Entrepreneur Brian York Was Born to Go the Distance in the Startup World

Brian York has been overcoming adversity since he was born... literally.

Born in the streets of Bogotá to a homeless mother who gave him up to an orphanage for a chance at a more promising future, York has been consciously -- and unconsciously -- trying out his luck his entire life.

York grew up in Boston and began his professional career in Silicon Valley, where he became a tech entrepreneur working with the city’s hottest VC’s. But a strong desire to go back to his roots led York to Bogotá in 2017 where he founded his most successful startup to date, Liftit.

York now spends his time working on Cubbo, an e-commerce fulfillment startup that he co-founded as a result of the pandemic’s indirect effects. Combined, these two companies have raised over $42 million.

The Org had the opportunity to catch up with York and learn about his background and the timely decisions that led him to become an entrepreneur in one of the hottest investment markets in the world, Latin America.

At just 14, York launched a landscaping business with a close friend that initially offered lawn mowing and leaf raking services. The duo quickly expanded when they turned 16 and were able to operate heavy machinery and drive a truck. Once in college they oversaw the business remotely and eventually sold it to another friend.

York went on to study accounting and wasted no time getting into business. He created an on-demand CFO business for Venture Capital firms and with some luck and good timing he became the CFO to Chris Sacca at Lowercase Ventures -- one of the first investors in now giants Uber and Instagram.

Win big… or lose big

Getting first-hand exposure to tech startups and their potential, York pivoted to tech entrepreneurship and created Enthuse, a social network for sports fans. York raised a $3 million seed round to get his idea off the ground only to fail spectacularly two years later. The idea never found product market fit, but, as York mentions, he found out he was indeed really good at fundraising -- a skill he is very well known for now.

York highlights that he grew up playing poker, a game that has proven to be very relevant throughout his career. Continuously “going all in” at his multiple startups by betting on himself, both personally and financially, he has understood he will either “lose big, or win big” and that has been a crucial aspect in his entrepreneurial journey.

Clearly York is not risk averse, a quality he attributes to “being one of the only ‘brown’ kids in his town.” It wasn’t about discrimination, but the fact he felt different was enough to drive him to take the extra ten steps needed to fit in.

After getting over his first failure and looking to blow off some steam, York embarked on a trip to Vegas where he serendipitously came across his next business. A close friend who was the head of mobile at Caesars Corporation told York they were building several apps for the large conglomerate. They hired multiple companies who were quite good at frontend development, but none seemed to understand the backend. Not one to miss out on a business opportunity, York committed to figuring out a way to connect all the applications’ backends and created a mobile backend as a service. In a span of just 24 months, York created the company and made his first exit.

Returning to the roots

Living a gypsy lifestyle is something York is proud of and thrives on. He loves change, new countries, meeting new people and all the challenging feelings that come with different environments. In fact, since he was 17 he has never lived under the same roof for more than one year.

Continuing with this trend and still fueled by the desire to learn more about his roots, York went to Colombia in 2017 with the idea of connecting truck drivers to shippers. Knowing no one in the country and eager to launch his idea, he backed the startup with $100,000 of his personal funds and set out to fundraise. He looked for investors on LinkedIn and began meeting as many people as possible.

York says that one of the most effective strategies he has implemented throughout his career is consistently following up with every person he meets. Quick emails with specific requests, such as key introductions, helped him get Liftit and many other things off the ground.

Today, Liftit provides immediate cargo delivery via a platform that connects cargo transportation providers with companies who need this service. Via its marketplace, drivers are paired with companies looking to complete a delivery. The platform uses technology to optimize routes, measure and analyze delivery efficiency, monitor cargo and solve problems in the logistics industry.

In July 2020, during the pandemic shipping boom, York facilitated a $22.5 million Series B round, bringing Liftit’s total funding to $39 milllion.

Getting closer to the goal

Just a couple months later in November 2020, York transitioned out of Liftit and is now focused on building Cubbo, a Latin American technology company that fulfills e-commerce orders for direct-to-consumer brands. Cubbo is building the largest urban warehouse fulfillment network throughout LatAm, which enables it to be the only solution in the region to do same-day fulfillment. The strategy for urban fulfillment is repurposing real estate assets (unused brick-and-mortar outlets or abandoned strip malls) and turning them into spaces suited for new industries.

Operating in Bogotá and Mexico City, Cubbo has raised $3 million Pre Seed.

Cubbo is York’s fifth venture-backed startup. Although wildly successful in the eyes of many, he is optimistic and hopeful for what the future holds.

A true entrepreneur, York finds it difficult to take a weekend off from work. He says “it’s the stress that he’s addicted to and right now is THE time to be an entrepreneur in LatAm,” so there are no signs of stopping for him any time soon.

Much like his commitment to startups, which never have an easy or straight path, York is into long distance running. He says he reaches “a meditative state and forces the body into a runners high” where he is eventually able to think of nothing and enter a state of flow.

In an odd parallel to entrepreneurship he says his experience running ultra marathons induces mental pain similar to the tactics one goes through in startups. “The journey looks like there’s a ton of fog and way too much terrain to cover, but you eventually clear up and realize you are making progress and getting closer to the goal.”