The Thing We Never Talk About

In this episode, Tim sits down with Andrew Sandoval — producer, manager, and founder of Beat Land Books — for a wide-ranging conversation about a life built entirely around music fandom. Andrew traces his path from publishing a music fanzine as a teenager to writing liner notes, managing the Monkees on their 50th anniversary tour, and eventually launching a book company producing deluxe, limited-edition volumes for underserved fan communities. Throughout the conversation, Andrew reflects candidly on the financial realities of that kind of career — the feast-or-famine nature of tour income, the experience of subsidizing passion projects with his own savings, and what it's like to have invested so heavily in music that conventional financial planning has largely happened around him rather than because of him. He also shares hard-won lessons about the importance of delegating, finding complementary collaborators, and identifying what's missing in a market rather than chasing what already exists.Andrew's question for Tim: What would be a good first step for someone wanting to dip their toe into the investment market without tying up a lot of liquid income?Key Takeaways:Andrew describes himself as a producer rather than a manager — a title that fit both his creative role and the Monkees' own complicated history with outside representation — though in practice he handled everything from booking flights and negotiating contracts to writing set lists and running video footage during shows.He got his start in the music business by putting himself in the room where things were happening — working at clubs, writing liner notes, showing up and being useful — and credits that approach, more than any formal career plan, with everything that followed.When the pandemic wiped out a major Monkees tour he had been producing, Andrew pivoted to self-publishing — launching a 700-plus page deluxe book on the Monkees by going directly to the fan community he had spent years building, rather than waiting for a publisher or using a platform like Kickstarter.His publishing model is built around identifying underserved audiences and making products that no mainstream publisher would bother with — limited runs, no Amazon, no digital versions, direct-to-consumer fulfillment — because scarcity and quality matter deeply to collectors.Andrew describes music as his religion, and acknowledges that this devotion has shaped his financial life in ways that aren't always practical — including years of subsidizing passion projects with his own savings because the work itself felt worth doing regardless of the return.Links:Send me a question to be answered on a future episode. ( https://www.iselerfinancial.com/podcast )Sign up for the Keep It Easy newsletter. ( https://www.iselerfinancial.com/newsletter )Watch this episode on YouTube. ( https://www.youtube.com/watch?v=FihXte_Gsx8 )Beatland Books ( https://beatlandbooks.com/ )

Most people use the words "investing" and "trading" interchangeably — but they're actually two very different games, and the one you choose to play makes all the difference. Trading takes a lot of work & relies heavily on luck with limited upside. Investing, by contrast, means committing money to things you believe are fundamentally worth owning and holding them long enough for compounding to do the work for you. Tim walks through why trading is so hard to do, why patient long-term investing is far easier than most people assume, and why relying on the financial news media can actually lead you astray if you're trying to build real wealth.One Key Takeaway: Investing — owning good things for a long time — is a game almost anyone can win.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.

In this episode, Tim sits down with Scott Adamson — touring front of house audio engineer and founder of The Production Academy — for a wide-ranging conversation about building a life in live sound. Scott traces his career from mixing indie bands in small clubs to working with Grammy-winning artists in arenas, sharing how luck, relationships, and just sticking around long enough opened doors he couldn't have anticipated. He shares his experience with  the financial realities of the touring world and speaks candidly about The Production Academy, the online education platform he spent nearly a decade building, including what he got right, what he got wrong, and how that informs his thinking going forward. Throughout the conversation, Scott brings a refreshingly self-aware perspective on his own financial habits: what he wishes he'd done sooner, how regularly investing even a little helps in the long run, and what he'd do differently as an entrepreneur the next time around.Scott's question for Timothy: How do we approach online education?Key Takeaways:Scott describes his work as a creative collaboration with artists, translating what happens on stage into what the audience actually hears and feels.He spent his twenties and early thirties living cheaply, often without an apartment, bouncing between tours — but with no savings to show for it, a gap he deeply wishes he had addressed sooner.Despite the touring industry's lack of contracts or union protections for crew, Scott notes that touring people rarely talk openly about rates — a habit that works against them collectively, though he actively tries to share what he knows with colleagues.Scott spent close to a decade building The Production Academy, generating around half a million dollars in revenue — but with very little profit, largely because he focused almost entirely on product development and not enough on sales and marketing.He identifies his biggest entrepreneurial lesson as the importance of complementary skill sets: building something alone means doing everything yourself, and the things you're not naturally good at — in his case, sales — tend to get neglected.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.The Production Academy

In this solo episode, Tim explores the tension between planning for the future and actually taking action in the present. Using examples from fitness, travel, and financial planning, Tim makes the case that over-thinking and over-planning can quietly become an obstacle — doing the work to decide whether to do the work, without ever getting started. Thoughtful, deliberate decision-making matters, but waiting for a perfect plan is itself a form of inaction, and that right here, right now is the only time any of us has to change our path for the better. Tim also walks through two common financial planning scenarios — buying a house and saving for retirement — to show how taking positive "imperfect" action today puts you in a stronger position to meet those moments later.One Key Takeaway: Don't let perfect be the enemy of good. No plan can guarantee the future, but taking positive action right now — even small, imperfect steps — can give you more and better options later.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.

