What We Talk About When We Talk About Investing

Mary Lattimore — Musician

In this episode, Tim sits down with Mary Lattimore — classically trained harpist, solo recording artist, and film composer — for a candid conversation about building an unconventional life in music. Mary traces her path from growing up around the harp in Asheville, through years of juggling multiple part-time jobs in Philadelphia, to the Pew Fellowship that gave her the financial breathing room to focus on music full time. She talks openly about her complicated relationship with money: the anxiety that came with her first large sum, the difficulty of saving when income ebbs and flows, and the game-changing decision to hire a business manager who helped her get her finances under control. Mary also shares the story of co-purchasing an apartment in a tiny village in Tuscany, what it felt like to sign those papers, and why owning a little piece of the world somewhere beautiful felt like a dream she barely knew she was allowed to have. Mary's question for Tim: What's your advice for someone whose money ebbs and flows and who is bad about saving? Key Takeaways: 1. Mary describes herself as both a freelance musician and a small business owner — that distinction matters, since thinking of her work as a business has shaped how she manages income, taxes, and team-building. 2. The Pew Fellowship she received in 2014 was the turning point that allowed her to stop working multiple part-time jobs and focus on music full time, though she recalls that seeing her bank account full for the first time actually triggered anxiety rather than relief. 3. Her path out of classical music into her own solo work was gradual and social — friends in Philadelphia asking her to add harp to their records, followed by touring with Thurston Moore, whose mastery of free improvisation pushed her to trust her own musical instincts. 4. Mary co-purchased an apartment in a village of 200 people in Tuscany — splitting the cost and the schedule with a friend — and describes it as a dream she barely believed was possible, especially given that homeownership in the U.S. feels out of reach. 5. Her business manager helped her set up LLCs for both her business and her Tuscany apartment, put her on a regular payroll through her S corp, and helped her make sense of the complex label statements she had previously found overwhelming. 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] Mary's website [https://marylattimore.net/] Mary's IG [https://www.instagram.com/maryoverthere/]

What Money Can’t Buy You

You know what they say about money & happiness — but we all still want to try a little bit, right? In this solo episode, Tim shares a personal story from his touring career: the year he made the most money he'd ever made as an audio engineer, stayed in nice hotels, and ended up feeling ... deeply unhappy. What was missing was human connection, the sense of being part of a team, the feeling that the work actually mattered — and money is a poor substitute. That realization didn't just change how Tim thought about money; it directly led to the career he has now, built around helping people with unconventional careers use their money to support the lives they actually want to live. One Key Takeaway: More money is swell, but it's not really the goal. The goal is a fulfilling life, and money is just one tool for building 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]

Cheetie Kumar - Chef & Owner (Ajja & Big Cat)

In this episode, Tim sits down with Cheetie Kumar — chef, owner of Ajja and Big Cat in Raleigh, NC, and two-time James Beard Award nominee — for a wide-ranging conversation about what it looks like to build a life and a business from scratch with more passion than experience. Cheetie traces her path from immigrating to the US as a child, through punk rock and bartending, to opening a music venue and eventually a restaurant with no formal training. She speaks candidly about the financial blind spots that nearly derailed her early restaurant — underpricing her menu, not understanding cost of goods, and spending years without a real grasp of finances. She also reflects on the emotional weight of growing up with financial insecurity and how that shaped her relationship with money through the present day. Throughout the conversation, Cheetie brings the same thoughtful, collaborative ethos she applies in the kitchen to questions about entrepreneurship, financial literacy, and what it means to build something that reflects your values. Cheetie's question for Tim: What are five essential financial literacy elements for a first-time small business owner? Key Takeaways: 1. Cheetie describes herself first as someone who fixes problems: the reality of running multiple restaurants is that the job is mostly about solving whatever is in front of you. 2. Her path to being a chef was indirect: she was bartending to support her touring life when a lease on a real restaurant space presented the opportunity to start her own restaurant, and she learned how to do that entirely on the job. 3. The DIY ethos of punk rock deeply shaped how she approached opening her first venue and restaurant — not waiting for permission or credentials, but simply identifying what was missing and building it herself. 4. Cheetie shares how not taking on outside investors meant keeping full ownership so that no one else had a claim on what she built, even when that made things harder in the short term. 5. She now approaches finances with diligence and rigor — tracking expenses, reconciling regularly, and understanding that there is no substitute for staying on top of the numbers, because looking away even briefly can put you in the red. 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] Cheeti's IG account [https://www.instagram.com/cheetieku/] Ajja [https://www.ajjaeats.com/] Big Cat on Brookside [https://www.bigcatbrookside.com/]

Getting Your Financial House In Order

Most people's financial lives are spread across a patchwork of accounts, loans, insurance policies, and retirement funds — some forgotten, some incomplete, some never quite dealt with. Getting your financial house in order means bringing all of it together in one place so you can finally see the whole picture. Tim walks through the process he uses at the start of every financial planning engagement: gathering all of your important financial information, reviewing it to make sure the details are accurate and complete, and then evaluating how the pieces fit together using a series of financial scores that show where things stand right now. Because before you start making plans for the future, you need a clear, honest baseline for where you are today. One Key Takeaway: You can't make a plan for where you're going if you don't know where you are right now. 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]

Andrew Sandoval - Producer & Book Publisher

In this episode, Tim sits down with Andrew Sandoval — producer, manager, and founder of Beatland 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: 1. 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. 2. 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. 3. 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. 4. 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. 5. 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/]