All Episodes
Displaying 1 - 20 of 44 in total
Why Pay Someone To Manage Investments?
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 ...
Ryan Isaac - Education Fundraiser & Baseball Newsletter Writer
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 br...
Financial Forecasts Are Bullsh!t
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 epi...
Todd Trainer - Drumming Instructor
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 growi...
4-Week Financial Detox
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 p...
Randy Randall – Musician, Podcaster, & Freelance Marketer
In this wide-ranging & deeply reflective conversation, guitarist Randy Randall (No Age, Hyphenate with Randy Randall) talks about the shifting economics of indie music...
Easy Cash Flow: What's Your “Invisible Number”?
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 consiste...
Max Goldblatt – Film & Video Editor
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 h...
5 Tips To Save On Next Year’s Tax Bill
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...
John Dugan - Content Specialist in the Design Industry
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 enviro...
Listener Mailbag 01
It's the first listener mailbag episode! Tim answers real money & personal finance questions from listeners about ethical investing, managing debt, and overcoming mone...
Benjamin Percy – Storyteller
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, ...
Quick Nest Egg Calculation
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...
Michael Perry - Self-Employed Writer
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 sh...
What Is “Wealth”?
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 emo...
Sam Ratto - Chocolate Maker
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 share...
The Problem With Too Much Cash
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 ...
Macie Stewart - Musician
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 mus...
Is Buying A Home A Good “Investment”?
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 resi...
Sam Kassirer - Musician & Producer
Sam Kassirer is a musician, producer, and the founder of The Great North Sound Society, a residential recording studio in rural Maine. In this episode, he talks about ...
