Nicholas Rudder is the co-founder and CEO of Sphere, an AI-powered cross-border tax compliance platform that helps businesses navigate international sales tax, VAT, and GST regulations. After pivoting from a failed EdTech marketplace and losing his technical co-founder, Nicholas just raised $21M in Series A funding from Andreessen Horowitz—a remarkable comeback story that includes selling his first five contracts using only a Figma prototype.

What you'll learn:

1. How Sphere is becoming the "Deel of revenue compliance" for global businesses
2. Why Nicholas pivoted from EdTech after 18 months and what made him choose tax compliance
3. The strategy of selling contracts with a high-fidelity Figma prototype before building the product
4. How to convince investors to back a pivot when your co-founder has left
5. Why businesses struggle with international tax compliance and how AI solves it
6. The importance of hiring an internal recruiter once you raise significant funding
7. Why San Francisco remains the best place to build a startup despite the challenges
8. How YC's network helped navigate a critical health insurance crisis
9. The advantage of being a solo founder when recruiting high-quality founding engineers
10. Why raising from a position of strength creates better fundraising dynamics

In this episode, we cover:

(00:00 ) Introduction to Nicholas Rudder and Sphere

(01:10 ) The EdTech marketplace that didn't work

(03:08 ) Why EdTech is such a difficult market

(09:16 ) The hard pivot to tax compliance

(10:56 ) Selling five contracts with a Figma prototype

(13:10 ) When the co-founder left and twins arrived early

(21:58 ) Why international tax compliance is broken

(27:10 ) Sphere's vision as the "Deel of revenue compliance"

(31:34 ) The unintentional path to Andreessen Horowitz

(38:54 ) Why VCs all know when you're raising

(41:37 ) Building Sphere in SF vs. the UK or Australia

(46:23 ) Immad's advice on hiring internal recruiters

(51:14 ) Rapid fire: Founder inspirations and lessons learned