Shows
The Thing We Never Talk AboutTodd Trainer - Drumming InstructorDrumming 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 push...
2025-12-2950 min
The Thing We Never Talk About4-Week Financial DetoxHoliday 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...
2025-12-2217 min
The Thing We Never Talk AboutRandy Randall – Musician, Podcaster, & Freelance MarketerIn this wide-ranging & deeply reflective conversation, guitarist Randy Randall (No Age, Hyphenate with Randy Randall) talks about the shifting economics of indie music, redefining success as he became a parent, and building a freelance career in marketing almost by accident. From his early days immersed in the DIY community to learning resilience in the gig economy, Randy shares an honest, unglamorous, and strangely hopeful portrait of what it means to be a lifelong creative worker. He & Tim dig into the real tensions between art and money, how freelancing in marketing actually aligns with his long history of conceptual art...
2025-12-151h 40
The Thing We Never Talk AboutEasy Cash Flow: What's Your “Invisible Number”?In this episode, Tim explains why cash flow is the foundation of every financial plan — and introduces a simple technique to make saving money easier and more consistent. By identifying your “invisible number,” the small amount you can save automatically without ever noticing, you can improve your cash flow, build long-term security, and reduce friction in your financial life. Tim breaks down how this approach works, why automation matters, and how small, steady habits can quietly transform your financial trajectory.5 Key Takeaways:Cash flow is the foundation of financial planning. Every major financial decision — investing, buying a home...
2025-12-0813 min
The Thing We Never Talk AboutMax Goldblatt – Film & Video EditorFilm and video editor Max Goldblatt joins Tim to talk about building a creative career across indie films, digital content, and nearly a decade of touring. He shares how early exposure to editing shaped his path, how short-film work opened doors to feature projects, and what it takes to balance passion, stability, and financial responsibility in an unpredictable industry. Max also reflects on navigating rate negotiations, imposter syndrome, and the realities of sustaining creative momentum over time.Max's question for me: My kid is three. School is expensive. I know that a 529 plan has some limitations, like wh...
2025-12-011h 14
The Thing We Never Talk About5 Tips To Save On Next Year’s Tax BillAs the year winds down, Tim shares five practical steps you can take right now to lower next year’s tax bill. From maximizing retirement contributions to understanding energy-efficiency credits, this episode focuses on simple, actionable strategies for creative professionals and self-employed listeners. Tim breaks down how tax-deferred accounts, health savings accounts, and even small investment decisions can make a meaningful difference — without the last-minute stress of filing season. Five Key Takeaways:Contribute to tax-deferred retirement accounts. Deposits into IRAs, 401(k)s, and similar accounts reduce current-year taxable income. Remember: new accounts must be opened before Decem...
2025-11-2415 min
The Thing We Never Talk AboutJohn Dugan - Content Specialist in the Design IndustryIn this episode, Tim talks with writer, drummer, and content specialist John Dugan about creative work, shifting career priorities, raising kids in a music-rich environment, and how financial needs and perspectives evolve over time. John reflects on decades in bands including Chisel, his transition from journalism into content strategy for the design world, and what happens when art, family life, and money all need to coexist. They also discuss saving habits, risk tolerance, reunion shows, and supporting the next generation of artists—including John’s teenage son’s band, Uniflora.John's question for me: why would someone invest...
2025-11-171h 02
The Thing We Never Talk AboutListener Mailbag 01It's the first listener mailbag episode! Tim answers real money & personal finance questions from listeners about ethical investing, managing debt, and overcoming money-related shame. He explains how to easily invest according to your values, how to balance saving while paying off student loans, and when to use savings to tackle credit card debt. The conversation ends with a thoughtful reflection on emotional well-being — how to move past financial shame and build confidence through small, consistent wins.Key Takeaways:Ethical investing is more accessible than ever. Lower cost ESG & SRI funds allow everyday investors to align their mo...
2025-11-1028 min
The Thing We Never Talk AboutBenjamin Percy – StorytellerBenjamin Percy has built a career bridging literary fiction, comics, and Hollywood storytelling. As the author of acclaimed novels, comic book arcs for Marvel and DC, and scripts for film and audio drama, Ben joins Tim to discuss the craft and discipline behind a self-employed creative life. He talks about writing routines, handling rejection, learning to navigate the business side of art, and balancing creative ambition with family life. The conversation explores how consistency, humility, and persistence turn creative work into a sustainable career. Ben's question for me: AI worries me for all the standard reasons, but i...
