Aaron Fessler

Some founders draw a product on a whiteboard and then go hunt for a customer. Aaron Fessler tends to work in the opposite order. He becomes the customer first - runs the messy, physical, weekend-rush version of the business - and only then builds the software that the mess demanded. It is a slower way to arrive at a product. It is also why the products keep working.

His current company, TripWorks, is a booking and operations platform for the tours, activities, and attractions business. That is a polite way of describing a corner of the economy that runs on long lines, printed waivers, seasonal chaos, and spreadsheets held together with hope. Fessler knows it intimately, because before he wrote a line of TripWorks he spent years standing inside exactly that world, feeling every gap in the tools available to him.

The origin

A barn attic in Ohio

The through-line of Fessler's career starts where a lot of American business stories start - with more idea than money. He launched his first company, The Allegro Group, from the attic of his family's barn in Ohio. There was no venture round waiting, no accelerator, no warm introductions. There was an attic and a bet.

The bet paid. Allegro grew, and in 1999 it was acquired by Mail.com, then trading on the Nasdaq under the fitting ticker MAIL, in a cash and stock deal worth about $40 million. It was the kind of outcome that could have ended a career comfortably. For Fessler it was closer to a first chapter.

The second act

Guarding Hollywood

In 2001 he started MediaSentry, and it landed him in an unlikely fight - the piracy wars of the early digital era. As broadband spread and file-sharing exploded, film studios and record labels watched their catalogs leak across the internet with no idea how to measure the damage, let alone stop it. MediaSentry became the largest provider of anti-piracy services for the motion picture and recording industries, and its client roster read like a studio lot map: Sony Pictures, Warner Bros., Fox, Disney, MGM.

The work was technical, adversarial, and constant - the internet's plumbing versus the entertainment industry's fear. It also put Fessler in rooms most founders never see: the general counsels and technology chiefs of studios that measured risk in franchises, not features. He learned to sell to sophisticated buyers who had no patience for hand-waving, and to build systems that had to work at the scale of an entire industry's catalog. In 2005 SafeNet, another Nasdaq company, acquired MediaSentry in a cash and stock transaction worth roughly $20 million. Two companies built, two companies sold, and a pattern beginning to show: Fessler is drawn to industries where the operators are sophisticated but the software is not.

The desert detour

A racetrack, not a spreadsheet

Then came the detour that turned out not to be one. In 2015 Fessler founded, developed, and launched SpeedVegas - 100 acres of exotic-car racing in the Nevada desert, where visitors could take a Lamborghini or a Ferrari onto a purpose-built track. It rapidly became one of the leading tourist experiences in Las Vegas.

This is the part of the story that reframes everything before it. SpeedVegas wasn't a software company. It was an attraction - with tickets to sell, timeslots to fill, waivers to collect, staff to schedule, walk-ins to handle, cancellations to absorb, and a booking flow that had to survive a Saturday afternoon crowd. Fessler wasn't studying the tours-and-attractions business from a deck. He was living it, register to register, season to season.

And living it, he kept running into the same wall. The software built for operators like him was clunky, expensive, or simply missing. The tools he wanted did not exist. So he did the thing he had done twice before - he decided to build them.

The build

Made by operators, for operators

TripWorks launched in 2019 with a slogan that doubles as a founding thesis: made by operators, for operators. The company's own account of itself traces its DNA back to the years Fessler and his team spent developing one of the largest tourist attractions in Las Vegas. After a decade of feeling the pain firsthand, they built the platform to solve it.

The product is deliberately unglamorous in the way great operational software usually is. It handles online and in-person sales, inventory, digital waivers, resource scheduling, point-of-sale, gift cards, and the analytics that tell an operator what is actually happening in their business. It plugs into the online travel agencies that resell experiences, watches for abandoned carts in real time, and tries to forecast demand before it arrives. For a zoo, an adventure park, a walking-tour company, or an educational class, it is meant to be the system of record and the system of growth at once.

Details like these are easy to underrate from the outside and impossible to fake. A real-time abandoned-cart alert only sounds obvious to someone who has watched a would-be customer bail three clicks into a checkout. A dynamic-pricing tool only matters to an operator who has left money on the table during a peak week or discounted into a dead one. The whole feature list reads like a list of the small daily indignities of running an experience business, each one answered with a button. That is what "made by operators" looks like when it is more than marketing.

The company frames its values as a short list - a growth mindset, a bias toward innovation, and a definition of customer success built on win-win relationships rather than lock-in. Coming from most startups those are wall decorations. Coming from a founder who spent years on the operator's side of the counter, they read more like a grudge held and then honored.

The money

A Series A, and a bet on AI

In late January 2026, TripWorks announced a $6 million Series A led by Spring Mountain Capital, a US private investment firm. It brought the company's total funding to around $7.5 million and set a clear direction: pour the money into artificial intelligence and business intelligence for operators - predictive demand forecasting, smarter and more dynamic pricing, and automation that quietly does the work a small operator never has time for.

Fessler's framing of the raise was characteristically about the customer rather than the company. The investment, he said, "fast-tracks our mission to redefine what's possible for experienced operators through AI, business intelligence, and automation." The phrasing matters: not what's possible for TripWorks, but for the operators it serves. The plan behind the money is to widen the AI pricing and revenue tools, push into new markets, and grow the product, engineering, and customer success teams - the round was followed within weeks by an expansion of the leadership team.

The arc

Three decades, one habit

Line up the four companies and the shape is hard to miss. An internet-software company sold at the turn of the millennium. An anti-piracy company that put its technology inside nearly every major studio and label. A physical attraction carved into the desert. And now a platform trying to modernize an entire category of small and mid-sized experience businesses. Different industries, different decades, one recurring instinct: find the place where skilled people are stuck with bad tools, and build the better ones.

Along the way the Entrepreneurs' Organization handed him its "Entrepreneur Startup Award of the Year," and he has served the group as a board member - a reminder that Fessler's peers tend to be other people who build things and can't quite stop. He is based in New York now, running TripWorks out of the city, though the company's roots also reach into New Jersey, where a state innovation fund has backed it.

What makes the story worth telling isn't the exits, satisfying as the numbers are. It's the method. Fessler keeps proving a quiet point that a lot of software gets wrong: the fastest way to build a tool people trust is to first need it yourself, badly, on a busy Saturday, with a line out the door. TripWorks is the fourth time he has run that experiment. The bet, once again, is that the best product spec is a scar.