What does building a billion-dollar company actually feel like? According to Ring founder Jamie Siminoff, it's far less glamorous than most founder stories make it seem.

Jamie joins Sammi to unpack the journey from almost running out of money to building Ring into one of the biggest consumer tech acquisitions in history. He explains why entrepreneurship can be deeply traumatic, how close Ring came to bankruptcy before appearing on Shark Tank, and why the rejection that made headlines wasn't nearly as important as what happened afterward.

They also discuss why Jamie spent nearly all of Ring's remaining cash buying Ring.com, the lawsuit that nearly destroyed Amazon's acquisition, why he eventually walked away from running Ring despite loving the company, and what brought him back years later.

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00:00 Jamie Siminoff’s Social Currency

02:03 Partner Message: Mercury for Business Banking

03:22 Why Entrepreneurship Is More Traumatic Than People Admit

05:20 Why Jamie Came Back to Ring

07:30 Life After Selling Ring to Amazon

08:50 Knowing When It's Time to Walk Away

09:30 Why Retirement Didn't Last

11:10 The Story Jamie Almost Didn't Tell

13:15 Why You Shouldn't Start a Company for Money

14:30 The Mission Behind Ring

16:00 Can You Actually Measure Safer Neighborhoods?

18:00 Partner Message: Rula

19:14 Partner Message: Mercury for Personal Banking

20:28 The Customer Stories That Make It All Worth It

22:00 How Ring Became a Household Name

24:15 How Close Ring Came to Bankruptcy

26:05 The Shark Tank Effect

27:13 Why Rejection Wasn't Ring's Biggest Break

29:07 The Survivorship Bias of Entrepreneurship

30:19 Why AI Will Reward Builders

31:46 The $1 Million Bet on Ring.com

35:30 Why "DoorBot" Had to Die

36:44 Rebuilding Ring From Scratch

37:07 Partner Message: Bilt

38:08 The Lawsuit That Almost Killed the Amazon Deal

40:40 From the Highest High to the Lowest Low

42:30 The Settlement That Saved Ring

43:24 Building a Hypergrowth Company While Running Out of Money

44:27 Calling Amazon Back

46:53 Being a Solo Founder

50:39 Superbowl Ad

01:00:00 Social Currency Corner

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Peter Semple is CEO of Depop,  the fashion resale marketplace that became one of Gen Z's most influential shopping platforms and completely changed how a new generation thinks about secondhand fashion. 

Peter joins Sammi to break down how Depop built a community-first brand, why the company made the surprising decision to eliminate seller fees, and what it takes to scale beyond Gen Z without losing cultural relevance. They also discuss why Peter wants Depop to become the "Nike of resale," the future of AI-powered shopping, and what the recently announced $1.2 billion acquisition by eBay means for the next chapter of the business.

Plus: why Depop keeps showing up cultural moments (from rap lyrics to SNL), and what happens when superfans become employees.

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Here’s What Sammi Covers with Peter:

00:00 Peter Semple’s Social Currency

02:14 Partner Message: Mercury for Personal03:36 From Copywriter to CEO05:49 What Google Creative Lab Taught Him About Brands08:04 Leaving Google for a Startup10:13 How Sneakers Led Him to Depop11:58 Why Depop Hires Its Own Users

14:34 Partner Message: Rula

15:49 Partner Message: Mercury for Business17:08 The Mindset Shift From CMO to CEO20:07 How Depop Scales Without Losing Gen Z24:25 Building the “Nike of Resale”26:01 Why Depop Eliminated Seller Fees29:13 The Power of Circular Fashion

30:06 Partner Message: Bilt

31:07 Partner Message: Shopify32:22 Why Brands Should Earn, Not Chase, Cultural Relevance35:10 From SNL to Rap Lyrics: Becoming Part of Culture38:06 What the $1.2 Billion eBay Acquisition Means42:13 Can Sustainability Beat Fast Fashion?45:20 Why Shopping Should Feel Like a Treasure Hunt46:56 How AI Is Changing Fashion Resale50:03 Will AI Change How We Discover Products?52:38 Depop’s Competitive Advantage55:00 The Secret Behind the Name “Depop”

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Twenty years after uploading his first YouTube video, Gary Vaynerchuk is still obsessed with where attention is going next. Today, he joins Sammi to talk about his predictions and why it’s not too late to get started on social media.

