How I Built This

26 episodes scanned. 9% of ad slots promote the show's own products.

Recent Episodes

1. Airbnb CEO Brian Chesky: “I Was a Great Founder and a Terrible CEO”

   Nov 2, 2026

   Airbnb co-founder and CEO Brian Chesky discusses his path from art school to leading a company valued above $100 billion, and his view that Airbnb succeeded in spite of his early leadership. He covers the loneliness and inner crisis he felt after the 2020 IPO, how COVID cut the company's business by about 80%, and how he rebuilt his approach to leadership. The episode also covers Airbnb.org's free-housing program for disaster evacuees, refugees, medical stays, and domestic violence survivors.

2. Advice Line with Tope Awotona of Calendly

   Oct 29, 2026

   Tope Awotona, founder and CEO of the scheduling platform Calendly, returns for the final episode of the Advice Line to answer business questions from four callers. The callers are a London bike-helmet maker, a Vancouver pet-gear founder expecting her first child, a South Carolina nail salon owner, and a Boston custom footwear company. Awotona also discusses Calendly's new AI scheduling assistant, Cali, and how he has come to prioritize building around customers rather than products.

3. FIGS: Trina Spear and Heather Hasson. The $2.5 Billion Scrubs Brand That Investors Said Would Never Work

   Oct 26, 2026

   Trina Spear and Heather Hasson, co-founders of FIGS, describe how they built a healthcare apparel brand from Heather's early scrub designs and sidewalk sales out of a car to a publicly traded company. The conversation covers Heather's path from a Kenya uniform project to the first FIGS scrubs, Trina's decision to leave Blackstone and invest her retirement savings, and the investor rejections they faced. It also addresses the 2021 IPO, the stock's volatility, the cost of defending a competitor lawsuit, pandemic-era PPE work, and how they think about luck, resilience, and self-worth.

4. Advice Line with Seth Berkowitz of Insomnia Cookies

   Oct 22, 2026

   Insomnia Cookies founder and CEO Seth Berkowitz returns to the Advice Line to discuss his plan to grow the late-night bakery chain from about 390 company-owned locations toward 1,800 without franchising. He explains why he grows only once consumer demand has been earned, and he advises three callers: a fashion founder rebuilding her brand, a sauna hat company seeking channels for education and sales, and a collegiate clear-bag brand weighing buyer versus user marketing.

5. Sweet Loren’s: Loren Castle. How A Recipe Makeover Built a National Cookie Brand

   Oct 19, 2026

   Loren Castle, founder and CEO of Sweet Loren's, traces how a cancer diagnosis in her early twenties, a job at Levain Bakery, and farmers market sales led her to launch refrigerated cookie dough. She describes how a Whole Foods meeting, customer requests, and a reformulation without gluten, dairy, eggs, and nuts turned the company into a national brand sold in more than 30,000 stores. The conversation also covers her decision to grow slowly and remain privately held.

6. Advice Line with Tara Bosch of SmartSweets

   Oct 15, 2026

   Tara Bosch, founder of SmartSweets, returns to the Advice Line to discuss her new venture, Snackish, a high-protein potato chip brand she started with her daughter's vision. She also joins host Guy Roz in advising three callers: a Chicago marshmallow brand weighing grocery expansion against its direct-to-consumer sales, a Hawaii swimwear label refining its sustainability story, and a Los Angeles experience subscription box testing its model. The conversation covers retail versus DTC channel strategy, product and ingredient choices, and how she approaches building a company the second time.

7. Alamo Drafthouse Cinema: Tim and Karrie League (2023)

   Oct 12, 2026

   Tim and Karrie League, co-founders of Alamo Drafthouse Cinema, trace how a 1993 movie theater lease in Bakersfield, California, led to a national chain known for serving dinner with films. The conversation covers their early failures, the business's growth and location strategy, a 2017 sexual harassment controversy and the company's response, and the COVID-19 shutdown, Chapter 11 bankruptcy, and sale to Sony Pictures Entertainment. The episode is a rebroadcast from spring 2023.

8. Advice Line with Nick Green of Thrive Market

   Oct 8, 2026

   Nick Green, co-founder and CEO of Thrive Market, returns to the Advice Line to answer three caller questions from founders of a concert attire brand, a mission-driven coffee brand, and a speech-loss app. He discusses balancing quality with speed and scale, funding growth without compromising mission, and building awareness through clinicians, advocacy groups, and word of mouth. The episode also covers how Thrive Market uses data and AI, including an AI cart builder, to shape its product and onboarding.

9. 10 Years of How I Built This: A Decade of Innovation, Risk and Reinvention

   Oct 5, 2026

   A 10-year anniversary retrospective of How I Built This featuring host Guy Raz and Ring founder Jamie Siminoff revisiting memorable moments and lessons from over 600 founder interviews. The episode explores key themes including the difference between fear and danger, the importance of identifying problems others share, the role of luck versus skill in entrepreneurial success, and the emotional realities of building businesses. Through clips and discussions, they highlight stories from founders like Sam Caglioni (Dogfish Head), Katrina Lake (Stitch Fix), Eileen Fisher, Paul Orfalea (Kinko's), Justin Gold (Justin's Nut Butters), Danny Meyer (Shake Shack), Toby Lutke (Shopify), and Drew Houston (Dropbox).

10. Advice Line with Scott Tannen of Boll & Branch and Jamie Siminoff of Ring (2025)

    Oct 1, 2026

    An Advice Line episode featuring two high school friends—Scott Tannen, CEO and co-founder of Boll & Branch, and Jamie Siminoff, founder of Ring—answering questions from three early-stage entrepreneurs. The founders discuss bootstrapping versus taking investor capital, scaling retail and wholesale simultaneously, and expanding product awareness beyond traditional channels, while emphasizing customer trust and simplicity as core business principles.