Mike Fisher’s career has taken him from West Point and flying helicopters in the U.S. Army to leading technology teams at PayPal, serving as CTO of Etsy, and ultimately becoming CEO of MyFitnessPal.
In this episode, Mike joins Ilana to unpack the leadership lessons behind that unconventional journey. He shares what the military taught him about giving feedback, building trust, and learning from mistakes, and what he had to unlearn when he transitioned into the tech world.
Mike also explains why nearly every major opportunity in his career came through the “hidden market,” why professionals should focus on building skills rather than chasing titles, and what stepping into the CEO seat taught him about imposter syndrome and leading through uncertainty.
Plus, Mike shares what ultramarathons have taught him about pushing through dark moments, why great leaders need extraordinary willpower, and why he believes AI could ultimately create entirely new opportunities for entrepreneurs and professionals.
Chapters
00:00 Trailer & Introduction
02:58 The Hidden Market: Why Your Best Opportunities Aren’t on Job Boards
04:05 What West Point Taught Mike About Leadership
06:57 Why Great Teams Debrief Their Mistakes
08:12 Learning Leadership the Hard Way as an Army Pilot
10:19 The Helicopter Accident That Changed How Mike Led
14:27 Leaving the Military for a Career in Tech
16:01 The Boss Who Changed the Trajectory of Mike’s Career
19:13 What Mike Had to Unlearn From the Military
20:58 How to Get People to Follow You Without a Title
22:56 Why Great Leaders Tell Great Stories
25:58 The Hidden Job Market & Why Your Network Matters
28:18 Why Weak Ties Can Lead to Your Biggest Opportunities
28:46 How to Make Sure People Remember You
29:04 From Consultant to CTO of Etsy
31:04 The Power of Extreme Focus
35:30 Stop Chasing Titles, Build Skills Instead
37:04 How the Hidden Market Led Mike to MyFitnessPal
38:33 Becoming CEO: What Changes at the Top
41:30 Imposter Syndrome at the CEO Level
44:56 Find the Skill You Can Always Fall Back On
45:27 What Ultramarathons Teach You About Leadership
47:51 “We Do Hard Things”: Transforming Etsy
50:27 Finding Your Reserve Tank in the Darkest Moments
53:09 Why You Should Never Go Through Hard Things Alone
53:28 “You Signed Up for This”
55:06 How to Rise Above the Noise in Your Career
56:08 Why Rejection Should Be Treated Like an Experiment
57:55 Mike’s Take on AI, Jobs & the Future of Work
59:58 Could a One Person Billion Dollar Company Already Exist?
About Mike Fisher
Mike Fisher is the CEO of MyFitnessPal and a technology executive whose career spans the military, entrepreneurship, consulting, and some of the most recognized technology companies in the world.
A West Point graduate, Mike served as a U.S. Army aviation officer and helicopter pilot before transitioning into technology. His career has included leadership roles at PayPal, co-founding AKF Partners, and serving as CTO of Etsy, where he helped lead major technology and organizational transformations.
Outside of work, Mike is an ultramarathoner and writes about leadership, technology, and business through his Substack, Fish Food for Thought.
📲 Connect with Ilana:
Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy
LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/
Instagram ▶️ https://www.instagram.com/ilanagolanleap
Website ▶️ https://www.leapacademy.com/
Our TOPPODCAST Picks 
Stay Connected
