The Thing We Never Talk About

In this episode, Tim sits down with Alan Sisto, host of The Prancing Pony Podcast, for a conversation about how a podcast on the works of J.R.R. Tolkien went from side hobby to full-time job. Alan started the show while working as a photographer and voiceover artist, and eleven years and 400+ episodes later it’s now his main source of income. He describes how a Facebook group and a voiceover coach...

Having more money than you’ve ever had before sounds like a great problem to have (and it is), but it also creates a kind of analysis paralysis that seldom gets talked about. In this solo episode, Tim explores what happens when the rules that work for managing a normal amount of money stop applying, and why doing nothing — letting all the money sit as cash indefinitely — is the wrong move. He walk...

In this episode, Tim sits down with Matthew Wortz, a New York-based actor who came to the craft after decades in conventional employment. Matt describes how being laid off in his previous job as a web designer led to showing up at an open call for extras on a film set. What started as something to stay active has turned into a serious second career: he's now a SAG-AFTRA member, working his way up...

The stock market is likely to go up over time — but that doesn't help if it crashes right when you need the money. In this solo episode, Tim uses the framing of "insurance" to explain why diversification across cash, bonds, and stocks is a way of managing the known risks that come with each type of investment. Cash protects against short-term market drops; stocks protect against inflation over the...

In this episode, Tim sits down with tour manager & tour accountant Paul Dalen for a candid conversation about money, career, and what it actually takes to make retirement a real possibility after decades on the road. Paul traces a career that has taken him from front of house audio engineering to production management to artist management and back to touring, including a period about 15 years...

Money has different jobs depending on when you need it — and confusing what works for one timeline with what works for another is one of the most common financial mistakes. In this solo episode, Tim walks through the difference between saving money and building wealth, using this definition of wealth as a guide: the ability to do what you want, when you want, with whom you want, for as long as you...

In this episode, Tim sits down with Serena Lander — self-employed artist, tattoo artist, and owner of a multi-unit property — for a conversation about building a creative life on your own terms. Serena traces her path from tattooing as a teenager in British Columbia, when she was one of only a handful of women in the craft in North America, through nearly four decades of working entirely for herse...

Should you pay off your mortgage early or invest the money instead? In this solo episode, Tim walks through a real case study involving a couple who received a significant one-time windfall and want to know how to use it wisely. He compares three options — investing the full amount right away, paying off the mortgage entirely, or splitting the difference — across a twenty-year time line, and share...

In this episode, Tim sits down with Richard Dansky — game narrative expert, fiction writer, and tabletop role-playing game designer — for a wide-ranging conversation about building a creative career across multiple formats and revenue streams. Richard traces his path from tabletop games starting in the '90s through nearly three decades of video game work, including a long tenure as the central nar...

Doing nothing with your money feels safe — but it comes with real costs, both financial and emotional. In this episode, Tim explains why cash is essential for short-term stability but loses value over time to inflation, and why investing anything beyond your cash reserve is one of the most important financial moves you can make. He also explores two emotional patterns that keep people stuck: "the...

In this episode, Tim sits down with Angela Hugghins, esthetician & founder of Cult of Reason skincare, for a wide-ranging conversation about what it looks like to build multiple businesses on your own terms. Angela shares how she structured her solo practice to protect her hands, her energy, and her lifestyle after nearly 30 years in the industry, why she made a significant price jump despite...

A surprising amount of what looks like a money problem is actually something else wearing a money costume. Tim shares a story from his early touring days, when a tour manager's blunt question — "Is this about the money, or is it something else?" — cut through a negotiation in under a minute. He applies that same question to financial planning, using the common example of someone wondering if they'...

In this episode, Tim sits down with Katie Cunningham, a freelance producer and writer-director, for a conversation about risk, identity, and how she built a creative life on your own terms. Katie shares the story of leaving a corporate marketing job in 2022 to write and direct a self-funded short film (even though her finances weren't necessarily ready for the leap), and how that decision led to l...

When people feel financially stretched, it can be hard to decide where to cut back. What if you just focused on earning more instead? It seems like the logical solution — but there's a problem with that logic: almost everyone increases their spending when their income goes up. The result is that you find yourself right back where you started, just at a higher level. In this episode, Tim shares a r...

In this episode, Tim sits down with Rob Mazurek — composer, painter, and self-proclaimed abstractivist — for a wide-ranging conversation about what it looks like to build a life entirely around creative vision. Rob traces his path from Chicago's boundary-pushing music scene of the '90s through his current life in Marfa, Texas, where he and his wife have built a low-overhead, high-quality existence...

Most people with unconventional careers started out with a simple financial dashboard: one look at the bank account told them everything they needed to know. But over time, as careers grow and income gets real in a new way, that single number stops telling the whole story. Tim walks through what happens when the bank account stops making sense: why leaving too much money sitting in cash trades sho...

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...

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 tha...

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 a...

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 engagemen...

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-ed...

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...

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 co...

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, b...

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...