Transcript

He LOST A BET and Ended Up Owning an NBA Team | David Adelman’s Billionaire playbook

From Ryan Hawk · Episode page · Watch on YouTube

· 51 min · 10,808 words · 140 timestamped sections

This is the full, timestamped transcript of "He LOST A BET and Ended Up Owning an NBA Team | David Adelman’s Billionaire playbook", an episode of Ryan Hawk published November 29, 2025 (51 min, about 10,808 words). It mentions 29 people, works and ideas, including DeSean Jackson, Philadelphia 76ers, Student housing, Selling, Campus Apartments.

What this episode is about

David Adelman's journey to becoming an NBA team owner began with a childhood bet that set the tone for his unconventional approach to life and business. Emphasizing the importance of embracing challenges and learning from failures, Adelman shares his mantra of living without the constraints of traditional paths, advocating for active listening and the willingness to experiment with new ideas in both entrepreneurship and leadership.

Key takeaways

  • Turning work into play: it's all about calling it 'the office,' not 'work.'
  • 13-year-old real estate mogul: investing bar mitzvah money beats blowing it on candy.
  • Losing a basketball game taught me debt repayment via sweeping sawdust; childhood lessons stick!
  • Conventional paths are snooze-fests; embrace the suck and pivot when necessary.
  • High risk, high reward: failing isn't failing if you're learning.

Who speaks in this episode?

What is discussed, and when

  1. – 5:00: Allan Horwitz, Campus Apartments, Embrace the suck, Learning Leader Show
  2. – 10:00: Carpenters Union, Holocaust education, Philadelphia Holocaust Memorial
  3. – 15:00: Student housing, Why not me and why not now?
  4. – 20:00: Embrace the suck
  5. – 25:00: Apollo, David Blitzer, Josh Harris
  6. – 35:00: Student housing, Campus Apartments, Selling
  7. – 40:00: Campus Apartments, common courtesy, Holocaust memorial in Philadelphia, Selling
  8. – 45:00: Cred.ai, ING Direct
  9. – 50:00: Apollo, Blackstone, Comcast, Darkco Capital
  10. – 50:42: David Adelman

Notable quotes from "He LOST A BET and Ended Up Owning an NBA Team | David Adelman’s Billionaire playbook"

  • What do you think about the profession of selling?
    about Selling · at
  • Whatever. And so like I had to go down to his office. So he's the founder of campus apartments. I'm actually sitting in this building you know 40 years later. And he says you…
    about Campus Apartments · at
  • Now is surrounding University of Pennsylvania's campus. Allan was one of the early pioneers in student housing, okay? Where like he really thought that was like a dedicated…
    about Student housing · at
  • He really, gave me a lot of the values I have today and I built the Philadelphia Holocaust Memorial and we named it after him and my uncle actually and but just a really great guy who in Poland had a wife and two kids gets rounded up by the.
    about Philadelphia Holocaust Memorial · at
  • Came to the States. My grandfather became a carpenter here, was a proud member of the carpenters union here. So, it's funny cuz I'm building this new arena in Philadelphia that we may talk about and the Carpenters Union when I told them the.
    about Carpenters Union · at
  • And so I think what it does is one from the philanthropy perspective, particularly in Holocaust education and things like that, like I want people to know my grandfather's story. I don't do well with, the Holocaust deniers.
    about Holocaust education · at
  • Partners in the Sixers, Josh Harris and David Blitzer. Okay? Josh was the founder of Apollo, an amazing private equity shop. he retires from there and then, even though he's…
    about Apollo · at
  • And I feel like we've lost a lot of that in a society. And so like common courtesy matters to me. it matters to the businesses I'm invested in where it's hey, let's treat people well and let's like appreciate the fact that.
    about common courtesy · at

Who and what is mentioned in this episode?

People

  • DeSean Jackson — Person · 6 mentions
  • Steve Ballmer — Person · 2 mentions
  • Allan Horwitz — Person · 1 mention · first at
    Can we start when you're 11 years old? This is a crazy story. There's this family friend, Allan Horwitz, I believe.
  • Josh Harris — Person · 1 mention · first at
    They do other great things, case in point, I have two great partners in the Sixers, Josh Harris and David Blitzer. Okay? Josh was the founder of Apollo, an amazing private equity shop. he retires from there and then, even though.
  • David Blitzer — Person · 1 mention · first at
    Know, case in point, I have two great partners in the Sixers, Josh Harris and David Blitzer. Okay? Josh was the founder of Apollo, an amazing private equity shop. he retires…
  • David Adelman — Person · 1 mention · first at
    Started investing and it turned out to be okay. and so literally Darkco D- A RC David Adelman Realy Company. Okay.

Companies & orgs

  • Philadelphia 76ers — Company · 5 mentions
  • Campus Apartments — Company · 3 mentions · first at
  • Apollo — Company · 2 mentions · first at
  • Los Angeles Clippers — Company · 2 mentions
  • Learning Leader Show — Company · 1 mention · first at
    David, man, it's awesome to have you here on the Learning Leader Show.
  • Philadelphia Holocaust Memorial — Company · 1 mention · first at
  • Carpenters Union — Company · 1 mention · first at
  • ING Direct — Company · 1 mention · first at
    Close friend of mine was one of the pioneers of the old internet bank ING direct. So it was kind of like a you know the first internet bank about 15 years ago. I don't know if…
  • Cred.ai — Company · 1 mention · first at
    Tech side and really savvy. And we created this great fintech called Cred.ai.
  • Comcast — Company · 1 mention · first at
    It approved. But then, for the good of the city, we came back together with Comcast, who owns the Flyers. and we're doing a great building together. and, I'm excited about it…
  • Darkco Capital — Company · 1 mention · first at
    Yeah, my family office, Darkco Capital, we've got a pretty good website. It shows what we're doing, the companies we're invested in, talks about Philly and how important that is.
  • Blackstone — Company · 1 mention · first at
    Was everyone has these cool names and Blackstone and Apollo and, like all these companies had great names and I'm like what am I going to call my thing, right? And like my I didn't know that my thing would be.
  • chat GPT — Company · 1 mention

Concepts & topics

Places & events

  • Holocaust memorial in Philadelphia — Place · 1 mention · first at
    Was he willing to understand that, but he went one step further and said, Can you take me to your Holocaust memorial in Philadelphia and actually educate me?

