Balancing human desire to connect with modern constraints

In this week’s episode, we’re joined by Lindsay Kaplan, co-founder of Chief, the women’s executive network that became one of the fastest-growing membership communities in the world — scaling from a cold-email experiment to a venture-backed unicorn in just a few years.

Lindsay shares the inside story of building a brand that reshaped executive leadership for women, from hacking together the first 200 members to navigating the existential shock of COVID, to stepping aside when she realized the company needed a fresh operator for its next chapter. Now an investor at Next Wave NYC, she breaks down what she’s learned from the operator’s seat — and why she’s betting big on founders building at the intersection of AI and real-world connection.

In this episode, we explore:

The origin story of Chief — how Lindsay and her co-founder turned a “shitty networking event” into the insight behind a new category: a confidential, high-intent community for women at the top of their fields.

Finding product-market fit from cold emails — why guessing email addresses, offering a clear promise, and creating “lukewarm outreach” led to explosive early traction.

Scaling a community across cities — the surprising discipline behind maintaining brand consistency while expanding from New York to markets across the U.S.

Surviving COVID in real time — how Chief rebuilt its entire in-person experience into a digital-first platform in days, not weeks — and why the crisis 10x’d demand for meaningful connection.

The co-founder relationship — Lindsay’s candid take on disagreement, shared values, and why the best partnerships feel like having someone “clean up your bloody nose” on the field.

Knowing when to step aside — the emotional and operational signals that told her she wasn’t the right person to run Chief for the next decade — and how founders can prevent burnout by being honest about their energy and passion.

What she’s investing in now — why Lindsay is bullish on AI as a productivity engine and on the rise of IRL experiences as a counterforce to digital fatigue.

Plus much more — from cap table strategy, to the future of membership-based businesses, to why the next great consumer brand will blend software, storytelling, and community.

This is one of the most insightful founder-to-investor journeys you’ll hear all year. Enjoy the episode!

Also available on Apple Podcasts // Spotify

Episode Chapters

(0:00) Intro

(2:00) The Mission To Build Chief

(3:18) Finding The First Members

(7:00) How To Launch In Multiple Cities

(8:52) The Hardest Early Day Challenges

(11:40) Adapting Within Days During COVID

(12:33) The Art Of A Great Co-Founder Relationship

(18:00) Raising $100M & Becoming A Unicorn

(19:25) Launching Physical Spaces

(20:59) Community Businesses vs AI

(23:32) 60,000 Members On The Waitlist

(24:30) The Members Experience

(25:43) Stepping Down

(30:00) Turning From Operator To Founder To VC

(35:53) Lindsay’s Big Ideas

Thanks for listening and see you in the next episode 👋

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