Shows
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