Full transcript with timestamps

Whatever you do in life, it it shouldn't feel like work. I have never said, "I'm going to work." I say, "I'm going to the office." And I think that's a real difference.

You became the CEO at 25. How did this happen? I live my life by this mantra like, "Why not me and why not now?"

Isn't the conventional path pretty boring? To me, it is. When I'm mentoring kids, I'm like, "Embrace the suck." Okay? Like, not everything's going to be fun and pulling the plug is okay if it's not working.

Are there times when you had to pull the plug? I also believe if you don't fail like you're not trying hard enough. The the entrepreneurs that I see very successful are the ones that are open to learning. I don't think I'm the smartest guy in the room. People don't know how to listen anymore.

Yeah. People wait to talk and they don't listen. I am never too embarrassed to say like I don't know something.

What do you think about the profession of selling? Try to get noticed for the right reasons. Don't people. That's my number one rule. And then like don't be afraid to put out a bad idea. I don't think you're a successful leader CEO if you're not willing to listen.

David, man, it's awesome to have you here on the Learning Leader Show. Welcome.

I'm so psyched to be here. Thanks for having me, Ryan. Can we Can we start when you're 11 years old? This is a crazy story. There's this family friend, Allan Horwitz, I believe. He challenges you to a basketball game. Can you tell me about this? Like, what happened when you were 11?

Yeah. So, you know, I'm sure you have everyone has that kind of friend or family friend that they call uncle who's not really their uncle, but like becomes like more than family. Um, so I have this crazy uncle Allan growing up and he's the family friend who was just like the cool guy like always driving like cool cars when you're a kid. Like I remember he had like a Corvette and I thought that was like the coolest thing in the world. And I'm 11 years old and we're playing basketball and I guess like as a kid you're kind of like I'll beat you. I I'll bet you I can beat you.

And like, you know, guys like you or I would probably let the 11-year-old kid win.

I don't know. Would you? Would you? Maybe. I don't know. He's a really competitive guy. And um I I mean he's 83 today and he will like [ __ ] kill you. Sorry. Kill you for a quarter on the golf course, right? Like if you're trying to putt or whatever. Like he loves it. Um so he's just a high energy guy and he just said, "I'm going to teach you about betting." And like he's like, "Well, what do you want to bet?" You know, I didn't have money. I'm 11. And he's like, "How about that baseball glove?" And I'm like, "Okay." And I lose. And I'm like, "Again?" You know, I remember. He's like, "How about your football?" Right? So I literally, this happens for like 30 minutes. I lose my baseball glove, my football, my basketball, and then I don't know if you remember when you're a kid, but like you'd have like a bank book that was like your money in it, right? Okay. And I lose my bank book to him, too. Okay.

And my parents are dying laughing like what you know I don't know that like whatever. And so like I had to go down to his office. So he's the founder of campus apartments. I'm actually sitting in this building you know uh 40 years later. And uh he says uh you got to come down here and stack lumber every Saturday and sweep sawdust and I'll give you one item back. You have to work it off. He's like it's called working off your debt.

And I was like okay. You know I didn't know. And my parents were like this is great. You go do it. And you know, each week I went down there, I got dirty, I pushed a broom with some sawdust, I had to uh, you know, move some stuff around and I got one thing back.

And and so the the story continues that two years later, I'm 13 years old, I have my bar mitzvah and I have some gift money and my parents are like, "Hey, do you want to give it to your grandfather? He was really good at picking stocks and things like that." And I'm like, "No, I want to give it to Uncle Allen and buy real estate." at 13.

They're like, "You want to do what?" Like they thought it was like the craziest thing in the world. Um and so literally I um get in the car with him and he goes, "Well, what building?" And I said, "Well, what do you own?" And you know, where I am in Philadelphia right now is surrounding uh University of Pennsylvania's campus. Allan was one of the early pioneers in student housing, okay? Where like he really thought that was like a dedicated asset class versus a hobby for somebody renting out a duplex to a college kid, right? And so I drove around and I'm finally like, "That one." And we get out and we look around and he's like, "Well, why this one?" And I said, "Because it's the biggest one you have." You know what? I don't know [ __ ] about real estate at the time, but I'm like, "Okay." And so literally like, you know, I hand him my $2,000 and I'm a partner in real estate. And like literally he taught me the business from

a kid on. Wow. Well, I feel like when you're 13 and you get 2,000 bucks, you're like, I want to go buy some video games, candy,

uh, Jordans, right? Like, yeah. Music. H how did you have this kind of foresight, this like adult

viewpoint of no, let me let me find a way to invest so that this thing can grow? Like, where did you learn that?

Well, it's funny because he would also like have these lessons about the value of a dollar.

Yeah. And so like it just started resonating with me and like I I'm like so it just felt like investing was the right thing. My parents were like you got to invest it and you can't blow it on you know on candy and you know and sneakers. So like I knew I was going to have to do something with it. And uh you know he was one of those entrepreneurs who you know never went to college you know was doing this from the time he was a kid. A really interesting story. His father died when he was 10 years old leaving him and his mother some real estate in a rough part of Philadelphia.

Um, and then he was with his mom at the University of Pennsylvania, saw kids waiting outside a broker's office, like a realtor's office, and he's like, "Mom, kids are waiting in line for apartments. It's a captive audience here." So, he had this epiphany as like a 16-year-old kid. It was crazy.

