#182 - Round 2 - Phil Gaimon, Un-Professional Cyclist from Worst Retirement Ever

Pro cyclist-turned-creator Phil Gaimon returns for Round 2 to pull back the curtain further on “the worst retirement ever.” We get the real behind-the-scenes of putting on Phil’s Cookie Fondo and Whiskey Tango—last-minute espresso truck rescues, county crews dynamiting boulders, volunteer scrambles, and the relentless safety calculus of hosting thousands of riders. Phil talks candidly about why he hates the word “influencer,” setting lanes for what he will (and won’t) weigh in on, and how his anti-doping stance and cycling advocacy shaped his voice.We dig into the creator economy without the gloss: YouTube vs. sponsorships, resisting rage-bait thumbnails, learning editing late, and the quiet reality that many “pros” and influencers aren’t paid like you think. Phil also reflects on aging as an athlete, redefining goals when PRs stop coming, and why professionalism doesn’t have to depend on a result sheet.SQ Socks: ⁠https://stupidquestions.show/pages/sq-merch⁠ SQ Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup⁠ Phil’s YT: https://www.youtube.com/@worstretirementeverPhil’s IG: https://www.instagram.com/philgaimon/Phil’s Cookie Fondo: https://www.philsfondo.com/