Episode 32: Barry Sternlicht - Chairman and CEO of Starwood Capital Group

21 Aug 2025 · 58 min

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Generating Alpha Podcast - Episode 32: Barry Sternlicht

Episode Overview In this episode of the Generating Alpha Podcast, host [Name] interviews Barry Sternlicht, the founder and CEO of Starwood Capital Group. The conversation covers Barry's journey in real estate investment, his early life, pivotal career moments, and insights into successful investing and negotiation strategies.

Key Themes and Concepts

Early Life and Influences

  • Childhood Background: Barry shares his upbringing in a middle-class family in Stamford, Connecticut. His father, a Holocaust survivor, instilled resilience and entrepreneurship values in him.
  • Entrepreneurial Spirit: Barry's early ventures included car washes, selling tadpoles, and teaching tennis, which laid the groundwork for his future career.
  • Education: Attended Brown University, where he majored in law and society. Later, he went to Harvard Business School, where he learned valuable lessons about thinking critically and creatively.

Career Development

  • JMB Realty: Barry learned crucial lessons from Neil Bluhm, such as focusing on larger deals and the importance of being proactive in deal-making.
  • Founding Starwood Capital Group: After leaving JMB during the S&L crisis, Barry raised $21 million and capitalized on undervalued real estate opportunities, quickly expanding his portfolio.
  • Risk Management: Barry discusses the importance of learning from failures and maintaining a proactive approach to risk.

Investment Philosophy

  • Contrarian Approach: Barry emphasizes looking for value in overlooked markets and focusing on sustainability long before it became mainstream.
  • Deal Structures: Starwood Capital’s success is attributed to aligning interests with investors—eschewing typical acquisition fees for management fees based on performance.
  • Market Anticipation: Barry’s ability to predict market trends has allowed Starwood to thrive, particularly during economic downturns.

Design and Branding in Real Estate

  • Importance of Design: Barry believes that design and aesthetics are crucial in real estate, influencing occupancy and financial success. He shares examples from his work with W Hotels and One Hotels.
  • Creating Unique Experiences: The focus on branding to connect with guests on an emotional level has been a hallmark of Barry's ventures.

Negotiation and Leadership

  • Keys to Successful Negotiation: Barry discusses various negotiation strategies, including understanding the other party's needs and knowing when to compromise.
  • Talent Management: He reflects on the importance of building a strong team and recognizing when team members may no longer align with the company's goals.
  • Crisis Management: Barry highlights how crises can unify teams and refocus efforts on core objectives.

Current Events and Worldview

  • Social Responsibility: Barry’s engagement with social issues, particularly regarding the Israeli-Palestinian conflict, is framed by a desire for peace and understanding.
  • Navigating Public Perception: He discusses the challenges of addressing anti-Semitism and misinformation in the media.

Key Takeaways

  • Work Ethic: Barry stresses the importance of hard work and not taking shortcuts in achieving success.
  • Adaptability: Staying open to new ideas and changing one’s perspective is critical in both investing and leadership.
  • Long-term Vision: Successful investing requires looking beyond immediate gains to build sustainable value.

Conclusion Barry Sternlicht's insights provide a template for aspiring investors and entrepreneurs. His blend of creativity, financial acumen, and resilience offers valuable lessons for navigating the complexities of the real estate market and beyond. The conversation underscores the importance of learning from both successes and failures, maintaining a strong work ethic, and fostering meaningful connections in business.

Additional Notes

  • Quote of the Episode: "Hope's not a business strategy; you have to make your own hope."
  • Suggested Action: Listeners are encouraged to take initiative in their education and career paths, focusing on skill acquisition over immediate financial rewards.

Episode Resources

  • [Starwood Capital Group](https://www.starwoodcapital.com)
  • Books recommended by Barry Sternlicht: *Business and finance-related texts focusing on investment strategies and management philosophy.*

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00This week on Generating Alpha, I'm joined by none other than Barry Sternlicht, founder, chairman, and CEO of Starwood Capital Group, and CEO of Starwood Capital Group, and CEO of Starwood Capital Group, and CEO of Starwood Capital. landscape, and real estate through bold acquisitions, innovative design, and brand-driven strategy. Widely regarded as one of the most influential figures in modern real estate, Barry is known for his contrarian eye for undervalued assets, his ability to spot market shifts before they happen, and his track record of creating lasting value across hotels, residential, and commercial properties worldwide.

0:40In our conversation, Barry reflects on a childhood shaped by resilience and early entrepreneurial ventures, the pivotal lessons learned from Neil Blumich AMB, the biggest risks and your misses of his career. We also discussed how his perspective on the world has changed since October 7th, his approach to negotiation, the advice he'd give to the next generation. I really enjoyed making this podcast and I hope you guys enjoyed listening. Please subscribe to the Spotify channel and also the YouTube channel and give it a five out of five stars on Spotify. If you have any friends or family who you think might find this interesting, I'd urge you to share it.

1:12I'm really trying to get the podcast out there. Thank you. Thank you, Barry, for coming on. It's been a long time in the making. I really appreciate it. You're persistent.

1:22and you're from my hometown so I'd like to start off where I always do the beginning tell me a little bit about your childhood and upbringing you grew up in Stanford and you say your parents were very different people kind of give me some background what was your childhood like yeah I grew up in a middle class home in Stanford Connecticut um went to a private school which had a total like 20 kids and went to Westville High School, which had 500 kids in the classroom. So that was quite a little treat. I didn't have any money, so I did odds and sods to make money. So I had car washes and tag sales and sold the tadpoles I caught in the pond across the street in the spring.

2:08And then I devolved into teaching tennis. So I played on the high school tennis team. And also I sold knives door to door in the evenings. I was the second highest salesman in Fairfield County. I set up the picnic tables at the tennis courts with my knives. And we cut tomatoes and ropes. And the gals bought knives for me. So they felt bad for that once curly haired young man that I was with an afro like yours. Bigger than yours. I had a pick. You don't need a pick for that. And I can show you a picture of me when I was young, if you don't believe me.

2:48So my childhood, I mean, was fairly straightforward. I mean, I worked. We drove the car to Florida. I had never been to California, but I was like 18. I went after I graduated high school. My parents took me on a trip to Yosemite. And I went to college at Brown University. I had a raised restriction on how far I could go from the house. But I also had good grades, but not extraordinary. So I don't think I got into – I don't even remember. In my survival techniques, I forget things that aren't good. So I'm just assuming I wanted to go to Brown. I'm sure I didn't get into some of the other schools I applied to.