In this episode, Tim sits down with Jason Narducy — musician, self-published author, and longtime member of Bob Mould's band and Superchunk — for a wide-ranging conversation about what it actually means to build a life in music. Jason shares the arc of his career, from a major label deal in the nineties through running a painting company for 20 years, to eventually going all-in on music again. He talks candidly about the economics of touring, the difference between working as a hired band member versus leading his own project, and how his solo shows have become one of his most rewarding musical outlets. Jason also discusses his self-published book Mostly the Van — a collection of short, human-centered essays about life in that middle space between fame and hobby — and reflects on the financial habits he's developed over decades of irregular income, including a hard-won lesson about credit card debt.Jason's question for Tim: What helpful financial advice do you have for musicians or any self-employed creatives?Key Takeaways:Jason ran a painting company for 20 years alongside his music career, providing income stability during slower periods — until he shut it down in January 2023 and committed fully to music.He describes his approach to scheduling: he commits fully to every project and doesn't back out, relying on bands planning ahead to lock in dates rather than managing a complex personal system.Jason reflects on the hidden complexity of being a working musician, noting that success requires skills far beyond playing — traveling, writing, interviews, interpersonal relationships, and financial awareness — and that many musicians aren't equally equipped for all of them.When touring with the REM tribute band he leads with Michael Shannon band, Jason prioritizes comfort over cost-cutting, believing that keeping experienced musicians happy is what allows the project to keep going long-term.His strongest personal financial habit: not spending money he doesn't have. An early experience with credit card debt left a lasting impression that shaped how he has managed money ever since.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Jason's InstagramJason's Threads

In this solo episode, Tim explores the tension between intuition and evidence when it comes to investing. He explains why reacting to how you  feel in the moment often leads to poor decisions, and how long-term data consistently points toward more effective strategies. Through real-world examples, Tim breaks down why trying to time the market rarely works, how automation and consistency can improve outcomes, and why patience is the most powerful force in building wealth. This episode is a reminder that successful investing isn’t about being right in the short term—it’s about aligning your behavior with what actually works over decades.One Key Takeaway: The best investors don’t follow their instincts in the moment—they follow the evidence and stay consistent over the long term.LinksSend me a question to be answered on a future episode. Sign up for the Keep It Easy newsletter. Selling out during the market’s worst days can hurt you, research shows — here’s how much you could lose Timing the Market Can Often Mean Missing the Best DaysTiming the Market: Why It’s So Hard, in One ChartHere's the Average Stock Market Return in Every Month of the Year

In this episode, Tim sits down with Christen Carter, founder of Busy Beaver Buttons & Merch, to explore how a DIY punk project grew into a decades-long business rooted in creativity, community, and resilience. Christen shares the scrappy early days of building a niche product for an overlooked audience, how she navigated major shifts in technology and demand, and the lessons she’s learned about leadership, hiring, and staying true to her values as the company scaled. The conversation also goes deep on money—covering scarcity mindset, early financial experiences, real estate decisions, and the balance between saving for the future and enjoying life today. Along the way, Christen offers an honest look at burnout, risk-taking, and what it actually takes to build something that lasts.Christen's question for Tim: how do you coach people whose income can fluctuate depending on what their business is doing to know when to save or spend like on a vacation or something fun?Key takeaways:Christen shares how she started Busy Beaver as a DIY punk project, spotting a niche for small custom buttons that no one else was really serving.She describes her early, scrappy approach to growth—reaching out to record labels, building within creative communities, and going direct-to-customer from the start.Christen reflects on the shift from doing creative work to running a company, including learning operations, HR, and building systems from scratch.She talks about how peer-to-peer learning and entrepreneurial communities helped her understand finance, forecasting, and how businesses actually work.Christen shares how early life experiences shaped a lasting scarcity mindset and discusses her long-term financial approach, including cautious decision-making, investing in real estate, and actively working to balance saving with actually enjoying her life.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Busy Beaver Buttons & Merch

In this solo episode, Tim pulls back the curtain and shares exactly how he invests his own money — not hot stock tips or market predictions, but the philosophy and decision-making framework behind his choices. He explains why he invests, how he thinks about risk and time, why maintaining strong cash reserves is essential, and why his timeline shapes nearly every decision he makes. Tim walks through when he buys, when he sells, and why he ignores financial media noise in favor of long-term discipline. This episode is about process over prediction — and about building a strategy you can stick with for decades.One Key Takeaway: The real edge in investing isn’t knowing what the market will do next — it’s having a clear plan, a long timeline, and the discipline to follow it.Links:Send me a question to be answered on a future episode. ( https://www.iselerfinancial.com/podcast )Sign up for the Keep It Easy newsletter. ( https://www.iselerfinancial.com/newsletter )

