Debunking Myths About Bootstrapped Companies and Leadership Roles

With Oleks Yaroshenko

How do you scale an edtech startup into a company with 150 million users worldwide, without taking outside funding? And what’s it like building it from wartime Ukraine? In this episode, we sit down with Oleks Yaroshenko, Chief of Staff at Headway Inc, the company behind one of the world’s most popular lifelong learning apps. Previously known as Headway, the company officially evolved into Headway Inc, marking its transformation into a full-scale consumer tech platform. Oleks shares how the team navigated competition, used A/B testing as a superpower, and built resilience through necessity. We also dive into Ukraine’s growing startup scene and debunk some myths about bootstrapped growth.