STACKED with Emily Dempsey

STACKED with Emily Dempsey

Stacked with Emily Dempsey is the podcast at the intersection of Bitcoin, wealth-building, entrepreneurship, and living well. Emily went from Bergdorf Goodman fashion buyer to Bitcoin miner and founder — and now she's your filter. Expert-level conversations made actionable. No jargon, no shilling, no fluff. Just clarity on money, power, and what's coming next. New episodes weekly. Let's get stacked. For educational purposes only. Not financial advice.

Episodes

  1. 005. Are You Dating the Wrong Person? | Maria Sosa on Love Bombing, Non-Negotiables & Red Flags

    4D AGO

    005. Are You Dating the Wrong Person? | Maria Sosa on Love Bombing, Non-Negotiables & Red Flags

    Welcome to Episode 005 of STACKED — the show about becoming your own best asset. Emily sits down with Maria Sosa, AKA Holistically Grace — couples therapist, divorce counselor, and author helping thousands of women navigate love and heartbreak. Maria left a father-chosen marketing career to become a couples therapist — then got divorced while her following was growing. She hid it, shared it, and the response changed everything. This episode is a real, unfiltered conversation about modern relationships, emotional honesty, and the work it actually takes to build a life you love — with a partner, and with yourself. Connect with Maria Sosa: Instagram: https://www.instagram.com/HolisticallyGrace/ X: https://x.com/holistically_g TikTok: TikTok - Make Your Day Website: https://www.holisticallygrace.com/ Connect with us:  Subscribe to the STACKED newsletter: weekly headlines on Bitcoin, digital assets, business, and wellness delivered every Sunday and Wednesday. Subscribe at https://stackedassets.co/ Follow Us:  YouTube:  https://www.youtube.com/@stacked-assets Instagram: https://www.instagram.com/stackedassets TikTok: https://www.tiktok.com/@stacked.assets Follow Emily Dempsey:  Instagram: https://www.instagram.com/emilydempsey X: https://x.com/EmilyDempsey LinkedIn:https://www.linkedin.com/in/emily-j-dempsey/ Follow The Brickell Babes:  Become A Member:www.thebrickellbabes.com/membership Instagram: https://www.instagram.com/thebrickellbabes/ TikTok: https://www.tiktok.com/@thebrickellbabes Follow Maria Sosa / Holistically Grace:  Instagram: / holisticallygrace  Website: holisticallygrace.com WHAT WE COVER: — How Maria's father chose her career, why she walked away, and what drew her to studying human irrationality. — Divorcing publicly as a couples therapist, the shame she carried, and why sharing it brought her closer to her community. — Why not every ended friendship was toxic — and the distinction that changed how they both see it. — Why showing up as yourself early in dating is the most strategic move, and what it costs when you don't. — How to find your true non-negotiables, why they're deeply personal, and the difference between compromising and self-abandonment. — Being childfree, dating with that truth upfront, and what Emily discovered when her partner changed his mind about kids. — Why Maria has a standing "energy audit" every Sunday at 3 PM, and what intentional relationship maintenance looks like. — Sparklers vs. fireworks, name the feeling vs. fix the problem, somatic tools vs. scripts, slow burn vs. instant chemistry. TIMESTAMPS: 00:00:00 — Welcome to STACKED  00:00:30 — Introducing Maria Sosa / Holistically Grace  00:02:30 — Draining vs. depleting relationships  00:08:30 — Going through a divorce as a couples therapist  00:10:45 — Building a social media following: private vs. vulnerable  00:15:50 — Being the oldest child and the people-pleasing trap  00:18:20 — How to raise your tolerance for discomfort  00:21:45 — Early dating: show up as yourself, not your representative  00:24:17 — Compromise vs. compromising yourself  00:33:17 — The childfree decision  00:37:21 — Emily's egg-freezing story  00:44:40 — Maria's Bumble profile 00:47:07 — Life as a science experiment  00:49:35 — Love bombing vs. genuine enthusiasm  00:55:34 — What to do when you can't unsee the red flags  00:59:42 — The honeymoon period — no big decisions  01:01:21 — 50/50 relationships  01:08:26 — Financial literacy as self-protection for women  01:10:01 — Lightning round Subscribe for new episodes every Tuesday at 7AM EST. DISCLAIMER This is educational content, not financial or therapeutic advice. Consult a qualified professional before making personal or financial decisions.