3:31But it's all good. I play on the Greenwich tennis team, and we beat West Hill this year. but maybe you guys will get back at us next year. Well, we were all state champions. So that was my generation. That was many moons ago.

3:48If I understand correctly, your father was a Holocaust survivor as my grandfather was. He survived the war and he also went through bankruptcy, if I'm correcting your childhood. How did that kind of experience and the way you express those experiences you think shaped your perspective as a young kid? Yeah, my dad was a survivor of the war, but he was like nine when the war broke out and 15 or 16 when it ended. He was the man of the household. It's hard to imagine a 10-year-old boy caring for his mother and grandmother and uncle and sisters, but he did. So he was pretty tough cookie. He didn't talk about the war.

4:24You know, for him, the U.S. was the greatest place on earth, and he didn't want us to know much about the horrors of his youth. He was somewhat religious, but the family wasn't very religious. and my mom wasn't at all. She was born here, Russian parents, and she was a school teacher. So she taught. And then when the boys all left for school, I have two brothers, you know, she became a stockbroker. I think my whole career is a combination of the traits I inherited from my two parents, my mother being very social, super creative. She's a painter. She even paints today. She's 91 years old and she's quite good.

5:05and I got my artistic side from my mom. So I went to the Silvermine Guild for Artists in Newark, Connecticut. I took art classes in high school. Did a lot of the posters for the school shows and things like that. And I did the same thing when I got to Brown. My dad was tough and resilient and had a pretty wicked temper, but it sort of changed as he got older. He got a lot softer and a lot more mushy. Um, but I think, you know, my, my, uh, I always said to myself that my worst day was better than my dad's best day growing up. So I kept my life in perspective, I think. And yeah, he, he was pretty successful.

5:49And I watched, he started a business in Norwalk, Connecticut. Uh, he was an engineer by background and he worked for Bechtel and then he started his own little business. So I think the entrepreneurial spirit came from my dad. He had this little, little company. it was pretty successful for little companies it was like eight or nine million in sales and probably made a million or two million bucks it was u.s affiliate of a french company but my dad got really as a young successful youngish successful small businessman he got involved with like the chamber of commerce you know with the governor of connecticut to china on a mission i think he took his eye off the ball in his business a little bit and i could see the sales were going up but his unit sales were actually going down it was his prices that were going up And I was in high school.

6:32I talked to him about it, and he didn't want to know part of it. Then one time when he was away on a trip, he came back, and they counted the inventory in his factory, and he was missing a lot of inventory, apparently been stolen. So that blew his bank covenants, and the business failed. Turned out the building that he bought was worth more than the company, so they were liquidated for the building. And I guess at the early age, I learned to pay attention to the details and look at the facts and not wish things were true, but deal with them when they turn bad quickly. and for my father they turned back quickly he then got a job with TVA the Tennessee Valley Authority used to commute from Connecticut to um someplace in Tennessee Waverly Tennessee and work on um utilities for the for the for the TVA um and come back on Fridays to my mom who at that point was a pretty successful stockbroker in the Greenwich office of Smith Barney so um And she survived like 16 mergers and she had the exterior office.

7:28My dad retired in his 60s but couldn't get my mom to retire. So he decided at the age of like 68 to take the Series 7 exam and become a stockbroker. Failed his first time, then actually took it. But he was not nearly as gregarious and social as my mother. So they were down the base of Greenwich Avenue. We were the top of Greenwich Avenue. He'd walk up and hit all the guys in the firm and get accounts from them because he was too proud to actually hit on my youth licking envelopes. My mom's mass mailings to people trying to get stock accounts from them and trade with Shearson. But with Shearson, then it was Shearson Lehman, then it was Shearson Lehman American Express.

8:08We call that Shear Sex. And then it became Smith Barney. But my mom finally retired like, you know, 10 years after my dad did. and that was really heartbreaking for her. She still loves the stock market. My father's favorite joke was, has your wife made you a little money in the stock market? And he'd say, yeah, she started with a lot. I made a little out of it.

8:32She owns like one share of every single stock in the S &P 500. So you go off to Brown and then you call your mom and tell her you don't want to be a lawyer, which is her dream for her. And you go to be a consultant and then you ultimately become an arbitrage trader making around$90 ,000 a year. You go to HBS and after you come out of HBS you get an offer. Wait, wait. First job was$24 ,000 a year at Booz Allen. So$90 ,000 was enough money that I could actually pay for the lunch for anyone I was dating. At$24 ,000 if they wanted to order something I couldn't eat anything for that week. No, it was 1982.

9:10Yeah, I graduate. I go to HBS. Can't believe that. One thing about my background, I was a liberal arts major. I majored in law and society. I called it Lost in Society. It was one of everything. It didn't qualify me for anything. It did teach me how to think. And I do think today with AI that thinking is the most important thing. How you instruct these bots and these large language models is everything. So now I think I'm back in vogue. I was out of vogue, but now I'm in vogue. So I get into Harvard Business School without ever taking a math course in college. And I never took a science course.

9:42I never took a lot of different courses. So Brown had a curriculum that let me not take math. And I didn't like math. And that's one of the key reasons I went to Brown. And then I get into Harvard. I expect I will be gone in two weeks because I can't add. And find the calculator is actually pretty nifty. And I actually turned out I was OK with what I call the kinds of math you need in business, not quantum physics and not calculus and not geometry. but the stuff I do, proformas, discount rates, the basic math I can do in my head. And I found out I also had a very good memory, which has been super useful to me in my career.

10:23And you go out of Harvard Business School and you get an offer from Goldman Sachs Real Estate. And then you also get an offer from Neil Bloom over at GMB. I'm pretty sure he leaves you a voicemail and he says like you're their number one, you're number one on their list. And you ultimately go to GMB, a decision you said kind of shaped your career. What did you learn from Neil Bloom about what to do and what not to do? Well, a number of things. I mean, Neil said you can spend all your time on a 20 million dollar deal or 200 million dollar deal. You might as well spend time on the 200 million dollar deal.

