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: 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.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.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.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.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 HoursSend me a question to be answered on a future episodeSign up for the Keep It Easy newsletterThe mortgage calculator I used for the examplesThe NYT chart of U.S. home prices (adjusted for inflation) 1890-2006Investopedia – Has Real Estate or the Stock Market Performed Better Historically?
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Sam Kassirer - Musician & Producer
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 me: Could you define or describe the term investing without using the word money?Key takeaways:Sam describes his early path studying music, playing keys, and taking on “general business” (wedding/cover) gigs before moving toward touring and studio work.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.Sam founded and operates The Great North Sound Society, a residential recording studio in a farmhouse in Maine. 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.Sam shares practical money habits—like small, automatic daily transfers into savings—as a way to build great financial health. LinksSend me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Great North Sound SocietyJosh Ritter's websiteMagic Mugzz, Sam's Instagram account of mugs he sells for charity
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When 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: 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.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.Sometimes the biggest need is perspective—a second opinion to answer “am I doing okay?” and provide clarity on savings, debt, or priorities.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.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 HoursSend me a question to be answered on a future episodeSign up for the Keep It Easy newsletter
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Brad Cook - Record Producer
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 me: 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: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.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.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.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.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.LinksSend me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Brad's websitePhil Cook's websiteMegafaunBon IverThe new Mavis Staples single that Brad producedPaul Voran's IG
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Is 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, 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.LinksSend me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter
The Thing We Never Talk About is an educational podcast about personal finance for creatives and other weirdos. We'll discuss managing cash flow with a lumpy income, when to save & when to invest, and how to reduce stress & build confidence when it comes to your money. No hot stock tips, no complicated strategies, and no finance bro jargon. We'll hear from artists, musicians, creative professionals, and other weirdos about how they navigate these questions for themselves. The Thing We Never Talk About is hosted by Timothy Iseler, CFP®, a former recording & touring audio engineer with 18 years experience in the music industry.
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