Stephen Starr didn’t plan to get into the restaurant business.

He set out to be a radio DJ. Then a nightclub owner. Then a music promoter.

Along the way, he booked a young Jerry Seinfeld for $75, promoted shows for U2 and Madonna, and spent years pretending to be more successful than he really was.

Then, in his late 30s, Stephen walked into a glitzy martini bar in New York.

He was so taken with it, he decided to start his own version in Philadelphia.

Today, Starr Restaurant Group generates nearly half a billion dollars in annual revenue and includes some of the most successful independent restaurants in America: Pastis, Buddakan, Le Diplomate, Parc, Makoto, and dozens more.

The surprising part?

Stephen did not start out as a foodie.

Instead, he became obsessed with the theatre of dining: design, upholstery, lighting, music. A “wow!” feeling when you walk in the door.

In this conversation with Guy, Stephen talks about the hard lessons he learned in the comedy and music business, and the unexpected path he took to redefining dining.

What You'll Learn:

• The unglamorous economics of rock concerts and restaurants
• How rejection, romantic heartbreak, and failure can become powerful motivators
• Why he believes he's spent his career "throwing the party" without attending it
• How building the right team of designers can make a restaurant feel magical
• Why Stephen says today's entrepreneurs have a much harder path than his generation did
• The model Stephen says new restaurateurs should follow today

Timestamps:

• 00:03:38 — A lonely childhood: Making up skits in his room
• 00:07:24 — Losing his mother at age 19
• 00:08:52 — Starting a comedy club: Deli by day. Stand up at night
• 00:18:24 — Going broke and reneging on a bank loan
• 00:26:01 — Music promotion: Feeling like a fraud while promoting U2, Madonna
• 00:34:27 — A New York martini bar inspires Stephen to start his own
• 00:37:40 — The bold design behind a line-out-the-door restaurant
• 00:57:21 — Opening Buddakan in New York: “I can’t do anything better. This is Sgt. Pepper”
• 01:02:58 — Starting a restaurant today: “I would say don’t do it … but if you do, keep it smaller”

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

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Today’s callers: Daisy in the United Kingdom looks to grow her barefoot shoe brand across the pond in the United States. Then Rachel in Pennsylvania considers private labeling for her protein-packed sprinkles. And Andrew in California wonders whether he should seek investment for his pleasantly-scented soil additive.

Plus, Shazi discusses why entrepreneurship is one of the most creative outlets a person can have.

Thank you to the founders of Freet Barefoot, SprinkleBites, and PlantAmika 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 Happy Family Organics’ founding story as told by Shazi in 2020.

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

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

When Maxine Clark left a top job in retail to start a make-your-own stuffed animal store, people thought she’d lost her mind.

Investors doubted it. Friends questioned it. Retail experts couldn't understand how it would scale.

But drawing on more than 20 years as a retail executive, Maxine built a massively successful shopping “experience,” where kids could stuff, dress and personalize their own stuffed animals.

Today, Build-A-Bear has generated billions in sales, survived the decline of malls, weathered the financial crisis, and become a global brand.

WHAT YOU'LL LEARN

How a failed errand—and an offhand comment by a kid–inspired a business plan

How Maxine leveraged two decades of retail experience to launch Build-a-Bear

How Willy Wonka and Walt Disney were early inspirations

How she built a wedge against competitors

How she got through the financial crisis

How she knew when to step down as CEO– and how to collaborate with her successor

TIMESTAMPS:

• 05:52 - A mom Who Worked for Eleanor Roosevelt
• 09:18 - The Impromptu Interview That Changed Maxine’s Career
• 16:00 - Becoming One of the Few Female Fortune 500 Executives
• 18:43 - Why She Walked Away From Payless
• 21:27 - The Beanie Baby Disappointment That Sparked Build-A-Bear
• 26:14 - Designing the First Store: “Make it Like Willy Wonka.”
• 37:53 - Opening Day — and a Line Out the Door
• 39:53 - Defending the Brand Against Copycats and Lawsuits
• 45:53 - Scaling to Hundreds of Stores and Going Public
• 58:25 - Letting Go: Stepping Down as CEO and Building a Legacy

This episode was researched by Rommel Wood and produced by Kerry Thompson, with music by Ramtin Arablouei, and edited by Neva Grant.

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Today’s callers: Whitney in Utah wonders how to bridge the gap between pre-seed and institutional investment for her fitness/retail combo space. Then Chloe in the U.K. considers which markets to target for her at-home crafting kits. And Christy in Washington wants to convert gifters into repeat customers for her coffee flavoring brand.

Plus, Christina’s take on why Milk Bar is better served with her as Chief Experimenter rather than Chief Executive.

Thank you to the founders of The Beau Collective, Cotton Clara, and Vashon Island Coffee Dust.

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 the story of how Christina founded Milk Bar from our episode back in 2019.

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

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

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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:

• 07:20 - Tobi discovers snowboarding–and meets his future wife–on vacation in Canada
• 11:25 - Building a new kind of snowboarding company
• 29:35 - Pivot point: skateboards or software?
• 34:25 - The night before Tobi’s wedding, Shopify switches business models
• 45:25 - The 2008 financial crisis hits… revealing a huge opportunity
• 58:55 - 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.

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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.

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