2025-11-031h 05
The Thing We Never Talk AboutQuick Nest Egg CalculationWhat would it take for work to become optional? In this solo episode, Tim walks through a simple framework for estimating your “enough” number—the amount you’d need in savings & investments to reduce or even eliminate the obligation to work. Using the 4% and 25× rules, he explains how to calculate a target nest egg amount, why it’s useful even if you never plan to retire, and how small, consistent habits can turn into huge long-term growth over time. Whether your dream is full retirement or just the freedom to choose when & how you work, this episode offers clear & practical in...
2025-10-2716 min
The Thing We Never Talk AboutMichael Perry - Self-Employed WriterFor more than 30 years, Michael Perry has built a life around words — from essays and bestselling books to one-man shows and live events. In this conversation, Mike shares how his blue-collar roots shaped his approach to creative work and money, why he still keeps his nursing license “just in case,” and what it really takes to sustain a self-employed creative life. He and Tim talk about saying no to the wrong opportunities (even when Oprah calls), learning business skills on the fly, and how low overhead, multiple income streams, and a willingness to keep “shoveling” have allowed him to keep doing...
2025-10-201h 18
The Thing We Never Talk AboutWhat Is “Wealth”?What comes to mind when you hear the word “wealth”? In this episode, Tim explores how our ideas about money are shaped not just by math & spreadsheets, but by deep emotional lessons from family, culture, and experience. He unpacks why textbook definitions of wealth often fall short, shares perspectives from author Morgan Housel, and offers a new way to think about building abundance: creating more “perfect average days”. Along the way, Tim explains how saving and investing can buy you freedom, time, and peace of mind—keys to living a life of true wealth.Key takeaways:Wealth is...
2025-10-1315 min
The Thing We Never Talk AboutSam Ratto - Chocolate MakerSam Ratto is the founder of Videri Chocolate Factory in Raleigh, NC, and recently started Golf Golf Golf, an indoor golf simulator business. In this episode, Sam shares his winding path from surfing & skateboarding culture, launching a bean-to-bar chocolate company, and building a new hospitality venture around his love of golf. He talks about the realities of small business finance, lessons learned from failures, and how he balances entrepreneurial risk with personal stability. One key takeaway: The creative path to entrepreneurship isn’t linear—financial discipline and resilience help make bold risks possible.Sam's question for me: what...
2025-10-061h 14
The Thing We Never Talk AboutThe Problem With Too Much CashIn this episode, we unpack why having the right amount of cash in savings is essential—but why holding on to too much can quietly hurt your financial future. While an emergency fund provides short-term stability and peace of mind, excess cash loses value every year to inflation. By contrasting the short-term safety of savings with the long-term growth of investments, the conversation highlights the importance of balance. Practical frameworks like the “barbell model” and simple steps for gradually investing extra funds show how to move beyond just saving to start building lasting financial security.Key takeaways:Aim...
2025-09-2915 min
The Thing We Never Talk AboutMacie Stewart - MusicianMusician Macie Stewart has been performing since her teens, from early bands like Kids These Days to co-founding Finom & becoming a fixture in Chicago’s improvised music scene. In this episode, she talks about finding community at Constellation (an excellent Chicago venue), balancing the realities of freelance income with creative freedom, and what success looks like for her today. One key takeaway: building a sustainable creative life means balancing financial practicality with artistic curiosity and community.Macie's question for me: how to make a yearly budget when income fluctuates so greatly? Key takeaways:Macie beg...
2025-09-221h 13
The Thing We Never Talk AboutIs Buying A Home A Good “Investment”?Buying a home is often called “the best investment you’ll ever make”—but is that really true? In this episode, Tim breaks down what it means to think of a primary residence as an investment, comparing real estate returns to long-term stock market performance. Using real numbers, historical data, and examples, he highlights the risks, tax benefits, and long-term advantages of homeownership while challenging some common assumptions. Whether you’re considering buying your first home or wondering about the financial trade-offs, this episode offers a clear-eyed perspective on when (and how) owning a home makes sense.Key takeaw...
2025-09-1531 min
The Thing We Never Talk AboutSam Kassirer - Musician & ProducerSam Kassirer is a musician, producer, and the founder of The Great North Sound Society, a residential recording studio in rural Maine. In this episode, he talks about his path from gigging pianist to touring with Josh Ritter and building a creative retreat where bands can record together under one roof. Sam shares practical insights about balancing art and money, including how he structures rates, handles the realities of freelance income, and maintains sustainability over time. He also reflects on the lessons learned from years of touring and recording, and how those experiences continue to shape his approach to...
