Risk and Reward: Jim Kelly’s Formula for Lasting Success

What does it take to transform diverse experiences into entrepreneurial success? Jim Kelly's remarkable journey from politics to building a billion-dollar travel reservation system provides a masterclass in strategic career maneuvers and meaningful risk-taking.

Through this candid conversation, Kelly reveals the delicate art of finding mentors—not by asking vague questions about what to do with your life, but by approaching them with specific requests that inspire their guidance. This small distinction makes all the difference in cultivating relationships that propel careers forward.

Kelly's entrepreneurial story defies conventional timelines, having launched his tech company in his fifties during the early days of the internet. His innovative approach to hotel reservations—offering software for free while charging half the industry rate per completed transaction—revolutionized the space. The strategy that secured MGM Grand as a client and subsequently opened the entire Las Vegas market demonstrates how strategic thinking and clear storytelling turn vision into reality.

Perhaps most valuable is Kelly's insight about team building: "With the right team, you can do anything." This wisdom, particularly relevant for startups where only 2% survive, offers a roadmap for building organizations primed for success.

Ready to make your own daring choices? Kelly's experiences illuminate how skills accumulated across various fields create the foundation for innovation and leadership.

Purchase Daring Choices: Stories From An International Life in Politics, Business, and Technology

Chapters

• 0:00 Introduction to Jim Kelly
• 1:27 The Story Behind the Book
• 5:30 Finding Mentors and Putting Yourself Out There
• 10:30 Building the Right Team
• 15:20 From Dreams to Business Reality
• 21:20 Disrupting the Hotel Reservation Industry
• 25:05 Breaking into Las Vegas Market

Transcript

James B. Kelly III: 0:00

I'll do another marker. Okay, this is a marker. I'll give you guys another count in.

George M. Davison: 0:12

The beauty of not being live TV.

James B. Kelly III: 0:16

All right, guys. Big smiles Looking right here in three, two.

George M. Davison: 0:22

Hello everybody and welcome to another edition of Tomorrow's World. Today and today we have a special guest. His name is Jim Kelly. Welcome, jim, thank you. Good to be here. Well, jim's had a successful life in business, technology and in politics, and at one time he was in the Reagan administration. He's also built a company from scratch. It's called Synexis Corporation and it is actually a travel reservation system that's now around the globe. But today he's become a best-selling author on Amazon. Congratulations, thank you. Yeah, so I'm hoping today you're going to share some of your stories with us that are in your book called Daring Choices, and I mean you've really had an interesting journey, so I was hoping you could share with our audience today. You know why have you collected all these stories on your life and put them in this book for us?

James B. Kelly III: 1:23

Well, let's start with how it happened this book for us. Well, let's start with how it happened. First of all, I grew up in Pittsburgh and I returned here in 2017. And by chance, I had a dinner with a guy named Max King, who's pretty well known in Pittsburgh. He'd been head of the Pittsburgh Foundation, but at one time he'd been an editor of the Philadelphia Inquirer. I told him a couple of my stories and he said, jim, you've got to write a book about this. I said, well, max, let me think about that.

James B. Kelly III: 1:57

So at the time, part of the reason why I returned to Pittsburgh was I was an executive in residence at the University of Pittsburgh Katz Graduate School of Business, and students would frequently ask me. I tried to give examples of things that I'd experienced in my business career and as ways that they could look at what they were trying to do, and the question always came up why did this happen, how did you do this and why did you do this? So I thought about that and I thought about what Max had said to me, and then I guess it was a couple months later I ran into him. He had written the book on Mr Rogers. I ran into him, he had written the book on Mr Rogers and at the release he said how's your book coming? I said well, I haven't started yet. He said get busy. So when a man of that stature and experience tells you to better, you better sit down and try and write a book.

George M. Davison: 3:04

I got started, so your listening skills were still intact.

James B. Kelly III: 3:09

Yeah, well, I follow orders.