Gary explains why he believes social media has become “interest media,” how AI and authenticity are not mutually exclusive, and why quantity remains one of the biggest competitive advantages in content.

They also discuss the rise of live shopping, why Gary is betting big on IRL experiences, and the long-term vision behind VeeFriends—his modern intellectual property empire centered around optimism, accountability, and character development. Along the way, Gary shares his approach to mental health, whether he wants his kids to take over his business, and the one thing he still hasn’t done yet. Plus, they revisit one of Sammi’s favorite pieces of Gary’s content… and it’s a real tearjerker.

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Here’s What Sammi Covers with Gary:

00:00 Gary Vaynerchuk’s Social Currency

02:14 Partner Message: Mercury for Business

03:37 Uploading His First YouTube Video 20 Years Ago

05:34 Why Gary Only Talks About What He Knows

07:22 Why Social Media Became “Interest Media”

09:35 The Platform Predictions That Made Gary Famous

12:13 Why Content Merit Matters More Than Followers

14:20 Partner Message: Rula

15:36 Partner Message: Bilt

16:36 AI, Authenticity, and the Creator Dilemma

17:57 Why Quantity Is a Competitive Advantage

19:00 The Power of “And” Instead of “Or”

20:25 Why Gary Is Betting Big on IRL Experiences

21:14 The Rise of Analog in a Digital World

22:24 What Gary Will Never Outsource to AI

24:20 Why Great Businesses Ignore Personal Preference

25:12 Will Humans Eventually Marry AI?

26:23 The Upside of AI That People Ignore

27:33 The Video That Best Captures Gary’s Philosophy

28:53 Why Gary Cares So Much About Underdogs

30:10 The Difference Between Positivity and Delusion32:20 Gary’s Approach to Mental Health

33:23 Partner Message: Mercury for Personal

34:37 Partner Message: Shopify

35:57 What Gary Wants for His Kids

37:50 Why VeeFriends Is His Most Important Project

39:34 Building an IP Empire Through Character-Based Storytelling

42:13 Why Live Shopping Is Finally Taking Off

44:10 Gary’s Advice for Sammi’s New Live Show

46:06 Why Creators Need More Content on More Platforms

46:29 Gary’s First Viral Video

47:33 Who Gets the Good News—and Who Gets the Bad News

48:08 Whether Gary Will Ever Take a Real Break

49:28 The 15/85 System That Runs His Career

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Matilda Djerf transformed a growing social media audience into Djerf Avenue: a global lifestyle brand and an aesthetic that has genuinely shaped internet culture from fashion to beauty to the now-iconic Matilda Djerf hair. 

In this episode, Matilda joins Sammi to share the full story behind Djerf Avenue— from packing orders with friends and family in an empty warehouse to scaling through the pandemic when nobody knew whether consumers would buy blazers during lockdowns. She explains why she never raised venture capital, how she used DMs as market research, and realities of growing a creator-led company at rocketing speed.

Sammi and Matilda also talk about creator burnout, the pressure of tying your personal identity to your company, and the difficult public scrutiny she faced after allegations from former employees. Matilda opens up about leadership, accountability, and what it actually feels like to grow up publicly while running a scaling business. Plus, Matilda shares about getting into community building, influencer culture, and how creators today should think about what parts of their lives belong online and what should stay private. 

