Key West

A Five-Day Immersive Investment Experience

Trust isn’t built over a pitch. Capital Circle invites you to experience investment through connection during five luxurious, intimate days in Key West, where fund managers, entrepreneurs, and investors forge real relationships.

The Capital Circle

Week of

September 18-22, 2025

Key West, Florida

Destination

Siol Venture Capital

Presented By

A Five-Day Immersive Investment Experience.

  • Day 1 – Thursday, September 18

    Arrive in Key West and be whisked away to our private 16-bedroom villa. Spend the afternoon unwinding by the pool before gathering for an intimate welcome cocktail hour. As the sun sets, enjoy a chef-prepared dinner paired with bespoke cocktails, setting the tone for the days ahead.

  • Day 2 – Friday, September 19

    Wake to a relaxed island morning before stepping aboard the Blind Squirrel for a private fishing adventure. The day unfolds at sea, with conversations as open as the horizon. Return to a late dinner crafted by a private chef, complemented by the easy elegance of a personal bartender.

  • Day 3 – Saturday, September 20

    The morning begins slowly, with a leisurely breakfast and a lunch gathering. In the afternoon, set sail on a private yacht, champagne in hand and caviar at the ready. As the evening arrives, a dinner presentation gives way to an unforgettable white party, where music and conversation carry late into the night.

  • Day 4 – Sunday, September 21

    After breakfast, choose your own pace—perhaps a round of golf, a massage, another afternoon on the water, or simply a quiet day by the pool. In the evening, enjoy special dinner reservations, whether an intimate date night with your partner or a lively group affair.

  • Day 5 – Monday, September 22

    Gather for a final breakfast with newfound friends before your departure. The conversations and connections linger, carrying forward far beyond the island.

The Capital Circle Experience

  • Trust isn’t built over a dinner. Capital Circle unfolds across four intentional days so conversations can breathe, rapport can deepen, and real partnership can take shape. We keep the guest list intimate—just 15 investors and their chosen partners—so every interaction is meaningful, private, and pressure-free. The result: confident decisions rooted in genuine relationships.

  • From arrival to farewell, the environment is curated to remove friction and elevate focus: 24/7 butler service, a private chef crafting bespoke menus, and a dedicated bartender shaping the mood with impeccable service. Hospitality here isn’t a perk—it’s the architecture that enables candid dialogue and effortless connection.

  • We design experiences that spark real conversation—yacht afternoons with champagne and caviar, a private day deep-sea fishing charter, and an elegant white party under the stars.

    Behind the ambiance is a track record that speaks for itself: a technology/licensing exit with marquee partners (Disney, Lamborghini, Givenchy) returning 200×, and a renewable energy investment on a path toward a 100× outcome. Capital Circle is where extraordinary experiences meet exceptional deal flow.

  • Great investments are often team decisions. We welcome spouses, romantic partners, and business partners—and program the week to be as enjoyable as it is productive. From relaxed mornings to memorable evenings, partners are thoughtfully included, creating shared context and alignment that accelerates clarity.

Siol Venture Capital

Síol Venture Capital grew out of MOB Advocacy - a government relations firm focused on startups and early stage tech. It provides early capital and public affairs expertise to help great early-stage startups grow.

Michael S O'Brien
Managing Partner

Elyssa Malin
Venture Partner

Elle Hempin
Venture Partner

Antione Thompson
Venture Partner

Sarah Nicholl
Venture Partner

 Frequently Asked Questions

  • Capital Circle is a private, invitation-only investment experience. Over the course of four days in Key West, select investors and their partners connect with fund managers and founders in an environment designed for authentic relationship building—far from the formality of boardrooms and pitch decks.

  • Every detail—from luxury accommodations and private transfers to chef-prepared meals, curated excursions, and exclusive entertainment—is arranged for you. The goal is to allow you to focus entirely on the people you’re meeting and the opportunities being shared.

  • Yes. All attendees must be accredited or qualified investors and capable of making $1M–$5M investments. This ensures the group is well-aligned in both capacity and intent, creating a focused and productive environment for all participants.

  • Both. Mornings and select mealtimes may feature presentations and discussions with fund managers. Afternoons and evenings are designed for unforgettable experiences—whether it’s sailing on a private yacht, deep-sea fishing, or enjoying a white party under the stars.

  • Each edition of Capital Circle features a small, carefully curated group of up to 15 investors and their partners. For this Key West gathering, we are spotlighting Siol Capital, a venture capital firm with a focus on transformative technologies. Attendees are seasoned investors, typically writing $1M–$5M checks, and share an appreciation for both high-quality deal flow and high-quality experiences.

  • Yes. This gathering will feature Síol Venture Capital and its Managing Partner, Michael O’Brien, alongside other presenting fund managers and founders. While the environment is relaxed and relationship-focused, there will be structured opportunities to hear concise, high-impact pitches. These sessions are designed to provide clarity and insight into each opportunity without the pressure of a formal pitch room.

  • Absolutely. In fact, we encourage it. Having your partner alongside you not only enhances the experience but also ensures you can make important decisions together, in an environment that feels as personal as it does professional.

  • Capital Circle coordinates travel through our partner, Delta Airlines, ensuring a seamless journey to and from Key West. We will make every effort to accommodate special requests and preferences, so your travel experience matches the elegance and ease of the event itself.

Located just a mile from downtown Key West in a private, upscale villa —an oasis designed for relaxation and dialogue.

Located in Key West, Florida

 

Five-Day Immersive Package

$2,500 for Individuals.
$3,500 for Couples.

Limited to 15. Reserve Your Spot Now.
Includes Fishing Charter Excursion and Saturday Night VIP Party.

Saturday Night VIP Party

$500 for Individuals.
$750 for Couples.

Limited to 30. Purchase Your Ticket Now.

Friday Fishing Charter Excursion

$500 for Individuals.
$750 for Couples.

Limited to 10. Purchase Your Ticket Now.