Wow. Wow. Okay. I love it. And I I think going back to your family history, there's even more uh incredible stories, especially from your grandfather and the Holocaust. Can you can you tell me the story about your grandfather? Yeah, thanks for asking. It's uh, you know, just a he was a wonderful guy and so uh he really, you know, gave me a lot of the values I have today and I built the uh Philadelphia Holocaust Memorial and we named it after him and my uncle actually and um but uh just a really great guy who in Poland had a wife and two kids uh gets rounded up by the Nazis, taken to a prisoner camp and there's two lines, one for men and then one for women and children and never saw his wife and kids again. um

you know they were obviously killed and uh you know he was in a prison camp and uh the interesting thing about him is that he wound up escaping from his prison camp um and there was a movie about this called escaped from so bore he's he escaped from the soie bor prison camp uh then became a uh freedom fighter um against the Nazis got shot and was in a hospital recovering um and there was a woman there with her brother checking on her brother who was injured sees a lonely soldier like in the corner of the hospital unattended and goes over to just like you know be like you know the human thing like you okay whatever that's my grandmother

and so literally meets my grandmother in the hospital and my mother what was born after the war in what was most people don't know this but after they liberated you know America the US soldiers came and liberated the camps um they didn't know what to do with all these people right they were pulled from around Europe to these you know concentration camps. So they set up what was called displaced person's camps, like literally like these refugee camps where people live. It was not like that sad, but it like there until people got their lives together. Uh so my mom was born um in a displaced person's camp and what you know, her her passport still says, you know, like you know, West Germany, right? There's no West Germany anymore, right? Um and uh you know, then they moved to Israel for 10 years and then came to the States. My grandfather became a carpenter here, was a proud member of the carpenters union here. So,

you know, it's funny cuz I'm building this new arena in Philadelphia that we may talk about and you know, the Carpenters Union when I told them the story about him, they found his union membership card from the the 60s. So, it was pretty wild.

Wow, man. Like when you think about the stories of your grandfather, your grandmother, the your parents,

like how does that impact you and how hard you work and how ambitious you are and how phil philanthropic you are, how you want to help others and serve. Like I can't even imagine with like that's not my family background. My family background is cool and I'm super grateful, but it's it's certainly not that. like how does that impact you as a leader, as a husband, as a dad, as as a community leader? I'm just curious the the impact that has on you.

Yeah, look, lot lot to unpack there, but what what I would say is it does a few things. One, like

no matter what, when I'm getting the crap kicked out of me in business or anything else, like I don't know struggle,

okay? And so it, you know, what it really taught me was, and I've been through some really like tough business situations and tough situations. And I'm like, you know, that's not pressure.

And so I would think about my grandfather, what he went through, and I'm like, you know, that guy knew pressure, right? And, you know, made it through the other side. So like, you know, I'd kind of say like I have to stop being a little [ __ ] about it and like kind of like lean in and let's go. Um, and so I think what it does is one from the philanthropy perspective, you know, particularly in Holocaust education and things like that, like I want people to know my grandfather's story. You know, I I I don't do well with, you know, the Holocaust deniers.

That doesn't sit well with me. And so I feel a duty from a educational perspective and a philanthropic perspective to fund those type of initiatives. Um, I think it's important for my kids and, you know, their kids to know about their grandfather and the others like him and what they went through. Um, this may be a weird question, but as you were growing up, how important was it to you to become a a wealthy person, meaning a guy who makes a ton of money?

It's a great question. Um, I definitely, you know, so, you know, I have this mentor and uncle Allan. Uh, my father was a psychologist, but like a successful one, like opened up mental health clinics, like he, so I I had people in my life that I watched. I had friends and their parents watch that I thought that I respected in business.

Um, and for me, you start off if you're in business to say like, well, it's about the money, right? I want to rate I want to make money.

You know, after you've done okay, it it has to be about something else. Like, why are you still going? And by the way, I have friends who have sold their business businesses in their 40s or 50s and they're like, I'm good. I'm out. H

I would be like I really though I do you have me because like I've seen the ones who do that who like guys who made a ton of money like you billionaires whatever they don't you can't almost become that if you're able to turn it off and I and I mean there's there's good and bad parts about that like so like for me I've seen those types and they're not really able to just chill. They can for like a couple days and then it's like wait what am I doing next? What impact am I going to have on the world? like how am I going to help people? Like it just seems as though the people who are able to accomplish those big things, maybe have a big exit, whatever it is, they're not able to chill. They're just not they're just not it's not not a part of their being.

Yeah. Look, so I I agree with that. I think what I have seen in my experience is the the guys or gals who call it quits said, "You know what? I'm okay. I'm comfortable." Right. And they've defined what their comfortable is. and you know and you know maybe it's two vacations or three but like they've got their budget and they're good or maybe they did well and they have the beach house and they're like I hit my bid and I'm good. Um I agree with you like you know the guys I roll with and the women in business like you know for us it's like like it's not about money right like you either are wired to get up and work hard every day and do it. Um and it has to be about something else. It could be about the people who work with you or for you and providing great opportunities for them and their families. It could be because you're solving complex problems or like you're creating a business that you're just so

excited about. Okay? And so for me, that's really um the energy that I try to convey is that like do something really amazing um and enjoy it. And so, but you know, back to Uncle Allen, he always said to me, you know, whatever you do in life, it won't feel like it shouldn't feel like work. So you so you know I have never never said I'm going to work.

I say I'm going to the office. And I think that's a real difference um in how I think about things, right? This isn't work. Now, do I am I tired sometimes and I'm run down and like there's some days where I wish the phone would stop ringing. 100%. Um did I miss a lot of stuff with my kids if you were talking to them? Absolutely. Right. And I have deep regret over that. So like you know there's good and bad. You know, with success and money comes a price, too.

I feel like if to me it feels like work, but it doesn't feel like a job because you still work really really hard, but it's not like a job. It just what you do. So, the the other part of your story though that I wanted to get to, you talk about Uncle Uncle Allen again. This is what this is crazy to me. He I read this, tell me if this is true. He said, "I realized that I I realized that David would someday run the company because of his ambition." And then you became the CEO at 25. Like tell how did this happen? So, so what happened was Allan had built this really successful business in Philadelphia and he enjoyed his life. Like he enjoyed not, you know, for him who was a self-made guy and came from not a lot of money. I think for him it was like I'm not going to be greedy.

I'm gonna build something great and I'm gonna enjoy myself. Um and so like he found that balance that I wish I had and some of my friends had. Um and so I had this goal like as I start to start started to really understand the student housing business. What was happening in this is in the 1990s. No one was really doing it at a large scale nationally at the time. Okay. It was a nent business and I saw this like white space of like why aren't people doing this everywhere? And so like I have I run I live my life by this mantra like why not me and why not now?

