Produced by W2D1 Media. Work with us →
Sean Stuart

Sean Stuart

Co-Founder at Rosella

Sean Stuart is co-founder and chief executive of Rosella, an AI-native commercial insurance brokerage he started with Chris Dwyer, headquartered in Sydney and Austin. A UTS graduate and former venture capital investor, he was inspired to found the company after a 2023 fundraising run, roughly 80 marathon-equivalent distances from Florida to Canada, during which he developed septic cellulitis and could not access hospital care because he was uninsured. Rosella has since raised A$3.7 million in pre-seed funding co-led by Peak XV Partners and Intact Private Capital and is hiring brokers to serve small and mid-market US businesses. He detailed the story on Founders in Motion with Thea Ngo.

Watch the episode Jump to key moments

Key moments

Jump straight to the part of AI Insurance Brokerage: 80 Marathons, Uninsured, Nearly Killed Him | Sean Stuart, Rosella you want.

  1. 1:14 Schemer And Tinkerer
  2. 3:01 Novelty Over Experience
  3. 6:11 80 Marathons Begin
  4. 7:33 Septic Shock
  5. 10:34 What Is Rosella
  6. 12:55 Cold Calling America
  7. 15:00 The Bulldog Story
  8. 17:07 What We Got Wrong
  9. 19:01 What VCs Miss
  10. 23:04 Managing People Hard

Heard on

▶
Founders in Motion · 27 August 2026 AI Insurance Brokerage: 80 Marathons, Uninsured, Nearly Killed Him | Sean Stuart, Rosella

Rosella on Day One

Rosella Rosella is a Sydney and Austin-based AI-native commercial insurance brokerage that automates submissions across more than 100 carrier portals and uses AI to compare… 1 person · 1 episode →

Connections

Spot something wrong? Suggest a correction Updated 25 September 2026

Produced by W2D1 Media

Want a show of your own?

W2D1 Media — the team behind the Day One Network, which helped build Blackbird Ventures' Wild Hearts — builds and produces podcasts for funds, founders and operators. If you want a show built around your brand, let's talk.

Start a show →
—