2025-09-081h 04
The Thing We Never Talk AboutWhen Do You Need A Financial Advisor?In this episode, we explore the question of when it actually makes sense to work with a financial advisor. Sometimes you already know what needs to be done—you just need accountability or a new perspective to make it happen. Other times, big changes in income, unexpected windfalls, or simple uncertainty about “am I doing okay?” make professional guidance valuable. The conversation emphasizes that not everyone needs an advisor, but if you feel stuck, overwhelmed, or uninterested in managing the details yourself, reaching out could be the right next step.Key Takeaways:Try it yourself first...
2025-09-0113 min
The Thing We Never Talk AboutBrad Cook - Record ProducerBrad Cook is a record producer based in Durham NC. Although he has been a professional musician & artist manager in the past, Brad has focused on production full-time for the last seven years. He has produced dozens of records since then, working primarily from his home studio. And he's one of my best friends! Brad and I became pals when we both toured with Sharon Van Etten back in 2014-15 (Brad played bass, I was front of house audio engineer & tour manager). This conversation covers all kinds of ground, from production to the real value of financial advice to t...
2025-08-251h 21
The Thing We Never Talk AboutIs This A Good Time To Invest?In this episode, we dig into one of the most persistent investing dilemmas: knowing when the “right time” to invest actually is. Through personal stories and historical examples, we explore why the market always feels risky in the present—even though the biggest long-term gains often come to those who invested during turbulent times. The message is simple but powerful: the best time to invest is when you have the money, not when the market feels calm.Key TakeawaysIt always feels like a risky time to invest, while simultaneously feeling like the past was a better...
2025-08-1816 min
The Thing We Never Talk AboutChristian Frederickson - Composer & Sound DesignerChristian Frederickson is a composer, violist, and sound designer whose career has bridged the worlds of classical music, experimental performance, and theater. In this episode, we talk about his transition from conservatory-trained musician to co-founder of the influential instrumental group Rachel’s, and his later work composing and designing sound for stage and dance productions. In this conversation, he shares the origins of Rachel's, how he supported himself when he moved to New York City, composing for theater & dance, and how he made the decision to start working at MIT.Christian's question for me: how are you ma...
2025-08-111h 08
The Thing We Never Talk AboutAnother Recession Is ComingThe next recession isn’t a matter of if but when. While no one can predict the exact timing, there are practical steps you can take right now to make your finances more resilient before the economy takes a downturn. This episode shares four tips that anyone can use to improve financial stability & security to help navigate uncertaintimes.Key takeawaysRecessions are unpredictable but inevitable.An emergency fund with at least 3–6 months of essential spending helps you avoid taking on extra debt or selling investments at the worst time.Pay down high-interest debt (like credit cards and...
2025-08-0410 min
The Thing We Never Talk AboutMikael Jorgensen - MusicianMikael Jorgensen is best known as the keyboard player in Wilco, a position he's held for 20+ years. But before that, Mikael and I were both staff engineers at Soma Electronic Music Studios in Chicago. Mikael shares stories about his dad, who was also a recording engineer, touring & releasing records with his first bands, how he got started at Soma and how he moved from recording Wilco to being part of the band. Plus Mikael shares a ton of really useful information on how he manages the up & down income of a musician. If you’re self-employed and looking for ac...
2025-07-281h 23
The Thing We Never Talk AboutHow To Save An Extra $7k/YearThis episode builds on the previous conversation about how investing $7,000 a year can grow into $1 million. If you’re self-employed or living on a creative income, the idea of setting that money aside might feel impossible—but it’s more doable than you think. By breaking the total into manageable monthly, weekly, or even daily amounts, and comparing it to everyday expenses like dinner out or a movie ticket, that $7k per year target will feel more achievable. And whenever possible, automate those contributions so that you can pay your future self the same way you would any other essent...
2025-07-2109 min
The Thing We Never Talk AboutLara Hermanson - Owner of FarmscapeLara Hermanson owns the largest urban farming company in America. But you wouldn't have guessed it when we played in a band together in our 20s! Lara shares how she started farming as one of many jobs she had just to get by, how she learned about investing while working as a housekeeper, and ways to enjoy life in Oakland CA without spending a lot of money. Lara's question for me: Where should we be saving money right now for midterm goals like a home remodel?Key takeawaysLara is the co-owner of Farmscape, the largest...
