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How We’re Building Flamingo

Flamingo 8 Episodes Aug 18, 2026

A behind-the-scenes podcast about building an AI-native software company. It focuses on the real systems, tools, and decisions behind a 15-person team creating an operating system for IT services. Each episode examines one internal system they built or adopted, explaining their choices and what went wrong. New episodes are released weekly.

Episodes

Do Hard Things Podcast With Michael Assraf Aug 18, 2026 2472 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

How We Priced OpenFrame & AI Without the Games Jul 20, 2026 894 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 manage content and online events with AI Jun 30, 2026 919 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.

Documentation That Writes Itself From Source Code Jun 9, 2026 897 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 s

Beyond Feature Requests: How We Run Customer Operations May 27, 2026 730 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 interview

A Live Roadmap Your Users Can Actually Vote On May 12, 2026 717 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.

How We Validate Every Lead Before It Touches Sales May 6, 2026 968 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 ac

The Operating System Every Startup Needs Apr 14, 2026 838 How does a 15-person startup compete with companies that have thousands of employees? Not by hiring more people – by making every internal process as automated as possible. In this intro episode, Flamingo CEO Michael Assraf walks through the operating philosophy behind the company: one unified codebase, one shared database, and five internal hubs that run marketing, product, revenue, people, and i

How We’re Building Flamingo

Episodes

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