Mike and Paul’s Road Trip

Mike and Paul’s Road Trip

Author: Paul Ollinger March 5, 2024 Duration: 1:46:09
This episode is highlights of a conversation between Paul and Mike Carano, long-time friend and Crazy Money editor. It was recorded on a road trip between San Francisco where Paul had just performed at Cobb’s Comedy Club and San Luis Obispo where he was heading to perform in the SLO Fest Comedy Festival. Among other things, Paul and Mike discuss:

Memories of commuting from SF to Yahoo! in Sunnyvale

Why it’s hard to admit what we want in life

The history of Crazy Money

The possible new names for Crazy Money

Life in general

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Topics addressed on Crazy Money include: Philosophy, Happiness, Contentment, Meaning, dreams, purpose, Success, Society, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, Mid-Life Crisis, Business, Work, Careers, Authors, Books, Consumerism, Values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, wealth, wealth management.
If you haven’t found what you’re looking for in the words above, you’re probably not going to find them down here. Seriously, all the important stuff is up yonder.

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Paul Ollinger has worn a few different hats-stand-up comedian, tech executive, and now, the curious host of Reasonably Happy with Paul Ollinger. This isn't a lecture series or a dry self-help guide. Instead, it feels more like pulling up a chair for a series of genuinely engaging talks that wander into the places where our daily lives, careers, and inner worlds collide. The conversations, which feature authors, thinkers, and various creatives, are refreshingly candid. They dig into the practical and philosophical questions about what it actually means to build a life that feels both successful and satisfying. You'll find that each episode of this podcast approaches big themes-money, purpose, and the pursuit of contentment-with a blend of wit and thoughtful depth. The underlying idea isn't about finding a perfect, Instagram-ready version of happiness, but something more grounded and attainable. It's for anyone who's ever wondered if there's a smarter, more meaningful way to navigate the pressures of business and culture without losing sight of what matters. Tuning in, you get the sense that Paul is figuring it out alongside his guests, making the insights feel earned and relatable. The result is a consistently interesting exploration of how we can all aim for a life that feels reasonably, and authentically, well-lived.
Author: Language: English Episodes: 100

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