In this episode, Tim sits down with Vish Khanna, host and producer of the long-running podcast Kreative Kontrol, for a candid conversation about work, money, and creative independence. Vish reflects on leaving conventional media jobs to focus fully on his own show, and the emotional and financial tension that comes with choosing fulfillment over a steady paycheck. They explore how creative labor is valued (or undervalued), what it means to earn “enough,” and how freelancers navigate instability while trying to stay honest & engaged with their work. The conversation also touches on autonomy, burnout, family responsibility, and the realities of building a sustainable creative career outside traditional institutions.Vish's question for Tim: how does one achieve a healthy, relatively stress-free balance between vocational fulfillment and financial stability as a freelancer or independent business owner, especially after entering a freelance realm after 20 years of conventional jobs with regularly scheduled and consistent pay?Key Takeaways:Vish Khanna left a career in traditional media, even though it meant giving up stability, status, and a predictable paycheck.He describes the shift to independent work as emotionally liberating but financially disorienting, especially when there is no clear benchmark for success or failure.Vish highlights how independent creators often undervalue their labor, particularly when passion and personal identity are tightly bound to the work.He talks about the importance of building personal definitions of “enough”, and how that relates to industry norms or social comparisons.Vish discusses the tension between audience appreciation and financial sustainability, noting that validation doesn’t automatically translate into income.Links:Send me a question to be answered on a future episode. ( https://www.iselerfinancial.com/podcast )Sign up for the Keep It Easy newsletter. ( https://www.iselerfinancial.com/newsletter )Kreative Kontrol ( http://vishkhanna.com/ )Vish's profile on Talkhouse ( https://www.talkhouse.com/artist/vish-khanna/ )

Getting stuck in a “comfort zone” is often a sign that something isn’t actually all that comfortable—especially when it comes to money and long-term decisions. In this episode, Tim explores why so many important financial moves get stuck in the “I should” category, why waiting for the perfect moment usually makes things worse, and shares five practical, low-pressure ways to break out of an uncomfortable status quo and start making progress. One Key Takeaway: Real change doesn’t start with a perfect plan—it starts with small actions that gets you moving in the right direction.

In this episode, Tim sits down with Sarah Williams for a wide-ranging conversation about her creative path, professional evolution, and the realities of building a sustainable career on her own terms. Sarah shares her journey from early employee to co-owner & co-CEO, and how her leadership evolved as the company grew. She also reflects on burnout, delegation, financial stability, and redefining success beyond revenue. They explore how money, confidence, and self-trust intersect with creativity, especially when your career doesn’t follow a traditional path. Sarah Sarah’s question for Tim: how do you see the relationship between financial health and mental and physical health? Growing up I always had a lot of anxiety about Money. As I've gotten older and looked to create more financial security for myself, my family, and my business, that feeling doesn't really go away. How do you think about these challenges?Key Takeaways:Sarah Williams shares her path from being the first employee at her company to becoming co-owner and co-CEO, and how long-term commitment shaped her leadership style.She discusses the difference between building a lasting brand identity versus chasing short-term marketing trends and quick wins.Sarah reflects on learning to trust her instincts while also developing systems that support sustainable growth.She talks openly about learning to delegate and empower others as her role shifted from “doing everything” to leading a team.The episode highlights the importance of aligning personal values with professional goals in order to build a sustainable, fulfilling career.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Beardwood&Co

In this episode, Tim breaks down everything you need to know about Individual Retirement Accounts (IRAs) and how they fit into a long-term financial plan. He explains the differences between Traditional and Roth IRAs, who can contribute, how much you can save, and how taxes work both now and in retirement. Tim also covers investment choices inside an IRA, rules around withdrawals, and advanced options for self-employed people like SEP and SIMPLE IRAs. Along the way, he shares practical strategies for balancing short-term flexibility with long-term growth. One Key Takeaway: An IRA is one of the most powerful tools for building long-term financial security—but only if you understand how it works and use it intentionally.LinksSign up for weekly Office HoursSend me a question to be answered on a future episode

In this episode, Tim talks with cartoonist, writer, and teacher Emily Flake about building a creative career through multiple income streams, persistence, and adaptability. Emily shares what it’s really like to work in fields where rejection is common, success is unpredictable, and financial stability requires constant adjustment. Together, they explore the tension between creative fulfillment and practical money decisions, including saving, budgeting, and long-term planning. One Key Takeaway: A sustainable creative career is built less on sudden success and more on resilience, flexibility, and steady habits that support both artistic and financial health.Emily’s question for Tim: I’m a freelancer whose income varies wildly, and not only am i terrible with money but I’m actively afraid of thinking about it. I play chicken with my bank account, which is a checking account, because i don’t have a savings account. Don’t you dare even ask if I have a retirement account. I’m 48 gd years old. I guess my question is: how fucked am I?Key Takeaways:Emily Flake describes how her career has been built from many different income streams, including cartooning, writing, teaching, comedy, and running creative programs, rather than from one single job.She explains that publishing work in prestigious outlets like The New Yorker brings visibility and credibility, but does not guarantee long-term financial security.Emily talks about the ongoing reality of pitching work, receiving rejections, and learning to persist in an industry where “no” is far more common than “yes.”She reflects on how she balances creative fulfillment with practical concerns like paying bills and maintaining steady income.Emily speaks candidly about her discomfort with money, budgeting, and long-term financial planning, and how this has affected her decisions.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Emily's websiteSt Nell's Humor Writing ResidencyEmily's contributor page at The New Yorker

Managing money with an up & down income can feel overwhelming, especially when it comes to planning for the future. In this episode, Tim introduces the “Reservoir System,” a simple, intuitive framework for managing cash flow when your don't know how much you'll make this month or this year. Using the metaphor of managing a town's water supply, he explains how checking, savings, and investment accounts each serve a distinct purpose, and how to know when to keep cash on hand, when to save, and when to invest. This episode is especially helpful for freelancers, creatives, and self-employed people who want more stability without relying on traditional budgets. One Key Takeaway: Financial stability with an irregular income comes from prioritizing cash reserves first, then savings, and only investing once your short-term needs are fully covered.Links:Sign up for weekly Office HoursSend me a question to be answered on a future episode