    1h 23m
  2. 004. There Is Money Hanging in Your Closet | Pickle Co-Founder Julia O’Mara on Passive Income, Peer-to-Peer Fashion Rental & Raising an $8M Round After Bootstrapping for 2 Years

    MAR 31

    004. There Is Money Hanging in Your Closet | Pickle Co-Founder Julia O’Mara on Passive Income, Peer-to-Peer Fashion Rental & Raising an $8M Round After Bootstrapping for 2 Years

    Welcome to Episode 004 of STACKED — the show about becoming your own best asset. Today Emily sits down with Julia O’Mara, co-founder and COO of Pickle, the peer-to-peer fashion rental marketplace that is Airbnb for your closet. At 23, Julia left a senior product manager role at Blackstone to build a platform that lets women make passive income renting out pieces they already own. She bootstrapped for 2.5 years on $200,000, personally delivered the first 1,500 orders across New York City, ran out of money three times, and raised $12 million in seed funding before closing a Series A in March. Julia has been named to Forbes 30 Under 30 and the Inc. Female Founders List. This episode is your complete closet-to-cash playbook Connect with us: Subscribe to the STACKED newsletter - weekly headlines on Bitcoin, digital assets, business, and wellness delivered every Sunday and Wednesday. Subscribe at https://stackedassets.co/ Follow Us: YouTube: https://www.youtube.com/@stacked-assets Instagram: https://www.instagram.com/stackedassets TikTok: https://www.tiktok.com/@stacked.assets Follow Emily Dempsey: Instagram: https://www.instagram.com/emilydempsey X: https://x.com/EmilyDempsey LinkedIn: https://www.linkedin.com/in/emily-j-dempsey/ Follow The Brickell Babes: Become A Member: www.thebrickellbabes.com/membership Instagram: https://www.instagram.com/thebrickellbabes/ TikTok: https://www.tiktok.com/@thebrickellbabes WHAT WE COVER: — How COVID revealed that Julia was more passionate about her colleagues than her actual work, and how a conversation with her co-founder changed everything. —The first app flopped. But inside the failure was the data that became Pickle. Julia explains how to read the signal inside the mess. —The nano influencer hack, the green balloons in SoHo, Brian's apartment as a warehouse, and delivering 1,500 orders on the NYC subway. —The 10 to 20% of retail framework. A $400 dress rents for $50 to $80. Both sides win. —The Pickle Protection Policy, reviews, lender controls, and the condition reporting feature that changes the game. —How to download the app, upload your first items using AI autofill, and start earning this week. —Ship by Friday vs. perfect V1, creator seeding vs. paid ads, city by city vs. nationwide growth. TIMESTAMPS: 00:00 — Welcome to STACKED 00:30 — Introducing Julia O’Mara and Pickle 02:30 — Julia's background and twin sister 04:00 — Engineering at Penn and the entrepreneurship minor 06:30 — Joining Blackstone out of college 08:00 — COVID and the realization that prompted the leap 09:30 — Meeting co-founder Brian and the first conversation about Pickle 11:00 — Pickle Poll: the first app and why it failed 14:00 — The pivot signal: comments in the polling app 16:00 — Leaving Blackstone and launching the rental MVP 18:00 — Bootstrapping $200K for 2.5 years 20:00 — Getting the first lenders: friends' wardrobes and green balloons in SoHo 23:00 — Brian's apartment as the Pickle warehouse 25:00 — Delivering 1,500 orders across NYC on the subway 27:00 — How 85 to 90% organic growth happened 29:00 — The viral moment that unlocked the seed round 31:00 — Raising $8 million in seed funding 33:00 — Pricing strategy: 10 to 20% of retail 35:00 — Geographic expansion: NY to LA to Miami 37:00 — Growth fellowship program and next cities 39:00 — Trust and safety: Pickle Protection Policy 43:00 — Closing the Series A in March 44:00 — Julia's COO role and weekly metrics ritual 46:00 — Wellness as a founder: movement, water, something green 48:00 — Closet to Cash: 3 steps to start this week 51:00 — Top lenders making thousands a month 53:00 — 1 in 4 women in NYC has downloaded Pickle 54:00 — Lightning round 56:00 — Where to find Julia and download Pickle Subscribe for new episodes every Tuesday at 7AM EST. DISCLAIMER This is educational content, not financial advice. Consult a qualified professional before making business or financial decisions.

