Playbook by Michael morgenstern

About Playbook by Michael morgenstern

The Playbook Podcast is concentrated operational truth. Founders, VCs, operators, and capital allocators who've actually scaled things — talking about what worked, what broke, and what they'd never do again. No panel-speak, no thought leadership theater. Just the tactical lessons, hard-won frameworks, and real math behind building companies and deploying capital. They happen to be in Miami. The signal is universal.

Publisher

Michael Morgenstern

Category

business

Language

en

Explicit

No

First episode

22 Feb 2026

Latest episode

12 Oct 2026

Latest episodes

11 episodes in the feed.

1. 

   12 Oct 2026

   Is Brick-and-Mortar Dead? Why Retail Is Thriving Again | Amish Tolia

   Is brick-and-mortar retail really dead? According to Amish Tolia, Co-Founder and CEO of Leap, the answer is a definitive no. In this episode, Amish shares how Leap is helping modern brands launch and scale physical retail stores while creating profitable omnichannel growth strategies. We discuss the future of retail, why Gen Z and Gen Alpha are driving a return to in-store experiences, how brands can combine e-commerce with physical locations, and why malls and storefronts are seeing renewed demand. If you're interested in retail trends, entrepreneurship, e-commerce, Shopify, omnichannel commerce, and brand growth, this conversation is packed with valuable insights. CHAPTERS: 0:00 Introduction to Leap 0:45 Building the Shopify for Retail 1:30 Why Brands Need Physical Stores 2:15 Creating Strong Brand Experiences 3:00 The State of Modern Retail 3:45 Challenges of E-Commerce Growth 4:30 Why Gen Z Loves In-Store Shopping 5:15 Retail Trends and Market Opportunities 6:00 Brands Growing With Leap 6:45 How Leap Selects Partners 7:30 The Future of Omnichannel Commerce 8:00 Is Brick-and-Mortar Really Dead? 8:16 Final Thoughts Playbook is shot, edited, produced, and published by Short Form Media http://shortformmedia.co CONNECT WITH AMISH TOLIA: Website:https://www.leapinc.com/ Instagram:@leapretail Linkedin:https://www.linkedin.com/company/leapretail (https://www.linkedin.com/company/leapretail/posts/?feedView=all) CONNECT WITH PLAYBOOK BY MICHAEL MORGENSTERN: Instagram: @michaeljmorgenstern Apple Podcast: https://podcasts.apple.com/us/podcast/playbook-by-michael-morgenstern/id1879332626 Essential listening for founders, operators, and anyone building in the AI era. 🔔 Subscribe for weekly conversations with the world's top founders and operators. Playbook is proudly working with Airwallex — the global financial and banking platform built for ambitious businesses. Learn more at airwallex.com

2. 

   5 Oct 2026

   Why AI Commerce Is Replacing Static Websites | Rishabh Jain, FERMÀT

   In this episode, Rishabh Jain, Co-Founder and CEO of FERMÀT, shares how AI is transforming the way consumers interact with brands online. From personalized shopping experiences to intelligent digital interfaces, Rishabh explains why the future of e-commerce will look dramatically different from today's static websites. We discuss AI-powered commerce, customer behavior analysis, website personalization, digital experiences, online retail innovation, and how leading brands are preparing for the next wave of consumer expectations. If you're interested in e-commerce, AI, retail technology, customer experience, and the future of online shopping, this conversation is for you. CHAPTERS: 0:00 Introduction to Rishabh Jain 0:40 The Origin of FERMÀT 1:20 Solving Customer Experience Challenges 2:00 The Future of Commerce 2:45 Why Websites Must Become Dynamic 3:30 AI and Consumer Expectations 4:15 Understanding Customer Behavior 5:00 Creating Personalized Shopping Experiences 5:45 Predictions for the Next 3 Years 6:30 AI Adoption Challenges for Businesses 7:20 Customer Success Stories 8:05 The Vision for FERMÀT 8:52 Final Thoughts Playbook is shot, edited, produced, and published by Short Form Media http://shortformmedia.co CONNECT WITH RISHAB JAIN: Website: rishabh@fermatcommerce.com X:  https://x.com/rishabhmjain & https://x.com/fermatcommerce Linkedin:https://www.linkedin.com/in/rishabhmjain/ & https://www.linkedin.com/company/fermat-commerce/ CONNECT WITH PLAYBOOK BY MICHAEL MORGENSTERN: Instagram: @michaeljmorgenstern Apple Podcast: https://podcasts.apple.com/us/podcast/playbook-by-michael-morgenstern/id1879332626 Essential listening for founders, operators, and anyone building in the AI era. 🔔 Subscribe for weekly conversations with the world's top founders and operators. Playbook is proudly working with Airwallex — the global financial and banking platform built for ambitious businesses. Learn more at airwallex.com

3. 

