Embracing failure and pulling the plug

David discusses failing fast, learning from mistakes, and when to exit investments or projects.

Play episode from 14:10

chevron_right

Transcript

chevron_right

Transcript

Episode notes

Go to www.LearningLeader.com for full show notes

This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver.

My guest: David Adelman is the CEO of Campus Apartments, founder of Darco Capital, and co-owner of the Philadelphia 76ers. During our conversation, we discussed how losing a basketball bet at age 11 changed his life, investing his bar mitzvah money in real estate, becoming CEO at 25, his grandfather's Holocaust survival story, and why it gives him perspective on struggle, embracing failure, the trade-offs of building something excellent, and what he looks for when hiring leaders.

Key Learnings

"Why not me? Why not now?" David's mantra cuts through all the overthinking and excuses we make. When he saw other people building national real estate portfolios, he didn't wonder if it was possible—he asked why he couldn't do it. Stop waiting for permission. Stop waiting for the perfect moment. Ask yourself: why not me? Why not now?

Make mistakes, just not the same one twice. David doesn't expect perfection from himself or his team. He expects learning. Fail fast, fail forward, but don't repeat the same failure. That's not growth—that's negligence. Embrace the suck, but evolve through it.

David's grandfather survived the Holocaust after his wife and children were murdered. He escaped, joined the resistance, and rebuilt his life from nothing. When David thinks about that, he says: "No matter what, I don't know struggle." That's perspective. Most of what we call struggle is just discomfort. Understanding that doesn't make your challenges disappear... It makes them manageable. If your grandfather could survive the unthinkable, you can handle the hard day in front of you.

At age 11, David challenged family friend Alan Horwitz to a basketball game and made a wager. Horwitz didn't let the kid win, and David lost his basketball, football, and baseball glove. To get them back, he had to go to Campus Apartments every Saturday to sweep sawdust and stack lumber. This losing bet became his entry into a billion-dollar career.

At 13, David gambled his $2,000 bar mitzvah money by investing it with Horwitz in a building at 45th and Pine Streets in Philadelphia - a property his company still owns today. By age 17, he bought his first solely owned investment property.

David was accepted into Temple University Beasley School of Law but chose to become a Property Manager at Campus Apartments instead. At age 25 in 1997, he became CEO of Campus Apartments.

His grandfather, Sam Wasserman, was captured by the Nazis in 1942 and taken to the Sobibor concentration camp, where his wife and two children were immediately executed. Wasserman escaped during an organized revolt, joined the resistance, was wounded in battle, and was cared for by a woman named Sophie, who became his second wife. David said, "I feel a deep connection to him and what he went through. It's more like a sense of duty to honor him."

David says, "I bet on jockeys, not horses. I ask, 'If the thing fails, would we support them again?' To be clear, a lot of our [investments] are going to fail.' He learned the hard way: "Friends would say, 'Here's a deal, put in X amount,' so you know, it's $250,000 or $500,000 or $1 million. I realized very quickly that it's probably a money-losing prospect to just invest in a friend of a friend's idea or because someone at your country club is investing in it."

"It's called working off your debt." I literally lost everything to my "Uncle" Alan in 30 minutes when I was 11. My baseball glove, football, basketball, even my bank book. Every Saturday, I had to stack lumber and sweep sawdust to get one item back. Two years later, at my Bar Mitzvah, my parents asked if I wanted to give my gift money to my grandfather, who was good at picking stocks. I said no, I want to give it to Uncle Alan and buy real estate. At 13, I drove around with him, picked the biggest building he owned, handed him $2,000, and became a partner.

My grandfather was in Poland with a wife and two kids when the Nazis rounded him up. There were two lines. One for men, one for women, and children. He never saw his wife and kids again. He escaped from the Sobibor prison camp, became a freedom fighter, got shot, and was in a hospital recovering when a woman checking on her brother saw this lonely soldier and went over to check on him. That was my grandmother. My mother was born in a displaced persons camp after the war.

"No matter what, when I'm getting the crap kicked out of me in business or anything else, I don't know struggle." I think about my grandfather and what he went through. "That guy knew pressure and made it through the other side. So I have to stop being a little bitch about it and lean in."

Uncle Alan always said, "Whatever you do in life, it shouldn't feel like work." I have never said I'm going to work. I say I'm going to the office. Now, am I tired sometimes? A hundred percent. Did I miss a lot of stuff with my kids? Absolutely, and I have deep regret over that. With success and money comes a price, too.

Becoming a CEO at 25. "Why not me and why not now?" I live my life by this mantra. In the 1990s, no one was doing student housing at large scale nationally. I saw this white space, and I'm like, fuck it, let's do it. "I'm not afraid to fail. And I think if you're not afraid to fail, it's a freedom."

