How This Owner Bought a Property with No Money Down and Turned it into a Top 50 Hotel

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On this episode of Suite Success, host Katie Cline sits down with Jim Nagle, owner and managing partner of the Drake Oak Brook, an Autograph Collection Hotel, to unpack one of the most unconventional paths into hotel ownership. From starting as a Chicago attorney and bus driver to acquiring a legacy hotel with no money down, Jim’s story challenges everything we think we know about risk, experience, and what it really takes to win in real estate.

But this isn’t just a story about a deal—it’s about proximity, persistence, and the mindset required to see opportunity where others see uncertainty. In fact, a visit to Richard Branson’s Necker Island offered a front-row seat to world-class brand building and reframed how he thought about opportunity.

Today, The Drake Oak Brook is recognized as one of the Top 50 hotels by Condé Nast Traveler, but getting there required navigating the Great Recession, rebuilding during COVID, and redefining what hospitality means at its core.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠Lodgify and Bilt!⁠⁠⁠⁠

⁠Connect with Jim:⁠

• ⁠⁠⁠⁠⁠⁠⁠Jim’s LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• The Drake Oak Brook’s Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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Welcome to Suite Success

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0:37

Meet Jim Nagle

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I’m Jim Nagle and you’re listening to Suite Success.

You’ve just checked in to Suite Success. Join me, Katie Cline, for exclusive conversations with hotel executives, hospitality leaders and industry innovators.

Together, we’ll uncover the strategies and techniques these Masters of Hospitality relentlessly refine. Whether you’re already in the industry or just starting out, tune in every week to unlock the secret to your Suite Success.

Hello, everyone, and welcome back to another episode of Suite Success. I’m your host, Katie Cline, and today I’m thrilled to welcome Jim Nagle to the show.

Jim is currently the owner and managing partner of the Drake Oak Brook Hotel, part of Marriott’s Autograph Collection. But Jim didn’t come through hospitality in the traditional way.

1:48

From Law to Real Estate

He began his career as a Chicago attorney, a third-generation lawyer who also spent time as a CTA bus driver before making a bold pivot into real estate during the Great Recession.

With no formal hospitality background, he acquired the Drake Oak Brook after it had fallen into disrepair following a Ponzi scheme collapse. Today, the hotel has been recognized by Condé Nast Traveler as one of the top 50 hotels in the world.

Jim, thank you so much for joining us today.

Great to be on the program. Thanks for inviting me, Katie.

Of course, we have to start with your background because as I mentioned in your intro, you’re a third-generation lawyer, you spent time as a bus driver.

This is not the traditional path I hear on this show, so I want to hear a bit about that and how you eventually ended up in hospitality.

Sure. Well, yes, my grandfather was a lawyer, my father was a lawyer. Actually, my father is still alive.

He’s 93, he’s still a lawyer. So, followed in their footsteps. Then, actually, during the war in Bosnia, I took a pro bono case to write the Constitution for Bosnia.

Through that experience, met a Bosnian Serb who was truly American success story, came from communist Yugoslavia in the 60s and built a fortune in real estate.

He was building a bridge over the Drina River that was literally and figuratively trying to keep Yugoslavia bridge together when Bosnia was seceding.

Through that experience, he asked me to be his lawyer when we got back to Chicago and I said, I’d rather learn real estate. He became not only my partner, but really a great mentor. His name was, he passed away a couple of years ago.

3:38

Mentor and Mindset

His name was Slobodan Pavlovic.

I’m sorry to hear that. It sounds like such a formative relationship.

It really was. He really was a unique individual, to say the least.

Had you never invested in real estate before meeting him?

Other than our home.

Right.

I was always interested in commercial real estate. When we got back to Chicago, the first deal we put together was an old beat up building on the northwest side of Chicago.

Eventually, several years later, we converted it into a charter school for the Hispanic community. It’s still there today and thriving.

That’s so cool. How old were you when you started down this? You were already a lawyer and then you started to invest in real estate.

About what point in your life was that?

