Advice Line with Curt Richardson of OtterBox

More from How I Built This with Guy Raz

1. 

   E858 · 3 Aug 2026 · 1 hr 16 min

   Serena & Lily: Serena Dugan and Lily Kanter. They Built a $20M Brand—Then One Investor Almost Destroyed It

   Many founders think the hardest thing about business is finding customers.It's not.It's surviving success.When Lily Kanter and Serena Dugan launched a luxury baby linen business, they had no manufacturing experience, no inventory, and barely any capital. But after their first catalog landed just as a major competitor left the market, orders flooded in almost overnight.The problem? They hadn’t made the products yet. Today, Serena and Lily has grown into one of the best known luxury home goods brands in the country. But getting there was a grind. This is one of the most revealing conversations…

2. 

   E857 · 30 Jul 2026 · 46 min

   Advice Line with Chris Riccobono of UNTUCKit

   Today’s callers: Adrian from California wants to grow his apparel company to complete with big-name athletic brands. Then, Preet from the Rockies looks for strategies to reach seniors and their children with his daily check-in app. And Derek from Virginia considers social media and professional partnerships to advertise his hockey equipment brand. Plus, Chris talks about launching a new athletic apparel brand while continuing to grow UNTUCKit.Thank you to the founders of Eras Shorts, Snug Safety, and Hockey Ninja for being a part of our show.If you’d like to be featured on a future Advice…

3. 

   E856 · 27 Jul 2026 · 1 hr 12 min

   Sweetwater: Chuck Surack. How a Customer Service Strategy Built a Billion Dollar Online Pro Audio and Music Company.

   Chuck Surack never planned to build one of America's largest online retailers. He just wanted to be a musician. So right after high school, he took his sax and drove off in his old VW van to play gigs around the country. It didn’t work out. But with the audio and mixing skills Chuck learned gigging, he decided to convert his van into a mobile recording studio - and started making money fast by making recordings of local bands, businesses, and schools.The game-changer came as a one-two-three punch: first, he created a new product - digitized sound libraries - to sell nationally; second, he…

4. 

   E854 · 20 Jul 2026 · 51 min

   Toast: Aman Narang. How a Long Wait for the Dinner Check Launched a $2 Billion Business.

   After waiting too long to pay his restaurant bill, Aman Narang thought there had to be a better way. His first idea—a mobile payment app—flopped.But that failure revealed a much bigger opportunity.Restaurants were struggling with outdated software that many owners hated. Payment systems were expensive, unreliable, and trapped on servers hidden in back offices. Replacing them cost time and money.But that’s exactly what Aman and his co-founders set out to do: create an entirely new POS system for restaurants—from scratch.They worked from an unfinished basement, answered customer calls on their…

5. 

   E853 · 16 Jul 2026 · 46 min

   Advice Line with Kenneth Cole

   Today’s callers: Matt from New York City unpacks the stigma working against his line of foot wellness products. Then Emefa in Toronto seeks a direct relationship with customers of her fashion brand in the wake of a key retailer going out of business. Finally, Levi in Rhode Island explores new audiences and product lines for his commemorative golf sculpture business.Plus, Kenneth and Guy discuss how to make social impact a real part of your business model.Thank you to the founders of Pedestrian Project, ISRAELLA KOBLA, and Swing Sculpt for joining us on the show.If you’d like to be featured…

6. 

   E852 · 13 Jul 2026 · 1 hr 16 min

   Sun Bum: Tom Rinks. The Secrets of a Master Brand Builder (2023)

   Tom Rinks got his start in the commission-only "shark tank" of midwestern furniture sales. That’s where he learned what makes customers buy. Decades later, those instincts helped him grow a joke of a side hustle into a $400 million success.In 2009, he created the iconic branding for an obscure sun tan lotion, drawing on a mish-mash of surf culture, Scandinavian furniture, and Japanese streetwear. Sun Bum became a huge success, but even before that, Tom helped boost a wildly diverse range of brands: a line of tequila, a series of Christian videos, and the ubiquitous “Yo quiero Taco Bell”…

7. 

   E877 · 8 Oct 2026 · 44 min

   Advice Line with Nick Green of Thrive Market

   Today’s callers: Mercedes in Utah tries to find harmony between quality and speed as she scales her concert attire brand for musicians. Then Danny in Colorado grapples with the tradeoffs of growing his sustainable and functional coffee brand. And Riya in Illinois wonders how to build awareness for her app that aids people affected by speech loss.Plus, Nick’s insights on how AI is changing the way we fill our grocery carts — and how grocers respond to food and nutrition trends.Thank you to the founders of Blackstrad Concert Attire, Peak State Coffee, and Voice Back for being a part of our…

8. 

   E876 · 5 Oct 2026 · 1 hr 10 min

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

   Stories about starting a business are almost always full of drama. They’re about ambition, loss, triumph, catastrophe, resilience. And they’re also full of life lessons – which is why Guy Raz launched How I Built This 10 years ago: He wanted to host a free master class in entrepreneurship, one conversation at a time. Ten years on, he’s conducted over 600 interviews with some of the world’s most successful founders, and on today’s show, he replays some of the most memorable moments and lessons. Joining him is Jamie Siminoff, the founder of RING and a former guest on the show. Why Jamie? He’s…

9. 

   E875 · 1 Oct 2026 · 46 min

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

   CEO and co-founder of Boll & Branch, Scott Tannen joins Ring founder Jamie Siminoff and Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, Jamie and Guy talk about how creating repeat customers often comes from creating social good. First, we hear from Melita in Toronto who's wondering whether to continue bootstrapping her organic clothing business. Then Eric in the Sunshine State asks which direction to take to grow his sunscreen apparel lines. And Chris in Alpine Meadows, California, is trying to figure out how to get his sleek binoculars into the hands…

10. 

    E874 · 28 Sep 2026 · 1 hr 31 min

    Seventh Generation: Alan Newman and Jeffrey Hollender. A Partnership that Flourished—until it Failed. (2021)

    With its eco-friendly paper towels, diapers, and cleansers, Seventh Generation was one of the first—and most successful—green household brands to hit the market. But in the early 1990s, its two founders had a bitter falling out.Alan Newman and Jeffrey Hollender have barely spoken since that time, but they both agreed to come on the show to talk about the business they were both passionate about, and the delicate nature of partnership.What you'll learn: Why Alan says his great strength—and his greatness weakness—is his tendency to say “yes”How Jeffrey and Alan lost their friendship and…

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