M so like you know like I you see all these ideas and I'm like well [ __ ] it right I'm your listeners are going to have to get used to me cursing but I'm kind of like you know why let's do it like why not like because I'm not afraid I'm not afraid to fail and I think if you're not afraid to fail it's very it's a freedom. Do do you draw from failures and and your ability to bounce back or like what are what is there are there examples of times when you went all out you you committed everything you had and you lost and you were able to to bounce back. I'm I'm curious where that comes from. It's because I think it's easier said than actually done. Like it's sexy for us to say like yeah man let's go and if we fail well we fail. Who cares? But in reality like that's really really hard to do. So, where how how have you gotten good at that?

Well, and look, you know, do I you know, there it's a lot different when you're 33 versus 53 about how much you're willing to risk, right? So, I might fail today, but I you know, I'm not going chips all in either, right? So, I have failures along the way. Um, but I also believe if you don't fail, like you're not trying hard enough. Like, and so I'm okay with that. So to answer your question, I think it really comes from the goal of like pushing yourself and like I have this other saying that when I'm mentoring kids, I'm like embrace the suck. Okay? Like not everything's going to be fun and some things are hard. Um but sometimes when you push through them, you get to another side of things.

Um sometimes you don't and pulling the plug is okay if it's not working. Are there times when you had to pull the plug? uh when when it sucked really bad and you just embraced it like what's a time that that happened? I I I've had that happen in a lot of businesses where I'm back, you know, one part of my and I don't know if we're talking about but you know I spent a good part of my day you know kind of backing founders and other businesses in things where I become a partner and you know help somebody build their business and you know that business I've gotten good at understanding like hey that business might be a great opportunity a great idea and the wrong time

and so like sometimes you have to make that decision of like hey you know what this isn't the right thing it's time to call it take our losses and you know look I think failure today is more financial than, you know, emotional or psychological or what it could be earlier in your career.

Uh, I I like to think about trade-offs as we're building something special. Um, and you you you kind of briefly brought up the thought of uh, you know, you're a dad, you're a husband, and so sometimes there are trade-offs, you miss things as you're trying to build something. How do you I don't like the word balance, but h how do you manage the tradeoffs that sometimes it takes of hey, I'm going to miss out on this business opportunity to be with my family and or hey, I'm going to miss out on time with my family to to be to because I need to go meet with LeBron James or something to invest with in his tequila company, whatever. Uh like h how do you how do you think about tradeoffs as you're building something special and trying to impact the world in a positive way?

Yeah. Yeah. And so, so what you're saying is very key is like as you're building something and so I think earlier in your career, whoever it is, if you aren't willing to make sacrifices and build that foundation for the future,

that's okay. Like being an entrepreneur might not be for you. Um, and so like for me, I made choices along the way to miss certain things, my wife and kids. Um, now I look back and I say, were all those things that I missed worth it? Probably not. Hm.

Okay. Um, you know, you reflect, my daughters are 21 and 23 now. Okay. Um, and you know, I missed a lot of their early growing up and things that I wish I didn't. And the only thing you can do about that is make up for it later on.

Mhm. And so, like my my older one, my 23-year-old, you know, about four years ago, you know, because I try to apologize to them whenever it comes up because I like I'm like, "Hey, I'm sorry if I missed that or whatever." And, you know, my older one's like, "You know what? We remember this dad more than that dad." And so like the point to that is it's never too late to make a change.

And um but to to your early point like how do you know um I think when you're building a business or building kind of like what you want your career to be. And you know for me my career isn't one thing. It's kind of multi-dimensional. Um and it's driven by curiosity.

And so like sometimes I'm like hey I just got to go to this conference and I got to go hear about this. And like you know now you know I'm able to like so the the benefit now is I'm empty I'm an empty neester so I'll bring my wife with me where before I left my wife and kids at home

right so at least like I'll you be able to like go to do something her day and hang out my with my wife for dinner or later whatever um you know trying to get my my youngest daughter uh is a senior in college and I'm like hey is we she's a little more predisposed to business my older one is a teacher um and I'm like hey do you want to come to this business thing with me right so can I do it where I incorporate them into the mix here.

I love that. When you like you spend the bulk of your time around leaders who have sustained excellence over an extended period of time, whether they're professional athletes, they own sports team like you do. Uh again, do crazy incredible philanthropic work. When you think about all of those people, David, this this may take a second to think about, but when you think about them, what have you found to be some of the commonalities among those who have sustained excellence over an extended period of time? I think the drive and the goal to succeed. And so in sports, let's just take sports, and I'm not going to name names, but when you see the athletes that show up for practice early, stay afterwards, and this is about them making themselves better, doing certain things, putting the time in. Okay? When I see business people who have already had achieved enormous success, um, and they do other great things, like, you

know, case in point, I have two great partners in the Sixers, Josh Harris and David Blitzer. Okay? Josh was the founder of Apollo, an amazing private equity shop. You know, he retires from there and then, you know, even though he's running sports teams, he goes and starts another unbelievable private equity firm, right? And he's crushing it. You know, David Blitzer, my partner, you know, is a really savvy investor. He's the first guy in the country to have owned an interest in all five pro sports leagues. Um, and so I think when, you know, it makes me feel better to know that I'm not the only one who's wired. wiring is broken, right? Because where you see when you surround yourself with a bunch of people or

is it broken though? Why? Why? You know, it's different, right? It's not conventional. Okay. Um I I think it's not, you know, when what we're conditioned to learn is, you know, go to work, come home, do these things. I think it's changing now in the startup and founder environment where I think you're seeing people probably conditioned too much to the other side. Uh and we could talk about this. I think too many people think they're slated to be an entrepreneur or founder. Mhm.

And what I advise people is you can be a great entrepreneur, but sometimes you might be better suited to be an entrepreneur in somebody else's business.

Isn't the conventional path pretty boring? To me it is. Right. To me it is. Like I couldn't do it. Like

have you always been that way since 11 since before that? Like I've always been that way that you know I as a underachiever in college low SAT low GPA like you know for me like I just wanted to get in the working world. Like that was for me. That's what I wanted.

Huh. So, do you think this is a wiring from birth or is it Uncle Allen's influence and others? It's kind of a nature versus nurture question, but I'm just curious because I like to think and have a growth mindset that this is available, but there are some things that you're probably just kind of born with. But I I'd be curious to get your thoughts. Yeah, I I I think you have to be born with some of it, but I think you also have to be willing like I think that the the entrepreneurs that I see very successful are the ones that are open to learning.

