Harley Finkelstein (Shopify) on AI Shopping Agents, Merit-Based Commerce, and the “Give a Sh*t Factor” That Makes Founder-Led Companies Win

Jamie Siminoff (Ring) on Near Bankruptcy, Amazon, and Shark Tank

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. Follow Sammi Cohen on Instagram  [https://www.instagram.com/sammicohentalks/?hl=en] Subscribe to the Social Currency newsletter [https://socialcurrency.beehiiv.com/] Check out Jamie’s book Ding Dong [https://www.amazon.com/Ding-Dong-Shark-Reject-Everyones-ebook/dp/B0FX5ZC43Z] 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 Thanks to Our Sponsors! Mercury: mercury.com [http://mercury.com]  Rula: rula.com/socialcurrency [http://rula.com/socialcurrency] Bilt:  joinbilt.com/socialcurrency [http://joinbilt.com/socialcurrency]  Shopify: shopify.com/socialcurrency [http://shopify.com/socialcurrency]  Learn more about your ad choices. Visit megaphone.fm/adchoices [https://megaphone.fm/adchoices]

Peter Semple (Depop) on Scaling Beyond Gen Z, the CMO to CEO Pipeline, and the eBay Deal

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. Follow Sammi Cohen on Instagram  [https://www.instagram.com/sammicohentalks/?hl=en] Subscribe to the Social Currency newsletter [https://socialcurrency.beehiiv.com/] Follow Peter [https://www.linkedin.com/in/petersemple/] and Depop [https://www.depop.com/] 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” Thanks to Our Sponsors! Mercury: mercury.com [http://mercury.com]  Rula: rula.com/socialcurrency [http://rula.com/socialcurrency] Bilt:  joinbilt.com/socialcurrency [http://joinbilt.com/socialcurrency]  Shopify: shopify.com/socialcurrency [http://shopify.com/socialcurrency] Learn more about your ad choices. Visit megaphone.fm/adchoices [https://megaphone.fm/adchoices]

Gary Vaynerchuk (VaynerX) on the Next Digital Gold Rush, AI, and Intellectual Property

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. Follow Sammi Cohen on Instagram  [https://www.instagram.com/sammicohentalks/?hl=en] Subscribe to the Social Currency newsletter [https://socialcurrency.beehiiv.com/] Follow Gary Vaynerchuk [https://www.instagram.com/garyvee/?hl=en] and VeeFriends [https://www.instagram.com/veefriends/?hl=en] 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 Thanks to Our Sponsors! Mercury: mercury.com [http://mercury.com]  Rula: rula.com/socialcurrency [http://rula.com/socialcurrency] Bilt:  joinbilt.com/socialcurrency [http://joinbilt.com/socialcurrency]  Shopify: shopify.com/socialcurrency [http://shopify.com/socialcurrency] Learn more about your ad choices. Visit megaphone.fm/adchoices [https://megaphone.fm/adchoices]

Matilda Djerf (Djerf Avenue) on Creator-Led Brands, Secrets Behind 300% Growth and Tough Lessons in Entrepreneurship

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.  Follow Sammi Cohen on Instagram  [https://www.instagram.com/sammicohentalks/?hl=en] Subscribe to the Social Currency newsletter [https://socialcurrency.beehiiv.com/] Follow Matilda Djerf [https://www.instagram.com/matildadjerf/?hl=en] and Djerf Avenue [https://www.instagram.com/djerfavenue/?hl=en] 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 Thanks to Our Sponsors! Mercury: mercury.com [http://mercury.com] Bilt:  joinbilt.com/socialcurrency [http://joinbilt.com/socialcurrency]  Learn more about your ad choices. Visit megaphone.fm/adchoices [https://megaphone.fm/adchoices]

Eugene Remm (CATCH) on the Business of Vibe, Restaurant Economics and Critics Who Gatekeep

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. Follow Sammi Cohen on Instagram  [https://www.instagram.com/sammicohentalks/?hl=en] Subscribe to the Social Currency newsletter [https://socialcurrency.beehiiv.com/]  Follow Eugene’s Work: Catch Restaurants [http://catchrestaurants.com], @catch [https://www.instagram.com/catch/?hl=en]  The Corner Store [http://thecornerstoresoho.com], @thecornerstore [https://www.instagram.com/thecornerstore/?hl=en] The Eighty Six [http://the86.nyc], @the86.nyc [https://www.instagram.com/the86.nyc/?hl=en]  Or'esh [http://oresh.com], @or.esh [https://www.instagram.com/or.esh/?hl=en]  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 Thanks to Our Sponsors! Mercury: mercury.com [http://mercury.com] Bilt:  joinbilt.com/socialcurrency [http://joinbilt.com/socialcurrency]  Learn more about your ad choices. Visit megaphone.fm/adchoices [https://megaphone.fm/adchoices]