In my early 30s. Wow.

Incredible. What was it about working with him that made you think, I need to start investing in real estate myself? I want to learn about this.

I guess it’s that old adage, you can’t judge a book by its cover.

You’d look at him and he’d be the last person that you would think. He drove an old car, kind of like Sam Walton, that he built this really incredible business all with starting with absolutely nothing.

Then he was using his wealth that he’d accumulated in the US to try to go back to his home country and give them the same opportunity they have in America. That’s why he wanted an American-based constitution.

Right. Wow. That’s a beautiful story.

It reminds me a lot when my mom was younger.

5:14

Buying the Drake Brand

She was like a teenager and she was working at a chain, which was called Wetzens at the time. They tell me it’s something like Nathan’s, like a hot dog chain, fast food joint.

She said, there was always this gentleman who had come through the drive-through and he drove this beat up car and he had garbage all in it, and wrappers, and coffee cups, and everything, and these teenage kids not very nice, but behind his back

would call him Junkie Joe. Then they ended up finding out that this gentleman owned multiple apartment buildings.

So I really love stories like that of, we can’t really, like you said, judge a book by its cover or what we think wealth looks like, doesn’t always look the way it does, and quite frankly, sometimes what we see as presented as wealth is the people

Exactly.

Your junkie Joe describes Pavelvich to a T.

Wow. Wow. I read that you had owned many different types of real estate, many classes of real estate before you purchased this hotel, that you owned multifamily, retail, office, industrial.

You just talked about a piece right there. What made you want to purchase this hotel?

6:21

Necker Island Lessons

When you did that, did you see it as just another class of real estate, did you really understand I’m now getting into hospitality as well?

I think more than hospitality, I had a really unique opportunity to spend a week with Richard Branson on Necker Island with the group. This was, I don’t know, 16, 17 years ago going into outer space.

I was the only one out of the 20 that wasn’t going to outer space, but the whole week, all Branson spoke about was his Virgin Brand. I had never heard the word brand used so much as I did that week on Necker Island.

When I got back to Chicago within a year or two, this property which had been vacant for four years, but it was the Drake, it was the Drake Oak Brook. I knew that I was acquiring the Drake brand.

That was on mine and my wife’s mind from the very beginning, that we’re building a brand, not just a hotel.

You have to tell me how you ended up getting to Necker. What led to that? Because that’s an incredible experience right there.

Well, the same through my partner Pavlovich.

His niece was one of the astronauts and he couldn’t make it to Necker Island, so I was the plus one.

Wow. What was that experience like?

It was incredible. I met some phenomenal people. I mean, very interesting people.

I mean, these were all, since they were little kids, were in love with outer space, Star Trek, and they had accumulated wealth. I remember one of the Pritzker’s from Illinois was there.

Branson really used it as a real marketing hook to get all these very wealthy and influential people together under the umbrella of this.

I remember the first time, the very within the first hour, a young man came up to me, he was much younger than me, and we started talking. He said, I just changed my name. I’m Branson’s nephew.

So what do you mean you changed your name? He said, yeah, my name is now Ned Rock and Roll. And I said, you got to be kidding me.

Wait till you’re the end of the story. So really nice young man. And a couple of years later, he ended up marrying Kate Winslet from Titanic.

So I just, you know, it was a very eclectic group of people that I was.

So you’re telling us that Kate Winslet’s name is actually Kate Rock and Roll.

There’s a lot of articles. I don’t think she ever took the name. But he couldn’t have been a nicer.

He was actually one of the hosts. And, you know, they have great hospitality on Necker Island, as you can imagine.

But the real experience was it was kind of like going to school listening to Branson and how he built his brand and then expanded it into different industries.

8:59

Pulling the Trigger

And had you already made the offer on The Drake before going to Necker, or was it being there that really made you think we should go buy that asset?

It was being there coupled with my wife and I had almost bought another property that we were at the closing table that we knew was a great deal.

And we let it get away from us. And it was one of those things we said never again.