All right. So, like I don't think I'm the smartest guy in the room. And you know, I continue to want to learn about other people's businesses. You know, it could be the widget business that I know nothing about. And you'll see me like if I meet somebody somewhere, I'm like, "Well, tell me about that business." I just want to learn about it. And so like I think if you have that inquisitive mind and a goal to like so for me my I look at it I'm like how do I solve that problem whatever that problem is. So some guys tell me he's in the widget business and and I'll think of like 10 things they should try to do like it's not my business but you know why not?

Just your mind is set up to to always be asking questions to be thinking of potential solutions to problems and then having those conversations with people.

Yeah. So part of it is like, you know, I I definitely have like ADD and a touch of OCD, which is like a weird combination. So I obsess over like really minutia [ __ ] things for a short period of time.

Like like what? Like it could be anything in like so I'm a develop you know my day job is a real estate guy, right? So I'm building a new arena for the Sixers and the Flyers in Philadelphia. Okay. It's a 1.51.6 6 billion project and like the stuff that I'm texting our guys about to like think about from like you know how the lights should be you know make sure we put up a drink rail and so the latest one was literally I'm like hey we need to make sure that when someone goes when a guy goes to the bathroom and he's standing at a urinal we have drink rails

I love it I love that because no one does that like very few people do it and I'm like everyone walks in there with a beer or soda or bottle of water like where are you putting it when you're at a urinal right

and so like like it It's minutia that I think about. Um, but it drives me, right? It drives me to be great. It drives me to have our teams be great, you know, professionally or in the, you know, in the in the sports world.

So, I think of like another arena that's a newer one that seems to be different is, uh, Steve Balmer's uh, with the Clippers. So, would you just like call or text Balmer and say, "Hey, man, can we can we talk through like some of the cool stuff you did, maybe some of the mistakes you made?" like do do you is that like part of your process when you're building an arena?

So, you know, we just it's funny. We just toured uh Steve's arena um and you know, his president um she was terrific. She took us around. She answered all our questions like, "Hey, lessons learned, troubles along the way, what what what's not, you know, you're two years into it, what's not wearing well?" Like all that. So, what's really great about sports is as we were narrowing our selection on the architects or the contractors, I spoke to owners of like a handful of the newest football stadium teams, basketball, like just lessons learned about the process, you name it. Um, and and for me, like I am never too embarrassed to say like I don't know something.

Yeah. Yeah. One of the things I talk to kids about when I mentor is like most kids are most people I think not just kids are afraid to say I don't know or I don't understand.

I I don't know man. I think it's a superpower that it seems like you've got it w which like you yes everyone's got an ego uh to a certain extent and you've you've you've you've had sustained excellence over time. So that that would maybe lead people to think that like you know it all and obviously you don't like nobody does especially when you're doing new things that maybe you haven't done before. I think coming at it like a beginner and being curious actually leads to really deep and that's what this podcast is. It leads to really deep like really cool conversations where you're a lot better off because you were you had zero fear of looking stupid like no fear. And I get that sense from you that like why why does it matter? I'm just going to ask if I'm thinking it.

Let's ask. And I bet the people you're asking enjoy it. They probably like the fact that you're that way. I I think so. I like when people ask me questions, you know, I I I say this to groups all the time and our employees like look like if you're embarrassed for looking stupid, isn't it more won't you look worse if you don't know what you're doing down the road because you didn't ask someone how like you know so to me it just shows you're listening when you're like I don't understand that. Could you repeat that? You know,

I think curiosity man is an ultimate act of love. It especially when you're learning about other people and asking them questions. That's how you build deep, meaningful relationships with people is just being genuinely into them and genuinely curious about their stories. And in your case, you can be genuinely curious about them, their business, what they're doing, and you could learn for what you're trying to do, right? Like build an arena is a crazy project. I mean, that's insane. It doesn't happen that often. And so to do it, you might as well say, "Hey, I can be the dumbest guy in the room. I can ask those questions." I think that could there's a lot of life lessons from from that I think. Do you take that into other areas of your life just always going around asking about the most basic things in order to learn so that you can improve?

Yeah. Well, look what Ryan what you're really talking about is like people don't know how to listen anymore.

Yeah. People wait to talk right and they don't listen. And and I think that is like a really terrible thing happening right now with folks is that they're not thinking about, you know, what they can get from actually staying focused. Um, and look, everyone's 80, everyone's on their phones, whatever. You know what I So, it's funny. My youngest daughter, when I have dinner with her, I hand her my phone so that I won't be on my phone. You know what I mean?

Like, do what you got to do, man. Well, I just want to be like, I want to be there. I want to be attentive, but you want to absorb it, right? Like why are you wasting time meeting with people if you're not going to listen to them?

Yeah. What do you what have you learned from your childhood from those stories at 11 and 13 and and moving on that you've tried to instill in in your two daughters that they're not going to be exactly like you. They're probably wired a little bit differently, but they do have your DNA. So, what have you what have you taken from your upbringing and your childhood that you try to instill in them?

Yeah, I I I think the first is make lots of mistakes. Just don't make the same one twice.

Okay? Like just try hard. And two, like don't be afraid to put yourself out there.

Like the worst thing that happens is someone says no, okay? Um like I I joke with everyone like I met my wife in a bar. Okay. Literally I was in line trying to get a slice of pizza and this beautiful girl is in front of me and I was like I got to talk to her, right? Like

how did you open? I was I just said something like I was like I got you know I gotta ask who you are like I haven't seen you. like I like it if something like it wasn't like cheesy bar line but it was like I don't know if it was my smoothest moment. There's a whole backstory that two different people had told me about this girl and it turned out to be her that I had never called.

What? Yeah. It's a it's a crazy story. So literally it's actually a great story. So two different women had told me about this really nice sweet school teacher that I needed to call that she was amazing but everyone just focused about how great she was. So, like you know when your grandmother would be like, "Oh, I have a really nice girl for you." And you're like, "Eh." You know, like, you know, and that night we're at the bar. I went with my best friend. He's want he's chatting some girl up in the corner. And I was like, I'm going to leave cuz I was stay I was staying at his parents house. This is like 25 or 26. And I go in line for the pizza. I meet this girl and like I realize that she's the I'm like, "You're the school teacher?" And she's like, "Yeah." When I said my name, she's like, "Oh, I think I've heard your name. Did are you from?