   30 Sept 2026

   Building a Global Brand with Only 10 People | Rahul Gandhi, Crossterra

   In this episode, Michael Morgenstern sits down with Rahul Gandhi, the founder and CEO of Cross Terra, live from the Commerce Capital Summit on a rooftop in Manhattan. Rahul breaks down how his company built an innovative operating system designed to help e-commerce brands seamlessly expand into notoriously complex international regions like China, India, Latin America, and the Middle East. Historically left to massive corporations with endless capital, Cross Terra has completely flipped the script, enabling mid-sized brands to establish turnkey global operations with minimal investment and zero operational headaches. Throughout the conversation, Rahul discusses the changing dynamics of global supply chains, rising tariff costs, and the power of leveraging local marketplaces like Tmall and JD. He also shares fascinating insights into how his small team of ten relies heavily on AI tools and localized operations to simplify logistics using a known dropship approach. Whether you are a brand executive, CFO, or e-commerce strategist looking for untapped growth channels outside of standard ad networks, this episode provides a masterclass on scaling international retail. CHAPTERS: 0:00 Introduction to the Commerce Capital Summit 0:42 Meet Rahul Gandhi of Cross Terra 1:27 Scaling E-Commerce into Complex Regions 2:11 Why Brands Struggle with International Expansion 3:14 Testing Global Markets with Low Capital 4:12 Scaling into China, India, and Latin America 5:10 Playbook for Navigating International Logistics 6:03 Building a Small Team Powered by AI 7:19 Target Personas for E-Commerce Growth 8:20 Simplifying Supply Chain and Dropshipping Logistics 8:57 Entrepreneur Life and Family Playbook is shot, edited, produced, and published by Short Form Media http://shortformmedia.co CONNECT WITH RAHUL GANDHI: X: x.com/crossterrainc Linkedin: linkedin.com/company/110744347 CONNECT WITH PLAYBOOK BY MICHAEL MORGENSTERN: Instagram: @michaeljmorgenstern Apple Podcast: https://podcasts.apple.com/us/podcast/playbook-by-michael-morgenstern/id1879332626 Essential listening for founders, operators, and anyone building in the AI era. 🔔 Subscribe for weekly conversations with the world's top founders and operators.

4. 

   25 Aug 2026

   Why LinkedIn Failed at Transactions (And What Comes Next) with Chris Quinn

   In this episode of the podcast live from the Commerce Capital Summit, we sit down with Chris Quinn, the founder of Super Connector. Chris breaks down why your network is your true net worth and how his platform is pioneering the new network economy by building a literal "wallet for your network". If you are looking to monetize your connections or find a brand-new, high-converting B2B sales channel that relies on human trust rather than cold outreach, this conversation covers exactly how the platform works for both businesses and everyday connectors. We dive deep into how Chris transitioned from venture capital to launching Super Connector, how AI and automated matching via CLI are scaling warm introductions, and why traditional platforms like LinkedIn are falling short when it comes to true business transactions. Whether you are a founder, sales professional, investor, or someone looking to make a serious passive income stream through introductions, tune in to discover the future of the human data marketplace. CHAPTERS: 0:00 Introduction to Chris Quinn 0:23 What is Super Connector? 1:07 Who Can Become a Connector? 2:34 The Light Bulb Moment 3:52 Building the Network Wallet 4:50 Onboarding Businesses and CRM Integration 6:53 The Next 12 Months for Super Connector 8:02 Utilizing AI and CLI for Introductions 9:45 Turning Humans into Salespeople 11:02 How to Find Super Connector 11:25 Why LinkedIn Failed at Transactions 12:47 The Power of Proving Network Density Playbook is shot, edited, produced, and published by Short Form Media http://shortformmedia.co CONNECT WITH CHRIS QUINN: X:  x.com/Superconnector Linkedin:linkedin.com/company/superconnectorinc CONNECT WITH PLAYBOOK BY MICHAEL MORGENSTERN: Instagram: @michaeljmorgenstern Apple Podcast: https://podcasts.apple.com/us/podcast/playbook-by-michael-morgenstern/id1879332626 Essential listening for founders, operators, and anyone building in the AI era. 🔔 Subscribe for weekly conversations with the world's top founders and operators.

