# Tim Choate

> Tim Choate is the founder and CEO of RedAwning, a Petaluma-based vacation-rental distribution and hospitality platform. Across a career spanning BusinessWeek, Prodigy, Softdisk, Online Interactive, FreeShop.com and Aptimus, he has repeatedly worked on the less glamorous but consequential machinery that connects products, customers and fragmented markets.

- **Role:** Founder and CEO at RedAwning
- **Organizations:** RedAwning, Aptimus, FreeShop.com, Online Interactive, Micro Warehouse, Softdisk Publishing, Prodigy, BusinessWeek, Digital River, LapLink, Berkeley Playhouse, LandPaths, Friends of the Petaluma River
- **Nationality:** American
- **Education:** Bachelor of Science in Economics, concentration in Marketing and Entrepreneurial Management; magna cum laude, The Wharton School, University of Pennsylvania, Graduated cum laude, Phillips Academy Andover
- **Known for:** Founded or co-founded three internet companies across software distribution, online lead generation and travel technology., Led FreeShop.com through a Nasdaq IPO in 1999 and later led Aptimus through its sale to Apollo Group in 2007., Built RedAwning into a vacation-rental marketing and distribution platform serving thousands of clients and more than one million guests.

## Career timeline

- **Before 1994** — Held marketing and operating roles at BusinessWeek, Prodigy and Softdisk Publishing.
- **1994** — Co-founded Online Interactive and served as chairman, president and CEO.
- **1996** — Online Interactive was sold to Micro Warehouse; Choate later served there as a vice president.
- **1998** — Became chairman, president and CEO of the company later known as Aptimus.
- **1999** — FreeShop.com completed a Nasdaq initial public offering.
- **2000** — FreeShop.com changed its name to Aptimus as its model expanded into an online direct-marketing network.
- **2007** — Aptimus was sold to Apollo Group.
- **2010** — Founded RedAwning to bring hotel-style online reservation capabilities to vacation rentals.
- **2017** — RedAwning raised $40 million in growth equity led by Silversmith Capital Partners.
- **2018** — RedAwning acquired Blizzard Internet Marketing and Leavetown Vacations/Jetstream.
- **2023** — RedAwning announced distribution through Homes & Hideaways by World of Hyatt and new communications and automation tools.
- **2024** — RedAwning acquired Awning.com and added remote full-service vacation-rental management.

## Achievements

- Founded or co-founded three internet companies across software distribution, online lead generation and travel technology.
- Led FreeShop.com through a Nasdaq IPO in 1999 and later led Aptimus through its sale to Apollo Group in 2007.
- Built RedAwning into a vacation-rental marketing and distribution platform serving thousands of clients and more than one million guests.
- Raised $40 million in growth equity for RedAwning in 2017.
- Served on corporate boards including Digital River and LapLink and nonprofit boards in arts and environmental stewardship.

## Latest updates

- **2024-04** — RedAwning acquired Awning.com, adding a remote full-service management option and bringing Awning's team and clients onto its platform.
- **2023-11** — RedAwning announced its Superhost Supercharge Program and expanded its Connected Stay automation offering.
- **2023-10** — RedAwning became an accommodation provider for Homes & Hideaways by World of Hyatt.
- **2023-06** — RedAwning added Stay App to its distribution network.

## Links

- Website: https://www.redawning.com
- LinkedIn: https://www.linkedin.com/in/timchoate
- Twitter/X: https://twitter.com/redawning
- Facebook: https://www.facebook.com/redawning/

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Profile page: https://yespress.io/tim-choate
Published by YesPress — https://yespress.io
Last updated: 2026-08-26