I'm like, "Yeah." She's like, "I heard you were." She's like, "You were supposed to call me."

And I was like, "Oh my god, you're I was like, God, if I knew you like it was really bad." I was like, "If I knew you looked like this, I would have called. I said something stupid, right?"

Um, but the funny part is the girl that my buddy was talking to was her best friend. They all went there that night. He wound up marrying her. I married Haley. And our kids are best friends. Crazy story. We're all smart.

I love it. I love those stories. You got to have some guts though, right? You gota you got to ask. You got you gota shot and you gota You've probably been rejected before, right? You've been rejected. That's part of the deal of you. Now, don't be weird or like don't do any don't cross the line. But I I like this is one of the things I'm concerned with is the how easy it is to meet people on your phone when it's it's a lot more healthier, I think, and better for all of us if you're willing to approach somebody. I had a dating coach on recently, Blaine, and Blaine was awesome. We talked all about this about the willingness and the ability to approach someone respectfully, but then you know maybe sound kind of stupid at times, but that's okay.

Of course, that's part of it. Yeah. Like not everything should be scripted like you know I'm only imagining now that people in these dating apps are like using chat GBT to write their approach lines, right?

It's probably built in. I don't know. I mean it's insane. And so like you know the whole part of the chase and like all of that is like the excitement about it. And by the way it's not dissimilar from business right?

Yeah. But it's why. But you take that one step further. Like I hate work from home because I think people are just screwed of the opportunity to interact with people and better their career career and learn about things.

It feels to me like uh I could be making this up that you are, by the way, my first 12 years of my professional career after playing football was uh as a sales professional. And I think it's the most noble profession in the world. The the economy would come to a screeching halt if we didn't have great sales professionals. So, I say this as a giant compliment. I feel like you are probably really good in the sales process and probably have been since you were young. What do What do you think about like the profession of selling? I mean, you're a CEO at 25. CEO has got to sell all the time, whether it's internally to your team or externally. You got to raise money. You're doing all types of selling. Man, what's your overall philosophy and the way you look at sales?

Um, don't [ __ ] people. That's my number one goal. I think people will tell they know. And so, you know, even if at an early age, I I had the humility to say, I don't know everything. Here's my business plan. I'm taking this industry that's kind of new. Here's why I'm expanding it. I think it's about the people and I would, you know, help develop our staff and then move them to new locations. And so, I had a vision uh without the foundational education of it, but just like the idea of like why I thought I could scale campus apartments across the country and do it, you know, at a time when that wasn't done. You know, now there are tons of huge student housing companies across the country and across the world.

You guys were the first. We're one of the handful. There was like a handful of folks that were doing this in a way and we were certainly one of the two or three at the time.

What made you believe this could be a a nationwide thing. Uh uh so what told me it could be is I was going to real estate conferences when I was like 25 26 and you would have I joke but you'd have like the apartment guys, the office guys and the shopping center guys and they wouldn't let the student housing guy sit at their table. Like most people at that time like 20 years ago 20 were like, "Oh, student housing is crappy real estate. It's animal house and uh whatever." And I was like, "Holy [ __ ] either they're all right or I'm right."

Well, one of us is right. Okay. And I then I was kind of like I know the returns we're making. I know the need that's there. And then I was like [ __ ] it. I hope none of them come in this business, right? Like because I was like just stay away like keep doing your thing. And then it's interesting like during the great recession in 2008 2009 when retail went really bad and other things those guys all tried to come into our business and you know get into it like oh saying everything I've been saying for years you know captive audience you know slow and steady business. You know everyone you know mom and dad are always going to be there to pay their rent. all those things that I thought, you know, a long time ago were holding true.

So, as you're growing a business, um the people that you choose to bring onto your team or everything, whether it's a sports team, whether it's it's your early days. And so, hiring is is crucial, right? Especially hiring and promoting leaders.

I'm curious, David, um like what are some of the must-have attributes? like what do you look for when you're hiring andor promoting someone to be a leader that works for you?

I think one is trust. I need to trust them. Two is creating an open line of communication. Um three, I don't think you're a successful leader CEO if you're not willing to listen.

Um there are a lot of dictator type of CEOs. That's not me. Some of them work. I, you know, I don't manage from fear. I manage from kind of, you know, bringing in opinions. Um, and so for me, I think it's about having people that who in their individual swim lanes are better at those jobs than you are.

Interesting. So, I feel like life comes down to people and relationships and like you said, trust and belief that that person's a value added resource and that um they have the combination of competence and integrity. Um, that that's just how life works, right? That should that should be valuable valued in any position in your company, right? It shouldn't matter. So, you know, think about our real estate business, Campus Apartments. What we determined a long time ago was that the person who had the most interaction with our customers, our residents, okay, we have about 25,000 residents across the country, was not the property manager, not the vice president of of leasing, but the the maintenance person on the property.

Huh. And so like what we realized was training them to interact with our customers was paramount and the trust you have in them in the training was really important. And so we focused hugely on making sure that that person understood what the resident was going through. Thought thought thought to ask. So on our work orders if they were going to fix your light switch he would say, "Hey, you know, Jennifer, I noticed that you and your roommates haven't um renewed your lease yet. what's you know and like we would just give information and they would figure out Jennifer would say oh you know I'm not getting along with my roommates like it could have been anything but they'll get the real answer right and so he might go back and say to the leasing manager hey Jennifer in apartment 205 is having roommate trouble maybe we want to talk about getting them in different apartment next year right it could so

like we thought that that data was valuable and uh we still use it today wow I I love that the maintenance person, right? The they have their their guard down. They don't feel like they're being sold to, but take going the extra mile to train them to learn and be curious, right? It ends up being a big part of your business. I I think that's a really really

Think about that. That's in any business. Yeah. How are you greeted when you walk into our arena? Okay. That person swiping your ticket like welcome. What? Like all of those things that you can do to give somebody a great experience where that's somebody's night out, that's somebody spending their hard-earned money. Like I think it comes back to respecting people's time and money.

