Dorothy Li is the co-founder and CEO of The Real Roots, a startup designing IRL, guided, matched experiences to help adult women build real friendships. With years in mission-driven startups—and a founder’s obsession with “what actually works in real life”—she’s tackling loneliness as a solvable systems problem, not a personal failing.

With a clear read on why loneliness got louder after the pandemic—and why it suddenly became socially “okay” to admit it—Dorothy offers insights into modern community-building, the science (and art) of compatibility, and how AI can scale nuance without turning humans into spreadsheets.

In this episode, she discusses why “friendship products” fail when they stop at matching, how Real Roots engineers the conditions for closeness (compatibility + repeated contact + facilitated depth), and what she learned by concierge-running the first groups herself—before tech (and later, voice AI) made the model scale.

In Today’s Episode We Discuss:

00:01 Why Adult Friendship Feels So Hard

01:42 Dorothy Li’s Path to Building The Real Roots

04:12 Loneliness Isn’t New—It’s Just Finally Admitted

06:38 Why Friendship Was Never Properly “Designed”

08:55 The Failure of Matching-Only Friendship Products

11:06 What Actually Creates Closeness Between Strangers

13:18 What You Can’t Self-Report (But Matters Most)

15:34 Early Proof: When Friendships Really Stick

18:06 Men vs Women: Different Paths to Bonding

20:11 Inside The Real Roots Experience

22:57 Why Facilitation Changes Everything

25:04 Designing for Repetition, Not One-Offs

27:09 Scaling IRL Without Killing the Magic

29:41 Building a City-by-City Marketplace

32:08 What Growth Actually Looks Like Early On

35:02 The Awkward Phase Everyone Wants to Skip

37:40 The Founder Trap: Waiting Until You’re ‘Ready’

41:12 How AI Finally Made This Scalable

44:10 The Metrics That Actually Matter

47:36 What’s Next for The Real Roots

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