In this episode, Tim  talks with Tony Rolando, musician, instrument designer, and founder of Make Noise Music, about building electronic musical instruments, growing a niche manufacturing business, and staying creatively grounded as success scales. Tony shares how his background as a musician shaped the unconventional design philosophy behind Make Noise’s modular synthesizers. They discuss the realities of scaling a creative business, including hiring, cash flow, and the tradeoffs between growth and personal freedom. The conversation also touches on Tony’s evolving relationship with money, health, and what it means to use success to support a meaningful life.Tony's question for Tim: With the way the current administration is increasingly isolating the US from the global economy, I have had the thought that I should shift my investments to be heavier in European and emerging markets. Add to that, that my retirement portfolio is almost entirely SRI and I sometimes feel it makes even more sense to shift to the European market. Do you have thoughts on this? Key Takeaways:Tony began Make Noise in 2008 after leaving a low-paying job at Moog Music, initially building modules by hand with no formal business plan.Early Make Noise designs emerged from Tony’s personal musical needs—creating modules that didn’t yet exist in the small modular synth market at the time.Tony approaches instrument design as a musician first, deliberately stacking functions into single controls to make instruments more expressive and playable.As Make Noise grew, Tony learned that hiring employees gave him his personal life back—but did not necessarily increase his income.Tony shares personal reflections on money, saving habits, health challenges, and the importance of actually using money to enjoy life.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Make Noise MusicMake Noise's YouTube pageTony's Bandcamp page

With investing tools cheaper & more accessible than ever, why would anyone still pay an advisor to manage their investments? In this solo episode, Tim breaks down how the biggest benefit of investment management isn’t better stock picks or secret knowledge, but help with follow-through, emotional decision-making, and actually doing the things you already know you should be doing. The episode closes with practical guidance on how to decide whether managing your own investments or delegating that responsibility makes the most sense for you. One Key Takeaway: Paying for investment management isn’t about access to information or tools—it’s about whether having support helps you make better decisions and stick with them over time.Links:Sign up for weekly Office HoursSend me a question to be answered on a future episode

Ryan Isaac is an education fundraiser & longtime baseball insider who spent more than a decade working in professional baseball. In this episode, Ryan shares how he broke into the industry, what it was like navigating the uncertainty & mobility of baseball careers, and why becoming a parent ultimately reshaped his priorities. He reflects on the identity shift that comes with leaving a dream job and finding new ways to stay connected to the work you love. The conversation also explores how Ryan rediscovered his voice through writing and launched his baseball newsletter, Warning Track Power, as a creative outlet beyond his day job.Ryan's question for Tim: What was the biggest obstacle you faced during your career transition? Key takeaways:Ryan shares his early career ambitions as a writer and journalist, including working at Wine Spectator in New York City while nurturing a long-standing passion for baseball. He describes leaving journalism to pursue a career in professional baseball during the early “Moneyball era,” including moving to San Diego without a job lined up to put himself closer to opportunity. Ryan recounts how a chance phone call led to his first full-time role with the San Diego Padres, marking his official entry into Major League Baseball operations. After leaving baseball, Ryan transitioned into fundraising for an independent school, gradually building experience through expanded responsibilities during the early COVID period. During the pandemic, Ryan reignited his creative outlet by writing about baseball, leading to the launch of his newsletter Warning Track Power as a personal and intellectual release.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Ryan's newsletter Warning Track PowerWarning Track Power's Substack page

Every year, financial “experts” roll out confident predictions about what the markets and economy will do next — and almost every year, they’re wrong. In this solo episode, Tim explains why financial forecasts are so appealing, why they’re fundamentally unreliable, and how chasing certainty can actually hurt your long-term financial health. Instead of guessing the future, he lays out a simple, durable framework for building stability, flexibility, and peace of mind in an unpredictable world. One Key Takeaway: You don’t need to predict the future to build financial security — simple habits, long-term thinking, and preparation for uncertainty matter far more than any market forecast.Links:Financial Forecasts Are Bullsh!tSign up for weekly Office HoursSend me a question to be answered on a future episode

Drumming instructor Todd Trainer joins Tim to talk about how an unexpected job loss pushed him into building a new career around teaching. He shares the story of growing his student base from DIY flyers to a full teaching practice, and why helping beginners find confidence & creativity has become some of the most meaningful work of his life. Todd also talks about adapting his teaching style for different learners and the philosophy that guides his approach to drumming instruction.Key Takeaways:Todd Trainer—best known as the drummer of Shellac—shares how losing a long-time job pushed him toward drumming instruction as a new career path. He started his teaching business in DIY fashion, putting up flyers & offering mobile lessons at his students' homes or rehearsal spaces. Eventually, Todd (and his wife, a designer) built a website that features scheduling tools & a payment system, which have been essential to the business’s success.His teaching philosophy emphasizes creativity, individuality, and imagination—encouraging students to develop their own unique style rather than chasing technical perfection. Todd finds deep fulfillment in teaching beginners, especially children, and describes how helping them discover their first drumbeat is one of the most rewarding parts of instruction. Teaching has become emotionally meaningful for Todd: the value exchanged between student and instructor goes far beyond the time they spend together.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Todd Trainer Drumming InstructionTwin Cities Drum CollectiveShellac of North America

