Gen Xer left San Francisco for Medellín, Colombia, founded 2 startups

• Jason Bennett, 46, moved from San Francisco to Medellín, Colombia in 2018.
• Bennett left his job at Banana Republic to go abroad and start two startups.
• He said Medellín offers a better quality of life than San Francisco and is cheaper.

Jason Bennett made a career in San Francisco, but saw no future for himself in the corporate world.

Bennett, 46, worked as a senior marketing director at Banana Republic. He earned a good salary and received great bonuses, but he felt unfulfilled.

“I started to feel disconnected from both my job and the city,” Bennett said. “I started to wonder if I really wanted to spend the rest of my life in an office working for other people.”

In 2015, Bennett left his job at Banana Republic and founded True Star Consulting, a marketing firm specializing in… strategic planning and creative direction for brands. He said he has saved enough for the future and at the age of 37 he is ready to start a new adventure.

During this time, Bennett moved to Lisbon and started True Star Consulting as a digital nomad. In 2016, he visited Medellín, Colombia and said he envisioned it as his future home. He moved there two years later.

While many Americans retire abroad, Bennett is among those working and looking for a career outside the United States. There were 429,674 U.S. citizens living in South and Central America and the Caribbean in 2022, up from 374,241 in 2012, according to the Federal Voting Assistance Program, which helps foreign citizens vote in U.S. elections.

“It was one of, if not the best, decisions I have ever made,” Bennett said.
“I always felt at home.”

Building financial independence started at a young age

Bennett was born and raised in San Francisco. In 2000, he earned a bachelor’s degree in business administration from the University of Oregon.

After college, Bennett worked in marketing at department store Mervyn’s before joining Banana Republic in 2004. Over the next decade, Bennett rose through the corporate ranks, becoming chief marketing officer in 2013 and a senior executive shortly thereafter.

Although Bennett enjoyed his job, he stated that he was not satisfied with his day job. He wanted to take ownership of his schedule and career development.

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“Ultimately, I wanted to be my own boss,” he said.

Bennett said the prospect of leaving his job at Banana Republic seemed reasonable because he had been actively saving and taking care of his finances.

“Very early on, my grandparents told me to max out my 401(k) and then go have fun, and that’s what I did,” Bennett said. “The lesson on compound interest should be topic #1 for anyone thinking about forging their own path one day.”

In 2012, while still living in San Francisco, he purchased a 700-square-foot, one-bedroom apartment for just under $400,000. Bennett said he chose the 15-year mortgage to accelerate his home equity and provide a lower interest rate.

Bennett also increased his wealth by investing in stocks, index funds and fixed-income securities such as certificates of deposit. He has been keeping detailed track of his finances since 1995, when he was 17.

Bennett said he felt confident in quitting his own job to earn a fraction of the salary at his own company, and he felt confident in moving abroad. He refused to share information about his company’s revenues.

“I didn’t know I was going to do this at 25,” Bennett said. “But I knew it was important to save.”

Life in Medellín compared to San Francisco

Bennett said life in Medellín is amazing, from the weather to the culture and food.

He said his cost of living is much lower than San Francisco. For example, he said he could eat a “perfect meal” for less than $10 and a cup of “the best coffee in the world” for less than $2. He also said public transportation and Uber are affordable

Bennett is single and has no children, which also keeps his daily costs down.

Medellín fascinates him so much that he founded a travel company, The Paisa Plan, to help people plan their visits to Colombia and the city. However, Bennett declined to share information about his company’s revenue.

As a volunteer, he also provides marketing strategy services for the Medellín Philharmonic Orchestra.

“It reflects my love, respect and appreciation for my adopted home and aims to help visitors truly discover the magic of Medellín,” he said.

He said he is still smart about saving, despite the lower cost of living.

After six years of living in Medellín, Bennett said he has a better work-life balance than he ever did in San Francisco. He also added that the city is full of energy.

“I also take every opportunity to explore the city and immerse myself in what it has to offer,” he said. “There are so many great restaurants and cafes. More stunning parks than you can count. And there’s always something cultural going on.”

Are you an American who moved abroad for work? This reporter wants to hear your story. Please contact me at: [email protected]