Yeah.

You know, my wife’s really sharp. She’s from Mexico originally, and she was in real estate her whole life. She understands real estate.

And it was, I think, one of those life decisions or lessons. You know, when you have a good deal, go for it, grab it. And I think that was had a large impetus in how we ended up buying the Drake Hotel here.

You know what I’m interested, Jim, because I am on a much smaller scale than you right now.

I own three short term rentals and I am actively looking for my first commercial deal. And when do you get to the point when you know it’s a good deal?

Because I’ve gotten to all three of my properties so far, I’ve thought they were and they have proven to be, but you’re always not really sure.

And now moving into that next step of commercial, bigger numbers, potentially investors being involved, it feels so much scarier to me. And I’m looking for that confidence to be like, I’m certain, and even when I have it, I still feel uncertain.

So what do you do to make yourself feel more confident in those situations?

Well, again, I had a great teacher, mentor, who I think the biggest thing I learned from him was he was fearless when it came to buying real estate. I mean, we’d make offers on a big property, he’d be there for three minutes. Okay, we buy.

Don’t you want to see the rest of the property? Well, it’s there to see. We know this is a good deal.

We buy. And some of the other, I still stay in touch with another young guy that learned from him that’s doing very well. And I think that’s what it is.

There’s too many people that just won’t pull the trigger. You know it’s a good deal. Go ahead and buy.

You know, and you look over the lifetime, you know, you can’t, you generally, you know, for the general rule, you can’t go wrong by borrowing money to buy an appreciating asset.

And as long as the numbers work out, you know, the value of every property doesn’t matter what asset class, multifamily, office, hospitality is a function of the income.

11:38

CTA Bus Driver Days

So if you can see that, you know, as we’re talking, I’m thinking, you know, my, he passed away a couple of years ago, all of his little sayings, does it pay the bills? You know, or we’d look at a beautiful piece of property.

If it didn’t pay the bills, he’d say, okay, you’re beautiful, I’m handsome, but what are we going to have for dinner tonight? Which was his way of saying, okay, it’s a beautiful building, but it doesn’t pay the bills. Right.

And I think when you look at the bubbles, or we saw in Chicago when it was, everything was going from apartments to condos, we knew it was crazy. He was telling all of our local community banks, what are you doing?

And a lot of them ended up filing bankruptcy or getting shut down by the feds because they didn’t pay the bill. They’re making loans that didn’t pay the bills.

Right. So simple when you put it that way, yet when you’re in the moment, it’s easy to feel swayed by that beautiful piece of property.

Right.

I want to go back to you being a bus driver. When did that happen?

Well, my uncle, Jim Gallagher, and he was really part of The Daily, the mayor of Chicago, and he ended up being on the board of the CTA. So it was a prime job to get. When everyone was making $3 an hour, I was making $13 or $14.

So I worked as a bus driver to get my way through school. But thanks to my uncle Jim, and that’s how it works in Chicago with the patronage, I was able to pay my way for school because of that job.

That must have been a really cool job, like getting to experience the different people and the stories and the characters. Was it enjoyable or was it like we are paying the bills and we are done with this the soonest we can be done with this?

13:21

Drake Decline and Ponzi Scheme

No, I say when I ultimately became a trial lawyer and you’re picking a jury, the jurors are the people that I drove on my bus.

They’re not all Harvard alums.

Right.

Also, I think it gave me, appreciate the different neighborhoods of the city of Chicago. I’ve been in Chicago my whole life. I love Chicago.

I think people from Chicago and the Midwest are some of the best people on the planet. So getting to drive these people to work and pick them up in the afternoon and take them home. As a young kid, I really enjoyed it.

Yeah.

I certainly enjoyed the money.

Exactly.

What that allowed you to do with going to school at the same time.

Yeah. I always had money for beer.

The Drake Oak Brook is a landmark hotel from the 1960s. It was once frequented by Frank Sinatra and King Charles, so some pretty big names. But as we mentioned earlier, it had completely fallen into disrepair after a Ponzi scheme collapsed.

