"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech E64: Numeral CEO Sam Ross: Why I Abandoned My Profitable Business to Raise $50M for Something "Boring"
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Jan 7, 2026 Sam Ross, founder and CEO of Numeral and ex-product leader at Teespring and Airbnb, discusses his decision to pivot from a profitable venture to launch an AI-driven sales tax automation platform. He shares insights on the boring yet vital nature of sales tax compliance, the impact of a pivotal Supreme Court ruling, and how AI transforms traditional processes. With gripping anecdotes from his e-commerce experiences, Ross elaborates on the complexities of government systems and the challenges of navigating funding rounds, revealing the potential for smarter tools in automating tax solutions.
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AI Converts Services Into Product
- AI can turn services-heavy compliance work into an end-to-end automated product.
- This collapses accounting firms + legacy tools into a single vendor for many customers.
Founder Pain Sparked The Idea
- Sam ran e-commerce businesses doing tens of millions in sales and got hit by post-2018 nexus complexity.
- A West Virginia filing and penalties made him realize founders waste hours on non-core compliance work.
Validate By Getting Customers To Pay
- Validate demand before building: cold-email potential customers and ask for money to confirm willingness to pay.
- Use founder dogfooding and early paying customers as stronger signals than clicks or interest.