Building A Marketplace In A Traditional Industry Takes More Than Tech

This voice experience is generated by AI. Learn more.This voice experience is generated by AI. Learn more.Justin Crabbe, Founder and CEO of Jettly.

gettyWhen I was learning to fly, looking out from the cockpit offered a view of absolute precision. Instruments, weather systems and flight paths were all part of a synchronized, data-driven environment. Yet, when I looked at the business side of private aviation, I saw a striking disconnect. While the flight operations themselves were the pinnacle of efficiency, the supporting business processes, still reliant on manual phone calls, fragmented networks and analog quoting systems, seemed to be operating in a different era.

This realization shaped my perspective as an entrepreneur. The biggest mistake I see tech founders make when building marketplaces for legacy sectors is assuming that traditional industries simply need “slicker software.” But technology rarely transforms traditional industries on its own. In my experience, true innovation requires industry expertise, operational credibility and a deep understanding of the domain.

When I set out to build an aviation marketplace, I approached it not just as a technology founder, but as a commercial pilot who understood the operational reality behind every flight. Seeing both sides taught me that modernizing a high-stakes, traditional market means using technology to elevate the industry’s standards for transparency, efficiency and trust.

Building a two-sided marketplace in a specialized sector inherently presents a severe “chicken-and-egg” dilemma: Aircraft operators will not list their fleet without consistent traveler demand, and travelers will not adopt a new platform without comprehensive fleet availability. In my early days as a single-person bootstrapped operation, overcoming this hurdle required relentless manual effort. Beyond liquidity, navigating the heavy regulatory “red tape” of international and Canadian aviation compliance posed an immense structural barrier.

Scaling from those initial manual workflows taught me an important lesson: Technology alone cannot bypass regulatory and network complexities. Instead, you need to engineer your marketplace specifically to respect and streamline them.

Popular media and social platforms often depict private aviation through a lens of champagne, red carpets and luxury novelties. But in my experience, active flyers are not buying the bells and whistles. Private aviation is about precision, predictable scheduling and time.

A corporate executive or legal team booking a trip isn’t seeking glamour; they are buying productivity. When a business team can visit three client sites across different cities in a single day and return home that night without commercial airport delays, the economics of time savings become obvious. That’s why it’s important for marketplace platforms to focus on removing transactional friction and delivering precision rather than selling surface-level luxury.

Every marketplace depends on trust, but in high-stakes environments involving safety, complex logistics and major financial commitments, trust becomes a primary currency. A charter quote is never just a simple price point; it depends on aircraft positioning, crew duty times, maintenance windows, airport logistics and weather patterns.

Attempting to digitize an industry without factoring in operational variables typically leads to fragile software that breaks when real-world complexity hits. A marketplace model shouldn’t aim to eliminate human expertise or industry professionals. Instead, use technology to eliminate administrative friction so experts can focus on safety, execution and client relationships.

Traditional industries that have operated in similar ways for decades do not transform overnight. For founders entering complex sectors, it’s important to balance technological innovation with deep industry respect, regulatory patience and consistent relationship-building. Instead of attempting to replace industry veterans or side-stepping operational realities, seek to understand the work deeply enough to turn the underlying complexity into a seamless, trusted user experience.​

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