# Aaron Fessler

> Aaron Fessler is the founder and CEO of TripWorks, an AI- and business-intelligence-driven booking and automation platform for tour, activity, and attraction operators. A serial entrepreneur who started The Allegro Group in the attic of his family's barn in Ohio, he has built and sold two technology companies - Allegro (to Mail.com for $40M in 1999) and anti-piracy pioneer MediaSentry (to SafeNet for $20M in 2005) - and created SpeedVegas, a 100-acre exotic car racing complex in Las Vegas. In 2019 he launched TripWorks to build the operations software he wished he'd had while running attractions himself, and in early 2026 raised a $6M Series A led by Spring Mountain Capital to expand its AI pricing and revenue tools.

- **Role:** Founder & CEO at TripWorks
- **Organizations:** TripWorks, SpeedVegas, MediaSentry, The Allegro Group, Entrepreneurs' Organization
- **From:** Ohio, United States
- **Nationality:** American
- **Known for:** Built and sold The Allegro Group to Mail.com for $40M, Founded MediaSentry, which became the largest anti-piracy provider for motion picture and recording industries, serving Sony Pictures, Warner Bros., Fox, Disney, and MGM, Sold MediaSentry to SafeNet for $20M

## Career timeline

- **1990s** — Launched The Allegro Group from the attic of his family's barn in Ohio
- **1999** — Allegro Group acquired by Mail.com (NASDAQ: MAIL) for $40M in cash and stock
- **2001** — Founded MediaSentry, the largest anti-piracy service provider for the film and music industries
- **2005** — MediaSentry acquired by SafeNet (NASDAQ: SFNT) for $20M in cash and stock
- **2015** — Founded, developed, and launched SpeedVegas, a 100-acre exotic car racing complex in Las Vegas
- **2019** — Founded TripWorks, a booking and operations platform for tours, activities, and attractions
- **2026** — Raised $6M Series A led by Spring Mountain Capital to expand AI pricing and business-intelligence tools

## Achievements

- Built and sold The Allegro Group to Mail.com for $40M
- Founded MediaSentry, which became the largest anti-piracy provider for motion picture and recording industries, serving Sony Pictures, Warner Bros., Fox, Disney, and MGM
- Sold MediaSentry to SafeNet for $20M
- Created SpeedVegas, a 100-acre exotic car racing experience that became a leading Las Vegas attraction
- Awarded 'Entrepreneur Startup Award of the Year' by the Entrepreneurs' Organization
- Raised a $6M Series A for TripWorks in 2026, led by Spring Mountain Capital

## Latest updates

- **2026-01** — TripWorks raised a $6M Series A led by Spring Mountain Capital to expand AI-driven pricing and revenue tools and grow its product, engineering, and customer success teams.
- **2026-02** — TripWorks expanded its leadership team following the Series A round.
- **2026-05** — TripWorks recognized as a top tour platform in industry rankings.

## Links

- Website: https://tripworks.com
- LinkedIn: http://www.linkedin.com/in/aaronfessler
- Twitter/X: https://twitter.com/Trip_Works
- YouTube: https://www.youtube.com/watch?v=dpPGpXslbZI
- Facebook: https://facebook.com/tripworkssoftware

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Profile page: https://yespress.io/aaron-fessler
Published by YesPress — https://yespress.io
Last updated: 2026-08-06