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Hospitality Upgrade Marks Three Decades in Business Q&A with Rich Siegel, Publisher

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June 10, 2022
Fran Worrall - fran@hospitalityupgrade.com

Hospitality Upgrade recently turned ‘the big 3-0,’ and founder Rich Siegel was honored by longtime colleagues and friends at the Executive Vendor Summit in Dallas. Following the meeting, he sat for an interview and answered some of our questions about his early days in hospitality, his 30-year publishing career and his proudest moments. He also talks about his mentors and offers advice for anyone starting a new venture.

HOSPITALITY UPGRADE: Tell me about your first couple of jobs in the hospitality industry.


RICH:  When I graduated from high school, I knew I wanted to go to college but I didn’t know what I wanted to major in. I came from a middle class family, so if you went to college you had to take out a student loan. After a year, I realized I was spending a lot of money without a clear direction of what I wanted to do. So, I quit school. But while I was at college, I had worked at a campus tavern. The guy who had managed the bar there was opening another tavern at a different school, and he asked me to help out with the opening. I accepted, thinking I’d be there a few days and that would be it. But within the first week the manager was fired, and I was asked to manage the bar. I was only 19 years old! I took the job and ended up working 60 to 70 hours or more a week, but it was a lot of fun. After two years there, I realized I wanted a career in the hospitality industry and decided to go back to school to study hotel and restaurant management. I ended up at Sullivan County Community College in the Catskill Mountains, where I was introduced to the guy who owned the Laurels Lake Hotel in nearby Loch Sheldrake, NY. He gave me my first job in the hotel business, working the front desk. It was exactly like the hotel in the movie Dirty Dancing. I learned so much there about hotel operations and how to treat guests. I had a great time. Over the years, my favorite jobs have always been front desk jobs. Every arriving guest was a brand new audience.

HOSPITALITY UPGRADE: How did you get into hotel technology?


RICH: I was living in New York City and working in hotels. It was the early 1980s, and very few hotels had property management systems. I was a front office person, and I was enamored with computer systems. It was interesting to see what they could do. Anyway, I ended up being offered a job in San Francisco, so I moved out there to work as the rooms division manager at the Travelodge at Fisherman’s Wharf, which was the biggest property in the Travelodge portfolio at the time. As it turned out, the manager and I just didn’t connect. I was there for a month and miserable the whole time. But that’s where fate intervenes. I was staying at the hotel, and one Sunday night after realizing that the job wasn’t going to work out, I came back to the property after dinner and hit the elevator button so I could go to my room. I waited and waited and waited. During that time, it occurred to me that I needed to take care of something in my office. So, I walked down to the office, and sitting there on the receptionist’s desk was the Sunday edition of the San Francisco Chronicle. Of course, I picked it up and turned to the classifieds. And there it was—a listing that read: ‘Looking for hoteliers with strong front office experience who want to travel the world.’ How could I not respond to that? I typed the most amazing cover letter and sent it with my resume. The company ended up calling me, I went in for an interview, and I got a job as an installation and training specialist for Hotel Information Systems. Now, back to fate. If you’ve ever read the book The Five People You Meet in Heaven, you know it suggests that there are no random acts and everything is connected. So, I often think that one of the people I’ll meet in heaven is that person who was in the elevator that Sunday night. If I hadn’t been forced to wait so long, then I wouldn’t have gone to my office, I wouldn’t have picked up that newspaper, I wouldn’t have gotten the job in technology, and my entire life would have turned out differently.

HOSPITALITY UPGRADE: What led you to publishing?

RICH: When I took my SAT test in high school, my teachers thought I might have set a record for the widest gap between math and English. I was really good at math and really bad at English. (To this day, my sister says the fact that I’m writing and publishing amazes her.) Anyway, I had been selling property management systems for eight years. I had gone to Australia, and when I came back I took a new job. The company was paying me a lot of money but I hated the job, so I decided to move on. This was in 1991, and I thought the industry could use a technology newsletter. There was only one newsletter out there called the CKC Report. It was published by a consultant, and let’s just say there was room for a different approach. I didn’t know the first thing about publishing, and I remember contacting a dozen PMS companies and asking them to spend money with me launching this newsletter. Out of those companies, 11 said ‘yes’ the first time I met with them, and the last one eventually came around.  We still joke about that first newsletter. It was 28 pages on bright yellow paper with a penguin on the cover. That’s what happens when you finish a newsletter at 4:30 in the morning and you have to be at the printer at 8 a.m. I’ve learned a lot along the way, and it has been an amazing journey. By the way, the plan was to move the penguin slightly in every issue, just to see if readers would notice.


HOSPITALITY UPGRADE: What’s one of the most memorable stories on your journey?

RICH: That‘s a tough question. As I look back on 30 years, I think about the early days when I had just launched the newsletter. At the time, I didn’t have a good relationship with the head of the IAHA, the group that sponsored HITEC back then. (IAHA was the International Association of Hospitality Accountants and the predecessor of HFTP.) But I didn’t let that stop me. I attended HITEC in San Diego, and it wasn’t a good event. So, in my write-up after the show I shared my thoughts about what happened at HITEC and why it wasn’t successful. What happened next was interesting. I had friends who were on the HITEC advisory board, and they had a meeting soon after that newsletter came out. One of my friends told me that every person at that meeting brought out the newsletter and my editorial was a topic of discussion. The consensus was that I was right. I didn’t realize the power of the pen back in the early 1990s. When I wrote something, people reacted to it. It’s still the same today. So, as I look back over 30 years, what is most memorable to me is knowing that I’ve had an audience and people have listened to what I’ve said.

