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

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.

011. She Manifested A Martha Stewart Collab — And Just Renewed It. How a Second Date Idea Became a Multi-City Empire | | Elisa Marshall, Maman

Welcome back to STACKED — the show about becoming your own best asset. Today I sat down with Elisa Marshall, co-founder and Chief Brand Officer of Maman, the French-inspired café and lifestyle brand she built with her husband Benjamin Sormonte from a 1,600 sq ft SoHo grab-and-go in 2014 into 54 locations across the US and Canada, a Martha Stewart collaboration, and one of the most imitated brand aesthetics in hospitality. Elisa came up through luxury fashion buying, retail leasing, wedding planning, catering, and baking — five jobs, none of them enough. Maman was the room she built to do all of it under one roof. In this episode she breaks down how she built a hero product before social media existed, what makes a celebrity partnership actually work, the commissary model behind scaling 54 locations economically, and the line she will never cross on in-person hospitality. Key Topics Covered * Multi-passion origin story: fashion, events, weddings, baking, and the job that did not exist * The first Maman in SoHo: 18 seats, grab-and-go that became sit-and-stay * The cookie that put Maman on the map and the man who drove an hour to buy one * Pre-Instagram virality: how a Grub Street article triggered a 24-hour bake shift * From 50 cookies a day to 100 dozen at peak demand * Why Elisa builds every location like it is the only one * The four signature brand prints and the personal stories behind each * The vintage china obsession and why customers steal it * The Martha Stewart partnership: how it came together and how it just got renewed * What makes a celebrity collab work — and what kills most of them * The commissary model: one central kitchen, 8 to 10 satellite locations * Events as 20% of revenue and why dinner service did not pencil * Site selection: second-generation spaces with charm built in * Why Maman will never put a self-order screen in any location * What Elisa would do with $50K in 30 days starting over today * Building a legacy brand for the next generation Timestamps:  00:00 Welcome to STACKED  00:30 Introducing Elisa Marshall and Maman  02:00 Growing up between Toronto and Montreal  02:30 The five jobs era: fashion, events, weddings, catering, baking  04:00 Two entrepreneurial parents and the lesson that stuck 07:00 The first Maman: 1,600 sq ft in SoHo, 2014  10:00 Why reservations did not work in New York  12:00 The first signal: the man who drove an hour for cookies  13:30 The Grub Street article they did not know about  15:00 Fifty cookies a day to 100 dozen at peak  26:00 Maman today: 54 locations across the US and Canada  29:00 Events as a 20% revenue stream 34:00 Aesthetics as the moat: the feeling, not just the food  37:00 The four signature prints and the stories behind them  40:00 Why customers steal the china and what Elisa is building because of it  46:30 Manifesting Martha Stewart since age nine 48:00 How the Martha Stewart partnership came together  51:00 What makes a celebrity collaboration actually work  1:00:30 The hardest part of scaling hospitality  1:05:00 Why Maman will never install a self-order screen  1:07:30 Starting over with $50K in 30 days  1:10:00 Building a legacy business for her kids  Tags: Elisa Marshall, Maman NYC, French café, lifestyle brand, hospitality scaling, brand building, Martha Stewart collab, café business, restaurant unit economics, commissary model, hero product, women founders, female entrepreneur podcast, café aesthetics, brand strategy, STACKED podcast, Emily Dempsey, Brickell Babes, scaling a small business, second generation real estate 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.

010. Bitcoin 101: He Built The First Laptop. Now He's Securing Bitcoin. | Bob Burnett former CTO of Gateway Computers On Bitcoin Mining, Heat Reuse, and Why Crypto Pulled Him Out of Retirement

Welcome back to STACKED — the show about becoming your own best asset. Today, I sat down with Bob Burnett. Bob spent over 35 years at the intersection of technology and infrastructure — on the engineering team behind the world’s first laptop, and as CTO of Gateway Computers, one of the most iconic Fortune 200 companies of the era. In 2017 a single phone call brought him into crypto mining and one year of deep research led out of retirement and all-in on Bitcoin. Today,  Bob is the founder and CEO of Barefoot Mining and board member at Ocean – a Bitcoin mining pool backed by Jack Dorsey, the co-founder of Twitter, among other ventures. Barefoot Mining is one of the most innovative off-grid Bitcoin mining operations in the world. This episode is your introductory course on Bitcoin mining: why do people mine Bitcoin in the first place, how does it work, and why energy costs matter more than money in today’s world.  Key Topics Covered * From Wisconsin to the world’s first laptop * How the personal computer, the internet, Bitcoin, and AI are not four separate things * Metcalfe’s Law, network effects, and what happens when networks start multiplying each other * The Bitcoin adoption S-curve * Why Ethereum lost its soul when it abandoned proof of work * Why Bitcoin consumes only 0.6% of the world’s electricity and why most of it is wasted energy * Cow manure, hydroelectric, solar, and stranded gas * On-grid vs. off-grid mining * The future of block space — why nation states and big banks will eventually mine * Ocean and why template creation is the only mining that is true to Bitcoin’s principles Timestamps 00:00 — Welcome to STACKED 00:30 — Introducing Bob Burnett and Barefoot Mining 01:30 — The Stacked play on words: stacking sats 02:00 — Why Emily made an exception for a virtual inter in view 03:20 — Growing up in Kenosha, Wisconsin and the Apollo missions 05:00 — The birth of the personal computer 06:55 — The world’s first laptop and being there when something big was happening 09:00 — Metcalfe’s Law: the power of a network is the square of its users 10:50 — The four steps: personal computer, internet, Bitcoin, AI 11:30 — AI, agentic workflows, and the decentralization of intelligence 13:50 — Metcalfe’s Law of Metcalfe’s Law 22:00 — How the rate of change is becoming astronomical 24:00 — The technology adoption S-curve 38:00 — Where Bitcoin sits on the adoption curve today 44:30 — What was Bob’s first signal on Bitcoin? 48:00 — The 2017 phone call that changed everything 54:50 — The switch from Ethereum to Bitcoin 58:00 — What Bitcoin actually has that Ethereum never did 01:06:10 — The biggest misconception about Bitcoin mining 01:11:10 — Is Bitcoin mining bad for the environment? No. 01:13:30 — Cow manure to Bitcoin: the Indiana dairy farm 01:16:40 — Bitcoin mining explained in 60 seconds 01:29:50 — The orchard produces oranges. Bob produces blocks. 01:33:10 — Final settlement in 10 minutes and what that means for global commerce 01:40:40 — The future: nation states, big banks, and the fade of public miners 01:41:20 — On-grid vs. off-grid 01:49:50 — Lightning round 01:57:00 — Wrap up and where to find Bob Tags Bob Burnett, Barefoot Mining, Ocean mining pool, Bitcoin mining, Bitcoin infrastructure, proof of work, block space, Bitcoin energy, off-grid mining, on-grid mining, Bitcoin adoption curve, Ethereum vs Bitcoin, Gateway CTO, Bitcoin decentralization, Metcalfe’s Law, digital asset investing, STACKED podcast, Emily Dempsey, Brickell Babes, Bitcoin sovereignty, Bitcoin mining explained 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.