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

Jul 11, 2025

Jonathan Cronstedt, an investor and advisor known for scaling Kajabi to $2B, shares his journey of success and failure. He discusses how to manufacture luck in business and the pitfalls of taking bad advice, revealing three key mistakes that cost him dearly. Cronstedt explains the pivotal moment of taking a pay cut that led to a billion-dollar valuation and addresses the balance between strategy and company culture. With humor and insights, he emphasizes the necessity of adaptability in the fast-evolving tech landscape.

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ANECDOTE

Bankruptcy Caused by Arrogance

Jonathan Cronstedt attributes his 2007 bankruptcy to arrogance, bad advice, and laziness.
He underestimated market collapse risks and spent too much time having fun instead of working hard.

ADVICE

Filter Advice for Success

Seek advice only from those who have succeeded by doing what you want to achieve.
Value wise counsel that stretches your reality and be wary of bad financial advice.

INSIGHT

Luck and Hard Work Combined

Luck plays a role in success, but increasing your exposure to opportunities helps leverage it.
Consistent hard work and caring deeply about customer success build strong brands and lasting results.

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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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