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 Takeaways It always feels like a risky t...
Aug 18, 2025•16 min•Ep. 22
Christian 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, ...
Aug 11, 2025•1 hr 9 min•Ep. 21
The 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 takeaways Recessions are unpredictable but inevitable. An emergency fund with at least 3–6 months of essential spending helps you avoid taking on extr...
Aug 04, 2025•11 min•Ep. 20
Mikael 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 &a...
Jul 28, 2025•1 hr 23 min•Ep. 19
This 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 thos...
Jul 21, 2025•9 min•Ep. 18
Lara 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 takeaways Lara is the co-owner o...
Jul 14, 2025•56 min•Ep. 17
While 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 Takeaways A conventional retirement of leisure is swell, but not everyone will get there – or even wants to But all of us c...
Jul 07, 2025•11 min•Ep. 16
Matt 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...
Jun 30, 2025•56 min•Ep. 15
How 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 e...
Jun 23, 2025•11 min•Ep. 14
Rebecca 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 ha...
Jun 16, 2025•1 hr 7 min•Ep. 13
Managing 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. ...
Jun 09, 2025•15 min•Ep. 12
Adam 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 busin...
Jun 02, 2025•1 hr 11 min•Ep. 11
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:...
May 26, 2025•15 min•Ep. 10
Franz 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 ind...
May 19, 2025•44 min•Ep. 9
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 i...
May 12, 2025•12 min•Ep. 8
John 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 wi...
May 05, 2025•1 hr 1 min•Ep. 7
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 info...
Apr 28, 2025•11 min•Ep. 6
Jeremy 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 extensiv...
Apr 21, 2025•49 min•Ep. 5
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 panic Before you even get to thinking about investments, prioritize saving more money and paying off debt When the stock market tanks, it means you can buy so...
Apr 14, 2025•15 min•Ep. 4
Ivo 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 y...
Apr 07, 2025•58 min•Ep. 3
Money 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....
Mar 31, 2025•6 min•Ep. 2
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 ...
Mar 20, 2025•3 min•Ep. 1
