329. Jared Freid: The $100K Gamble Behind His Netflix Special, The Business of Comedy & Dating Economics

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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week, Jason is joined by Banfield Pet Hospital Chief Medical Officer Dr. Alea Harrison for a conversation about the real economics of pet ownership, why preventive care can be one of the smartest financial decisions pet owners make, and how planning ahead can help avoid thousands of dollars in unexpected veterinary expenses. Dr. Harrison shares her journey from leaving the country to attend veterinary school in St. Kitts to becoming a practicing veterinarian and eventually helping guide clinical strategy for roughly 3,600 veterinarians across more than 1,000 Banfield hospitals nationwide. Dr. Harrison breaks down what people should actually budget for when bringing home a pet, including veterinary care, nutrition, grooming, training, boarding, and daycare—and why many of the biggest expenses are the ones owners rarely think about beforehand. She explains why choosing the right food should be based on a pet’s individual health, breed, and lifestyle rather than marketing or social media trends, and reveals why taking a proactive approach to veterinary care can dramatically change both a pet’s long-term health and the owner’s finances. Jason and Dr. Harrison also dive into Banfield’s Optimum Wellness Plans, why they were designed to make preventive veterinary care more accessible and predictable, and how they differ from traditional pet insurance. Dr. Harrison explains how bundling preventive services can save clients more than 30% compared to paying for each service individually, while plans can include comprehensive exams, vaccinations, diagnostic testing, unlimited office visits, and 24/7 Pet Chat access. She also explains why pet insurance and wellness plans can work together, with insurance focused on unexpected illnesses, injuries, and surgeries while wellness plans focus on routine preventive care. Plus, Dr. Harrison reveals some of the numbers that show just how expensive waiting can become. Heartworm prevention can cost around $25 per month, while treating heartworm disease can range from roughly $1,200 to $6,000 depending on the pet. She also shares that Banfield data shows 80% of dogs and 75% of cats have signs of dental disease by just one year old, explains how certain breeds can be predisposed to costly health problems, and breaks down why spaying and neutering can help prevent serious conditions and certain cancers in addition to controlling the pet population. Dr. Harrison also gets candid about the challenges of becoming a veterinarian, from the competitiveness and financial burden of veterinary school to building a career that can extend far beyond treating individual patients. She explains how her own definition of impact evolved from caring for pets one-on-one to influencing thousands of veterinarians and ultimately helping improve care on a much larger scale. Dr. Harrison reveals why creating predictability, staying proactive instead of reactive, and preparing for expenses before they become emergencies can make all the difference for pet owners. She also leaves Jason with her ultimate trading secret, a mantra she applies to business, family, and veterinary medicine: “If you stay ready, you don’t have to get ready.” She reveals all this and so much more in another episode you can’t afford to miss! Host: Jason Tartick Audio: John Gurney Video: Marc Colcer Guest: Dr. Alea Harrison Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jason Tartick and the Curious Canadian are back for a 30-minute Thursday episode! The guys recap their conversation with Stephanie Shojaee, dive into why Jason is genuinely terrified of going to the doctor, and unpack everything happening across pop culture right now. From the biggest takeaways from Stephanie’s episode to Jason’s latest fears and the stories everyone is talking about, this is your Thursday dose of Trading Secrets. Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week, Jason is joined by The Real Housewives of Miami standout and Shoma Group president Stephanie Shojaee for a conversation about building massive wealth, growing a multi-billion-dollar real estate business, and why relentless ambition has been at the center of everything she has accomplished. The first-generation Colombian American opens up about growing up determined to become “filthy rich,” eventually helping lead a development company that has completed more than $6 billion in real estate transactions—and using reality TV as a platform to expand the Shoma brand globally. Stephanie breaks down how her approach to money changed after meeting her husband, Masoud, from focusing solely on earning and saving to investing, using debt strategically, and continuously putting capital back to work. She shares how her modern approach to branding and marketing helped increase Shoma’s business by roughly 30%, while expanding its recognition beyond South Florida and into markets including Dubai. She also reveals the unforgettable $240,000 payday she earned after refusing to give up on a deal that fell apart three separate times. Jason and Stephanie also dive into her unconventional leadership style, including building Shoma’s nine-person, all-women Latina marketing team largely with young hires straight out of school. Stephanie explains why she believes in discipline, tough love, and throwing employees “in the pool” to see whether they sink or swim—and why she has no problem moving on quickly when someone isn’t the right fit. Plus, Stephanie gets candid about life on The Real Housewives of Miami, why she originally turned the show down for years, and why representing an ambitious, successful Latina businesswoman ultimately helped change her mind. She also shares the wild story of having more than $200,000 worth of belongings stolen from her villa in Cannes, her thoughts on prenups and combining love and money, and the luxury purchase that recently made her say, “Damn, that was expensive”—an Hermès bracelet costing upwards of $250,000. Stephanie reveals why putting on the blinders, eliminating distractions, investing rather than simply earning, and staying relentlessly focused on your goals have been key to her success. She also leaves Jason with a different kind of trading secret: after 15 years with her husband, never go to bed angry and never allow disrespect to become normalized in a relationship. She reveals all this and so much more in another episode you can’t afford to miss! Host: Jason Tartick Audio: John Gurney Video: Marc Colcer Guest: Stephanie Shojaee Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jason Tartick and the Curious Canadian are back for another Thirty Minute Thursday! The boys recap their conversation with Rachel Mansfield, break down the biggest takeaways from the episode, and dive into everything happening across pop culture. From the latest headlines and celebrity news to the stories everyone is talking about, they cover it all in 30 minutes. Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week, Jason is joined by food creator, entrepreneur, investor, and cadootz! co-founder Rachel Mansfield for a conversation about turning an unexpected firing into a multi-faceted career spanning content, consumer brands, and venture investing. Rachel breaks down getting fired from her $54,000 corporate job after her food blog was viewed as a conflict of interest, giving herself six months to make it on her own, and ultimately surpassing her old salary within that timeframe. She reveals how brand partnerships, affiliate revenue, and evergreen recipe content helped turn her online following into a legitimate business. Jason and Rachel also dive into the economics behind cookbooks and venture investing, including why a $100,000 book advance can disappear quickly when photography alone can cost $60,000–$100,000. Rachel shares how she went from promoting brands to investing in them, eventually launching a venture fund with her husband that has raised roughly $3.5–$4 million and invested across more than 20 brands. Plus, Rachel breaks down building cadootz!, including spending roughly $500,000 developing the product, selling out its first online launch within hours, raising a $3 million seed round, and landing a nationwide Target rollout that has expanded to more than 2,000 stores. Rachel reveals why diversifying your income, building ownership, and constantly finding new opportunities within your niche have been key to her success. She reveals all this and so much more in another episode you can’t afford to miss! Host: Jason Tartick
Audio: John Gurney
Video: Marc Colcer
Guest: Rachel Mansfield Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week on Trading Secrets Thursday, Jason Tartick and the Curious Canadian are back to break down the biggest takeaways from Monday's conversation with Chloe Demrovsky on America's growing home insurance crisis. They recap the discussion on rising insurance premiums, hidden risks homeowners should know about, and why the insurance landscape is changing faster than ever. Then, they shift gears into this week's biggest pop culture stories, including Arizona State University's headline-making decision to offer an Influencer major. Is content creation really worthy of a college degree? Jason and the Curious Canadian weigh the opportunities, the skepticism, and what it says about the future of work. Learn more about your ad choices. Visit podcastchoices.com/adchoices