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 have a collection of low dollar IRAs from jobs I held, short term or part time. What should I do with them?

Key takeaways:

1. Rebecca joined her first band, The Minders, after moving to Denver and connecting with members of the Elephant 6 music collective.
2. Rebecca moved into crew work (merch seller, assistant tour manager) to support her musical lifestyle. She was drawn to it as a job that allowed flexibility, travel, and self-employment—prioritizing control over her time to continue playing music.
3. Encouraged by colleague Dave Burton, Rebecca gradually transitioned into tour managing, gaining early experience with The Head and the Heart and eventually stepping up with Neutral Milk Hotel.
4. Initially hesitant to pursue tour management, Rebecca now embraces the role, striving to make tours better through her experience and leadership. She emphasizes comfort and morale on the road, even if it means spending a bit more.
5. She now balances being a touring musician (playing with Pavement and Pedro the Lion) and a tour manager, often shifting roles depending on opportunities. Rebecca describes choosing between financial stability and meaningful musical opportunities, such as turning down a lucrative tour management gig to play keys with Pedro the Lion.

Links:
Send me a question to be answered on a future episode.
Sign up for the Keep It Easy newsletter.
Rebecca's Insta
The Minders Wiki, Bandcamp, & Insta
Wild Flag

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.
The cash flow equation is income = spending + saving. You can use any part of that equation to improve your cash flow.
Saving a lot of money makes the other parts of cash flow easy.
You can use a target maximum checking account balance to quickly let you know when to save and when to pump the brakes on spending.
A one-month spending fast is an easy way to reset your spending expectations and save money.

Links:
Send me a question to be answered on a future episode.
Sign up for the Keep It Easy newsletter.
Sign up for weekly Office Hours.
Easy Budgeting: 50/30/20 Budget
Foundational Money Habits 2: Saving

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 business side of things, and much more. Adam's question for me: In these times of increasing disparity, deregulation and corporate takeovers what do you think is the best advice for people to gain security and investments who aren't already "making it" or have savings in place? 

Quick correction to the intro: we recorded MBD's first album in early 2002, not 2003. Whoops!

Key takeaways:

1. Adam shares how his band formed in college, gained a dedicated following, and sustained a 20+ year career through consistent touring and strong fan engagement.
2. He details the logistics and emotional intensity of life on the road, from small clubs to selling out large venue.
3. During the pandemic, Adam and his wife opened Pizza Lupo in their hometown of Louisville KY. Adam shares how they pivoted during the pandemic to survive and make the business stronger.
4. Adam shares the importance of understanding the business side of being a bandleader and the responsibility he feels to both bandmates and crew.
5. He talks about how the support of fans drives decisions on what merch to create, playing unique venues (like The Stanley Hotel, featured in The Shining), and how he runs the band's mail order business.

Links:
Murder By Death's website
Pizza Lupo in Louisville KY
Murder By Death's debut album, recorded by yours truly. I wish I had included more close mics from the drums, but am otherwise happy with it.
Send me a question to be answered on a future episode
Sign up for the Keep It Easy newsletter

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 comes to income, profits, or liability.
• LLCs offer liability protection between owner(s) and business, but they don't change your tax treatment. LLC members get taxed the same way as sole proprietors & partners.
• The S-Corp Election allows LLCs to be treated as S-Corps for tax purposes. That means you can treat yourself as an employee and pay yourself a salary.
• The remaining non-salary profits avoid employment tax when they flow from an S-Corp to shareholders, but do not avoid income tax.

Links
Send me a question to be answered on a future episode.
Sign up for the Keep It Easy newsletter.
Sign up for weekly Office Hours.
The IRS site on S-Corps

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 industries, and more. Franz's question to me: What's the best way for freelance musicians to think about retirement funds?

Key points

1. Franz discusses his early experiences in music, influences, and what led him to pursue a career in the industry.
2. How his solo work differs from his band experiences, and the creative freedom it allows him.
3. His involvement in teaching and mentoring students in the music and writing fields.
4. Stories from the road, including memorable performances and the impact of touring on his artistic growth.
5. Advice for aspiring musicians or writers looking to break into a scene.

You can learn more at Franz's website or sign up for his newsletter pianofighter.substack.com.

Ask me a question to be answered in a future episode.
Sign up for the Keep It Easy newsletter.

Thanks!

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.

Key Takeaways:

• Self-employment tax serves the exact same purpose as FICA. It’s not an extra tax on self-employed people; it’s a replacement for the tax that traditionally employed people pay.
• When you’re self-employed, you pay both the employer and employee halves of employment tax. The employer half counts as a deduction for income tax purposes, but you still have to pay it.
• If you’re a sole proprietor, partner in a partnership, LLC member, or freelancer, the only way to reduce self-employment tax is to reduce net profits.
• And finally, while everyone loves saving on the ol’ income tax bill, sometimes writing off a bunch of expenses means less money in your pocket now and less access to Social Security and Medicare benefits later.

Links
Send me a question to be answered on a future episode.
Sign up for the Keep It Easy newsletter.
The IRS webpage for Self-Employment Tax
The IRS Tax Withholding Estimator
Blog post: What's Up With Self-Employment Tax?

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 with touring. John's (tongue-in-cheek) question for me: we're in for four years of markets responding to things posted on social media by political actors. what long positions will give the highest yields in such a volatile environment? Hooboy, let's see how I do with that one!

Key takeaways:

1. John  reflects on his early life and the development of his musical career. He mentions how creating music often started as a hobby before becoming more serious.
2. He talks about his shift from making music to writing novels, stressing the importance of doing something that feels true to oneself.
3. John shares insights about balancing art creation with financial pressures.
4. He recounts the financial struggles of his early career and how those experiences shaped his commitment to his creative work.
5. John emphasizes the importance of maintaining integrity in both his music and writing, and that financial success should never be prioritized over artistic satisfaction.

Links:
The Mountain Goats
John's page at MacMillan Publishers

Ask me a question to be answered in a future episode.
Sign up for the Keep It Easy newsletter.

Thanks!

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 like to be and then start making decisions that fit with that self-image.

Links
Send me a question to be answered on a future episode.
Sign up for the Keep It Easy newsletter.
Are You "Good At" Money?
The Robert Rodriguez interview mentioned in this episode
James Clear's Atomic Habits

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:

1. Jeremy  discusses his extensive experience as a touring audio engineer.
2. He reflects on the differences between working in studio recording versus live sound, highlighting the adaptability required on the road.
3. Jeremy talks about collaborating with musicians and the importance of understanding their sonic preferences.
4. Jeremy recounts stories of working with well-known artists and the unique dynamics of touring with different personalities.
5. He emphasizes the importance of professionalism, preparation, and communication in the world of live sound.

Jeremy's woefully out-of-date website
Jeremy's Discog's page

Ask me a question to be answered in a future episode.
Sign up for the Keep It Easy newsletter.

Thanks!

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 something valuable at a discount to what it cost a few months ago.

Links:

What The Hell Is Going On (And What Should You Do)

Ask me a question to be answered in a future episode.

Sign up for the Keep It Easy newsletter.

Related articles:

A Tale Of Two Markets

Another Recession Is Coming. How Should You Prepare?