TradeWinds Investor Sails

Discover Founders, Drive Ventures

True Wind Culture Guests on a sailboat preparing for group challenge

Embark on a Tradewinds voyage designed specifically for investors seeking to deepen their understanding and connections with promising founders.

Through a carefully crafted sailing experience, we facilitate the building of relationship capital and accelerate the due diligence process.

By setting collaborative objectives, we create a unique environment where the authentic leadership qualities of each participant are brought to the forefront, fostering genuine and strategic partnerships.

Fast-track rapport and unlock potential as you navigate
the dynamic conditions of the beautiful San Francisco Bay.

Close up view of SF golden gate bridge from a sailboat
True Wind Culture Leader Guest taking the helm on a sailboat in SF Bay

The Experience

Sail in Style

  • Onboard a stunning, modern, spacious 40ft or greater yacht with sleek automatic inflatable vests.

Intimacy

  • An exclusive circle of 6 guests* ensures focused attention and meaningful connections.

Location

  • Sails are in the heart of the San Francisco Bay, departing from Sausalito or Alameda.

Professional Guidance

  • A USCG-certified captain ensures a safe journey alongside your Chief Wayfinder, who facilitates a customized program steered for growth.

*(Larger groups can be accommodated)

Personalized Preparation

  • Your voyage starts long before you touch the water with 1-on-1 consultations tailoring the journey to you and continues even after you dock.

No sailing experience is required. We’ve got you!
Our captains are also trained instructors.

What Makes Our Program Unique

  • Insightful Evaluation: By grasping the nuances of current investor-founder dynamics and collaboratively setting sail objectives, we facilitate a unique assessment environment. This approach focuses on unveiling core leadership traits—resilience, growth mindset, and integrity—amidst real-world scenarios, providing investors with a profound understanding of a founder's adaptability and potential.

  • Human-Centered Leadership Approach: At the heart of our culture is a human-first philosophy. We embrace anonymity among guests to encourage introductions based solely on first names and personal joys, sidelining titles and professional backgrounds. This approach fosters an environment of authenticity and open-mindedness, allowing for deep, genuine connections free from judgment or bias. Rest assured, identities will be shared as the journey concludes, enriching the experience with meaningful revelations.

  • Get Active & Present: Engage in hands-on sailing to challenge your limits. Experience freedom from your daily life by handling lines, steering, and trimming the sails, pushing you out of your comfort zone for 3-4 hours of immersive learning.

  • Dynamic Role Rotation: Experience the thrill and challenge of adopting different roles aboard, fostering adaptability, and enhancing your ability to lead and collaborate under varying circumstances.

  • Innovative Group Challenges: Embark on specially designed group challenges that are not only thrilling but also strategically crafted to unlock new levels of confidence, collaboration, and personal insight. These challenges serve as a catalyst for discovery, teaching you about your resilience and adaptability as well as your crewmates.

  • Insightful Reflective Discussions: Engage in meaningful dialogues that bridge your sailing experiences with real-world leadership scenarios, offering personal and professional revelations.

  • Signature Docktailing™ Celebration: Cap off the experience with our festive group roundtable to reflect, share lessons learned, cement memories, with engaging activities designed to anchor your journey together as a newly formed crew.

  • Become the True Crew: Embark on a voyage with us and gain access with an exclusive membership to a community that continues the growth adventure.

FAQ

Aerial view of South Beach Harbor in SF and the Bay Bridge

  • Everything we do is customizable. Let’s chat!

    Yes! We can accommodate groups larger than 6. Prices will vary based on boat size and number of guests.

  • Everything we do is customizable. Let’s Chat!

    We can co-brand sailing jackets, shirts, caps, backpacks, etc., and make it memorable for your team.

  • Sample Event Flow

    • 9:00 am Group welcome and introductions dockside

    • Rules, roles, and goals of the day

    • Captain safety briefing and sailing basics

    • Departure with sailing instructions, practice and group challenges (2 hours of sailing time)

    • Lunch anchored off Angel Island

    • Sailing and more group challenges

    • 4:00 pm Return for Docktailing™ celebration

    • 5:00 pm Guests depart