Dave Asprey—serial entrepreneur, bestselling author, and Bulletproof founder—went from making $6M by 26 to losing it all two years later. By 30, a health crash (testosterone lower than his mom’s, multiple diagnoses) pushed him to spend millions hacking his biology. He ultimately built Bulletproof to $140M in annual revenue—then was removed from the board in what he calls a calculated coup that cost him hundreds of millions. Now, as CEO of Upgrade Labs, he’s focused on making elite biohacking accessible.
This conversation goes well beyond cold plunges and butter coffee. Dave maps the decisions he wishes he’d made sooner: firing the $28M mistake, spotting narcissists quickly, and sorting win-win from win-lose people before they poison their business' culture. We explore how birth trauma shows up in leadership, why empathy drains while compassion sustains, and how to step out of the victim–perpetrator–savior triangle. He shares hiring guardrails (the “first-wiggle” rule, real reference checks, the 60-day policy) and therapeutic/energetic tools founders can use immediately.
If you’re building through chaos—navigating toxic team members, your own triggers, or both—you’ll leave with concrete ways to protect your company, your energy, and your judgment.
Key Takeaways and Topics
The $28M lesson: recognize the “first wiggle” and act right away
Four categories of people (win-win to win-lose) and who to hire
Red flags: instant “best friend” chemistry, envy tells, and trauma bonds
How to reference-check and background diligence
Empathy vs. compassion: boundaries that protect teams and CEOs
Business drama patterns and how leaders step out of them
Forgiveness as a nervous-system reset; going no-contact with manipulators
Energy as a leadership edge: willpower and decision quality
Daily levers: intermittent fasting and nighttime darkness
The Failure Factor Podcast was brought to you by Off The Field Coaching. Explore working with one of our coaches at http://offthefieldcoaching.com
Hosted by Megan Bruneau: therapist, executive coach, speaker, Forbes contributor, and host of The Failure Factor. For more info, visit https://meganbruneau.com
Follow Dave
Site: https://daveasprey.com/
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