The Thing We Never Talk About

Timothy Iseler

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. Katie Cunningham - Producer & Writer-Director

    2d ago

    Katie Cunningham - Producer & Writer-Director

    In this episode, Tim sits down with Katie Cunningham, a freelance producer and writer-director, for a conversation about risk, identity, and how she built a creative life on your own terms. Katie shares the story of leaving a corporate marketing job in 2022 to write and direct a self-funded short film (even though her finances weren't necessarily ready for the leap), and how that decision led to later creative success. She talks candidly about what it took to rewire a long-held identity as someone who was "bad with money," the practical systems that changed her relationship with her finances, and Produce Your Life, a project she launched to apply a production mindset to everyday life. It's a conversation about building financial confidence step by step and trusting yourself enough to take the leap before everything feels perfectly ready. Katie's question for Tim: Can we talk about rewiring my internal story to look directly at and take responsibility for money instead of remaining in a state of chaos? Key Takeaways: Katie left her corporate marketing job in 2022 to pursue writing and directing, despite knowing that it was a financial risk.Before making the leap, she spent months consolidating scattered retirement accounts and reviewing her spending to trim unnecessary expenses — unglamorous groundwork that gave her a clearer picture of where she actually stood financially.As a new freelancer, Katie embraced a period of deliberate "unmooredness," traveling and taking on flexible freelance production work without a fixed home base, which matched the freedom she identified as a core value.Katie's rules for deciding which jobs to take are built around how a project sustains her lifestyle costs, or whether it's an opportunity to learn from someone she admires (even at a lower rate).Katie's biggest piece of advice for freelancers is to know exactly what their lifestyle costs every month, since that number changes everything about which gigs make sense to take and removes a huge amount of background financial stress.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Katie's website

    1h 16m
  2. You Can't Out Earn Your Spending

    Jun 22

    You Can't Out Earn Your Spending

    When people feel financially stretched, it can be hard to decide where to cut back. What if you just focused on earning more instead? It seems like the logical solution — but there's a problem with that logic: almost everyone increases their spending when their income goes up. The result is that you find yourself right back where you started, just at a higher level. In this episode, Tim shares a real example of a household earning over $400,000 a year that still had nothing left over, why trying to out earn your spending rarely works, and a practical framework for building a gap between what you earn and what you spend — and keeping it. One Key Takeaway: Earning more won't solve a spending problem. Instead you need to spend below your means, save the rest, and widen that gap every time your income goes up. Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.

    10 min
  3. Rob Mazurek – Abstractivist

    Jun 15

    Rob Mazurek – Abstractivist

    In this episode, Tim sits down with Rob Mazurek — composer, painter, and self-proclaimed abstractivist — for a wide-ranging conversation about what it looks like to build a life entirely around creative vision. Rob traces his path from Chicago's boundary-pushing music scene of the '90s through his current life in Marfa, Texas, where he and his wife have built a low-overhead, high-quality existence that allows him to keep making exactly the work he wants to make. He talks candidly about the financial realities of that life — the relationships with festival directors and venue operators that have allowed him to command respectable fees over decades, the deliberate choice to keep expenses low, and the honest admission that at 60, he has neither investments nor life insurance and knows it's time to change that. Throughout the conversation, Rob brings the same openness and curiosity he applies to his art to questions about money, and what emerges is a portrait of someone who has always prioritized creative integrity, and is ready to think seriously about what comes next. Rob's question for Tim: What should I do concerning investment strategies and life insurance? I have neither. Key Takeaways: Rob describes himself as an abstractivist, a term he coined in the ‘90s to capture the holistic nature of his work across music, art, and performance.His move to Marfa came almost by accident, and what started as a getaway trip turned into a life decision when his wife suggested they consider staying, drawn by the low cost of living, the beauty of the landscape, and the manageable access to El Paso's airport.Rob's ability to keep touring economically viable comes from decades of fostering direct relationships with festival directors and venue operators in Europe, combined with a deliberate decision to streamline his setup so he can travel with everything as carry-on luggage.He describes his financial philosophy as doing the work because he loves it and being grateful that it also pays, rather than doing it for money — a distinction he holds with genuine pride, even as he acknowledges the life it produces is a modest one.Rob has kept his overhead deliberately low in Marfa, prioritizing spending on quality food, a reliable car for the long drive to the airport, and little else — a conscious trade-off that has allowed him to sustain a creative life without significant financial stress.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Rob's websiteRob's label

    1h 11m
  4. When Your Bank Account Stops Making Sense

    Jun 8

    When Your Bank Account Stops Making Sense

    Most people with unconventional careers started out with a simple financial dashboard: one look at the bank account told them everything they needed to know. But over time, as careers grow and income gets real in a new way, that single number stops telling the whole story. Tim walks through what happens when the bank account stops making sense: why leaving too much money sitting in cash trades short-term security for long-term growth, and how to think about matching your money to its actual purpose, whether that's immediate spending, a stability cushion, or longer-term investments in stocks and bonds. It's a practical framework for the moment when you've stopped just surviving and started building something real. One Key Takeaway: When your bank account stops making sense, that's not a problem — it's a signal. It means your financial life has grown beyond what a single number can capture, and it's time to start thinking differently. Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.

