Delivering the California Dream: Kirkwood Collection CEO Leverages His Film Industry Experience

Kirkwood Collection

When LODGING spoke to Alex Kirkwood, founder & CEO of the eponymous Kirkwood Collection, he was “in chaos mode in escrow closing on two deals” for his fast-growing luxury boutique hotel investment, development, and management firm. At only 38 years of age now, Kirkwood described an impressive career path where he moved from a successful Hollywood film advertising career to building a boutique hospitality real estate enterprise known for its one-of-a-kind properties—all of which pretty much conforms to the business plan he created as a 14-year-old.

Kirkwood said he first learned about the value of real estate as an investment from his uncle in Seattle, who discouraged his earliest plans to pursue a career in the film industry. “He said, ‘If you go into the movie business, you can really crush it, but it’s a tough career, and you don’t get to own your work,’” Kirkwood related.

Nevertheless, Kirkwood majored in entertainment marketing at Chapman University and, after graduating in 2007, secured a position in L.A. as an assistant to a producer of independent films. Eventually, his three film industry roommates also obtained jobs in L.A., but in the meantime, Kirkwood had to live on a boat in Marina Del Rey as he could not afford to rent an apartment alone.

20th Century Fox and First Purchases

Kirkwood described the factors—including a real estate connection that led to a position at 20th Century Fox—that inched him away from a promising career in the film industry to one in hotel real estate, including a period during which they overlapped.


While working on a movie, he became friendly with producers who owned a hotel in Mexico, which motivated him to begin poring over a broker friend’s listings. Oddly, it was that relationship that brought him into contact with the head of marketing at 20th Century Fox, who hired him to create trailers and posters for the domestic theatrical motion picture division. He remained in the coveted studio system for more than five years, rising to director of creative advertising. “It was there that I really cut my teeth, working 18-hour days,” he recalled.

Yet, at one point, while working as a creative advertising director at Fox, he realized he would never excel at it—not the way his uber-talented colleague, the SVP of marketing, did. “He was brilliant at the job; he could produce in two hours work that took me two days,” Kirkwood said.

However, that colleague was rather less proficient at capitalizing on opportunities in real estate, which came so easily to Kirkwood. “That’s when I decided, if I can’t be the absolute best at this, I don’t want to do it,” he commented. Even working 18-hour days, he had bought three properties—two vacation rentals with his family, and a third, The Palm Springs Hotel, as a joint venture with the family that owned the hotel in Mexico. Given that ability, he figured, “That was probably what I’m supposed to be doing.”

Going It Alone

So, he quit the film-industry job many would have killed for. “Everyone thought it was a little crazy to leave the studio system in the role I’d worked so hard to get only to start out at nearly square one,” he said.

His family members, who he called “founder investors,” were supportive. They had already joined him in purchasing vacation properties for their family to enjoy together and rent out back in 2012 and continued their support for the first six hotels and vacation rentals that launched Kirkwood Collection in 2016.

Much to his surprise, all did not go well at first. “I thought I would just leave Fox and the banks would roll over and finance whatever project I proposed. Instead, I had a nightmare of a time getting my first full solo deal. I just couldn’t put the financing together on the deals I wanted. I had just enough capital to pursue one more deal. If it failed, I would be one deal away from becoming an Uber driver.’”

Thankfully, that deal—The Hideaway in Santa Barbara—worked out, and The Kirkwood Collection began to take off.

Boutique Focus

Kirkwood said part of the problem with getting financing when he was starting out was likely his insistence on focusing exclusively on the boutique segment, unlike most of the flags the lenders more readily invested in at the time he was launching his company. That segment remains his focus: “I myself like a uniquely boutique, localized experience and especially love historic architecture, which is why most of our assets are historic.”

As the Kirkwood Collection has grown, they are creating a loyalty program of their own, and their properties—all of which are in California—can share the management resources of the company, he explained.

And unlike flagged properties that are similar, there are no restrictions on Kirkwood Collection properties in terms of their distance from one another due to competition considerations, because they are not only unique, but also small. Three of the Collection’s downtown Palm Springs properties are a case in point: the 18-room La Serena Villas, built in 1933; the 17-room Del Marcos Hotel, designed in 1947 by renowned mid-century architect William Cody and named a Class I historic site by the city; and the 10-room Three Fifty Hotel, built in 1950 and renovated in 2017.

The Path Ahead

Kirkwood said the company is poised to grow, with a kind of hybrid structure that includes:

  • The Friends and Family Fund, comprised of the first six hotels and vacation rentals owned with his family;
  • Three other hotels acquired in partnership with Somera Capital Management, a deal he sponsored; and
  • A new division devoted exclusively to Kirkwood-branded management contracts of third party-owned properties.

Describing the company’s plans and expectations for growth, Kirkwood said, “We just passed $100 million in total real estate. We are growing in the owned and operated portfolio and the joint venture portfolio, and we’re now looking to take on our first hotel management contract where we don’t have an equity stake. At this point, we have a 10-property portfolio and a robust pipeline of deals in the works. Our staff is growing, too. We now have about 150 employees and expect that number to double in the coming year.”

Lessons From Tinseltown: The Cinematic Approach to Hotel Design and Marketing

It’s true that Alex Kirkwood, founder & CEO of the California-centric Kirkwood Collection, walked away from his dream of making it in Hollywood to realize his dream of creating unique properties in the hotel industry. Yet, he insisted, these dreams are not so different. “I went from marketing a two-hour movie experience to marketing a weekend getaway experience—something apparent in the theatrical quality of our hotel marketing, including the ‘pedigree trailer’ we created for our portfolio,” he explained.

Kirkwood offered a notable quote from a Fox marketing executive that he said applies just as much to the hotel industry: “If you try to make a movie for everyone, you end up making a movie for no one.”

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