How Courage And Consistency Close Deals With Henry Stimler (Podcast)

Henry Stimler serves as an Executive Managing Director on Newmark's Capital Markets Strategies team, where he specializes in originating and structuring in multifamily debt and equity with an emphasis on large bespoke portfolio transactions. Based in the firm's New York headquarters, Stimler is known for guiding traditions Tri-State investors into new high growth markets across the U.S., including the Midwest, Texas and South Florida, while also sourcing global equity from key international cities like London, Tel Aviv and Johannesburg. Prior to joining Newmark, Stimler founded and served as Director of London Green Capital, a debt origination firm.

Insights from Henry Stimler on How Courage and Consistency Close Deals

Henry Stimler runs a full calendar. Client meetings, travel, prospecting, closings, and pipeline follow-ups take up most days, yet he still takes calls from young professionals, makes time for anyone genuinely trying to learn the business, and sees mentorship as part of the job.

That mindset was shaped by starting from zero after the 2008 crash. He went from a thriving business to being overdrawn at the ATM and had to rebuild his career piece by piece. It taught him to focus on real opportunities, protect his time and rely on a team where everyone brings a different strength.

In this episode of The Dealmakers' Edge, Aaron talks with Henry about rebuilding from the ground up, sourcing and structuring large multifamily transactions, and keeping deals on track in challenging market conditions. Henry discusses rejection, resilience, mentorship and what it takes to close complex deals.

1:50 – Henry's background growing up in London and leaving the traditional path

2:35 – Discovering an arbitrage opportunity and building Phoenix

2:50 – The 2008 crash and losing everything, including assets and business

3:20 – Rebuilding through club promotion, opening venues, and returning to finance

3:53 – Turning a shuttered Chinese restaurant into one of NYC's hottest nightclubs

6:12 – Closing his first deal and earning a $25K commission before his son was born

6:21 – Transition to Newmark when Cantor rolls platforms together

7:03 – Building a national platform and taking NYC investors into new markets

7:57 – Success is not linear and why connection skills drive outcomes

10:51 – How to spot time wasters and protect your capacity

12:12 – "Fish with a net" and why small maybes drain time

14:24 – Making time for students and early-career outreach

16:35 – Keeping a billion-dollar pipeline moving toward closing

18:53 – Team structure in practice and the yin and yang with Bill Weber

21:32 – Developing junior talent and the cold outreach that led to a $230M closing

29:02 – The perspective and humility carried forward from the 2008 crash

Mentioned In How Courage and Consistency Close Deals with Henry Stimler

Transcript

Aaron Strauss: You're listening to The Dealmakers' Edge with A.Y. Strauss, diving deep into stories behind commercial real estate leaders. Hello, everyone. Welcome to The Dealmakers' Edge. Today, I'm excited to be joined by Henry Stimler, who serves as Executive Managing Director at Newmark, where his core focus is on origination and brokerage in multifamily debt and equity, with a particular emphasis on large bespoke portfolio transactions.

Henry has done a ton of large deals as of late, the last several years. He talks about his unique style, his pacing, and his deal flow—how he originates deals, how he asks for the business, how he's built his team, how he manages his extremely chaotic calendar, and how he deals with the emotional ups and downs of dealmaking. It's a very exciting episode. You'll get a front row seat to a prolific dealmaker, and I hope you enjoy.

Hello, everyone. Welcome to The Dealmakers' Edge. Today, we are joined by the one and only Henry Stimler, who I've gotten the pleasure to know a bit and who is extremely prolific on every level. The consummate dealmaker seems to be closing every major transaction out there at a high level these days. You see his postings, you see his announcements. It's really incredible what you're doing in a weird, softer market.

The success you've had to date—I know it wasn't accidental. I know your background is unique, but I think our listeners, for those who don't know you, will be excited to hear your story and not only hear your story, but to learn from you. Everyone's looking for that edge. That's what this podcast is about. So maybe you could talk a little bit, we don't have to get into depth, but about your upbringing. I know your background was certainly not traditional as far as going into finance early on. Fast forward a little bit until you got into commercial real estate at present day.

