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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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Betting the Farm: Navigating the Risks & Rewards of Family Business w/ Tiffany Bailey of Bayside Sod
When Tiffany Bailey stepped into her family’s sod farming business, she didn’t see herself as an entrepreneur, just someone grinding to get the work done. But nearly two decades later, she’s redefined the company, the culture, and herself as a leader. In this episode, Tiffany shares the raw truth about running and growing a business with family: the trust, the tension, and the tough calls. Hear how she navigated succession, scaled the business, embraced B2C, and built a culture rooted in clarity and care. This is a masterclass in leadership, learning, and legacy.
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Episode Resources
Check out what Tiffany is building at Bayside Sod (https://baysidesod.com)
Read more about the Full Focus Planner (https://fullfocusstore.com)
Learn more about the Culture Index (https://www.cultureindex.com)
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The Truth About Early-Stage Investing w/ Kelly Iannone
In today’s episode I talk with Kelly Iannone, an experienced full-time investor who’s built a diverse portfolio across real estate, public stocks, and most recently, early-stage startups. She shares why one of the biggest misconceptions about investing is that you have to do it all yourself, how to spot a founder worth betting on, and why trusting the right people is the real key to hedging risk and achieving 10x returns. If you’ve ever wondered how to get involved in startup investing—or how to avoid the biggest mistakes—this episode is for you.
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Episode Resources
Keep up with Kelly (https://www.linkedin.com/in/kelly-iannone-waypointcip)
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