Listen Score
LS 25
Global Rank
TOP 10%

ABOUT THIS PODCAST 🔗

Update frequency:
weekly
Average audio length:
40 minutes
Guest interviews
English
United States
75 episodes
since March 20, 2025
episodic

LATEST EPISODE 🔗

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 …

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PREVIOUS EPISODES

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 weal…
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 hand…
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, payi…
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…
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 importan…
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, an…
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 app…
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 f…
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 yo…
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