Playbook by Michael morgenstern

$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.

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

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

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: [email protected] P: 413-847-6767 E: [email protected] 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

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: [email protected] P: 413-847-6767 E: [email protected] 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