I Sold My Watch Company For $100M and Retired at 27 | Jake Kassan

Video Description

What You’ll Learn in This Episode In this episode, Jake Kassan, co-founder of Movement Watches, reveals the emotional rollercoaster of building and selling a business for $100M—and what came after. He shares: ✅ How he scaled Movement from a $5,000 credit card to a $100M exit ✅ The loneliness and identity crisis he faced after selling ✅ Why chasing money alone didn’t fulfill him ✅ The creative spark that led him to YouTube ✅ His advice for founders struggling with burnout or searching for meaning If you’re a founder chasing big goals, feeling stuck, or wondering what comes next—this episode is packed with raw, honest insights that rarely get shared. 📩 How We Can Help You Scale Your Business Faster 🔥 Want to learn directly from 7, 8 & 9-figure founders inside Foundr+? Start your $1 trial today → http://www.foundr.com/startdollartrial 💡 Prefer a custom roadmap and 1-on-1 coaching? → Starting from scratch? Apply here → https://foundr.com/pages/coaching-start-application → Already have a store? Apply here → https://foundr.com/pages/coaching-growth-application 🔗 Connect With Nathan Chan 📸 Instagram → https://www.instagram.com/nathanchan 💼 LinkedIn → https://www.linkedin.com/in/nathanhchan/ 🔗 Connect With Jake Kassan 📸 Instagram → https://www.instagram.com/jakekassan 🎥 YouTube → https://www.youtube.com/@JakeKassan1 00:00 - Intro to Jake Kassan 00:53 - Welcome to The Foundr Podcast with Nathan Chan 01:07 - Starting MVMT at Age 21 01:59 - The Loss of Identity After Selling 03:12 - The Hidden Pain of a Big Exit 03:57 - How MVMT Started with Crowdfunding 04:56 - Building a Brand That Resonated with Gen Y 05:21 - Scaling From $1M to $75M Before Exit 05:49 - No Investors, Just Scrappy Execution 06:06 - Did Jake Always Want to Sell? 06:36 - Why Movado Acquired MVMT 07:17 - The $100M Deal: How It Went Down 08:03 - Waking Up With Millions in the Bank 08:44 - Still Stuck in the Routine After the Exit 09:07 - Post-Sale Emptiness Starts to Sink In 10:01 - Kicking the Goalposts Down the Road 10:19 - Realizing More Money Won’t Fix Unhappiness 10:37 - Leaving MVMT & Looking for What's Next 11:13 - Why Starting Another Brand Didn’t Excite Him 12:26 - Trying to Fill the Void with Travel, Games, Weed 13:15 - Loneliness After "Success" 14:03 - Why Investing Didn't Give the Same Fulfillment 15:13 - Building Something From Scratch Was the Real Joy 15:56 - No Longer Motivated By Money Alone 17:03 - Finding Fulfillment After a Big Exit 17:58 - Creation vs Operations: What Truly Drives Jake 19:06 - Seeing MVMT in the Wild Was the Best Feeling 19:28 - Why He Didn’t Start Another Brand 20:12 - Being a People-Pleaser Made Management Hard 21:15 - Searching for Passion Through Hobbies 22:03 - The Joy Was Gone, and He Knew It 23:05 - Most Founders Don’t Know What Else to Do After Exit 24:36 - The Inner Conflict of Not Wanting to Keep Scaling 25:13 - “Easy for You to Say” — Jake Responds 26:26 - Money as a Means, Not an End 27:15 - More Money, More Alienation 27:34 - True Friends & Outgrowing Conversations 28:32 - Investing in Yourself Outside Business 29:35 - Think About Life Beyond the Business Early 30:12 - Health, Balance & Self-Awareness Matter 31:05 - Selling Doesn’t Automatically Mean Fulfillment 32:20 - Moving the Goalposts Kills the Joy 33:18 - The Trap of Chasing Bigger Exits 34:06 - Redefining What Success Looks Like 35:14 - Why Personal Growth Meant More Than the Exit 36:00 - How Jake Found a New Passion Through Video Creation 37:31 - Treating YouTube Like a Business 38:21 - Why Creative Work Is His New Form of Entrepreneurship 39:05 - Making Money on YouTube Was Never the Goal 40:01 - Rediscovering The Joy of Creation 41:13 - Entrepreneurship = Modern Day Art 41:34 - The Power of Vulnerability in Content 42:33 - What His YouTube Channel Is Really About 42:56 - Entrepreneurship is Art—Jake’s Take 43:21 - The Freedom (and Loneliness) of Not Needing to Work 44:13 - When You Have No Responsibilities & All the Time 44:55 - The Mental Toll of "Doing Nothing" 45:35 - Creating Routine Again After 5 Years Off 46:13 - The Dark Side of Entrepreneurship No One Talks About 🎯 Follow Foundr for More Business Growth Strategies 📺 YouTube → http://bit.ly/2uyvzdt 🌍 Website → http://www.foundr.com 📸 Instagram → https://www.instagram.com/foundr/ 📘 Facebook → http://www.facebook.com/foundr 🐦 Twitter → http://www.twitter.com/foundr 💼 LinkedIn → https://www.linkedin.com/company/foundr/ 🎙️ Podcast → http://www.foundr.com/podcast