George M. Davison: 3:12

That's all right. I think, at the bottom of the hour, though, we're going to want to figure out why you selected these stories and you put them together for an audience, because you more than likely wanted to help some people along the way, didn't you? Well?

James B. Kelly III: 3:30

I really was interested in showing how one thing leads to another in life and a lot of people, I think, tend to engage in one thing and they stick with it, and some become very good at it, others don't.

James B. Kelly III: 3:49

But some people learn from that experience and they apply it to the next door, so to speak, the next road in their life, and I think a lot of young people have a fear of not trying things that may prove to be not only outside their envelope but very difficult. So I try to show here that it is not necessarily easy, but if it's handled with some degree of finesse and you're careful about how you do it, you can change from one thing to another in your life and you can try and have a lot of different experiences, which in the end should turn out to be fun, as they were for me.

George M. Davison: 4:39

Yes, you had a very active life there for quite a bit, building all these things.

James B. Kelly III: 4:46

I had a lot of luck too. I had a lot of people that helped along the way, and that's another thing that I've encouraged young people to do is to gather around them people that they can look to as mentors in their career, in their life going forward, and I had that with people like Elsie Hellman here in Pittsburgh, who's well known here, drew Lewis from the eastern part of the state and, in my technical career, with a guy named Dave Huebner who had been in the Defense Department and head of the Research Department of the Defense Department.

George M. Davison: 5:32

So, somehow or another, jim, you became comfortable in what I refer to as the uncomfortable and going out meeting people that you don't know. There's an art and a system to doing that and I think a lot of our audience probably is very unfamiliar with that. Many of them may also be shy, but, who knows, they may want to pursue a career as an entrepreneur or to excel in the business or political world. To excel in the business or political world how did you find that you navigated into this initially, like how did you become so confident that going up to meeting strangers who you knew could be influential in your career? What convinced you that that was a good idea to do to create these mentors?

James B. Kelly III: 6:24

Well, there's no question but that I am an introvert, which a lot of people ask me. How does an introvert do the things that you've decided to do? And it's just hard work. And you've got to be willing to put yourself out there. And if I can go back to Max King for a second, I asked Max. I said Max, with all your wisdom in life, tell me why do you think this happened to me? And he said well, you put yourself out there. And that's the real lesson of this book, whether it's I mean. I'll give you one example.

James B. Kelly III: 7:10

I was a project engineer in Spain. I was home on vacation. I met Elsie Hellman. I said you know, elsie, I've always been interested in politics. I said do you think I might? This was in 1968, when things were kind of on edge, to put it bluntly and lightly. But she said have you thought about trying to help out here in the political situation? I said no, I hadn't really. She said well, give it some thought, and if you'd like me to help you with it, I'd be glad to do that, and if you'd like me to help you with it, I'd be glad to do that. And so the same thing happened with Drew Lewis, my other mentor, who was the transportation secretary in the Reagan administration. He one day asked me. He said you know, you seem to know a lot about the international business. Mack Baldrige is looking for somebody like you. Would you be willing to give it a try? I said yeah. So I put myself out there and said, yeah, I'll do that Next thing. I know I was sitting there with Mack Baldrige.

George M. Davison: 8:15

And so that is a big part of the equation, isn't it Absolutely? Being able to put yourself out there. Give yourself an opportunity to expand yourself. Maybe your knowledge and people have that ability to do it. It's not just anybody, it's, for example, if you're in an area that you don't have some mentors that you feel are strong individuals. Be patient, try to find, you know, good mentors. Try to put yourself surround yourself with good people who can help you grow. Is that a fair way to say it? Yes, indeed, yeah. I think that's a key part of this, because a lot of folks they you know. Maybe they grew up in a bad family environment, maybe they've. They're in an area of town that's not all that wonderful, they haven't been exposed to a lot of good things. So getting them to think differently about how to get out of that situation and you can go out and find mentors right, you can, and there's an important element of this.

