July 11, 2025

How to Manufacture Luck, Avoid Bad Advice, and Build a Business That Lasts: Billion-Dollar Lessons from a Serial Entrepreneur with Jonathan Cronstedt and Joe Polish

Show Notes

Jonathan “J Cron” Cronstedt reveals how he scaled Kajabi to $2B—and the failures that shaped him. A fast-paced dive into strategy, leadership, and staying human in a high-tech world.

Here’s a glance at what you’ll discover in this episode:

How to Manufacture Luck, Avoid Bad Advice, and Build a Business That Lasts: Billion-Dollar Lessons from a Serial Entrepreneur with Jonathan Cronstedt and Joe Polish
The Billion-Dollar Bullseye Formula: How Jonathan Cronstedt cracked the code on scaling businesses at warp speed—and why most entrepreneurs never make it past the first hurdle.
Bankruptcy, Arrogance, and Bad Advice: The three fatal mistakes that cost Jonathan everything in 2007—and how he turned rock bottom into a multi-billion-dollar comeback.
The Most Expensive Information in the World: Why taking the wrong advice—even for free—can cost you millions, and how to filter out the noise to find game-changing insights.
The Secret to Attracting Billion-Dollar Opportunities: How Jonathan’s decision to take a 50% pay cut at Kajabi led to a $2 billion valuation—and why most people would have missed the opportunity.
The Leadership Mistake That Almost Sank Kajabi: The painful lesson in over-promoting employees, breaking them in the process, and the hidden cost of putting culture over strategy.
How to Manufacture Luck on Demand: The one mindset shift that increases your surface area for luck—and how Jonathan used it to go from struggling to running a billion-dollar empire.
AI Is Coming for Your Business—Here’s How to Survive: The under-the-radar AI revolution Jonathan predicts will "rip a hole in society"—and why most entrepreneurs are completely unprepared for it.
The $670 Million Marketing Playbook: How one simple idea—giving customers a _________ —became the most profitable customer acquisition strategy in Kajabi’s history.
The Hidden Trap of Success: Why selling your company, retiring early, or exiting your business can be the most dangerous thing you ever do—and the existential crisis no one warns you about.
The Future of Business in an AI-Driven World: The industries that will be decimated, the rise of micro-enterprises, and why Jonathan believes craftsmanship and human connection will be more valuable than ever.

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Show Notes

From Bankruptcy to Billion-Dollar Boardrooms

J Cron’s journey from early-20s bankruptcy to Kajabi’s $2B valuation
Building Kajabi’s flywheel with a simple T-shirt and community recognition
The Bull’s-Eye Formula: how to scale fast and exit on your terms
Creating value through customer-first thinking and product simplicity

High-Stakes Hunches

Walking away from high-paying jobs for equity (and how it paid off)
Missteps like refusing to build features (e.g., multiple upsells) based on team sentiment
Lessons from hiring “shiny logo” executives who lacked true execution ability

Experience as a Compass

How early failure sharpened filters for advice and decision-making
Leveraging access to YPO and mentors to 10x insight and avoid repeat mistakes
Post-exit drift: why financial freedom without purpose can lead to identity crisis

Originals vs. Operators

Why most success content is written by “reporters,” not real builders
Filtering advice: is the person wealthy from what they teach or what they did?
Real vs. fake success stories: how to spot integrity in thought leadership

When Partnerships Click

The power of complementary skill sets with co-founder Kenny Rueter
Aligning product, marketing, and customer journey through shared purpose
Why friends who challenge you (like Joe Polish and Mike Koenigs) are business gold

Misalignment Magnified

Over-titling: how promoting too fast crushed people and morale
Family-style culture vs. performance-driven teams—and where it breaks
When protecting feelings prevents progress: costly leadership mistakes

Strategic Quits

Firing yourself post-exit to rediscover passion and direction
Walking away from comfort zones (and plumbing roll-ups) in search of alignment
Letting people go (or demoting them) when vision outgrows capability

Emotions in the C-Suite

How personal insecurities lead to bad decisions at scale
The invisible influence of imposter syndrome, peer pressure, and praise addiction
Bad advice, arrogance, and laziness: the “failure trifecta” that nearly ruined everything

Creativity at Scale