What Money Can’t Buy You

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/]

What We Talk About When We Talk About Investing

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. [https://www.iselerfinancial.com/podcast] Sign up for the Keep It Easy newsletter. [https://www.iselerfinancial.com/newsletter]