How To Make $80 Million ARR From A Mastermind Business

About this video

Chief’s founder discusses building a thriving community platform for senior executive women that achieved ~15,000 members, $60-100M in estimated recurring revenue, and a $1.1B valuation in just three years. Sam and Shaan explore Chief’s business model—a hybrid of community, coaching, and corporate sponsorship—and compare it to other membership businesses like YPO, Vistage, and Tiger 21, examining what makes Chief’s approach to member acquisition, retention, and engagement particularly effective.

Key takeaways

• Chief’s core value comes from monthly peer groups with an executive coach, not from programming or events; the platform succeeds by leading with community and galvanizing mission rather than curriculum or sponsorships.
• The founder prioritized brand positioning and exclusivity without social media presence, relying entirely on word-of-mouth and cold outreach to early members; companies sponsor membership because it signals investment in talent, and rejection triggers retention risk.
• Engagement challenges in community platforms can be solved by creating natural touch points and utility (like hiring/legal referrals) that pull members into the product, rather than relying on passive content consumption.
• Most prior community businesses (YPO, Vistage, World 50, Aventa) focused on CEOs/presidents or were events- or advertising-led; Chief’s bet on VP-and-above executive women identified an underserved, well-funded demographic with acute loneliness and a mission-driven galvanizing force.
• The founder prefers remaining heads-down and mission-focused over publicity, celebrating members over founders, and sees capital as enabling mission speed rather than hype—projecting 200+ years at current pace to reach gender parity in senior roles.

Episode details: published May 12, 2022 · 15K views · 52:22 long. Summary written by Self Growth Videos from the episode itself. The business ideas, figures and results discussed are the hosts’ and guests’ own claims, shared as brainstorming and entertainment — not verified facts and not investment advice.

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