The Thing We Never Talk About

Timothy Iseler
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  • 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. Emily Flake – Cartoonist

    5 DAYS AGO

    Emily Flake – Cartoonist

    In this episode, Tim talks with cartoonist, writer, and teacher Emily Flake about building a creative career through multiple income streams, persistence, and adaptability. Emily shares what it’s really like to work in fields where rejection is common, success is unpredictable, and financial stability requires constant adjustment. Together, they explore the tension between creative fulfillment and practical money decisions, including saving, budgeting, and long-term planning. One Key Takeaway: A sustainable creative career is built less on sudden success and more on resilience, flexibility, and steady habits that support both artistic and financial health. Emily’s question for Tim: I’m a freelancer whose income varies wildly, and not only am i terrible with money but I’m actively afraid of thinking about it. I play chicken with my bank account, which is a checking account, because i don’t have a savings account. Don’t you dare even ask if I have a retirement account. I’m 48 gd years old. I guess my question is: how f****d am I? Key Takeaways: Emily Flake describes how her career has been built from many different income streams, including cartooning, writing, teaching, comedy, and running creative programs, rather than from one single job.She explains that publishing work in prestigious outlets like The New Yorker brings visibility and credibility, but does not guarantee long-term financial security.Emily talks about the ongoing reality of pitching work, receiving rejections, and learning to persist in an industry where “no” is far more common than “yes.”She reflects on how she balances creative fulfillment with practical concerns like paying bills and maintaining steady income.Emily speaks candidly about her discomfort with money, budgeting, and long-term financial planning, and how this has affected her decisions.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Emily's websiteSt Nell's Humor Writing ResidencyEmily's contributor page at The New Yorker

    1h 3m
  2. Easy Cash Flow: The “Reservoir System”

    2 FEB

    Easy Cash Flow: The “Reservoir System”

    Managing money with an up & down income can feel overwhelming, especially when it comes to planning for the future. In this episode, Tim introduces the “Reservoir System,” a simple, intuitive framework for managing cash flow when your don't know how much you'll make this month or this year. Using the metaphor of managing a town's water supply, he explains how checking, savings, and investment accounts each serve a distinct purpose, and how to know when to keep cash on hand, when to save, and when to invest. This episode is especially helpful for freelancers, creatives, and self-employed people who want more stability without relying on traditional budgets. One Key Takeaway: Financial stability with an irregular income comes from prioritizing cash reserves first, then savings, and only investing once your short-term needs are fully covered. Links:Sign up for weekly Office HoursSend me a question to be answered on a future episode

    17 min
  3. Tony Rolando – Founder of Make Noise Music

    26 JAN

    Tony Rolando – Founder of Make Noise Music

    In this episode, Tim  talks with Tony Rolando, musician, instrument designer, and founder of Make Noise Music, about building electronic musical instruments, growing a niche manufacturing business, and staying creatively grounded as success scales. Tony shares how his background as a musician shaped the unconventional design philosophy behind Make Noise’s modular synthesizers. They discuss the realities of scaling a creative business, including hiring, cash flow, and the tradeoffs between growth and personal freedom. The conversation also touches on Tony’s evolving relationship with money, health, and what it means to use success to support a meaningful life. Tony's question for Tim: With the way the current administration is increasingly isolating the US from the global economy, I have had the thought that I should shift my investments to be heavier in European and emerging markets. Add to that, that my retirement portfolio is almost entirely SRI and I sometimes feel it makes even more sense to shift to the European market. Do you have thoughts on this?  Key Takeaways: Tony began Make Noise in 2008 after leaving a low-paying job at Moog Music, initially building modules by hand with no formal business plan.Early Make Noise designs emerged from Tony’s personal musical needs—creating modules that didn’t yet exist in the small modular synth market at the time.Tony approaches instrument design as a musician first, deliberately stacking functions into single controls to make instruments more expressive and playable.As Make Noise grew, Tony learned that hiring employees gave him his personal life back—but did not necessarily increase his income.Tony shares personal reflections on money, saving habits, health challenges, and the importance of actually using money to enjoy life.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Make Noise MusicMake Noise's YouTube pageTony's Bandcamp page

    1h 1m
  4. Why Pay Someone To Manage Investments?

    19 JAN

    Why Pay Someone To Manage Investments?

