016. From Bergdorf's to Bitcoin | Emily Dempsey on Career Pivots, Building the Brickell Babes & Why She Finally Went All In

016. From Bergdorf's to Bitcoin | Emily Dempsey on Career Pivots, Building the Brickell Babes & Why She Finally Went All In

Welcome back to STACKED, the show about becoming your own best asset. This week I am going solo. This is the episode I have been meaning to do for a while — my full career arc and the honest version of how I actually got here. I started at Tulane, transferred to Fordham, studied economics, and spent my college years doing every fashion internship I could find in New York City. I landed my dream job as assistant buyer at Bergdorf Goodman's 5F floor where I worked investment banking hours making $40,000 a year and loved every minute of it. I went on to buy off-price fine jewelry at Saks Fifth Avenue before a light bulb moment made me realize I did not want my boss's job, let alone my boss's boss's job. I pivoted into commercial real estate brokerage, spent years cold calling hundreds of numbers a week, and learned more about sales and the art of the deal than I ever expected. Somewhere in the middle of all of that, I started the Brickell Babes in 2022 just to find a good manicure and make some friends. Three years later it had 70,000 women and I was barely treating it like a business. Nine months ago I decided to go all in. This episode is everything I learned along the way and the through line I finally found connecting all of it. Key Topics Covered: — Tulane to Fordham: why she transferred and what New York City gave her from day one — Landing her dream job: assistant buyer at Bergdorf Goodman 5F — contemporary floor, runway shows, $40K salary — Off-price pivot: Saks Fifth Avenue, fine jewelry, private label development — Detox to Retox: the health and fitness Instagram that started monetizing before the pivot — Switching to self-storage sales and learning cold calling at scale — What commercial real estate taught her that fashion never could: sales, thick skin, the art of the deal — The Brickell Babes origin story: started for a manicure, grew to 70,000 women organically — Exploring Bitcoin mining: conferences, evaluating over 50 sites, going down the rabbit hole — The decision nine months ago to go all in on the Brickell Babes — Membership, partnerships, and building a real revenue model — Launching STACKED as the media layer of everything — The through line across every version of her career: helping people become the best version of themselves Timestamps: 00:00 – Welcome + Solo Episode Intro 01:07 – Tulane to Fordham: Why She Transferred & What NYC Gave Her 05:56 – Three Fashion Internships (PR, Black Denim & Elizabeth Sulcer) 10:40 – Landing Her Dream Job: Assistant Buyer at Bergdorf Goodman 5F 12:40 – What She Learned at Bergdorf: P&L, Business Etiquette & Earning Your Stripes 13:12 – Off-Price Pivot: Saks Fifth Avenue, Fine Jewelry & Private Label 14:57 – Barney's Chapter: Buying Intern Before Bergdorf 17:04 – Detox to Retox: The Health & Fitness Instagram Era 18:25 – Pivoting to Commercial Real Estate: NYC & South Florida Retail Leasing 24:46 – What Commercial Real Estate Taught Her 25:55 – What Fashion Taught Her 30:08 – Going Down the Bitcoin Rabbit Hole 31:06 – Evaluating 50+ Sites & Conferences 33:15 – The Decision to Go All In on Brickell Babes 36:47 – The Through Line Across Every Version of Her Career Tags: Emily Dempsey, Brickell Babes, STACKED podcast, from fashion to Bitcoin, career pivot, female entrepreneur, Bergdorf Goodman buyer, Saks Fifth Avenue, commercial real estate, Bitcoin mining, how to build a community, women in business, solo episode, career arc, fashion buyer, entrepreneurship, Brickell Miami, how I got here, women in crypto, Miami entrepreneur Disclaimer:The content shared on this page should not be construed as legal, financial, investment, or medical advice. Your viewing and/or use of this information does not create any kind of client, patient, or fiduciary relationship with us. The contents are intended for general informational purposes only, and you are urged to consult your own advisors or medical professional concerning your situation and specific questions you may have.