2025-07-1455 min
The Thing We Never Talk AboutHow To Turn $7k/Year Into $1 MillionWhile not everyone needs to plan for a conventional retirement, I think that everyone could benefit from saving & investing to increase financial independence – the ability to choose when to work (or not) and with whom. Today's episode looks at how you could grow your nest egg to $1 million by maxing out your IRA and buying the simplest investment options available.Key TakeawaysA conventional retirement of leisure is swell, but not everyone will get there – or even wants toBut all of us can save & invest to increase financial independence: the ability to choose how & when...
2025-07-0710 min
The Thing We Never Talk AboutMatt McCaughan - MusicianMatt McCaughan is probably best known as the drummer for Bon Iver, but he's played with tons of bands big & small both on stage and in the studio. In this conversation, Matt shares how he got started in music, the importance of not being too career-minded too soon, how he thinks about his work & how to price it, and how he manages the ups & downs of a gig-based income. Matt's question for me: I don't really pay attention to or care about cryptocurrency. Should I, and or when should I start paying attention? Key takeawaysMatt's j...
2025-06-3055 min
The Thing We Never Talk AboutPlanning With An Up & Down IncomeHow to you make financial plans for the future when you don't know what you'll make this year or even this month? Today I share three simple tips that people with up & down incomes can use to build financial stability and plan for the future.Key Takeaways:If you know that something will happen – even if that something is unpredictability – you can make a plan for it.Knowing how much you spend each month is essential to building financial stability.Keeping a dedicated cash account as an emergency or opportunity fund allows you to face...
2025-06-2310 min
The Thing We Never Talk AboutRebecca Cole – Musician & Tour ManagerRebecca Cole is a musician and tour manager. She's worked as a roadie for many years, but started playing music with her first band The Minders in the mid-90s and recently toured the world as the keyboard player in Pavement. Rebecca is a delight to speak with and I really enjoyed this conversation about finding room for luxuries on any income, how moving to another city helped her buy a home, the pros & cons of pinching every penny as a tour manager, and more.Rebecca's question for me: I have a collection of low dollar IRAs...
2025-06-161h 07
The Thing We Never Talk AboutLow-Tech Cash FlowManaging cash flow can be a handful for anyone, but especially for people with weird jobs. Cash flow is the money that comes in and the money that goes out, and managing it is fundamental to every other financial decision you make. Today I share three low-tech, super simple techniques that anyone can use at any income level to manage cash flow – and all without the use of a budget.Key Takeaways:Budgeting is great for some people, but for others it can be a lot of work without a lot of payoff.The cash fl...
2025-06-0915 min
The Thing We Never Talk AboutAdam Turla – Musician & Restaurant OwnerAdam Turla is a founding member of the band Murder By Death and co-founder of the Louisville KY restaurant Pizza Lupo (both with his wife, Sarah Balliet). And we go way back – I recorded the band's 2003 debut full-length album over 6 days during their spring break. In this conversation, Adam shares stories from the band's early days, the decision to stop touring after 25 years, how he & Sarah started a restaurant that survived the pandemic, the importance of musicians understanding the business side of things, and much more. Adam's question for me: In these times of increasing disparity, deregulation and corporate ta...
2025-06-021h 11
The Thing We Never Talk AboutLLC or S-Corp?Which business type is better for self-employed people – LLC or S-Corp? This episode takes self-employment tax a step further with a look at the pros & cons of LLCs and S-Corps, including how S-Corps help self-employed people save on employment taxes (but add more complexity and paperwork). At the end, you should understand the basics of sole proprietors, partnerships, LLCs, and S-Corps, and how each of them gets treated by the IRS when it comes to income & employment tax.Key Takeaways:Sole proprietors & partnerships are simple to run, but offer no distinction between owner and business when it...
2025-05-2614 min
The Thing We Never Talk AboutFranz Nicolay – Musician, Author, & TeacherFranz Nicolay's new book, "Band People: Life And Work In Popular Music", is all about how working musicians think about their craft, careers, and compensation – a natural fit for this podcast! He is also a working musician, releasing music & touring under his own name, as a member of The Hold Steady, and co-founder of the composer-performer collective Anti-Social Music. It was a pleasure to speak with Franz about life as a musician in NYC, the differences between the music and publishing industries, and more. Franz's question to me: What's the best way for freelance musicians to think about retirement fu...