Holiday spending can creep up fast — and the new year is the perfect time to reset. In this episode, Tim introduces the 4-Week Financial Detox, a simple step-by-step process designed to help you pause discretionary spending, reset your baseline expenses, eliminate costly subscription “leaks,” and refocus your money on what truly matters. Whether you’re rebuilding after the holidays or just ready to use your money more intentionally, this short reset can help you start the year with more clarity, control, and confidence in your financial life. One Key Takeaway: Small, temporary changes to your spending habits can create lasting improvements in financial health — especially when you focus your money on what genuinely enriches your life.Links:4-Week Financial DetoxSign up for weekly Office HoursSend me a question to be answered on a future episode

In this wide-ranging & deeply reflective conversation, guitarist Randy Randall (No Age, Hyphenate with Randy Randall) talks about the shifting economics of indie music, redefining success as he became a parent, and building a freelance career in marketing almost by accident. From his early days immersed in the DIY community to learning resilience in the gig economy, Randy shares an honest, unglamorous, and strangely hopeful portrait of what it means to be a lifelong creative worker. He & Tim dig into the real tensions between art and money, how freelancing in marketing actually aligns with his long history of conceptual art, and why optimism is essential when your livelihood depends on the next email, gig, or project.Randy's question for Tim: When is it a good idea to put money in a traditional IRA versus when is it a good idea to put money in a Roth IRA?Key takeaways:Randy describes juggling multiple identities — musician, podcaster, and now freelance marketing professional — and the tension between what he wants to say he does and what actually pays the bills. He explains why touring slowed down: part parenthood, part industry collapse, part shifting audience habits — and how those changes pushed him into new types of work. Randy explains how he fell into freelance marketing during the pandemic, discovering it uses the same skills he honed through years of art-punk conceptual work. He discusses the unpredictable nature of gig-based creative work, where every project feels like “starting from zero” and momentum is never guaranteed. Randy and Tim dive into the emotional resilience required to freelance — balancing optimism, uncertainty, and the long game of sustaining a creative life. Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Randy's websiteHyphenate With Randy RandallTim's episode of HyphenateNo Age's Bandcamp pageLifeguard's "Ripped And Torn", produced by Randy

In this episode, Tim explains why cash flow is the foundation of every financial plan — and introduces a simple technique to make saving money easier and more consistent. By identifying your “invisible number,” the small amount you can save automatically without ever noticing, you can improve your cash flow, build long-term security, and reduce friction in your financial life. Tim breaks down how this approach works, why automation matters, and how small, steady habits can quietly transform your financial trajectory.5 Key Takeaways:Cash flow is the foundation of financial planning. Every major financial decision — investing, buying a home, planning for retirement — depends on knowing what you earn, spend, and save.Income = spending + saving. This simple equation underpins every cash-flow conversation and highlights the trade-off between what you use today and what you set aside for the future.Your “invisible number” makes saving effortless. This is an amount of money small enough to transfer automatically without affecting your daily life — your savings grow without conscious effort.Increase your invisible number slowly. After a few months, bump it up in small increments until you begin to notice it — then dial it back slightly and automate that amount indefinitely.Tie your number to something you buy without thinking. A daily coffee, a sandwich, a beer — if you’d spend it without hesitation, you can likely save it without noticing, too. Small, automated transfers add up meaningfully over time.Links:Sign up for weekly Office HoursSend me a question to be answered on a future episodeSign up for the Keep It Easy newsletterThe cost of a cup of black coffee at Starbucks

Film and video editor Max Goldblatt joins Tim to talk about building a creative career across indie films, digital content, and nearly a decade of touring. He shares how early exposure to editing shaped his path, how short-film work opened doors to feature projects, and what it takes to balance passion, stability, and financial responsibility in an unpredictable industry. Max also reflects on navigating rate negotiations, imposter syndrome, and the realities of sustaining creative momentum over time.Max's question for Tim: My kid is three. School is expensive. I know that a 529 plan has some limitations, like what if she doesn't go to college? Is there a smart and flexible way to set her up for success?Key takeaways:Max Goldblatt is a film, TV, and digital video editor based in Los Angeles, working both on independent films (his “passion work”) and as a lead editor for a production company that handles a range of clients, including MasterClass.He learned the craft early by watching his father, editor Mark Goldblatt, spending spring breaks in editing rooms for major films like Starship Troopers, True Lies, and Armageddon.Before establishing himself as an editor, Max spent nearly nine years touring, first as a videographer for his cousin Pete Yorn and then as a merch manager for various artists (including Sufjan Stevens).He now balances steady staff work with independent feature opportunities, with his company allowing him to step away for film projects and return afterward, providing stability during volatile industry periods.On finances, Max says he’s always been frugal and cautious, started a Roth IRA early due to childhood acting income, avoids credit card debt, and prefers a “save first, spend within means” approach rather than rigid budgeting.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Max's websiteThe trailer for Sacremento, a feature film edited by MaxSt Vincent's MasterClass (edited by Max)Ringo Starr's MasterClass (edited by Max)

