Episode 787 | "We Shut Down a $1.5M Product, and Raised $10M Instead"
Update: 2025-08-12
Description
How do you know it’s time to move on from a product that’s growing?
In this episode, Rob Walling chats with Braden Dennis, co-founder of Fiscal.ai (formerly FinChat), about a rare founder journey: bootstrapping, catching lightning in a bottle, and choosing to go big with venture capital. They dive into the emotional and strategic weight of shutting down a $1.5M ARR product, what shifts when you scale past 40 people, and why Braden prioritized long-term vision over short-term revenue.
Topics we cover:
- (2:30 ) – From FinChat to Fiscal.ai: rebranding and repositioning
- (6:50 ) – Why they raised a $10M Series A
- (13:09 ) – From bootstrapped to venture-backed: what changes?
- (19:56 ) – Becoming a real CEO at 25 employees
- (26:44 ) – Why they shut down a $1.5M product
- (30:30 ) – Lessons from having four co-founders
- (33:13 ) – The benefits of joining TinySeed
Links from the Show:
- MicroConf Connect
- The Great CEO Within
- TinySeed: SaaS Institute
- Fiscal.ai (formerly FinChat)
- Braden Dennis (@BradoCapital) | X
- Braden Dennis | LinkedIn
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
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