How We’re Building Flamingo

Flamingo
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A behind-the-scenes podcast about what it takes to build an AI-native software company. No fundraising advice, no startup platitudes – just the real systems, tools, and decisions behind a 15-person team building an operating system for IT services. Each episode digs into one internal system we built or adopted, why we made the choices we did, and what broke along the way. New episodes every week.

Episodes

  1. Aug 18

    Do Hard Things Podcast With Michael Assraf

    Michael Assraf spent nine years building Vicarius, a cybersecurity company he co-founded in Israel in 2016 and led through $60M in funding. Then he walked away from it to start over in a market most investors can't define. In this episode with Gabe and Lexi, Michael explains why. Software replacing software is a pattern we've seen for decades. Software replacing services is something else, and he thinks it's the biggest shift since the industrial revolution. That view took him to managed service providers: the outsourced IT firms that keep small businesses running, squeezed between rising vendor costs and rising labor costs, working with tools designed 20 years ago. He also gets specific about what he's doing differently the second time. Distribution before product. A community built before there was anything to sell. And a rule about not handing off go-to-market until the sales motion is repeatable, because trying it earlier is what failed at his first company.

    Do Hard Things Podcast With Michael Assraf

  2. Jul 20 ·  Video

    How We Priced OpenFrame & AI Without the Games

    Straight pricing shouldn't need a sales call. Here's how we built OpenFrame's. Vlad Marchenko, Head of Marketing at Flamingo, covers the $1-per-device model, why we went per device over per technician, and how we priced AI tokens so the bill actually makes sense.

    How We Priced OpenFrame & AI Without the Games

  3. Jun 30 ·  Video

    How we manage content and online events with AI

    We publish content across 4 platforms, run an active Slack community of 600+ MSPs, manage 193 vendor analysis pages with thousands of community votes, and host online events. All of it is run by two people with AI assistance. In this episode, Michael shows how we manage the content calendar, community moderation, online event logistics, and why doing all of it from a single system matters.

    How we manage content and online events with AI

  4. Jun 9 ·  Video

    Documentation That Writes Itself From Source Code

    Generating documentation. We don't have a product manager. Instead, our system watches what the engineering team ships and automatically generates reference docs, tutorials, and feature specs from the source code. We talk about the time it hallucinated setup instructions that didn't exist, how we fixed the trust hierarchy between generated docs and manual notes, and why auto-documentation is the single biggest force multiplier for a small team.

    Documentation That Writes Itself From Source Code

  5. May 27 ·  Video

    Beyond Feature Requests: How We Run Customer Operations

    Interviews and case study management. Every beta customer who did a case study agreed to go on video - 100% participation rate across 11 customers managing 5,000+ endpoints. We built an internal conviction dashboard that tracks every customer conversation, maps intent tiers, and connects interview data to revenue projections. Before we turn on billing, we're running structured validation interviews with our top 50 customers to pressure-test willingness to pay.

    Beyond Feature Requests: How We Run Customer Operations

  6. May 12 ·  Video

    A Live Roadmap Your Users Can Actually Vote On

    Roadmap and delivery management. Our product roadmap is public. Users can see what we're building, vote on features, and track what shipped. Behind the scenes it's synced to our project management system so votes from the community feed directly into sprint priorities. We also track every bug fix and enhancement with live status updates, and coordinate across a global team through the same tool.

    A Live Roadmap Your Users Can Actually Vote On

  7. May 6 ·  Video

    How We Validate Every Lead Before It Touches Sales

    Lead validation and access code management. We built an internal system that scores every MSP signup before they ever get access to the product. It detects whether a company is actually an MSP, researches them across the web, assigns confidence scores, and syncs everything to our CRM automatically. We control who gets in through cohort-based access codes - 2,090 signups, 585 granted access, 196 actively using the product. Every step is gated and measured.

    How We Validate Every Lead Before It Touches Sales
  • 7 Episodes

About

A behind-the-scenes podcast about what it takes to build an AI-native software company. No fundraising advice, no startup platitudes – just the real systems, tools, and decisions behind a 15-person team building an operating system for IT services. Each episode digs into one internal system we built or adopted, why we made the choices we did, and what broke along the way. New episodes every week.

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