Trading Secrets

Jason Tartick and the Curious Canadian are back for another 30-Minute Thursday covering everything from Jared Freid’s relentless approach to success to Apple’s brand-new $2,000 foldable iPhone.

The guys break down the biggest business takeaways from Jared’s return to Trading Secrets, including why asking for what you want, being scrappy, and putting yourself out there can create opportunities. They also debate whether the new iPhone is actually worth the price, talk podcast negotiations, the rise of athletes in pop culture, the US Open, football season, and the latest sports headlines.

Then, for the first time ever, a Trading Secrets listener joins the show. Taylor Fraser shares her journey from accounting to teaching, how she turned her side hustles into a growing business, and how she and her husband launched Bluegrass Flow, a cold-pressed juice company now sold in 60+ retail locations.

Taylor also opens up about teacher compensation, retirement, AI in education, entrepreneurship, using grants to fund a growing business, and the importance of building a career around something you genuinely love.
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This week, Jason is joined by stand-up comedian, podcaster, and now first-time author Jared Freid for a conversation about the business behind comedy, betting on yourself, and how money, confidence, and relationships are more connected than we think.

Three years after his first appearance on Trading Secrets, Jared returns with his second Netflix special, The Family Plan, and breaks down exactly what it took to get there. After spending roughly $80,000 producing his first special, Jared reveals why he invested around $100,000 of his own money into the second, how the licensing economics work, why he partnered with Betches for marketing power, and why that partnership means splitting the licensing fee 50/50. He also shares why landing in Netflix’s Top 10 in the U.S. and Canada for nearly a week still wasn’t enough to guarantee Netflix would finance his next special.

Jared also opens up about the economics of his growing comedy career, revealing that touring and the U Up? podcast are currently his two biggest financial drivers. He breaks down the ownership structures behind U Up? and JTrain, why subscriptions have become increasingly important to podcasting, and why paid social partnerships remain more of a bonus than a core piece of his business.

Beyond comedy, Jared gets candid about writing his first book, Walking Red Flag, including spending two years on the project, realizing after his first page that he needed a ghostwriter, and paying that expense out of his book advance. He also shares how stepping away from alcohol, his experience with GLP-1s, and rebuilding his relationship with his girlfriend changed his confidence and outlook on life.

From investing six figures into your own career to prenups, joint finances, ghosting, dating economics, protecting what you’ve built, and why Jared says he’s never regretted taking a risk—this episode breaks down what it really looks like to build a career without waiting for someone else to give you your big break.

Host: Jason Tartick
Audio: John Gurney
Video: Marc Colcer
Guest: Jared Freid

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Jason Tartick and the Curious Canadian, David, are back together for another chaotic 30-Minute Thursday—and they have a lot to unpack.

From Jason’s trip to the U.S. Open and the eye-popping $108 million prize pool, to the $23 Honey Deuce and the bizarre world of Burning Man, the guys cover it all. They also dive deep into AI, the fear of giving bots access to our personal lives, the future of work and parenting, and how social media algorithms are increasingly shaping—and sometimes hijacking—our brains.

Plus, they break down the latest Dancing with the Stars cast, debate whether Jason and David could survive Burning Man, talk about finally getting into Harry Potter, and reveal what they’re trying to do to take back control of their algorithms.
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Mary Holland Nader has lived two very different lives—and somehow built both at the same time.

On this episode of Trading Secrets, Jason Tartick sits down with Mary, one of the Nader sisters from Hulu’s Love Thy Neighbor, to unpack her unconventional journey from Wall Street to reality TV, modeling, content creation, and entrepreneurship.

Mary shares what it was really like starting at Deutsche Bank fresh out of college with a $100K salary, working her way into wealth management, and secretly juggling her finance career with modeling and brand deals. She reveals the moment a $5,000 modeling job made her calculate her hourly rate—and realize her side hustle could eventually out-earn her Wall Street salary.

The conversation goes deeper into Mary's decision to leave the security of a steady paycheck, healthcare, and corporate career to pursue entertainment and build her fintech startup, Mary & Pip. She opens up about the financial realities of becoming an entrepreneur, managing unpredictable income, negotiating alongside her sisters, and the freedom that came with finally controlling her own schedule.

Jason and Mary also dive into the rapidly changing world of AI—from how she uses Claude, AI agents, and automation in her everyday life to why she believes emotional intelligence and relationships may become more valuable as technology reshapes the workforce. Mary also shares her perspective on protecting your financial information online and why you should think twice before giving sensitive data to an AI tool.

Plus, Mary breaks down what it's like watching the Nader sisters' rise happen almost overnight, how Love Thy Neighbor changed her career, what goes on behind the scenes with executive producers, and where she wants to take her career next.

From Wall Street to reality TV to fintech, this is a conversation about taking risks, following curiosity, and knowing when it's time to bet on yourself.
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David the Curious Canadian may have overdone it on the beers and hot dogs, leaving Jason Tartick with no choice but to host this week’s Trading Secrets 30-Minute Thursday solo. Jason takes over the mic, covers the biggest pop-culture stories of the week, and shares what’s coming next for him.
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