From Side Project to Series B: How Learning Led to Product-Market Fit

Sep 4, 2025

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Dan Lee co-founded what would become Nooks while on leave from Stanford. He wasn’t solving sales. He was exploring remote collaboration during the pandemic.

But when they noticed that some of his most active users were in sales development — and that investors were starting to reach out — he followed the signal.

Today, Nooks is a sales AI platform used by teams at Seismic, Fivetran, and Modern Health, with $70 million in funding from Kleiner Perkins, Lachy Groom, and others.

In this episode, we talk about how Nooks evolved from a virtual office for remote collaboration into a fast-growing AI sales assistant platform. Dan shares what it’s like to raise a $43M Series B after an unplanned Series A, why he believes sales needs AI assistants, not agents, and how he built conviction in a space he had no background in.

If you’re an early-stage founder wondering how to navigate a pivot, build for an industry you’ve never worked in, or generate investor pull instead of push, listen in.

RUNTIME 36:32 EPISODE BREAKDOWN

(3:01) “ It started as a project, obviously became a company.”

(5:13) “ Everyone here is smarter than me in some way.”

(5:46) Which early signals indicated Nooks could be more than a side project?

(8:01) “ And then, investors approached and said, ‘oh, you should raise some money.’”

(10:11) “ I think it's a misconception to think that in the early days it's hard to do much without raising money.”

(11:15) Pivoting Nooks from a virtual collaboration platform to serving sales teams.

(14:26) “ At the time, it felt more like a focus than a pivot.”

(16:56) “ Coming from an engineering background, it's easy to think, ‘oh, sales, that's like a dirty job.’”

(20:50) “ We've been fortunate to have a very strong feedback loop with our users.”

(22:20) If you don’t have domain expertise, “ build a mental model of what is true north in terms of product value.”

(23:22) Nooks’ work culture is underpinned by two values: “ask why,” and “earn customer love.”

(26:25) Customer satisfaction ≠ Customer delight

(30:36) Why Nooks is building AI assistants, not AI agents.

(32:41) When it comes to hiring, Dan looks for people with “motivations that align well with Nooks.”

(34:39) One question Dan would have to ask a CEO if he were interviewing for a job with an early-stage startup.

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Thanks for listening!

– Walter.