Episodes

  • How to Send Texts Your Customers Will Reply To: Conversation Design 101

    How to Send Texts Your Customers Will Reply To: Conversation Design 101
    Oct 15 2026

    This week, it's a solo episode. Mav Head of Brand and Conversation Design Hillary Black takes the mic to share what eight years of writing for bots has taught her about one thing: getting people to actually text you back.


    On the table: what a conversation designer really does, why ChatGPT made your customers harder to impress, the texting mistake she sees brands make constantly, and her top three fixes you can use today, no matter which AI you run.


    Chapters

    00:00 — Intro

    00:15 — A solo episode

    01:21 — What is conversation design?

    02:05 — Why the good bots are good

    02:43 — From writing bot scripts to writing system prompts

    03:48 — Why conversation design matters more than ever

    05:40 — When AI support chat goes off the rails

    06:46 — If you're texting your leads

    08:02 — Top three ways to improve your conversations

    08:31 — Tip 1: Make it a two-way conversation

    09:56 — Tip 2: Ask one thing per message

    11:24 — Tell people how to respond

    12:22 — Close the loop

    13:23 — Tip 3: Test it yourself as a user

    14:57 — What to look for in your conversation logs

    16:07 — Close


    Host

    Hillary Black — Head of Brand and Conversation Design, Mav


    Links and Resources

    ChatGPT, OpenAI's assistant and the reason your customers expect more from every chat

    Claude, Anthropic's assistant, home of the Opus and Sonnet models Hillary mentions

    SmarterChild, the AIM chatbot that couldn't answer much of anything


    Follow the show

    Manual Work is a Bug is Mav's podcast, now on video. Watch on YouTube and follow wherever you listen, so you don't wait another six years for the next episode. Mav helps insurance agencies grow their book with AI: hiremav.com.


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    Amazon Music

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    17 mins
  • How Insurance Agencies Are Using AI, Live From ITC Vegas 2026

    How Insurance Agencies Are Using AI, Live From ITC Vegas 2026
    Oct 8 2026

    This week we have a special episode - Live from the ITC 2026 expo floor. Mav Founder + CEO Matthew Black and Head of Brand Hillary Black grab ten minutes in the official podcast studio between booth shifts to report on what actually changed in insurance this year.


    Every vendor is still pitching their version of AI for insurance. But what’s changed this year is the agency owners.


    On the table: why GPT helped the first five minutes of every sales conversation finally disappear for companies in AI, the commercial agency strategy for quickly moving into personal lines without hiring, evidence that Mav has the coolest booth in the tradeshow circuit, and Matthew's prediction for where the insurance product itself is headed in the next year.


    Chapters

    00:00 — Intro

    00:16 — Live from the ITC 2026 expo floor

    01:17 — The coolest booth on the circuit

    02:45 — "X for AI," three years later

    03:40 — The agency owner has changed

    05:07 — The old guys in the back

    06:19 — From "I don't text" to "how do I grow?"

    07:04 — Commercial agencies moving into personal lines

    08:28 — A prediction for next year

    09:37 — Why doesn't insurance just come with the car?

    10:05 — Insurance like shipping on Amazon

    10:44 — Close: see you at ITC 2027


    Hosts

    Matthew Black — Founder + CEO, Mav

    Hillary Black — Head of Brand and Conversation Design, Mav


    Links and Resources

    ITC Vegas (InsureTech Connect), the world's largest insurance innovation event

    Toyota Insurance, the automaker-owned agency selling coverage alongside the car


    Follow the show

    Manual Work is a Bug is Mav's podcast, now on video. Watch on YouTube and follow wherever you listen, so you don't wait another six years for the next episode. Mav helps insurance agencies grow their book with AI: hiremav.com.


    Spotify

    Amazon Music

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    11 mins
  • How We Rebuilt Our Entire Website in Two Weeks with Claude Code (and Actually Made it Look Good)

