• Cole Shephard


  • Rich Holman

    Founder & Director of Client Relations

  • Eric Berman

    Chief Investment Officer

  • Leonardo Sanchez

    Chief Financial Officer

  • Adam Jason

    General Counsel

  • Monica Quintero

    Chief Operations Officer

  • Jason Bennett

    Chief Marketing Officer

  • Adrian Beales

    Director of Sales

  • Jorge Calderon

    Director of Operations

Cole Shephard


Cole Shephard is the President of Lifeafar. Cole leads development and execution of the short and long-term strategic company goals while providing strong leadership throughout the organization. Cole has a wealth of valuable international experience and has overseen deals exceeding $1B USD.

Cole joined Lifeafar in 2018, arriving from Legacy Group Asset Management (Legacy), of which he still serves as Director. The South American company specializes in the international trade of agricultural products and structuring of private equity investments in the agricultural space with a core focus on Colombian markets.

Prior to forming Legacy in early 2015, Cole was with PricewaterhouseCoopers and specialized in accounting, advisory, and consulting solutions. During eight years with PwC he was stationed in the U.S., Bermuda, Hong Kong SAR, and Beijing. In the first of two stops he focused on accounting and advisory services to clients in a wide-range of industries, including oil extraction and distribution, healthcare, banking and biotechnology. Then during nearly four years in Asia he provided advisory and consulting services to clients participating in global mergers and acquisitions. Cole further concentrated on the financial services and real estate sectors, spending a majority of his time advising on cross-border deals in areas of business strategy review, business valuation, buyer and seller due diligence, tax structuring, and business carve-out analyses.

A native of Raleigh, North Carolina, Cole graduated Valedictorian from North Carolina State University in 2006 with a Bachelor’s degree in accounting and finance. He earned a Master’s degree in accounting the following year and became a licensed United States Certified Public Accountant in 2008.

Rich Holman

Founder & Director of Client Relations

Rich Holman is the Founder & Director of Client Relations of Lifeafar. With about five decades of experience across the real estate, mortgage, securities and investment banking industries, he is the on-the-ground resource in Colombia and Puerto Rico for many of Lifeafar’s key Latin American real estate and investment initiatives, and he oversees the maintenance and development of key investor and business relationships.

A proud Texan, Rich began traveling to Medellín, Colombia in 2006 and quickly realized it was one of the world’s best-kept secrets. He believes the city is one of the world’s best places to live and work, and is one of most-undervalued real estate markets worldwide.

Seeing the potential, Rich launched Lifeafar Medellín in 2007, and later merged it with The Apartment Medellín in 2012. Rebranded as Lifeafar, under Rich’s watch the company expanded to other major cities in Colombia. In 2018, the company started offering investment products in Puerto Rico and rebranded as Lifeafar, becoming the go-to resource for people longing to live, travel and invest in a “Life Afar.”

Prior to launching the company, Rich enjoyed a diverse business career in the United States, including work in tech, real estate, mortgage banking, securities, publishing, and investment banking. After leaving the Air Force as a Captain in 1970, he worked for a boutique high-tech firm in Boston, where he was the first to sell and place an automatic test system for printed circuit boards within all four branches of the military, NASA and private industry.

Based in Atlanta in the late 1970s and early 1980s, Rich hired, developed and managed the then-largest sales force under one roof for the sale and retail distribution of municipal bonds, and also helped pioneer shared equity financing to fund residential real estate when interest rates were at record levels.

In the early 1990s, while working for USF&G, Rich spearheaded development of a family of mutual funds. Later in the decade, he helped found, privately fund and, as President and Editor-in-Chief, operate Lottoworld, which went public on the NASDAQ. Finally, prior to relocating to Medellín, Rich was a top mortgage broker for Market Street Mortgage, a leading FHA loan provider in southwest Florida.

