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: [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