The Thing We Never Talk About

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 drea...

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, dur...

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 fo...

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 t...

In this wide-ranging & deeply reflective conversation, guitarist Randy Randall (No Age, Hyphenate with Randy Randall) talks about the shifting economics of indie music, redefining success as he became a parent, and building a freelance career in marketing almost by accident. From his early days immersed in the DIY community to learning resilience in the gig economy, Randy shares an honest, ung...

In this episode, Tim explains why cash flow is the foundation of every financial plan — and introduces a simple technique to make saving money easier and more consistent. By identifying your “invisible number,” the small amount you can save automatically without ever noticing, you can improve your cash flow, build long-term security, and reduce friction in your financial life. Tim breaks down how...

Film and video editor Max Goldblatt joins Tim to talk about building a creative career across indie films, digital content, and nearly a decade of touring. He shares how early exposure to editing shaped his path, how short-film work opened doors to feature projects, and what it takes to balance passion, stability, and financial responsibility in an unpredictable industry. Max also reflects on navi...

As the year winds down, Tim shares five practical steps you can take right now to lower next year’s tax bill. From maximizing retirement contributions to understanding energy-efficiency credits, this episode focuses on simple, actionable strategies for creative professionals and self-employed listeners. Tim breaks down how tax-deferred accounts, health savings accounts, and even small investment d...

In this episode, Tim talks with writer, drummer, and content specialist John Dugan about creative work, shifting career priorities, raising kids in a music-rich environment, and how financial needs and perspectives evolve over time. John reflects on decades in bands including Chisel, his transition from journalism into content strategy for the design world, and what happens when art, family life,...

It's the first listener mailbag episode! Tim answers real money & personal finance questions from listeners about ethical investing, managing debt, and overcoming money-related shame. He explains how to easily invest according to your values, how to balance saving while paying off student loans, and when to use savings to tackle credit card debt. The conversation ends with a thoughtful reflect...

Benjamin Percy has built a career bridging literary fiction, comics, and Hollywood storytelling. As the author of acclaimed novels, comic book arcs for Marvel and DC, and scripts for film and audio drama, Ben joins Tim to discuss the craft and discipline behind a self-employed creative life. He talks about writing routines, handling rejection, learning to navigate the business side of art, and bal...

What would it take for work to become optional? In this solo episode, Tim walks through a simple framework for estimating your “enough” number—the amount you’d need in savings & investments to reduce or even eliminate the obligation to work. Using the 4% and 25× rules, he explains how to calculate a  target nest egg amount, why it’s useful even if you never plan to retire, and how small, consi...

For more than 30 years, Michael Perry has built a life around words — from essays and bestselling books to one-man shows and live events. In this conversation, Mike shares how his blue-collar roots shaped his approach to creative work and money, why he still keeps his nursing license “just in case,” and what it really takes to sustain a self-employed creative life. He and Tim talk about saying no...

What comes to mind when you hear the word “wealth”? In this episode, Tim explores how our ideas about money are shaped not just by math & spreadsheets, but by deep emotional lessons from family, culture, and experience. He unpacks why textbook definitions of wealth often fall short, shares perspectives from author Morgan Housel, and offers a new way to think about building abundance: creating...

Sam Ratto is the founder of Videri Chocolate Factory in Raleigh, NC, and recently started Golf Golf Golf, an indoor golf simulator business. In this episode, Sam shares his winding path from surfing & skateboarding culture, launching a bean-to-bar chocolate company, and building a new hospitality venture around his love of golf. He talks about the realities of small business finance, lessons l...

In this episode, we unpack why having the right amount of cash in savings is essential—but why holding on to too much can quietly hurt your financial future. While an emergency fund provides short-term stability and peace of mind, excess cash loses value every year to inflation. By contrasting the short-term safety of savings with the long-term growth of investments, the conversation highlights th...

Musician Macie Stewart has been performing since her teens, from early bands like Kids These Days to co-founding Finom & becoming a fixture in Chicago’s improvised music scene. In this episode, she talks about finding community at Constellation (an excellent Chicago venue), balancing the realities of freelance income with creative freedom, and what success looks like for her today. One key tak...

Buying a home is often called “the best investment you’ll ever make”—but is that really true? In this episode, Tim breaks down what it means to think of a primary residence as an investment, comparing real estate returns to long-term stock market performance. Using real numbers, historical data, and examples, he highlights the risks, tax benefits, and long-term advantages of homeownership while ch...

Sam Kassirer is a musician, producer, and the founder of The Great North Sound Society, a residential recording studio in rural Maine. In this episode, he talks about his path from gigging pianist to touring with Josh Ritter and building a creative retreat where bands can record together under one roof. Sam shares practical insights about balancing art and money, including how he structures rates,...

In this episode, we explore the question of when it actually makes sense to work with a financial advisor. Sometimes you already know what needs to be done—you just need accountability or a new perspective to make it happen. Other times, big changes in income, unexpected windfalls, or simple uncertainty about “am I doing okay?” make professional guidance valuable. The conversation emphasizes that...

Brad Cook is a record producer based in Durham NC. Although he has been  a professional musician & artist manager in the past, Brad has focused on production full-time for the last seven years. He has produced dozens of records since then, working primarily from his home studio. And he's one of my best friends! Brad and I became pals when we both toured with Sharon Van Etten back in 2014-15 (B...

In this episode, we dig into one of the most persistent investing dilemmas: knowing when the “right time” to invest actually is. Through personal stories and historical examples, we explore why the market always feels risky in the present—even though the biggest long-term gains often come to those who invested during turbulent times. The message is simple but powerful: the best time to invest is w...

Christian Frederickson is a composer, violist, and sound designer whose career has bridged the worlds of classical music, experimental performance, and theater. In this episode, we talk about his transition from conservatory-trained musician to co-founder of the influential instrumental group Rachel’s, and his later work composing and designing sound for stage and dance productions. In this conver...

The next recession isn’t a matter of if but when . While no one can predict the exact timing, there are practical steps you can take right now to make your finances more resilient before the economy takes a downturn. This episode shares four tips that anyone can use to improve financial stability & security to help navigate uncertaintimes. Key takeaways Recessions are unpredictable but inevita...

Mikael Jorgensen is best known as the keyboard player in Wilco, a position he's held for 20+ years. But before that, Mikael and I were both staff engineers at Soma Electronic Music Studios in Chicago. Mikael shares stories about his dad, who was also a recording engineer, touring & releasing records with his first bands, how he got started at Soma and how he moved from recording Wilco to being...