The Operating System Show copertina

The Operating System Show

The Operating System Show

Di: Matt Dixon
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Everything your business knows walks out at 5pm. You rent it back every morning. And every time someone leaves, you lose a piece of how the place runs. That's the problem The Operating System Show exists to solve. I'm Matt Dixon, fractional CTO. I talk to the founders, COOs, and executives who are figuring out how to get their companies to run without every answer living in one person's head. Every week: what broke, what they rebuilt, and where the real leverage was. New episodes every week. Subscribe so you don't miss one.20206 Matt Dixon Economia Gestione e leadership Management
Episodi
  • Only 5% Have Mapped Their Real Process | Jordan Fleming on Redesigning Your Business for AI Agents

    Only 5% Have Mapped Their Real Process | Jordan Fleming on Redesigning Your Business for AI Agents
    Oct 22 2026
    Jordan Fleming bootstrapped smrtPhone from Poland, with the technical team in Romania, to just under 10 million dollars and nearly 60 people. Along the way it went from a phone system built for Podio to what he now calls an agentic conversation platform. He has since moved from CEO to chairman. His argument is that most companies spending on AI are not seeing growth from it. They drop very capable agents into processes designed around human limits, and those processes are full of invisible work that people quietly cover. Only about 5 percent of the companies he has worked with have mapped their processes the way the work actually runs. That is the subject of his book, The AI Workforce: redesign the business, one process at a time, around work shared between agents and people. ## In this episode - Four owners, distinct roles, and disagree and commit when they can't agree - Why they built in Eastern Europe, inside the EU legal and IP framework - The happy accident of building a phone system for Podio, and growing with almost no marketing - How every product update now flows into a company brain that updates help docs and agents - An agent that made 220,000 calls in three and a half weeks - Why AI spend is not turning into growth - The invisible work that never makes it onto the process map - Business structures built for one kind of labor, and what changes now - Hiring a role based AI agent and onboarding it to your company - Why voice agents built software first sound great in demos and fail in execution ## Timestamps 00:00 Welcome 01:01 Four owners, and stepping up to chairman 02:15 Splitting the roles so nobody deadlocks 03:43 Why build the company in Eastern Europe 05:18 From a PhD in music to Poland 06:08 Bootstrapping a phone system for Podio 08:09 From VoIP company to agentic conversation platform 08:45 How AI changed the way they build 09:40 220,000 calls in three and a half weeks 10:15 Why AI spend is not turning into growth 12:08 Only 5 percent map their real process 13:52 Redesigning process after process 14:42 The AI Workforce, his book 16:08 The four zones of AI 16:39 Business structures built for one kind of labor 18:47 The next 24 months 20:06 What broke as they scaled 22:05 Hiring role based AI agents 23:27 Onboarding an agent: property maintenance 25:01 Latency, and why telecom first matters 26:43 Who smrtPhone is for 28:14 Where to find Jordan and the book ## About Jordan Fleming Jordan Fleming is the cofounder and chairman of smrtPhone, an agentic conversation platform for voice and text, built for companies of 10 to 500 users. He is the author of The AI Workforce, a framework for redesigning a business around shared execution between AI agents and people. The AI Workforce, free executive briefing for listeners: https://thefutureworkforce.ai/p/os-show smrtPhone: https://smrtphone.io Listen: https://feeds.transistor.fm/the-operating-system-show Be a guest: https://crm.frontrangesystems.com/discovery
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    30 min
  • 300,000 Transactions, Under 50 People | Bryan Clayton on Building GreenPal to Run on Systems