    How We Rebuilt Our Entire Website in Two Weeks with Claude Code (and Actually Made it Look Good)
    Oct 2 2026
    This week we're walking through the entire process of rebuilding and redesigning the ⁠hiremav.com⁠ website using Claude Code, the Figma MCP, and two humans. ⁠Mav⁠ Founder + CEO ⁠Matthew Black⁠ and Head of Brand ⁠Hillary Black⁠ walk through the exact process from ideas to setup, iterating, and launching, plus where humans stepped in to make it not look like every other AI-generated website. We think it's looks pretty cool. Hillary, a non-engineer, was able to build the website of her dreams the exact way she wanted without waiting weeks to fit it into a sprint cycle, and the Claude Code "other tab" even convinced Matthew to use the Claude App instead of terminal for his work. On the table: why buying a hundred old insurance agencies and trying to AI-enable them doesn't work, the one rule that kept the site from looking AI generated, the tells that give an AI website away, a dev setup that went from four hours to thirty minutes, whether a website should even be the same for every visitor, and an Easter egg worth a free year of Mav.🥚 There's an Easter egg hidden on the new ⁠hiremav.com⁠. Find it, screenshot it, and DM Matthew on LinkedIn. First one gets a free year of Mav.Chapters⁠00:00⁠ — Intro⁠00:15⁠ — Cold open: we're live⁠01:01⁠ — The TV nobody could find⁠04:21⁠ — Too many humans in the way⁠04:49⁠ — Why the AI roll-up doesn't work⁠06:29⁠ — Buying the business for parts⁠07:11⁠ — Today: replacing ⁠hiremav.com⁠⁠08:08⁠ — Twenty new pages, two people⁠09:35⁠ — No staging server, no CMS⁠10:45⁠ — AI started, human finished⁠11:28⁠ — "I'm not a designer"⁠13:04⁠ — Was the wireframe holding it back?⁠14:17⁠ — The tells of an AI website⁠15:43⁠ — A four-hour setup in thirty minutes⁠16:57⁠ — Claude Code in the app⁠18:28⁠ — Every page, tracked⁠20:42⁠ — What even is a website anymore?⁠22:01⁠ — The new AI use case: create constraints⁠25:08⁠ — Using humans where it counts⁠26:01⁠ — One button and it's live⁠27:06⁠ — The Easter eggHosts⁠Matthew Black⁠ — Founder + CEO, Mav ⁠Hillary Black⁠ — Head of Brand and Conversation Design, MavLinks and ResourcesThe new ⁠hiremav.com⁠ ⁠Claude Code⁠, what Matthew pointed at the README and what built the pages ⁠Claude Code and Figma⁠: setting up the MCP server, the connection that let Claude read the actual design file ⁠Guide to the Figma MCP server⁠ ⁠Model Context Protocol⁠, the open standard behind the Figma connection ⁠ngrok⁠, how Hillary's local build gets shared with anyone ⁠Docker⁠, the self-contained dev environments ⁠micro1⁠, the AI training-data company Matthew mentions Follow the showManual Work is a Bug is Mav's podcast, now on video. Watch on YouTube and follow wherever you listen, so you don't wait another six years for the next episode. Mav helps insurance agencies grow their book with AI: ⁠hiremav.com⁠.⁠Spotify⁠ ⁠Amazon Music⁠
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    30 mins
  • Where AI Outperforms Humans, and What the Best Use Cases Have in Common

    Where AI Outperforms Humans, and What the Best Use Cases Have in Common
    Sep 25 2026
    After two weeks of AI getting it wrong, let's talk about where AI gets it right. Founder + CEO Matthew Black and Head of Brand Hillary Black go looking for the places AI genuinely outperforms a human, and what those use cases have in common.It starts with a car that drives itself better every month, and an insurance company that charges you less the more you don't do your own driving.We talk: why Tesla's lead in autonomous driving may be impossible to catch, the difference between selling tokens and selling outcomes, why everyone's AI flyers look the same, a data broker's offer that stopped Matthew cold, why CRMs are graveyards, and his MCP setup that replaced a personal trainer.Chapters00:00 — Intro00:15 — Cold open: ten episodes in01:10 — Starlink at cruising altitude03:40 — The chairs: a final update05:04 — When nobody can override anything07:01 — Tesla self-driving, six years later08:24 — Insurance that pays you to let the AI drive09:46 — Why Tesla wins: the data nobody else has10:54 — Sell outcomes, not tokens12:22 — Why all the flyers look identical13:29 — Data is being brokered like oil14:04 — You can't be an AI wrapper anymore16:37 — Tesla isn't a car company17:57 — The company that can't use its own data19:53 — Choosing tools by what they connect to21:03 — Why do you even need a CRM?21:38 — No steering wheel, no pedals22:48 — What agencies can do at a smaller scale24:35 — The fitness stack that replaced a trainer27:16 — The bridge is hard29:40 — Why Mav went all the way into insuranceHostsMatthew Black — Founder + CEO, MavHillary Black — Head of Brand and Conversation Design, MavLinks and ResourcesTesla Insurance: how the Full Self-Driving discount worksLemonade's Autonomous Car insurance, roughly 50% off every mile driven on FSDTesla, Uber and Waymo all get the OK to run thousands of robotaxis in NevadaModel Context Protocol, the open standard behind connecting your tools to Claude athletedata, a single MCP server that connects WHOOP, Hevy, MyFitnessPal and 30 more fitness apps to ClaudeRippling, the not-a-sponsor Follow the showManual Work is a Bug is Mav's podcast, now on video. Watch on YouTube and follow wherever you listen, so you don't wait another six years for the next episode. Mav helps insurance agencies grow their book with AI.
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    31 mins
  • Why AI Customer Service Keeps Failing and What It Might Be Costing Your Business

