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Empowering the Entrepreneur

At 50 Bosses Deep, we believe success begins with strong minds, strategic planning, and supportive communities. This initiative is committed to helping entrepreneurs grow holistically by focusing on business development, financial literacy, personal well-being, and empowerment. We’re here to help you thrive whether you’re starting up or scaling up.

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Our Programs

1

DEEP Conversations

Real growth starts with real talk. DEEP Conversations are guided discussions that tackle the personal and professional challenges entrepreneurs face.

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2

V.E.N.T. 

The V.E.N.T. Program is a safe and confidential space where entrepreneurs can release pressure, share frustrations, and celebrate wins while prioritizing their mental wellness and building healthier ways to navigate the challenges of entrepreneurship.​​

3

Boss Walks

Boss Walks are energizing walks that promote physical wellness while giving entrepreneurs and leaders a space to connect, refresh their minds, and exchange ideas.

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4

Black Business Bus Tour

The Black Business Tour empowers young people by connecting them with Black-owned businesses, leaders, and hands-on opportunities to build confidence, vision, and real-world career paths.

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5

The Conference

The 50 Bosses DEEP Business Conference brings together industry experts, creatives, and corporate executives to provide a framework that outlines a path for entrepreneurs.​

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50 Bosses Deep Conference 2026

Mindshift: Positioned to Win

Step into a room designed for growth, connection, and next-level execution.The 50 Bosses Deep Conference brings together driven entrepreneurs and leaders for two powerful days focused on mindset, strategy, and real momentum. Your ticket includes access to both days of the conference experience, curated sessions, and opportunities to connect with like-minded individuals who are serious about leveling up.

 

September 18–19 | Indianapolis, IN

Secure your spot now because this WILL sell out!

50 Bosses Deep Mindshift

Our Events

  • Boss Walks
    Boss Walks
    Sat, Apr 11
    Broad Ripple Park Family Center
    Apr 11, 2026, 9:30 AM – 11:30 AM
    Broad Ripple Park Family Center, 1426 Broad Ripple Ave suite 200, Indianapolis, IN 46220, USA
    Join us for a refreshing blend of movement, mindset, and meaningful conversation with a special presentation by Cassandra Raine-Francis!
  • Boss Walks
    Boss Walks
    Wed, Apr 22
    Broad Ripple Park Family Center
    Apr 22, 2026, 11:30 AM – 1:30 PM
    Broad Ripple Park Family Center, 1426 Broad Ripple Ave suite 200, Indianapolis, IN 46220, USA
    Join us for a refreshing blend of movement, mindset, and meaningful conversation with a special presentation by Christiane Michael David!
  • Boss Walks
    Boss Walks
    Sat, May 16
    Broad Ripple Park Family Center
    May 16, 2026, 9:30 AM – 11:30 AM
    Broad Ripple Park Family Center, 1426 Broad Ripple Ave suite 200, Indianapolis, IN 46220, USA
    Join us for a refreshing blend of movement, mindset, and meaningful conversation with a special presentation by Latoya Owens, NBCC, LMHC-A!
  • 50 Bosses Deep Conference 2026 - "MindShift: Positioned to Win"
    50 Bosses Deep Conference 2026 - "MindShift: Positioned to Win"
    Sat, Sep 19
    Visionloft Events Stutz
    Sep 19, 2026, 9:00 AM – 4:00 PM
    Visionloft Events Stutz, 1060 N Capitol Ave Suite 1-102, Indianapolis, IN 46204, USA
    Shift the mind. Change the game. The 50 Bosses Deep Conference brings together driven entrepreneurs and leaders for a powerful experience focused on mindset, strategy, and real momentum.

Support Our Mission

Your contribution helps us amplify voices, create opportunities, and sustain the work of 50 Bosses Deep. Every donation directly supports our programs, storytelling, and community impact. Click the button below to make a secure monetary donation and help us continue building what matters.

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