The Thing We Never Talk About

In this solo episode, Tim explores the tension between planning for the future and actually taking action in the present. Using examples from fitness, travel, and financial planning, Tim makes the case that over-thinking and over-planning can quietly become an obstacle — doing the work to decide whether to do the work, without ever getting started. Thoughtful, deliberate decision-making matters, but waiting for a perfect plan is itself a form of inaction, and that right here, right now is the only time any of us has to change our path for the better. Tim also walks through two common financial planning scenarios — buying a house and saving for retirement — to show how taking positive "imperfect" action today puts you in a stronger position to meet those moments later.
One Key Takeaway: Don't let perfect be the enemy of good. No plan can guarantee the future, but taking positive action right now — even small, imperfect steps — can give you more and better options later.
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In this episode, Tim sits down with Jason Narducy — musician, self-published author, and longtime member of Bob Mould's band and Superchunk — for a wide-ranging conversation about what it actually means to build a life in music. Jason shares the arc of his career, from a major label deal in the nineties through running a painting company for 20 years, to eventually going all-in on music again. He talks candidly about the economics of touring, the difference between working as a hired band member versus leading his own project, and how his solo shows have become one of his most rewarding musical outlets. Jason also discusses his self-published book Mostly the Van — a collection of short, human-centered essays about life in that middle space between fame and hobby — and reflects on the financial habits he's developed over decades of irregular income, including a hard-won lesson about credit card debt.
Jason's question for Tim: What helpful financial advice do you have for musicians or any self-employed creatives?
Key Takeaways:
Jason ran a painting company for 20 years alongside his music career, providing income stability during slower periods — until he shut it down in January 2023 and committed fully to music.
He describes his approach to scheduling: he commits fully to every project and doesn't back out, relying on bands planning ahead to lock in dates rather than managing a complex personal system.
Jason reflects on the hidden complexity of being a working musician, noting that success requires skills far beyond playing — traveling, writing, interviews, interpersonal relationships, and financial awareness — and that many musicians aren't equally equipped for all of them.
When touring with the REM tribute band he leads with Michael Shannon band, Jason prioritizes comfort over cost-cutting, believing that keeping experienced musicians happy is what allows the project to keep going long-term.
His strongest personal financial habit: not spending money he doesn't have. An early experience with credit card debt left a lasting impression that shaped how he has managed money ever since.
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Jason's Instagram
Jason's Threads

In this solo episode, Tim explores the tension between intuition and evidence when it comes to investing. He explains why reacting to how you  feel in the moment often leads to poor decisions, and how long-term data consistently points toward more effective strategies. Through real-world examples, Tim breaks down why trying to time the market rarely works, how automation and consistency can improve outcomes, and why patience is the most powerful force in building wealth. This episode is a reminder that successful investing isn’t about being right in the short term—it’s about aligning your behavior with what actually works over decades.

One Key Takeaway: The best investors don’t follow their instincts in the moment—they follow the evidence and stay consistent over the long term.
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Selling out during the market’s worst days can hurt you, research shows — here’s how much you could lose
Timing the Market Can Often Mean Missing the Best Days
Timing the Market: Why It’s So Hard, in One Chart
Here's the Average Stock Market Return in Every Month of the Year

In this episode, Tim sits down with Christen Carter, founder of Busy Beaver Buttons & Merch, to explore how a DIY punk project grew into a decades-long business rooted in creativity, community, and resilience. Christen shares the scrappy early days of building a niche product for an overlooked audience, how she navigated major shifts in technology and demand, and the lessons she’s learned about leadership, hiring, and staying true to her values as the company scaled. The conversation also goes deep on money—covering scarcity mindset, early financial experiences, real estate decisions, and the balance between saving for the future and enjoying life today. Along the way, Christen offers an honest look at burnout, risk-taking, and what it actually takes to build something that lasts.
Christen's question for Tim: how do you coach people whose income can fluctuate depending on what their business is doing to know when to save or spend like on a vacation or something fun?
Key takeaways:
Christen shares how she started Busy Beaver as a DIY punk project, spotting a niche for small custom buttons that no one else was really serving.
She describes her early, scrappy approach to growth—reaching out to record labels, building within creative communities, and going direct-to-customer from the start.
Christen reflects on the shift from doing creative work to running a company, including learning operations, HR, and building systems from scratch.
She talks about how peer-to-peer learning and entrepreneurial communities helped her understand finance, forecasting, and how businesses actually work.
Christen shares how early life experiences shaped a lasting scarcity mindset and discusses her long-term financial approach, including cautious decision-making, investing in real estate, and actively working to balance saving with actually enjoying her life.
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Busy Beaver Buttons & Merch

In this solo episode, Tim pulls back the curtain and shares exactly how he invests his own money — not hot stock tips or market predictions, but the philosophy and decision-making framework behind his choices. He explains why he invests, how he thinks about risk and time, why maintaining strong cash reserves is essential, and why his timeline shapes nearly every decision he makes. Tim walks through when he buys, when he sells, and why he ignores financial media noise in favor of long-term discipline. This episode is about process over prediction — and about building a strategy you can stick with for decades.

One Key Takeaway: The real edge in investing isn’t knowing what the market will do next — it’s having a clear plan, a long timeline, and the discipline to follow it.
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