The Thing We Never Talk About

Having more money than you’ve ever had before sounds like a great problem to have (and it is), but it also creates a kind of analysis paralysis that seldom gets talked about. In this solo episode, Tim explores what happens when the rules that work for managing a normal amount of money stop applying, and why doing nothing — letting all the money sit as cash indefinitely — is the wrong move. He walks through a practical framework for thinking about sudden abundance: how to figure out how much to keep in cash, how to decide what to invest, and how to match your investment strategy to your timeline and goals.

One Key Takeaway: Define how much you need in the next two to three years and keep that in cash. Everything above that should be put to work by investing it.

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In this episode, Tim sits down with Matthew Wortz, a New York-based actor who came to the craft after decades in conventional employment. Matt describes how being laid off in his previous job as a web designer led to showing up at an open call for extras on a film set. What started as something to stay active has turned into a serious second career: he's now a SAG-AFTRA member, working his way up through featured background roles, and thinking carefully about what the next phase looks like. Matt shares how the financial habits he learned during previous economic downturns helped him navigate the transition, and what it's like to build something new when you've spent most of your life as an employee.

Matt's question for Tim: I'm thinking about setting up a loan-out company for my acting work. What advice would you give someone who has spent a lifetime in 9-to-5 jobs and is now creating and managing a small business for the first time?

Key Takeaways:

1. Matthew tried acting after being laid off from a web design role, signing up to be an extra almost on impulse, and found that being on set exciting and engaging.
2. Breaking into the industry as an extra is unglamorous and low-paying, but the network of people doing the same work has helped him find new opportunities.
3. As a member of the SAG-AFTRA union, Matt is now able to earn more money as an actor. And being reliable on set has led to production staff recognizing him and recommending him for more roles.
4. Matt's most valuable financial habit during the transition to a new career was having lived through the 2008 layoff, which taught him to move quickly into budgeting mode and adjust his lifestyle to fit the new financial reality.
5. One practical reason Matt is drawn to the loan-out structure is the paperwork problem: working for many different production companies means receiving pay stubs and 1099s from dozens of sources, and consolidating that into a single business entity would simplify both bookkeeping and tax filing significantly.

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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:

1. 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.
2. 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.
3. 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.
4. He advises people new to investing to just start somewhere, even imperfectly, rather than waiting until they fully understand how to optimize.
5. 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:

1. 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.
2. She has spent her entire career working for herself, supported early on by keeping her overhead extremely low.
3. 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.
4. 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.
5. 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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In this episode, Tim sits down with Richard Dansky — game narrative expert, fiction writer, and tabletop role-playing game designer — for a wide-ranging conversation about building a creative career across multiple formats and revenue streams. Richard traces his path from tabletop games starting in the '90s through nearly three decades of video game work, including a long tenure as the central narrative resource for Ubisoft's Tom Clancy franchise, while continuing to write fiction, contribute to tabletop games, and co-author a graphic novel along the way. He talks candidly about the economics of that kind of career: how he thinks about rates across different formats, why he has always lived well below his means, and why he wishes more writers understood their own professional value. He also shares hard-won wisdom about navigating rejection and knowing when to walk away from a bad deal.

Richard's question for Tim: How do you think  about melding various revenue streams, as these days every author's got to have a Patreon/Substack/YouTube channel/podcast/newsletter/online store/convention presence etc.

Key Takeaways:

1. Richard describes his entry into both tabletop and video games as largely relationship-driven — a reminder that in creative industries, showing up, being reliable, and knowing the right people often matters as much as talent.
2. He has maintained a remarkable ability to work across multiple formats simultaneously: video games by day, tabletop and fiction by night — treating each as a distinct creative sandbox with its own rules and rewards.
3. Richard's fiction acceptance rate is around 3.7%, which he notes is listed as above average. It's a useful reminder that rejection is the norm in creative work, not a signal of failure.
4. Richard describes the best financial habit of his career as consistently spending well below his means, and how knowing he can afford his lifestyle frees up mental and creative energy.
5. He argues that writers and narrative designers are frequently underpaid because the value of their work is hard to quantify, and that the industry actively works to make creative professionals feel their contributions are worth less than they are.

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Richard's website
Richard's LinkedIn profile, where he shares insight on game narrative design
The issue of Dark Yonder in which I first learned about Richard

Doing nothing with your money feels safe — but it comes with real costs, both financial and emotional. In this episode, Tim explains why cash is essential for short-term stability but loses value over time to inflation, and why investing anything beyond your cash reserve is one of the most important financial moves you can make. He also explores two emotional patterns that keep people stuck: "the leaky bucket", where money slowly disappears without intention, and the "but what comes next" mindset, where fear of making the wrong decision leads to making no decision at all. The solution to both, it turns out, is the same: define how much cash you actually need, stick to that number, and put everything above it to work for you through investing.

One Key Takeaway: Making no decision for what to do with your money is itself a decision — and it usually costs you.

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In this episode, Tim sits down with Angela Hugghins, esthetician & founder of Cult of Reason skincare, for a wide-ranging conversation about what it looks like to build multiple businesses on your own terms. Angela shares how she structured her solo practice to protect her hands, her energy, and her lifestyle after nearly 30 years in the industry, why she made a significant price jump despite fears of losing clients, and how she thinks about the break-even math before introducing any new product or equipment. She also talks candidly about the origins of Cult of Reason, the unexpected challenges of running a product business, and the recent purchase of a commercial building to house her businesses and generate rental income.

Angela's question for Tim: Now that we're landlords, what are the tax advantages of owning commercial real estate, how do we maximize rental income, and what other ways can we benefit from this new structure?

Key Takeaways:

1. Angela capped her working days at four per week after years of overworking, a deliberate lifestyle decision driven by the physical demands of her craft.
2. She hired a virtual assistant who spends just 30 minutes a day managing her emails and client communications — a small investment that she says has paid off in stress reduction far beyond its dollar cost.
3. After building a wait list of over 200 clients, Angela made a significant price increase, gave clients three months of advance notice without disclosing the exact amount, and lost only three or four people as a result.
4. Angela launched Cult of Reason to recreate a discontinued product she had relied on, starting with a single formula developed over two years through a custom cosmetics lab, funded entirely out of pocket.
5. She describes Cult of Reason as a passion project that is now self-funding, and identifies supply chain disruptions and tariffs on imported ingredients as challenges she hadn't anticipated when she started.

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Cult of Reason Skincare
Cult of Reason on YouTube