As the year winds down, Tim shares five practical steps you can take right now to lower next year’s tax bill. From maximizing retirement contributions to understanding energy-efficiency credits, this episode focuses on simple, actionable strategies for creative professionals and self-employed listeners. Tim breaks down how tax-deferred accounts, health savings accounts, and even small investment decisions can make a meaningful difference — without the last-minute stress of filing season. Five Key Takeaways:Contribute to tax-deferred retirement accounts. Deposits into IRAs, 401(k)s, and similar accounts reduce current-year taxable income. Remember: new accounts must be opened before December 31 to count for this tax year.Use a Health Savings Account (HSA) if eligible. HSAs offer a triple tax advantage: contributions are tax-deductible, growth is untaxed, and qualified withdrawals are tax-free.Offset gains with losses. Selling underperforming investments in non-retirement accounts lets you claim up to $3,000 in capital losses per year to reduce taxable income — but watch for wash-sale rules.Take advantage of home energy credits. Energy-efficient home upgrades (like HVAC systems, doors, or windows) can qualify for valuable federal credits, but some expire at the end of 2025.Consider strategic charitable giving. While deductions only apply if your itemized total exceeds the standard deduction, bundling several years of giving into one tax year can increase tax efficiency for higher earners.Links:Sign up for weekly Office HoursSend me a question to be answered on a future episodeSign up for the Keep It Easy newsletterThe Congress.Gov page on HSAsEnergy Efficient Home Improvement Credit

In this episode, Tim talks with writer, drummer, and content specialist John Dugan about creative work, shifting career priorities, raising kids in a music-rich environment, and how financial needs and perspectives evolve over time. John reflects on decades in bands including Chisel, his transition from journalism into content strategy for the design world, and what happens when art, family life, and money all need to coexist. They also discuss saving habits, risk tolerance, reunion shows, and supporting the next generation of artists—including John’s teenage son’s band, Uniflora.John's question for Tim: why would someone invest in life insurance? Is that an alternative to the stock market?Key takeaways:John Dugan is a longtime drummer & writer who now works as a content specialist in the design industry. He shifted from “cool, low-paying jobs” in journalism and cultural criticism to a more sustainable career path once he became a parent and needed greater financial stability. Though he played extensively in touring bands, music never paid his bills; he always held another job to maintain stability. John learned the value of maintaining an emergency savings buffer early, influenced by frugal parents and reinforced by the realities of touring life. He continues to think about risk vs. caution in personal finance, recognizing that while he tends to be risk-averse, some well-timed risks can meaningfully shape financial outcomes.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.John's websiteChisel's Bandcamp pageUniflora, John's son's band

It's the first listener mailbag episode! Tim answers real money & personal finance questions from listeners about ethical investing, managing debt, and overcoming money-related shame. He explains how to easily invest according to your values, how to balance saving while paying off student loans, and when to use savings to tackle credit card debt. The conversation ends with a thoughtful reflection on emotional well-being — how to move past financial shame and build confidence through small, consistent wins.Key Takeaways:Ethical investing is more accessible than ever. Lower cost ESG & SRI funds allow everyday investors to align their money with their values without paying high fees.Perfection isn’t required. There is no “clean” money, bank, company, or country — but choosing options that most closely reflect your ethics is better than sitting out entirely.The 50/30/20 rule still applies — with flexibility. When paying off student loans or other debt, treat recurring payments as essentials (the 50%) and keep aiming for 20% savings when possible.Tackle high-interest debt first. No amount of investing can outpace credit card interest, so pay those balances before focusing on long-term investments.Let go of shame and rewrite your story. Shame is a story we tell ourselves — and if you're going to make up a story about yourself, it might as well be a good one! Start collecting evidence of good habits, look for supportive accountability, and celebrate even small wins.Links:Sign up for weekly Office HoursSend me a question to be answered on a future episodeSign up for the Keep It Easy newsletter

Benjamin Percy has built a career bridging literary fiction, comics, and Hollywood storytelling. As the author of acclaimed novels, comic book arcs for Marvel and DC, and scripts for film and audio drama, Ben joins Tim to discuss the craft and discipline behind a self-employed creative life. He talks about writing routines, handling rejection, learning to navigate the business side of art, and balancing creative ambition with family life. The conversation explores how consistency, humility, and persistence turn creative work into a sustainable career. Ben's question for Tim: AI worries me for all the standard reasons, but it also worries me because I anticipate the over promise and overspending will reach a point of bubble bursting correction. Is there any sense, even a vague one as to when that might happen, and how to shield yourself from the fallout?Key takeaways:Benjamin's storytelling spans novels, comics (Wolverine, Batman, Green Arrow), screenplays, and podcasts, and writing across mediums has helped him become a better writer (and pay his bills).He describes early failures and rejections as essential to building resilience and understanding his craft.Ben blurs boundaries between literary and genre fiction, arguing that good storytelling transcends category.A former university professor, Ben believes in being a "good literary citizen": sharing knowledge with newer writers and opening doors when possible.Longevity in creative work comes from patience, adaptability, and the ability to keep going through uncertainty.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Benjamin's websiteThe End Times (physical subscription)The End Times (digital subscription)Red Moon, Ben's breakout novelBen's page at Marvel ComicsBen's page at DC Comics

