E64: Numeral CEO Sam Ross: Why I Abandoned My Profitable Business to Raise $50M for Something "Boring"

In this episode, Sasha Orloff sits down with Sam Ross, co-founder and CEO of Numeral and former product leader at Teespring and Airbnb, about raising Series B funding from Mayfield (following Benchmark's Series A and Uncork's seed) to build what he calls "the most boring AI company"—an end-to-end sales tax automation platform that uses AI to eliminate the manual burden of multi-state and international tax compliance for e-commerce and SaaS businesses, transforming a traditionally services-heavy industry into a fully automated solution that handles everything from nexus analysis and registration to filings and government correspondence.

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SPONSORS:

Notion

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Puzzle

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RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/sambross/

https://www.numeral.com

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X/SOCIAL:

@SpamRoss (Sam)

@sashaorloff (Sasha)

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TIMESTAMPS:

(00:00) Preview

(00:49) Intro

(01:22) Guest Introduction: Sam Ross

(01:44) Most boring AI company

(03:54) AI and sales tax

(06:08) Origin story and early challenges

(10:56) Building the business and first customers

(13:14) Sponsors: Notion | Puzzle

(14:36) Sales tax compliance and solutions

(17:12) Automating mail and customer engagement

(18:24) E-commerce and tax compliance challenges

(19:40) Marketplace tax exposure issues

(22:15) Government complexities and physical mail

(23:54) Founding story and funding journey

(30:55) AI innovations in tax compliance

(33:11) Future of AI and browser automation

(34:33) Wrap