Speakeasy Mastermind is a curated community where established entrepreneurs meet monthly in person to work through real business challenges, share what's working, and build trusted relationships with peers. Each local chapter is part of a wider network, giving members ways to connect, learn, and build relationships beyond their home city.

Your local chapter is the heart of the experience: a consistent room of entrepreneurs who get to know one another and can work through real business questions together over time. Membership also connects you to the larger Speakeasy network, so you can learn from conversations across chapters, meet members in other cities, and build relationships beyond your local room.

Speakeasy is for established founders, business owners, and senior leaders who are still building and want thoughtful, experienced peers around them. Many members lead businesses with more than $1 million in net revenue, or earn at least $250,000 in net income as owners, or are senior executives at companies generating more than $10 million in revenue. We also value people who are open, generous with their experience, and willing to contribute to the room.

Revenue is one useful indicator of business experience, but it doesn't tell the whole story. We also consider your role, accomplishments, trajectory, the challenges you're working through, and how you might contribute to other members. Speakeasy is strongest when people are willing to share what they've learned, ask honest questions, make thoughtful introductions, and help make the room valuable for everyone

A typical Speakeasy meeting brings together 15–30 carefully selected entrepreneurs for about three hours, usually over dinner and drinks. Members share the decisions, opportunities, and challenges they're facing, then draw on the room for perspective, feedback, ideas, and introductions. There are no guest speakers, required pitches, or referral quotas; the focus is on the members and the conversation.

One member might bring a hiring decision they're weighing, another a growth opportunity that could stretch the business, and someone else a recurring operational problem they haven't been able to solve. The group asks questions, offers perspectives from its own experience, challenges assumptions, and helps the member consider practical next steps. The conversation is shaped by what members are dealing with - not a preset lecture or sales presentation.

Speakeasy centers on a monthly, in-person peer mastermind: entrepreneurs bring current business questions to a curated room and learn from one another's experience. It isn't built around pitching or meeting referral quotas, and it isn't a coaching program where one coach directs the conversation. Members may do business together, but the focus is on trusted relationships, candid discussion, and mutual contribution.

The core experience is peer-led: members learn from one another's firsthand experience in a trusted local room. There isn't one coach delivering a program or a meeting agenda centered on pitching and referrals. Members can still make introductions and do business together, but the value begins with candid conversation, useful perspective, and relationships built over repeated meetings.

Speakeasy Mastermind currently has 21 active chapters, with 6 more preparing to launch in the next six months and 10 additional communities forming with the goal of launching within the next 12 months. That's a growing network of 37 active and planned communities across the U.S. and internationally.

The chapter directory has the current locations and their status. If there isn't a local chapter near you, qualified entrepreneurs can explore Speakeasy Global for virtual experiences, connections across the network, and opportunities to visit chapters while traveling.

Speakeasy is designed for established entrepreneurs and business leaders who can both benefit from and contribute to a high-caliber peer community. Typical business guideposts include more than $1 million in net business revenue, at least $250,000 in owner net income, or a senior executive role at a company with more than $10 million in revenue. Recent founders who exited a company meeting those guideposts may also be a fit. These are guideposts, not the only factors: experience, trajectory, and what you'll bring to the community matter too.

Speakeasy may not be the right fit for people who are still in the startup phase. If you've been in business for less than 12 months and are still getting your company established, you're probably too early for the experience and stage of business represented in the room.

It may also not be the right fit if your business generates less than $1 million in annual revenue or, as a solopreneur, you earn less than $250,000 in personal income. These are general guideposts for the level of experience and scale we look for.

Speakeasy is also not for people who are primarily looking to pitch, collect referrals, or find clients among other members. It's generally not a fit for individual real estate agents, mortgage brokers, insurance agents, financial advisors, accountants, attorneys, or similar referral-driven service businesses. Members are expected to contribute their experience and build genuine peer relationships over time.

Standard Speakeasy membership is $5,995 per year. This annual membership covers your monthly in-person mastermind meetings in your home chapter, including dinner and drinks, along with access to the broader Speakeasy community. That wider access includes other chapter meetings when you travel, Insider Sessions, virtual networking experiences, shared meeting insights and resources, the member directory, and AI-powered knowledge search.

Your first meeting is complimentary if you're approved to attend, so you can experience the community before deciding whether membership is right for you.

Some launching chapters may offer special founding-member pricing.