Henry Stimler: Thank you for having me here. Nice to see you as well. I'll give a really quick two-minute background. Born and raised in Golders Green, London, which is a lovely provincial part of London, very orthodox Jewish community, very insular community. I was meant to follow the path of everybody else within that community: go to school, go to yeshiva, get married at 20, settle down, live three blocks from your parents, spend every other meal with them and your siblings, and just live in the same bubble that everyone else did.

I was a little bit different. I didn't want that for myself, so I left and came to New York at the tender age of 22 with a dream and a few hundred dollars in my pocket. I slept on an air mattress at my friend's apartment on 96th and Second on the fifth-story walk-up. I got an internship at New York Life, was at the internship for maybe four or five days, discovered an arbitrage, left the internship, and went on to build a company called Phoenix, which was busy in the arbitrage.

That became very, very successful. At the age of 24 or 25, I was making money hand over fist. It was an unbelievable time. And then the crash of 2008 came along, and I was completely destroyed by that crash. It took everything from me.

From being at the height as high of having all the cars and the planes and endless money rolling in, I now found myself at the age of 28 back where I started. I'd since moved from my fifth-story walk-up to 65th and Madison, left that, moved into a tiny studio at 15 Park Row, and had to reinvent myself. It took me about two years to wind up the business. I was looking for something to do.

I started to do parties and promote at different venues. I'd always been surrounded by a lot of people. I'm a little bit charismatic and fun, so it seemed like a natural fit to be a bit of a promoter. Venues would pay me to come with people. It was a quick way of making money, so I started doing that. Then my friend told me he found a venue and needed $15,000 for a sound system. Would I lend him the money? I said no, I'll invest with him.

We opened our first nightclub called Madame Wong's, and it just became an overnight sensation. The New York Post, New York Times—everyone covered it. So strange. We took a crappy old Chinese restaurant and turned it into the hottest nightclub. It just shows you that people spend millions of dollars building out these elaborate places, but in essence, if you can create something, people will go anywhere.

This was a really disgustingly old Chinese restaurant. We hung up Chinese lanterns, made it dark, lit candles, and just rocked out. I got bitten by the hospitality bug. Over the next five years, I went on to open three more venues and a restaurant called Jezebel that was pretty short-lived.

In 2015–16, after doing this for five years, my then-girlfriend, now wife, said, "Enough of this. I met you when you were a finance bro. You've got to go back to being a finance bro. This is not conducive to the lifestyle we want to live. We want to have kids. You've got to go back and get yourself a job in finance."

I was ready. I was tired. I was tired of being out babysitting till four or five in the morning. I was ready to move on. So I tried different things. I capitulated. I went to work for my father for a few months. I didn't like that. Then she said, "Go see Anthony Orso at Cantor Fitzgerald."

I went to see Anthony. I'd known Anthony through her. He'd always been a very good, supportive figure in her life. I went to see Anthony at Cantor. I said, "Anthony, please give me a job." He said, "I can't give you a job because you're a club rat." Every time he'd seen me, I'd been in different get-ups and in different situations. I didn't look like a real estate finance bro.

He said, "But we just bought this firm called Berkeley Point Capital, which is a Freddie Mac and Fannie Mae lender. You can come in, sit, and learn the business, be an outside correspondent for Cantor bringing us clients." He gave me the card of a recently fired gentleman. He said, "This is the key card. Come in here and sit and learn the business."

So, you know what they say in the movie with Leonardo DiCaprio? "If you're behind on your credit card debt, start dialing. If you're behind on your rent, start dialing." I went in every day, didn't know anything about it. I just started to listen and ask questions. I picked up the phone and started calling people, saying, "Hey, we can refinance your multifamily or we can finance your multifamily here at Cantor with Freddie Mac and Fannie Mae."

It took a lot of time, took a few months, and Anthony was very helpful and very kind to me. He came to a lot of meetings. I put a lot of people in front of him, and I threw a lot of things at the wall trying to make it stick. But I learned the business. I asked a lot of questions to guys that I look up to today—Bill Weber, Chris Mill—the people that were really successful in the business.

I learned the business. I just started calling, and I just had the courage to pick up the phone, to call, to meet. Thank God I closed my first deal a week before my son was born. I got a $25,000 commission check, and as they say, the rest is history.