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Here’s What Sammi Covers with Matilda:

00:00 Matilda Djerf’s Social Currency

02:03 Partner Message: Mercury for Personal

03:33 Growing Up in a Small Town and Building a Global Audience

04:44 What’s Changed for Creators Since the 2010s

05:32 Why Passion Still Matters More Than Growth Hacks

06:56 Where Matilda Finds Creative Inspiration

08:08 Protecting Your Image in the Age of Social Media

11:30 AI, Copyright, and the Future of Creator Rights

12:00 When Matilda’s Hair Became a Cultural Phenomenon

13:25 Launching Djerf Avenue From an Empty Warehouse

16:29 Why She Never Raised Outside Capital

18:48 Building a Brand Around Community, Not White Space

19:35 Partner Message: Mercury for Business

21:09 Turning Followers Into Customers

22:06 Trusting Her Gut Over a Business Plan

23:49 Launching a Fashion Brand Into a Pandemic

27:13 Why Authentic Community Can’t Be Faked

29:36 How Djerf Avenue Invests in Its Customers

30:46 The Challenges of Scaling 300% Growth

32:20 The Hidden Cost of Returns

34:04 Why Customer Service Remains Human

35:18 Partner Message: Bilt

36:19 Managing a Personal Brand and a Business Brand

38:04 Navigating Public Scrutiny and Leadership Challenges

39:09 The Leadership Lessons She Learned the Hard Way

41:11 Why She Never Considered Walking Away

42:11 The New Social Contract Between Founders and Employees

44:02 Expanding Djerf Avenue Into Beauty

46:27 Selling Beauty Products Without Retail Stores

47:46 What’s Next for Djerf Avenue

49:00 A Week in the Life of Djerf Avenue’s Chief Creative Officer

51:46 Brick and Mortar Dreams

57:10 On Gathered

58:24 Social Currency Corner

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Eugene Remm didn't set out to build a hospitality empire. He started as a bartender, worked in nightlife, and chased success through New York's club scene… until a major failure forced him to rethink everything.

Today, Eugene is the co-founder of CATCH Hospitality Group, the company behind some of the most sought-after restaurants in America, including CATCH, The Corner Store, Or’esh, and The Eighty Six. He breaks down the restaurant formula that most operators get wrong, why "vibe" is actually the last thing you should focus on, and how he thinks about building unforgettable guest experiences. He explains the psychology behind New York's line culture, why restaurant critics have lost their gatekeeping power, and how social media has completely reshaped hospitality.

They also dive into the business side of restaurants: scaling without losing quality, managing celebrity demand, hiring people who genuinely care, and the lessons Eugene learned from failed nightclub ventures and unsuccessful expansion deals. Plus, Eugene shares what happened after Taylor Swift started visiting The Corner Store, why he believes no celebrity has a bigger impact on consumer behavior, and how AI is poised to transform hospitality without replacing the human touch.

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Catch Restaurants, @catch 

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Or'esh, @or.esh 

Here’s What Sammi Covers with Eugene

00:00 Eugene Remm’s Social Currency

02:10 Partner Message: Mercury for Business

03:31 From Bartender to Hospitality Entrepreneur

06:13 How Failure in Nightlife Led to CATCH

08:10 Reinventing a 15-Year-Old Restaurant Brand

10:58 Why Big Restaurants Stopped Working

13:53 The Three Pillars: Food, Service, and Vibe

14:05 Why Guest Experience Is the Hardest Thing to Scale

15:37 Partner Message: Mercury for Personal

16:50 Partner Message: Bilt

17:56 How Eugene Hires People Who Actually Care

20:30 Why Great Teams Beat Great Individuals

21:18 Why Most Restaurants Get Vibe Wrong

22:22 The Art of Curating a Dining Room

23:03 Building a Celebrity-Filled Restaurant Without Chasing Celebrities

25:14 The Million-Dollar Reservation Strategy

26:32 Why Restaurant Critics No Longer Matter

27:27 Michelin Stars vs. Customer Demand

29:14 How Social Media Replaced Traditional Gatekeepers

31:02 Why Eugene Chooses 10 A-Minus Businesses Over One A-Plus

32:45 What’s Next for CATCH Hospitality Group

35:03 Building an LVMH of Restaurant Brands

36:11 The Corner Store’s Viral Rise36:28 The Taylor Swift Effect

38:00 Why Fast Casual Is the Next Frontier

39:54 The Psychology of the “New York Hour”

