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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.
- 8 - 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.
Tue, 18 Aug 2026 - 7 - 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.
Mon, 20 Jul 2026 - 6 - 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.
Tue, 30 Jun 2026 - 5 - 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.
Tue, 09 Jun 2026 - 4 - 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.
Wed, 27 May 2026 - 3 - 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.
Tue, 12 May 2026 - 2 - 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.
Wed, 06 May 2026 - 1 - The Operating System Every Startup Needs
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 investor reporting with minimal human touch. Michael covers why transactional efficiency is non-negotiable for PLG businesses with sub-$100K ACVs, how Flamingo's unified architecture works across its website, community platform, and product, and what the five hubs (Marketing, Product, Revenue, People, and Company) do to disconnect scalability from headcount. This is the first episode of How We Are Building Flamingo – a weekly show for founders and operators who want to see inside another startup's operating system. Subscribe to follow along. Connect with Michael on LinkedIn: linkedin.com/in/michaelassraf Learn more: flamingo.run Our MSP podcast: openmsp.ai/podcasts
Tue, 14 Apr 2026
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