14:28

Rebuilding Through Crises

What happened there?

I think it was always resting on the location and its laurels. It’s the same thing. I go back to learning real estate.

I can go into any apartment building and you can see which owner is putting money back into his property and which owner is taking the money out. I think what happened, the Ponzi scheme itself, he ended up in federal penitentiary cheating people.

That was actually what my wife and I did ultimately with the hotel was what he was promising the investor class. I believe he stole close to $100 million, never did anything with it other than stealing it.

And then it fell into the hands of a religious group and we ended up, my wife and I, purchasing it from the religious group.

Okay.

Wow.

That is crazy. I read that when you had first acquired the hotel, you retrained the hotel staff as a construction crew. You worked alongside them to actually physically rebuild the property.

Is that accurate and where did that idea come from?

Well, it came from how, when I had all the property, the other asset class is going into 2008, 2009, was that everyone that had real estate knows it. For our industry, it wasn’t a recession, it was a depression. How many banks went under?

I hate to say I knew several people committed suicide. As a kid, you heard the stories from 1929, right? Well, in real estate, we saw that firsthand.

Great community banks go under, people losing everything. And I came very close to that.

And I was, I thought, okay, the typical deal, let’s say a retail center, I could go out and get a tenant, and the way it would work before 2008, 2009, go back to the bank, get out a loan, hire a general contractor, he’ll build it out or build a

vanilla box, and then the tenant will come in and do the rest. Well, in 2008, 2009, we had all kinds of vacancies and no banks, not only were we not giving money, our banks were going under.

I had a commitment from a bank in Illinois for over $10 million. It ended up, after the commitment was issued, they went under. So I ended up taking basically what were my janitors, and we started building it out ourselves.

I remember our first deal was a sporting goods store, and we really didn’t have a lot of knowledge or experience, but we just kept plugging away and plugging away.

And then, you know, thank God, with the help of my wife, we were working 18 hours a day, we paid off all of our loans, got out of that, and then The Drake was, came up for sale. And I had this crew, and they’re like, Jim, what are we going to do now?

You know, we sold most of our properties. I said, okay, well, hey, we, over the years, surviving the great recession, we developed all these skills building out, you know, we had built offices, apartment building, shopping centers.

We became really good at it and really frugal. When it’s your money, we’re sitting here in the restaurant we designed and built this restaurant ourselves in six months. So we learned how to do it very efficiently.

So when COVID came along with The Drake, we had just become a Marriott Autograph, borrowed more money to do the PIP, hired on more people. And every hotel had shut down.

My wife and I sat down and we’re like, wow, we had two women that were going on our team that were part of the hotel staff that were in chemotherapy. We’re like, look, we can’t have everyone lose their insurance. This is the very beginning of COVID.

So we decided, hey, we still had work to do here. Anyone that wants to do construction can keep their job and their insurance benefits. So we converted roughly 70 people and they helped us finish the hotel to the Marriott standards.

Wow.

Not the women in chemotherapy, they were not doing the construction, right?

No, but we kept them on. I mean, here you can sweep or do something. I mean, they were still coming in and they weren’t bedridden.

But I mean, everyone, I mean, you remember that time, Katie, everyone was terrified. I’m talking February, March of 2020, April. We didn’t know what was going on.

And we saw what was going on in Italy and China. And we couldn’t let our teammates lose their insurance. We, thank God, found a way.

And it ended up being a great, a positive thing for us. We came together more as a team or a family. And when we came out of COVID, when nobody was, it was so hard to find anyone, we had a line out the door of people that wanted to work with us.

Yeah, it’s extremely rare for a hotel during that time to have not laid anybody off.

19:31

Hard Times

It’s a huge, huge coup to what you guys did. Because, like you said, it was a really scary time.

You know, I get a lot of credit for that, but I’m gonna be very brutally honest. A lot of that was my wife. She has so much faith.

