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:

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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Episode 787 | "We Shut Down a $1.5M Product, and Raised $10M Instead"

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