    48 min
  3. 003. The Man Who Called FTX, Luna & Celsius | Swan Bitcoin’s Cory Klippsten on Real Bitcoin, Self-Custody & Long-Term Wealth

    MAR 24

    003. The Man Who Called FTX, Luna & Celsius | Swan Bitcoin’s Cory Klippsten on Real Bitcoin, Self-Custody & Long-Term Wealth

    Welcome back to STACKED, the show about becoming your own best asset. Today, Emily sits down with Cory Klippsten, founder and CEO of Swan Bitcoin — the wealth platform that has purchased $4.5 billion in Bitcoin for families and businesses building long-term wealth. Before Swan, Cory spent 15 years at Google, McKinsey, Microsoft, and Morgan Stanley, and earned his MBA from the University of Chicago. He is one of the most respected and feared voices in the Bitcoin space: the man who publicly called out the Luna Ponzi, warned about Celsius weeks before it collapsed, and nicknamed Sam Bankman-Fried "Scambankster Fraud" months before FTX went to zero. This episode is your clean, beginner-friendly Bitcoin playbook. No hype. No fluff. Just the truth about what Bitcoin is, how to actually own it, how to protect it, and how to think about it as a long-term wealth strategy. Connect with us: Subscribe to the STACKED newsletter — weekly headlines on Bitcoin, digital assets, business, and wellness, delivered every Sunday and Wednesday. Subscribe at ⁠⁠www.stackedassets.co ⁠⁠ Follow Us: YouTube: ⁠⁠https://www.youtube.com/@stacked-assets⁠⁠ Instagram: ⁠⁠https://www.instagram.com/stackedassets/⁠⁠ TikTok: ⁠⁠https://www.tiktok.com/@stacked.assets⁠⁠ Follow Emily Dempsey: Instagram: ⁠⁠https://www.instagram.com/emilydempsey⁠⁠ X: ⁠⁠⁠https://x.com/EmilyDempsey⁠⁠⁠ LinkedIn: ⁠⁠https://www.linkedin.com/in/emily-j-dempsey/⁠⁠ Follow The Brickell Babes: ⁠⁠⁠⁠⁠ Become A Member: ⁠⁠www.thebrickellbabes.com⁠⁠/membership⁠⁠ Instagram: ⁠⁠https://www.instagram.com/thebrickellbabes/⁠⁠ TikTok: ⁠⁠⁠https://www.tiktok.com/thebrickellbabes/⁠⁠ KEY TOPICS COVERED — Swan Bitcoin: what it is, who it's built for, and the difference between real vs. paper Bitcoin. — Cory's origin story and why it took 11 months to get truly convicted. — Bitcoin vs. crypto: why they're fundamentally different. — Swan's operating principle, content-led acquisition, and AI integration. — Why Bitcoin is a monetary revolution — not a product — and why AI makes it more valuable. — Cory's fraud calls: Luna, Celsius, FTX, and the Alameda balance sheet. — Swan products: brokerage, IRAs, Swan Safe, Swan Vault, Swan Generations, Swan Trinity, and multisig explained. — Regulation, cap gains, and the lightning round. TIMESTAMPS 00:00 — Welcome to STACKED 02:45 — What Swan Bitcoin does and who it's built for 04:45 — Real Bitcoin vs. paper Bitcoin 06:00 — Cory's origin story: leaving Google in 2013 09:00 — Why it took 11 months to get truly convicted 10:30 — The moment Cory knew he wanted to build Swan 13:00 — Content-led acquisition and education for wealthy clients 17:00 — The Bitcoin ETF as the Netscape moment — why we're in 1995 19:00 — How institutional ownership is changing price dynamics 22:30 — Emily's Bitcoin origin story: $500 to get her Instagram back 29:00 — AI at Swan: agents, swarms, what changed in the last 2 months 34:00 — Why deflationary economics make scarce assets more valuable 36:00 — Bitcoin as monetary revolution, not product — why adoption takes decades 42:00 — The Triffin dilemma and the hidden cost of dollar reserve status 43:00 — Cory's reputation as Bitcoin's no-BS guy 49:00 — SBF and FTX: calling him a liar before the full story broke 56:00 — Swan products: brokerage, IRAs, tax loss harvesting, limit orders 57:00 — Rolling an old 401k into a Bitcoin IRA through Swan 58:00 — Swan Safe, Swan Vault, and multisig explained 01:01:00 — Swan Trinity: the Rolls-Royce of custody for families and family offices 01:05:00 — Working with trust companies, estate attorneys, and Bitcoin-savvy RIAs 01:06:00 — Swan's New York expansion 01:09:00 — Regulation and Bitcoin: why clarity has only been positive 01:11:00 — The cap gains tax problem and tax-free Bitcoin spending 01:14:00 — Where to find Cory and Swan Bitcoin Disclaimer: This podcast is educational content, not financial advice. Do your own research. Consult a qualified financial professional before making investment decisions.