10:52Neil also said that there's someone who always has all the money in the world and they always buy the best stuff. The best stuff always has a market. Fioso was very creative. He'd look at lots of different things. And I would say that Some people find a way to know, and Neil found a way to yes. I think it's super important that there's always something to do if you look for it, you know, wait for it to drop in your lap. Neil was a perpetual bull, at least at that point. And I think he liked to hold things too long. So I learned I should sell faster than Neil did. and I think we have. We don't really fall in love with things.

11:37The other thing, I think there's some other things I learned that are, you know, I learned when I started Starwood, I did a lot of things differently. We kind of don't take, we won't make much money if our investors don't make money. We have a management fee. We've had a management fee since we started the firm back in 1991. But that's it. There's no acquisition fees, financing fees, advisory fees. You missed it. You didn't read the prospectus, close enough fees. So I think that served us really well, was basically aligning our interests with our partners. And so that three decades later, I guess it's more than that, that's our hallmark.

12:17Remember, it really changed our fee structure in 30-something years, 33 years. So it's quite simple. Other firms take acquisition fees, and we choose not to. Some firms take financing fees, we choose not to. Then you can make a lot of money ahead of your LPs. So, you know, I think also one of the things I tried not to do, institutions think one way and entrepreneurs think a different way. And I think Starwood, I tried to, when I started, I did everything different than institutions did. I bought assets in Greenville or Colorado Springs, but not in Denver. I bought in San Antonio, not in Houston and Dallas.

12:55I avoided the institutional cities and went where I thought I could get better returns. The fundamentals of the markets were better. They just weren't institutional in nature. Eventually, they became that way. When we went into the single family for rent business, when we bought and created a public company, sold its invitation homes, today we own 17 ,000 single family homes for rent. There was huge noise in the marketplace. Sam Zell was telling everyone he could talk to that this wasn't a business. I'm like, looks like a pretty good business today. I was open-minded about it. I said, the margins look to be the same as multifamily.

13:29How is that possible? because they're disparate houses, but you got pretty good with the technology of how to service them. And the margins were similar. So as long as he kept saying it wasn't a business and we were making a lot of money buying the homes and running them. So, you know, I think Neil was really a guy who's conventional wisdom. And, you know, I think that that was important. And just the sheer creativity and willingness to do stuff. You know, I think both in my profession and my family office, Because I think I have a pretty high tolerance for risk, but by no means do I think I'm a cowboy.

14:02And I'm balancing. I think at J &B and today at Starwood and in my family office, you have your investments that you consider to be home runs. Not every deal can be a home run. It's really about hitting singles and doubles and then have a few alphabets that can pay off big and hopefully don't have tremendous downside. So I think Neil also, one thing that I also learned from JMB, but not from Neil, from the M in JMB, which is Judd Malkin, he told me that he signed every wire. At the time, JMB was 10 ,000 people. It was 24 billion in assets. I think it was the largest real estate owner in the United States.

14:39This is the 1980s. And he signed every check over a million dollars. And he actually signed them today. You can do it by wire or by email. And I said, why do you do that, Judd? He goes, I wonder where the cash goes. And to this day, I do the same thing. Any wire over a million dollars, I can sign off in two seconds. But it's the difference between accounting and cash. Like you hear about calamities in your life, companies that report earnings with no cash behind them. And I want to know where the cash is going. Forget about the accounting treatment. Right. And then I can I don't have too many surprises and you can trap movements of cash to things you thought you were not doing anymore, like consultants and things like that.

15:22So I think those are the steps. So I learned also hard work paid off. You know, I got there. I went off piste. I would find deals in my afternoons and evenings for the company to do. I read about the takeover of a company called Amfac by Odyssey Partners in New York City. And I did a little work and lo and behold, Amfac owned a lot of real estate. Owned to Sugar Mill, owned a department store chain, owned a wholesale drug distributor. But beneath that, it was the largest owner of land on Kauai, the island of Kauai, and had some really good real estate assets. And I thought, you know, we could buy that asset.

15:58And we figured out how to finance it through a syndication with Merrill Lynch. It was pretty successful for Neil. And we had just done a deal with my friend from business school was selling Arvita and a Walt Disney company. He was working in the strategy group. And I called him and said we could buy it. And we called the guy at Merrill Lynch. He said he could finance it. And we issued what were called COLAs, or Certificates of Land Appreciation. we're 50 50 over a four i think with the public it was an amazing financing so i learned about assets and financing um and i brought them deals so i became the top top 10 partner within three years of joining the firm and it was only because i didn't just i found deals for neil and i became neil's favorite son and we made a fortune or he made a fortune i made a little bit of money It's one of the reasons I laughed.

16:52But, you know, he made a lot of money on the deals, including a$40 million upfront fee on a deal that I brought him. It was a$400 million deal, so he took a 10-point fee. So I think, you know, look, I learned an awful lot. And the most important thing I learned from Neil was I made a big mistake. And we were buying a company in Europe. At the time, the richest family in the world was not Zuckerberg or Elon Musk or Bernard Arnault. It was the Reichman brothers in Canada. The two, they owned all of Canary Wharf. They owned all the buildings in downtown New York. And they were like the Lord, Neil.

17:33He revered them, and they thought they were the smartest guy. And by financial statements, they were. And so they went into London and were building Canary Wharf, and they were buying a company called Rosehow, and their sister company that was 50-50 with Rosehow, came on the market and was called Ransworth. They weren't 50-50 with Rosehow, but the Reichmans were getting very long at the UK, and Neil thought it'd be great, and we were, Goldman Sachs called us. I wound up on the deal in 2009, and I lead this acquisition in London of this company, And Neil thought, you know, we could raise about a billion-dollar transaction.

18:15We would raise$300 million or$400 million of equity and borrow$600 million of equity and borrow$300 million or$400 million. We misread the institutional market. It was really early for U.S. investors to go into Europe. And we could only raise$300 million. So they put like$700 million down the company. The problem was the interest rates were wickedly high, double digit, like 14 % we financed that. And the underlying assets were yielding six. So immediately, and I actually, as soon as Neil tinkered with the cap structure, and when we didn't raise the equity and put the debt in place, since the leases were flat and upwards only, you could see the interest expense and the lease, the rental income crossing, and we were going to go broke.