Then in 2017–18, Anthony got transferred from Cantor to Newmark. He said, "You're coming with me."

I was like, "Anthony, I don't want to come with you. I'm very happy doing this outside correspondent thing. It's working great. Why would I want to go?" I had built this company called London and Capital. I was this outside correspondent. "Why do I want to come with you?" He said, "You're going to come with me."

I went with him to Newmark, partnered with Bill Weber. Bill and I started to build a business. Here at Newmark, you have a lot of investment sales brokers selling products. So we started to act as a concierge for our multifamily buyers who were looking to diversify from New York.

New York was going through a period of tremendous stress with all the rent stabilizations. These guys were suddenly now looking for product outside. So we would take New York buyers to markets where Newmark had brokers in, the Midwest, Atlanta, the Carolinas. This gave us a tremendous leg up.

We started to work hand in hand with the brokers. That was a huge way of driving revenue and driving business because typically, you're waiting with a catcher's mitt for a guy to say, "Hey, I locked up this deal, finance it for me." Here, we were being so proactive. We were pushing deals all the time. "You've got to buy this deal. You should look at this deal. You should go see this market."

We would take people to markets they'd never been to. The platform is incredibly powerful, and we understood how to work within the platform. Fast forward to today, thank God, we will do this year, I think, $4 billion of multifamily. Year over year, we're pretty much at the top, if not the number one, but at the top three multifamily lenders within the firm. We've built out the team. We've got some great guys, and it's been a really good run, thank God, and long may it continue.

Aaron Strauss: It's awesome. You're proof positive that success is not linear. It goes up and down, but the principle, I think, is your motivation, your drive, your ability to connect with human beings, your passion for those connections never stops ticking. So if you're selling nightlife or you're selling very complex, bespoke structuring of transactions, it's connecting to the right people at the right time with the right message.

Honestly, having the British accent never hurts, my friend, too. You've already got a leg up over everybody. But all kidding aside, some of those roots—the placemaking, turning that old Chinese restaurant into a hip place attracting people—a lot of people just lose their mind on the X's and O's of business. But you seem to have that intuitive feel. It's in your DNA of who's the person to speak to, how am I going to get them on the phone, how do I connect with them, and how do I get them to use me?

And obviously, you're on a world-class platform. Ultimately, now your success is speaking for itself. You have the track record. But in those early days of just having that ambition and the hunger and having the strategy—maybe somebody listening to this is struggling in this market or they're pretty junior and they know they'll be successful down the road—what was driving you, obviously, other than survival skills? What kind of voice was running through your head as you're chasing that next deal, getting up in the morning?

This is a tough business. You rinse and repeat every day. We talk about the billions of closings, but there's probably $28 billion that never closed that you had on the five-yard line. So how do you get your mental space together every day to be Henry Stimler?

Henry Stimler: That's such a great question. It's so true. You know that meme of the iceberg where you only see the top of the iceberg poking out of the water, but you don't know how big the iceberg really is? The amount of work and the amount of trial and error and tribulations and failure—it's huge. You only see the closings. You don't see the deals that you spent years and years working on that fall apart.

But I think the most important thing that a young person needs to know that I had to learn very quickly is twofold. One, you need to have courage. I say this all the time to my young guys: you need to have courage to make the approach. That's in everything in life. That's with business, that's with a girl that you want to meet, that's with someone you want to get in front of.

If you don't have the courage to make the approach, it's all for nought. I think that is so critical—have the gumption to go pick up the phone and say, "I want to meet with you. I want to see you. I want to be in the room with you. I can bring something to the table." So many times, people are scared. They're scared of rejection.

I thank God, I say, "Okay, so you get rejected. Big deal." I've been rejected in life, rejected in school, rejected by women. Rejection is part of life, but I've never had fear. So that drive to go and make the approach is huge. Then the other thing you have to know very quickly—who's just going to waste your time and use you as a resource, who's going to drive you crazy, who's just going to use you and abuse you and never give you the business.

In the beginning of my career, I chased everybody and everything, and people would use me as a resource. Ultimately, they would go with their go-to broker. You have to also have the courage to fire people from your life that are just using you. Many times people can't see through that. They can't see this guy is just going to use you and he's never going to give you the business.

