When Seth Berkowitz was in college, he was the cookie guy on campus. He’d grown frustrated that the only food he could get delivered late at night were standards like pizza or Chinese food. He had a sweet tooth, and he craved warm, homemade chocolate chip cookies. So he took matters into his own hands and started making and delivering cookies to students at his school. The operation soon went from a silly side hustle to a real business - and then an all-consuming struggle. But today, after decades of detours, long-shot decisions, and near-bankruptcies, Insomnia Cookies is now a $350 million dollar business.

This episode was produced by Alex Cheng with music composed by Ramtin Arablouei. It was edited by Andrea Bruce with research help from Katherine Sypher. Our audio engineers were Robert Rodriguez and Maggie Luthar.

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Ring founder Jamie Siminoff joins Guy on the Advice Line, where they answer questions from three founders about balancing short- and long-term goals.  

Today, we meet Vico, an industrial designer in southern California who's launching a crowdfunding campaign for his patented ergonomic desk. Then Iyin, a Baltimore-based product specialist seeking to balance accessibility and profitability for her ethically-sourced chocolate brand. And Franchesca, an Atlanta area educator deliberating whether to pursue small-business certifications for her motivational classroom posters.

If you’d like to be featured on a future Advice Line episode, leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to [email protected] or call 1-800-433-1298.

And be sure to listen to Ring’s founding story as told by Jamie on the show in 2020.

This episode was produced by Carla Esteves with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Neal Rauch.

You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

With $1500 in savings and no experience in retail, Mel and Patricia Ziegler stumbled upon a clever idea: buy inexpensive Army surplus gear, refashion it into stylish clothes, and sell them in a setting that felt more like a safari than a store. With a retro- feel catalog that turned shopping into an adventure, Banana Republic caught the attention of the media, and sales grew. But so did the headaches of running the business, and in 1983, the Zieglers sold the brand to The Gap. Over the years, Banana Republic lost its distinctive, retro-Safari feel, and the Zieglers departed to start another brand, The Republic of Tea. Today, Banana Republic remains a multi-million dollar business, with hundreds of stores around the world.

This episode was produced by Kerry Thompson with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineer was Kwesi Lee.

You can follow HIBT on Twitter & Instagram and sign up for Guy's free newsletter at guyraz.com.

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Supergoop! founder Holly Thaggard joins Guy on the Advice Line, where they answer questions from three founders about finding the right audience and introducing their brands.

Today, we meet Christina, the founder of a Cincinnati cookie business who is trying to bake her business to the next level. Then Philadelphia-based engineer Andy introduces a shaving product he developed with his Navy bunkmate while they were deployed. And Erin in Illinois, who wants to make water sports safer with a  life jacket upgrade.

If you’d like to be featured on a future Advice Line episode, leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to [email protected] or call 1-800-433-1298.

And be sure to listen to Holly tell the story of how Supergoop! was founded from her first visit to the show back in 2020.

This episode was produced by J.C. Howard with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Gilly Moon.

You can follow HIBT on Twitter & Instagram and sign up for Guy's free newsletter at guyraz.com.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In 2013, Nick Green set out to solve a vexing problem: in many parts of the country, it’s hard to get access to healthy groceries. As a solution, Nick and his co-founders launched an e-commerce mashup of Whole Foods and Costco, where members purchase healthy foods online at a discount.

When it came time to ask venture capitalists for funding, dozens of VC’s said no–but thanks to hundreds of small checks written by health bloggers, Thrive Market pulled together enough money to launch in 2014. Within a year, the founders had proven the VC’s wrong, but still scrambled to fuel the pace of growth, while keeping the business afloat. Today, Thrive Market has over 1.5 million paid members and, last year, brought in over $500 million in sales.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Boston Beer Company founder Jim Koch joins Guy on the Advice Line, where they answer questions from three founders about finding product-market fit.

Today, we meet Kim, whose tropical-inspired apparel company in Florida is venturing into the rum market. Then Llance from Washington, who is taking his tea-bag-soup-broth business national. And Ami, who wants potential customers to know that her Ontario-based electrical contracting company has some of the best service out there.

If you’d like to be featured on a future Advice Line episode, leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to [email protected] or call 1-800-433-1298.

And be sure to listen to Boston Beer Company’s founding story as told by Jim on the show in 2017.

This episode was produced by Chris Maccini with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Gilly Moon.

You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Tara Bosch wasn’t always considered a likely contender for success. At 21 years old, she dropped out of college the summer before her junior year and moved in to her grandmother’s basement. But, with a gummy bear mold from Amazon and a sugar-free candy recipe she tinkered to perfection, Tara got to work on a wild vision: she would create a global company called SmartSweets that would revolutionize the candy aisle and become a top seller of low-sugar candies. In 2020, Tara achieved her goal and sold SmartSweets for $360 million — a mere five years after creating the brand.  

This episode was produced by Carla Esteves with music by Ramtin Arablouei. It was edited by Andrea Bruce with research help from Melia Agudelo. Our audio engineers were Gilly Moon and Maggie Luthar.

You can follow HIBT on X & Instagram, and email us at [email protected]. And sign up for Guy’s free newsletter at guyraz.com.

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Harry’s and Warby Parker co-founder Jeff Raider joins Guy on the Advice Line, where they talk with three founders grappling with strategic decisions.

Today we meet Uli, who’s trying to balance multiple revenue streams for her Los Angeles-based gelato business. Then Travis in Boulder, who just hired his first employee for his upstart package delivery service. And Karly from southern California, who’s launching a children’s book subscription that makes the full moon more magical.

If you’d like to be featured on a future Advice Line episode, leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to [email protected] or call 1-800-433-1298.

And to hear the founding story of Harry’s, check out Jeff's first appearance on the show in 2023.

This episode was produced by Alex Cheng with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Neal Rauch.

You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Mike Sinyard helped put mountain biking on the map. In the 1970’s, he founded Specialized Bicycle Components to do exactly what the name suggests: sell high-quality bike parts. He eventually decided to make his own models, becoming a pioneer in the industry by designing the first mass-produced mountain bikes. By the 1990’s, Specialized was pulling in tens of millions of dollars in revenue, and Mike brought in outside experts to help grow the business. That turned out to be a huge mistake; Mike spent the next few years recovering from bad business decisions, and recalibrating the company after near bankruptcy. Today, Specialized has regained its reputation as an industry leader, and does around $500 million in sales per year.  

This episode was produced by J.C. Howard, with music by Ramtin Arablouei

Edited by Neva Grant, with research help from Katherine Sypher.

You can follow HIBT on Twitter & Instagram, and email us at [email protected].

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What does it take to successfully market a brand today? Last month, Guy sat down with marketing expert Jim Stengel to find out.

Jim spent more than two decades at Procter & Gamble, where he managed international brands like Jif and Pampers. He spent seven years as P&G’s Global Marketing Officer.

Today, he consults with businesses large and small, and interviews marketing leaders on his show, The CMO Podcast.

This interview was recorded in front of a live audience on the Amazon stage at Cannes Lions International Festival of Creativity, and was supported by Wondery.

This episode was produced by John Isabella with music by Sam Paulson. It was edited by Neva Grant. Our audio engineers were Cena Loffredo and Debbie Daughtry. 

You can follow HIBT on X & Instagram, and email us at [email protected]. And sign up for Guy’s free newsletter at guyraz.com.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.