Developer-Led Podcast: Bootstrapping a Commerical Open Source Company to $1M ARR
We’ve chosen to bootstrap Flagsmith and keep it open-source. We continue to do so while open-source companies in the space are actively raising external capital.
Flagsmith founder, Ben Rometsch, talked to Jonathan Reimer from Crowd.dev on the Developer-Led Podcast about building an open-source tool and continuing to refine our ICP and niche in the market in a rising tide.
Tune in to hear about what we’ve learned, the mistakes we made on the road to $1M ARR, and the type of company we choose to be.
Listen to the episode:
Some questions covered in the podcast:
- Why bootstrap?
- How can agency work complement growing an open-source company?
- How did we find our ICP? Which mistakes did we make while defining our ICP?
- How do we compete with other open-source competitors that have raised external capital?
- How do we position to customers as a bootstrapped team?
- How did we get to $1M ARR?
Why bootstrap?
We were running an agency alongside Flagsmith at the start, and that took a lot of the financial pressure off. It let us take our time and slowly refine our ICP as we grew.
We also don’t want to build the type of business that depends on VC funding. From the start, we knew we wanted to build a profitable business and make our own decisions with it. The agency work gave us the ability to grow to profitability at our own pace. Then, as the business grew we were able to slowly move over from the agency and dedicate more team members to the business full-time.
How do we stay competitive while other companies in the space are raising external capital?
We’re aware of the other businesses out there that are fundraising. We firmly believe in the superpower of small teams and our monolith product that’s simple to deploy. We’ve been very conscious in our decisions around what to build—and what not to build.
We’re a growing team, too, and we have great engineers that get a lot done. Plus we have support from external teams that help with content etc.
External capital comes with a lot of external pressures and requirements to keep up with, and you can become dependent on the next round. Investors will have stakes in things like pricing and upselling, which can become a moral hazard in the feature flagging space. There’s a lot of code lock-in with feature flags, and we’ve chosen to work with OpenFeature to prevent customers from being locked to a specific feature flag provider.
We’ve chosen to keep control over our growth and to give customers control over their feature flags as well.
How did we bootstrap $1M ARR by building a tool for open-source feature flags?
We had a steady stream of inbound leads from enterprise organisations that want enterprise licenses and on-premises feature flags, and that gave us a lot of direction. The pattern became clear and it was something we needed to look at.
We work with a team of three guys who have a tonne of experience in building companies up at this level. They helped us reorient our go-to-market strategy, focus on our ICP, develop a content strategy and so on.
We made a conscious decision to focus on a target customer that wants to run the platform in their own infrastructure.
Tune into the podcast to learn more about how we built Flagsmith and decided to focus on open source feature flags.
Relevant links
- Lessons Learned Along the Way to $1M ARR - to learn more about our experience building a bootstrapped company
- Our Flagsmith roadmap - to learn about upcoming features and the direction we’re going
- About Us - to learn more about who we are and why we're building the way we are
On-premises feature flags - to learn about self-hosting and how teams deploy to their own infrastructure

Dogfood Testing: Why We're Running Experimentation on Our Signup Page


Feature Toggle Management: A Practical Guide for Engineering Teams


The 7 Key Phases of the Software Development Lifecycle


How to Build a Software Rollback Strategy for Your Deployments


Server Side Testing: What It Is and How to Do It Right With Feature Flags


Alpha vs. Beta Testing: What’s the Difference and When Should You Use Each?


What Is Continuous Testing: The Ultimate Guide for Dev Teams


Regression Testing: Your Safety Net Before Code Reaches Users


What Is a Software Release? The Ultimate Guide


DORA Metrics Explained: The Five Measures of Software Delivery Performance


Explaining The Ring Deployment Model: Safer Releases, Ring by Ring


Feature Flags in DevOps: What They Are, Why You Need Them


What Is a Dark Launch? The Ultimate Software Development Guide


What Is Product Lifecycle Management?


What GitLab Feature Flags Can Do for Your Release Workflow


The Engineering Team's Guide to Release Strategies That Actually Work


You Can Now Integrate Flagsmith with GitLab! Here's How You Do It


The Benefits of A/B Testing, and Why Feature Flags Make It Even Better


The Developer's Playbook for Beta Testing That Actually Works


Code References: See Exactly Where Your Feature Flags Live in Your Codebase


What Is Blue-Green Deployment? The Complete Guide


Smoke Testing Explained: Catch Build Failures Before They Reach Your Users


When Canary Alerts Go Wrong: How We Fixed It and Doubled Down on OSS


Release Testing: A Complete Guide for Development Teams


What Is a Kill Switch in Software and Why Do Developers Need Them?


How to Implement CI/CD: A Practical Implementation Guide


What Is CI/CD? A Plain-English Guide to Faster, Safer Software Delivery


Rolling Deployment Vs. Blue-Green: Which Strategy Fits Your Pipeline?