41:28 Lessons From a Failed Dubai Expansion

43:02 How Tilman Fertitta Changed the Business

44:32 Eugene’s “Constant Gentle Pressure” System

45:28 How AI Will Transform Hospitality

47:53 When You’re Ready to Open Restaurant Number Two

49:31 Why Restaurants Might Be the Hardest Business in the World

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Rick Caruso has spent decades reshaping Los Angeles through projects like The Grove, Americana at Brand, and Palisades Village. In this conversation with Sammi, Rick talks through his entrepreneurial strategy with real estate and beyond.

Rick explains how he built a billion-dollar real estate empire by studying people instead of the industry, why he intentionally ignored traditional mall design rules, and the Walt Disney philosophies that shaped his approach to hospitality. He shares why he believes founders need to be comfortable being over their skis, how criticism actually signals progress, and the surprising rituals he still personally does for guests at his properties.

Then the conversation turns to Los Angeles. Rick gives an unfiltered breakdown of the Pacific Palisades fires, explaining exactly how Palisades Village survived while much of the surrounding area burned. He walks through the fire prevention systems his team built years in advance, the operational decisions that protected the property, and the broader lessons for government competency and crisis management.

Sammi and Rick also discuss why small businesses are increasingly struggling in California, why entrepreneurs are leaving cities like LA and New York, and the political climate that ultimately led Rick to decide not to run for governor. 

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Here’s What Sammi Covers with Rick:

00:00 Rick Caruso’s Social Currency

02:50 Why “Follow Your Passion” Is Bad Advice

05:16 Why Not Knowing the Rules Helped Him Win

08:05 Why Founders Need to Be “Over Their Skis”

09:23 The “Celebrate vs. Isolate” Framework

10:00 Building The Grove Around the Farmers Market

12:08 Why Criticism Means You’re Doing Something Important

14:00 The Hospitality Details Guests Never Notice

18:12 Walt Disney’s Biggest Lesson for Entrepreneurs

22:12 Why People Propose at the Americana Fountain

25:00 Expensive Mistakes

28:32 Why Retail Must Constantly Reinvent Itself

29:14 How Palisades Village Reinvented Retail Layouts

30:00 Why Rick Writes a Fictional Story for Every Project

31:17 What Saved Palisades Village During the Fires

35:05 Why Rick Thinks LA Leadership Failed

37:13 Why Rick Decided Not to Run for Governor

41:00 Why California Needs Business-Minded Leadership

44:18 Solutions to Homelessness in LA

49:29 Why Small Businesses Are Struggling in California

51:45 Rick’s Personal System for Life and Leadership

54:13 Why Entrepreneurs Are Leaving California

56:02 Innovation vs. Naivety for Founders

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Harley Finkelstein believes we’re entering the most important shift in commerce since the invention of online shopping itself.

As President of Shopify, Harley has helped build the infrastructure powering millions of businesses across more than 175 countries. Now, he says AI is about to fundamentally change not only how consumers discover and buy products online— but how “machine customers” might do our shopping for us.

Harley explains why agentic commerce could replace traditional search, his take on the idea that every brand is becoming a media company (featuring a Favorite Daughter case study), and why this new era may reward product quality more than ad spend.

Harley also shares the story of joining Shopify in its earliest days, why founder-led companies consistently outperform, and why he believes modern entrepreneurs can now go from a kitchen-table idea to a multi-billion-dollar company faster than ever before. Plus: the brands he thinks are getting retail right—and the critical “give a sh*t factor” he believes only founders truly have.