And she’s like, you know, we’re not doing this. Believe me, my accountant, our management team, they had shut down all their hotels. And you thought, hey, this is the only thing we can do.

How can we pay these loans? We have no money coming in. You know, we had opened with Marriott in February or March and the room revenue went through the roof.

We’re like, oh my God, this is incredible. And then, you know, 30 days later, boom, shut down. So I give my wife, Telly, she has so much faith.

And thank God, I followed her advice on that one because all the professionals and experts were not saying that.

20:18

COVID Renovation Hustle

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21:07

Discovering Hidden Talent

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That’s Suite like Hotel Suite. Yeah. And I have to wonder with what you went through during the Great Recession.

You said you came very close to losing things yourself, but then you found a way and you got it done. I almost wonder, did you feel super afraid? Like here it is happening again and now I have this expensive acid and like, what am I going to do?

And you know what? I’m getting out of real estate. I never want to like go through this again.

Or did you almost have more confidence? Because you’re like, we’ve survived that before. This is just a different kettle of fish of the same thing in a way.

I think it’s when you’re going through it, like the 2009, you think to yourself, woe is me, this is the worst thing in my life.

But when you look back at it, a lot of times those turn out to be the best things in your life. You just don’t know it at the time. For us, my wife and myself, it taught us to be so resourceful.

It taught us how to construct, how to build, how to solve the problems. So when they came up with COVID, we had just been through it before, but we had a lot of work to do.

Actually, the atmosphere, I know a lot of other was shut down, but we had people working in different guest rooms. We have an old hotel, so it’s plaster. You can’t find plaster people.

So we have a big wall unit at all the rooms. It’s like, okay, let’s start on this wall because it’s going to be hidden. So after they did 100 walls, they got to be experts at it.

Now we can go and do the walls that are going to be visible to the guests. So it was like things like that. And so you had bartenders that were laying tile that had never laid tile.

I had a dishwasher that ended up going into the trades. It’s funny with the trades. When you’re in construction, you’re doing it, you see some people have it and just some people don’t.

And you know within three days if they have it. So I had another person that was basically like a janitor. He ended up going into the trades and we’re like, wow, this guy is just phenomenal with his hands.

He can fix anything, he can do anything. You know, hey, what are you doing here? And he started his own business.

So, you know, same for him. I’m sure he’d tell you this story.

Yeah, it was very scary and everything else, but it ended up, it was one of the, and I think through history, you know, if you look at the great fires in Chicago, we end up building a better city. And we just don’t realize it at the time.

At the time, yeah. It’s a beautiful perspective. You spoke a lot about your wife, Telly, and how involved she’s been in this transformation.

What has it been like building this together and how do your roles complement each other? Where do you kind of come together? Where do you separate in terms of roles and responsibilities?

Well, she’s very influential.

She has great taste. And I think with interior design, it’s the same thing. You can look at a woman and see if she’s put together with her outfits.

And some people have it and some people don’t. And she has really phenomenal taste. And so obviously, we still worked with the design team out of New York.

We did it ourselves and then we redesigned the hotel again with Marriott. But it’s still being designed again and again. And so she has a very big hand in that.

My wife’s originally from Mexico.

24:45

Hospitality Learning Curve

She’s very huggy-feely. A lot of our workers are Hispanic. So you can’t walk through the hotel without seeing all the team members come up when Telly sees and give Telly a hug.

So I think that’s some of the biggest attributes. I think just last year, American Lung Association named her Mother of the Year. And some of the other people that had won that were Hillary Clinton and just Meryl Streep.

So yeah, I married up Katie.

Yeah, that’s incredible. It sounds like an amazing partnership for sure. Speaking of partnerships, you’re talking a lot about working with Mariette and particularly being part of Autograph Collection.

You mentioned earlier that right before COVID, when you became Autograph Collection flagged, you saw your room revenue spike. So I’m just interested in hearing from you. What’s it like partnering with a big company and a big brand like that?

What are maybe some of the challenges and then what are some of the upsides?