18:56There was no question the day we closed, that deal was going under. So I went in to say to the guys, like, you got to recap this. They said, we can't. We just closed. I said, well, you can go now. You can go later. you're going to have to recap it. So they waited. And then two years later, they did a small recapture, but it wasn't enough, and the company failed. And there was a second transaction that was referring to this sister company. It was called Rosehow. And we were going to buy that for our own account because the Reichmans had bought the sister company called Stanhope in their account.

19:28And this was the second trade. And the deal hadn't gone bad yet. But I walked around and during my due diligence on randsworth and and then subsequently on rosewood uh rose how i walked around the city of london i looked at all these buildings and said that's an awful lot of supply and and then i went back to my room and i looked at the pro forma and rents had to grow like nine percent a year for us to make the numbers and i called neil who was on vacation in tucson um he had sent over his closer the head council from the and i said you can't close this deal he was going to do this deal in his own account and even though he said to me the first time when we bought Ransworth, he goes, if you don't think rents are going up, you know, in England, you shouldn't be in this business.

20:06And I'm like, okay, you're rich. I'm worth$10. He's on the Forbes 400. So he was smart. And I, this time I stopped him and probably saved him from losing a significant portion of his fortune at the time. And I, so it taught me to speak up, like, don't, don't be shy. Like you have, you have a feeling of data, like, and the second time I spoke up and that really, you know, ran worth failing. So I think, of course, it is obviously often said you learn a lot more from your failures than from your successes. And I think I've said this repeatedly, you have to keep your intellectual humility, particularly when you're successful, and not get lazy and don't do the work you do when you're broke.

20:51So it's really hard to do. It's a very hard discipline. And frankly, we've bought stuff from very rich people who go nameless who had taken their eye off the ball. And they didn't understand what they were selling us, but they were skating up here. And we were down here in the weeds and we knew what we were buying. And our rental growth of what we bought and rental growth of what they kept, I think we 2x them. We grew twice as fast. But he hadn't paid attention. And that's the opportunity sometimes. And then when the journal or the other papers write stuff that you know actually is wrong, that's like the time to run there.

21:25But if people don't know what's actually wrong, they use the papers as the facts when they're actually wrong. So, you know, I think we try to be contrarians and try to do stuff off mark, try to create your own opportunities. So anyway, enough on that. You leave JMB at the age of 31 after the SNL crisis. And then you someone related to the Bass Brothers, who I think you met while you were interviewing with them, says they'll back you. Neil Bloom backs you. The Vanderbilt family backs you. The Ziff Brothers back you. You raise$21 million. You go on a buying spree. You buy 513 apartments in Colorado Springs for$3 million.

22:04Then you buy 8 ,000 apartments across the span of 18 months. Sell them for Zanzel for 3x the money. Return your investors 3x the money. Tell me about the early days of Starwood and what's the story about the early days of Starwood that you haven't told anyone yet that you can tell us? oh i so i mean i i spent a lot of time at jamby doing corporate deals so one thing i never did was buy a stick garden apartment building i never bought one so my first thing is i think i'm from i went to harvard business school and the most important thing you remember is you know nothing so i i think that real estate is so local that i called up some people that i knew that that jamby had actually partners with the guy in denver who's local to denver and i he had i had him tour me through the market and tell me what the good neighborhoods and the bad neighborhoods.

22:51And then we were driving down the highway and he says, well, that's buildings built with T111 siding. And I'm like, that good or bad? I have no idea. But I asked the questions and Colorado Springs, it was$15 ,000 an apartment. I mean, the cost of the apartment building was the cost of the appliances. That was the opportunity back then. We were buying so cheap versus replacement costs, but we create our own luck. We just did the hard work. We actually only invested a million or I think we did a million dollars in that deal. And the Bellsburgs did, too. So we partnered on our first deal. And, you know, and that was and then we kept going.

23:32We got very we did a lot of homework up front. We looked where supply was and where demand looked to be. We saw where they would cross and we targeted those markets. So that's how we got to Greenville. And that's how we got to Colorado Springs and not Denver and how we got to San Antonio. And sure enough, rents took off. And then as values rose, we got close to replacement costs and we said we got to sell. So I sold to Sam and helped him bulk up for the EQR IPO. Today, the largest or was the largest resi read in the country, Equity Residential Properties Trust. I went on the board that$20 million was$1 million from Neil Bloom and$10 million from each of the two families you mentioned.

24:08And we called them up and said, we need more money as we were buying those apartments. And they coughed up another 30 or a million dollars, I think it was. So and then we couldn't get any debt. And I guess a little cute story is we went to finally we found somebody who could lend us money. It was Cargill up in Minneapolis. We went up there. They came down and check on us. We couldn't get the money to lease like a copy machine. and then we got a 70 million dollar commitment from carkill we got we're in business um but we borrowed space from the american uh from the ad agency and i borrowed a human being from the ad agency to come and sit in our offices because only three people to bulk us up so we looked like we were more important than we were and i told the people from the ad agency please don't say anything but uh so we mask masqueraded as a five person firm instead of a three person firm to get our first piece of debt from cargill it was pretty funny what do you think was the single biggest risk you took while building starwood and kind of how did it work out look i think going on your own is a huge risk you know i i i was i knew the handwriting was on the wall at jmb you know with the RTC crisis, I knew the company was going to spring holes everywhere.

25:31So I started to look for a job, but I was employed. And it was hard to look for a job while I was employed. And a lot of people, I just felt uncomfortable. Then when the proverbial hit the fan, we're lowering the blinds. I'm going to be dark now. when the stuff hit the fan you know I was expensive and if you want to Judd Malkin who was now in charge of managing all the stuff that Neil Gloom had bought was like going to decapitate Neil's ability to buy anything so I was let go but Neil backed me and I didn't want to get fired again and my boss at the time not Neil another guy was looking was offering me different job opportunities.

Read the full transcript

26:23I interviewed with Marvin Davis, which most people don't know. And he was a tycoon and he offered me a job and I wanted a contract. And he said, I won't give you a contract. He said, if I could fit the contract to one piece of paper, will you sign it? He goes, I guess so. So I wrote this contract that I could never get screwed on. And it was so small and he wouldn't sign it. I wouldn't work for him. I said, I'm not going to take the risk again and get screwed. So, and then I got this offer from a friend of mine to back me in my own stuff. And again, I didn't really know what I was doing. So I think the sign of intelligence for your viewers is to ask a lot of questions.

