Entrepreneur, author, and podcaster Tim Ferriss joins Guy on the Advice Line to answer questions from three early-stage founders. Plus, Tim shares the inspiration behind his latest venture, Coyote—a 10-minute card game that encourages time spent with friends and family.

First, Lauryn from San Francisco asks about the best way to scale her biodegradable ear plugs in two very different directions. Then Emily from Kansas City weighs whether DTC or wholesale is where to focus her accessory brand after Taylor Swift wore one of her rings and sales exploded. And finally, Kimberly in Woolwich, Maine wonders how to incentivize her customers to pre-order her high-quality, sustainable, clothing.

Thank you to the founders of GOB, EB & Co, and K. Becker Designs for being a part of our show.

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 hibt@id.wondery.com or call 1-800-433-1298.

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

This episode was produced by Noor Gill with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineer was Cena Loffredo.

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

In 1978, Brian Smith quit his accounting job in Australia and headed to California with a surfboard, some savings, and ambition. He figured California was where he’d find an idea or a product to bring back home to Australia to build a business. A year in, he was still looking..

But then he saw an advertisement in a surfing magazine for Australian sheepskin boots. Uggs were so widespread in Australia at the time, the name was a generic term - like flip flops - not a brand. Brian was immediately stoked: these boots were virtually unknown in America. If he could get ugg boots for sale in the U.S., they would be a huge success! Almost nobody else agreed.

For years, Brian lived on the edge of collapse. He sold boots from the back of his van and worked construction and golf course maintenance jobs to survive. Retailers laughed him out of stores. He lost control of his company twice. At one point, he literally crawled across the floor from stress, ready to walk away forever.

And yet…he kept going.

What followed was one of the most unlikely brand-building stories in modern retail history — involving surf culture, trademark wars, miraculous timing, brutal financing mistakes, and a product the fashion world initially dismissed.

Today, UGG generates more than $2.5 billion a year in sales.

You’ll hear how Brian:

• Turned rejection into problems to solve
• Discovered marketing insights that changed UGG forever
• Survived years of cash-flow disasters
• Lost control of the company and regained it a couple of times.
• Used surf culture to build an emotional connection with customers
• Nearly quit… over and over again…
• And how he eventually sold UGG to footwear giant, Decker

Timestamps:

• 07:26 Brian's eureka moment that led to the birth of UGG
• 10:16 The first sales trip results in ZERO sales
• 18:45 The mantra that kept Brian going while doing odd summer jobs to survive
• 26:07 Brian gets a critical lesson in marketing…from some 12-year-old kids
• 47:19 Brian’s most effective strategy for retail: the “Six-Pair Stocking Plan”
• 52:02 On track to regain his ownership - Brian hits a huge snag
• 57:17 A midnight phone call from Australia saves the business
• 01:05:18 Brian gets the last laugh in the trademark dispute - and acquires a boot factory
• 01:08:44 Pamela Anderson wears UGGs on the set of Baywatch
• 01:17:29 A chance meeting in the Atlanta airport leads to a deal to sell UGG

This episode was researched and produced by Casey Herman, with music by Ramtin Arablouei, and edited by Andrea Bruce.

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Today’s callers: Kristina in Ohio looks for avenues beyond organic social media to market her furniture designed for toddlers and parents alike. Then Phil in Michigan considers the best messaging to brew interest in his farm-made cherry vinegar. And Caroline in California scouts new ways to cultivate curiosity around her plant-based dog food.

Plus, Jeffrey discusses the quiet momentum of social businesses as they navigate ‘greenhushing’ and a polarized political climate.

Thank you to the founders of Twenty Five and Pine, Red Truck Orchards, and Petaluma for being a part of our show.

If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—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 hibt@id.wondery.com or call 1-800-433-1298.

And be sure to listen to Seventh Generation’s founding story as told by Jeffrey and his co-founder Alan in 2021.

This episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Jimmy Keeley.

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

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