HOSPITALITY UPGRADE: Can you name one or two of your proudest achievements?


RICH: Most people would say that being inducted into the HFTP Hall of Fame was their proudest achievement. It was certainly an honor, but I wouldn’t consider it one of my proudest achievements. This is a tough question because so many wonderful things have happened to me during this 30-year career. But a big highlight was being asked to moderate the opening session at HITEC 25 years ago. Until then, I had never spoken in front of more than 10 people, and there had to be more than 400 people in that room. But I can be a creative person, and I opened the session with a song I had written for my 8-year-old nephew about being a CIO, and he was there to sing it in person. It was unbelievable. No one was expecting it. Try to imagine a kid singing about why he wanted to be a CIO and 400 people at the end of the song standing up and cheering. It was an amazing moment. Afterward, as I started the actual session, I remember Danny Hudson, who was at Starwood Hotels and Resorts, getting the first question from me. He paused, looked up at the audience and said, “I’ve learned that when you speak in public you never want to follow a kid or an animal, and I get to follow both.” Think about it . . . he had just called me an animal! But things like that loosen people up and get them laughing. I think humor has helped me a lot during the course of 30 years. Another proud moment was when consultant Jon Inge was inducted into the HFTP Hall of Fame and I got to introduce him. I’ve never had so much fun picking on a person as I did with Jon Inge. It was just one of the greatest moments. A room filled with hundreds of people at the opening session and everybody is laughing.

HOSPITALITY UPGRADE: Why did you start the CIO Summit and then the Executive Vendor Summit? 

RICH: I was doing a face-to-face interview in Chicago with Tom O’Toole, who was CIO at Hyatt Hotels. Afterward, during lunch, he asked me about some of the other CIOs in the industry. I realized that everyone he was asking me about—people he knew by name but didn’t know personally—were people I knew really well. So, I gave him my two cents on the different CIOs and he said, “You would be a perfect person to bring us all together. I’d love to meet my peers.” Well, it sounded good, but this was right after 9/11 and I was worried about my business. I couldn’t think about doing an event, and I didn’t know how to do an event. But a couple of months later, I was in Atlanta having lunch with a friend at Bass Hotels (before it was IHG) and I stopped by to see Doug Lewis, who was the CIO there. I told him about my conversation with Tom O’Toole and asked him if he would attend an event for CIOs. He said he not only would attend but also would make Carl Wilson, the CIO at Marriott, come with him. I reached out to Tim Harvey at Hilton and several others, and everybody said they would attend. So, in September 2002, we held the first CIO Summit. We invited 25 CIOs, including three from the gaming industry; and only the brands, no management companies. Of that group, 23 said they would come and 21 showed up, and everyone said we should do it again. The Vendor Summit came a couple of years later. I started thinking that vendors would like the same kind of event. Even though they compete with each other, I thought they would enjoy getting together because they have to partner with each other. So, we held the first Vendor Summit in 2004 and it was a big success too. I can’t believe this will be our 20th CIO Summit and we’ve had 17 Vendor Summits, and they both started out with about 20 attendees. We had more than 100 attendees at the Vendor Summit this year, and we’re expecting close to 80 at the CIO Summit and from all areas of the industry—hotels, casinos, cruise lines and vacation ownership companies.


HOSPITALITY UPGRADE: Have you had any mentors along the way that you’d like to recognize?

RICH: I’ve had two mentors. The first was David Shaw from Postec. He and I were both in Atlanta, and his company was the largest distributor of Micros products and very successful. It was the early 1990s, and I was just launching my business. I’ll never forget that David had a meeting in Atlanta with another distributor, and about 20 people were there. The first issue of my newsletter had just come out, and he made every attendee pay to subscribe. When you’re starting out, that’s a big deal. I got to know David well, and through the years he was someone I went to when I had struggles or challenges or when I just didn’t know how to do something. When you’re a start-up, you need someone you can go to for answers, and David was someone I could always turn to. My second mentor was Harry Harrison, my financial advisor. When you start a business and go deeply into debt and live in debt for the first seven years of that business, it’s good to have a financial advisor who encourages you, gives you direction and makes suggestions. Harry did that. As I look back on the 30 years I’ve had in this business, I think of him often. And he continues to help me make financial decisions to this day. So, I thank David and Harry for being my mentors.


HOSPITALITY UPGRADE: Any advice you would give someone just starting out – in publishing, the hotel tech industry or with a new business?

RICH: I’m frequently asked for advice, especially about starting a business. And I give simple advice. Often, people have a great idea and they want to create a business out of it. But they have responsibilities—a mortgage to pay, feeding the kids—so they do the business on the side. My advice is this: if you believe in what you’ve created or what you want to create, then dive in headfirst. You’ll either succeed or fail, but don’t do it tentatively. Take a chance and go for it. That’s what I did. And that’s the only advice I give.

HOSPITALITY UPGRADE: You were roasted at the recent EVS and ‘HU at 30’ event. Do you have anything to say to the many roasters or something you would like to rebut? You have the stage now.


RICH: I was really looking forward to the roast and the whole ‘HU at 30’ celebration, and it surpassed anything I could have imagined. The funny thing is that everyone said I was going to be roasted, but I really wasn’t. It was just people sharing a lot of great stories about things they remembered over the past 30 years. So, as I look back on that night and all the comments and funny jokes and the great celebration, all I want to do is say ‘thank you.’ Thanks to the roasters and special thanks to co-hosts Gregg Hopkins from PROVision Partners and Richard Tudgay from Highgate Hotels. And a big thanks to the HU team, both past and present, who helped me reach this milestone. You’re only as good as the people you surround yourself with, and I’ve been surrounded by great people for 30 years.


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