Best Casper Oliver Podcasts (2025)

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Williams Sonoma vs. Quince and the Future of the Dupe Economy 12:16

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4d ago12:16

12:16

A blockbuster lawsuit just exposed the biggest fear in retail—but it could backfire spectacularly. Today, Sammi does a deep dive into Williams Sonoma vs. Quince, a case that’s revealing a seismic consumer shift: shoppers no longer believe legacy brands deserve legacy prices. Sammi breaks down why Quince’s billion-dollar rise is shaking old-guard re…

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Luana Lopes Lara (Kalshi) on the Money in Prediction Markets, Trading the Presidential Election and Suing the Regulators 51:46

7d ago51:46

51:46

Luana Lopes Lara didn’t just build a unicorn— she overturned a 100-year old ban, sued the regulators and became the youngest self-made female billionaire in the process. Luana co-founded Kalshi, the CFTC-regulated prediction market that lets you trade on the outcome of real-world events. Kalshi is one of the fastest-growing tech companies in the co…

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Raw Chicken Nuggets and $75 Matcha: Meadow Lane’s Chaotic Rise to Fame and Infamy 12:54

11d ago12:54

12:54

Today, Sammi breaks down all things Meadow Lane—the Tribeca grocery store that launched like a luxury fashion drop and spiraled into one of the most chaotic openings New York has seen in years. Founded by Sammy Nussdorf, the heir to a billion-dollar distribution empire, Meadow Lane was positioned as a bespoke, Manhattan-made answer to Erewhon. The …

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Babba Rivera (Ceremonia) on Making Business Personal, Winning Retail, and Convincing Investors to Bet on Latinx Communities 59:49

14d ago59:49

59:49

Building a beauty brand that celebrates Latin culture while competing on a global stage is no small feat—but for Babba Rivera, it’s not just business— it’s personal. Babba founded Ceremonia to create a haircare brand rooted in Latin heritage, ritual, and community. Today, Ceremonia is one of the fastest-growing brands at Sephora, has raised over $1…

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Inside Rhode’s $1 Billion Deal: How e.l.f. Exposed Every Secret Behind Hailey Bieber’s Brand 13:23

18d ago13:23

13:23

Celebrity brands never release their numbers — until now. Beauty brand e.l.f. didn’t just acquire Hailey Bieber’s Rhode… they published every single line item of the company’s P&L. From shockingly low cost of goods sold to a 9x marketing efficiency ratio, Sammi unpacks why Rhode operates more like a billion-dollar conglomerate than a three-year-old…

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Julia Cheek (Everlywell) on Revolutionizing Diagnostics, Shark Tank and Biohacking 1:06:56

21d ago1:06:56

1:06:56

Many people say the healthcare system is broken. Julia Cheek, is trying to fix a key part of that system: diagnostics. Julia is the founder and CEO of Everlywell, the pioneering at-home health testing company that turned diagnostics from something that happened to you into something you control. Since launching in 2015, Everlywell has become one of…

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The Row’s Quiet Luxury Gets Loud: Sample Sales, Influencer Drama, and the Future of Fashion’s Most Mysterious Brand 14:20

25d ago14:20

14:20

Today Sammi unpacks the silent spectacle of The Row—Mary-Kate and Ashley Olsen’s luxury label. Known for its “no logos, no advertising” ethos and a fiercely minimalist aesthetic, The Row has built its brand on mystique. But when a chaotic, viral sample sale hit New York this past October—drawing TikTok influencers and 9 hour+ lines—the brand’s care…

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Jaclyn Johnson and Marina Middleton (Create & Cultivate) on How To Sell Out a Live Event, the Future of Community, and Whether Virtual Events Are Dead 45:38

28d ago45:38

45:38

Today, Sammi sits down with Jaclyn Johnson and Marina Middleton—the powerhouse duo behind Create & Cultivate. Long before every brand wanted a “community,” Jaclyn and Marina built one that actually mattered: a movement where founders, Fortune 500 leaders, and creators came together to build what’s next. After selling the company in 2021, Jaclyn stu…

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The “PayPal Mafia” Lore: Inside the Elon Musk Coup and the Beginning of Founder Culture 13:15

1M ago13:15

13:15

Today, Sammi uncovers one of the most iconic origin stories in tech: how a scrappy, chaotic startup from the late ’90s — PayPal — became the launchpad for a generation of founders who went on to build Tesla, LinkedIn, Yelp, Affirm, Palantir, SpaceX, and more. Before they were billionaires or household names, Elon Musk, Peter Thiel, Reid Hoffman, Ma…