5. 

   6 Jul 2026

   The Future of Commerce: Chelsea Zhang's Investment Playbook

   Chelsea Zhang leads commerce investing at Equal Ventures and runs the Commerce Capital Summit — which means she sees nearly every AI commerce pitch in the market and every incumbent's counter-move. That vantage point makes her one of the sharpest voices on what's real and what's noise in commerce right now. In this episode, Chelsea and Michael Morgenstern get into the agentic commerce debate — who actually captures value when an AI agent does the checkout — why founder-market fit still beats a hot sector, how brand building changes when every company has infinite creative leverage, and why relationships remain the last durable edge in venture. Chelsea also breaks down the Equal Ventures thesis, the sectors she's watching in 2026, and her most recent portfolio bets across retail, supply chain, and commerce infrastructure. If you build, invest in, or operate anything that touches commerce, this one earns the full watch. CHAPTERS: 0:00 Who Is Chelsea Zhang 0:50 Inside the Commerce Capital Summit 1:40 How AI Is Actually Changing Commerce 2:30 Brand Building When Everyone Has AI 3:20 The Equal Ventures Thesis 4:10 What Gets a Term Sheet in 2026 5:00 Founder-Market Fit, Defined 5:50 Where Venture Is Heading 6:40 The Sectors Worth Watching 7:30 Agentic Commerce: Hype vs. Reality 8:20 What AI Commerce Looks Like in Five Years 9:10 How Chelsea Picks Her Bets 10:00 Equal Ventures' Latest Investments Playbook is shot, edited, produced, and published by Short Form Media — http://shortformmedia.co CONNECT WITH CHELSEA ZHANG: X: @zchelseaz LinkedIn: https://www.linkedin.com/in/zhangchelsea/ CONNECT WITH PLAYBOOK BY MICHAEL MORGENSTERN: Instagram: @michaeljmorgenstern Apple Podcasts: https://podcasts.apple.com/us/podcast/playbook-by-michael-morgenstern/id1879332626 Essential listening for founders, operators, and anyone building in the AI era. Subscribe for weekly conversations with the world's top founders and operators.

6. 

   30 Jun 2026

   The Untapped Market in Women's Fitness & Nutrition with Nina Khoury

   Nina Khoury joins the Playbook Podcast to discuss her journey from representing Australia in field hockey to consulting at Bain, helping scale SKIMS, and now building Sportiv, a supplement brand designed specifically for women who train. In this episode, we dive into women's fitness, strength training, supplements, protein, recovery, healthy aging, entrepreneurship, and why the wellness industry continues to overlook female consumers. Nina shares her insights on building a large consumer brands, the future of women's nutrition, and the biggest fitness mistakes women make today. CHAPTERS: 0:00 Introduction to Nina Khoury 0:48 Transitioning from Athlete to Founder 1:38 Spotting the Gap in Women's Supplements 2:21 The Growth of Women's Strength Training 3:50 Why the Wellness Market Overlooks Women 4:44 Debunking Fitness Industry Myths 5:36 What is Sportiv Labs? 6:46 Launching a Consumer Brand in Public 7:10 The Biggest Mistake Women Make in Fitness Playbook is shot, edited, produced, and published by Short Form Media http://shortformmedia.co CONNECT WITH NINA KHOURY: Instagram: @ninackhoury (https://www.instagram.com/ninackhoury/) & @sportivlabs (https://www.instagram.com/sportivlabs/) Linkedin: https://www.linkedin.com/in/ninakhoury CONNECT WITH PLAYBOOK BY MICHAEL MORGENSTERN: Instagram: @michaeljmorgenstern Apple Podcast: https://podcasts.apple.com/us/podcast/playbook-by-michael-morgenstern/id1879332626 Essential listening for founders, operators, and anyone building in the AI era. 🔔 Subscribe for weekly conversations with the world's top founders and operators.

