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

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

Author: Rob Walling August 12, 2025 Duration: 37:48
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! Subscribe & Review: iTunes | Spotify

Rob Walling hosts Startups For the Rest of Us, a long-running conversation focused squarely on the realities of building a company without massive venture funding. This isn't about Silicon Valley fairy tales; it's a practical, ground-level view of entrepreneurship. Each episode delves into the specific journeys of founders who are starting, acquiring, or growing their SaaS businesses, emphasizing the path of bootstrapping. You'll hear the unvarnished details-the strategic decisions, the unexpected obstacles, and the hard-won victories that define the daily life of a founder. The discussions are built on real stories, offering tangible lessons from both struggle and success. For anyone who has ever felt that the typical startup narrative doesn't reflect their own resource-constrained reality, this podcast provides a necessary and relatable perspective. It’s a deep resource for actionable advice and genuine camaraderie, connecting you with the experiences of those navigating the same challenging terrain. Tune in for honest conversations that cut through the hype and focus on building sustainable businesses.
Author: Language: en-us Episodes: 100

Startups For the Rest of Us
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