's storming every industry, with literally billions being invested.
0:17.2	So buckle up.
0:18.2	The problem is that AI needs the right data and a lot of speed and processing power.
0:22.9	So how do you compete without costs spiraling out of control?
0:26.6	Time to upgrade to the next generation of the cloud.
0:29.5	Oracle Cloud Infrastructure or OCI.
0:32.8	OCI is a single platform for your infrastructure, database and application development, with AI embedded across it all,
0:40.2	and Oracle's sovereign cloud helps you address your requirements for location, access, and data residency.
0:46.5	OCI provides blazing fast speeds for AI's demanding workloads, and in the cloud, when you pay by the minute, speed matters,
0:56.0	and of course nobody does data better than Oracle. If you want OCI to help you do more and spend less like Uber, the Premier
1:01.8	League and Oracle Red Bull Racing, take a free test drive at oracle.com slash Wondery. That's
1:07.9	oracle.com slash Wondery. Oracle.com slash Wondery.
1:13.5	If you've shopped online, chances are you bought from a business powered by Shopify.
1:19.0	And there's a reason so many businesses sell with it.
1:21.4	Because Shopify doesn't just make amazing buying experiences for customers.
1:25.6	They're also the experts in helping small businesses grow big.
1:31.1	Shopify is the commerce platform behind millions of businesses around the world and 10% of all
1:37.0	e-commerce in the U.S. From household names like Mattel and Jim Shark to brands just getting started.
1:44.1	Tackle all the important tasks in one place from inventory to payments to analytics and more.
	...

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