    300,000 Transactions, Under 50 People | Bryan Clayton on Building GreenPal to Run on Systems
    Oct 20 2026
    Bryan Clayton started mowing yards in high school and grew it into a Tennessee landscaping company with about 150 people and 90 trucks. Fifteen years in, it was organized chaos every day, and he was the scaffolding holding it up. He never took a vacation longer than two days. After he sold it, he set out to build the opposite: a business with a system for almost every problem. That became GreenPal, a marketplace for lawn mowing that has handled about 300,000 transactions with fewer than 50 people, no offices, and no lawnmowers. We get into what he refused to repeat the second time, the difference between hard work and difficult work, how GreenPal keeps quality high with vendors it does not employ, and where he draws the line on what AI should never touch. ## In this episode - Why his first company was built as scaffolding around the founder - Every problem you solve unlocks five more, and why that is the job - Running a marketplace as a never ending series of experiments - From fragile to antifragile: weekly loops that make the business better on their own - Hard work versus difficult work, and the partner who wore 15 hour Sundays as a badge - What breaks in a remote first company, and why even Zoom has an office - The carrot and stick system that keeps independent lawn pros showing up - How AI gave a state school founder an MIT data scientist at the table - Why the founder should still do an hour of customer support every day - "Stop being lazy and ask Claude," and why AI makes everyone busier ## Timestamps 00:00 Intro 00:49 Under 50 people, 300,000 transactions 02:35 What he did differently the second time 05:45 Landscaping versus software 08:21 A never ending series of experiments 10:01 150 employees, 90 trucks, and a mechanic shop 11:44 From fragile to antifragile 14:19 Hard work versus difficult work 16:57 Running a remote first company 18:46 Quality from vendors you do not employ 21:53 How GreenPal uses AI 24:42 Who should not build a marketplace 26:25 The four zones of AI 27:59 Why the founder should do customer support 29:28 Messy data and "stop being lazy and ask Claude" 32:16 Why AI makes everyone busier 33:26 What is next: a million users 34:11 Where to find Bryan ## About Bryan Clayton Bryan Clayton is the cofounder and CEO of GreenPal, a marketplace that connects homeowners with local lawn care pros. Before GreenPal he built and sold a landscaping company in Tennessee. GreenPal: https://www.yourgreenpal.com/ Listen: https://feeds.transistor.fm/the-operating-system-show Be a guest: https://crm.frontrangesystems.com/discovery
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    35 min
  • Fix the Data Before the AI | Jay Bourgana on Buying the Business in the Owner's Head

    Fix the Data Before the AI | Jay Bourgana on Buying the Business in the Owner's Head
    Oct 13 2026
    Jay Bourgana took a real estate brokerage from zero to 350 million dollars in sales volume in four years, then sold 70 percent of it to a much larger firm in 2018. Since then he has been on both sides of about 30 acquisitions, buying plumbing, HVAC, and IT companies. Today he runs Foresight Partners. His favorite deals are what he calls flywheel businesses: no website, no marketing, customers who keep calling anyway, strong margins, and a founder who carries the whole operation in his head. Before he even signs a letter of intent, he starts pulling that knowledge out. His warning for owners racing toward AI: fix the data first. Most companies run on duplicate records, spreadsheets stitched together by hand, and reports that arrive a month late. Put AI on top of that and it just moves faster in the wrong direction. ## In this episode - How a manufacturing mindset built a brokerage that answered new leads in seconds - The cold email he almost deleted, and selling 70 percent of his company 30 days later - Why he buys businesses that only work because the founder is inside them - The three engines he maps before closing: clients, talent, and capital - Why owners grow to five million, hate it, and shrink back to three - People, then process, then technology, and why speeding up the machine shakes everything loose - Data before AI: closed loop companies and the cost of lagging numbers - Why middle managers become the human in the loop for AI agents - Who should sell to him, and who should not - Kids Business School, teaching entrepreneurship to kids 7 to 17 ## Timestamps 00:00 Zero to 350 million in four years 00:52 Bringing manufacturing thinking to real estate 03:22 How owners can use data better 06:41 Speed to lead, then and now 09:11 The cold email that sold the company 10:43 Retiring, then getting back in 12:02 What he does first when he buys a business 14:02 When everything lives in the owner's head 16:11 Buying to own forever 17:12 Why owners shrink back to three million 20:00 People, process, technology, and the shake 21:01 How he uses AI and why data comes first 23:07 The four zones of AI 24:53 Why middle managers become the human in the loop 28:13 75 states in a 50 state CRM 31:46 If you need Excel, something is wrong 32:35 The company that could not tell him its churn 34:06 Who should sell to him, and who should not 37:50 What is next, and Kids Business School 39:39 Where to find Jay ## About Jay Bourgana Jay Bourgana is the founder of Foresight Partners, which buys and operates founder led home services and professional services businesses. He built and sold a real estate brokerage, has been on both sides of about 30 acquisitions, and is building Kids Business School, an entrepreneurship program for kids 7 to 17. Acquisitions Collective: https://acquisitionscollective.biz/ Kids Business School: https://kidsbusinessschool.com/ Listen: https://feeds.transistor.fm/the-operating-system-show Be a guest: https://crm.frontrangesystems.com/discovery
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    40 min
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