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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Sara Blakely shares her remarkable journey from selling fax machines door-to-door to building the billion-dollar shapewear empire Spanx. This conversation reveals her unique approach to turning fear into courage, redefining failure as not trying rather than not succeeding, and the methodical way she transformed a simple idea into a global phenomenon. (02:00)
Sara Blakely is the founder and CEO of Spanx, the billion-dollar shapewear company she started with just $5,000 from her apartment. She revolutionized the undergarment industry by inventing footless pantyhose and built her empire through relentless cold-calling and grassroots marketing. Blakely is also a philanthropist who founded the Sara Blakely Foundation to empower women and recently created The Belly Art Project, donating all proceeds to maternal health causes.
James Altucher is an entrepreneur, author, and podcast host known for his unconventional lifestyle and business philosophy. He has started multiple companies and is recognized for his minimalist approach to living, owning only a few possessions while focusing on creativity and experiences over material accumulation.
Blakely's father taught her to celebrate failure by asking "what did you fail at this week?" at the dinner table. (03:38) This reframed failure from being about outcomes to being about not attempting something due to fear. For Blakely, the only real failure occurs when fear prevents action, not when attempts don't yield perfect results. This mindset shift allows for continuous experimentation and growth without the paralyzing fear of imperfection.
Blakely identifies three core elements that fuel courage: gratitude, embracing mortality, and connecting to a purpose beyond yourself. (07:29) Gratitude provides perspective on life's gifts, mortality awareness creates urgency and reduces petty fears, and serving a larger mission (like empowering women) gives strength to push through personal discomfort. This framework transforms fear into fuel for action.
Blakely credits her "fake commute" - driving around Atlanta for an hour before work - as crucial for creative breakthrough thinking. (25:03) She emphasizes that few people allocate dedicated time for unstructured thinking, yet this is where all creativity and innovation emerge. The key is finding activities that occupy your hands while freeing your mind to wander, similar to Einstein's insights during shaving.
When pitching or selling, Blakely consciously replaced phrases like "I think it's gonna be great" with "I know it will be great." (43:39) She learned that showing any doubt invites skepticism from others. This principle extends beyond sales to all forms of persuasion - from cold calling Neiman Marcus to convincing manufacturers to work with her. Confidence in delivery becomes a self-fulfilling prophecy.
During her door-to-door fax machine sales, Blakely found that being self-deprecating and showing vulnerability was more effective than trying to appear perfect. (18:25) She would acknowledge discomfort and be authentic about her situation, which created human connection and made people want to help. This approach works because it gives others permission to be kind and removes the defensive walls that typically arise during sales interactions.