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The Optimist's Playbook: Reinventing Yourself After the Exit with Joshua Litwack
What if success wasn’t the finish line — but the launchpad for who you’re meant to become?
In this episode, Joshua Litwack shares how he went from a lower-middle-class kid in Canada to building and selling a company — only to realize the real work began after the exit.
Josh breaks down how true entrepreneurs think differently: they see patterns no one else does, they reinvent instead of retire, and they measure success by how much meaning and community they create.
🎧 Tune in to discover what the post-exit journey really looks like — and why the secret to lasting success is learning to trust yourself, redefine greatness, and stay endlessly curious.
Key Topics:
-Reinventing success after selling a company
-Building resilience and trust in yourself
-The power of community and connection
-Goal setting as a foundation for growth
-The mindset of optimism and purpose-driven leadership
Quote From The Episode:
“The exit is perceived as this like ending point. But it's really just the beginning point of the next part of your life.”
- Joshua Litwack
Timestamp:
[01:39] Willpower, Innovation, and the Future of Work: How Visionaries Create Opportunity in a Changing World
[14:37] From Lower-Middle-Class Kid to Global Leader: The Hidden Compounding Power Behind Reinvention
[25:14] The Goal-Setting Blueprint That Changed My Life: How One Bold Decision Sparked a Lifetime of Reinvention
[35:22] The Obsession with Greatness: How One Founder Turned Risk, Reinvention, and Exit Lessons into His Life’s Best Work
[46:15] Beyond the Exit: The Real Lessons on Deals, Success, and Redefining Greatness in the Age of AI
[58:25] The Art of Storytelling: How the Most Positive Founder Turns Life Experience Into Magnetic Leadership
[1:09:47] Why the Best Founders Are Outcasts: The Goal System and Community That Fuel Relentless Success
[1:21:57] The One Trait That Separates Great Founders From the Rest
[1:27:04] Outro
Connect with - Joshua Litwack:
LinkedIn - linkedin.com/in/joshualitwack
Connect to Entrepreneurial-Excellence Podcast:
LinkedIn - https://www.linkedin.com/company/entrepreneurial-excellence-podcast
Youtube - http://www.youtube.com/@EntrepreneurialExcellencePod
TikTok - https://www.tiktok.com/@eepodcast24
Facebook - https://www.facebook.com/profile.php?id=61570329516959
Website - https://www.levy.company/entrepreneurial-excellence
View all episodes
By Adam SpectorWhat if success wasn’t the finish line — but the launchpad for who you’re meant to become?
In this episode, Joshua Litwack shares how he went from a lower-middle-class kid in Canada to building and selling a company — only to realize the real work began after the exit.
Josh breaks down how true entrepreneurs think differently: they see patterns no one else does, they reinvent instead of retire, and they measure success by how much meaning and community they create.
🎧 Tune in to discover what the post-exit journey really looks like — and why the secret to lasting success is learning to trust yourself, redefine greatness, and stay endlessly curious.
Key Topics:
-Reinventing success after selling a company
-Building resilience and trust in yourself
-The power of community and connection
-Goal setting as a foundation for growth
-The mindset of optimism and purpose-driven leadership
Quote From The Episode:
“The exit is perceived as this like ending point. But it's really just the beginning point of the next part of your life.”
- Joshua Litwack
Timestamp:
[01:39] Willpower, Innovation, and the Future of Work: How Visionaries Create Opportunity in a Changing World
[14:37] From Lower-Middle-Class Kid to Global Leader: The Hidden Compounding Power Behind Reinvention
[25:14] The Goal-Setting Blueprint That Changed My Life: How One Bold Decision Sparked a Lifetime of Reinvention
[35:22] The Obsession with Greatness: How One Founder Turned Risk, Reinvention, and Exit Lessons into His Life’s Best Work
[46:15] Beyond the Exit: The Real Lessons on Deals, Success, and Redefining Greatness in the Age of AI
[58:25] The Art of Storytelling: How the Most Positive Founder Turns Life Experience Into Magnetic Leadership
[1:09:47] Why the Best Founders Are Outcasts: The Goal System and Community That Fuel Relentless Success
[1:21:57] The One Trait That Separates Great Founders From the Rest
[1:27:04] Outro
Connect with - Joshua Litwack:
LinkedIn - linkedin.com/in/joshualitwack
Connect to Entrepreneurial-Excellence Podcast:
LinkedIn - https://www.linkedin.com/company/entrepreneurial-excellence-podcast
Youtube - http://www.youtube.com/@EntrepreneurialExcellencePod
TikTok - https://www.tiktok.com/@eepodcast24
Facebook - https://www.facebook.com/profile.php?id=61570329516959
Website - https://www.levy.company/entrepreneurial-excellence