The Thing We Never Talk About

Timothy Iseler
  • 4.8 (14)
  • Education

The Thing We Never Talk About is an educational podcast about personal finance for creatives and other weirdos. We'll discuss managing cash flow with a lumpy income, when to save & when to invest, and how to reduce stress & build confidence when it comes to your money. No hot stock tips, no complicated strategies, and no finance bro jargon. We'll hear from artists, musicians, creative professionals, and other weirdos about how they navigate these questions for themselves. The Thing We Never Talk About is hosted by Timothy Iseler, CFP®, a former recording & touring audio engineer with 18 years experience in the music industry.

  1. 2d ago

    Alan Sisto - Podcaster & Writer

    In this episode, Tim sits down with Alan Sisto, host of The Prancing Pony Podcast, for a conversation about how a podcast on the works of J.R.R. Tolkien went from side hobby to full-time job. Alan started the show while working as a photographer and voiceover artist, and eleven years and 400+ episodes later it’s now his main source of income. He describes how a Facebook group and a voiceover coach’s advice got him started, and how his co-host stepping down and COVID’s effect on his other work pushed him to go all in. Alan talks about how he measures success by community support more than revenue, and how he’s planning for retirement as a self-employed creator. Alan’s question for Tim: What is your prediction for the near term future of the housing market? Key Takeaways: Alan started the podcast as a side hobby while working as an architectural photographer and voiceover artist, and it took roughly three years before he realized the audience was big enough to grow into something more.After his co-host stepped down in 2022, Alan added a daily show and a twice-weekly stream to turn the podcast into his full-time job.He defines success as community first and revenue second, pointing to a Facebook group of about 10,000 members and a member's-only Discord of 800 to 1,000 supporters.Because the content is evergreen, about two-thirds of monthly downloads come from episodes older than 60 to 90 days, with roughly a third of revenue coming from the first four seasons.Alan tracks every dollar with budgeting software, so the voluntary expenses stay visible. He credits this with being able to support his lifestyle while working for himself on a project he loves.Links:Send me a question to be answered on a future episode. Sign up for the Keep It Easy newsletter. The Prancing Pony Podcast

    Alan Sisto - Podcaster & Writer

  2. Oct 26

    More Money, More Questions

    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. Links:Send me a question to be answered on a future episode. Sign up for the Keep It Easy newsletter.

    More Money, More Questions

  3. Oct 19

    Matthew Wortz – Actor

    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: 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.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.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.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.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.Links:Send me a question to be answered on a future episode. Sign up for the Keep It Easy newsletter.

    Matthew Wortz – Actor

  4. Oct 12

    Diversification Is “Insurance” For Investments

    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. Links:Send me a question to be answered on a future episode. Sign up for the Keep It Easy newsletter.

    Diversification Is “Insurance” For Investments

  5. Oct 5

    Paul Dalen – Tour Manager & Tour Accountant

    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.Links: Send me a question to be answered on a future episode. Sign up for the Keep It Easy newsletter.

    Paul Dalen – Tour Manager & Tour Accountant

  6. Sep 28

    Saving Money vs. Building Wealth

    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. Links:Send me a question to be answered on a future episode. Sign up for the Keep It Easy newsletter.

    Saving Money vs. Building Wealth

  7. Sep 21

    Serena Lander - Tattoo Artist

    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.Links:Send me a question to be answered on a future episode. Sign up for the Keep It Easy newsletter. Serena Lander on Instagram Serena Lander's website

    Serena Lander - Tattoo Artist

  8. Sep 14

    Case Study: Paying Off Mortgage vs Investing

    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. Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.

    Case Study: Paying Off Mortgage vs Investing
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Trailer

4.8
out of 5
14 Ratings

About

The Thing We Never Talk About is an educational podcast about personal finance for creatives and other weirdos. We'll discuss managing cash flow with a lumpy income, when to save & when to invest, and how to reduce stress & build confidence when it comes to your money. No hot stock tips, no complicated strategies, and no finance bro jargon. We'll hear from artists, musicians, creative professionals, and other weirdos about how they navigate these questions for themselves. The Thing We Never Talk About is hosted by Timothy Iseler, CFP®, a former recording & touring audio engineer with 18 years experience in the music industry.

Information

  • Creator
    Timothy Iseler
  • Years Active
    2025 - 2026
  • Episodes
    79
  • Rating
    Explicit
  • Copyright
    © 2026 Timothy Iseler

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