Delivering Latin America: What A.J. Hernandez Learned Building SkyPostal

A.J. Hernandez never planned to run a logistics empire. He was a left-handed hitter, playing first base and outfield in the California Angels system, chasing a dream that ended at 25. That is when he walked into his father’s courier company, Skynet, and started at the bottom. Thirty-three years later he is president and CEO of SkyPostal, which the episode describes as the largest private mail and parcel delivery network in Latin America, covering more than 30 countries. Along the way he helped invent cross-border ecommerce for an entire continent. In this episode, he tells Timur the family story behind the business, how SkyPostal survived 2008 and COVID, and what US sellers get wrong about shipping into Latin America.

From the baseball diamond to the family business

Hernandez credits baseball for his management style. Playing taught him people skills, leadership, and how to win and lose with grace. A manager talking to players is not so different from a CEO talking to his team. What worked in the clubhouse worked in the warehouse. The family backstory is the heart of the episode. His father’s family left Cuba in 1958, before Castro. He grew up in the projects of New York City and started as a foot messenger at a company called Choice when he was 16. Nineteen years later he bought Choice’s international division and built it into Skynet, which Hernandez describes as the largest privately owned courier network in the world, with coverage in more than 120 countries. The elder Hernandez passed away two years ago, but his lessons shape the company still: hard work, persistence, people as the core of the business, and a deliberate balance between work and life.

SkyBox: the first US shopping address for Latin America

The idea for SkyBox arrived in 1993 from an unlikely place: golf. His father’s Peruvian business partner played golf and wanted to buy equipment from the US, but USPS would not accept the heavy boxes. He asked whether Skynet could receive the shipment at its US office and hand-carry it to Peru on a regular flight. They could, and people started asking for the service. SkyBox gave Latin American shoppers a US address, bought or received their goods, and delivered them to their door. They launched in Argentina and mailed catalogs from Lands’ End, J.Crew, L.L. Bean, Victoria’s Secret, and Sears. One of the first customers was an American Express executive living in Argentina, which led to Amex offering SkyBox as a card benefit. Hernandez says about 8,000 people signed up the first night they announced it. Within a year the service was in 30 banks’ card programs, and eventually SkyBox grew to more than 300,000 clients. They spun it off in 1996 and sold it to Lan Chile, now LATAM, in 2000.

SkyPostal: from mail to parcels

In 2001, with a $600,000 loan from Lan Chile that Hernandez says they begged, borrowed, and stole for, he founded SkyPostal. The timing was strategic. The European postal administrations were privatizing, which freed them from Universal Postal Union restrictions on handling mail outside their borders. SkyPostal became the delivery network in Latin America for European mail. Then 2008 hit twice. The financial crisis arrived, and print collapsed: PC Magazine and the Harvard Business Review went digital, and nobody needed to ship printed matter anymore. SkyPostal reinvented itself with Punto Mio, a package-forwarding service for online shoppers. The non-compete from the SkyBox sale had expired, so banks came back: 30 banks including American Express offered Punto Mio, and it grew past 500,000 clients. The real pivot came from Endicia, the shipping label company later acquired by Stamps.com. Endicia had terrible delivery problems in Brazil using USPS and asked SkyPostal for help. Hernandez built a full tracking system for parcels, and Endicia Global Services made SkyPostal its first provider. That was the moment the business flipped from consumer-facing, the buyer, to shipper-facing, the seller and retailer. By 2025, Hernandez says Punto Mio was under 10 percent of the business, mail under 5 percent, and parcels made up the rest. Big clients include Amazon, eBay, Temu, and Shein.

COVID nearly killed it, then made it

Hernandez is blunt about the pandemic: they almost did not make it. The shutdown was brutal, and they took EIDL loans to survive. Then the same Asian marketplaces that everyone else was watching, Temu and Shein, exploded into Latin America. Online shopping took off across the region, and 2020 became SkyPostal’s best year ever. They have been on that ecommerce wave since.

Latin America is not one market

The core lesson of the episode is that Latin America is not a single market, and sellers who treat it like one will pay for it. Each country has its own customs rules, tax thresholds, delivery expectations, and culture. Brazil wants home delivery. In Central America and the Caribbean, local pickup is culturally normal, much like US PO boxes. There is no cash on delivery anywhere, for security reasons. WhatsApp is the communication tool customers actually use, not email. Hernandez’s rules of thumb: sellers need a local partner with local knowledge and boots on the ground in every country. His advice on Venezuela is memorable: “Don’t do Venezuela.” It was SkyPostal’s number one market in 1995; after Chavez it went to zero. His broader advice is to be a regional player, not a country-specific one, because a single country can turn on you. He calls the region the “wild west” of ecommerce, and says the opportunity is still early: Latin American ecommerce is in the second or third inning, with a growing middle class shopping on mobile.

How US sellers should start

When Timur asks which countries US sellers should target first, Hernandez names Brazil, Mexico, Colombia, Peru, Ecuador, and Argentina, which recently reopened after years of restrictions. His advice for a new seller is to test the water: start with the biggest markets, learn how they behave, and scale from there. Shoppers’ expectations are rising fast. They see Amazon-speed delivery in the US and are starting to demand it at home, so speed is becoming a competitive advantage. What should a seller look for in a logistics partner? Hernandez lists four things: rates, local knowledge, local coverage, and customs relationships. SkyPostal puts country managers in each market who know the local officials and the delivery culture. He also points to the integration side: SkyPostal offers a Shopify app and works with ShipStation and EasyShip, because sellers want to plug in and ship.

Technology is half the delivery business

Hernandez calls SkyPostal as much a technology company as a delivery company. The 16-person IT team builds everything in-house. The reason is simple: in this business, data is the delivery. “If the client doesn’t see that it’s delivered, it wasn’t delivered,” he says. Tracking is the product. The company pre-clears parcels into countries so customs does not become a black box, and the whole chain, from label to doorstep, is visible to the shipper. Looking ahead, he expects faster delivery across Latin America as middle-class consumers with phones demand Amazon-style service. SkyPostal’s formula is to be cheaper, faster, and better than the alternatives: the national posts, which he calls horrible in much of the region, and the express carriers like DHL and FedEx, which are reliable but expensive. SkyPostal wants the middle: courier bells and whistles at near-postal prices.

A family business that lasts

The episode closes on the family. Hernandez’s brother Andy works in the business, as does his wife Patty, a former American Express marketing executive he met in 1996. He describes the four “heads of state” who run the company with him: Patty, Andy, Diego Moreno who heads IT, and Ricardo Lowe, the CFO. His definition of success has three parts: never quitting, treating people well, and surrounding yourself with great people. It is the same philosophy his father preached from the foot-messenger days. Three decades after a baseball career ended, A.J. Hernandez is still playing the long game.

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This post is based on the Logistics Remix episode “Delivering Latin America” with A.J. Hernandez, President and CEO of SkyPostal. The views are the guest’s and the host’s own.