In 2004, German programmer Tobias Lütke was living in Ottawa with his girlfriend.

An avid snowboarder, he wanted to launch an online snowboard shop, but found the e-commerce software available at the time to be clunky and expensive.

So he decided to write his own e-commerce software.

After he launched his online snowboard business, called Snowdevil, other online merchants were so impressed with what he built that they started asking to license Tobi's software to run their own stores.

Tobi and his co-founder realized that software had more potential than snowboards, so they launched the e-commerce platform Shopify in 2006.

Since then, it has grown into a publicly-traded company with over 7,000 employees and $11 billion in revenue.

Timestamps:

• 04:55 - Tobi discovers snowboarding–and meets his future wife–on vacation in Canada
• 09:00 - Building a new kind of snowboarding company
• 24:55 - Pivot point: skateboards or software?
• 29:45 - The night before Tobi’s wedding, Shopify switches business models
• 39:15 - The 2008 financial crisis hits… revealing a huge opportunity
• 52:45 - After a decade, Shopify goes public

This episode was produced by Casey Herman with music composed by Ramtin Arablouei. It was edited by Neva Grant. This archive episode was produced by Katherine Sypher.

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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:

• 09:51 Brian's eureka moment that led to the birth of UGG
• 12:41 The first sales trip results in ZERO sales
• 21:10 The mantra that kept Brian going while doing odd summer jobs to survive
• 28:32 Brian gets a critical lesson in marketing…from some 12-year-old kids
• 51:59 Brian’s most effective strategy for retail: the “Six-Pair Stocking Plan”
• 56:42 On track to regain his ownership - Brian hits a huge snag
• 01:01:57 A midnight phone call from Australia saves the business
• 01:11:28 Brian gets the last laugh in the trademark dispute - and acquires a boot factory
• 01:14:54 Pamela Anderson wears UGGs on the set of Baywatch
• 01:23:39 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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At 25, Justin Gold was making experimental peanut butter in his home kitchen with a food processor and a stack of recipe journals. His singular obsession: bring new life to a tired lunchtime staple.

What started as late-night experiments with honey, cinnamon and banana eventually became Justin's — one of the most influential natural food brands of the last two decades.

At first, Justin got rejected by most grocery stores he approached. He worked overnight in a shared industrial kitchen, hand-filling jars one at a time. He couldn’t get a distributor, so he stocked the shelves at the Boulder Whole Foods himself.

And when growth stalled… he had an idea during a mountain bike ride that would transform the company: What if peanut butter came in a squeeze pack?

In this episode, Justin explains how relentless experimentation and stubbornness helped him build a category-defining brand — and how, with each entrepreneurial milestone, an even more challenging one emerged.

YOU’LL LEARN:

• How Justin reverse-engineered flavored peanut butter in his apartment
• How launching in Boulder gave him a big advantage
• How he learned when to listen to feedback, and when to ignore it
• The deal he made with Whole Foods: “I’ll stock the shelves myself.”
• How the squeeze pack transformed the business, and why it almost didn’t work
• The power of naïve persistence in entrepreneurship

Timestamps:

• 00:09:35 — The obsessive recipe experiments that became Justin’s edge
• 00:16:25 — Getting support from Boulder’s startup food community
• 00:21:28 — Raising $35,000– and shocking his family: “I wanna make peanut butter!”
• 00:42:51 — The farmers market feedback that changed the product line
• 00:46:56 — Justin talks his way into the first Whole Foods
• 00:51:47 — Justin’s gets into more stores, but sales start to stagnate
• 00:53:35 — The mountain bike ride that sparked the squeeze-pack idea
• 01:19:43 — The brand gets sold, Justin gets fired…and invited back

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

Edited by Neva Grant, with research help from Alex Cheng.

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Today’s callers: David from New Jersey struggles with self-doubt as he works to grow his muscle-scraping soap brand. Then, Marnie from Australia wants to convince customers that her colorful tick-repellent socks are worth the premium price. And David from New York wants his company to end the practice of throwing away burned out candles.

Plus, Sarah recounts rebuilding her brand in the wake of the pandemic and the changing fashion preferences of professional women.

Thank you to the founders of Sorsoap, Tick Socks, and Siblings 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 M.M. LaFleur’s founding story as told by Sarah 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 Jimmy Keeley.

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

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NVIDIA is one of the most valuable companies in human history. Its chips run the AI systems transforming everything from entertainment to warfare. But for years, almost nobody believed in co-founder Jensen Huang’s vision. Jensen spent nearly a decade pouring billions into a technology called CUDA, long before AI made it profitable.

In this deeply personal conversation, Jensen tells Guy why NVIDIA’s very first chip was a catastrophic failure … and how at one point, the company was 30 days away from going out of business.

Jensen also explains why he thinks fears about AI are overblown, and why he believes the next generation will have more opportunity — not less — because of AI.

What You’ll Learn:

• Why NVIDIA nearly collapsed before becoming an AI giant
• How researchers sparked the AI boom using NVIDIA gaming chips
• How to lead through uncertainty when a huge bet hasn’t yet paid off
• How Jensen approaches hard decisions like an engineer
• We’re “doing ourselves a disservice” by being afraid: Jensen on AI and job loss
• How Jensen defends his demanding management style
• Why past failures still haunt him

Key Moments From the Interview:

• 00:07:51 — Jensen Huang’s childhood at an unusual Kentucky boarding school
• 00:14:50 — Why Jensen left a stable career to help start NVIDIA
• 00:17:14 — NVIDIA’s first failure: the NV1 disaster
• 00:19:51 — The desperate trip to Japan that gave the company a lifeline
• 00:23:11 — “The only idea we had” for prototyping: the emulator Hail Mary
• 00:30:53 — The book that shaped Jensen’s thinking about innovation
• 00:35:04 — Why NVIDIA kept investing in CUDA while Wall Street lost faith
• 00:41:38 — The moment AI researchers discovered the power of NVIDIA’s chips
• 00:53:17 — Jensen on fear of job loss from AI, and why America risks falling behind
• 01:01:56 — Knowing what he knows now, would he do it again? Yes — and no

This episode was researched and produced by Alex Cheng with music by Ramtin Arablouei. It was edited by Neva Grant. Our engineers were Patrick Murray and Robert Rodriguez.

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Today’s callers: Kristina in Florida wants to take her local pottery workshops nationwide. Then Jim from Colorado wonders if retail is right for his quick release camera straps. And Will in Ohio hopes his business will change what consumers expect from tool rental services.

Thank you to the founders of Seagrass Pottery, Lemur Strap and Tool Club 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 our episodes with Chieh Huang of Boxed, Hernan Lopez of Wondery and David Neeleman of Jet Blue.

This episode was produced by Kerry Thompson with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Cena Loffredo.

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

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