    1h 16m
  4. 002. YOUR GUT IS RUINING YOUR HORMONES | Ella Davar

    MAR 17

    002. YOUR GUT IS RUINING YOUR HORMONES | Ella Davar

    Welcome back to STACKED — the show about becoming your own best asset. In this episode, Emily sits down with Ella Davar, registered dietitian, longevity expert, and founder of the Gut Brain Method. Ella is a former Wall Street professional who left to earn her Registered Dietician degree from NYU. She is a top nutritionist in Miami and the author of five books including The Foodie Diet. Ella is president of the Global Longevity Association, and has led programs at top wellness destinations in Palm Beach, Switzerland, Miami, and the White House. EP 002 is a 101 on the gut-brain connection, personalized nutrition, and the small levers that actually move energy, focus, and mood for busy women — without turning your life into a lab project. Connect with Ella Davar Instagram: @ella.davar @Gut.Brain.Method @global.longevity.association Website: Use code FIRST for 10% off everything on Ella's site: ⁠gutbrainmethod.com⁠ Connect With Us: Subscribe to the STACKED newsletter — weekly headlines on Bitcoin, digital assets, business, and wellness, delivered every Sunday and Wednesday. Subscribe at⁠ ⁠www.stackedassets.co⁠⁠ Follow Us: YouTube:⁠ ⁠https://www.youtube.com/@stacked-assets⁠⁠ Instagram:⁠ ⁠https://www.instagram.com/stackedassets/⁠⁠ TikTok:⁠ ⁠https://www.tiktok.com/@stacked.assets⁠⁠ Follow Emily Dempsey: Instagram:⁠ ⁠https://www.instagram.com/emilydempsey⁠⁠ X:⁠ ⁠⁠https://x.com/EmilyDempsey⁠⁠⁠ LinkedIn:⁠ ⁠https://www.linkedin.com/in/emily-j-dempsey/⁠⁠ Follow The Brickell Babes:⁠ ⁠⁠⁠⁠ Become A Member: ⁠⁠www.thebrickellbabes.com⁠⁠/membership⁠⁠ Instagram:⁠ ⁠https://www.instagram.com/thebrickellbabes/ ⁠⁠TikTok:⁠ ⁠⁠https://www.tiktok.com/thebrickellbabes/⁠⁠⁠ KEY TOPICS COVERED Ella's origin story: from Wall Street wealth management to registered dietitian and gut health expert The personal health crises that built her expertise: burnout, bloating, skin issues, and a self-diagnosed parasite infection Breathwork for digestion: 3 deep breaths before meals to shift into rest and digest mode Why fight-or-flight mode shuts down digestion — and what chronic stress does to enzymatic function Longevity non-negotiables: sleep, nutrition, and exercise — and why most people still do not have these figured out Top antioxidants: dark leafy greens, sulforaphane, berries, plant-based proteins, and the restaurant berry hack The oat milk truth and the milk ranking: cow's milk, A2, goat and sheep, organic soy, cashew, macadamia Lactose intolerance vs. milk protein intolerance — they are completely different things Continuous glucose monitoring (CGM): what it is, how it works, and what it shows in 14 to 28 days The gut-estrogen connection: beta-glucuronidase, estrogen detoxification, and PMS TIMESTAMPS 00:00 Welcome to STACKED 01:08 Introducing Ella Davar and the Gut Brain Method 02:35 How Emily and Ella met at the 2023 Brickell Babes conference 03:00 Ella's origin story: Wall Street to registered dietitian 09:30 Why social media gut health advice is usually not for you 10:30 The 5 aspects of optimal gut health 11:40 Emily's celiac story: the doctors who missed it 16:00 The gut-brain axis: neurons, enteric nervous system, vagus nerve 22:00 The Gut Brain Method: the 2-session one-on-one program 26:00 The 9-week certification program 28:00 Books, membership, and how the longevity dinners started 36:00 Sleep queen: Oura Ring and no alarm clocks 38:30 Top antioxidants: greens, berries, plant-based proteins 48:30 Modern diagnostics vs. ancient practices 51:00 Continuous glucose monitoring and why Emily ditched oat milk 55:00 Milk ranking: cow's, A2, goat, sheep, organic soy, cashew, macadamia 58:00 Lactose intolerance vs. milk protein intolerance 01:06:00 Feminine vs. masculine energy: human being vs. human doing 01:11:30 Lightning round: this or that 01:21:00 Where to find Ella and the Gut Brain Method DISCLAIMER This podcast is educational content, not financial advice. Do your own research; know your time horizon and risk tolerance.