James B. Kelly III: 9:21

A lot of people in search of a mentor go to someone that they think can be a mentor and they ask the question what do you think I should do with my life? And that doesn't work. Mentors, prospective mentors, don't respond to that very well. The question should be I would like to try this or this is what I would like to do. Can you help me do this? And all the people I know that have become serious mentors of other people have always pitched in. When they're given a clear question, a request, they will jump to be of help. But if you go to them and say, what should I do with my life, that will not carry the day.

George M. Davison: 10:16

Right. So that's good advice, very good advice for the audience today. Let's see here the audience today, let's see here you know you said in your book that you wanted to help students try to figure out what's ahead of them, and I was thinking on that. And you know that falls into the category of, you know, having a noble cause. You know, and now today you're out here talking about your life and the stories that have helped to shape you, compose it into a book. Is that what motivates you, chasing noble causes, to try and do some things that are better for others?

James B. Kelly III: 10:57

Never heard it put that way, but probably true.

George M. Davison: 11:01

That's the way I interpreted it when I read that. Yeah, that's the way I interpreted it when I read that.

James B. Kelly III: 11:03

yeah, it's one of the companies that I worked where I worked, bdm, we had a saying do things that count, and that's another kind of lesson that I've tried to pass on to students and younger people that I've worked with that when you think about your life and the things that you're doing, make sure that whatever you do, do it well and make sure that it counts for other people and for their future as well as yours, and for their future as well as yours.

George M. Davison: 11:46

Yeah, it hasn't been easy, has it In the book? There are moments in there where you were challenged pretty seriously. Bad hiring from one angle that could have got you into some challenges, right, yes, and you had to make some tough choices and take on the board and push your way forward, but you were on the side of what was right, what was the right thing to do. Right, it's not always easy.

James B. Kelly III: 12:12

Well, that takes me to another kind of observation. When I've spoken to a number of business classes, I ask them, I say, what's most important? Is it the investor, the customer or the employee? And invariably the business students will tell me it's the investor or it is the customer. They kind of forget about the employee.

James B. Kelly III: 12:41

And I've always said that with the right team you can do anything. And so life is really about bringing together the right people, and there was a book that was called the Good to Great getting all the right people on the bus in the right seats on the bus, on the bus in the right seats on the bus, going in the right direction. And I think that's an important lesson. And one step beyond that is important that when you have someone who is not a part of the team or who is working against the team, you need to change that person very quickly. And what I've seen is that most personnel decisions are made too far down the road. You need to make personnel decisions the minute you know that you need to make that change.

James B. Kelly III: 13:36

And this is true in many instances with people who start companies. In many instances, with people who start companies, companies or new ventures are usually started between a couple of friends, and one of the friends ends up driving the train, the other one kind of along for the ride. That shouldn't last very long, and it's a very important lesson, because only 2% or so of the startups survive. So you know, one of those reasons is that not everybody's on the same page when it comes to completing their assignment. Right Couldn't agree more.

George M. Davison: 14:17

So just to give you some leeway here, I wanted to ask you if you could tell us about your life, of turning dreams into goals and then into results.

James B. Kelly III: 14:30

Dreams to goals to results well, during my business career not not, not so much the political activities that I undertook I paid attention to the people above me and at some point oddly enough, it was in my early 50s.

James B. Kelly III: 14:57

I didn't say I know it all, but I concluded that I knew enough that I could start a business, and it just Providence.

James B. Kelly III: 15:10

I guess it just happened that that was the beginning of the internet. And so I said to myself I'm going to now use all the things that I learned to start a business. I have no idea what that business is going to do, which surprises a lot of people, and I'm going to bring together that team that I just spoke about and we're going to make it happen. So we started in a business which was putting the yellow pages online, which was a business that gave us the money to then enter into the hotel reservation space. And the hotel reservation space came about because I was told precisely what the problem was by the reservation manager of one of the major hotel groups, and the rest is kind of history. We made that product over a period of five or six years and it's now that company was, I think, recently sold for over a billion dollars. So that's the transition from the thought process to accumulating the team that it takes to do the job, and then actually doing the job and taking the product to market.

