Founders in Motion with Thea Ngo 
About Sean Stuart
Sean Stuart is co-founder and chief executive of Rosella, an AI-native commercial insurance brokerage he started with Chris Dwyer to serve small and mid-sized US businesses. Rosella handles risk advice, placement, contract review and claims for operators in industries such as HVAC, trucking, construction, landscaping and professional services.
A UTS graduate, Stuart was working as a venture capital investor when the idea took shape. With three friends he ran about 80 marathons in 80 days from Florida to the Canadian border to raise money for cancer research, and the team ran uninsured because policies excluded extreme events. In April 2026 Rosella raised an A$3.7 million pre-seed round co-led by Peak XV Partners and Intact Private Capital.
On Founders in Motion with Thea Ngo, he told that story and explained what venture investors miss about AI-native service businesses.
- Talks about
- AI, Founder Journey, Going Global
In conversation.
1 episode
Founders in Motion with Thea Ngo Go straight to the good bits.
Key moments from AI Insurance Brokerage: 80 Marathons, Uninsured | Sean Stuart, Rosella.
Rosella on Day One
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
Across the network.
In the room with
Spot something wrong? Suggest a correctionUpdated 28 October 2026
Be part of
the conversation.
Put your brand alongside the voices founders, investors and operators come to hear.
Explore sponsorshipProduced 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.
