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Built to Sell: How to Scale with Exit Intention w/ Ryan Estes of Kitcaster
What if your biggest success came from a total collapse? For Ryan Estes, that moment came when the pandemic wiped out his agency’s entire client list. Instead of folding, he doubled down on a side project—Kitcaster—and turned it into a thriving podcast booking service that would eventually be acquired. In this episode, Ryan opens up about his scrappy start, the mindset shift that fueled his growth, and why building a culture rooted in clarity (not chaos) made all the difference.
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Episode Resources
“The Origin of Consciousness in the Breakdown of the Bicameral Mind” by Julian Jaynes (https://a.co/d/8gKcq1r)
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Content is the Cheat Code: an Organic Growth Playbook w/ Steve Young of App Masters
After years of side hustles and self-doubt, Steve Young made one decision that changed everything. He began his entrepreneurial journey selling cassette tapes in grade school, but it wasn’t until he launched a niche podcast about apps that things finally clicked. In this episode, Steve shares how fear nearly held him back, how he landed his first client, and how he built a profitable agency without outside funding. It's a story about persistence, clarity, and the freedom that comes from betting on yourself.
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Episode Resources
“Extreme Ownership” by Jocko Willink and Leif Babin (https://a.co/d/e1Wvgug)
“Do Things That Don’t Scale” by Paul Graham (https://www.paulgraham.com/ds.html)
EO Fire by John Lee Dumas - A daily podcast featuring interviews with successful entrepreneurs, focused on their journeys, lessons learned, and tactical advice for aspiring founders. (https://www.eofire.com/podcast/)
Smart Passive Income by Pat Flynn - A podcast that explores how to build online businesses and create multiple streams of passive income, featuring strategies, case studies, and personal experiments from Pat Flynn and his guests. (https://www.smartpassiveincome.com/spi/)
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Founder Finances: Wealth, Life, & the Meaning of “Enough” w/ Chris Girbés of Five Oceans Advisors
When Chris Girbés left a steady job to start his own wealth practice, he wasn’t chasing scale. He was chasing meaning. In this episode, he shares what he’s learned from working with startup founders: the myth of the perfect exit, the danger of unclear goals, and the burnout that comes from tying your identity too closely to your business. Whether you're scaling or still scrappy, this conversation is packed with grounded insight on building a business while you build the life you actually want to live.
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Episode Resources
Registered Life Planner (RLP) - A certification focused on life-first financial planning. (https://www.kinderinstitute.com/rlp-designation/)
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