7. 

   20 May 2026

   David Blumberg: Backing $48 Trillion in AI, Israel's Rise, and the Miami Tech Revolution

   $48 trillion. That's the AI market David Blumberg has been quietly positioning for, since before most people knew it existed. David Blumberg is the founder and managing partner of Blumberg Capital, one of the most enduring early-stage venture firms in the world. Since founding the firm in 1991, he's backed companies from seed to IPO across North America, Israel, and Europe including first checks into Braze, DoubleVerify, HootSuite, and Nutanix. A Harvard and Stanford GSB alum who cut his teeth at T. Rowe Price, the Bronfman family office, and Check Point Software, David has seen every cycle the tech industry has thrown at investors. Now he's in Miami, doubling down on agentic AI. This conversation goes deep on how David evaluates founders, why he believes agentic AI represents a $48 trillion market cap opportunity, and why the best time to be alive is right now. Playbook is shot, edited, produced, and published by Short Form Media http://shortformmedia.co CONNECT WITH DAVID BLUMBERG: Instagram: @blumbergcapital Website: blumbergcapital.com LinkedIn: https://www.linkedin.com/in/davidjblumberg CONNECT WITH PLAYBOOK BY MICHAEL MORGENSTERN: Instagram: @michaeljmorgenstern Apple Podcast: https://podcasts.apple.com/us/podcast/playbook-by-michael-morgenstern/id1879332626 Essential listening for founders, operators, and anyone building in the AI era. 🔔 Subscribe for weekly conversations with the world's top founders and operators.

8. 

   4 May 2026

   From Bootstrapped to Acquired - How a Miami Founder Built and Sold a Multi-Million Startup

   What does it actually take to build a company from zero with your own money and sell it to a global brand? In this episode of Playbook, Michael sits down with Adam Garfield, Miami-born founder of SpeedyTab, a mobile ordering platform he bootstrapped from a bar idea in Boston all the way to an acquisition by Wix in 2021. Adam then served as VP of Restaurants at Wix, overseeing product, engineering, and go-to-market across nearly 200 countries. They cover the real story behind founder-led sales, channel partnerships, pivoting under pressure, competing against VC-backed giants with no outside capital, and what it means to build in Miami when Miami wasn't on anyone's startup map. Plus, Adam shares where he's headed next and why he thinks nonprofits are the next big vertical AI opportunity. If you're a founder, operator, or builder, this one is for you. Special thanks to our sponsors at Airwallex — the all-in-one global payments platform built for fast-growing businesses. Whether you're paying international contractors, managing multi-currency accounts, or scaling across borders, Airwallex makes it seamless. Follow them: https://www.instagram.com/airwallex/ Learn more: https://www.airwallex.com Playbook is shot, edited, produced, and published by Short Form Media 🔗 http://shortformmedia.co CHAPTERS: 00:00 — Building a startup with your life savings 01:27 — Who is Adam Garfield? Miami-born, UF-raised 05:11 — The pivot from bars to coffee and food 09:18 — Landing Panther Coffee as the first customer 12:21 — Becoming the Shopify for restaurants 18:06 — Channel sales with Toast, Square & more 22:57 — How Covid catapulted SpeedyTab's growth 26:28 — Getting acquired by Wix: what nobody tells you 33:12 — Why 2026 is Miami's moment 40:05 — Rapid fire: frameworks, drones & advice to founders

9. 