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How AI helps the McLaren F1 Team make every second count 38:00

1M ago38:00

38:00

The world record for fastest pit stop—a mere 1.8 seconds—was set by the McLaren F1 Team at the Qatar Grand Prix in 2023. It’s an incredible feat of speed and choreography; a pit stop that fast can’t happen without a team of people operating at peak human performance. But as Dan Keyworth explains, AI plays a crucial role, too. As the Director of Bus…

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Marina and Ricardo Larroudé (Larroudé) on Innovative D2C Models, Betting on Brazil and Trading in the 9-to-5 57:39

1M ago57:39

57:39

When the world shut down, Marina and Ricardo Larroudé hit go. Out of their Manhattan apartment, the former Teen Vogue fashion director and her financier husband built Larroudé—a shoe brand that went from zero to millions in sales in just a few years. In this episode, Sammi dives into how they turned job loss into rocket fuel, built their own factor…

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The 90s Microdrama Revolution and Ghost of Quibi 22:46

1M ago22:46

22:46

Hollywood is changing—and its future might be vertical. Today, Sammi dives into the explosive rise of “microdramas,” the ultra-short, ultra-addictive scripted shows that are pulling in billions and leaving traditional studios scrambling to survive. From Chinese-backed apps like ReelShort to Hollywood execs betting on AI-powered storytelling, this i…

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Gwen Whiting (The Laundress) on Acquisition Cautionary Tales, Bootstrapping, and The Fill 1:01:18

1M ago1:01:18

1:01:18

Gwen Whiting co-founded The Laundress, the luxury laundry brand that transformed washing clothes into a lifestyle statement. What started as a passion project funded by credit cards became a cult favorite—and eventually caught the attention of Unilever, which acquired the company for a reported $100 million. But the dream deal didn’t go as planned.…

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Spirit Halloween: The Billion-Dollar Pop-Up That Can’t Be Beat 15:32

2M ago15:32

15:32

Today’s episode is all about the billion dollar business built on a business model that defies every rule of traditional retail; they occupy buildings for just three months a year, hire around 50,000 seasonal workers, carry zero inventory for nine months, and somehow they're not just surviving— they are thriving. The business? Spirit Halloween, of …

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This poet discovered AI and fell back in love with his creative career 41:24

2M ago41:24

41:24

Iain Thomas is a poet, author, and the Chief Innovation Officer at Sounds Fun—an advertising and creative agency that he co-founded with the belief that human creativity could be enhanced, rather than diminished, with the help of AI. It’s a realization that actually began to dawn on Iain a few years prior, after his mother died. He wasn’t sure how …

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RH’s Luxury Mountain and House of Cards: Part 2 23:59

2M ago23:59

23:59

In part two of her Restoration Hardware deep dive, Sammi pulls back the curtain on what’s really at the top of “Luxury Mountain.” From the troubled Aspen expansion and RH’s sky-high ambitions in Europe, to eyebrow-raising governance decisions, failed ventures, and Warren Buffett’s very public goodbye— you have to wonder: is the RH foundation starti…

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Yachts, Private Jets and The Restoration Hardware CEO Lore: Part 1 30:10

2M ago30:10

30:10

Today, Sammi delivers the most requested episode topic yet: the lore of Restoration Hardware and its CEO, Gary Friedman. Gary Friedman is part visionary, part provocateur and part illusionist. He is the CEO who took a nearly bankrupt furniture company and convinced Wall Street that it was building the LVMH of America. And for a while everyone belie…

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Jim McKelvey (Square) on How to Out-Compete a Goliath, Advice for “Wantrepreneurs,” and Economizing Drug Trials 1:05:29

2M ago1:05:29

1:05:29

Building something that lasts is rare. Building something that rewires an entire industry? That’s almost unheard of. But that’s exactly what Jim McKelvey did when he co-founded Square (now Block) with Twitter co-founder Jack Dorsey. Today, Jim and Sammi talk about how Square went head-to-head with Amazon and won, why Jim believes most startups don’…

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The Future of Shopping Is Here— And It’s AI 11:47

2M ago11:47

11:47

What if you never had to click “Buy Now” again—because your AI did the shopping for you? Today, Sammi breaks down the partnership between OpenAI and Stripe that could rewrite the rules of e-commerce. With the launch of the Agentic Commerce Protocol, AI can now recommend, purchase, and process transactions entirely within ChatGPT—no links, no websit…

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The distillery with an AI-backed plan to lift their spirits 33:29