I think it’s all been upside for us. I can’t say enough. I think it all comes down to your attitude.

So we came into this and we said, okay, we’ve done a total of zero hotels before this one. Marriott’s done 8,000. I’m sure we can learn a lot from them.

So let’s really lean into everything with that attitude. Starting with the one bit advice that Mr. Marriott tells all of his team members and franchisees, if you take care of your team, your team will take care of your guests.

The most simplest advice, but the best advice and we try to follow that every day.

26:34

Top 50 In The World

Yeah.

It’s so true.

Going back to what I asked earlier, I’m wondering when you purchased the hotel, did you really understand at the time how this would be different from every other real estate class and that you would come part of hospitality because it feels so

We were totally clueless.

I mean, we were naive. You’re right, the hospitality is such a different asset class. Remember the other one.

If you think about it, apartment, you fix it up, rent it out, you collect a check, that’s it. This is running a complete business from everything, from marketing to taking care of the gas, to food and beverage, to everything else.

So we had thought, oh, this was a great real estate play. Let’s see where it takes us. We get the Drake brand.

Of course, everyone’s going to stay here. It’s the Drake. We really didn’t realize the value of the loyalty memberships and how loyal someone like the people on the Bonvoy program are.

Obviously, we’re Titanium members now, so we understand it now, but we did not understand it at the time.

But we realized very quickly that we needed a brand, and that’s why the Autograph Collection, the soft brand worked out perfect for us because you can’t pick a better iconic brand name than the Drake in the Midwest.

So able to keep that, but then hook up with Marriott, have them help us in every aspect. I don’t think there’s a lot of franchisees that take advantage. I mean, the tutorials they have on the Internet for everything.

I mean, so we’re thrilled with Marriott.

Yeah, that’s incredible. Obviously, it’s working because Condé Nast Traveler has named you one of the top 50 hotels in the world. What did it feel like to hear that news?

That was surreal.

For us, it’s like winning, I guess, the Oscar. And so, I really think it comes down, it starts with the advice that Mr. Marriott said, take care of your team and taking care of our team members.

They go above and beyond what any other property does to make sure that our guests are taken care of. And I’m sure, I know there’s other hotels whose art collections are more valuable than our hotel. But people make people happy.

And our people, our team members know how to take care of our guests. And that’s why we won the award.

You can see it in older properties, ones that aren’t as well-maintained. If they have an incredible staff versus a brand new perfect hotel with a cold interaction, people are still going to like the older version.

So if you can bring to life this gorgeous new hotel and have staff who really care and take care of your guests, it’s going to do super well.

29:41

Scholarships For Families

Right, right.

And then obviously we upgraded everything. We have a master craftsman. So we build all our own furniture.

If you look at this, everything, we build everything here at the hotel. So I think everyone comes to work every day with a smile on their face and loving what they’re doing.

Yeah, absolutely. It’s not just about how the guest feels, but also how your associates feel in their, quote unquote, office every single day.

Absolutely. And I think you have to love service. If it’s not for everyone.

And you find out, you may have a brilliant, hardworking person, but they’re not into service. So they don’t belong in hospitality.

Right. When someone walks into the Drake today, what do you hope they feel and how do you differentiate yourself from your competitors in the area?

We want, from an aesthetic standpoint, that wow. When they come in and it’s harder and harder to get that because more of the guests are so well traveled. Everyone’s coming up with their A game to outdo the next.

And I think we’ve hit that particularly. We sit on with the land next door, roughly 19 acres. Our grounds are, we built waterfalls everywhere.

We recreated the Vatican Gardens out. I mean, so we want to really get them with the wow factor.

And I have an older building, so the aesthetics of the building, I think really, from that standpoint, kind of the contrast when they walk in through the lobby or through our portico chair. So we want that wow moment.

And then from there, it’s from the doorman to the front desk agent to everyone, making sure that they’re really taking care of.

Speaking of taking care of, I heard that you personally review multiple scholarship applications every year from your employees’ children and their grandchildren.