015. She Bought Bitcoin at $11 | Tatiana Moroz on Artist Coins & Creator Independence

Welcome back to STACKED, the show about becoming your own best asset. Today I sat down with Tatiana Moroz, singer-songwriter, early Bitcoiner, and founder of Crypto Media Hub. Tatiana is a Berklee College of Music alumna who bought her first Bitcoin at $11 in 2012 through a connection from the Ron Paul campaign. Two years later, she created TatianaCoin on the Bitcoin blockchain—the world's first artist cryptocurrency—and used it to fund her third album, Keep the Faith, paying her entire band in Bitcoin throughout production. In this conversation, we dive into why the creator economy is still broken for musicians, how blockchain gives artists a way to truly own their audience, what fan-funded music looks like in practice, how AI is compressing years of work into days for independent builders, and what it means to build a career without asking permission from labels or platforms. Tatiana also shares her decade-long advocacy for Ross Ulbricht, what his pardon meant for the Bitcoin and libertarian communities, and why she believes Bitcoin is more than an investment—it's a revolution. This is a beginner-friendly conversation about music, money, creative ownership, and the future of independent creators. Key Topics Covered: — Origin story: Berklee, libertarian politics, and how the Ron Paul campaign led directly to Bitcoin — Buying Bitcoin at $11 through a BitPay sponsorship and falling down the Bitcoin rabbit hole — The DIY creator trap: building audiences on platforms that can censor or cut you off — TatianaCoin: creating the world's first artist cryptocurrency on Bitcoin in 2014 — Blockchain explained simply: digital scarcity, finite ownership, and why it matters — Funding Keep the Faith: the first album funded and paid for entirely with Bitcoin — Why touring is often a social media flex rather than a sustainable income model for artists — Tokenization in music vs. gaming: why network effects remain the biggest challenge — AI as a force multiplier for indie entrepreneurs: 36 hours instead of 2 years and $500K — Building a censorship-free, blockchain-powered platform for artist independence — Ross Ulbricht, Silk Road, and more than a decade of advocacy leading to his pardon — Bitcoin for beginners: wallets, self-custody, trusted communities, and getting started safely Timestamps: 00:00:00 – Welcome + Introducing Tatiana Moroz 00:01:00 – Origin: Berklee, Music as a Message & Reading Dystopian Novels 00:02:21 – Libertarian Politics & Singing for the Ron Paul Campaign 00:04:37 – The DIY Creator Trap: Building Audiences on Platforms You Don't Own 00:07:01 – Blockchain Explained: Scarcity, Finite Copies & Why It Matters for Creators 00:07:38 – Creating TatianaCoin in 2014: The World's First Artist Cryptocurrency 00:12:51 – AI as a Builder's Tool: 36 Hours vs. 2 Years and $500K 00:17:40 – Building a Censorship-Free Platform for Artist Independence 00:35:53 – Bitcoin for Beginners: Wallets, Self-Custody & Trusted Communities 00:42:46 – Teaching Kids About Bitcoin & Ghost Trading as a Starting Point 00:44:24 – Ross Ulbricht, Silk Road & Over 10 Years of Advocacy Before the Pardon 00:48:43 – Lightning Round Tags:Tatiana Moroz, TatianaCoin, Bitcoin for artists, creator economy, fan-funded music, artist cryptocurrency, music and Bitcoin, creator independence, self-custody, blockchain for musicians, indie artist, music business, financial sovereignty, Bitcoin beginner, Crypto Media Hub, STACKED podcast, Brickell Babes, Ross Ulbricht pardon, Bitcoin at $11, direct-to-fan monetizationDisclaimer: The content shared on this page should not be construed as legal, financial, investment, or medical advice. Your viewing and/or use of this information does not create any kind of client, patient, or fiduciary relationship with us. The contents are intended for general informational purposes only, and you are urged to consult your own advisors or medical professional concerning your situation and specific questions you may have.

EP 014. She Lost Everything and Built Something Greater │ Karine Nissim on Grief as a Business Catalyst, Building Daynu & The Unsexy Side of Consumer Brands

