Microcap investor Ian Cassel and currency trader Brent Donnelly meet for the first time on Just Press Record to compare what their own track records taught them about conviction, position sizing, and the difference between feeling certain and being right.

Brent explains what he found when he graded his trades by confidence, and Ian shares why he now starts with smaller positions and lets a company earn a bigger place in his portfolio.

Matt Zeigler brought them together after reading their books back to back, but the parallels go well beyond investing. An unanswered message led Ian to a longtime mentor, and one of the best responses Brent ever got from readers came after he explained how a trade went wrong.

Topics covered

• How Ian turned an unanswered message into a 10- to 15-year mentorship by researching a stock his future mentor already owned
• How Brent went from trading currencies to making a cartoon for Canadian television, and how a recurring question on the trading desk eventually turned him into a daily writer
• Why readers responded so strongly when Brent explained a New Zealand dollar trade that went wrong about an hour after he published it
• What Brent did when a trading strategy that had worked for years stopped paying off, and how Ian added new investing skills without abandoning old ones
• Why Ian starts smaller today, what earns a stock a larger position, and how often a deeply discounted microcap actually recovers
• How trading costs and limited liquidity can leave opportunities open to individuals that a large fund cannot use
• What Ian learned from visiting a 65-cent stock that made iPhone screen protectors during the financial crisis
• What a study of 45 stock pickers and Brent's own trading records reveal about the decisions that matter after the initial buy

Timestamps

00:00 Why a microcap investor and a currency trader should meet
05:12 The message board that led Ian to a mentor
11:28 How a currency trader became a cartoon creator and financial writer
17:34 What happened when Brent told readers he was wrong
21:06 Why buy and hold forever deserves a closer look
26:00 How to combine small trading edges and investing skills
32:56 Holding a currency for hours versus owning a small business
37:00 Why Ian changed his starting position size
42:29 How often does a microcap recover from a 60% drop?
46:57 How Brent sizes trades, sets stops, and decides when to try again
54:04 Trading opportunities too small for institutions
1:01:00 How looking past two quarters can give a microcap investor an edge
1:05:34 When meeting a CEO changes Ian's view of a stock
1:09:59 The 65-cent stock behind the iPhone screen protector
1:15:12 What Brent found when he graded trades by conviction
1:21:45 Why Matt wanted these two strangers to meet

What can Rise Against's Tragedy Plus Time tell us about resilience, optimism, and the American experience? In this episode of the Cultish Creative Music Club, Matt Zeigler and Joseph Moore explore Guy Penn's song selection and what its lyrics reveal about a generation navigating uncertainty, emotional struggles, and the belief that tomorrow can be different.

The conversation moves from punk rock and the familiar sound of 2000s radio to changing ideas about masculinity, the emotional baggage we bring to music, and why a song you would normally skip might have something important to say about your own life.

Topics covered:

• Why Guy Penn chose Tragedy Plus Time to represent American resilience and the possibility of change
• Rise Against's melodic hardcore roots and Matt's reaction to the sound of mainstream 2000s rock
• How generational expectations around masculinity, vulnerability, and therapy shape the hosts' interpretation of the song
• Why the same lyrics might land differently as a Jason Isbell song
• The idea of audio baggage and how musical taste can keep us from hearing a song's message
• Upbeat melancholy: energetic music paired with lyrics about loneliness and uncertainty
• How 100 gecs, hyperpop, and TikTok reflect a different approach to musical influences
• Why music from an uncomfortable period of life can feel a little too familiar
• Whether Tragedy Plus Time earns a place in the club's American life playlist

Timestamps:

00:00 Finding songs that capture American life
05:14 Guy Penn's case for resilience in Tragedy Plus Time
11:53 Generational identity, vulnerability, and growing up
16:06 Audio baggage: why a song's sound changes its meaning
21:03 From 2000s rock to hyperpop and TikTok
25:12 The verdict: a song that hits too close to home

The Cultish Creative Music Club is a Just Press Record series exploring American life through the songs people choose and the stories behind them.

Have a song that belongs in the club? Share your pick and tell us why in the comments.

John Mellencamp's "Jack and Diane" captures the dreams, romance, and uncertainty of growing up in small-town America. In this episode of the Cultish Creative Music Club, Matt Zeigler and Joseph Moore explore the song's lyrics, iconic guitar riff, and surprising production story to understand what it reveals about American life.

Nominated by Julia Duthie (a pitch from England!), the song sparks a conversation about road trips, teenage freedom, economic change, and the choices that shape our lives. From the meaning behind Bobbie Brooks clothing to Kenny Aronoff's unforgettable drum fill, Matt and Joseph uncover the layers beneath a familiar classic and ask whether the America it describes still exists.

@josephmoorebooks + @peopleareeverything

Topics covered:

• Why Julia Duthie chose "Jack and Diane" as the soundtrack to her American road trips.
• How Mellencamp captures the tension between youthful possibility and the realities of growing older.
• The choice between leaving a small town and staying where you grew up.
• How the reference to Bobbie Brooks clothing opens a conversation about American manufacturing and globalization.
• The pedal tone that holds the song's iconic guitar riff together, demonstrated by Matt.
• Why the chorus interrupts the romantic verses with a reminder that time keeps moving.
• How studio experimentation and the influence of Phil Collins helped transform a folk song into a pop recording.
• Kenny Aronoff, drum machines, and the challenge of preserving a human contribution as technology changes music.
• What an outsider's perspective can reveal about American opportunity and identity.
• Tom McGovern's memorable chili dog parody of "Jack and Diane."

Timestamps:

00:00 Finding songs that capture American life
01:22 Introducing Julia Duthie
02:56 Why Julia chose "Jack and Diane"
05:28 American road trips and the power of musical memories
07:27 Teenage dreams and American optimism
09:45 The cautionary tale beneath the nostalgia
11:29 Small-town life and the question of leaving
12:53 Bobbie Brooks and the changing American economy
15:29 Guitar lesson: The pedal tone behind the iconic riff
17:35 Romantic verses and a chorus that interrupts the dream
19:40 Recording a heartland song in Miami
22:23 Turning a folk song into a studio-built pop record
23:35 Phil Collins, drum machines, and Kenny Aronoff
26:26 Technology and the struggle to preserve human creativity
27:43 The lifelong crossroads of leaving or staying
28:37 Seeing America through an outsider's eyes
29:35 Tom McGovern's chili dog parody