Threadless - the online artist community and design marketplace - is celebrating its 25th anniversary this year.

Founder and CEO Jake Nickell joins me for char dogs at Poochie’s (a favorite for hot dog fans north of the city) and talks about the company’s history, his leadership role, and why he celebrates the weird designs.

Discussed in this episode:

• Starting Threadless with $1000 and an idea
• Jake’s comfort in being a leader, and his leadership style
• Big mistakes (or, more euphemistically, learning opportunities) along the way
• Why Threadless’s success required marketing legend Seth Godin to be fired
• The value of remote/hybrid work
• Jake’s thoughts on AI, relative to the business of Threadless
• Growth plans for the next 5 years
• The impact of tariffs on business

I say it early on in the interview, but Jake is not your typical CEO. He’s literally a dude you’d want to eat a hot dog with … who just happens to run one of the coolest, most influential, online businesses of the past 25 years.

##

Car Con Carne sponsored by Easy Automation: easy-automation.net

Transform your living space with cutting-edge home automation. Experience seamless control over audio/video, lighting, climate, security, and more. Embrace the future of smart living – your home, your rules.

Get a quote by visiting easy-automation.net, or give Dan a call at 630.730.3728

##

Car Con Carne is also sponsored by Ninety Days in the 90s: A Rock N Roll Time Travel Story. It’s the ultimate novel about the ’90s and Chicago’s music scene, written by Andy Frye.

Join record store owner Darby on her trip back to 1990s Chicago as she jumps on the Grey Line to time travel back to her carefree twenties, soaking up all the pop culture and rock n roll nostalgia you could ever imagine. To learn more, go to 90daysinthe90s.com or pick it up on Amazon.com or wherever you buy books.

##

On Thursday, May 15, join me for a live recording of Car Con Carne at Legit Dogs and Ice in South Elgin – 322 S. Randall Road. Music from Aaron Williams Band, Karen Shook and Derision Cult. Comedy from Chris Bongat. Craft brewer Carson Souza from Obscurity Brewing.

Doors – 6:30 p.m.
Showtime – 8:30 pm.

See omnystudio.com/listener for privacy information.