Startups For the Rest of Us Episode 787 | "We Shut Down a $1.5M Product, and Raised $10M Instead"
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Aug 12, 2025 Braden Dennis, co-founder of Fiscal.ai (formerly FinChat), shares his unique journey of bootstrapping and transitioning to a venture-backed model. He reveals the challenging decision to shut down a $1.5M product to focus on long-term growth. The conversation explores his company’s rebranding efforts, the emotional transition into a CEO role while scaling, and the importance of a strong founding team in navigating tough choices. Braden also discusses the strategic pivot toward AI and the implications that come with raising $10M in funding.
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Rebrand To Avoid Being Pigeonholed
- The FinChat name boxed the product as a chat-only tool and blocked enterprise demos.
- Rebranding to Fiscal.ai signaled a broader data terminal and avoided corporate AI-chat bans.
Big Prize Needs Big Investment
- Going after large public-market data players required much more engineering and a serious B2B go-to-market.
- That ambition made raising a larger round necessary to fund data infrastructure and sales talent.
Pay For Sales That Scale Revenue
- Pay top salespeople well if they can deliver outsized ARR; it's a lever to scale fast.
- Treat high sales comp as an investment when it can generate 10x ARR back to the company.