Mhm. And I feel like we've lost a lot of that in a society. And so like common courtesy matters to me. Um it matters to the businesses I'm invested in where it's like, hey, let's treat people well and let's like appreciate the fact that they spent money on whatever the product we're selling is.

Yeah. I well I just like the fact that you you one are thinking of that and then two care enough to say hey let's do let's do the extra work to show how much we care about the little things because those end up being the big things let's treat people with respect let's genuinely care for them that I think that that makes a a huge difference um I also was reading a story about was this the Shawn Jackson um I I think he was just kind illinformed about some things and made some bad comments. Are are you okay to talk about this? H how you I feel like handled that situation really well.

Yeah. Yeah. I um you know it's interesting um you know what happened in that regard was I think that and this was probably god five years ago maybe even longer but um Deshawn had made some anti-Semitic comments and I had friends that were friends with him and like I never like some people shoot first and ask questions later right?

Mhm. I don't I I just don't roll that way. So, I was kind of like I need to figure and so at the time I was you know in Philadelphia I'm kind of a leader in the uh Jewish community and you know some of the organizations. So people came to me and said like hey you know we need to cancel this guy or [ __ ] this guy like all these different things. And I was like you know what before before like I get there like I actually just want to find out what his intent was. Mhm.

And so a mutual friend of ours set me up, Michael Rubin actually, um was is closer to Shawn and and and we got together and I was like, you know what, like the things he said were based on some that he was just uninformed related to the hurtfulness of those words versus stuff that he heard. Um, and not only was he willing to understand that, but he went one step further and said, "Can you take me to your Holocaust memorial in Philadelphia and actually educate me?"

And I'll never forget, he came with his mom, you know, no press. We just walked around and talked.

Wow. And so, like, to me, like it would just be nice to be able to like, you know, take a moment before you're ready to convict somebody and like actually have a conversation. Well, I think there's so much learning from that, especially today, like right now, today, of of being quick to judge when we really should be quick to be curious about situations. Yes, there are times when people maybe are like have hate in their heart, but this is a good guy who was uninformed and made a mistake and instead of you and everybody else just saying, "Let's just get rid of this guy." I love that you had an open mind and you led with curiosity as opposed to judgment. And now, you know, he's better informed and he's like, "Oh, wow." And he probably feels better, too, about this David guy cared for me and he cares for me enough to be curious and that like the ripple effect, man. Like, do you think about that? Like the ripple

effect is far and wide when you approach people that way. I I think it's always harder to stop and take a minute and slow down than to just proceed right?

But like look, I can't tell you that I lived my whole life that way. I think, you know, experience is the best teacher, right? And I think you get older, you get some experience, you start thinking about this stuff, and that helps you kind of get to this point to uh, you know, call a timeout.

Yeah. You invest a lot uh as well. It's part of your your business. When you're looking at an investment opportunity, uh, a company, a founder, whatever, what is it that you're looking for? What makes you say, "Yep, okay, I'm going to write a check for that."

You know, first I really have to understand the product, right? Like, do I understand it? Um, or I joke, do my kids at least understand it now, right? Because in case I don't, and I'm serious. Like, I I'll call my daughter and I'll be like, hey, do one of you guys understand this? Uh um and like, oh, Dad, that's great. You know, um so, you know, that'll be number one. Number two, who's the founder? Okay, people matter. And I judge everything I do when I'm investing that before it starts and as I get to know this person, I'm like, if this thing goes bad and as long as the guy's not a crook or a criminal,

would I invest with him again or her? Because that's the people matter especially in small startups where you know, you know, they're out there with their product or, you know, idea. And so I need to understand the idea. I need to have deep affection for the founder and the management team. And then also I have to be more than just money in the deal. Um, and that's counter to a lot of people. Um, I like knowing when my influence and input can help make a difference. It feels like a sense of pride to me. Uh, and if I if I know I can make a difference, you know, as like a, you know, advisor, mentor, board member, whatever that is.

Yeah. How would you make a difference? Like introductions, sharing your knowledge. uh all of the above like what are the ways that you you add value to those deals?

Yeah, I think it's strategic thinking. Yeah. I think it's introductions and I think it's you know be a sounding board. You know the the hardest part about being a founder is they're afraid to tell you know their investors bad news.

Yeah. Right. And so teaching them that like hey bad news doesn't get better with time. like you know some of these founders are really young and so I'm like let's like you know and they think they have to be guarded and all this stuff and it's like hey let me just you know give you some thoughts on how to do this.

What what's one of your favorite investments andor founders that you've backed that you've been a part of.

I look I have a handful um there is a fintech that I'm involved with. They're actually Philly based so it's kind of you know affectionate to me. Um a a close friend of mine uh was uh one of the pioneers of the old internet bank ING direct. So it was kind of like a you know the first internet bank about 15 years ago. I don't know if you remember that. And then uh he partnered with uh two brothers in Philly who were on the tech side and really savvy. And we created this great fintech called Cred uh Cred.ai. And we created kind of this debit card that could create and establish credit for people in a different manner than a credit card does. Um, so where you're using debit, not credit. Um, it's kind of, you know, really smart product, great interface, one of the best I've seen. Um, and built this whole infrastructure that today can also powers, you know, where this, it's always like where's the puck headed?

Well, now stable coin issuance and all of that, these guys can be the rails to which that works on. And so really cool product here b b b b b b b b b b b b b b b b b b b b b b b b b b b b b b b b b b b b b b b b based here in Philly. Um it's just been a fun story.

Philly's got more of that than I think people realize, right? It's kind of a it's kind of a startup scene.

It it's getting there. You know, it's not New York or or you know, Silicon Valley or but Miami, but like Philly's got this a great vibe. Like if you don't understand it, you kind of look like what is it? But like, you know, proximity to New York and DC, great sports culture, great food scene, cost of living's reasonable. Like, I I think it's got it going on.

Yeah. So, I'm a big Philly cheerleader, you know. Yeah. I I I uh had a a gig that was homebased there uh a while ago and so sneaky good food scene. I loved walking around Philly, going to dinners with with friends and colleagues. It it's it's a cool spot, man. It was better than I I realized because I hadn't spent much time there, but then I was going there quite a bit and I I really like Philly. I'm I'm curious about the future of Philly, this arena project. What was it like for you to kind of take control of it and and run it and now it's kind of like in in motion? Uh what what's it been like for you? What was it like getting it all that stuff?

