Bet On Yourself With Andy Olen

Episode 004: The AI Labor Tsunami Is Coming AI isn’t coming for jobs someday—it’s reshaping work right now. In this episode, Andy Olen breaks down why massive AI investment demands massive productivity gains, and why that creates real risk for corporate professionals, especially managers and directors. Drawing on insights from Davos and real-world examples across customer care, finance, and H...

Episode 003: Career Concentration Risk Career focus may sound smart, but it can be risky. In Episode 003 of Bet on Yourself, Andy Olen breaks down career concentration risk : the hidden danger of tying your income, identity, and future to one company, one industry, and one set of benefits. Through a real-world story and practical examples, Andy explains why putting all your career eggs in one bask...

Episode 002: Retired From Corporate America at 44 Andy Olen shares the personal story behind his decision to walk away from corporate America at age 44. He wasn't done working, but stopped outsourcing his time, energy, and financial future. What followed was the intentional leap into solopreneurship , building a business of one, reclaiming family time, and unlocking what Andy calls self-wealt...

Episode 001: The Great Detachment Why capable corporate leaders are staying, but emotionally checking out. In the inaugural episode of Bet On Yourself With Andy Olen, Andy explores The Great Detachment. In this workplace trend, talented professionals remain employed but feel disengaged, disconnected, and stripped of purpose. Andy shares a defining moment from his corporate career at Siemens Health...