And that last January, you awarded $100,000 and every single applicant received a scholarship.

31:48

Expanding Into Africa

So I need to hear more about this.

Sure. So when I was in law school, I remember one of the best days of my life, I was going to switch law schools to save $1,000. And the dean of the law school called me in and he said, why are you transferring?

And I told him, look, I’m trying to save every dollar I can. And he offered, I remember the name of it was the dean or the Edsel Olson Trust Fund Scholarship and it was $4,500. And this is in the 80s.

And I thought I had won the lottery. So when we came here now, so many, it’s kind of like the Marco Rubio. We shared his story with his father.

It’s the same thing we’ve took this before Rubio became secretary of state. We knew his story. His family was immigrants from Cuba.

His father worked as a bartender in a hotel, you know, and I have the same, I’m sure the exact same type of people working with us as bartenders, as cooks, as housekeepers, just as Rubio’s parents and said, you know, the thing that they gave Rubio

was the education. He’s a lawyer. You know, look at your kid can be the next. Now, then we said center.

Now we say secretary of state and everything else. But it’s kind of, you know, and it’s a great feeling. We do it at Christmas time at the employee Christmas party.

So my wife and I and our kids are very proud of that.

That’s amazing. That’s really what an amazing way to give back not only to your associates, but then to their next generation as well.

Right.

Yeah. What’s next for you? Do you see more hotels in your future, more real estate?

What’s next?

What we’re doing now for the past year, we’re working in Africa. We took our brand and we did license and deals. We have three in Africa.

We started in Ethiopia. I had a young man come to work from years ago from Ethiopia. He just reminded me of the Pavewits story.

He wanted to go back and bring the best of America to Ethiopia. He left, but we stayed in touch. War broke out in Ethiopia.

I said, you know, it’s like, it was reminding me of Bosnia-Takasta. When the war is over, people are so hungry for business and jobs, I’d be interested to start something. We open up our office.

We did our first deal in Tigray, which is in the north of Ethiopia, not only a Drake Hotel, but also an amusement park. Now, keep in mind, this is Ethiopia’s first amusement parks. I mean, it’s a beautiful amusement park.

It’s not Great America, but it’s still, it’s like the old riverside, the old people in Chicago remember that. So that’s operational. The hotel will open in the fourth quarter of this year.

And we have other deals that we’ve lined up along the way as far as that goes.

Wow, very cool. I love that. So potentially more expansion in Africa.

Yes.

And actually, we just got back from the World Bank Forum in DC. They asked us through that, they’re building a huge airport. And he said, Jim, do you know airport builders?

I’m like, are you kidding me? We’re from Chicago. They’re doing an $11 billion renovation rebuilding O’Hare.

So we put together a consortium. And a lot of those people, we took over to Africa. And actually, we just got back from DC yesterday.

The US government through JP Morgan and Citibank is announcing that they’re going to finance the whole deal and they want American contractors. So we’ve lined up a lot of these Chicago through a consortium to participate in that construction project.

Very cool. Very exciting. Lots more to come.

Watch this space.

And we’re calling it the Drake JV, The Drake Joint Ventures. But you can find it on, to see more about that, www.drakejv.com.

Very cool. Jim, I want to ask you the last three questions that I ask every guest. And the first is, what was the best hospitality experience that you have ever had?

Sure.

That’s easy. My first trip to Bosnia, right in the Constitution, was during the war. Sanctions were on.

I remember we had to come in through, fly into Budapest and drive to cross the border, which was a challenge. And there was a family that met us in Belgrade.

And if you’ve ever been there, it’s a beautiful city, but a lot of the residentials are like the old communist, like Moscow, you know, multi-tenant, you know, not really nice.

And this family that we had never met before sat down and gave us a meal in kind of a stark apartment. And it was a very nice meal. And my partner Pavlovich was saying, hey, you know, eat everything, eat everything.

And when we got out, he said, Jim, do you realize that, you know, they’re on rations, that was two weeks of their food that they just gave to you.

Yeah.

