The Thing We Never Talk About

The stock market is likely to go up over time — but that doesn't help if it crashes right when you need the money. In this solo episode, Tim uses the framing of "insurance" to explain why diversification across cash, bonds, and stocks is a way of managing the known risks that come with each type of investment. Cash protects against short-term market drops; stocks protect against inflation over the long term; and bonds help bridge the gap in between. Tim walks through how adjusting the mix of those asset classes — and diversifying within them — can smooth out the ups and downs to match your timeline and your feelings about risk.
One Key Takeaway: Diversification isn't literally insurance, but it plays the same role: balancing the risks of each type of investment against the strengths of the others so that no single risk can derail your financial life.

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In this episode, Tim sits down with tour manager & tour accountant Paul Dalen for a candid conversation about money, career, and what it actually takes to make retirement a real possibility after decades on the road. Paul traces a career that has taken him from front of house audio engineering to production management to artist management and back to touring, including a period about 15 years ago when he found himself broke and starting over from scratch in his mid-50s. He talks openly about what that reset taught him, how a combination of fiscal discipline and good fortune in the markets turned things around, and why he thinks the touring industry's culture of financial avoidance does real damage to the people in it.
Paul's question for Tim: When might an S corp or any other corporate entity be worth considering for freelancers?
Key Takeaways:
Paul has spent his entire adult life in the music industry, moving across roles from front of house engineer to production manager to artist manager to tour manager — a career arc shaped more by relationships and opportunity than by deliberate planning.
His approach to underpaid gigs early in his career was to say yes for a short run while making clear it wasn't his normal rate, a move that consistently led to better opportunities.
After his artist management business failed around 15 years ago, Paul found himself broke in his mid-50s and returned to touring with his tail between his legs. His path back to financial stability was built on basic principles — budgeting, fiscal discipline, and consistent investing.
He advises people new to investing to just start somewhere, even imperfectly, rather than waiting until they fully understand how to optimize.
Paul's approach to spending is experiential rather than material: theater, travel, good meals occasionally, and tickets to shows he wants to see. He also notes that not eating out regularly has been one of the quieter contributors to financial stability over the years.
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Money has different jobs depending on when you need it — and confusing what works for one timeline with what works for another is one of the most common financial mistakes. In this solo episode, Tim walks through the difference between saving money and building wealth, using this definition of wealth as a guide: the ability to do what you want, when you want, with whom you want, for as long as you want. From cash savings for short-term needs, to CDs and Treasury bills for medium-term goals, to stock market investing for long-term goals like retirement, Tim lays out a simple framework for how matching your money to its purpose builds wealth both now and later.
One Key Takeaway: Saving money and building wealth are not the same thing. Match your money to its timeline: cash for the short term, stable interest-bearing accounts or investments for the medium term, and stock market investing for the long term.
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In this episode, Tim sits down with Serena Lander — self-employed artist, tattoo artist, and owner of a multi-unit property — for a conversation about building a creative life on your own terms. Serena traces her path from tattooing as a teenager in British Columbia, when she was one of only a handful of women in the craft in North America, through nearly four decades of working entirely for herself. She talks openly about her ambivalent feelings towards money and the practical decisions that have shaped her financial life like keeping overhead low and investing in things she actually believes in. It's a conversation about finding your own version of financial stability without abandoning the values that drew you to a creative life in the first place.
Serena's question for Tim: Can you share some ideas about setting goals in life and trying to engage more enthusiastically with your finances? I wish there was a way to make it more sparkly for myself so that I would do it.
Key Takeaways:
Serena started tattooing at 19 in British Columbia at a time when there were only a handful of women doing it in all of North America.
She has spent her entire career working for herself, supported early on by keeping her overhead extremely low.
Buying a house at the bottom of the market in 2011 and gradually subdividing it into four rental units has turned into a financial foundation she didn't originally plan for, with rental income now covering her mortgage.
Serena reflects on the punk rock and alternative music community's cultural aversion to money, and how that narrative — money as part of the system, financial participation as selling out — has made it harder for people in those communities to build long-term stability.
She finds it easier to engage with financial decisions when they are tangible and values-aligned, like adding solar panels to her house.
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Serena Lander on Instagram
Serena Lander's website

Should you pay off your mortgage early or invest the money instead? In this solo episode, Tim walks through a real case study involving a couple who received a significant one-time windfall and want to know how to use it wisely. He compares three options — investing the full amount right away, paying off the mortgage entirely, or splitting the difference — across a twenty-year time line, and shares what the numbers actually revealed. The results might surprise you, and one of the most important factors turns out to be one that doesn't show up in any spreadsheet.
One Key Takeaway: When comparing paying off debt versus investing, the math usually favors investing — but only if you can actually stick to your investment plan over many years and decades.
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