A uniquely elite management team.

Island Paradise is led by a unique combination of experienced real estate investors and experts in Opportunity Zone and tax advantaged investing.

Robbie Crager


Robbie Crager has purchased and sold more than 2,500 commercial and residential properties in his career. He moved to Puerto Rico following Hurricane Maria and has purchased more than 50 properties on the island.

David Micale


David Micale is a serial entrepreneur who has successfully purchased, revived, and sold several businesses over the last three decades. Following the sale of a hardware store chain, Dave moved to Puerto Rico and partnered with Robbie.

Ashley Tison

Partner & General Counsel

Ashley is the founder of OZ Pros. He has extensive real estate experience, acting as general counsel to several firms and advising on document review, litigation support, business risk management, and operating contracts.

Ari Kresch

Managing Partner

Ari Kresch is the founder and CEO of 1-800-LAW-FIRM. He has invested in and developed real estate for more than 50 years. In 2016, he moved his family and his legal marketing business to Puerto Rico

Seth Rosenberg

Partner & CFO

Seth is the fifth generation providing insurance and financial planning solutions to businesses and individuals. He runs Ability First Financial, a specialty financial planning practice, licensed as a registered investment advisory firm, insurance agency, and plan administrator with the tagline Taxes are Overrated (TM).

Raj Gupta

Impact Prosperity Partners
Co-founder and Managing Partner

Raj is a full-time syndicator and asset manager, with extensive experience in multifamily, single family, mobile home parks, real estate development and ground-up construction. He brings years of experience in wealth management, estate planning and tax strategies.

Anna Simpson

Impact Prosperity Partners
Co-founder and Managing Partner

Anna is a full-time investor, syndicator and multifamily asset manager, with over 10 years of experience in real estate investments, sales, acquisitions, capital sourcing and project management. She is a principal owner and asset manager of over $175M in real estate assets.