Welcome back to STACKED, the show about becoming your own best asset. Today I sat down with Karine Nissim, serial entrepreneur, award-winning writer, and podcaster. Karine grew up between Israel, New Jersey, and South Florida, studied filmmaking in Los Angeles, and built her first real company there alongside her late husband Aaron. That company was Dog Vacay, the Airbnb for pets, which raised $50 million and eventually merged with Rover. During the pandemic, she launched Shmask on her own, a shirt with a built-in mask for kids, and sold over $100,000 in a single day on the Today Show. Then Aaron passed away unexpectedly, and everything changed. In this conversation we got into everything: the unsexy logistics behind consumer brands, what she learned about herself as an operator, why your network is always the real shortcut, the grief that led her to build DayNew, and why she believes done is always better than perfect. Karine is one of the most generous and clear-eyed people I know, and this conversation will stay with me. Key Topics Covered🔹 From Israel to New Jersey, South Florida, and LA: growing up in an entrepreneurial immigrant family — How Dog Vacay was born from a personal problem and scaled to raise $50 million — Building with a spouse: balancing egos, defining roles, and why most co-founder relationships fail — Why "done is better than perfect" and how to overcome analysis paralysis — Shmask: turning a midnight idea into a Today Show feature and $100K+ in sales in a single day — The unexpected loss of her husband and the year of survival that followed — How writing through grief became the foundation for DayNew — The two things every person needs during difficult times: connection and consistency — Understanding your strengths as an operator: launching vs. managing day-to-day operations — Why in-person networking remains one of the highest-leverage growth strategies — How negative self-talk prevents the alignment and growth you're seeking — Finding your North Star and allowing your purpose to evolve over time — Lightning Round: Peer Support vs. Expert-Led, CAC vs. LTV, Miami vs. LA Timestamps: 00:00 – Welcome + Introducing Karine Nissim 01:54 – From Israel to LA: Karine's Origin Story 03:00 – Growing Up in an Entrepreneurial Immigrant Family 03:54 – The Personal Problem That Sparked Dog Vacay 04:28 – Raising $50M to Build the Airbnb for Pets 06:11 – Building a Company with Your Spouse: Roles, Ego & Trust 12:02 – Escaping Analysis Paralysis & Making Better Decisions 13:50 – Why Done Is Better Than Perfect 20:51 – Shmask: From a Midnight Idea to $100K+ in One Day 26:05 – Losing Aaron & Navigating a Year of Survival 29:38 – How Writing Through Grief Built an Audience 32:31 – What Is DayNew? AI, Community & Practical Support for Healing 34:44 – The Two Things Every Human Needs During Hard Times 35:51 – Why Acceptance Is the Most Important Step in Healing 44:25 – Knowing Yourself as an Operator: Launching vs Running 48:34 – Negative Self-Talk & the Language of Becoming 50:26 – Finding Your North Star & Letting It Evolve 58:46 – Lightning Round 01:01:41 – Where to Find Karine Nissim Tags: Karine Nissim, DayNew app, grief and entrepreneurship, serial entrepreneur, Dog Vacay, Shmask, consumer brands, female founder, how to build a startup, women in business, turning pain into purpose, entrepreneur mindset, healing tech, grief support, personal brand, community building, STACKED podcast, Brickell Babes, done is better than perfect, startup founder story Disclaimer:The content shared on this page should not be construed as legal, financial, investment, or medical advice. Your viewing and/or use of this information does not create any kind of client, patient, or fiduciary relationship with us. The contents are intended for general informational purposes only, and you are urged to consult your own advisors or medical professional concerning your situation and specific questions you may have.

EP 013. He Built a Top 10 Podcast From Scratch | Scott D. Clary on The Mindset Behind 30 Million Downloads, Content Strategy, & The Creator-Operator Model

Welcome back to STACKED, the show about becoming your own best asset. Today I sat down with Scott D. Clary, host of Success Story Podcast, one of the Top 10 business shows on earth with over 30 million downloads and 321,000 newsletter subscribers. Scott grew up in Ottawa in a family of government workers, nearly went to law school, then spent a decade moving through enterprise sales, startup CRO roles, and two acquisitions.  When his last company was about to be sold, he had 12 months to figure out what came next. He chose to start a podcast with no audience, no product, and no plan, just a belief that attention compounds. Moving forward in this conversation we got into everything: content strategy, distribution, the locus of control mindset he says every successful person he has ever interviewed shares, why he says riches are always in the niches, and the framework behind giving equity that I wish I had heard earlier. This is the content business playbook in real life: the good calls, the frameworks, and the one thing Scott says you should never give away cheaply. Key Topics Covered: — Ottawa to Miami: growing up in a government household and choosing tech over law school — Why he started the podcast before he had a product or a plan — Teaching a younger version of yourself as the content strategy that works — Video as the highest-trust content medium short of a face-to-face meeting — Locus of control: internal vs external and why every successful entrepreneur has it — Everything is you pushed out: how your internal belief system creates external results — Why entrepreneurship is not logical and what kind of person survives it anyway — Niche first, go broad later: how Gary Vee, Grant Cardone and Hormozi all started — Distribution: 30 to 40 pieces of content per day across 7 platforms — Collaboration strategy: always match medium to medium for maximum conversion — Equity as a marriage: when to give it, when to refuse, and how to evaluate the deal — Staying in the game long enough: why 10 to 15 years compounded beats one big swing Timestamps: 00:00 – Welcome + Introducing Scott D. Clary 00:53 – Ottawa Origin Story: Growing Up in a Government Family, Pre-Law Plans & Choosing Tech 03:04 – From Bell Canada to Startup CRO Roles and a Successful Acquisition 05:21 – Why Scott Started a Podcast With No Product, Audience, or Plan 06:52 – Advice to His Younger Self: Finding Your Content Avatar 07:44 – Why Video Is the Highest-Trust Content Medium 08:10 – Parasocial Relationships and the Creators Who Master Them 33:08 – Locus of Control: Internal vs. External Mindsets Explained 36:48 – "Everything Is You Pushed Out": Belief, Action & Compounding Results 39:17 – Staying in the Game Long Enough: The Million-Dollar Creator Math 42:00 – Why Entrepreneurship Requires a Certain Level of Delusion 49:26 – Distribution Strategy: Publishing 30–40 Pieces of Content Per Day 54:13 – Collaboration: Why Medium-to-Medium Partnerships Drive Growth 55:58 – Equity & When to Say No: The Podcast Equity Offer Story 57:28 – Lightning Round: Niches, Anchors, Big Deals, Newsletters vs. Social 1:02:26 – Where to Find Scott D. Clary Tags: Scott D. Clary, Success Story Podcast, content strategy, podcast growth, locus of control, creator economy, entrepreneur mindset, how to build a podcast, personal brand, media business, organic growth, niche down, how to grow on social media, entrepreneurship, STACKED podcast, Brickell Babes, female founders, women in business, creator operator, podcast monetization Disclaimer. The content shared on this page should not be construed as legal, financial, investment, or medical advice. Your viewing and/or use of this information does not create any kind of client, patient, or fiduciary relationship with us. The contents are intended for general informational purposes only, and you are urged to consult your own advisors or medical professional concerning your situation and specific questions you may have.

