“I found retirement really, really boring,” says Tim Choate, Founder and CEO of RedAwning. For this serial entrepreneur with a talent for spotting digital opportunities, boredom sparked what would become a transformative force in the vacation rental industry.
Choate’s journey to RedAwning follows a career at the forefront of digital innovation. A Wharton graduate, he began at Prodigy, one of the first consumer online services in the 1980s.
“Prodigy was really a bleeding edge company backed by IBM and Sears,” Choate recalls. “Most of the predictions they made back in the 80s proved to ultimately be true, just not as fast as they would have liked.”
This early exposure shaped his entrepreneurial vision, which he parlayed into a series of startup successes at an early age. His first venture pioneered digital software distribution: “One company I built was the first to actually sell you a software product you could download.” After pioneering a successful sale of the company, he soon launched an online advertising company implementing early machine learning technology he called “dynamic revenue optimization” long before AI became a buzzword. That company went public and was eventually sold in 2007.
After attempting retirement in his 40s, Choate found himself restless. The idea for RedAwning came during a European vacation when he experienced firsthand the frustrations of booking vacation rentals.
“I found the entire experience was an absolute nightmare,” he says. Quickly looking at the situation through an entrepreneurial lens, he observed, “When I looked at the scale of the problem, I realized this is a really big category. I didn’t understand why no one made a simple online booking for vacation rental properties.”
The original concept was straightforward: create a hotel-like booking experience for vacation rentals. “RedAwning was a brand around a hotel-like experience for a vacation rental property. Come in, find a place, put in your credit card, and book it.”
What distinguished RedAwning from the beginning—including from Airbnb, which was starting around the same time—was its commitment to instant booking. One hundred percent of their listings were instantly bookable, a novel concept at the time.
As the company grew, Choate realized that acquiring guests was challenging and expensive. This led to a pivotal strategic shift: partnering with platforms already investing heavily in guest acquisition.
“We ended up partnering with the other players who actually were spending a lot of money getting guests, and through that process, I guess in a way, we invented channel management as a category for the vacation rental space,” Choate says.
For the first seven years, RedAwning was bootstrapped—a deliberate choice inspired by eBay’s early growth strategy. By 2017, however, it became clear that external funding would accelerate growth. The company raised its first and only round of capital from private equity, which proved crucial in navigating the challenges of 2020 and beyond.
Today, RedAwning serves approximately 20,000 properties, from major resort companies like Vail Resorts to individual property owners. What sets the platform apart is its fully integrated, vertical approach.
“We have in the US a unique platform that is designed to do everything that a host needs all in one place, and everything that a guest needs all in one place,” Choate says. “In the US, I think we’re the highest ROI platform in the industry, so we tend to generate a lot of interest from real estate investor-type clients, because if someone wants to make money, we’re really good at that.”
Unlike typical channel managers, RedAwning has unique contract structures with major platforms that give them significant advantages:
“The channels see us as a property manager. Booking.com looks at us and says, ‘This is one of our largest property managers. They have tens of thousands of properties.'”
This status allows RedAwning to offer property owners access to platforms they couldn’t reach independently, including Marriott Homes and Villas, which are typically only open to professionals.
RedAwning’s fully integrated platform has positioned the company to implement AI more effectively than competitors. They’ve already deployed AI across multiple functions:
“Because everything comes into us from all the channels, we have billions of points of data,” Choate explains. “We actually injest close to a billion points of data per month, because the channels share with us a lot of information that helps us succeed.”
Analyzing this data provides a rich set of insights, allowing RedAwning to optimize listings across channels, studying factors like cancellation policies, amenities, pricing, and keywords to maximize performance.
“We study what listing factors perform well in which market, and help clients optimize around those. Because our whole concept is we only make money when our clients make money,” Choate emphasizes.
For real estate investors in the short-term rental space, RedAwning’s pitch is simple: “More revenue, less work,” says Choate. The platform handles everything from photography and pricing to calendar management, payment processing, channel distribution, and marketing.
The company offers tiered service levels, including full-service remote management for owners who can’t handle the volume RedAwning generates. Their commission structure is straightforward—10% for the base model, with channel costs covered through channel-specific pricing.
RedAwning’s data-driven approach extends to optimization recommendations for individual properties, including insights on policies like pet allowances, which can increase exposure by up to 100% in drive markets. And, the platform now offers industry-first features like seasonal cancellation policies. “We’re the first in the industry to offer this. VRBO told us we’re first,” Choate says. “Having a soft cancellation policy during periods of less occupancy is going to put you first, versus other people who don’t have that capacity.”
Notably, Choate demonstrates his confidence in the system through personal investment: “I’ve generated over $1 million in reservations for my two homes on our platform,” he notes.
Choate believes the vacation rental industry sits at an interesting crossroads where technology increasingly addresses the practical challenges that once deterred many potential real estate investors.
“Real estate is more stable,” Choate notes, referencing recent market fluctuations. This stability, combined with emerging technology solutions that handle operational complexities, may attract investors seeking alternatives to traditional markets in times of turbulence.
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