What Is Feature Management and Why Does It Matter?


What Is Trunk-Based Development? A Complete Guide


Deployment Frequency: The Metric That Reveals How Fast Your Team Really Ships


OpenTelemetry, without the vendor lock-in: Introducing full observability for Open Source and Self-Hosted Flagsmith customers


How to Migrate from LaunchDarkly to OpenFeature in 6 Steps


How Prometheus, Flagsmith, and Some Good Old-Fashioned Compression Helped Us Solve Customer Pain


Feature Flag Testing: How Enterprise Teams Build Real Product Learning Loops


Trunk-Based Development vs. Gitflow: Choosing the Right Branching Strategy


Why OpenAI Paid $1.1 Billion for a Feature Flag Company


The Engineering Leader's Guide to Scaling Feature Flags


6 Tips to Reduce and Manage Technical Debt in 2026


Three teams. Eight hours. Three amazing features: Flagsmith’s 2026 Lisbon Offsite and Hackathon


Vibe Coding and Feature Flags: The New PM Playbook for Faster Product Validation


10 Best Practices to Build and Ship AI Features With Minimal Risk


Tracking Feature Flag Changes and Evaluation with Flagsmith and Sentry


We Built Our Own MCP Server for Engineers & Release Managers


7 PostHog Alternatives for Feature Flag Management


Why LaunchDarkly Went Dark During the AWS Outage—And Why Flagsmith Didn’t


Statsig Alternatives: 8 Best Feature Flag Platforms Compared


Integrating Datadog Workflows with Flagsmith for Automated Reliability


Progressive Delivery for Building LLM-Powered Features


What is the Four Eyes Principle? A Developer's Guide to Safer Flag Changes


De-Risking AI Adoption: How Feature Flags Help Enterprises Move Fast Without Breaking Trust


Monitoring Feature Flag Performance with Flagsmith, Prometheus, and Grafana


What is Release Management and How Does it Work in Regulated Industries?


Banking and Modern Observability: Dynatrace Insights


No More Hardening Phases: Testing in the Age of Continuous Deployment


How Modernisation is Changing Open Source Banking


Use Grafana to Track Feature Health in Flagsmith


6 Lessons From the World's Best Open-Source Founders


Feature Toggles and Feature Flags: Understanding the Key Differences


8 Types of Deployment Strategies (And How Feature Flags Help)


Moving to Progressive Delivery with Feature Flags


Top 7 Feature Flag Tools for Enterprises in 2026


Moving Fast, Without Breaking Things: Modern Software Delivery with Feature Flags


TypeScript Feature Flags: A Next.js Example


Embracing Modernisation in Banking Through Platform Engineering


Transitioning to Modern Authorisation Management


What Are Feature Flags? Everything Engineering Teams Need to Know


A Conversation with Komerční Banka's Chief Software Architect


GitOps for Feature Flags Using Terraform and Terrateam


Why It’s Time to Test in Production: Best Practices


How We Improved Our Docker Image Security Using Chainguard's Wolfi


6 Best Enterprise-Grade Harness Alternatives & Competitors


How to Roll out Pricing Changes With Zero Customer Complaints


How to Use Feature Flags for Trunk-Based Development


7 Best LaunchDarkly Alternatives & Competitors


How Global Banks Use Feature Flags to Stay Competitive


How To Guide: Flagsmith Grafana Integration


New in Flagsmith: 2024 Feature Roundup


Don’t Let a Flawed Release Take Your Company Down


How to Guide: Flagsmith GitHub Integration


6 Best Firebase Remote Config Alternatives & Competitors


How to Transition to Modern Feature Management in Banking


5 Feature Flag Management Pitfalls To Avoid To Keep Your Flags in Check

.png)
The Best Thing about Founding a Remote-First Company? Pickled Onion Monster Munch and The Beautiful Game

.png)
Flagsmith Jira Integration Guide: A Comprehensive How-to Guide

.png)
Guide: How to Create Observability-Driven Development with Feature Flags

.png)
Build vs. Buy for Feature Flags: My Experience as a CTO with a 20+ Engineer Team


Announcing the Flagsmith Referral Programme

.png)
How We Measure Feature Flags’ Success


Customer Story: Serenis

.png)
Announcing the Flagsmith Jira Integration


Spring Boot Feature Flags: A Step-by-Step Implementation Guide with a Working Java Spring Boot Application


Employees on Bootstrapping


Our POV: When Bootstrapping Works (and When It Doesn't)

How to Onboard Feature Flag Management Tools

When is it time to move to feature flag software?

Why We Bootstrap


The Enshittification of Basically all Digital Design. But in this Case, Specifically, the Slack Redesign.


Ruby Feature Flags: A Step-by-Step Guide to Implementing Feature Flags in a Ruby on Rails Application

Unlocking Efficiency: Transitioning to Modern CI Processes

.webp)