Navigating Growth and Leadership Challenges

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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