    Why AI Customer Service Keeps Failing and What It Might Be Costing Your Business
    Sep 18 2026
    We're an AI company, but we won't sell you AI for customer service (yet). Here's why we're so bothered by it. Mav Founder + CEO Matthew Black and Head of Brand Hillary Black get into why the thing everyone is automating first for some reason, is also the thing that breaks most often, and potentially costs your business the most.Hillary is bothered. Three sets of chairs, a retailer with no phone number, and a bot that can talk all day without doing a single thing about it.On the table: the one company Matthew thinks actually gets this right, the two conditions that separate a support experience that works for customers, from one that wastes an hour of your life, the unit economics nobody considers before they switch off their phone lines, what happens when your agent starts talking directly to the store's agent, and a mall built entirely for AI.Chapters00:34 — Cold open: three sets of chairs and no phone number02:35 — Why some AI support is good and most of it isn't03:21 — Why Mav stayed out of customer service on purpose04:10 — Sales is a formula. Support is one-out-of-one.06:34 — 27 entry points vs. 3, and the unit economics nobody runs08:43 — Cheaper per conversation, more expensive per customer09:01 — The one that actually worked10:50 — The two conditions12:06 — Onboarding a rep with no access to inventory12:30 — Saying the right thing doesn't matter if it can't do the job14:30 — Muse, and what happens when agents talk to agents16:24 — Meta bought the agent forum18:13 — MoltMall20:01 — Everyone is doing the best they can22:19 — The fold phone detour23:52 — Go win somewhere easier first24:25 — The worst possible place to put AI in insurance26:16 — Reinvest the savings at the bottom of the funnel too27:37 — Why Chewy gets away with itHostsMatthew Black — Founder + CEO, Mav Hillary Black — Head of Brand and Conversation Design, Mav Links and ResourcesMeta's Muse — the personal agent launched September 8, described as OpenClaw for everyone OpenClaw — the open-source personal agent Muse is answeringMeta acquired Moltbook, the social network built for AI agents Model Context Protocol — the open standard behind agent-to-agent connection Stripe Support — the implementation Matthew holds up as the bar Chewy — Matthew's example of stellar customer serviceFollow the showManual Work is a Bug is Mav's podcast, now on video. Watch on YouTube and follow wherever you listen, so you don't wait another six years for the next episode. Mav helps insurance agencies grow their book with AI: hiremav.com.
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    29 mins
  • How People Actually Shop for Insurance With AI & How Agencies Can Show Up

    How People Actually Shop for Insurance With AI & How Agencies Can Show Up
    Sep 11 2026

    Your customer is about to ask an AI whether they're overpaying you. Mav Founder + CEO Matthew Black and Head of Brand Hillary Black get into what happens when people end up shopping for insurance when all they did was ask AI to fix their budget.On the table: the prop plane Matthew almost bought, why comparison sites can't help you with this, what Bitcoin taught him about how consumers trust, how a small agencies compete with big budgets, how to get your agency recommended by ChatGPT, what insurance will look like a decade from now, and a million dollar idea to win over your clients he gives away at the end.Hosts- Matthew Black — Founder + CEO, Mav- Hillary Black — Head of Brand and Conversation Design, MavLinks and Resources- The Insurance Buzz with Michael Weaver and Courtney Weaver — the agency-side version of this conversation, with Matthew- Insurify's ChatGPT app — real-time personalized auto quotes inside the chat, the execution Matthew points to- How Insurify's app started, back in February — rate estimates and side-by-side comparisons from a database of 196M quotes- The insurer ChatGPT apps directory — who else is already quoting inside an assistant- Why quoting inside the assistant is the whole game, including Liberty Mutual making the first move among US carriers- Model Context Protocol — the open standard that makes any of this connectable- Tesla Insurance — insurance as a line item in the purchase wizardFollow the showManual Work is a Bug is Mav's podcast, now on video. Watch on YouTube and follow wherever you listen, so you don't wait another six years for the next episode. Mav helps insurance agencies grow their book with AI: hiremav.com.
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    30 mins
  • Where to Start Using AI in Your Business (and Where to Never Use It)

