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 takeaways:

1.  Buying a primary residence is not technically considered an investment because it is purchased for personal use (rather than to generate income). For this discussion, though, let's set aside the technical definition and evaluate buying a home as if it were an investment.
2. Investment comparisons must be made against alternatives; here, the U.S. stock market is used as the benchmark. Using a $500k home with a $100k down payment, 6% mortgage APR, and 6% annual appreciation, we compare the 10-year returns to stock market investing.
3. Under these assumptions, the home sale produces ~44.6% ROI, while stock investments yield ~121.7% ROI, showing the stock market as the stronger performer. But there are other financial benefits to owning a home besides the sale price.
4. Home ownership does provide tax advantages: mortgage interest deductions and capital gains exclusions for primary residences. There's also access to money through home equity loans & lines of credits. And long-term benefits include lower relative housing costs relative to inflation & the potential for generational wealth transfer.
5. Conclusions: short-term home buying as a “step-up ladder” is a poor investment, but long-term ownership (15–30+ years) can make a lot of financial sense.

Links:
Sign up for weekly Office Hours
Send me a question to be answered on a future episode
Sign up for the Keep It Easy newsletter
The mortgage calculator I used for the examples
The NYT chart of U.S. home prices (adjusted for inflation) 1890-2006
Investopedia – Has Real Estate or the Stock Market Performed Better Historically?

Sam 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 music and life.

Sam's question for Tim: Could you define or describe the term investing without using the word money?

Key takeaways:

1. Sam describes his early path studying music, playing keys, and taking on “general business” (wedding/cover) gigs before moving toward touring and studio work.
2. A long-running collaboration with Josh Ritter became a central pillar of his career, including extensive touring and recording with Josh and The Royal City Band.
3. Sam founded and operates The Great North Sound Society, a residential recording studio in a farmhouse in Maine. 
4. He shares his thoughts on how to charge for his own time, as well as what to pay the musicians he hires to play on records.
5. Sam shares practical money habits—like small, automatic daily transfers into savings—as a way to build great financial health. 

Links
Send me a question to be answered on a future episode.
Sign up for the Keep It Easy newsletter.
Great North Sound Society
Josh Ritter's website

Magic Mugzz, Sam's Instagram account of mugs he sells for charity

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:

1. Try it yourself first: pick one financial goal, give yourself a three-month deadline, and see if you can make progress without help. If so, great! If not, that’s a good sign you’d benefit from an advisor.
2. A financial advisor can add value when your circumstances improve, such as a higher income, inheritance, or sudden windfall, and you want to make smart decisions.
3. Sometimes the biggest need is perspective—a second opinion to answer “am I doing okay?” and provide clarity on savings, debt, or priorities.
4. Investment management isn’t for everyone—some people love doing it themselves—but if you find it overwhelming or uninteresting, having a professional handle it may be worthwhile.
5. There’s no right or wrong choice when it comes to deciding if you should work with an advisor. Just like DIY home projects, some people enjoy managing money themselves while others prefer to look for outside help. The key is choosing what works best for you.

Links:
Sign up for weekly Office Hours
Send me a question to be answered on a future episode
Sign up for the Keep It Easy newsletter

Brad 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 the ways that emerging technologies will disrupt both financial advise and the music industry.

Brad's question for Tim: there are so many conversations surrounding music and ai. What are your thoughts on the future of financial planning and investing in regard to AI and blockchain technology?

Key takeaways:

1. Brad started playing music with his brother Phil & pal Justin Vernon (who later started Bon Iver) in Wisconsin, where they all grew up. They later moved to Raleigh NC and, after that band broke up, Brad & Phil started Megafaun with their friend Joe Westerlund.
2. One of the biggest tasks he takes on as a producer is to help artists get over mental & emotional blocks so they can make the records they want to make. If he can help an artist make a record that's true to the their vision, Brad considers it a success.
3. Brad works with all kinds of bands, big & small, new & established. Some records make money, some don't, but he trusts in the process and believes that if he can consistently help people make great work, the money side will work itself out.
4. Working with a consistent engineer, Paul Voran, over the last several years has allowed Brad to be more objective than in the past when he was handling more technical aspects of recording. That gives him the space to help artists get comfortable and start making music right away, knowing that Paul is there to help facilitate the rest.
5. We talk about the roles of AI and blockchain technology in both music & the financial industry. Brad sees an opportunity for significant disruption of the publishing & royalty collection side of the music business once more modern, automated contracts become the norm.

Links
Send me a question to be answered on a future episode.
Sign up for the Keep It Easy newsletter.
Brad's website
Phil Cook's website
Megafaun
Bon Iver
The new Mavis Staples single that Brad produced
Paul Voran's IG

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 time to invest, while simultaneously feeling like the past was a better, safer time to invest. The irony being that the past also felt risky when it was the present.
• History shows that even the “worst” times often lead to strong long-term growth.
• Waiting until it feels safe to invest usually means missing out—the feeling of uncertainty never fully goes away.
• Invest when you have the money, not when the headlines are favorable.
• You can reduce stress by investing gradually (e.g., monthly contributions), balancing risk through diversified investments, and choosing investments that you can own for a long, long time.

