Justin
Sherlock

There is a specific kind of professional frustration that comes from watching a problem sit unsolved for years while everyone around you shrugs. Justin Sherlock spent five years at Flexport watching it happen. Companies shipping goods internationally were routinely leaving duty refunds unclaimed - legal money owed back to them by U.S. Customs - because the process to recover it was so convoluted, so paper-intensive, and so slow that most importers simply gave up. The brokers who could help charged a premium. The timeline stretched 6 to 12 months. The average importer had no visibility into what they were owed.

Sherlock noticed. Then he left Flexport in late 2023 and started Caspian.

Before writing a line of code or pitching a single investor, he did something unusual: he sat for the Licensed Customs Broker exam. It is one of the harder credentials in U.S. trade law - only a fraction of candidates pass each cycle, and fewer than 12,000 people hold it in the country. Sherlock passed it. The credential is not a marketing detail. It signals that he understood the problem well enough to master the legal and procedural framework governing it before building a business around automating that framework away.

That orientation - go deep before going fast - traces back to his academic formation. Sherlock graduated cum laude from Harvard with high honors in economics and a minor in Classics, then went to Wharton for his MBA. The combination is less surprising than it seems: rigorous quantitative analysis meets a habit of reading primary sources carefully. He spent two years as an investment banking analyst at Barclays in the Power and Utilities Group, moved to TA Associates for private equity exposure, and eventually found his way to Flexport - the logistics unicorn that was, at the time, reinventing freight forwarding from first principles.

At Flexport, Sherlock ran capital. He joined in April 2019 working in corporate development and investor relations, then moved into Flexport Capital - the company's trade finance arm. In three years as its Director and then Senior Director, he grew monthly revenues 10x while keeping the business profitable. He expanded the division to 20+ countries and managed a team of more than 20 direct reports across three continents. By the time he left in November 2023, Flexport Capital was a business that had crossed $1 billion in financing volume.

It was also the vantage point from which he saw duty drawback being systematically ignored. Importers paying duties on goods they later exported - or on goods manufactured with imported inputs - are legally eligible to claim back up to 99% of those duties. The mechanism is called duty drawback, and the U.S. Customs and Border Protection has administered it since 1789. In theory, it is one of the oldest trade incentives on the books. In practice, most eligible companies never file. The documentation requirements are labyrinthine. The filing process requires cross-referencing import records, export records, manufacturing records, and inventory data - often from incompatible systems.

Caspian connects to more than 80 supply chain and ERP systems to assemble that data automatically. It analyzes shipment and inventory records to identify eligible refunds, builds the documentation package, and files directly with CBP as an ABI (Automated Broker Interface) software vendor - the same status held by the major customs brokerage firms. Claims that historically took 6 to 12 months are completed in weeks. The company's pitch to CFOs is direct: there is money you are owed, you are not getting it, and we can fix that without adding headcount.

Sherlock's career reads like someone who kept picking the harder problem. Investment banking at Barclays (Power and Utilities Group) taught him infrastructure and capital structures. Private equity at TA Associates taught him how to evaluate businesses at depth. On Deck gave him a taste of the startup ecosystem. Flexport put him at the center of the global logistics revolution happening in the 2019-2023 window.

The pivot from Flexport Capital to founding Caspian is the move that defines his professional identity: he saw a specific, solvable, high-value problem that incumbents were too slow or too comfortable to address properly. He spent a year learning the domain from the inside before building a product to disrupt it.