2M ago33:29

33:29

Bespoken Spirits isn’t your typical whiskey distillery. Yes, they’re based in the American bourbon heartland of Lexington, Kentucky, and yes, they often make private label whiskeys for clients. But everything from how Bespoken Spirits distills their whiskey to how they market it is done with the help of AI. Jordan Spitzer, their head of flavor, can…

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Tracy Anderson (Tracy Anderson Method) on Building a Fitness Empire, Debunking Wellness Trends, and IP in Fitness Routines 1:08:51

2M ago1:08:51

1:08:51

From small studios to celebrity status, Tracy Anderson has built one of the most influential—and imitated—fitness empires in the world. Today, Sammi sits down with the fitness icon whose method has shaped some of the most famous bodies in Hollywood to peel back the layers of the brand, the science, and the woman behind it. Tracy opens up about the …

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Why I Shut Down My Matcha Business 15:54

2M ago15:54

15:54

Have you ever built a business around something you love—only to realize it’s draining your passion? In this episode, Sammi shares her full founder story: launching a matcha brand during business school, fighting to scale it, surviving the 2020 lockdown, and finally deciding to shut it down. She breaks down the unglamorous side of entrepreneurship,…

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Neil Parikh (Casper, Slingshot AI) on Using AI for Emotional Wellbeing, Lessons from Cofounding Casper and Finding Winning Angel Investments 56:47

2M ago56:47

56:47

By Social Currency

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Jeep’s Flop Era? 14:50

2M ago14:50

14:50

Today, Sammi unpacks the dramatic meltdown of the Jeep brand. Once a cultural symbol that survived world wars and recessions, Jeep’s market share has now plunged to historic lows. Behind the scenes: a billionaire family dynasty, leadership obsessed with margins over customers, and a string of decisions so poor they’ll likely become a business schoo…

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These people made an internal podcast. AI helped them reach the whole team 38:08

3M ago38:08

38:08

Amanda Cupido doesn’t speak Spanish or French. But using AI, she and her team helped a global nonprofit make their internal podcast more accessible to as many employees as possible. Amanda is an audio producer and the founder of a production company called Lead Podcasting. One of her clients is a global nonprofit with over 35,000 employees—and not …

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Julia Hartz (Eventbrite) on Taking a Company Public, Leading Through Crisis and the Future of Live Events 1:08:58

3M ago1:08:58

1:08:58

Julia Hartz co-founded Eventbrite in 2006 with a bold vision: make ticketing accessible for anyone creating an event. Nearly two decades later, she’s still at the helm as CEO, having taken the company public in 2018 and steered it through one of the toughest crises imaginable—the pandemic, when live events disappeared overnight. In this episode, Ju…

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Inside the Protein Boom: The $1.2 Billion Bet Reshaping What We Eat 12:22

3M ago12:22

12:22

Why is everything from your Starbucks drink to your popcorn now enhanced with extra protein? With 61% of Americans increasing their protein intake last year, cottage cheese sales skyrocketing 20%, and Starbucks rolling out drinks with 36 grams of protein, it’s clear this isn’t a fad—it’s a seismic shift in how we eat. Sammi explores the cultural, m…

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Maria Davidson (Kojo) on Record-Breaking Fundraising, Building a $4B Platform and Breaking Barriers in Construction 1:04:20

3M ago1:04:20

1:04:20

Maria Davidson is making construction procurement cool— and a billion-dollar business. After studying philosophy, politics, and economics at Oxford and a stint in venture capital, Maria set her sights on one of the least “sexy” industries imaginable: construction. What started with her hustling for meetings by showing up at job sites with pizza has…

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Are Membership Clubs Dead? 11:09

3M ago11:09

11:09

From London’s 17th-century gentleman’s clubs to the meteoric rise of Soho House, private membership clubs have always been about more than cocktails and couches—they’re cultural status symbols. But as Soho House goes private again in a $2.7 billion deal, the playbook for exclusivity is being rewritten. Today, Sammi unpacks the cracks in the traditi…

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For these shipwreck-hunting humans, AI is part of the crew 30:39

3M ago30:39

30:39

Very few people get paid to visit shipwrecks—but for Stephanie Gandulla, it’s all part of the job. Stephanie is a scuba diver, maritime archeologist, and resource protection coordinator for the Thunder Bay National Marine Sanctuary. The agency safeguards Lake Huron’s historic shipwrecks, many of which have yet to be discovered. That’s where Katie S…

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Vanessa Dew (Health-Ade Kombucha): From Farmers' Markets to a $500M Empire, Life After an Exit and Fundraising 101 52:13

