Live Bold. Think Different.
From sailing six yachts to writing bestsellers and hosting powerful podcasts, Kyle Corbett blends motivation, humor, and proven entrepreneurship into lessons that inspire lasting change.
More Than Ordinary
Kyle Corbett is not defined by one title. He’s an entrepreneur, author, podcaster, and comedian, combining success, humor, and lifestyle freedom to teach others how to live boldly and achieve extraordinary goals.
Proven Success
Built a sailing empire from $6,500, scaling into a six-yacht business grossing $650k annually.
Creative Voice
From stand-up stages to podcasts, Kyle brings humor that inspires learning without boredom.
Global Perspective
Experiences across 20 countries shape unique insights on growth, culture, and motivation.
Life Lessons
Author of Hindsight 2020, Kyle shares real strategies to help others turn challenges into victories.
Discover the Power of Bold Choices
Want to take control of your future? Kyle Corbett’s book Hindsight 2020 reveals what it truly takes to be your own boss. Packed with personal stories, lessons, and practical steps, this inspiring guide shows how bold choices can create freedom, resilience, and real success. Ready to learn, grow, and design life on your terms? Start with Hindsight 2020.
The Story Behind Kyle
It began with almost nothing. Just $6,500, a restless mind, and a vision too big to ignore.
From that spark, a fleet of yachts rose on the San Diego coast. Six ships. Six symbols of what’s possible when risk meets relentless drive.
But the story doesn’t stop on the water. On stage, Kyle turns raw truth into laughter. In books, he traps wisdom inside words. Through podcasts, his voice crosses borders, stirring minds he’s never met.
The journey stretches across twenty countries, countless cultures, and lessons carved by trial and fire. Each chapter sharper. Each insight deeper.
Armed with social psychology, seasoned by life itself, Kyle teaches not from theory — but from scars, victories, and lived moments.
This isn’t just his story. It’s an open challenge. To dream louder. To think differently. To live boldly — before time slips away.
Share These Inspirational Words With A Loved One
Offerings — entrepreneurship, creativity, lifestyle
From scaling businesses and coaching to books, comedy, podcasts, and curated getaways — select an experience to learn more.
Sailing Adventures
Luxury yacht experiences with San Diego Sailing Tours.
Author & Books
Hindsight 2020 and inspiring publications.
Consultation & Coaching
Entrepreneurship, mindset, and lifestyle freedom guidance.
Stand-up Comedy
Laughter with a purpose — humor that motivates.
Podcasts & Media
Impulse Upgrade — stories, mindset, growth.
Vacation Rentals
Big Bear retreat for peace, nature, and reset.
Real People. Real Impact.
From sailing tours to stand-up stages, Kyle Corbett’s impact speaks through the voices of real people who experienced his humor, wisdom, and entrepreneurial guidance firsthand.