# Andrew Carricarte

> Andrew Carricarte is a Miami technology founder, investor and former U.S. Army captain whose career has moved from combat deployments to electronic records, maritime software and digital insurance. He founded IOS Health Systems and Tritan Software, helped build patented systems that keep data moving through intermittent connectivity, co-founded Olé Life, and now leads FourCastle Investments while serving on civic and nonprofit boards.

- **Role:** CEO of FourCastle Investments; President, CTO, co-founder and board member of Olé Life
- **Organizations:** FourCastle Investments, Olé Life, Tritan Software Corporation, IOS Health Systems, USA Medical Services, World Trade Center Miami, Haven of Hope International
- **Education:** Florida State University
- **Known for:** Completed combat deployments to Afghanistan and Iraq as a U.S. Army infantry officer and earned two Bronze Stars., Founded IOS Health Systems, whose software was used by more than 2,500 physicians before its 2014 acquisition by Intermedix., Founded Tritan Software, which supported more than 99 percent of the global cruise industry before its 2023 acquisition by Ideagen.

## Career timeline

- **2001** — Joined the U.S. Army.
- **2001-2005** — Served as an Army infantry officer, completed combat deployments to Afghanistan and Iraq, reached the rank of captain and received two Bronze Stars.
- **2005** — Left active military service and became Director of USA Medical Services at AMEDEX-BUPA.
- **2007** — Founded IOS Health Systems and Tritan Software Corporation.
- **2009** — IOS Health Systems reported 250 percent first-quarter growth and service to 358 physicians.
- **2014** — IOS Health Systems, whose clinical software was used by more than 2,500 physicians, was acquired by Intermedix.
- **2017-2020** — Received U.S. patents with collaborators for systems that synchronize local and remote data during communication disruptions.
- **2021** — Became board chair of Haven of Hope International.
- **2022** — Joined the board of World Trade Center Miami.
- **2023** — Tritan Software was acquired by Ideagen.
- **2024** — A further Tritan patent application covering coordination between vessels and shoreside providers was published; FourCastle Investments was formed in Florida.
- **2025** — Olé Life, where Carricarte is a co-founder and board member, raised a $13 million Series B led by PayPal Ventures.

## Achievements

- Completed combat deployments to Afghanistan and Iraq as a U.S. Army infantry officer and earned two Bronze Stars.
- Founded IOS Health Systems, whose software was used by more than 2,500 physicians before its 2014 acquisition by Intermedix.
- Founded Tritan Software, which supported more than 99 percent of the global cruise industry before its 2023 acquisition by Ideagen.
- Named as an inventor on U.S. and European patent filings involving data access, replication and synchronization during intermittent connectivity.
- Recognized for six consecutive years as a South Florida Business Journal Power Leader in healthcare and named among the Miami Herald's Top 20 business leaders.
- Co-founded Olé Life, which reported more than $2 billion in insured value and over 4,000 distribution partners around its 2025 Series B.

## Latest updates

- **2025-07** — Joined a Haven of Hope International visit to Bolivia with his four children as part of his continuing role as board chair.
- **2025-01** — Olé Life announced a $13 million Series B led by PayPal Ventures, with participation from Mundi Ventures, AV8 and Advent Morro.
- **2024-11** — FourCastle Investments was registered in Florida, with Carricarte listed as manager.
- **2024-07** — A Tritan Software patent application naming Carricarte and Abel Almeida as inventors was published for coordinating vessel-to-shore referrals and data exchange.

## Links

- Website: https://olelife.com
- LinkedIn: https://www.linkedin.com/in/andrewcarricarte
- Twitter/X: https://twitter.com/andrwcarricarte
- Facebook: https://www.facebook.com/OleLife

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Profile page: https://yespress.io/andrew-carricarte
Published by YesPress — https://yespress.io
Last updated: 2026-09-27