George M. Davison: 16:33

Yeah, you know, it's interesting because you started as an entrepreneur but you were in your 50s, which is unusual.

George M. Davison: 16:41

And it's interesting from another angle too, because you spent so much time in that political arena but you were exposed to a lot of accomplished folks and you traveled a lot.

George M. Davison: 16:53

I'd say there's one other critical piece to the equation and that is you have to be searching for and making observations and in your case I'm wondering does that mean that at the age of 50, something you were saying to yourself I'm not quite fulfilled, I want to become an entrepreneur and I'm going to venture out of the political landscape and start going in this other direction? It? Was it like that? Was it that clear? Or was it because they thought you do talk about that in the book, but just can you expand on that a little bit that moment in time of working for someone else? Because you were in the government but working for somebody else. And then actually you had you were working for another organization, which is BDM. You had them and you were working with them, but there was something that must have transitioned you to say, no, I'm going to go out and go on my own.

James B. Kelly III: 17:49

That is a good question, george, and I want to take it back to. There is a point in time where I was asked to join a company and they asked me to take an assignment of acquiring companies for them in Europe, because I'd had business experience in Europe but I had never been in the acquisition world. So I said, all right, I'll do this, but I need to understand acquisition accounting stand acquisition accounting. So they agreed to send me to the University of Michigan for a two month course in acquisition accounting and I went to Europe and reviewed over 200 companies and we acquired a few of those, and so each of the things that I did there was a piece of the puzzle that I made a concerted effort to acquire what I thought I was missing.

James B. Kelly III: 18:50

And one of the things that I point to in the political side, and particularly working at a high level in the administration the Reagan administration was that I learned to write. I mean, I knew how to write. I had worked for a senator and he was an excellent writer and his administrative assistant was a former newspaper editor. So I had the basics, but Secretary Baldrige was a real stickler about writing. So I learned there how to write and how to make a business presentation and with that again I felt I had another piece that I could carry forward in building a business and it's kind of all of these things that I acquired in my career that came together for the purpose of starting a company together for the purpose of starting a company.

George M. Davison: 19:48

So the art of writing helps to get the story out as to what you're trying to accomplish is that?

James B. Kelly III: 19:50

why, absolutely, and that, more than that, the, the presentations, the PowerPoint presentations. You know, I I worry about young people being able to write. Now I mean because we see what's happened with email and autocorrect and so forth. Writing is definitely a required skill of success, definitely, and I say that people should read, they should write and they should write well.

George M. Davison: 20:29

I agree with you and I'd take it a step further, because you made another comment earlier about how you took a different type of accounting financial acquisition. So it's writing and telling a good story, but also you have to be able to. In this case, you said make acquisitions, but also you're going to go out and raise money, aren't you?

James B. Kelly III: 20:51

Yes.

George M. Davison: 20:52

In order to raise money, you really need to understand money. Yes, so that's another important ingredient.

James B. Kelly III: 20:59

You have to be able to understand money, but you also have to be good at storytelling. You have to be able to tell the story of what's happening to the money in a way that people understand more than the numbers Agreed. The money has something before it and after it, and you need to build that into a story.

George M. Davison: 21:23

So initially you had to raise money to get this off the ground. I think it was 400,000 is where you started and you went through a method to do that meeting with people and telling the story of what you wanted. Can you walk us back in time a little bit so that this audience can relate to that moment where the Internet was coming into place and you had your area of knowledge? You had a customer who was in that field of doing something with hotels told you about this problem that was going on and you looked at that and said you know, I think with technology and with the right programming we could turn that into a business and we could scale that. So can you talk a little bit about what us a few stories that might be really compelling for the audience to know about that really were critical stepping stones that let the company move into a more stable financial position Because you had to raise money? I think a couple of times, yes, oh, yes, I think a couple of times yes, oh, yes, yeah, we.