27:01People who don't ask questions and are fearful of looking stupid, they will wind up being stupid. And you will make mistakes you shouldn't make. It's okay not to know things. And today you have chats so you can ask it anything you want and be smart. but ask questions. Most people would like that. It shows you're interested and you don't know what you're doing. So it's okay. I mean, at some point, if you ask endless questions and you don't catch on, you probably should try a different profession. But asking questions, and I think, I just recently made this speech internally. I mean, our guys should, and I think some of this probably happens in lots of investment shops where other partners don't want to shoot arrows at someone's deal because it's not nice.

27:45It's not friendly. It's not, you know, you're not supporting me. But in fact, you're supporting the firm by improving the investment process, by trying to shoot bullets at it, to try to, you know, ask every question, get every answer. So you aren't surprised that you succeed because of things you thought you'd succeed with. You could, you thought rents would go up because supply would diminish. And then, you know, when you get lucky when yields on property fall because interest rates change. So a couple more things about lessons learned. I mean, hope's not a business strategy. You have to make your own hope.

28:20And luck is when preparation meets opportunity. I was accused of being lucky when I created Starwood Hotels the first time our Hotel Investors Trust and then became Starwood Hotels. We worked our butts off and we were able to get a stock that traded a huge multiple, which I can then use as an acquisition vehicle to build the largest hotel company in the world over three years part-time while running Starry Capital Group. So, yeah, I mean, Hilton was there, and Hilton, unmarried, ultimately went to Washington to keep us from growing and get rid of our structure. But they weren't in the game, and we were disciplined.

28:57While we worked really hard, we didn't overpay for stuff. We had a little twin company that was born after us called Patriot American Hotels, and they kept outbidding me over and over again. And I was like, and the market loved it for a while. They love the action. Their stock flew, but they were overpaying. And when the geese came home and they couldn't buy anything else and people looked at the financials, they blew it. And the stock company went bankrupt. So you got to have a long-term view and you got to stay disciplined. And it's probably really good advice for the markets today, by the way, because we're in a chapter of investing that they don't teach at any business school in the country.

29:34so it is it is not um fundamentally driven it is not this is not cash flow growth this is uh we're definitely moved into the casino society so we'll see how this works out but it's definitely a different time i watch a lot of podcasts with you and you mentioned that you had a lot of executives that didn't work out that weren't loyal and you spent over 20 years trying to find kind of the right team to surround you what do you know about talent now that you wishing you 20 years ago Well, I think, I mean, you know, we companies, not my company, all companies grow at a pace. And you go from the minor leagues, the major leagues to trying to win the Super Bowl.

30:17And some of your talent can go with you and some of it is capped out. And sometimes, you know, and then as people get older, their priorities change. I mean, investing is a hard business and you have to stay in the game. Otherwise, it's just potluck. and you might just go to Vegas, you know, and have the same odds. So you have to stack the deck in your favor by doing the work. And I think, you know, everyone loves to get lucky, but, you know, I could get hit by lightning. And it happens in investing too, but that's not a way to run your life is throw, you know, hope, stand under a tree and hope you get hit by lightning 50 times.

30:53But you do have to have chips in the table to get lucky. You have to be in the game. so and that means you're going to make a lot of mistakes but you there are the mistakes are all learning opportunities and hopefully you you structure them in such a way that they don't devastate you they don't wipe you out so I think um in hiring people I think you know when you grow really fast sometimes you know you you take an athlete above their capability sometimes you aren't building the depth in an organization you need. Sometimes people's priorities change. They've made enough money or they have a personal issue at home when they decide they want to do something else.

31:34I think building depth to an organization, as it goes, obvious is really important. I think if you've seen my podcast, I think one of the CEOs on the firm told me when I was running Starwood Hotels, he goes, like, if you keep bad actors, you're doing the whole firm a disservice. and you're setting a standard because he'll say, oh, that guy gets away with it or she gets away with it. And so you think you're being nice to that person and you don't want to be a tough guy to fire them. It's really hard to let people go. I'm sure you're too young to have watched all the Seinfeld episodes when George Costanza fires people and you burst into tears and everything and people line up to get fired because they want to see how how emotional he gets.

32:12And then he gets numb from all the firing and he stops crying and everyone's furious at him. I mean, firing people is difficult, especially if you know them and they've been with you a long time. In my business, they've had kids or they got kids in school. But our loyalty at the top has to be to our business and our fiduciary duty or our investors or we're just not going to survive. So it's hard. I think the one thing most people agree on is the no asshole rule. You know, culture is a big deal. And if you see somebody, but it's there's much more nuance than that. People aren't working that hard.

32:47They're making it. I make a big distinction between pilot error and mechanical failure. I kind of like crises. They organize everyone to focus on the stuff that really matters. And people band together. When 9-11 happened and our cash flow at Start Hotels dropped from$1.6 billion to$937 million, we had a crisis on our hands. We got rid of all the superfluous things we were doing and focused on things that really mattered. And everybody was hand and hip. Same thing happened in the pandemic for us. In Star Property Trust, we just made it. We batten the hatches down and got through it. Now Star Property Trust, the nation's largest commercial mortgage rate, which started as a blind pool in 2009 from an idea I had.

33:30We raised$900 million in the New York Stock Exchange. Today it's a$20,$30 billion company,$28 billion company. It's the only mortgage rate that's never cut its dividend, and it's the only one trading above its IPO price. And I think we've paid out a total return over 13 or 14 years, like 11 and 12%, which would be most any hedge fund. And it's listed. And right now it trades like a 9.6 dividend yield. So, you know, and we did. I was pretty careful up front to diversify that company because I know you can't force capital into one sleeve and hope that it will be safe forever. So we continue to diversify that company.

34:07And it's interesting. I keep hearing the analysts don't like us. I said, I don't really care. I'm going to build a resilient company. They can buy the stock or not. I'm OK. Vote with your feet. But right now, it's doing pretty well. So I think people finding talent in my new role that I'll, as I brought in a press, and I'm going to spend more time finding great talent. And great talent in the firm should want great talent beside them. and not view it as a threat, but use it as a learning experience if they're better or that we will do better for our investors, which means they will do better too.

34:48So it's hard. It's hard in all companies. But I think it's like I consider CEO a lot like an NFL football coach. He's got his quarterback. He's got his line. He's got his wide receiver. And there's chemistry that's super important between the receiver and the quarterback. But if this world-class person shows up that's better than their quarterback, it's their job to go get that quarterback, try to bring him in-house, try to figure it out, try not to lose the chemistry, but win the Super Bowl. So you have loyalty. You also have a stodginess that comes into organizations that stay doing the same thing.

