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How a two-time YC founder went from builder to investor to Head of Growth at Numeral

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Nate Matherson has spent 10+ years as a founder. He's built companies and even exited. After that first exit, he started angel investing in dozens of companies, then launched a fund.

Numeral was one of his early bets. He sent Numeral's CEO Sam an email. By the end of the day, he was working there as Head of Growth. Now he's helping scale the YC-backed sales tax platform serving over 2,000 customers.

Nate's seen what happens when founders don't think about sales tax. "They actually found out that they owed about a half million dollars in sales tax… the buyer subtracted that off what would have gone to the founders."

When Nate was a founder, he'd log into Stripe and that sales tax dashboard was lit up like a Christmas tree. Numeral does free nexus studies and monitoring — takes five minutes to set up, plugs into Stripe and Rippling, then runs itself.

They launched their SaaS product recently, and their whole concept is set it and forget it. They actually love it when customers don't log in. Some of Nate's new learnings? "When I was a founder, I was always pretty good at marketing. I was just marketing not-so-great products, which made marketing a lot harder." At Numeral, with the right product at the right time, everything clicked.

And he knows: great products make marketing easy. Timing makes it effortless.

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Key Topics Covered

• [00:10] $500K sales tax bill found during due diligence
• [01:10] What is nexus and how it triggers
• [01:51] From founder to angel to fund manager to operator
• [04:02] 10+ years building, angel investments, vc fund
• [05:27] Numeral: e-commerce to SaaS journey
• [08:12] States that tax SaaS + global VAT complexity
• [08:40] "Set it and forget it"
• [10:37] Free nexus study + monitoring in 5 minutes
• [11:24] What's working in growth
• [13:28] Great products make marketing easy, timing makes it effortless
• [14:25] Nate's investing rule per batch

Follow Nate Matherson:
X: @NateMatherson
LinkedIn: linkedin.com/in/natematherson

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Follow Numeral:
X: @numeral
YouTube: youtube.com/@numeraltax
Website: numeral.com
LinkedIn: linkedin.com/company/numeralhq

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‍FollowDavid Phillips:

‍X: https://x.com/davj

‍LinkedIn: https://www.linkedin.com/in/davjphillips

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Brought to you by: Fondo — All-in-one accounting for startups: fondo.com