    Where to Start Using AI in Your Business (and Where to Never Use It)
    Sep 4 2026
    If you found AI for the first time today, where would you start? Mav Founder + CEO Matthew Black and Head of Brand Hillary Black run the thought experiment: deserted island, you reenter civilization, and every tool that exists right now is sitting there waiting. What do you reach for first, and what should you never touch at all?On the table: the two questions that tell you where to start, why the thing everyone reaches for first is the wrong thing, Matthew's AI ick and the one skill he wishes he didn't have, why human outreach is quietly becoming an unfair advantage again, the engineering process Mav rebuilt after choking on its own AI code, an $18,000 Mac you can lease for the price of a Claude subscription, and a poker chip that came out looking like a fish.One of these is where to start. One of them is where to never use it.Hosts- Matthew Black — Founder + CEO, Mav- Hillary Black — Head of Brand and Conversation Design, MavWhere to learn moreRecord your screen, get a skill — the thing Matthew describes at 17:14- Record a Skill, in the Claude desktop app's Cowork "+" menu — you do the task once, narrate it, and Claude writes the skill- Codex Record & Replay — OpenAI's version, shipped a few weeks earlier; this walkthrough shows what the output actually looks likeHow to build skills, the thing Hillary's whole brand system runs on- Equipping agents for the real world with Agent Skills — Anthropic's engineering post, the best single explainer- Agent Skills docs — what a SKILL.md actually is and where to put it- Introduction to Agent Skills — free Anthropic course, start-to-finish- anthropics/skills on GitHub — real working skills to copy from, including brand and document ones- agentskills.io — the open standard, so a skill you write isn't locked to one toolUsing AI for something other than making content- Claude Cowork — the "give it access to your actual files and tools" product- Model Context Protocol — the open standard behind every connector, if you want to understand why access matters- Claude Code — what you'd use to point a local model at your own machineLocal Model TalksLlama — Meta's open-weight models, free to download and run yourself- Apple's new Mac Studio- AppleInsider on the M5 Max and M5 Ultra refreshFollow the showManual Work is a Bug is Mav's podcast, now on video. Watch on YouTube and follow wherever you listen, so you don't wait another six years for the next episode. Mav helps insurance agencies grow their book with AI: hiremav.com.
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    32 mins
  • AI Conspiracy Theories: True or False?

    AI Conspiracy Theories: True or False?
    Aug 28 2026

    Get hour tinfoil hats out, this week we're talking about 10 AI conspiracy theories. Mav Founder + CEO Matthew Black and Head of Brand Hillary Black go through the internet's darkest, strangest and weirdest AI theories. Real, or fever dream?On the list: Google buying a dead airline's data. Shredding rare books for the sake of AI. The dead internet theory. An agent-only forum where the bots allegedly invented their own language in thirty-six hours. Labs poisoning their own models to keep them to themselves. An AI sentience cover-up. Simulation theory. People marrying their AI. And an ad campaign asking America to cool the data centers with pee.Some of these have press releases. Some of them should have stayed on the internet.

    Links and Resources

    • Anthropic on detecting and preventing distillation attacks
    • Google bought Spirit Airlines' data for $10M — 100M emails, 500M Teams messages, 30M lines of code
    • Why that data is worth it — teaching agents white-collar work needs private records, not public code
    • 404 Media hid a tracker in a rare book and followed it to an Amazon AI facility in Las Vegas
    • Amazon, which started as a bookstore, is destroying rare books to train AI
    • Cloudflare on bot traffic passing human traffic
    • Moltbook — the Reddit-style social network only AI agents can post on
    • Thinking Machines Lab — Mira Murati's company, the ex-OpenAI CTO
    • Love at First Prompt by Bridget Todd — on relationships between people and AI
    • Liquid Death x Garage Beer, "We Want Your Pee"
    • Can we actually cool data centers with pee?

    Follow the showManual Work is a Bug is Mav's podcast, now on video. Watch on YouTube and follow wherever you listen, so you don't wait another six years for the next episode. Mav helps insurance agencies grow their book with AI: hiremav.com
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    38 mins