3M ago52:13

52:13

From hand-bottling kombucha in an apartment kitchen to building a $500 million brand sold in tens of thousands of stores across the country, Vanessa Dew didn’t just build a company— she built a movement. As the co-founder of Health-Ade Kombucha, Vanessa turned a niche wellness drink into a household name, all while keeping true to the company’s art…

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3 Lessons from Amazon That Changed My Business 12:15

3M ago12:15

12:15

Today, Sammi’s doing something a little different. She’s pulling back the curtain on her five years at Amazon—and the lessons she’s bringing with her as she builds Social Currency. Sammi breaks down the three Amazon frameworks that really work: customer obsession (yes, the empty chair in meetings is real), the fiery but brilliant “disagree and comm…

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Alli Webb (Drybar) on Selling for $255M, Second Acts, and Embracing the Messy Truth 1:03:34

3M ago1:03:34

1:03:34

What do you do after creating a $255 million brand that reshaped an entire industry? If you’re Alli Webb, founder of Drybar, you sell it, rebuild, and then launch something even more personal. Sammi and Alli go deep into the scrappy early days of Drybar, the chaos of scaling to hundreds of locations, and the bittersweet reality of selling your life…

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The Denim War: How American Eagle, Gap, and Lucky Brand Turned Jeans into Culture and Controversy 11:22

3M ago11:22

11:22

This summer, denim wasn't just a fashion statement—it was a battlefield. Today, Sammi unpacks how American Eagle, Gap, and Lucky Brand launched three wildly different campaigns that turned jeans into a referendum on identity, controversy, and cultural capital. From American Eagle’s headline-grabbing Sydney Sweeney campaign to Gap’s inclusive girl-b…

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Why the hot new ingredient in this chef’s pantry is AI 33:02

3M ago33:02

33:02

Ian Ramirez has spent his career finding innovative ways to make mouth-watering meals for clients—and one of his latest ingredients is artificial intelligence. As a chef, culinary consultant, and co-founder of Mad Honey Culinary Studio and Goods, he’s the guy that brands hire to get their product on restaurant menus, and make it look and taste good…

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Bill Ready (Pinterest) on Social Media’s “Big Tobacco” Moment, Growing Pinterest to 578M Users, and What Gen Z Really Wants 1:04:52

3M ago1:04:52

1:04:52

Bill Ready has never been afraid to make big bets—and at Pinterest, those bets are paying off. Since becoming CEO, he’s doubled down on building a healthier internet: one where all accounts under 16 are private by default, AI is tuned for positivity, and users come away inspired instead of exhausted. Today, Sammi sits down with Bill to trace his jo…

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The Goop Paradox: $140M and 17 Years Later, Why Isn't It Profitable? 12:50

4M ago12:50

12:50

Seventeen years. $140 million in funding. And Goop—the empire Gwyneth Paltrow built on clean beauty, provocative candles, and aspirational wellness—is still not profitable. Today, Sammi unpacks the paradox of Goop: a brand that pioneered the $6.3 trillion wellness industry, yet can’t seem to make money from it. From the downfall of Goop Beauty at S…

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Coming soon: Season two 1:54

4M ago1:54

1:54

Working Smarter is back for season two! Starting September 3, we’re going beyond the hype and headlines to bring you stories about real people using AI to do more of what they love about their jobs. From the F1 track to the kitchen—and even the bottom of a lake—learn how new tools are helping creatives, makers, visionaries, and their teams think bi…

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Amy Liu (Tower 28) on Life-Changing Pitches, Picking the Right Partners and Standing Out in a Crowded Industry 51:21

4M ago51:21

51:21

Some say cult-favorite beauty brand Tower 28 is an “overnight success”— but founder Amy Liu is here to share how the brand’s success was years in the making. Today, Sammi and Amy dive into the real story behind Tower 28’s rise: from Amy’s scrappy Sephora pitch and pandemic launch to lessons from her friends and family fundraising round. Amy also gi…

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How the Fitness Industry Is Coming for Religion 7:29

4M ago7:29

7:29

Fitness is the new religion. It sounds dramatic, but look around. People used to go to church on Sundays. Now they go to Barry's Bootcamp. Instead of confession, they cold plunge. Today, Sammi unpacks how the boutique fitness boom became a new form of secular spirituality—complete with instructors as gurus, before-and-after photos as testimonies, a…

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Emily Heyward (Red Antler) on Building Brands That Stick, How AI Will Impact Creative Agencies and Lessons from Casper’s Success 48:34

