Episode 68 could very well be the most impactful episode we have recorded. For five and a half years, The COO Roundtable has highlighted the incredible work COOs perform daily across the RIA industry. As such, we’ve tended to focus on the tactical elements of the job: How do you effect change at your organization? How do you approach technology or process implementations? How do you tackle your never-ending to-do list?
In this episode, Matt focuses on the essential soft skills required for the COO role and interviews author Rachel Lebowitz about her research and new book, “Empowered COO – Eliminate Burnout, Resentment and Self Doubt as a Second-in Command.” After revealing his own past insecurities related to the role of COO, Matt asks Rachel to not only define the role of “Second-in-Command,” but to explain what about this unique position leads to burnout in so many cases (Rachel points out that the average COO engagement at a firm lasts about two and a half to five years). During this far-reaching conversation, Matt and Rachel discuss:
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.
iHeartOlympics: The Latest
Listen to the latest news from the 2026 Winter Olympics.
Milan Cortina Winter Olympics
The 2026 Winter Olympics in Milan Cortina are here and have everyone talking. iHeartPodcasts is buzzing with content in honor of the XXV Winter Olympics We’re bringing you episodes from a variety of iHeartPodcast shows to help you keep up with the action. Follow Milan Cortina Winter Olympics so you don’t miss any coverage of the 2026 Winter Olympics, and if you like what you hear, be sure to follow each Podcast in the feed for more great content from iHeartPodcasts.