FAQs

  • Punks & Pinstripes is an exclusive executive community for Business Punks.

  • We’re not for everyone—and that’s the point.
    We’re Business Punks. We’re the executives and entrepreneurs who don’t necessarily blend in. This is not a networking group - it’s a community, We talk about our hardest challenges and empower one another to get through them.

  • Our members fall into two categories:

    1. Corporate Punks: Corporate executives who are un-f*cking the biggest companies and industries in the world. 

    2. Exodus Entrepreneurs: Leaders who’ve left corporate executive leadership to launch startups.

    If you’re bold, intentional, and ready to redefine what leadership looks like, this is your tribe.

  • Membership is $7,000 per year and includes:

    • Access to private, highly curated events.

    • A powerful network of peers who challenge, inspire, and support you.

    • Ongoing opportunities to connect, learn, and grow with like-minded leaders.

  • Membership is by referral only.

    • If you think you need what we offer, the only way to apply is through a current member referral.

    • Don’t know anyone in the community? Do your homework. Search LinkedIn, reach out, meet someone for coffee, come to one of our open events, and introduce yourself. We don’t bite.

  • We love you. But membership is only available to leaders based in New York City. The biggest value of the community is our in-person experiences, which all happen in NYC.

  • Membership is capped at 200 people to ensure quality and exclusivity. Our members talk about heavy shit, like going back to work after a sibling dies and getting sober while in the C-Suite. There are a small number of executives who can honor that level of vulnerability, and we won’t dilute it.

  • Yes. Not because we’re assholes, but because we’ve seen what works (and what doesn’t). Here are the rules:

    1. No Selling. 

    2. Ask good questions. Get to the problem underneath the problem. The surface issue is never the real issue.

    3. Show your scars. What’s your experience with the same problem the member is wrestling with?

    4. Don’t give advice. Share your struggle and experience, but don’t recap the latest Seth Godin article from HBR.

    5. Call Bullshit. How is conventional thinking about the problem wrong? 

    6. Curb Your Ego. This isn’t a career beauty pageant.

  • Our events are designed to foster connection, spark creativity, and tackle real challenges. Here's what you can expect:

    Members-Only Events

    • Help a Punk: Intimate group-coaching sessions where one member shares their toughest challenge and receives actionable insights, support, and ideas from the group.

    • Feasts: Monthly, home-cooked dinners for 12 members, hosted in a member’s home. These gatherings are as personal as they are powerful.

    • Co-Working Days: Twice a month, members gather for collaborative work sessions—perfect for tackling big projects with a little peer support.

    • Retreats: Immersive experiences in incredible destinations like Copenhagen, Playa del Carmen, and Park City, where members dive deep into ideas, strategies, and connection.

    • The P&P Black Market : We don’t push this, but our members write books together, launch startups, co-invest and hire one another. All the time.  

    Open Events (Free for Members)

    • The Art of Outlaw Dinner Series: A monthly dinner in Brooklyn featuring conversations with misfits and rebels who build breakthroughs. Past guests include Stephen Gates, Reza Aslan, Cindy Gallop, Chuck D, and Bill Stephney.

  • If you know someone who’s already a member, reach out for a referral. If you don’t, take the time to connect with someone in the community—it’s worth the effort.

    When you’re ready to join, we’ll be here to welcome you into the fold.