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Here’s What Sammi Covers with Harley:

00:00 Harley Finkelstein’s Social Currency

01:57 Partner Message: Mercury

02:30 Growing Up Around Immigrant Entrepreneurs

05:40 Why Harley Went to Law School

08:00 Meeting Shopify Founder Tobi Lütke

12:00 Why Shopify Felt Like a “Superpower”

15:00 Partner Message: Mercury

16:19 Partner Message: Mosh

18:00 The Moment Shopify Became a Generational Company

21:00 From E-Commerce Platform to Commerce Operating System

22:30 Every 26 Seconds a New Entrepreneur Gets Their First Sale

24:00 Why Some Brands Become Media Companies

25:00 Favorite Daughter and the Founder-Led Brand Flywheel

27:00 Why Most Brands Feel Inauthentic

28:30 What Great Retail Brands Understand About Emotion

30:00 Shopify’s OpenAI and ChatGPT Announcement

31:00 What “Agentic Commerce” Actually Means

32:00 AI Personal Shoppers and Curated Buying

35:00 Why AI Could Help Small Brands Win

37:00 The End of Traditional Search?

39:00 How Brands Maintain Identity Inside AI Platforms

41:00 Why Storytelling Matters More in an AI World

42:00 The Rise of Machine Customers

44:00 Why Harley Is a Techno-Optimist

47:30 Why Founder-Led Companies Win

50:00 The Founder “Give a Shit Factor”

51:00 Harley’s Framework for Finding Your Life’s Work

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Todd Kahn took over the commercial responsibility for Coach in March of 2020. Two weeks later, he closed all North America stores. 

Today, Coach CEO Todd Kahn sits down with Sammi to break down the strategy behind one of fashion’s biggest brand turnarounds, and why Coach had to do the exact opposite of conventional growth advice to pull it off. He explains why trying to be “for everyone” almost destroyed the brand, how flash sales quietly trained customers to wait for discounts, and why the company stopped greeting shoppers with coupons entirely during the pandemic.

Todd also shares how Coach rebuilt itself for Gen Z through “expressive luxury,” viral bags like the Tabby and Brooklyn, immersive retail experiences, and unexpected ideas like coffee shops, book charms, and co-creation stations inside stores. Plus: the real reason Gen Z shops in person more than people think, why virality can’t be engineered, and the internal operating system Todd uses to run a nearly $7 billion business.

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Here’s What Sammi Covers with Todd:

00:00 Todd Kahn’s Social Currency

02:30 From Corporate Lawyer to Coach CEO

07:52 Joining Coach During the Financial Crisis

10:00 What Actually Went Wrong at Coach

14:00 Flash Sales, Discounting, and Brand Dilution

15:00 Hiring Stuart Vevers and Resetting Creativity

19:00 Rediscovering Coach’s Brand Codes

20:44 Why Coach Focused on Gen Z

23:00 Closing 250 Stores to Save the Brand

24:00 Why “Stores Are Commercial Activities”

26:00 Cutting 40% of the Assortment

27:10 The “Timeless Gen Z” Strategy

28:40 Taking Over Coach Right Before COVID

29:50 Why Coach Stopped Leading with Discounts

30:20 Building a Billion-Dollar Digital Business

31:00 Why People Bought Handbags During Lockdown

32:00 From Performance Marketing to Brand Building

33:00 Bringing 2.9 Million New Customers Into Coach

34:00 Why Coach Wants to Be Your First Luxury Bag

35:30 The Real Story Behind Bag Charm Mania

38:00 What Actually Creates Virality

39:45 Why Coach Only Does Two Big Campaigns a Year

40:00 What “Expressive Luxury” Really Means

42:00 Why Gen Z Loves Shopping In Person

43:00 Coach Play Stores and Experiential Retail

44:00 The Business Strategy Behind Coach Coffee Shops

47:30 Todd’s Operating System for Leadership

50:22 The Story Behind Coach’s Viral Book Charms

52:00 Why Gen Z Is Returning to Books and Community

Thanks to Mercury for sponsoring this episode! mercury.com 

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Rebecca Hessel Cohen didn’t set out to build a company, she just wanted better bridesmaid dresses. But that small idea turned into LoveShackFancy, a multi-generational, cult-favorite brand with dozens of stores, hundreds of retail partners, and a fiercely loyal community.