What would it take for work to become optional? In this solo episode, Tim walks through a simple framework for estimating your “enough” number—the amount you’d need in savings & investments to reduce or even eliminate the obligation to work. Using the 4% and 25× rules, he explains how to calculate a  target nest egg amount, why it’s useful even if you never plan to retire, and how small, consistent habits can turn into huge long-term growth over time. Whether your dream is full retirement or just the freedom to choose when & how you work, this episode offers clear & practical insight for building that future.Key Takeaways:The 4% rule (and its partner, the 25× rule) provides a simple way to estimate how much you’d need to make work optional.Even if you never plan to “retire,” saving and investing buys you freedom and flexibility later in life.Your target nest egg is determined by your annual spending—spend more, need more; spend less, need less.Consistent small actions—saving a little more, paying debt faster, investing regularly—compound into big results.Financial independence isn’t about quitting work; it’s about creating options and reducing obligation.Links:Sign up for weekly Office HoursSend me a question to be answered on a future episodeSign up for the Keep It Easy newsletterWilliam Bengen's Wiki pageInvestopedia's page on the 4% Rule

For more than 30 years, Michael Perry has built a life around words — from essays and bestselling books to one-man shows and live events. In this conversation, Mike shares how his blue-collar roots shaped his approach to creative work and money, why he still keeps his nursing license “just in case,” and what it really takes to sustain a self-employed creative life. He and Tim talk about saying no to the wrong opportunities (even when Oprah calls), learning business skills on the fly, and how low overhead, multiple income streams, and a willingness to keep “shoveling” have allowed him to keep doing what he loves.Mike's question for Tim: Regular IRA, Roth IRA, or SIMPLE IRA?Key takeaways:Longevity through discipline: Mike has supported himself solely through writing since 1992 — proof that persistence can outlast uncertainty.Money is part of the craft: Understanding taxes, mileage, bookkeeping, and contracts enables creative independence.Multiple income streams matter: Like his farmer father, Mike learned to diversify work to stay sustainable.Integrity over exposure: Turning down a high-profile appearance taught him the value of aligning work with values.Freedom, not fame: For Mike, success means autonomy, stability, and the ability to keep creating on his own terms.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Michael Perry's websiteHis new book Improbable Mentors & Happy TangentsPopulation: 485, Mike's breakout memoir about small-town life and volunteer firefighting

What comes to mind when you hear the word “wealth”? In this episode, Tim explores how our ideas about money are shaped not just by math & spreadsheets, but by deep emotional lessons from family, culture, and experience. He unpacks why textbook definitions of wealth often fall short, shares perspectives from author Morgan Housel, and offers a new way to think about building abundance: creating more “perfect average days”. Along the way, Tim explains how saving and investing can buy you freedom, time, and peace of mind—keys to living a life of true wealth.Key takeaways:Wealth is more than a number. Financial education often emphasizes the math side of money—budgets, compounding, spreadsheets—but emotional lessons from family and culture shape our views about money just as strongly.Early experiences—such as seeing family members struggle with debt, investing, or real estate—can create lasting beliefs about what’s “safe” or “risky” (even if those beliefs aren’t accurate or helpful).Abundance is about “more than enough.” But abundance depends on how much you think you need, not just how much you have.Freedom > possessions. Wealth is really about time and freedom, not just money or material goods.Instead of chasing endless big goals (which look great on social media), let's reframe wealth as the ability to afford more “perfect average days”—days filled with comfort, connection, and choice. Saving and investing is a way to buy those future days of freedom.Links:Sign up for weekly Office HoursSend me a question to be answered on a future episodeSign up for the Keep It Easy newsletterMorgan Housel

Sam Ratto is the founder of Videri Chocolate Factory in Raleigh, NC, and recently started Golf Golf Golf, an indoor golf simulator business. In this episode, Sam shares his winding path from surfing & skateboarding culture, launching a bean-to-bar chocolate company, and building a new hospitality venture around his love of golf. He talks about the realities of small business finance, lessons learned from failures, and how he balances entrepreneurial risk with personal stability. One key takeaway: The creative path to entrepreneurship isn’t linear—financial discipline and resilience help make bold risks possible.Sam's question for Tim: what is going to happen with tariffs in the next 12 months?Key takeaways:Sam reflects on his unusual career path—from surfer & skateboarding industry work, to marketing & touring, and eventually to chocolate making.He highlights lessons from running a business: the importance of self-motivation, honesty with oneself and employees, and the heavy mental load of constant financial stress.Sam shares how he learned disciplined personal money habits from his fiancé, including paying off credit card debt and adopting cost-cutting practices like packing a lunch.Golf Golf Golf emerged from his love of golf and recognition that indoor simulators offered a hospitality-driven, lower-overhead business in a growing market.He connects golf to entrepreneurship, noting both require persistence, resilience, and the ability to face setbacks with optimism (and a lesson from his grandmother).LinksSend me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Videri Chocolate Factory – Sam’s chocolate business in Raleigh, NCGolf Golf Golf – His indoor golf simulator businessSimon Sinek Podcast – Referenced for entrepreneurship insightsMark Twain: A Life by Ron Chernow – Biography Sam mentioned listening toTree Farm Golf Club – South Carolina golf course he cited as a model of hospitality

