211. 420M downloads, 80M Active users, $200 M raised. Dmitry Gurski (Flo Health): “Don’t Listen to Negative Opinions. I Was Shy & Nerdy—20 Years Ago No One Would Believe I Could Lead a $1B++ company.” Leadership Lessons Behind the World’s #1 H
Tue Oct 07 2025
Dmitry Gurski founded Flo Health in 2015, turning it into the leading women’s health app globally with over 420 million downloads and 80 million monthly active users. From bootstrapped beginnings to a $200M Series C from General Atlantic in 2024 (valuing Flo at $1B+), Dmitry has scaled the company to profitability, with offices in Lithuania and the UK.
🎓 Expect to Learn:
- How Flo became a $1B+ company without a clear playbook — and why long-term planning is mostly fiction
- What 20 years of founder experience really teaches you — from stress tolerance to “rollercoaster immunity”
- Why all big organizations are ‘shiny outside, messy inside’ — and why that’s totally normal
- The hidden leadership lesson: never punish honest mistakes, but always bet on people with ownership mentality
- AI’s real challenge isn’t tech — it’s building interfaces that people actually want to use
- Why you should ignore negative people who question your background, pedigree, or ambition
- How crises shaped Flo’s evolution
- Why hiring interviews are overrated — and how real-world test work beats charisma every time
- The myth of growth = hiring — and how limiting headcount can actually make your company better
- How to stop bloated orgs: “Every layer you add cuts 30% efficiency.”
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If you liked this episode or simply want to support the work we do, buy us a coffee or two, or a hundred, with just a few clicks at: https://buymeacoffee.com/pursuitofscrappiness
Find all episodes on > https://www.pursuitofscrappiness.co/
Watch select full-length episodes on our YouTube channel > https://www.youtube.com/channel/UCP6ueaLnjS-CQfrMCm2EoTA
Connect with us on Linkedin > https://www.linkedin.com/company/pursuit-of-scrappiness/
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Dmitry Gurski founded Flo Health in 2015, turning it into the leading women’s health app globally with over 420 million downloads and 80 million monthly active users. From bootstrapped beginnings to a $200M Series C from General Atlantic in 2024 (valuing Flo at $1B+), Dmitry has scaled the company to profitability, with offices in Lithuania and the UK. 🎓 Expect to Learn: - How Flo became a $1B+ company without a clear playbook — and why long-term planning is mostly fiction - What 20 years of founder experience really teaches you — from stress tolerance to “rollercoaster immunity” - Why all big organizations are ‘shiny outside, messy inside’ — and why that’s totally normal - The hidden leadership lesson: never punish honest mistakes, but always bet on people with ownership mentality - AI’s real challenge isn’t tech — it’s building interfaces that people actually want to use - Why you should ignore negative people who question your background, pedigree, or ambition - How crises shaped Flo’s evolution - Why hiring interviews are overrated — and how real-world test work beats charisma every time - The myth of growth = hiring — and how limiting headcount can actually make your company better - How to stop bloated orgs: “Every layer you add cuts 30% efficiency.” == If you liked this episode or simply want to support the work we do, buy us a coffee or two, or a hundred, with just a few clicks at: https://buymeacoffee.com/pursuitofscrappiness Find all episodes on > https://www.pursuitofscrappiness.co/ Watch select full-length episodes on our YouTube channel > https://www.youtube.com/channel/UCP6ueaLnjS-CQfrMCm2EoTA Connect with us on Linkedin > https://www.linkedin.com/company/pursuit-of-scrappiness/ =============== Support the show