Links
Send me a question to be answered on a future episode.
Sign up for the Keep It Easy newsletter

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, composing for theater & dance, and how he made the decision to start working at MIT.

Christian's question for Tim: how are you making your coffee these days?

Key takeaways:

1. Christian trained as a classical violist at Juilliard before shifting his creative focus toward contemporary composition and performance.
2. He was a founding member of the instrumental group Rachel’s, which blended classical and rock influences, offering a formative space for collaboration and exploration.
3. Christian also composes for theater and dance, including sound design.
4. He discusses the challenge of making a living through creative work and shares how freelance work requires both flexibility and resilience.
5. He reflects on how curiosity and collaboration have driven big career decisions throughout his life.

Links
Send me a question to be answered on a future episode.
Sign up for the Keep It Easy newsletter.
Christian's website
Rachel's on Touch And Go's website
SITI Company
Palissimo
The coffee roaster I use (now discontinued): FreshRoast SR 500
Sweet Maria's, a great source for green coffee beans

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 extra debt or selling investments at the worst time.
• Pay down high-interest debt (like credit cards and personal loans) helps reduce vulnerability during income disruptions.
• Understanding what spending is essential vs. optional can help you act quickly and confidently when you need to pull back on spending.
• Match your investments to your timeline & risk tolerance so you're less likely to panic and sell when markets drop.

Links
Send me a question to be answered on a future episode.
Sign up for the Keep It Easy newsletter
Investopedia article on recessions

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 & down income of a musician. If you’re self-employed and looking for actionable ways to improve your financial health, I think you’ll find some really useful takeaways from this conversation.

Mikael's question for Tim: what is your strategy for dealing with the erratic and sporadic income streams for musicians? 

Key takeaways:

1. Mikael's professional journey began in earnest after moving to Chicago, where he worked as an audio engineer at Soma Electronic Music Studios and built relationships in the local music scene.
2. After engineering Down With Wilco by The Minus 5, Mikael was hired to engineer what became Wilco's album A Ghost Is Born. Through the process of making that record, he moved from working behind the glass as an engineer to playing with the band and eventually becoming a full member of Wilco.
3. He discusses the unpredictable nature of income in music, noting how touring, sync licensing, and how your income gets taxed all contribute variably to financial stability.
4. Mikael talks about living modestly and his techniques for managing cashflow with an up & down income.
5. He also shares how he got started investing and how, even with a relatively conservative investment mix, he has managed to grow his money in meaningful way after years of sticking with it.

Links
Send me a question to be answered on a future episode.
Sign up for the Keep It Easy newsletter.
Mikael's website
Mikael's Patreon
Mikael's documentary on Bob James
Wilco's website
John McEntire's website
Isotope 217 "Who Stole The I Walkman?"
The Minus 5 "Down With Wilco"
Michael Azerrad's "The Amplified Come as You Are: The Story of Nirvana"

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 those contributions so that you can pay your future self the same way you would any other essential bill. It’s a practical, no-guilt approach to taking care of future you, starting with whatever you can manage today.

Key takeaways

• Pay yourself first—treat savings like a non-negotiable expense, just like rent or utilities.
• Break big goals into small steps: $7,000/year is about $583/month, $135/week, or $19/day.
• Automation is your best friend for consistent saving—remove willpower from the equation.
• Start where you are—even saving $10/day adds up to over $3,600 a year, and progress matters more than perfection.

Links
Send me a question to be answered on a future episode.
Sign up for the Keep It Easy newsletter.

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 Tim: Where should we be saving money right now for midterm goals like a home remodel?

Key takeaways

1. Lara is the co-owner of Farmscape, the largest urban farming company in the U.S.
2. Her background is in audio engineering and stagehand work. Before fully launching into urban farming, Lara juggled multiple jobs—including working as a housekeeper, delivering produce, and running a farm stand—to explore different paths and support herself.
3. Lara and her team built a company many thought couldn’t work, navigating self-doubt, limited formal business education, and a steep learning curve with persistence and creativity.
4. While working as a housekeeper, Lara received transformative investing advice from a client who taught her how to open an IRA, invest in mutual funds, and understand compound interest. She once viewed investing with skepticism but now sees it as essential—especially for financial empowerment for women.
5. At Farmscape, she champions employee financial health by offering a 401(k) with matching and encourages investing through relatable, experience-based education.

Links
Farmscape
Just Keep Buying by Nick Maggiulli
Send me a question to be answered on a future episode.
Sign up for the Keep It Easy newsletter.