35:25When I took over Starwood Hotels, we were the most innovative hotel company in the world. We've won multiple awards for that. and all the ideas that I think many of which I came up with, but I hired people from Disney, from American Airlines, from Pepsi. I thought we had enough hotel people and I wanted to benchmark that company against the best sales culture at Cisco or the best HR department at PepsiCo, not the hotel industry. So I think you have to benchmark yourself against best in class in each vertical in your company and bring in more points of view so you have a quilt that has more colors.

36:02In investment shops, everybody thinks they want to say what they think I want them to say, like what I want to hear. I want to know why I'm wrong. I don't want to know why I'm right. I already have that. I got that down. I want to know. And it's funny because I will be very, and I talk about this a lot. I have a theory, but it's a theory. And it has to stand all the facts all the time as they change. And you have to want to change your mind. And I think when you're running an investment shop, even when you're running a company, it can be any industry, not real estate, you have to know when you should like when sheer force of will will get something done or when you're banging your head, you know, a square peg in a round hole.

36:41It doesn't matter how long you'll spend at that. I think everyone tries to do things where they have competitive advantage. Also, that gives you conviction to win something. You know, it's not like you can't be conservative on 10 variables underwriting a business. If somebody is going to use their knowledge and get aggressive on one and you're going to be, you know, and I don't think you've done anything like I don't think that's good. I don't think you can be the greatest person in the world. But if you are you won't win it, you won't get the deal. So you need to come with some thesis and some background and have conviction, which is true if you're playing golf, tennis, a sport or in the business of sport.

37:21But keep your mind open. Keep your head open to new variables and new data that might change your thesis. And you might go from a hold to a sell or a hold to a buy more. you know so i i tell a funny story that years ago we were having a uh asset management meeting and our portfolio in denver our apartments were yielding like 18 cash on cash and we probably underwrote eight so they were and they looked at me after they told me this and they saw i was kind of like really unhappy and they said why are you unhappy this is so great i said why didn't we buy 30 other properties there we had the information you should have told us that we were crushing are underwriting and we should use that information to run back in the market and have conviction and buy five other things so i think when you can tilt the playing field in your favor with unusual data or work hard work i think you know my success i've worked really hard you know it's not nobody can say that i i travel and read everything i can read and get my eye and i'm constantly looking for new ideas and new opportunities.

38:27And I, I try to be super creative, you know, and, and perseverance is genius in disguise. Like I will, like you, like you kept coming at me and now you have a podcast. So, but you know, I respect that. And I admired that in you. And I think I, and there's a, there's a right way and not a right way to do it. I mean, you don't want to be obnoxious, but you get a lot out of trying hard and, and working hard. You really do. the world pays off for hard work it does and one other thing which somebody said to me when i was young the world um is it's a fair world out there you get 24 hours a day everyone does and how you choose to use them is up to you so and don't be upset like by the way if you want to make forty thousand dollars a year and you know have seven hours a day to play other things it's totally cool.

39:17It's up to you. But don't, you know, you can't, can't expect to have built a lot of wealth for yourself working two hours a day. So like, that's up to you. It's all good. But you know, it's a fair world. So I take that to heart. Yeah, your point about talent really resonated with me. I mean, I've had some experience, even though I'm young, I've had some experience with talent. I had a, I had an executive assistant, I bootstrapped a business, I had an executive assistant at 14 for no reason, which is a little funny tidbit. But you've closed hundreds of billions of dollars worth of deals. And you're known as a really talented dealmaker and negotiator.

39:55What are some like kind of keys to successful negotiation? Well, you asked me about Neil Bloom. And early on in my career, we were walking into a, we were going to buy Universal Studios, Lou Osterman, the legend. And I think it was that trip where Neil looked at me and says, you know, it's time to be proud and time to grovel. because you got to know when you got to do which. And then he said, you know, you also have to learn to walk away. Like, and that's one of the hardest things to do in deals is walk away and be firm on your pricing and don't, you know, don't change your assumptions to justify this higher price you're paying.

40:31Like, that's silly. So, you know, I think about negotiating. Everyone has a different negotiating style. I think it's a hard thing. You want to buy something. Where do you start? Like you don't want to offer more than the guy wants for the asset, right? Or he may be willing. I think another thing you see in our business, you learn is people have investors who require different rates of return. So my investors want a 20. If I'm competing with a guy who wants a 10, he can outbid me. So, you know, he's not stupid. He's not a dummy. He's just got a different source of capital. That makes him quite smart.

41:08And they're comfortable with that asset at a 10. So I think I try to do deals and be reasonable from the start. I don't start with crazy ass or ask for crazy prices, hoping I get 80 cents on the dollar. And everyone's different than this. And I think the same is true in budgeting your company or budgeting your business. It's an art form. Like, do you set a goal? And I fought with a fellow I hired to run Starwood Hotels early on. he would set impossible annual budgets. And I said to him, why are you setting budgets like this? They can't possibly hit them. He goes, I know that, but they'll be within 80%.

41:48That's still better than they would do if I let them budget themselves. I don't adhere to that philosophy. And if you're going to use that philosophy, you better have some mechanism in the year for the year when they see they're missing their numbers to know that you're still in the game for the year. Otherwise, they've lost the incentive to perform because they're not going to make budget and they know it. So I think my goal is to give something that's achievable has to be measurable and uh and people can hopefully make uh you know can can can then hit the targets they need i think i think deal making is really an art form and i think the other key to negotiation which is people talk about all the time is making someone else feel like what you want is their idea i think one thing i also learned from neil in a really interesting negotiation with the walt disney company when we're buying this company from them But his style, he asked for some crazy stuff.

42:40But we were deep in the negotiation. And it was the equivalent of one and one is three. And he's arguing. And I'm there. I'm 28 years old or seven. I'm looking like, are you an idiot? Like, do you really think one and one is three? And the chief counsel of Walt Disney is turning the color of a bell pepper. You know, the president of Walt Disney was Frank Wells. He's screaming at me. I'm sitting there like, this makes no sense. And I walk out with Neil like, Neil, that's one and one isn't three. The one and one is two. He goes, I know that. I'm going to give this point away so I can get everything else.