    With investing tools cheaper & more accessible than ever, why would anyone still pay an advisor to manage their investments? In this solo episode, Tim breaks down how the biggest benefit of investment management isn’t better stock picks or secret knowledge, but help with follow-through, emotional decision-making, and actually doing the things you already know you should be doing. The episode closes with practical guidance on how to decide whether managing your own investments or delegating that responsibility makes the most sense for you. One Key Takeaway: Paying for investment management isn’t about access to information or tools—it’s about whether having support helps you make better decisions and stick with them over time. Links:Sign up for weekly Office HoursSend me a question to be answered on a future episode

    21 min
  5. Ryan Isaac - Education Fundraiser & Baseball Newsletter Writer

    12 JAN

    Ryan Isaac - Education Fundraiser & Baseball Newsletter Writer

    Ryan Isaac is an education fundraiser & longtime baseball insider who spent more than a decade working in professional baseball. In this episode, Ryan shares how he broke into the industry, what it was like navigating the uncertainty & mobility of baseball careers, and why becoming a parent ultimately reshaped his priorities. He reflects on the identity shift that comes with leaving a dream job and finding new ways to stay connected to the work you love. The conversation also explores how Ryan rediscovered his voice through writing and launched his baseball newsletter, Warning Track Power, as a creative outlet beyond his day job. Ryan's question for Tim: What was the biggest obstacle you faced during your career transition?  Key takeaways: Ryan shares his early career ambitions as a writer and journalist, including working at Wine Spectator in New York City while nurturing a long-standing passion for baseball. He describes leaving journalism to pursue a career in professional baseball during the early “Moneyball era,” including moving to San Diego without a job lined up to put himself closer to opportunity. Ryan recounts how a chance phone call led to his first full-time role with the San Diego Padres, marking his official entry into Major League Baseball operations. After leaving baseball, Ryan transitioned into fundraising for an independent school, gradually building experience through expanded responsibilities during the early COVID period. During the pandemic, Ryan reignited his creative outlet by writing about baseball, leading to the launch of his newsletter Warning Track Power as a personal and intellectual release.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Ryan's newsletter Warning Track PowerWarning Track Power's Substack page

    59 min
  6. Financial Forecasts Are Bullsh!t

    5 JAN

    Financial Forecasts Are Bullsh!t

    Every year, financial “experts” roll out confident predictions about what the markets and economy will do next — and almost every year, they’re wrong. In this solo episode, Tim explains why financial forecasts are so appealing, why they’re fundamentally unreliable, and how chasing certainty can actually hurt your long-term financial health. Instead of guessing the future, he lays out a simple, durable framework for building stability, flexibility, and peace of mind in an unpredictable world. One Key Takeaway: You don’t need to predict the future to build financial security — simple habits, long-term thinking, and preparation for uncertainty matter far more than any market forecast. Links:Financial Forecasts Are Bullsh!tSign up for weekly Office HoursSend me a question to be answered on a future episode

    17 min
  7. Todd Trainer - Drumming Instructor

    29/12/2025

    Todd Trainer - Drumming Instructor

    Drumming instructor Todd Trainer joins Tim to talk about how an unexpected job loss pushed him into building a new career around teaching. He shares the story of growing his student base from DIY flyers to a full teaching practice, and why helping beginners find confidence & creativity has become some of the most meaningful work of his life. Todd also talks about adapting his teaching style for different learners and the philosophy that guides his approach to drumming instruction. Key Takeaways: Todd Trainer—best known as the drummer of Shellac—shares how losing a long-time job pushed him toward drumming instruction as a new career path. He started his teaching business in DIY fashion, putting up flyers & offering mobile lessons at his students' homes or rehearsal spaces. Eventually, Todd (and his wife, a designer) built a website that features scheduling tools & a payment system, which have been essential to the business’s success.His teaching philosophy emphasizes creativity, individuality, and imagination—encouraging students to develop their own unique style rather than chasing technical perfection. Todd finds deep fulfillment in teaching beginners, especially children, and describes how helping them discover their first drumbeat is one of the most rewarding parts of instruction. Teaching has become emotionally meaningful for Todd: the value exchanged between student and instructor goes far beyond the time they spend together.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Todd Trainer Drumming InstructionTwin Cities Drum CollectiveShellac of North America

    50 min
  8. 4-Week Financial Detox

    22/12/2025

    4-Week Financial Detox

    Holiday spending can creep up fast — and the new year is the perfect time to reset. In this episode, Tim introduces the 4-Week Financial Detox, a simple step-by-step process designed to help you pause discretionary spending, reset your baseline expenses, eliminate costly subscription “leaks,” and refocus your money on what truly matters. Whether you’re rebuilding after the holidays or just ready to use your money more intentionally, this short reset can help you start the year with more clarity, control, and confidence in your financial life. One Key Takeaway: Small, temporary changes to your spending habits can create lasting improvements in financial health — especially when you focus your money on what genuinely enriches your life. Links:4-Week Financial DetoxSign up for weekly Office HoursSend me a question to be answered on a future episode

    17 min
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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
    47
  • Rating
    Explicit
  • Copyright
    © 2026 Timothy Iseler

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