EUROPE BUILDS by BORRN How Headway Inc bootstrapped its way to 150 million users
May 30, 2025
In this engaging discussion, Oleks Yaroshenko, Chief of Staff at Headway Inc., shares how the company scaled to 150 million users without external funding, notably during turbulent times in Ukraine. He reveals the power of A/B testing in refining user experiences and discusses innovative strategies for user engagement and retention. Yaroshenko also highlights the resilience of the Ukrainian startup scene and debunks myths surrounding bootstrapped growth, emphasizing that success doesn't require sacrificing strong leadership.
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Bootstrapping Story of Headway
- Headway started with one product, a book summaries app competing with Blinkist but focused on unit economics from day one.
- They lacked luxury of external funding, which ingrained capital efficiency into their DNA driving survival in tough markets.
Fail Fast And Test One Thing
- Focus on one specific A-B test at a time to gain statistically significant data before making decisions.
- Fail fast and cheap to quickly learn but avoid spreading too thin across multiple tests simultaneously.
Broad Audience & Bite-Sized Learning
- Unlike Blinkist's CEO-focused marketing, Headway targeted busy adults broadly with a playful tone and short sessions.
- Features like spaced repetition reinforced bite-sized learning to help users improve step-by-step.