Rich holds a degree in chemical engineering management from the University of Texas, as well as an MBA from Ohio State University. Feeling right at home in Medellín’s perfect climate, Rich enjoys spending his downtime dining at the best restaurants in Medellín’s emerging cuisine scene, hitting the gym regularly, and vacationing in Latin American cities, especially throughout Colombia.

Eric Berman

Chief Investment Officer

Eric Berman is the Chief Investment Officer of Lifeafar. He oversees investment strategy including acquisitions and development, and plays a key role in leading Lifeafar’s hospitality initiatives.

Eric has spent his career working with a diverse base of investors, owners, lenders and developers of hotel and mixed-use real estate assets. Along the way, he has advised on more than $2 billion of hotel and real estate transactions throughout the U.S. and Latin America. The experiences Eric brings to Lifeafar will be instrumental in the continued success and global expansion of the company.

Eric joined Lifeafar in 2018 following four-plus years with Berkeley Research Group, where he helped pioneer the firm’s hospitality advisory group and expand its corporate finance efforts in Latin America. He began his career at Deloitte & Touche, LLP, where he provided accounting and advisory services for clients in the financial services, banking, real estate and retail industries, focusing on companies with an aggregate of more than $180 billion in assets and over $10 billion in annual revenues. During his professional career, he has held positions in destinations including New York and Miami, as well as Colombia, Panama, and Mexico.

Born and raised in Philadelphia, PA, Eric was educated at Penn State University – Smeal College of Business, where he earned a bachelor’s degree and a master’s degree in accounting. He has been a licensed Certified Public Accountant since 2013 and holds a certificate in hotel real estate investment and asset management from Cornell University.

Leonardo Sanchez

Chief Financial Officer

Leonardo Sanchez is the Chief Financial Officer for Lifeafar, leading all financial initiatives including budget management, cost-benefit analysis, and forecasting. 

Prior to joining Lifeafar,, Leonardo spent more than 20 years working for multinational companies including Siemens, Fox Networks Group, and First Data. While at Siemens, Leonardo spearheaded the implementation of the first electronic marketplace for the Power Generation segment of the company’s operations in Latin America, which drove an incremental $6M USD in annual revenue. His career includes tenures in Thailand and Germany, and he brings comprehensive expertise in financial management and reporting, budget management, forecasting, business intelligence, risk management, SOX Compliance, IFRS, and USGAAP. 

Born and raised in Bogotá, Colombia, Leonardo earned a Bachelor’s degree in Industrial Engineering from Universidad de America, a Master’s degree in Finance from Universidad del Rosario and a Master’s degree in e-Commerce from Dalhousie University in Halifax, Canada.

Adam Jason

General Counsel

Adam Jason is the General Counsel of Lifeafar and oversees the firm’s legal division and advises the company on its international legal compliance and investment product offerings.

Adam joined Lifeafar in 2017 after eight years practicing law in the United States. He specializes in corporate finance, corporate governance, securities regulation and international business transactions, having advised companies and investment banks on offerings of debt and equity securities exceeding an aggregate of $10 billion. After graduating from law school, Adam worked for two international law firms, Jones Day and then Vinson & Elkins LLP. He has advised the world’s leading investment banks, including, among others, JP Morgan, Morgan Stanley, Citibank and Goldman Sachs. Adam has also served as outside counsel for some of the world’s most recognizable brands, such as The Sherwin-Williams Company, R.J. Reynolds Tobacco, Procter & Gamble and Macy’s.

Originally from Buffalo, New York, Adam has a Bachelor’s Degree from Ithaca College, and a Juris Doctorate from New York Law School, where he graduated magna cum laude, served as an editor for the New York Law School Law Review and, for two years, interned with The Honorable Paul A. Crotty, United States District Court Judge for the Southern District of New York.

Monica Quintero

Chief Operations Officer

Monica is the Chief Operations Officer for Lifeafar. She brings over seven years of professional experience in finance and corporate consulting to the company. Her background includes advising more than 30 companies and extensively collaborating with local chambers of commerce as well as the regional government of Antioquia.

