The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
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The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
Episode 787 | "We Shut Down a $1.5M Product, and Raised $10M Instead"
Startups For the Rest of Us
37 minutes 48 seconds
1 week ago
Episode 787 | "We Shut Down a $1.5M Product, and Raised $10M Instead"
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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Startups For the Rest of Us
The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
