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What does it really take to lead a modern marketing organization without burning out or losing yourself? In this episode of Lead Human, Jack Myers and Tim Spengler sit down with Lauren Weinberg – former CMO of Peloton, global CMO of Square, and longtime marketing leader – to talk about grit, energy, and choosing work that actually fills you up, not empties you out. Lauren shares how she thinks about the fork in the road between entrepreneurship and big-company leadership, why relationships are everything inside large organizations, and how she tries to lead with listening, not ego. She unpacks her idea of “energy vampires” at work and in life, how COVID forced her to reset her priorities as a mom of two teenage boys, and why she now sets unapologetic boundaries around the moments she refuses to miss. Lauren also explains why she avoids the old “brand vs performance” fight and instead talks about creating and capturing demand, including how she partners with CFOs to get on the same page about timelines, metrics, and risk. From leading Peloton’s marketing through a turnaround, to learning from Jack Dorsey’s blend of confidence and humility, to her own AI learning journey, Lauren offers a grounded, practical playbook for anyone trying to grow a career, a team, and a life at the same time. 00:00 Olympics, Super Bowl & America at 250 – cold open 04:09 “Greetings, humans” – Lead Human intro 05:05 Who is Lauren Weinberg? Bio & career snapshot 07:07 Grounding question – “Who are you as a human?” 08:32 Entrepreneur vs big company – which path fits you? 11:56 Energy vampires, burnout & protecting your own energy 15:15 Leading teams through transformation at Square & Peloton 18:12 Peloton turnaround – mission, purpose & crisis leadership 20:11 Leading by listening, open floor plans & being in the middle of the team 21:21 What Lauren learned from working with Jack Dorsey 23:03 Parenting, COVID reset & unapologetic boundaries at work 28:38 Brand vs performance: create demand, then capture demand 33:35 Lauren’s AI learning journey & how to get started 37:01 Bringing AI learning into your team and organization 38:29 Recap – energy, family, discernment & measurement 41:59 Choosing work that fills you up & closing thoughts