The Thing We Never Talk About

Most people use the words "investing" and "trading" interchangeably — but they're actually two very different games, and the one you choose to play makes all the difference. Trading takes a lot of work & relies heavily on luck with limited upside. Investing, by contrast, means committing money to things you believe are fundamentally worth owning and holding them long enough for compounding to do the work for you. Tim walks through why trading is so hard to do, why patient long-term investing is far easier than most people assume, and why relying on the financial news media can actually lead you astray if you're trying to build real wealth.
One Key Takeaway: Investing — owning good things for a long time — is a game almost anyone can win.
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In this episode, Tim sits down with Scott Adamson — touring front of house audio engineer and founder of The Production Academy — for a wide-ranging conversation about building a life in live sound. Scott traces his career from mixing indie bands in small clubs to working with Grammy-winning artists in arenas, sharing how luck, relationships, and just sticking around long enough opened doors he couldn't have anticipated. He shares his experience with  the financial realities of the touring world and speaks candidly about The Production Academy, the online education platform he spent nearly a decade building, including what he got right, what he got wrong, and how that informs his thinking going forward. Throughout the conversation, Scott brings a refreshingly self-aware perspective on his own financial habits: what he wishes he'd done sooner, how regularly investing even a little helps in the long run, and what he'd do differently as an entrepreneur the next time around.
Scott's question for Timothy: How do we approach online education?
Key Takeaways:
Scott describes his work as a creative collaboration with artists, translating what happens on stage into what the audience actually hears and feels.
He spent his twenties and early thirties living cheaply, often without an apartment, bouncing between tours — but with no savings to show for it, a gap he deeply wishes he had addressed sooner.
Despite the touring industry's lack of contracts or union protections for crew, Scott notes that touring people rarely talk openly about rates — a habit that works against them collectively, though he actively tries to share what he knows with colleagues.
Scott spent close to a decade building The Production Academy, generating around half a million dollars in revenue — but with very little profit, largely because he focused almost entirely on product development and not enough on sales and marketing.
He identifies his biggest entrepreneurial lesson as the importance of complementary skill sets: building something alone means doing everything yourself, and the things you're not naturally good at — in his case, sales — tend to get neglected.
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The Production Academy

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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