Yeah, you know, it's been an interesting journey. um not you know and so it started off where the Sixers where we were going to build our own arena uh in downtown Philadelphia. Um it was a arduous process. Um you know it it was kind of unique and you know one one of the few times you know not only time but few times where I really you know just um I said to my wife I said we're going to build this arena you know my partner Josh and David and I were like we're going to do something really special here. We're going to build it in downtown Philly bring it back to life.

um not take any uh city capital and uh also do you know some really good things for the city. People are gonna love us. It's gonna be great. Um you know, not everyone would believe that. And so, you know, we had a process. We had a fight. We did it. You know, we ultimately got it approved. But then, you know, for the good of the city, we came back together with Comcast, who owns the Flyers. Um and we're doing a great building together. Um and, uh I'm excited about it because it's going to be the best live entertainment venue in the world located in Philadelphia. We're going to open in 2030. Um we just got announced a WNBA team that we're bringing to Philly.

Um that'll start that season as well. So like, you know, for those of you who are like counting Philly out, like you're wrong. Um give us a chance cuz uh like we're doing great [ __ ] here.

I love it. Um I had read that one of your um core tenants of life was unconditional compassion. Can you tell me more about this core tenant of your life? unconditional compassion.

Yeah. You know, I don't know if it's unconditional. I think it goes back to kind of the Des the Desawn thing, right? Like, you know, I think that like I start with reason, you know, being reasonable and then decide if I'm going to go crazy or not, right? So,

I think this stemmed from a some did somebody uh vandalize and put a swastika on on the Holocaust memorial in 2024 and Yeah, that's where I read the story. Yeah. Okay.

Yeah. I mean, look, I obviously I wasn't happy and obviously I put up money to, you know, for a reward to find the person. Um, we didn't um I put a camera I paid for cameras. I did things to, you know, help uh uh you know, so like it's not about the compassion. I think it's about like you can either be frustrated and like it turns to hate or you can just like try to say like look, let's try and educate people. And so I think it just reinforced the need for a place like that in Philadelphia and in the world to have a place for education.

Yeah. Gotcha. It makes sense. Um I'm curious when you you mentioned uh a few times throughout the course of our conversation, David, that um things you try to say when you meet with people who are a bit earlier in their career. And so I am curious to think about like a I don't know, maybe a college grad or somebody who's early to mid20s and they want to leave a positive dent in the world like you're doing, but they're not 100% sure yet what they want to do. What are some general pieces of life slashcareer advice you give to that person?

Yeah, I I think it's, you know, try to get noticed for the right reasons. Um, which is why I firmly believe like, you know, show up and go to work and, you know, go get coffee when you see your boss's boss there who wouldn't know you because you're on some random Zoom. Okay? Don't be afraid to introduce yourself. Put yourself out there. I think so. I think doing things like that are important for your career. asking lots of questions, being the guy in the room or girl in the room who didn't understand something and says like, "Could you explain that to me?" Because I think folks in my position really respect that because they get that most people are too afraid to do that. Um, and then like don't be afraid to put out a bad idea. Like you, you know, like think about all these people in these different companies where something great happened because somebody had an idea and had the courage to come forth

with it. It could have been a piece of technology. It could have been anything. But like don't be shy. Love it. Love it. Dave, this has been amazing, man. I appreciate um you and I appreciate your team connecting us. It's really, really cool getting to know you and just doing all of the reading leading up to this. Where would you send us to learn more about you online?

Yeah, you know, my family office, Darkco Capital, um we've got a pretty good website. It shows um what we're doing, the companies we're invested in, talks about Philly and how important that is to me and philanthropy as well.

Nice. Why' you name it that? Um you're going to laugh. So when I needed a name for my family office, I was like, you know, everyone has these cool names and like, you know, Blackstone and Apollo and, you know, like all these companies had great names and I'm like, you know, like what am I going to call my thing, right? And like my I didn't know that my thing would be what it is today either, right? We just started investing and it turned out to be okay. Um, and so literally Darkco D- A RC David Adelman Realy Company. Okay.

Like I mean, you know, because now people like do people know Darko out there, but they're like they no one knows what it is. But like I literally was so not creative. Like that's not this.

I think it sounds cool. I like it sounds cool. It sounds cool now, but when you're like you couldn't think of it and you're like trying to draw stuff out. It was uh Yeah.

I love it, man. Well, thanks again uh for being here, man. I love it. I would love to continue our dialogue.

Yeah. Come visit in Philly, man. We'll go to a Sixers game. We'll have dinner. Like we'll do the whole scene.

I'm in, man. I'm in. I'm in. I appreciate it, man. Thank you so much. I appreciate you. Thank you.

All right.

Questions about this episode

Who speaks in "He LOST A BET and Ended Up Owning an NBA Team | David Adelman’s Billionaire playbook"?

Ryan Hawk (Host), David Adelman (Guest), Allan Horwitz (Guest), Josh Harris (Guest), David Blitzer (Guest), Michael Rubin (Guest), DeSean Jackson (Guest), Blaine (Guest).

What is "He LOST A BET and Ended Up Owning an NBA Team | David Adelman’s Billionaire playbook" about?

David Adelman's journey to becoming an NBA team owner began with a childhood bet that set the tone for his unconventional approach to life and business. Emphasizing the importance of embracing challenges and learning from failures, Adelman shares his mantra of living without the constraints of traditional paths, advocating for active listening and the willingness to experiment with new ideas in…

What is mentioned in this Ryan Hawk episode?

29 people, works and ideas are mentioned, including DeSean Jackson, Philadelphia 76ers, Student housing, Selling, Campus Apartments, Why not me and why not now?. Each one on this page links to its own page with every episode that mentions it.

How long is "He LOST A BET and Ended Up Owning an NBA Team | David Adelman’s Billionaire playbook"?

The episode runs 51 min; the transcript is about 10,808 words in 140 timestamped sections.

More from Ryan Hawk

About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated January 24, 2026.