Today, Rebecca joins Sammi to break down the unfiltered reality of building a fashion business from scratch. From leaving her dream job at Cosmopolitan, to launching her first collection the same week she had her first child, to schlepping dresses in her car to early customers— this the unfiltered look at what it means to start a business.

They also get into Rebecca’s viral social media moments (including the most epic bat mitzvah), building a brand that resonates from “babies to eighties,” how she evaluates collaborations from Stanley to Victoria's Secret, and what actually makes a retail store feel magical instead of transactional. 

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Here’s What Sammi Covers with Rebecca:

00:00 The Gwyneth Paltrow Moment That Changed Everything

02:03 Partner Message: Mercury for Personal Banking

03:00 Growing Up in Fashion Closets

06:00 Life as a Fashion Editor at Cosmopolitan

10:30 The Bridesmaid Dress That Started It All

14:00 Turning a Side Hustle Into a Business

18:30 Launching a Brand While Having a Baby

20:53 Partner Message: Mercury for Business Banking

22:07 Partner Message: Mosh Bars

23:42 Why LoveShackFancy Wasn’t an Overnight Success

26:00 Building a Team and Scaling the Business

29:00 Opening Retail Stores During COVID

33:00 Dividing Roles With Her Husband

36:00 Building the Beauty Business and Sephora Strategy

38:30 Where Inspiration Actually Comes From

41:00 Designing for “Babies to Eighties”

43:30 How LoveShackFancy Approaches Collaborations

47:00 What Makes a Partnership Actually Work

49:30 Building a Brand Through Community and Retail

52:00 The Power of Experiential Shopping

55:00 Supporting Female Founders Through Trunk Shows

58:00 The Viral Home Tour and Social Media Strategy

01:02:00 Instagram vs. TikTok: How Rebecca Thinks About Both

01:05:00 What She Shares Online (And What She Doesn’t)

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What if the future of work doesn’t look anything like the office jobs we were told to chase?

Steven Schwartz started building businesses as a teenager and eventually turned that obsession into Whop, one of the fastest-growing marketplaces for internet businesses. Today, the company is valued at $1.6 billion and helps thousands of people earn income online.

In this episode, Steven joins Sammi to break down how he met his co-founder on Facebook at 13, why they almost quit Whop after just three months, and how they scaled it into a unicorn backed by names like Peter Thiel and Kevin Hart.

They also unpack the creator economy, why everyone is a creator now, why traditional 9-to-5 career paths are being disrupted, and what “agentic income” could mean in the next era of work. Plus: why Steven thinks the biggest mistake aspiring entrepreneurs make is waiting to feel ready.

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Here’s what Sammi covers with Steven:

00:00 How Steven Met His Co-Founder at 13 on Facebook

03:15 Building Sneaker Bots as a Teenager

06:00 20+ Side Hustles Before Whop

10:30 Almost Quitting Whop After 3 Months

14:00 What Whop Actually Is

19:00 50,000+ New Users Per Day

22:00 The $1.6 Billion Valuation Explained

25:00 Why Stablecoins Matter for Global Business

29:45 Whop Has Created Hundreds of Millionaires

32:30 Advice for New Entrepreneurs

36:00 AI and the End of the Creator Economy

39:30 What “Agentic Income” Means

41:30 The Company That Tried to Buy Whop

43:00 Why Steven Wants to Redefine Work

46:00 Whop Finance and the Future of Money

50:00 Why Creators Shouldn’t Rely on One Platform

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