43:13So, I mean, there's different styles of negotiating. And I think, you know, I've seen a lot of different styles. I think it's most important to know who you're negotiating with. Yeah. And how do you make them win? What do they need? And can you get them successful? I had a guy who was a lawyer work for me. he was a brilliant guy but maybe the worst deal that I've ever seen because every point was of equal importance to him and in reality only these three were important the other 17 didn't matter so focus on the ones that matter to you and recognize the relative importance of these issues in a deal and make sure you get the ones you need to get or you can't do the deal and the rest are kind of negotiating bait and realize that the other person And it's a deal is a relationship.

44:04They're going to get called later in your life as a reference. You don't want people to say you were, you know, an asshole. I think also another thing I picked up from JMB, there's a very famous guy that worked there. He really negotiated the other side to the bone, like to the bone, like he left no meat or skin or anything. It's just the bone. I don't try to do that. You know, I don't I don't whether I get that extra million dollars off the deal. It's not going to make a difference in the deal price. and the deals performance ultimately. So I don't try to, now we find issues like the roof is caving in and we didn't underwrite that.

44:38That's not a price cut, that's due diligence. But if we want to go back and say, hey, I want 5 million off the price for no reason. I mean, that's something I try not to do. And we couldn't be as successful as we've been over three decades if we retraded people on deals all the time. And for a while, our competitors were saying we were doing that, even though we weren't. And I kept saying, well, how do you think I did? I bought 700 hotels. Well, we owned over 120 ,000 market rate apartments. We have the largest number of apartments in the country. Today we have the largest number of affordable units in the United States, 53 ,000 units.

45:13But our market rate book is down to like 50 ,000 units down from 120 ,000. So you don't buy all this stuff if you wind up retrading everyone. That would be a, your reputation would precede you and you wouldn't get any deals. Quite the contrary. We'd come in second and third and a bid and they'd still close with us because they know we'll close. So that's one of the benefits of being in business a long time. I have a couple unrelated questions to investing for you. You're obviously very focused on design. What does great design mean to you? What does it feel like? I'm a you're on a really important subject to me personally, because I think, you know, what matters in real estate in particular is what's happening to the asset.

45:55I look out my window. I probably have 40 analysts and associates sitting at their desks. They're doing performance that are meaningless. It really matters what's going on in the property. What what the financials that come into our offices that we model off are a result of what's happening at the property. So if you put the trash bin in front of the leasing office or the pool furniture is a mess where there's no fresh flowers or the flowers are dead, you're going to have a problem with your occupancy. And it's not you're not computer is not going to fix it. It's what happens to the property. And I, you know, I built my career on design matters.

46:26I created W Hotels out of an idea that you could have a cooler hotel, not the coolest hotel. It was never supposed to be even Ian Schrager's hotels. It was supposed to be, I call it the staff at W Magazine, not Kim Kardashian. Because Kim's not loyal to me. She'll be at every new thing that opens. And I want to build a loyal crowd. So I think design matters. I think today design matters more than anything. I think you're appealing to an affinity group, a group of people. I think the K car, which was Chrysler, they built a car in a single chassis and it was a huge failure. You can't do that. You have to pick a niche and own it and be true to that and then gain authenticity in your niche.

47:10And then if it's a big enough niche and you do it well enough, you can price against that and get some loyalty and some pricing power. And when I started W Hotels and the guys would come back and say, oh, we're$10 ahead of the Marriott and$10 ahead of the Hilton. I'm like, well, we're not competing with Marriott and Hilton. We're a different crowd. People want to stay with W or saying something about themselves. Try 50 bucks. and that would hold. And that's now with one hotels, we see the same thing. We built a hotel in Brooklyn here in New York. You know, the room rates, when we were bottling it out, the guys were telling me, hey, Sheridan and this other hotel, they're doing$280 a night, so maybe we'll do like$320.

47:48I said, it's irrelevant what the neighbors are doing. We're going to build this great building, brand new, with incredible rooftop and a pool overlooking the skyline of Manhattan. Today, we averaged$780. You know, the guys are still$300. So, I mean, I think sometimes this is sort of an art form, but design does matter. What you build, and you see it today in the office markets, the best buildings are full. Buildings that I built a building in Miami during the pandemic in a market that most people thought was pretty full. And we leased the entire building with no leasing broker during the pandemic.

48:22And it was 100 % full. I leased it by myself because I built the best building in South Beach. and I knew people that wanted to be in the building and I built the right product. That market was small tenants and I have 10 family offices in the building. So, you know, I think it's really, really important what you build matters. But don't fall in love. Like, don't be stupid about it. Don't like you see guys. I don't care what everyone I'm building the nicest building. You still have to get the math right. You have to get the cost versus the yield. Right. And a lot of times, if you get lucky, like the one South Beach today, we thought we'd get$600, but we built a really good hotel and it gets$1 ,000 a night and nobody's pissed off.

49:06So, you know, I think design, and to me, it's all senses. It's color, texture, sound, smell, everything. It's everything. You got to work on all the five senses when you're certainly in the hotel business and in the rest of real estate. I think it matters. I really think it matters. We've renovated many of our apartment buildings. I took one building in Aventura and I gutted the units. And if we fixed them up, we doubled the rents. So we're good. Some people are really good. We're good. We're not great. We could be better. Everyone could get better. I want to ask you kind of a question that's different than a lot of the questions I'm asking you.

49:50And then I have two more questions left for you. but I know you're Jewish and I know you're involved in the Jewish community. How did your, I'm half Israeli and I'm also Jewish. How did your perspective on the world change after October 7th? That's quite a pivot. Well, immediately, as you know, I started this social media movement called Facts for Peace to try to convince or teach people who Hamas was and what they called for and that they weren't a partner for peace ever. The world seems to have lost the narrative. I mean, they call for the destruction of Israel. And so I don't know how anyone could ask for a Palestinian state that's led by a government that doesn't recognize Israel's right to exist.

50:35So would I like a two-state solution? Absolutely. Is it probably the only solution that works in a bad situation? Yes. But then you have a government that recognizes Israel's right to exist, and then Israel will recognize the Palestinians' right to exist. if they spent all this money on building resorts, hotels, and creating jobs rather than buying missiles and cutting up water pipes to create missiles to fire at Israel. I thought that for me, that was my call to action. I thought I cared. I had a history. I've been to Israel as a kid. And again, a couple of times as an adult. So I thought I've been successful to help with something like that.