   30 Mar 2026

   Peter Yared on Building InCountry, Enterprise AI, and Why Miami is the Next Tech Hub

   Seven exits. Fortune 500 CTO. Now building the infrastructure for AI in a deglobalizing world. Peter Yared sits down with Michael Morgenstern to unpack 25 years of hard-won lessons from the trenches of enterprise tech, from the early days of the internet to the AI era reshaping everything. Peter sold companies to Oracle, Sun Microsystems, and Citrix. He ran technology at CBS Interactive, deciding where billions in tech spend went. He grew up internationally across Switzerland, Austria, and the UK, learning early that the world doesn't play by one set of rules. Now he's the founder and CEO of InCountry, solving data residency and compliance for multinationals operating in 90+ countries, and just launched Agent Cloak to bring zero trust architecture to cross border AI agents. This conversation goes deep on what actually works when selling to the enterprise, why piggybacking on existing platforms beats going direct, and the counterintuitive reality that building something hard for Fortune 500s from day one can be easier than iterating your way up from startups. What you'll learn: Why enterprise buyers hate new vendors and how to bypass procurement hell The deglobalization thesis that seemed crazy in 2017 and is obvious now How Agent Cloak is bringing zero trust and data minimization to AI agents Why Miami should target European, Israeli, and Latin American entrepreneurs The build in public trap that's killing founder credibility in the attention economy Why shipping absolute crap to iterate is now a death sentence for startups Peter also breaks down why Miami doesn't need a Stanford, how the city is becoming the Dubai of the Western Hemisphere, and why the next decade belongs to second and third time founders relocating to South Florida. Plus: the brutal truth about why most AI pilots at enterprises are failing, what 80s style management is making a comeback, and the one piece of advice he'd give his 25 year old self. Peter Yared on LinkedIn: https://linkedin.com/in/peteryared AgentCloak:https://incountry.com/products/agentcloak Thank you to our sponsors Special thanks to our sponsors at Newmark — the go-to commercial real estate team for fast growing founders. Matt Himmelsbach: https://www.nmrk.com/people/matt-himmelsbach Brandon Shores: https://www.nmrk.com/people/brandon-shores Playbook is shot, edited, produced, and published by Short Form Media 🔗 http://shortformmedia.co Chapters 00:00:00 Introduction: Peter Yared's Journey from Vienna to Silicon Valley 00:04:45 From Seller to Buyer: Lessons as CTO at CBS Interactive 00:09:00 Building InCountry: Solving Data Residency for Global Enterprises 00:12:01 Agent Cloak: Privacy and Data Minimization for Enterprise AI 00:14:25 Enterprise Go-to-Market: The Power of Platform Piggybacking 00:16:27 The AI Landscape: Vertical AI vs Horizontal Models 00:17:07 Customer Service Agents: The First Wave of Enterprise AI Deployment 00:20:59 Miami as a Tech Hub: Comparing the Journey to New York 00:26:35 Attracting Entrepreneurs: Europe, Israel, and Latin America 00:30:29 The Talent Question: Remote Work, AI Coding, and Management Philosophy 00:42:06 Building in Stealth: Why Not Everything Should Be Built in Public 00:40:07 Mental Models and Hard Decisions: Don't Be Reactive 00:44:56 VC Funding Reality: Overfunding and Talent Diffusion 00:48:02 Advice to Young Peter: Risk, Reward, and the Journey Essential listening for founders, operators, and anyone building in the AI era. 🔔 Subscribe for weekly conversations with the world's top founders and operators. #PeterYerid #InCountry #AgentCloak #DataResidency #EnterpriseAI #Miami #MiamiTech #Playbook #FounderMindset #AIRevolution #Entrepreneurship #ZeroTrust

10. 

