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.

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!