In this episode, we unpack why having the right amount of cash in savings is essential—but why holding on to too much can quietly hurt your financial future. While an emergency fund provides short-term stability and peace of mind, excess cash loses value every year to inflation. By contrasting the short-term safety of savings with the long-term growth of investments, the conversation highlights the importance of balance. Practical frameworks like the “barbell model” and simple steps for gradually investing extra funds show how to move beyond just saving to start building lasting financial security.Key takeaways:Aim for an emergency fund with at least 3–6 months of expenses (or more if self-employed) in an FDIC-insured savings account.Cash is great in the short term—but lousy in the long term. Inflation erodes buying power over time, making cash unreliable for long-term goals.Though volatile in the short term, stocks and other investments historically outpace inflation over long periods.The barbell model: balance the stability of cash with the growth potential of investments to create financial strength.Start small and stay consistent—invest extra cash gradually, automate contributions, and avoid moving the goalposts on your savings target.Links:Sign up for weekly Office HoursSend me a question to be answered on a future episodeSign up for the Keep It Easy newsletter

Musician Macie Stewart has been performing since her teens, from early bands like Kids These Days to co-founding Finom & becoming a fixture in Chicago’s improvised music scene. In this episode, she talks about finding community at Constellation (an excellent Chicago venue), balancing the realities of freelance income with creative freedom, and what success looks like for her today. One key takeaway: building a sustainable creative life means balancing financial practicality with artistic curiosity and community.Macie's question for Tim: how to make a yearly budget when income fluctuates so greatly? Key takeaways:Macie began touring as a teen and later found her way into Chicago’s improvised music scene through current bandmate Sima Cunningham.Although she's been a working musician for many years, only in the past five years has she fully realized music can be her career.Macie supports herself through touring, session work (especially strings and arranging), licensing, scoring, grants, royalties, and collaborations.She saves regularly, uses a high-yield savings account, contributes to a Roth IRA, and focuses on building stability as a self-employed musician.For Macie, success means creative freedom, sustainable touring, and the ability to pursue unconventional projects like theater or dance collaborationsLinksSend me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Macie's websiteFinom's websiteConstellation in ChicagoKids These Days wiki pageSound & Gravity festival

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?

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: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

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

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: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

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

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:Christian trained as a classical violist at Juilliard before shifting his creative focus toward contemporary composition and performance.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.Christian also composes for theater and dance, including sound design.He discusses the challenge of making a living through creative work and shares how freelance work requires both flexibility and resilience.He reflects on how curiosity and collaboration have driven big career decisions throughout his life.LinksSend me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Christian's websiteRachel's on Touch And Go's websiteSITI CompanyPalissimoThe coffee roaster I use (now discontinued): FreshRoast SR 500Sweet 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 takeawaysRecessions 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.LinksSend me a question to be answered on a future episode.Sign up for the Keep It Easy newsletterInvestopedia 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: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.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.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.Mikael talks about living modestly and his techniques for managing cashflow with an up & down income.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.LinksSend me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Mikael's websiteMikael's PatreonMikael's documentary on Bob JamesWilco's websiteJohn McEntire's websiteIsotope 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 takeawaysPay 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.LinksSend 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 takeawaysLara is the co-owner of Farmscape, the largest urban farming company in the U.S.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.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.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.At Farmscape, she champions employee financial health by offering a 401(k) with matching and encourages investing through relatable, experience-based education.LinksFarmscapeJust Keep Buying by Nick MaggiulliSend me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.

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 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 you want to workYou can let time do the heavy lifting for you by choosing & sticking with the simplest investment strategy aroundLinksHow To Turn $6,000 Per Year Into $1 MillionInvestor.gov's Compound Interest CalculatorSend me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.

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 Tim: I don't really pay attention to or care about cryptocurrency. Should I, and or when should I start paying attention? Key takeawaysMatt's journey to becoming a full-time musician was gradual. He began earning money as a musician in the late ’90s, eventually quitting his day job around 2006 when touring became frequent.He met Justin Vernon (Bon Iver) while touring with the Rosebuds. They bonded while rooming together on tour, and Matt later joined Bon Iver in 2008.While often seen as glamorous, Matt emphasizes how tour life – like long waits, shared living spaces, and repetitive logistics – can become very routine and normal for musicians.He candidly shares mistakes from his early financial life, especially around credit card use, and how he eventually cleared his debt through awareness and restraint.Matt discusses how he prices his work, considering factors like time commitment, travel, and what other musicians get paid for the same commitment when evaluating offers.LinksMatt's Grammy Awards pageMatt's credits via AllMusic and Discogs Matt's IG pageSend me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.

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 emergency or opportunity fund allows you to face uncertainty with a safety net.Maintaining more access to credit than you need means you can access money quickly when you need it – and it's good for your credit score!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.

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 Tim: 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:Rebecca joined her first band, The Minders, after moving to Denver and connecting with members of the Elephant 6 music collective.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.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.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.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 InstaThe Minders Wiki, Bandcamp, & InstaWild 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 BudgetFoundational 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 Tim: 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: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.He details the logistics and emotional intensity of life on the road, from small clubs to selling out large venue.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.Adam shares the importance of understanding the business side of being a bandleader and the responsibility he feels to both bandmates and crew.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 websitePizza Lupo in Louisville KYMurder 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 episodeSign 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.LinksSend 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