And I don’t think people realize, you know, when war breaks out, the first thing that happens is that all social unwritten contracts fall to the wayside and it’s man, every man for themselves.

So I’ll never forget that, that, you know, to lay out the best china, to give us all their food and, you know, I felt so guilty afterwards, but that was hospitality.

37:43

Suite Summary

And I don’t think we’ll experience anything like that again.

Yeah. And on the opposite side of that, what was the worst hospitality experience you’ve ever had?

I think the worst hospitality experience was, I mean, everyone has these stories. We, we took our daughter and grandkids to Europe, and we had to come back early for emergency. We’re trying to find a hotel.

We finally get there at three in the morning, and they open up our room that’s supposed to be ours. And it’s just a complete mess. People were sleeping in there, and it was like, yeah, you couldn’t believe that this was a real hotel.

I mean, I just say that because we, it was the worst, but we laughed. We had so many great stories out of that. There’s so many stories that happened that night.

So it was the best, but it was the one we talk about, laugh about the most.

Yeah, for sure. And final question for you, what does hospitality mean to you? And is there anyone, it could be a person, it could be a brand that you think has truly mastered it.

I think hospitality means to me it’s the art of making people truly feel taken care of.

And I think a lot of our success, obviously the answer shouldn’t come as a surprise. I think my wife exudes that. I think in a very genuine, sincere way, you can tell that she loves it.

I think it’s that persona that’s in the culture of our property that has helped us win all these awards.

It’s a beautiful answer, Jim. Thank you so much for spending the time with us today. I really appreciate it.

Oh, it was a pleasure.

I really enjoyed it, Katie. Thanks for having me.

All right, everyone, it’s time for today’s Suite Summary where I break down the key insights and actionable takeaways from today’s conversation. Chatting with Jim was a powerful reminder of how much our environment shapes what we believe is possible.

When he was an attorney, it was a single relationship, his mentor, that opened the door to real estate in the first place.

By watching, learning, and staying close to someone who had already done it, and was continuing to do it, he didn’t just gain knowledge, he expanded his perspective on what was achievable.

Then by traveling to Richard Branson’s Necker Island, the idea for acquiring The Drake took shape. Not because someone handed him a blueprint, but because proximity shifted his thinking.

It made something that felt out of reach suddenly feel possible. He shared something powerful with me after we stopped recording. He was able to acquire The Drake with no money down.

Not because of luck, but because of credibility. Years of doing the right thing, of paying down loans even in the hardest lending environments, built a track record strong enough that a bank was willing to fully fund his dream.

And when he told people what he’d done, they didn’t ask how. They dismissed it, wrote it off, told him it couldn’t be done even though he had just done it. That’s the thing about proximity.

When you’re in the wrong rooms, you inherit other people’s limitations. But when you’re in the right ones, you start to question them. Because what looks impossible from the outside often just means unfamiliar.

And that’s what makes Jim’s story so compelling. When others said it couldn’t be done, he found a way. He acquired a legacy hotel with no money down.

He worked 18-hour days and took on renovations himself when banks weren’t lending. He repurposed hotel staff into a construction team during COVID to avoid layoff. Because to him, this isn’t just an asset on a balance sheet.

It’s a living, breathing business built on people, on loyalty, on trust, and a sense of responsibility that extends far beyond the bottom line.

When you combine proximity with persistence and pair it with a genuine commitment to people, you don’t just build a portfolio, you build something that truly lasts. That concludes another episode of Suite Success.

If you enjoyed today’s conversation, please subscribe, rate, and review the show. We all know how important those five-star reviews are. I also want to say a massive thank you to each and every one of you for tuning in.

It means the absolute world to me. I’d love to hear from you if you have ideas for future guests, new topics to cover, or even just want to say hi. Don’t be shy.

Message me through our website, suitesuccesspodcast.com, or on social media, at suitesuccesspodcast.com. That’s sweet like hotel suite. Once again, I’m your host, Katie Cline, and I’m super excited to see you all next week.