After building a distinguished career managing luxury resorts across the country, Irving Kass purchased the St. George Inn and took on his greatest challenge yet: transforming a failing 22-room property in downtown St. Augustine into one of the market’s most highly-rated boutique hotels.
When Irving Kass purchased the St. George Inn in 2004, he brought with him nearly three decades of hospitality expertise that began as a management trainee at Hyatt Hotels in 1977. After building a distinguished career managing luxury resorts across the country—from Traverse City to numerous Florida Luxury Resorts—Irving took on his greatest challenge yet: transforming a failing 22-room property in downtown St. Augustine into one of the market’s most highly-rated boutique hotels.
Irving’s journey to independent hotelier was anything but typical. After the events of 9/11, he decided to leave corporate hospitality and seek his own property. What he found in St. Augustine was a two-year-old hotel that was, in his words, “probably one of the poorest performing properties in the market.” The previous owner thought guests would bring their own soap, positioning it as a four-star hotel while operating at a one-and-a-half star level.
“The hotel before we purchased it ran 24% occupancy at roughly a $100 rate,” Irving recalls. “We were the last to fill, and only obtain business when there was displacement in the city.”
Through meticulous attention to product quality and service—Irving transformed the property. By 2007, they were running 80% occupancy and had established the sophisticated yield management approach that would serve them for the next two decades.
For twenty years, Irving personally managed the property’s pricing strategy, leveraging his deep market knowledge and industry connections. As chairman of the tourist development council and with leadership roles in various lodging associations, he could tell you “what rates every hotel in town is charging on a daily basis without looking.”
His approach was sophisticated but time-intensive, treating the 35-room property as if it were a large hotel with limited inventory. “I was always thinking a year out that I only had 35 rooms left and how I could maximize revenues while manipulating arrivals and departures to make my staff’s life easier,” he explains.
This strategy worked brilliantly—except during market disruptions like the 2008 financial crisis, the pandemic, and recent economic uncertainties. As Irving notes, “If you don’t have the demand, all of the theories of yield management aren’t as effective.”
The decision to implement TakeUp in February 2025 was driven by multiple factors. At 69, Irving recognized the need to prepare his team for the future. “I’m getting old. I have a great team that works for me, but they do not intuitively understand the subject like I do,” he admits candidly.
Additionally, the St. Augustine market had become increasingly complex, with new supply from out-of-town hotel companies bringing more sophisticated revenue management approaches. “I don’t have the time to really follow all the nuances,” Irving explains, “and I said, ‘It’s time to automate it and to help my team become successful.'”
“The platform is going to make these decisions mostly before we would be manually able to do it. When you’re going up or coming down, people don’t tend to react fast enough. And that’s where the low-hanging fruit is.”
Irving Kass, Owner/Operator of The St. George Inn
True to his process-oriented philosophy, Irving approached TakeUp implementation strategically. After installing a new property management system in June 2024, he deliberately waited six months before adding TakeUp. “We need to be able to walk and chew gum at the same time,” he reasoned.
This measured approach extended to his expectations for the system. Irving understood that with incomplete historical data from their PMS transition, 2025 would be a learning year, with the real benefits emerging in 2026 and beyond. “I’m not looking for immediate results. I’m looking for building the process and the fundamentals because success is not based on results—you could get lucky with results. But if you have process, then it’s sustainable.”
Despite viewing 2025 as a learning year, the St. George Inn has already seen positive returns. “We are definitely making more money than we are spending,” Irving reports. The AI has identified pricing opportunities Irving wouldn’t have attempted himself: “Today I know AI changed it because we’re charging $392.84—that’s not a number I would have put!”
Irving particularly appreciates how TakeUp performs during market downturns. “The platform is going to make these decisions mostly before we would be manually able to do it,” he explains. “When you’re going up or coming down, people don’t tend to react fast enough. And that’s where the low-hanging fruit is.”
The relationship with TakeUp has been strengthened by the quality of their team. Working closely with his dedicated TakeUp revenue strategist, Irving’s 27-year-old manager Caleb has embraced the technology while Irving maintains strategic oversight. “They seem to have a very, very good relationship,” Irving notes, “and he understands the platform extremely well and is literally in there every day looking.”
As the St. George Inn prepares for stronger market conditions, Irving sees TakeUp as essential to capturing the upside. Having recently invested in significant property renovations—he views the AI system as another strategic investment that will pay dividends as demand returns.
“As the market returns, which we know will happen shortly because St. Augustine’s a great destination, having TakeUp learning and becoming smarter every day, we will reap the benefits,” he predicts. “We will get increased demand which means occupancy will go up, and we will get increased pricing because we will not have the delay of reacting.”
When asked about his advice for others considering TakeUp, Irving is unequivocal: “I think your company makes a lot of sense, and if you’re patient and you’re smart and you let the AI continue to improve, I think you’ll see good results over long term.”
Perhaps his most telling endorsement comes with a touch of humor. As he prepares for a wine country trip, Irving notes: “While I’m away, TakeUp will be making us money to pay for our trip.” For a veteran hotelier who’s seen it all, that’s confidence you can take to the bank.
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