The Thing We Never Talk About

With investing tools cheaper & more accessible than ever, why would anyone still pay an advisor to manage their investments? In this solo episode, Tim breaks down how the biggest benefit of investment management isn’t better stock picks or secret knowledge, but help with follow-through, emotional decision-making, and actually doing the things you already know you should be doing. The episode closes with practical guidance on how to decide whether managing your own investments or delegating that responsibility makes the most sense for you. One Key Takeaway: Paying for investment management isn’t about access to information or tools—it’s about whether having support helps you make better decisions and stick with them over time.
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Ryan Isaac is an education fundraiser & longtime baseball insider who spent more than a decade working in professional baseball. In this episode, Ryan shares how he broke into the industry, what it was like navigating the uncertainty & mobility of baseball careers, and why becoming a parent ultimately reshaped his priorities. He reflects on the identity shift that comes with leaving a dream job and finding new ways to stay connected to the work you love. The conversation also explores how Ryan rediscovered his voice through writing and launched his baseball newsletter, Warning Track Power, as a creative outlet beyond his day job.
Ryan's question for me: What was the biggest obstacle you faced during your career transition? 
Key takeaways:
Ryan shares his early career ambitions as a writer and journalist, including working at Wine Spectator in New York City while nurturing a long-standing passion for baseball. 
He describes leaving journalism to pursue a career in professional baseball during the early “Moneyball era,” including moving to San Diego without a job lined up to put himself closer to opportunity. 
Ryan recounts how a chance phone call led to his first full-time role with the San Diego Padres, marking his official entry into Major League Baseball operations. 
After leaving baseball, Ryan transitioned into fundraising for an independent school, gradually building experience through expanded responsibilities during the early COVID period. 
During the pandemic, Ryan reignited his creative outlet by writing about baseball, leading to the launch of his newsletter Warning Track Power as a personal and intellectual release.
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Ryan's newsletter Warning Track Power
Warning Track Power's Substack page

Every year, financial “experts” roll out confident predictions about what the markets and economy will do next — and almost every year, they’re wrong. In this solo episode, Tim explains why financial forecasts are so appealing, why they’re fundamentally unreliable, and how chasing certainty can actually hurt your long-term financial health. Instead of guessing the future, he lays out a simple, durable framework for building stability, flexibility, and peace of mind in an unpredictable world. One Key Takeaway: You don’t need to predict the future to build financial security — simple habits, long-term thinking, and preparation for uncertainty matter far more than any market forecast.
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Financial Forecasts Are Bullsh!t
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Drumming instructor Todd Trainer joins Tim to talk about how an unexpected job loss pushed him into building a new career around teaching. He shares the story of growing his student base from DIY flyers to a full teaching practice, and why helping beginners find confidence & creativity has become some of the most meaningful work of his life. Todd also talks about adapting his teaching style for different learners and the philosophy that guides his approach to drumming instruction.
Key Takeaways:
Todd Trainer—best known as the drummer of Shellac—shares how losing a long-time job pushed him toward drumming instruction as a new career path. 
He started his teaching business in DIY fashion, putting up flyers & offering mobile lessons at his students' homes or rehearsal spaces. Eventually, Todd (and his wife, a designer) built a website that features scheduling tools & a payment system, which have been essential to the business’s success.
His teaching philosophy emphasizes creativity, individuality, and imagination—encouraging students to develop their own unique style rather than chasing technical perfection. 
Todd finds deep fulfillment in teaching beginners, especially children, and describes how helping them discover their first drumbeat is one of the most rewarding parts of instruction. 
Teaching has become emotionally meaningful for Todd: the value exchanged between student and instructor goes far beyond the time they spend together.
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Todd Trainer Drumming Instruction
Twin Cities Drum Collective
Shellac of North America

Holiday spending can creep up fast — and the new year is the perfect time to reset. In this episode, Tim introduces the 4-Week Financial Detox, a simple step-by-step process designed to help you pause discretionary spending, reset your baseline expenses, eliminate costly subscription “leaks,” and refocus your money on what truly matters. Whether you’re rebuilding after the holidays or just ready to use your money more intentionally, this short reset can help you start the year with more clarity, control, and confidence in your financial life. One Key Takeaway: Small, temporary changes to your spending habits can create lasting improvements in financial health — especially when you focus your money on what genuinely enriches your life.

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4-Week Financial Detox
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