James B. Kelly III: 22:44

From a technology standpoint, two things were happening at that moment that we I won't say that we were first, because I'm sure there were others out there but we presented our product as a software, as a service SAAS which has become rather commonplace now. But at that time, having the company hold the software and putting a graphic user face in front of the customer and saying go to it, that was very unusual. And we charged transaction basis, which was unusual. Most of the reservations were provided in a software package. You bought the software and you ran it and then you figured out what your costs per reservation were. We only charged on a completed reservation. So we gave the software away. We said here it is, it's yours, it's free, but you owe us. And we cut the price of reservations in half. And so people were absolutely keen to use it.

George M. Davison: 23:58

And there's one moment Can I pause you for a moment? So, in other words, a thing that was going on this is a critical moment where there's something else in the marketplace and it's kind of set. You have to buy it, you have to have a learning curve, you go through this process, et cetera, et cetera. And you looked at that and said, no, there's a better way, et cetera, et cetera. And you looked at that and said, no, there's a better way. And then you set about a series of I'll just call them strategic objectives to outmaneuver the old way of doing it, and one of them, one of those ways, was how to configure an easier way for these hotels to adopt what you have versus what the standard at that time was. And the old saying is, if you can give it to them for free, that's a pretty powerful motivator. So you did figure that out. Oh, yes, okay. So that's a very critical part of your innovation. What are a few of the other ones?

James B. Kelly III: 25:01

What are a few of the other ones? Well, I wanted to give you one of the stories where everything very quickly transitioned. Okay, I went to we had a fellow who was head of strategy and he said, you know, he said we've got to be looking at Las Vegas. So I'd never been to Las Vegas. So I somehow, or another, I got a meeting with the president of the MGM Grand Hotel. That's just largest hotel in the world with 5,000 rooms.

James B. Kelly III: 25:33

So I go into his office and I'm at the table. It's a big table and across the table from me is his head of IT, therefore the guy that runs his reservation system. So it's a mano a mano and I did the best I could. I explained what our system was and what it was going to cost him nothing, and the guy across the table didn't really have much to say. So MGM adopted the system and then every hotel in Las Vegas had to have the same thing that MGM had in order to defend themselves in that really basically tiny market. So that moved us ahead and from then on it was our game.

George M. Davison: 26:22

Yeah, that's wonderful. I love that story. It shows you how to move and it gives you an example of how to think strategically and move your product or service so that you can get adaptability right. How do you get absorption of what you've created? Because there's a lot of great innovation in the world, but it just never really gets a foothold in the door long enough to survive.

James B. Kelly III: 26:47

Remember, it's that part about you've got to tell a story. It's the story. The story for us going forward was always it's going to cost you half as much as any other hotel to use our reservation system and you're going to have more people staying at your hotel, and so forth and so on. But it was all put together in a story.

George M. Davison: 27:12

Yeah, and it all happened because you put yourself in a position to identify a problem that you thought you could solve.

James B. Kelly III: 27:19

Yeah, Well, it goes back to the fellow who said I need to be able to sell my last room. So the reason Can you explain that a little more?

George M. Davison: 27:30

for the audience.

James B. Kelly III: 27:32

The reason. It's a bit complicated, but in the travel world there are what's called GDS Global Distribution System and GDS is Backstop Travel Agents, and so there are four main GDSs. The best known is Sabre, and Sabre was created by American Airlines and they provide a list of all the hotels and aircraft and car rentals, the hotels and aircraft and car rentals and most travel agents are connected with one of those GDSs. But this travel agent may have, say, a wedding, so he books his allocation of rooms in a hotel through his GDS, say, at.

James B. Kelly III: 28:21

Sabre rooms in a hotel through his GDS. Say it's Sabre. Anybody who goes to him will show that his booking path is complete, there are no more rooms and anybody who's working through that particular GDS.