So you also have to have the character to recognize who's the guy that's going to give you business and who's the guy that's just using you as a sounding board—using you to double-check the other guy's work, using you to keep the other guy honest, using you to drive down his other guy's fees. You have to not be scared to fire people that do that.

This business—there are a lot of time wasters. I'm not scared to do that. In the beginning, I was, but now at this stage, if I do the work and I've come to you and I've presented a great strategy and I've done the work and I've toured the building, I brought the lenders to the building, and you've burnt me, maybe one time you can burn me. But if you burn me more than once, two times, that's it. I'm never going to deal with you. I'm going to ice you out because you've wasted my time twice. I'm not in the business to waste time.

I always say, I'm not here to fish. I'm not a fisherman. I can't cast a line and hope my bait catches a fish. That's not the way this business works. I'm not fishing with a fishing line; I'm fishing with a net. I need to bring up the fish. So all these guys that cast a line and try and get a nibble, it's not going to work like that. This business is too difficult. You have to be out there with a big net, and you have to reel it in.

So these guys that work on this deal and that deal and that deal—it's a waste of time. You've got to have a big net out there and try and pull as many fish as you can. I'm always saying if a guy has no money, comes to you and says, "I want to buy this deal, but you found me the deal, you got me the debt, and now find me the equity," I'm like, "So what have you done? What have you brought to the table? I found you the deal. It's a Newmark deal. I got you Newmark debt. Now you want me to give you the equity? That's a waste of my time. I may as well buy the building myself."

So you've got to identify the people that are just going to waste your time and the people that you can get deals done with.

Aaron Strauss: I think that's awesome, Henry. I think you just gave a two-minute primer on all sales success right there. It happens to be you're in real estate finance, but—no fear, have no reservation to go after the business and ask for the business. Eliminate all of the people who are never going to work with you.

Honestly, being proactive, not just praying and praying, as it were—just sending out some mass email—selecting, honing in on those 10–15 people you think are real, you think can get in, and just chiseling away.

That's another question. People are drawn to you. You have a ton of charisma. You obviously are backed by a world-class team, world-class track record. How do you go about it at this point? Because your day is busy, right? Thankfully, you chose to give me 30 minutes. I'm sure you've got conference calls and dinners and events and personal and family.

I struggle with this too, and I think a lot of guys in our age generation—you're in the middle of so much. How do you determine, when you wake up, what's coming on your calendar, what you're making time for, and frankly, where to focus? Because you have so much. I mean, you could spend all day today prospecting, speaking, networking, focusing on execution. Where do you find the balance? How does a normal month break down for you, time allotment-wise?

Henry Stimler: This is incredibly key. I say this all the time. Anybody that reaches out to me—be it on LinkedIn, be it by Messenger—young kids that are wanting to get into the business, I always make time to talk to everybody. My father always says, "Someone took the time to teach you; take the time to teach others."

So I'm always going to make time. If someone has the courage to reach out to me on LinkedIn—I had two calls yesterday with a kid at Miami U looking for a summer internship and another kid looking to understand the business—I'll always make time for those people.

Today, I've got a lunch at the Regency, and then I've got time in between. I've got a four o'clock meeting with a sponsor and an equity group. Then I have 5:00 PM drinks at the Aman. Then at six, I'm going to work out. Then I have a dinner at Carbone at 8:00 PM.

But in between that, I'm going to mine the pipeline. This is Newmark's pipeline. It has every investment sale that Newmark is selling. It's year-end. A lot of the funds have to deploy money by year-end. I'm going to go through this whole pipeline with my team and find deals that fell out or find deals where the seller has to sell and try and matchmake between the funds that have to deploy money by year-end and sales that have fallen out so I can bring the deal together.

It's all about connecting the dots. So we're in the fourth quarter. You've got guys who have closed-end-year funds. They have 20, 30, 40, 50, 100 million dollars of equity left over that they have to deploy by year-end. Then you've got sellers that had deals that were meant to trade that fell out.

We're going to mine the whole Newmark pipeline. We're going to talk to every broker within the platform, find out which deals could be a good fit for the funds that need to put out money. We're going to matchmake. We can connect the dots. That's what I'm going to focus on today.

