Description:
In this episode of The Builders, Matt sits down with legendary marketer and webinar strategist Jason Fladlien to discuss the mindset, methods, and AI-fueled magic behind his latest venture — Project Mona Lisa.
From waiting years to adopt AI until it finally delivered real advantage, to architecting offers so good they sell themselves, Jason reveals the first principles behind how he builds. You’ll hear how he’s combining decades of proprietary knowledge with the power of AI to make webinar creation faster, smarter, and more accessible than ever.
Whether you're building digital products, launching a SaaS, or leveling up your marketing game — this episode is a blueprint for playing to win.
What You’ll Learn in This Episode:
- Why Jason waited years to touch AI — and what finally changed his mind
- The origin story of Project Mona Lisa and how it uses AI + proprietary knowledge to deliver advantage
- How Jason builds for demand first before creating supply
- The mindset of only playing games you can win — and how that shapes every decision
- Why A- execution at scale beats A+ perfection when building software
- Real strategies to seed virality, test with live users, and generate proof before a full launch
- The deeper why behind Jason’s drive — and how adversity turned into fuel
Jason Fladlien
Jason Fladlien is known as the quarter billion dollar webinar man. His pitch webinars have set records in the information, coaching, affiliate, and software space. He draws upon his eclectic background for inspiration, from being a Hare Krsna monk and a rapper born and raised in the small town of Muscatine, Iowa.
He has risen to the top of several industries including information products, software, coaching, consulting, speaking and eCommerce.
Jason is often called in by 7, 8 and even 9-figure companies to help them with their marketing. To date, he is the only marketer Zoom specifically brought in to help its own users with webinars.
These days Jason spends much of his focus on Strategic Positioning – whereas other marketers try to figure out the best recipes and how to be the best chef, Jason figures out how to get the best ingredients in place first. The best victories in business are won by knowing where and when to play.
THE MEAT OF IT!
1. Jason’s Core Philosophy: Only Play Games You Can Win
- Why he waits to engage until the odds are in his favor
- The mindset that drives his product strategy and long-term success
2. From Monk to Marketing Legend
- Jason’s early life and turning adversity into alchemy
- The origin of his drive and how it shaped his career path
3. Building a Quarter Billion Dollar Webinar Empire
- His journey into affiliate marketing and the evolution into webinar mastery
- Why teaching is the best form of learning
4. The Birth of Project Mona Lisa
- What sparked Jason’s interest in AI after years of skepticism
- How a mastermind demo shifted everything
- Fusing proprietary knowledge with AI for a competitive edge
5. Building AI Products for Real-World Use
- The importance of creating demand before building supply
- The strategy behind teasing, testing, and validating with real users
- A- grade output at scale vs. A+ artisanal content
6. Marketing That Builds Itself
- Viral software loops, affiliate seeding, and platform-based exposure
- Leveraging personal brand and social proof for long-term lift
7. What’s Next for Jason
- Partnering with platforms like Zoom and beyond
- Evolving strategy in the age of AI
- Thoughts on branding, visibility, and always adapting
Click to See Episode Chapters and Timestamp
| Timestamp | Summary |
| 0:00 | Jason Flatland's Approach to Demand-Driven Product Development |
| 5:59 | From Rapping Monk to Marketing Enthusiast |
| 7:37 | Mastering Webinars: From Affiliate Marketing to Industry Leader |
| 11:06 | Cultural Differences in Motivation and the Love for Learning |
| 12:13 | A Childhood Injury and a Father's Unexpected Reaction |
| 13:15 | Turning Adversity Into Alchemy for Personal Growth |
| 14:44 | Project Mona Lisa: The Godfather of Webinars |
| 16:03 | Crafting Irresistible Offers That Require No Trust |
| 18:28 | Challenges and Opportunities in Adopting AI for Mass Markets |
| 23:42 | High-Profile Marketing Successes and Record-Breaking Launches |
| 26:15 | Leveraging AI and Proprietary Knowledge for Competitive Advantage |
| 30:15 | Innovative AI-Driven Webinar Tool Sparks Market Excitement |
| 37:25 | Innovative Marketing Strategies for Software Promotion |
| 40:58 | Building Personal Brands and Exploring AI Ventures |
Check out these related Episodes:
- Episode 225: Danielle Hutchinson – Build Your Brand Identity with an Angel Writer (Ghostwriter)
- Episode 216: Andreas Pettersson – Corporate Exec to Scrappy Builder: Master the Mindset of Growth & Action
- Episode 210: Mallory Glessner – Building a Content Machine: Scaling Social Media with Strategy & Creativity