012. My AI Stack: The Exact Systems, Automations & Workflows Running My Business on a Lean Team | Emily Dempsey

Welcome back to STACKED, the show about becoming your own best asset. This week I am pulling back the curtain on Part 2 of how I use AI in my business — and this one gets specific. I walk you through the exact Claude systems, automations, and workflows my team uses across partnerships, content production, podcast operations, and customer service. We are talking brand voice documents as sources of truth, N8N automations connected to Claude agents, Otter AI meeting notes that turn into Gmail drafts before I wake up, and a content pipeline that saves this team 40+ hours per week. Before I built this stack, executing the volume we are doing today would have required 25 people. We do it with a lean team. I also tell you the three things I will never hand off to AI — and why that line matters more the deeper you go. If you run a business, a brand, a community, or a content operation of any size, this episode is the blueprint. Key Topics Covered: — Why I moved from ChatGPT to Claude and what changed — How to set up Claude as a desktop app and connect your integrations — Creating a brand voice document — the single most important thing you can do before using AI — The "sources of truth" system: media kit, partnership stack, SOPs, and how to train your Claude — Partnership workflow: how Otter AI + Claude + N8N turns a sales meeting into a draft email — How Claude audits pricing and flags proposal errors before they go out — The podcast production pipeline: from raw transcript to copy template to Canva — fully automated — Customer service automation: N8N + Claude agent + Slack approval loop — What I will never let AI touch: external emails, negotiation decisions, emotionally sensitive comms, brand taste — The 25-people stat: what a lean AI-powered team can actually do — Why future jobs are shifting from execution to system architecture — What is coming next: moving Claude agents off desktop and into the cloud for the whole team 00:00  Welcome + solo episode intro 00:42  Why I left ChatGPT after almost2 years and moved to Claude 03:08  Setting up Claude desktop:integrations, connectors, and your folder of sources of truth 05:58  Brand voice documents: the mostimportant thing you build before touching AI 08:22  Use case 1: Partnerships — OtterAI + Claude + N8N meeting-to-email automation 11:35  Pricing strategy + proposalaudit: how Claude flags errors before they go out 16:31  Use case 2: Content production —the full podcast-to-Canva pipeline 19:54  How the copy template systemworks and the 40-hours-per-week save 24:10  Use case 3: Operations — Zapiervs N8N and why we switched 26:03  Customer service automation: N8N+ Claude + Slack approval loop 28:08  What I will NEVER let AI touch 30:00  Unexpected wins: sleepingbetter, thinking more clearly, better data 31:47  The 25-people stat and the realROI of this stack 33:44  Why future jobs are aboutarchitecting, not executing 34:27  What's coming next: team-wideClaude agents in the cloud 35:03  Outro Tags: Emily Dempsey, STACKED podcast, AI for business, Claude AI, how to use Claude, AI automation, N8N workflow, Otter AI, AI tools for entrepreneurs, small team operations, AI content production, brand voice AI, podcast production automation, Brickell Babes, women entrepreneurs, AI systems, business automation 2026, Claude vs ChatGPT, AI workflow for founders Disclaimer: Disclaimer. The content shared on this page should not be construed as legal, financial, investment, or medical advice. Your viewing and/or use of this information does not create any kind of client, patient, or fiduciary relationship with us. The contents are intended for general informational purposes only, and you are urged to consult your own advisors concerning your situation and specific questions you may have.