That's my group today. Yesterday, and at the same time, we're trying to close deals. Yesterday, we signed up two deals, just under $200 million. Yesterday, I had a lunch, one call, then lunch, three, four, five, six, seven calls yesterday.

But someone that's too busy is never making money, right? You know that adage—if you're so busy, you can't make money. So you've got to find the time. You've got to focus on what makes sense.

Also, I'm surrounded by an unbelievable team. I tell my boys all the time, if we don't have a billion dollars in the pipeline at all times of signed-up deals, you've got to sleep in the office—as a joke. But that's what I'm always wanting to have. I always want to have at all times a billion dollars of deals signed up, going from signed up to closing.

So I'm constantly pushing, pushing, pushing, because this is a business where you've got to do a lot of deals. I'm working on a lot of deals.

Just to give you an understanding, this is a week, I leave on the 10th, I leave to Green Bay. I'm going with two clients to the Green Bay Monday Night Game with the Eagles. Then I'm going to Chicago for a closing dinner. Then I'm going to D.C. the 12th and 13th for a conference. Then I'm going back to Miami for Shabbos to be with my family.

Then I leave to the eCore Conference, where I'm interviewing Grant Cardone at eCore, which I think will be a spectacular event. That's a guy that was selling tires when he was 26 and built a $5 billion empire.

So I'm on the run. I'm on the go. I'm juggling a lot. But I've also got that unbelievable team behind me—young, aggressive guys that I've handpicked. I meet a lot of people. I see something within these young guys that—they're bright young things. They resonate with me. I bring them into the team, and together we act as a real unit.

Aaron Strauss: Well, let's dig into that for one minute. Again, hearing your schedule, I want to cut this podcast short. I want to get you out there making the deals, closing. But all kidding aside, we appreciate you, and the listeners do. Talk to them about the team—how you built it, its current construction. Will it be expanded? Is this the right size for you? How did you find your original team members?

What are some of those operating principles in the team? Because you have Henry operating principles, which is who you are. You're the dealmaker. You're the deal hunter. But then how you manage your team—obviously, they connect with you in real time—but how do you find these individuals that match your culture, your speed, your energy? How do you keep the motivation and the hunger? And how is it currently constructed?

Henry Stimler: I love talking about a team because I think I spend more time with my team than I spend with anybody else on the planet besides my family. In a way, they are my family, right? They're my surrogate family. My speed dial—the first person is obviously my wife, then the second person is Bill Weber, my partner.

So going back to the Cantor days, Anthony gave me a desk fully adjacent to this guy called Bill Weber. Bill is the complete opposite of me. Bill is Wharton-educated. I went to Yeshiva. Bill went to Wharton. Bill had spent his whole life either at Credit Suisse or then Cantor. So he's a little bit older than me. He doesn't look very much like me. He doesn't dress very much like me. He's the complete antithesis of who I am. But that yin and yang is perfect.

Anthony, to his credit, saw something in both of us—that we worked together—and he put us together. He's the head of capital market strategies. Obviously, he's not in the day-to-day. He's doing his own things. But he put me and Bill together. So my job is to originate. My job is to bring in the deals. My job is to be out there meeting the clients, hunting the clients, finding opportunities for us to do.

Once I've done that, once I've met the guy, we'll set up an introductory call, and then me and Bill will do the pitch. We're so completely opposite that it works. I'm aggressive. I'm loud. I'm flashy. I'm the sizzle. He's the steak, right? Because he has the expertise. He's been in the business for 30 years. He's done billions of dollars. Credit Suisse sent him to London in the GFC 2008 to go and work out all those deals. He's an unbelievable, brilliant strategist. He's just so smart.

I've seen him tell Blackstone how to structure term sheets. When there's an issue, he's the one figuring it out. The day I'm looking at spreadsheets is not a good day for me. I don't want to be looking and underwriting numbers. That's not what my core competency is. That's not my focus. My focus is to drive the business, hold the hands of all parties, cajole, beg, plead, be aggressive, get the deals over the line.

If the bank isn't behaving well—the lender—I've got to get on the phone and straighten them out. If the client isn't behaving well and there are issues, I've got to get them out. Many times you've got a lot of emotion involved in business, right? The client has done millions of dollars of deals. The bank wants to understand something about him, like a lawsuit from 10 years ago. It gets all hot and bothered. I come. I calm everyone down. I get everyone in a good place. I make everyone happy. We get the deal done.