4M ago48:34

48:34

What do Casper and Allbirds have in common, besides redefining modern D2C brands? They all worked with branding agency Red Antler before they became household names. Today Sammi sits down with Emily Heyward, co-founder of Red Antler, the powerhouse creative agency behind some of the most iconic startups of the last decade. Emily shares how Red Antl…

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Inside Rippling vs. Deel’s Billion-Dollar Espionage War 14:29

4M ago14:29

14:29

What happens when a unicorn startup hires a spy to infiltrate its biggest rival? Welcome to the $28 billion battle between Rippling and Deel—where encrypted messages, crypto payments, burner phones, and a secret escape to Dubai are all part of the plot. Today, Sammi unpacks the real-life espionage scandal playing out in Silicon Valley. At the cente…

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James Reinhart (ThredUp) on Educating Your Customer, Designing a Stellar Customer Experience, and the Future of Fashion Resale 59:43

4M ago59:43

59:43

James Reinhart didn’t set out to change the way we shop—he just wanted to clean out his closet. But that simple idea turned into ThredUp, the giant and beloved resale marketplace. In today’s episode, Sammi sits down with James to unpack how he went from teaching in classrooms to disrupting closets. They talk about the bold bet that helped ThredUp o…

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$33 Toilet Paper and $48 Olive Oil? Welcome to the Age of Every-Day Luxury 10:07

4M ago10:07

10:07

Would you spend $33 on toilet paper just because it looks good on your bathroom shelf? You’re not alone—and there’s a reason why. Today Sammi unpacks the rise of what she calls aesthetic utility—a consumer movement where everyday essentials are elevated into lifestyle flexes. Gone are the days of basic olive oil and generic hand soap; now, products…

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Ariel Kaye (Parachute) on Getting D2C Right, Building Customer Trust and Selling Out of Product Without Becoming a Sellout 45:56

4M ago45:56

45:56

Today, Sammi is joined by Ariel Kaye, the founder of Parachute—the cult-favorite home essentials brand that helped define the direct-to-consumer movement. Ariel shares the real story behind Parachute’s early days: from bootstrapping her first launch to navigating funding rounds, managing growing pains, and expanding from digital to retail. She open…

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The Rise and Fall of Juicero: Silicon Valley's $120 Million Juicing Catastrophe 12:47

5M ago12:47

12:47

Today, Sammi dives into the dramatic rise and fall of Juicero, a startup that raised $120 million to solve a problem that didn't exist with an over-engineered solution. Founded by Doug Evans, who aspired to revolutionize the juice industry, Juicero promised a convenient, high-tech juicing machine. Despite backing from major investors like Google Ve…

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Tyler Denk (Beehiiv) on How to Grow a Profitable Newsletter, Lessons from Morning Brew and AI Bots For Creators 1:15:23

5M ago1:15:23

1:15:23

What’s the secret behind today’s fastest-growing newsletters—and how can creators build smarter, not harder? Tyler Denk is here to answer exactly that. Tyler was one of the first hires at Morning Brew, and now is CEO of Beehiiv, the platform that’s powering some of your favorite newsletters and fueling a new wave of digital media empires. Tyler sha…

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Why Some Celebrity Brands Flop While Others Break the Internet 14:08

5M ago14:08

14:08

From skincare to alcohol, it feels like every celebrity has a brand and your feed is probably full of them. But why do some explode while others quietly crash and burn? Today, Sammi breaks down what really separates the hits from the hype. Is it all about star power—or does authenticity actually matter? Sammi dives into the blueprint behind success…

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Phoebe Gates & Sophia Kianni (Phia) on Disrupting Fashion, Rethinking Retail, and Building a Business That’s Good for the Planet 54:59

5M ago54:59

54:59

The fashion industry is facing a reckoning—from how clothes are made to how they’re resold. And Phia, a new tech-driven platform, is betting that the future of shopping is secondhand, smarter, and more sustainable. In this episode, Sammi sits down with Phia co-founders Phoebe Gates and Sophia Kianni to talk about how they went from brainstorming id…

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Buy Now, Pay Later: The Good, The Bad and The Ugly 20:01

5M ago20:01

20:01

Buy now, pay later is everywhere. Maybe you've seen it when you were buying a Sephora haul, or deciding that you deserve to splurge on your DoorDash delivery, but what’s the truth behind the trend? Today, Sammi answers the question: is BNPL just a shiny new version of the old school layaway, gamified for the TikTok generation? Or is it more danger…