    12 Mar 2026

    He Sent 526 Investor Emails Before Getting a YES - Now He Has Raised $60M

    Build the business investors chase, not the other way around. Matthew Vega-Sans, co-founder of Gail AI, sits down with Michael Morgenstern to break down how a kid from a Kendall farm dropped out of college, got rejected 526 times, hit rock bottom at $2,800 in the bank, and then raised $60M by doing one thing differently. Filmed inside Gail's brand new offices in Miami, Matthew shares the raw truth about building a hyper-intelligent AI company in financial services, why Miami is the most underrated city in tech, and the counterintuitive fundraising strategy that had 130 VC firms knocking on his door organically. What you'll learn: Why building a business that does not need investors is the #1 fundraising hack How Gail AI is cutting frontline labor costs from $30/hr to under $6/hr The compliance traps that kill AI companies in regulated industries Why Miami's talent pool is a massive arbitrage opportunity The culture as a product framework that is building Gail's team Whether you're a founder, operator, or just fascinated by the future of AI in finance, this one is for you. 🔗 Learn more about Gail meetgail.com 📍 Filmed at Gail AI Headquarters, Miami Episode 2 is live Thank you to our sponsors https://www.nmrk.com/people/matt-himmelsbach E: matt.himmelsbach@nmrk.com P: 413-847-6767 E: brandon.shores@nmrk.com P: 305-350-0926 Playbook is shot, edited, produced, and published by Short Form Media 🔗 http://shortformmedia.co Chapters 00:00:00 Introduction and Matthew's Journey from Kendall Farm to AI 00:03:12 Building Gale: Hyper-Intelligent AI for Financial Services 00:05:52 Solving Real Problems: Customer Pain Points and Market Opportunity 00:12:08 Culture as a Product: Building Gale's Team 00:15:37 Why Miami: Increasing Collective Ambition 00:20:57 The Talent Monopoly: Miami's Hidden Advantage 00:26:24 Fundraising Lessons: Build a Business That Doesn't Need Investors 00:30:44 The Big Hairy Audacious Goal: Financial Services Across the Solar System Essential listening for founders, operators, and anyone building in the AI era. 🔔 Subscribe for weekly conversations with the world's top founders and operators. #MatthewVegaSanz #Gale #AI #FinancialServices #Miami #Entrepreneurship #StartupLife #Fundraising #MiamiTech #Playbook #FounderMindset #AIRevolution

11. 

    22 Feb 2026

    Why Miami Beats Silicon Valley: Fred Voccola on Scaling 2,500 Employees in South Florida

    In 2014, Fred Voccola told investors he was building a multi-billion dollar software company in Miami. They said his employees would stare out the window and party all day. Today Kaseya has 2,000+ employees in the city. $1.5B ARR. $15B valuation. Over 150 marriages between staff. Liquid millionaires—not paper, liquid—running to Fred’s office crying because they just bought their parents their first house. Brought their abuela over from Cuba. Now Fred just relocated Simpro Group—Australia’s most valuable native software company—to Miami as North American HQ. Chairman & CEO. $300M+ revenue. 450,000 users. Targeting $1B ARR. Hiring several hundred in South Florida in 18 months. His former COO? Now CEO of WatchGuard. Moving it to Miami. His former CPO? CEO of UpShop. Same building as Fred. Miami. This is The Playbook—18 episodes extracting the operational frameworks behind outcomes like these. No panels. No thought leadership theater. Just the math of how the machine actually runs. We’re starting with Fred because the pattern is the point: find an industry running at 7-11% margins, collapse the cost structure, and change the unit economics of an entire workforce’s life. He did it for MSPs at Kaseya. He’s doing it now for the $150B global trades economy—plumbers, electricians, field crews—through AI-first infrastructure. His talent thesis doubles as a city thesis: labor costs 50% below NYC/SF. An immigrant workforce that tolerates risk and pivots every four hours. Five hungry FIU grads over an Oracle VP riding a wave. A city where people actually have dinner together across political lines. Fred built the proof before anyone believed the thesis. Now the thesis is obvious. Episode 1 is live. Thank you to our sponsors https://www.nmrk.com/people/matt-himmelsbach E: matt.himmelsbach@nmrk.com P: 413-847-6767 E: brandon.shores@nmrk.com P: 305-350-0926 Playbook is shot, edited, produced, and published by Short Form Media 🔗 http://shortformmedia.co Chapters 00:00:00 Introduction and Fred's Journey to Miami 00:08:10 Finding Big Problems to Solve 00:16:34 Building Kaseya: Transforming the MSP Industry 00:30:50 Building in Miami: Proving the Skeptics Wrong 00:38:54 SimPro: The Next Big Opportunity 00:45:12 AI and The Coming Destruction 00:53:24 Miami's Future and Rapid Fire Essential listening for founders, operators, and anyone building in the AI era. 🔔 Subscribe for weekly conversations with the world's top founders and operators. #FredVoccola #Kaseya #SimPro #Entrepreneurship #Miami #AIRevolution #SerialEntrepreneur #SaaS #MiamiTech #Playbook #FounderMindset #BillionDollarCompany

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Spotify

5.0 / 5

4 ratings

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