Become a Speakeasy

Mastermind City Captain

Lead with impact. Grow your influence. Join the leadership of the

most powerful entrepreneur community in the world.

Apply to Be a Captain

Ideal Skill Set:

  • Facilitator Extraordinaire: Confident in leading meetings and ensuring discussions are engaging and productive.

  • Organized Leader: Capable of managing schedules, budgets, and follow-ups.

  • Playbook Pro: Able to follow and execute a proven framework for success using the Speakeasy Captain’s Playbook.

  • Relationship Builder: Comfortable with recruiting, meeting new people, and having meaningful conversations both over the phone and in person.

  • Team-Oriented: Skilled at working with an admin and chapter promoters (including an admin if applicable) to ensure smooth operations.

Time Commitment:

  • Monthly Meeting (3 hours): Lead your city’s mastermind meeting.

  • Leadership Call (1 hour/month): Collaborate with other Captains and HQ.

  • Additional Tasks (est 3 hours/month): Manage member recruitment, meeting prep, and post-meeting follow-ups.

  • Pre/Post Launch: Expect additional hours during your city’s launch phase or major transitions.

Key Roles & Responsibilities:

  1. Recruit & Retain Members: Attract top-tier entrepreneurs and ensure ongoing engagement.

  2. Member Support: Approve new members, handle renewals, and remove non-compliant members if necessary.

  3. Meeting Management: Plan the structure, moderate discussions, and ensure there are 1-2 presentations ready for each meeting.

  4. Admin Coordination:

    • Take on admin tasks if no additional support is hired such as RSVPs for upcoming meetings, food/drink order, confirming space, Community admin duties like posting events, note taking.

  5. Engagement:

    • Monitor member participation and ensure high show-up rates.

    • Ensure members are getting a great experience- may require 1 on 1 calls/meetings to check in from time to time.

    • Drive engagement on the Speakeasy Community app.

  6. Liaison to HQ: Be responsive to Speakeasy HQ for updates, feedback, and guidance.

  7. Ongoing Development: Attend monthly leadership meetings

  8. Team management:  Manage your leadership team, if applicable. That may include admin support, ambassadors that are there to help you recruit, and anyone else that is helping you run your chapter.

  9. Attend the Global Annual Event: Attend the annual meeting

Benefits of Being a City Captain:

  1. Financial Rewards: Earn Money per month through a percentage of membership revenue, the bigger chapter the more you made.

  2. Leadership Exposure: Build your reputation as a leader within your city and the global Speakeasy community.

  3. Credibility Builder: Level up your status in the industry with a “Captain Title”.

  4. Exclusive Networking: Deepen connections with top entrepreneurs locally and globally.

  5. Professional Growth: Gain valuable skills in leadership, facilitation, and community building.

If this sounds like a role you’d excel at, let us know! We’re always looking for dynamic leaders to grow the Speakeasy Mastermind community.

Inside the Role:

A City Captain’s Perspective

Get a real look into what it’s like to be a Speakeasy City Captain from those who are leading the charge.

Curt Maly

City Captain - Austin​

Being a captain of Austin, Texas, has put our business on hockey stick growth."​

Kat Merritt

City Captain - Salt Lake City

"The reason things like Speakeasy are so important is because relationships are everything."

Marni Hale

City Captain - Orange County

"Our role as the captain is really about creating that safe, supportive environment."

John Westley

City Ambassador - Orange County

"One of the great opportunities and benefits of being on the captain's team is to see Glenn and Eric fulfill on their promise to meet locally and connect globally."

Gemma Stone

City Captain - Calgary

"It's the creativity of bringing complex solutions in and having a number of people that are of a similar experience and similar value system. Creatively trying to solve those problems all together."

Brad Hart

City Ambassador - Scottsdale

"What I love about Glenn and Eric and what they've created with Speak Easy, it's a good mix of fun. It's a good mix of relationships and you get the results."

Miro Heyink

City Captain - Los Angeles

"Your network is everything." 
"The relationships are actually way more important than sort of the money."

Ready to Lead Your City?

We’re always looking for dynamic leaders to grow the Speakeasy Mastermind community.