How I Built This with Guy Raz

In this engaging discussion, Chris Riccobono, the founder of UNTUCKit, shares his entrepreneurial journey from a GE salesman frustrated with dress shirts to launching a successful clothing brand. He details the challenges of creating the perfect untucked shirt and overcoming manufacturing hurdles. Chris highlights pivotal moments like a risky shift to physical retail in Soho and a transformative radio ad campaign. He also reflects on navigating the brand through financial hardships during the COVID-19 pandemic, showcasing resilience and adaptability in the ever-changing fashion industry.

Marcia Kilgore, a serial entrepreneur and founder of popular brands like Beauty Pie, shares valuable insights on overcoming entrepreneurial challenges. She addresses pressing questions from founders navigating fears of failure and maintaining customer excitement. Listeners learn about innovative pricing strategies, effective engagement techniques, and the role of failure in building resilience. The conversations emphasize the importance of customer feedback and adapting in a competitive landscape, making it a treasure trove of advice for aspiring business owners.

Dylan Field, co-founder of Figma, started his journey in design collaboration after dropping out of Brown University to pursue a Thiel Fellowship. He discusses the early challenges of monetizing Figma and the innovative features that revolutionized design workflows. Dylan shares his personal experiences of navigating skepticism, managing a young team, and the transformative moments that shaped his leadership. He reflects on the delicate balance of luck and hard work that led to Figma's notable growth, including its $20 billion acquisition bid from Adobe.

Perry Chen, co-founder of Kickstarter, lends his expertise to early-stage founders facing critical decisions. Joe Fontana shares his vision for Fry the Coop and how he navigates growth in the competitive food industry. Jesse Hodge grapples with whether to sell his cold plunge business, while Catharine Kerbis seeks strategies for scaling her hot sauce brand without heavy investment. The guests dive into the emotional ups and downs of entrepreneurship, discussing personal aspirations versus business goals, and the importance of community support.

Bill Keith and Leigh Keith, co-founders of Perfect Snacks, share their extraordinary journey from a nomadic childhood to building a successful snack empire. They explore the emotional and financial challenges they faced, including product recalls and their father's health decline. The duo recount how a beloved family recipe for peanut butter bars became the foundation for their business. With tales of resilience and creative sales strategies, they highlight the importance of family support and the lessons learned along the way.

Mark Ramadan, co-founder and former CEO of Sir Kensington's, shares his journey in disrupting the condiment market. Lucas Manteca discusses how his Taco Shop differentiates itself from giants like Chipotle through community engagement and quality ingredients. Beth Benecke highlights her experience navigating the challenging 'messy middle' of scaling her baby products brand. The trio dives into retail challenges, innovative marketing, and the importance of seeking support while crafting their unique entrepreneurial identities.

Vicky Tsai, founder of Tatcha, shares her inspiring journey from a corporate job to creating a skincare brand rooted in Japanese beauty rituals. After a transformative trip to Japan and an unforgettable encounter with a geisha, she defied skepticism to launch Tatcha from her parents' garage. Vicky discusses the trials of self-funding and launching a unique beauty product in a skeptical market, alongside her emotional growth and the brand's eventual $500 million acquisition by Unilever, showcasing resilience and the power of believing in one’s vision.

Steve Holmes, Founder of Springfree Trampoline and Goba Sports Group, shares valuable insights for early-stage entrepreneurs tackling unique challenges. He offers guidance on navigating tariffs for manufacturers and emphasizes the importance of identifying core customer segments. Discussions range from creating inclusive activewear to developing year-round strategies for seasonal products like bug repellant. Additionally, Holmes highlights the journey of a Caribbean-inspired chocolate brand, showcasing innovative marketing strategies and the impact of personal resilience in entrepreneurship.

Michael Acton Smith, co-founder of Calm and creator of Moshi Monsters, and Alex Tew, known for the Million Dollar Homepage, share their journey transforming meditation into a thriving app. They discuss overcoming skepticism from investors and the road to securing calm.com. The duo reflects on the rise of community-driven ventures, emphasizing creative marketing and the importance of innovative content. Their lighthearted camaraderie shines through as they highlight the joy and passion behind building a platform that promotes mental well-being.

Andy Atkins, co-owner of Bad Luck Burger Club, shares his thoughts on the potential of a brick-and-mortar expansion from his Nashville food trucks. Tiffany Narbonne, founder of T. Jazelle, discusses her journey in creating inspirational jewelry and her aspirations to partner with larger retailers. Peter Houck, founder of RinkRabbit, evaluates the prospects of international growth for his figure skating accessories, emphasizing the need for a solid domestic foundation. All three guests offer unique insights into navigating business challenges and scaling their brands.