Bill's job is to take what I bring and hold it all together in the structuring, in putting it all the way through—be it if we're the direct lender, be it if we were the broker. He's the problem solver. Then we have Ari Schwartzbard, who's our workhorse. Ari's the worker. He just gets it done. He's an incredibly hard worker, very smart, was a credit guy, knows and understands the business, really tough deals.

We just closed an office deal in Kansas City, a mixed-use office deal—really hard to get done. These deals are really difficult. Ari drives that bus. He gets it done. So those are the three senior guys. Then underneath us, we have a bunch of junior guys that all have what I want—to be one day originators. I want to mold them, and their job for now is to be on our business. But ultimately, the goal is for them to originate their own business.

One of the young kids that I have that I love and adore like a little brother and maybe a son to me is Ricky Warner. Ricky came to me at 23 years old from CBRE, harassed the hell out of me to get a meeting with me. I wasn't interested in hiring anybody. Then he sends me an email, says, "I'm downstairs in your building. Can I come up?" Came up to see me. I love this kid. Everything about him—I just loved him.

He already had an offer from two other firms, and he'd actually told one firm he was going to sign with them. After I met him, by the time he was downstairs in the elevator, when he got out in the lobby, I called him up. I said, "I'm getting you an offer. You're coming to work for me." Obviously, the offer took some time. We're a big institution. There are lots of steps. About three, four weeks later, I got him the offer and he signed with me.

That night, I went to a party, a real estate event, and I ran into the guy that he told he was coming to him. The guy says, "You got my Ricky." I said, "No, no, my Ricky." Fast forward, Ricky this year closed close to a $230 million deal. So from 23 years old to now, this guy is now originating monster deals. So I look for guys that can do that.

Then we have a guy that's the mirror image of Bill. His name is Nick Mazorkis. Preston Podell—we have these unbelievable, young, hardworking guys that all fit different roles that they have to be. But ultimately, I want Ricky to be an originator. I want Preston to be an originator. Preston is already getting there. Preston is running his own deals. He came to me as an intern. He was an intern for me for the last two years when he started. Now he's running his own deals.

So you need a combination of all these things. You need a combination of chutzpah. You need a combination of bravado. You need to understand how hard you have to work, how responsive you have to be, how on top of your game. There are no days off in this business. You have to just be in this business because there's nothing proprietary about what we do, right? A million other guys do the same exact thing.

There has to be something special inside of you that clients come back to do deals with you over and over again. That's part of who you are, how you treat them, how you interact with them, but also how you respond, how you take care when things are bad. You can't hide. If things are going bad, you can't be in a corner in the fetal position. You've got to have the bravery to say, "Listen, we have a problem. This is how we can fix it or we can't fix it."

So you need all these elements, and that's hard to find in people. I've met a lot of guys that want to come work for me and unfortunately can't because they don't have all these different factors.

Aaron Strauss: Well said, Henry. I mean, building that team to offset your weaknesses and enhance your strengths like you've done, and to do it at a multi-level dynamic internally where everyone is hunting and gathering together—that's brilliant. Then also to have the massive platform that Newmark offers as well on a national scale, and the energy you bring, the passion you bring—it's infectious. It really spreads, and you can see it.

I guess the last question—because we could talk all day and I want you to get to your lunch and your craziness today—mental health. It's a very emotional roller coaster being in the sales, execution, team management, topsy-turvy world of real estate with all of its players—or any business, for that matter. You ride highs, you have lows, you obviously have a personal life, you've got to be with the family. How do you keep that motor of optimism going?

I know we talked a little bit about it, we covered a bit, but that mental health issue—how do you stay mentally sharp? Forget physical, because I know you're exercising, but that mental headspace is so critical. All of it happens between your ears. So this is The Dealmakers' Edge. We try to talk about people's, you know, not only the positives, but they have to manage those voices. So how do you keep that sense of optimism and enthusiasm going all the time?