    9 min
  5. Mary Lattimore — Musician

    Jun 1

    Mary Lattimore — Musician

    In this episode, Tim sits down with Mary Lattimore — classically trained harpist, solo recording artist, and film composer — for a candid conversation about building an unconventional life in music. Mary traces her path from growing up around the harp in Asheville, through years of juggling multiple part-time jobs in Philadelphia, to the Pew Fellowship that gave her the financial breathing room to focus on music full time. She talks openly about her complicated relationship with money: the anxiety that came with her first large sum, the difficulty of saving when income ebbs and flows, and the game-changing decision to hire a business manager who helped her get her finances under control. Mary also shares the story of co-purchasing an apartment in a tiny village in Tuscany, what it felt like to sign those papers, and why owning a little piece of the world somewhere beautiful felt like a dream she barely knew she was allowed to have. Mary's question for Tim: What's your advice for someone whose money ebbs and flows and who is bad about saving? Key Takeaways: Mary describes herself as both a freelance musician and a small business owner — that distinction matters, since thinking of her work as a business has shaped how she manages income, taxes, and team-building.The Pew Fellowship she received in 2014 was the turning point that allowed her to stop working multiple part-time jobs and focus on music full time, though she recalls that seeing her bank account full for the first time actually triggered anxiety rather than relief.Her path out of classical music into her own solo work was gradual and social — friends in Philadelphia asking her to add harp to their records, followed by touring with Thurston Moore, whose mastery of free improvisation pushed her to trust her own musical instincts.Mary co-purchased an apartment in a village of 200 people in Tuscany — splitting the cost and the schedule with a friend — and describes it as a dream she barely believed was possible, especially given that homeownership in the U.S. feels out of reach.Her business manager helped her set up LLCs for both her business and her Tuscany apartment, put her on a regular payroll through her S corp, and helped her make sense of the complex label statements she had previously found overwhelming.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Mary's websiteMary's IG

    46 min
  6. What Money Can’t Buy You

    May 25

    What Money Can’t Buy You

    You know what they say about money & happiness — but we all still want to try a little bit, right? In this solo episode, Tim shares a personal story from his touring career: the year he made the most money he'd ever made as an audio engineer, stayed in nice hotels, and ended up feeling ... deeply unhappy. What was missing was human connection, the sense of being part of a team, the feeling that the work actually mattered — and money is a poor substitute. That realization didn't just change how Tim thought about money; it directly led to the career he has now, built around helping people with unconventional careers use their money to support the lives they actually want to live. One Key Takeaway: More money is swell, but it's not really the goal. The goal is a fulfilling life, and money is just one tool for building it. Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.

    13 min
  7. Cheetie Kumar - Chef & Owner (Ajja & Big Cat)

    May 18

    Cheetie Kumar - Chef & Owner (Ajja & Big Cat)

    In this episode, Tim sits down with Cheetie Kumar — chef, owner of Ajja and Big Cat in Raleigh, NC, and two-time James Beard Award nominee — for a wide-ranging conversation about what it looks like to build a life and a business from scratch with more passion than experience. Cheetie traces her path from immigrating to the US as a child, through punk rock and bartending, to opening a music venue and eventually a restaurant with no formal training. She speaks candidly about the financial blind spots that nearly derailed her early restaurant — underpricing her menu, not understanding cost of goods, and spending years without a real grasp of finances. She also reflects on the emotional weight of growing up with financial insecurity and how that shaped her relationship with money through the present day. Throughout the conversation, Cheetie brings the same thoughtful, collaborative ethos she applies in the kitchen to questions about entrepreneurship, financial literacy, and what it means to build something that reflects your values. Cheetie's question for Tim: What are five essential financial literacy elements for a first-time small business owner? Key Takeaways: Cheetie describes herself first as someone who fixes problems: the reality of running multiple restaurants is that the job is mostly about solving whatever is in front of you.Her path to being a chef was indirect: she was bartending to support her touring life when a lease on a real restaurant space presented the opportunity to start her own restaurant, and she learned how to do that entirely on the job.The DIY ethos of punk rock deeply shaped how she approached opening her first venue and restaurant — not waiting for permission or credentials, but simply identifying what was missing and building it herself.Cheetie shares how not taking on outside investors meant keeping full ownership so that no one else had a claim on what she built, even when that made things harder in the short term.She now approaches finances with diligence and rigor — tracking expenses, reconciling regularly, and understanding that there is no substitute for staying on top of the numbers, because looking away even briefly can put you in the red.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Cheeti's IG accountAjjaBig Cat on Brookside

    52 min
  8. Getting Your Financial House In Order

    May 11

    Getting Your Financial House In Order

    Most people's financial lives are spread across a patchwork of accounts, loans, insurance policies, and retirement funds — some forgotten, some incomplete, some never quite dealt with. Getting your financial house in order means bringing all of it together in one place so you can finally see the whole picture. Tim walks through the process he uses at the start of every financial planning engagement: gathering all of your important financial information, reviewing it to make sure the details are accurate and complete, and then evaluating how the pieces fit together using a series of financial scores that show where things stand right now. Because before you start making plans for the future, you need a clear, honest baseline for where you are today. One Key Takeaway: You can't make a plan for where you're going if you don't know where you are right now. Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.

    15 min
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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
    67
  • Rating
    Explicit
  • Copyright
    © 2026 Timothy Iseler

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