Sherpa cofounder and CEO Max Tremaine built his company around a problem most travelers only notice at the worst possible moment - the days-before departure scramble of figuring out what documents you actually need to cross a border. Max and his cofounder Ivan had lived it firsthand: inconsistent rules, unclear requirements, and the anxiety of realizing you might miss a trip because you weren’t prepared.
From that pain point, Sherpa became a set of tools used across the travel ecosystem (airlines, online travel agencies, corporate travel managers) to translate border requirements into simple guidance, help travelers apply for eVisas inside the booking flow, and validate documentation so carriers reduce disruption at check-in and boarding. The key was building a scalable tech company in a space dominated by service providers - and solving a problem that couldn’t be replicated in a weekend due to regulatory complexity and constant policy change.
A major inflection point came during the pandemic. Instead of stepping back when travel collapsed, Sherpa leaned into its mission - “make it easy to cross borders” - by redirecting its systems toward health requirements. It wasn’t a clean revenue opportunity, but it was a chance to build goodwill and name recognition when the industry urgently needed clarity. That bet paid off: Sherpa scaled from a handful of airline integrations to dozens over the following period.
Max also shares unusually grounded advice for founders: treat your financial model as a real management document, prioritize investor alignment, and don’t believe the myth that hiring lots of people creates rapid output. The biggest leaps tend to come from a small number of highly capable owners with the infrastructure to move independently.
Finally, we explore how AI is changing Sherpa’s operations. Max describes LLMs as “the world’s most energetic intern” - powerful for speed, assessment, and drafting - while still requiring human judgment for architecture and trade-offs. In Sherpa’s case, AI helped reduce response time to government system changes from weeks to, in some cases, hours.
