The School of Moxie Podcast
Three seasons. Three experiments in how we tell stories about business.
The School of Moxie isn't really an interview show, even when I'm interviewing people. Mostly because we’re talking about our businesses through the lens of pop culture and media.
Each season begins with a question I want to investigate, a set of constraints around how we're going to investigate it, and usually an idea that makes considerably more sense once you come along for the ride.
The result is part business podcast, part cultural analysis, and part ongoing documentation of me changing my own mind in public.
And yes... every season is different on purpose.
Season 1: The Last of Us
Yes, it's a business story. And once you see it, you won't be able to unsee it.
For the first season of The School of Moxie, I gave every guest an episode from Season 1 of HBO's The Last of Us and asked them to use it as the starting point for a conversation about business.
There was one other rule: every conversation had to happen in person, across a table from me.
That turned the season into an experiment in more ways than one. I recorded conversations in Vancouver and Portland, Los Angeles, Denver, Richmond, and even Nice, France, exploring what a story about survival, relationships, identity, power, loss, and the choices people make under pressure could show us about the way we build businesses.
Somewhere along the way, the experiment showed me something else: I didn't just care about what we were recording. I cared deeply about how and where we were recording it, and what became possible when people were physically present together.
Season 1 is the season that made me realize I wanted to build Sasquatch Media Grounds.
Season 2: Ted Lasso
What happens when the industry teaching people how to lead businesses has a leadership problem of its own?
Season 2 is a solo season, and it is intentionally uncomfortable.
Using the leadership lessons woven throughout Ted Lasso as a lens, I took a hard look at the online coaching industry, the ways it had evolved, and the sales and business practices we had collectively learned to treat as normal.
This season asks difficult questions about coercive sales tactics, boundaries, power, belonging, and what happens when the container that's supposed to help people grow begins asking them to override their own judgment instead.
I'm not examining any of this from a safe distance. Throughout the season, you can hear me confronting my own participation in the industry and reconsidering the business I had built inside it, including my decision to shut down my own high-ticket mastermind while I searched for a better way to support the people who trusted me to help them.
It isn't a tidy retrospective with all the answers conveniently figured out beforehand. It's a record of a shift while it was happening.
Season 3: Comfort Shows
You make decisions differently when your business actually has to pay the bills.
By Season 3, Sasquatch Media Grounds existed. I had a brick-and-mortar studio, a much clearer idea of the media I wanted to make, and another question I couldn't stop thinking about.
So I created one very specific casting rule: to be a guest this season, your own work had to make you financially and economically self-sufficient.
No spouse or partner subsidizing the household while the business found its footing. No second job quietly providing the dependable income. No other financial engine making it possible to wait indefinitely and see whether entrepreneurship worked out.
That distinction isn't a judgment about who is or isn't a “real” entrepreneur. In fact, some extraordinary founders answered the casting call who had supported themselves entirely through their businesses in the past or were navigating major transitions when we recorded, and I want to find other places to tell those stories.
But they weren't the subjects of this experiment.
Season 3 brings together ten episodes with ten female founders who are supporting themselves through their work. Nobody has the perfect business. Nobody has everything figured out. They're making different choices, building different models, and defining success on their own terms.
Collectively, though, they reveal something I think we talk about far too little in entrepreneurship: the absence of a safety net changes the calculus.
You price differently. You spend differently. You assess risk differently. You decide what deserves another six months and what needs to die on Tuesday.
And when you listen to all ten conversations together, a much more complicated picture of entrepreneurship emerges than the one we're usually sold online.