(Almost) Reckless

A conversation with Amy Smilovic and Sherri McMullen. Sherri is the Founder and CEO of McMullen, the independent luxury fashion boutique she opened in Oakland in 2007 and relocated to San Francisco in 2024. Named one of the best boutiques in the country by Vogue and one of the most innovative retailers in the world by Vogue Business, McMullen has spent nearly two decades building its reputation on discovery — championing emerging designers, particularly women and creatives of color, alongside established houses like Dries Van Noten, The Row, and Tibi, which the store has carried since its early days. Before McMullen there was a business degree, a short and clarifying stint in accounting, the executive development program at Neiman Marcus in Dallas, and the launch team for Pottery Barn Kids in San Francisco — where, while building someone else's brand, Sherri began writing her own business plan on a borrowed computer. Throughout the episode, Amy and Sherri discuss the skills required to start a business versus the ones required to keep it alive, what retail math and time on the sales floor taught her that spreadsheets never could, and how a gut feeling she couldn't shake became a store. Sherri remains one of Tibi's longest-standing wholesale partners, having bought the collection for McMullen since its earliest seasons — a relationship that has spanned nearly the entire life of both businesses.

A conversation with Amy Smilovic and Frank Rizzieri. Frank is a celebrated editorial hairstylist, three-time North American Hairdresser of the Year, and the third-generation president of Rizzieri Salons, Spas, and Schools, a family beauty business his maternal grandfather founded in 1924 and that Frank has spent his career modernizing across three generations. The Rizzieri network now operates two flagship salons and spas in Moorestown and Washington Township, New Jersey, the Rizzieri Aveda School in Voorhees, employs more than 185 professionals, and serves over 150,000 clients annually. As an editorial hairstylist, his career has included long-standing runway collaborations with Tibi, Calvin Klein, Helmut Lang, and Cynthia Rowley, alongside work with celebrities including Paul McCartney and Elle Macpherson. Across his salons, schools, and franchise platform, Frank continues to actively shape the next generation of professionals in beauty. Throughout the episode, Amy and Frank reflect on more than two decades of working together - the inheritance of a family business and what it took to honor it by changing it, the moment during COVID when each of them had to redefine what they were fighting for, and the choice both made to build for agency rather than scale.

A conversation with Bobbi Brown and Amy Smilovic. Bobbi is a makeup artist, entrepreneur, New York Times bestselling author, and the founder and Chief Creative Officer of Jones Road Beauty, one of the fastest-growing independent beauty brands in the country. Founded in 2020 alongside her husband Steven Plofker, Jones Road operates under 100% family ownership, with her son Cody serving as CEO. Bobbi is the author of nine bestselling guides to makeup and beauty, and most recently her first memoir, Still Bobbi: Lessons on Building a Beautiful Life. The memoir traces Bobbi's career from her early years as a New York makeup artist through founding Bobbi Brown Cosmetics in 1991, building the brand into a billion-dollar global business under Estée Lauder, and her departure in 2016. Bobbi is also the co-owner of The George, an independent boutique hotel in Montclair, New Jersey. Throughout the episode, Amy and Bobbi reflect on the long arc of their careers - the corporate pressures of working within a brand that bears your name, the scrappy and instinctive origins of building something new, and the role of authenticity in the businesses that last.

A conversation with Amy Smilovic and Jeffrey Saad - Chef, Entrepreneur, Estate Director, and Author. Before Compass, where he and his wife Nadia were among the first six agents in California and now serve as Estate Directors in Beverly Hills, Jeffrey was building restaurants in San Francisco. He opened his first, Sweet Heat, at twenty-four, went on to become Chef/Partner of California's Pasta Pomodoro Italian Restaurants, and broke through nationally in 2009 as the first runner-up on The Next Food Network Star - a run that led to his own web series, Spice Smuggler, and later to United Tastes of America on The Cooking Channel. He's the author of the cookbook Jeffrey Saad's Global Kitchen, the host of The Circle Podcast, and his forthcoming book, The Reduction: How to Cultivate Joy and Build a Life Worth Savoring, arrives in a month.
Amy and Jeff grew up twenty miles apart outside Chicago, married partners who came to America from somewhere else, and built their businesses on the same philosophical scaffolding without ever comparing notes. They get into the personal constitution Jeff wrote at twenty-three and still reads every morning, the difference between first principles, opinions, and tactics, why the burnt edges are what make the steak taste good, and what it actually means to reduce - to distill a life down to the ingredients that matter and refuse the rest. They talk about the trap of storytelling, the gap between incident and reaction, the kind of leadership that refuses to be efficient with people, and what is gained by walking forward instead of looking back. It's a conversation about joy as a discipline rather than a disposition - and about what happens when two people who chose to reduce land at the same table.

A conversation with Checka Propper and Amy Smilovic. Checka is the Head of Television at Color Force, the production company behind The Hunger Games franchise, American Crime Story, and Love Story — the limited series chronicling the relationship between JFK Jr. and Carolyn Bessette-Kennedy that became the most-watched limited series in FX history, accumulating over 65 million hours streamed in its first season.
Throughout the conversation, Amy and Checka discuss what it actually means to build a career from curiosity rather than a plan — how a kid outside Philadelphia who struggled with learning disabilities found refuge in the patterns of television, and how that eventually became the instinct she uses to decide what stories are worth telling. They get into the adjectives Checka uses to evaluate everything from the shows she develops to the networks she develops them for, the difference between following a gut and being able to articulate why the gut is right, and what it looks like to produce one of the most culturally resonant shows of the year — its controversies included — alongside one of Hollywood's most singular creative forces. And because Amy and Checka's relationship began with a DM about personal style in the middle of a pandemic, when Checka felt like she had lost her sense of self somewhere inside a very successful career, the conversation ends where it started: with the question of who you are when the title gets stripped away, and what it takes to find your way back.