The people behind San Juan Capital

Dillon Bracken

Chief Executive Officer

Dillon Bracken is a real estate investor, and technologist who has spent nearly two decades building at the intersection of property and software.

With his wife Venza, he owns Paragon Properties, which operates high-end luxury properties in Puerto Rico and on the mainland. A mathematician and computer scientist by training, Dillon built the AI infrastructure that runs the entire operation — sourcing, underwriting, property management, and opportunity analysis at a depth no conventional back office can match.

Dillon has invested in real estate since 2006 and specializes in deal structures built around Puerto Rico’s tax-credit programs. Beyond his portfolio, he serves on the board of Eyes Over Puerto Rico, a nonprofit providing free laser eye surgery to underserved Puerto Ricans. He also hosts charity events across the island and supports youth financial-literacy programs for Puerto Rican students.

Bob Olejar

Strategic Partner

Bob Olejar has spent more than three decades making companies famous.

In the 1990s he helped move the modeling and talent industries from paper to digital, building ModelWire, a platform used by agencies worldwide. He is named as an inventor on U.S. patent filings for data-distribution technology.

He went on to found Placement Directory, a strategic marketing and product-placement firm he led for more than twenty years, putting brands in front of audiences through television, film, music, sports, and celebrity culture. Across that period his companies worked with more than 2,000 brands.

The ones he draws on most weren’t famous when he got there. Quest Nutrition had two employees. Celsius was a few thousand dollars of product and a used truck. Building belief in a company nobody has heard of is a different discipline than promoting one that already has a name — and it is exactly the discipline a public offering demands.

Today he is founder and CEO of Clout Hero.

Daven Michaels

Executive Chairman

Daven Michaels is a New York Times bestselling author of 10 books, a 30-year CEO, and one of the most connected figures in Puerto Rico’s business community. Over three decades he has built and led companies across outsourcing, publishing, media, and marketing — including 123Employee, one of the earliest offshore staffing firms to scale for the small-business market.

He is the author of more than ten books and has helped dozens of authors and executives reach bestseller lists.

Since relocating to Puerto Rico, Daven has become a central connector on the island. He founded San Juan Social, which has grown from an events community into a full media ecosystem — a monthly print magazine distributed island-wide, the San Juan Social Podcast, and an annual cruise that draws 550 of the island’s operators and executives. He also founded Eyes Over Puerto Rico, a 501(c)(3) that provides free vision-restoring surgery to Puerto Ricans who cannot afford it.

Daven has lived in Puerto Rico for nine years, and his audience across platforms exceeds 1.5 million. As Executive Chairman, he gives San Juan Capital’s clients his platform, his relationships, and the visibility to get their offering in front of investors.