Dustin Riechmann sits down with Ryan Levesque—7-time Inc. 5000 entrepreneur, 2x national bestselling author, and creator of the ASK Method®—to unpack how he’s built and exited multiple 8-figure companies. From overcoming burnout to mastering the art of digital leverage, Ryan shares contrarian strategies for entrepreneurs looking to scale sustainably. Learn why understanding your audience’s language is your secret weapon, how to design marketing that feels personal at scale, and why being “The Guy” (or “Gal”) behind the curtain might be the best move you’ll ever make.

Chapters:

• 00:00:00 - Morning Habits That Build Momentum
• 00:00:46 - Why This Episode Matters
• 00:01:00 - Enter: Ryan Levesque
• 00:01:51 - From Corporate to Entrepreneurial Breakthroughs
• 00:04:54 - The Scrabble Business That Sparked It All
• 00:07:19 - Early Lessons That Still Apply Today
• 00:11:03 - Leaving Texas: The Big Pivot to Vermont
• 00:20:01 - Inside the Regenerative Farm Life
• 00:20:22 - How We Live Off the Land
• 00:21:03 - Struggles, Surprises & Wins Along the Way
• 00:22:57 - Living Offline in an Online World
• 00:23:56 - Why Simplicity Creates Stronger Connections
• 00:25:52 - Meals, Mindfulness, and Raising Boys
• 00:28:29 - How to Create a Life People Remember
• 00:31:33 - The Real ROI: Time, Energy, and Peace
• 00:37:31 - Why I Write The Digital Contrarian

• ASK Method
• The Digital Contrarian Newsletter
• Website: ryanlevesque.net
• ASK Method®: askmethod.com
• Ryan on LinkedIn
• Dustin on LinkedIn
• 7 Figure Leap