    1h 9m
  5. 001. Bergdorf's to Bitcoin: The Origin Story | How I Built a 70K Community & Went Deep on Bitcoin Mining

    MAR 10

    001. Bergdorf's to Bitcoin: The Origin Story | How I Built a 70K Community & Went Deep on Bitcoin Mining

    Welcome to Episode 1 of STACKED — the show about becoming your own best asset. I'm Emily Dempsey, and this is the full origin story of how this podcast came to be.  How a girl from Chicago who grew up around finance,  and wanted nothing to do with it — ended up buying fashion at Bergdorf Goodman, building South Florida's largest women's network from a Facebook group, and spending two years making herself an expert in Bitcoin, cryptocurrency, and digital assets. This episode is the foundation. Everything on STACKED builds from here. Let’s get stacked.  Connect with us: Subscribe to the STACKED newsletter — weekly headlines on Bitcoin, digital assets, business, and wellness, delivered every Sunday and Wednesday. Subscribe at ⁠www.stackedassets.co ⁠ Follow Us: YouTube: ⁠https://www.youtube.com/@stacked-assets⁠ Instagram: ⁠https://www.instagram.com/stackedassets/⁠ TikTok: ⁠https://www.tiktok.com/@stacked.assets⁠ Follow Emily Dempsey: Instagram: ⁠https://www.instagram.com/emilydempsey⁠ X: ⁠⁠https://x.com/EmilyDempsey⁠⁠ LinkedIn: ⁠https://www.linkedin.com/in/emily-j-dempsey/⁠ Follow The Brickell Babes: ⁠⁠⁠ Become A Member: ⁠www.thebrickellbabes.com⁠⁠/membership⁠ Instagram: ⁠https://www.instagram.com/thebrickellbabes/⁠ TikTok: ⁠⁠https://www.tiktok.com/thebrickellbabes/⁠⁠ KEY TOPICS COVERED — What being a fashion buyer actually teaches you about business: margins, distribution, markdowns, and managing profitability end to end — How The Brickell Babes went from a Facebook post to 70,000 members and a real company — and what building trust at scale actually requires — Why Bitcoin mining is really an energy and leverage business, and what Emily learned from 50+ site visits in under 12 months — Why nobody in this space has a formal degree and why that means you can start learning today — The thesis behind STACKED: knowledge compounds, wealth is built not found, and the body is part of the portfolio   TIMESTAMPS: 00:00:00 — Welcome to STACKED 00:00:44 — No jargon, no hype — here’s the format 00:01:25 — My dream of becoming a buyer for the biggest department stores in the world 00:02:04 — Getting an economics degree with a minor in business to appease my parents 00:02:36 — My first job out of college at Bergdorf Goodman 00:03:50 — The pandemic, 10 years in New York, and feeling the itch for something different 00:04:36 — How I started Brickell Babes as a Facebook group 00:05:04 — Fast forward: 70,000 women and over 600K monthly impressions 00:06:06 — Why there is no class, no degree, and no shortcut when it comes to Bitcoin 00:07:25 — Why mining is all about energy, leverage, and pricing economics 00:08:04 — Being on a plane every week — Texas, Ohio, Pennsylvania, and conferences 00:10:09 — Why I walked away from corporate to pursue entrepreneurship 00:11:37 — Why I only work with long-term aligned partners 00:12:44 — Hosting 200+ events, starting a book club, and giving back through Lotus House 00:14:13 — Why there were no resources out there for women like me 00:15:09 — Why mining is where money meets energy and infrastructure 00:17:00 — What I learned evaluating 100+ mining sites: on-grid vs off-grid 00:18:49 — My thesis: knowledge compounds and wealth is built, not found 00:20:39 — I don’t care if you buy Bitcoin — I care if you understand it 00:21:15 — The three pillars of STACKED DISCLAIMER This podcast is educational content, not financial advice. Do your own research; know your time horizon and risk tolerance.

