In this episode, Glen Ledwell the entrepreneur behind Mind Movies, Flight Club, and Speakeasy reveals how connection, timing, and lifestyle design shaped a multi-decade career. From scrappy beginnings to eight-figure wins, Glen breaks down the real secrets behind momentum, resilience, and building businesses you actually enjoy running.

In this conversation, Tyler sits down with entrepreneur and mastermind creator Glen Ledwell to unpack the lessons behind a 40-year entrepreneurial journey. Glen shares how he went from hustling football cards as a kid to launching the massive personal development brand Mind Movies, and eventually creating two of the industry’s most respected masterminds: Flight Club and Speakeasy.

Glen opens up about early failures, PayPal shutdowns, breakthrough timing, and why masterminds are the single most important growth tool for entrepreneurs today. He also dives into lifestyle design, law of attraction, business evolution, and why success means nothing if you aren’t enjoying your life along the way.

This is a masterclass in building businesses and a life that actually fit you.

Key Takeaways

• Entrepreneurship starts early even if you don’t realize it.
• Masterminds are essential for connection, accountability, and momentum.
• Curated communities beat big rooms quality > quantity.
• Timing matters Mind Movies exploded by riding the wave of The Secret.
• Online business was simpler, but success is still deeply accessible today.
• Lead costs rising + conversions falling = new solutions required.
• Lifestyle design is not a luxury it’s a non-negotiable for long-term success.
• Success isn’t worth it if you’re working nonstop and missing your life.