Born and raised in Medellín, Monica studied engineering administration with a concentration in corporate finance. She later learned English in London, which cultivated an interest in working internationally with people from a variety of cultures. Monica also advises Lifeafar on business strategy and development.

Jason Bennett

Chief Marketing Officer

Jason Bennett is the Chief Marketing Officer of Lifeafar. He leads all marketing initiatives including global brand strategy, advertising, customer acquisition and retention, partnerships, collaborations, property launches, and social media.

Jason brings more than 15 years of experience leading Fortune 500 brands to his role, including senior executive positions at Gap Inc., where he was responsible for nearly $1 billion in annual sales for the Banana Republic brand. Among notable achievements during his Gap Inc. career, Jason pioneered numerous successful and innovative global marketing campaigns, consumer relationship management (CRM) initiatives, loyalty programs, print and digital strategies, product launches, and partnerships – consistently beating critical key performance indicator (KPI) benchmarks along the way.

After departing Gap Inc. in 2015, Jason founded True Star Consulting and led strategy, creative development, customer experience, and media planning for brands across multiple industries, including retail, food and beverage, entertainment, finance, health and wellness, transportation, technology, and real estate. True Star took Jason around the world, and during his travels he fell for the city of Medellín and the people of Colombia. Inspired by his experience of purchasing a home in his newly adopted city, Jason joined the Lifeafar team and looks forward to empowering other travelers to fall in love with the South American city.

Born and raised in the San Francisco Bay Area, Jason holds a Bachelor of Science degree in business administration from the University of Oregon.

Adrian Beales

Director of Sales

Adrian Beales is the Director of Sales of Lifeafar. He leads Sales, Capital-Raising and Events Divisions, and aids customers in identifying appropriate investment opportunities for their portfolios in Latin America. Since joining Lifeafar in 2017, he has nurtured deep-rooted relationships with the firm’s investors, and has a reputation for putting clients first in all transactions.

Prior to assuming the role of Director of Sales, Adrian served as Investment Funding Manager at Lifeafar, providing prospective clients with experience, expertise and local access to invest in major real estate and agricultural projects in Colombia and Puerto Rico. Adrian has personally invested in real estate since his early twenties, buying multiple investment properties in his home state of Victoria, Australia. Now living in Colombia, Adrian has made investments in Latin America, and is continuing his search for investment opportunities that deliver exceptional returns to his clients as well as allow him to earn passive income and live a life of his choosing.

His previous professional experience includes working as a Relationship Director – Enterprise (Large Law) with LexisNexis in Sydney, Australia where he worked with the top global law firms with an Asian-Pacific focus. He got his start in sales working with various organizations in Melbourne, Australia, including, Telstra, The Kangan Institute and Asahi Beverages.

Born and raised in Kinglake, Australia, Adrian has studied and earned multiple degrees from institutes of higher education in Australia, Canada, France and the U.S., including a Bachelor’s and two Master’s degrees in business, commerce and leadership. He completed his most recent Master of Science in leadership at Northeastern University in Boston, Massachusetts.

Jorge Calderon

Director of Operations

Jorge Calderon is the Director of Operations for Lifeafar, and he is responsible for the operation of the current portfolio of properties under management.

With over 30 years of experience leading such esteemed hospitality brands as InterContinental, Crowne Plaza, Marriott, and Wyndham, Jorge has an unrivaled passion for customer service and directing high performing teams. His properties have been nominated for and won numerous awards including TripAdvisor’s Exceptional Service and Top Hotels, and he collectively has overseen 3,000+ rooms, 1,000+ employees, and tens of millions in revenue. Jorge has also led the development over 20 successful hotel and restaurant concepts.

Born in Mexico City, Jorge has a Bachelor’s degree in Culinary Arts, and he has applied his expertise to such in-demand destinations in Mexico as Cancún, Cozumel, Cabo San Lucas, Puerto Vallarta, and Huatulco. He has also worked abroad in Israel, Panama, Honduras, and Colombia.