    21 min
  6. From Bergdorf's to Bitcoin — Welcome to Stacked with Emily Dempsey

    TRAILER

    From Bergdorf's to Bitcoin — Welcome to Stacked with Emily Dempsey

    What does it take to build a life that's actually yours? Welcome to Stacked with Emily Dempsey — the podcast at the intersection of Bitcoin, wealth-building, entrepreneurship, and living well.Emily went from luxury fashion buyer at Bergdorf Goodman to Bitcoin miner, founder, and financial strategist. Now she's your filter — taking expert-level conversations on digital assets, business, and longevity and making them relevant to your real life.No jargon. No shilling. No fluff. Just clarity on money, power, and what's coming next.New episodes every week. Subscribe so you never miss a drop.This podcast is for educational purposes only and is not financial advice. Emily Dempsey is the host of STACKED — the podcast for the woman buying Botox and Bitcoin. She is the founder of The Brickell Babes, Miami's largest women's network with 70,000+ members, and one of the most active voices at the intersection of women, wealth, and the future of money. Connect with us: Subscribe to the STACKED newsletter — weekly headlines on Bitcoin, digital assets, business, and wellness, delivered every Sunday and Wednesday. Subscribe at www.stackedassets.co Follow Us: YouTube: https://www.youtube.com/@stacked-assets Instagram: https://www.instagram.com/stackedassets/ TikTok: https://www.tiktok.com/@stacked.assets Follow Emily Dempsey: Instagram: https://www.instagram.com/emilydempsey X: ⁠https://x.com/EmilyDempsey⁠ LinkedIn: https://www.linkedin.com/in/emily-j-dempsey/ Follow The Brickell Babes: ⁠ Become A Member: www.thebrickellbabes.com⁠⁠/membership Instagram: https://www.instagram.com/thebrickellbabes/ TikTok: ⁠https://www.tiktok.com/thebrickellbabes/⁠

    1 min

Trailer

Ratings & Reviews

5
out of 5
2 Ratings

About

Stacked with Emily Dempsey is the podcast at the intersection of Bitcoin, wealth-building, entrepreneurship, and living well. Emily went from Bergdorf Goodman fashion buyer to Bitcoin miner and founder — and now she's your filter. Expert-level conversations made actionable. No jargon, no shilling, no fluff. Just clarity on money, power, and what's coming next. New episodes weekly. Let's get stacked. For educational purposes only. Not financial advice.

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