2025-05-1944 min
The Thing We Never Talk AboutWhat's Up With Self Employment Tax?The annual tax filing deadline is in the rearview mirror, but if you want to reduce your stress for next year's filing, this is actually the perfect time to start thinking about & planning for next year’s taxes. Today we look at a tax that impacts self-employed people called, cleverly enough, Self-Employment Tax. It impacts all sole proprietors, partners in partnerships, LLC members, freelancers, and anyone with a 1099. I'll explain what self-employment tax is, how it gets calculated, what it means when you're both employer & employee, and the impacts of using lots of write-offs to reduce your taxable income....
2025-05-1211 min
The Thing We Never Talk AboutJohn Darnielle – Musican & AuthorJohn Darnielle is the founder & songwriter of The Mountain Goats, as well as the author of three excellent novels and the 33 1/3 series book about Black Sabbath's classic "Master Of Reality" album. We talk about how he got started in both music & writing, how he managed to stick with music for years despite not really making any money, the decision to pursue music full time, the responsibility he feels to the other members of The Mountain Goats and support staff, and balancing writing with touring. John's (tongue-in-cheek) question for me: we're in for four years of markets responding to things...
2025-05-051h 01
The Thing We Never Talk AboutCase Study: Are You "Good With Money"?What does it take to be "good with money"? Today we look at a real life financial planning case study to show how self-talk and identity factor into making better financial decisions.Key takeaways:You don't need to wait for permission to begin changing your life, even/especially when it's something really important.A key driver in building positive habits is how you self-identify. Identity is at the heart of behavior change.Making good decisions with money is rarely about having perfect information. (Does that ever exist?)Instead, you should decide the type of person you'd...
2025-04-2811 min
The Thing We Never Talk AboutJeremy Lemos – Touring Audio EngineerJeremy Lemos is a touring audio engineer from Chicago. And he's also one of my best friends! Jeremy and I came up in the independent studio world of early 2000s Chicago and have toured together many times. We talk about how he got started in the music industry, how he decides what gigs to take, and the impact of investing over many years. Jeremy's question for me: What advice to you have about the tax burden on your investments and how to lessen them?Key takeaways:Jeremy discusses his extensive experience as a touring audio engineer.H...
2025-04-2148 min
The Thing We Never Talk AboutWhat The Hell Is Going On (And What Should You Do)?Hooooooboy, what’s in the news?!? It’s been totally stressful and fatiguing to follow the wild ups & downs (mostly downs) in the stock market lately. So I thought I’d take a minute to acknowledge a question lots of people are thinking: what the hell is going on, and what should I do?Here’s the TL/DR:Don’t sell your investments out of panicBefore you even get to thinking about investments, prioritize saving more money and paying off debtWhen the stock mark...
2025-04-1414 min
The Thing We Never Talk AboutIvo Gasparotto – Freelance Software DesignerIvo Gasparotto is a software designer who recently started working for himself as a freelancer. And he's one of my oldest friends! Ivo and I were roommates when we moved to Chicago together in the early 2000s and remain good friends to this day. We talk about our early days getting by on very little money, the importance of keeping your spending in check, and the cushion that saving & investing provided when he decided to go freelance. Ivo's question for me: Was there anything that brought you joy so far this year?Key takeaways:Early inspirations...
2025-04-0758 min
The Thing We Never Talk AboutLet's Talk About MoneyMoney is weird, right? It touches almost every part of our lives, from the work we do, to our homes, to where our kids go to school. Money plays a part in pretty much everything, but we don’t really talk about it. Something that impacts nearly every part of our lives should not be so off-limits that it prevents us from moving forward in life. Ok, maybe don’t share your bank account balance on social media – but does it really need to be such a stressful topic? So let’s talk about money.
2025-03-3105 min
The Thing We Never Talk AboutIntroducing...Introducing "The Thing We Never Talk About", a podcast about personal finance for weirdos.What’s the one thing that you definitely, never, ever talk about in polite company? That’s right, money. Not in public, not with your peers, and lots of times not even at home. And, if you're a creative person, money is absolutely the least cool thing you can care about. Creative people are supposed to do what they do because they love it, right?But what about if you actually want to, you know, get ahead a litt...
2025-03-2002 min