Henry Stimler: I would say the most pivotal moment in my life was that after the crash of 2008. So let me paint the picture for you so you understand. I'm 28 years old. I've come to New York with $400 in my pocket at 22 years old. Got, I don't know, lucky, found this business, built this business, and I'm making money hand over fist.

I have an Aston Martin. I have a Rolls-Royce. I'm living on 65th between 5th and Madison in a beautiful apartment. I have an office with 14 people at the Crown Building—magnificent office. I have offices in London, an office in Israel, an office in Belgium, and money is flowing—and stupid money.

I have the ability to go out any night of the week and buy and spend five, six thousand dollars without blinking. I have watches galore. I'm buying art. I'm traveling on private planes. I'm rubbing circles with celebrities. I'm just living this amazing life at 28, which looks like out of a movie for a kid from Golders Green. It just doesn't compute. I thought this would never end.

Then in the space of two weeks in September, the whole world comes crashing down on you. A black swan event, no liquidity, no money, and everything you've built over the last six years disappears in the space of maybe three weeks.

That's just a huge fall from grace. I was arrogant. I think in those days, I was untouchable. My father would tell me all the time—he called me, my Hebrew name is Ushi—he'd say, "Ushi, it doesn't last forever. Put money away." I never listened to him. I just lived from one day to the next.

That could have broken me. That could have literally broken me to a place that I could never have recovered. But I didn't let it break me. I let it teach me lessons. It taught me so many important lessons. One, never be arrogant, right? Full, big fall from grace. Never be arrogant. Never be cocky. Be confident, yeah, but don't be arrogant. It taught me that you've got to just move on. You've got to dust it off and keep on going.

So when you have that thing happen in your life, when you have something of that magnitude hit you, give you such a punch that you never saw coming—we never saw it coming. I'd just gone to the VMA Awards, taken a private plane with my friends, flown to LA for the VMAs because my buddy Russell Brand was hosting the VMAs. He said, "Come with me to the VMAs." I went to the VMAs, came back on a private plane, back to New York. Then within three, four days, it just dissipates. Your whole world crumbles.

So if that wasn't going to kill me, if that wasn't going to knock me down, nothing is. But it taught me so many important lessons. So when deals break and deals die, nothing a deal can do can ever eclipse what 2008 was to me. So mentally, I'm incredibly strong. I'm very, very strong—mental fortitude—because of that. That happened, and that formed me. That made me in that fire. That totally changed me.

I knew I had to just dust myself off and go again and rebuild and start no matter what it was. It took me two years to wind up the business. It was humbling, humbling, humbling, humbling to a huge point. I would literally go to the cash machine and I would put in my number three or four times. It would say the same message: "You are overdrawn. There is no cash. There is no freaking money." Like, no money. No money. I was done.

So then I would promote and get $400. I would find it—$500. And so going through that baptism of fire, that was the best thing that could happen to me, right? That was the best thing that God could put in my path because it taught me so much. So today, things don't work out, we move on. We get up. We move on. We don't hide. If there've been some good years, there've been some tough years. I would say 2020, 21, 22 were amazing. 23, 24, a little bit tougher. Market's going much better, 25, thank God, has been fantastic.

But what doesn't kill you only makes you stronger. That's the attitude I have. In hindsight, I'm incredibly grateful for that fall from 2008 because it's given me the mental fortitude to move forward and to take the hits and say, "Okay, it's not the end of the world." Life moves on. That's what 2008 taught me. I think that's the best thing that could ever happen to me because it also took away my arrogance, my bravado, and replaced it with something much more enlightened.

There are going to be ups and downs in life. The most important thing is you dust yourself off and you keep going.

Aaron Strauss: Amazing, Henry. I really, really personally took a lot. I know our listeners will as well. I will let you get on with your absolutely insane schedule and day, and I'll continue to follow your illustrious career, as will all of our listeners. Great hanging with you. Appreciate you and much continued success.

Henry Stimler: Thank you so much.

Aaron Strauss: Thank you for joining The Dealmakers' Edge. Don't forget to follow us on your favorite podcast platform. Please give us a five-star rating so more people can follow the conversation.

The Dealmakers' Edge with A.Y. Strauss highlights the stories, successes, and struggles behind major commercial real estate investors. Each episode offers a behind-the-scenes look at commercial real estate leaders and their unique edge.

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