51:15And we've had a billion views of our videos, though it's hard. The world is poised really aggressively against Israel. And I was recently offshore. You watch CNN International and you watch CNN. And CNN International is virially anti-Israel. And CNN is mostly anti-Israel because it fits in with the left narrative now. And nobody seems to be upset about the children and the women dying in Ukraine. They seem to be dying. And they didn't start the war, the Ukrainians. And all that has to happen, they tell people that all these tunnels in Gaza, when the Nazis bombed London, Winston Churchill put the populace of London in the subway tunnels.

52:01Those tunnels could have been used for the women and children of Gaza. And instead, they left them on the surface, put Hamas soldiers in the tunnels. And they wanted them to die so they could get world sentiment. and they don't care about life, but they say that. They're martyrs in a cause. So it's worked beautifully for them. Obviously, it was the ignition of the October 7th massacre was the fact that Israel was going to probably sign a peace treaty with Saudi, which they couldn't have happen. And it's interesting that Arab countries have said that Hamas can't stay, but the Europeans don't seem to have that point of view because the Arab nations know they're not a partner for peace.

52:41Can you just take that off for a sec? And so I think, you know, I don't know. I don't think I'm not a fan of Bibi's government. And I think Israel does a really bad job of talking about all the good stuff they do. But, you know, I do know that this is the explosion of anti-Semitism is something that I never thought I'd see in my life, in this country at least. And a lot of it's born from ignorance, which is why I did the social media program. And we targeted persuadables. I mean, 10 percent of Americans think the Holocaust never happened. So they're not persuadable. I can guarantee you the Holocaust happened.

53:23My father is living proof. And, you know, now you have this revisionist history on Hitler was a good guy and Churchill was a bad guy. So it's scary. How could you say anything else? And, you know, a lot of this stems from a world where family and values and what's right and wrong is kind of getting all mixed up. And it's very distressing. I choose to believe it'll be OK, but super, super rough right now. Yeah. Yeah. I just wanted to hear your perspective on it as a young Jew and a young Israeli in the United States. And I want to end on a little bit more of a upbeat note. this is a very very different question but it's probably the second most challenging question i'll ask you today after the last one but if you could only stay at five hotels for the rest of your life i can't name those i probably haven't been there there's uh some places i've been that were great as um all tudor jones owns a hotel in uh tanzania which is uh outrageous um it's And then I've been to the Sengita Resorts in South Africa.

54:34They were terrific.

54:38You know, I've become a bit of a snob on hotels. They really got the extraordinary to totally impress me. Are there any others that were, like, mind-blowing? It's interesting. I think that the Amman in Tokyo is pretty amazing. has a lobby that probably cost, you know,$6 billion, given all the space they gave to Iraq.

55:04I'm thinking, we have to come back to you on this. It's, you know, let me think.

55:17There's a lot. I mean, I could pick my own hotels, but I won't. We still own the Creon in Paris. it got renovated it's beautiful they did a lovely job um there's a hotel in mallorca um wait on the point now um i've got the name of it roca rocco rocco it's pretty cool it's an old it's an old uh la residencia there's a belmont it's beautiful um but don't put me on the spot because i'm gonna i'm gonna you know i like to tell you all my hotels then i can i can tell you that The Baccarat in New York, which I built. I'll go, that's a really nice urban hotel.

56:01But I have, I don't know. I got a lot of hotels I like. I'll check out the lobby of the Baccarat next time I'm in the city. My final question, I end off with every guest with this question. This has been an incredible interview so far, and I first want to say I really appreciate you coming on. But if you had to give one piece of advice to a 15-year-old today, I'm 15 and turning 16 in four days, what would it be?

56:25I mean, my entrepreneurial finance professor said, find the freight trains in your life and get on them instead of in front of them. So think about what those freight trains are. Today, AI and how changing the world is going to be one of them for sure. But I think don't take shortcuts. like basically be willing to walk the walk and don't don't take a shortcut build a strong foundation for whatever it is you want to do in your life and career i've just read barry diller's book who i've known for 25 years and he talks about working in the mail room and how he went here and he was this guy's assistant that guy's assistant i was basically that that person i i licked i licked envelopes in a mail room you know in the summer years so just do the work like don't Do the shortcuts to understand the building blocks of what it is you're doing.

57:20Learn as much of the variety of roles that it takes to succeed in whatever it is you want to do. But spend the time, especially when you're your age, because it's not about money. It's about acquiring skills. Money will come later. And then again, if you're fortunate enough to get into something you love, then it's not even work. And for me, design does not work. I love it. It's a creative outlet for me. And it gives me peace. I enjoy design. And the fact that I'd marry it with a financial skill so I know what I can spend to get a decent return for my investors, that's the holy grail for what we do.

From the publisher

This week on Generating Alpha, I’m joined by Barry Sternlicht — founder, chairman, and CEO of Starwood Capital Group, and one of the most accomplished real estate investors ever. Since founding the firm in 1991, Barry has grown Starwood into a global powerhouse with over $100 billion in assets under management, investing across every major real estate class. He has created and managed more than 80,000 hotels, multifamily, and residential units worldwide, while launching iconic hospitality brands like W Hotels, St. Regis, and 1 Hotels, redefining the way design and brand intersect with real estate.


Barry’s accomplishments extend far beyond hospitality. Under his leadership, Starwood has executed transactions totaling hundreds of billions of dollars, spanning hotels, residential, office, retail, and industrial properties. He has been recognized repeatedly as one of the most influential figures in real estate, known for his contrarian eye, his ability to anticipate market cycles, and his pioneering focus on sustainable development years before it became mainstream.


In our conversation, Barry reflects on a childhood shaped by resilience and early entrepreneurial ventures, the pivotal lessons he learned working under Neil Bluhm at JMB, and the rise of Starwood Hotels. We also dive into the biggest risks and near misses of his career, his philosophy on evaluating deals and negotiation, and the timeless advice he’d give to the next generation of leaders and entrepreneurs.

More from Generating Alpha Podcast

All 47 episodes
Episode 32: Barry Sternlicht - Chairman and CEO of Starwood Capital GroupGenerating Alpha Podcast · 58 min
Listen in VO