In this deeply personal conversation, Ryan reveals how he made major life pivots, developed the courage to take action despite fear, and why he believes the future belongs to entrepreneurs who focus on authentic connection over automation. If you've ever felt trapped by conventional business wisdom or wondered how to build a business that truly serves your vision of a well-lived life, this episode offers both practical wisdom and inspiring perspective.
Show Notes
[00:00:52] - The Unexpected Connection
Phil reveals how Ryan's Ask Method became the foundation for his patient acquisition system
This system eventually spawned an entire business serving other practice owners
Ryan shares how finding solutions to your own problems can become opportunities to serve others
[00:06:52] - Ryan's Entrepreneurial Journey
Left his financial firm job during the 2008 crisis with nothing but a suitcase
Built his first business teaching people how to make Scrabble tile jewelry
Expanded into multiple markets including Orchid Care and Memory Improvement
Developed the Ask Method, a methodology for understanding market segments
Helped companies achieve nine-figure exits using his methods
Sold his own software company, Bucket.io, in 2024
[00:14:02] - Overcoming Fear and Taking Action
Ryan explains why people hesitate to give up "good" to go after "great"
Shares his "ramen noodle and bologna sandwich" season of life
Reveals his neuroscience-based approach to overcoming fear
Advocates breaking big goals into impossibly small steps
[00:22:27] - The $500 Growth Strategy
How Ryan grew his business from zero to $25,000/month in 18 months
The power of asking "How can I grow my income by $500 more?" each month
Why small, manageable goals lead to exponential results
[00:25:56] - The Farm Life Transition
Ryan's realization that he was burning out in his business
Taking time off to work on a Vermont farm and discovering a new calling
Selling his house in 14 days with no plan except a vision
Building a sustainable farm life from scratch with no prior experience
[00:30:47] - Living with Purpose and Courage
Ryan's perspective on raising children and making the most of limited time
His life mantra: "Be curious, ask questions, seek truth"
The importance of deep conviction loosely held
Defining courage as taking action despite fear
[00:38:13] - The Return to Real Connection
Ryan's realization that he hated his business and the "photocopy" voice it had created
His decision to personally write all communications that bear his name
The Digital Contrarian newsletter and focusing on "unscalable" authentic connection
Why the best things in life don't scale
[00:46:12] - Creating a Business Around Life's Non-Negotiables
Setting clear boundaries like no meetings before noon or on Fridays
Making family dinner and children's events absolute priorities
Understanding that every business has an optimum size
Building a business that supports what's meaningful rather than the reverse
Key Quotes
"I believe there's no better bet than betting on yourself. There's no better investment that you can make than investing in yourself." - Ryan Levesque
"What is one step I can take toward that vision I've set for myself that is so small, it's literally impossible for me to fail?" - Ryan Levesque
"Courage is not about not being afraid. There are a lot of things that I'm afraid of. But what I've learned is that courage is what's required to take action in spite of that fear." - Ryan Levesque
"I believe the best things in life don't scale. And oftentimes when I'm asked, how do you make the time to write something every single week yourself? Well, I take great solace in that because I know that's not something that my competition is willing to do." - Ryan Levesque
"As entrepreneurs, we have the opportunity to build businesses that support what's most meaningful to us. And it should not be the other way around." - Ryan Levesque
Resources Mentioned
The Digital Contrarian - Ryan's weekly newsletter on Substack
Ask. Book - Ryan's methodology for market research and segmentation
ScoreApp - The assessment software company that acquired Ryan's company Bucket
Thank You
A huge thank you to Ryan for sharing his journey and wisdom with our community. And thank you to everyone who joined us live or is catching up with the recording,
Please Share
If you enjoyed this conversation, please consider sharing it with someone who might benefit from hearing Ryan's perspective on building a business that truly supports what matters most in life.
P.S. You can read all previous editions of the newsletter here, and you can upgrade your subscription here.
What’s next?
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