All Episodes

October 20, 2025 54 mins

"In your 20s, take risks. You have time to change your plan or celebrate."

 

Today on the show I sit down IN PERSON with former employee of my Evan Callaghan and catch up on life's wild pivots—all the way from the trenches of fraud analysis to the world of data engineering. Evan shares the hilarious and often chaotic story of moving to L.A. on an impulse, only to find himself in a completely new industry after his rock star dreams hit a snag. They discuss the value of taking big risks in your 20s, whether it's moving across the country for an elusive music career or enduring soul-crushing early morning gigs to learn a craft. From the discipline learned as a serious ski racer to the hustle of selling solar panels door-to-door, every adventure—and misstep—has contributed to his current path.

 

Evan's journey highlights a powerful transition from creative pursuit to a focused tech career. After realizing his passion for music production had a technical, analytical core, he switched gears, diving into a demanding coding bootcamp. He shares funny anecdotes about his failed music promotion event and the shocking revelation that nobody cares if your data is "PhD-level" if it's dirty! Listen in to hear how two friends—and former colleagues—found success by continually seeking growth, even if it meant getting "slapped by the universe" a few times along the way.  Find Evan here: https://www.linkedin.com/in/evancallaghan1994/

Mark as Played

Advertise With Us

Popular Podcasts

Stuff You Should Know
The Joe Rogan Experience

The Joe Rogan Experience

The official podcast of comedian Joe Rogan.

Two Guys, Five Rings: Matt, Bowen & The Olympics

Two Guys, Five Rings: Matt, Bowen & The Olympics

Two Guys (Bowen Yang and Matt Rogers). Five Rings (you know, from the Olympics logo). One essential podcast for the 2026 Milan-Cortina Winter Olympics. Bowen Yang (SNL, Wicked) and Matt Rogers (Palm Royale, No Good Deed) of Las Culturistas are back for a second season of Two Guys, Five Rings, a collaboration with NBC Sports and iHeartRadio. In this 15-episode event, Bowen and Matt discuss the top storylines, obsess over Italian culture, and find out what really goes on in the Olympic Village.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.