"Embrace the suck." Not everything's gonna be fun. Some things are hard. But sometimes when you push through them, you get to another side. Sometimes you don't, and pulling the plug is okay if it's not working. I've gotten good at understanding that a business might be a great opportunity, a great idea, at the wrong time.

When building something…If you aren't willing to make sacrifices earlier in your career and build that foundation for the future, being an entrepreneur might not be for you. I made choices to miss things with my wife and kids. Were all those things I missed worth it? Probably not. My daughters are 21 and 23 now, and I missed a lot of their early growing up. Four years ago, I apologized to my older one, and she said, "You know what, we remember this dad more than that dad." "It's never too late to make a change."

After you've done okay financially, it has to be about something else. The guys and women I roll with—"it's not about money. You either are wired to get up and work hard every day and do it, and it has to be about something else." It could be about providing opportunities for the people who work with you, or solving complex problems, or creating a business you're excited about.

"I don't think I'm the smartest guy in the room." You have to be open to learning. I continue to want to learn about other people's businesses. If I meet somebody, I'm like, tell me about that business. If you have that inquisitive mind, some guy tells me he's in the widget business, and I'll think of ten things they should try to do.

"I am never too embarrassed to say I don't know something." When we were selecting architects and contractors for the arena, I spoke to owners of the newest stadiums. Just lessons learned about the process. When I mentor kids, I tell them most people are afraid to say "I don't know" or "I don't understand." "If you're embarrassed for looking stupid, isn't it worse if you don't know what you're doing down the road because you didn't ask?"

"People don't know how to listen anymore. People wait to talk." They don't listen. When I have dinner with my youngest daughter, I hand her my phone so I won't be on it. I want to be there, I want to be attentive. Why are you wasting time meeting with people if you're not gonna listen to them?

"Make lots of mistakes. Just don't make the same one twice." Try hard. Don't be afraid to put yourself out there. The worst thing that happens is someone says no. I met my wife in a bar, literally in line for pizza. Turns out she was the school teacher two different women had told me I needed to call. The funny part is my buddy was talking to her best friend. He married her, I married Hailey, and our kids are best friends.

When it comes to sales. "Don't bullshit people. That's my number one goal." People can tell. Even at an early age, I had the humility to say I don't know everything. Here's my business plan, here's why I think I can scale Campus Apartments across the country when that wasn't being done.

When I'm hiring or promoting leaders, I look for three things. One is trust—I need to trust them. Two is creating an open line of communication. Three, "I don't think you're a successful leader or CEO if you're not willing to listen." There are a lot of dictator type CEOs. That's not me. Some of them work. "I don't manage from fear, I manage from bringing in opinions." For me, it's about having people who, in their individual swim lanes, are better at those jobs than you are.

The DeSean Jackson situation taught me about leading with curiosity. He made some anti-Semitic comments, and people came to me saying we need to cancel him. "Before I get there, I actually just want to find out what his intent was." The things he said were based on him being uninformed about the hurtfulness of those words. Not only was he willing to understand that, but he said, "Can you take me to your Holocaust memorial and actually educate me?" He came with his mom, no press. "It would be nice to take a moment before you're ready to convict somebody and actually have a conversation."

When I'm looking at investments, I really have to understand the product. I joke, "Do my kids at least understand it?" Number two: Who's the founder? People matter. I ask myself, if this thing goes bad, and as long as the guy's not a crook, would I invest with them again?

"I have to be more than just money in the deal." I like knowing when my influence and input can help make a difference. I think it's strategic thinking, introductions, and being a sounding board. The hardest part about being a founder is that they're afraid to tell investors bad news. "Bad news doesn't get better with time."

Advice to young professionals. "Try to get noticed for the right reasons." Show up and go to work. Go get coffee when you see your boss's boss there. Don't be afraid to introduce yourself. Ask lots of questions. Be the person who says, "Could you explain that to me?" Folks in my position really respect that. "Don't be afraid to put out a bad idea."

I hate working from home because I think people are screwed by the opportunity to interact with people and better their career and learn things. You're robbed of chance encounters, of overhearing conversations, of learning by proximity.

We're building this arena in downtown Philly, not taking any city capital, and doing good things for the city. We came together with Comcast who owns the Flyers. "It's gonna be the best live entertainment venue in the world, located in Philadelphia." We're opening in 2030 with a WNBA team. For those counting Philly out, you're wrong—we're doing great shit here.

Reflection Questions

David's grandfather survived the Holocaust, which gives David a profound perspective on what real pressure and struggle actually look like. What experiences in your own life or family history could you draw on to reframe the "struggles" you face in your work or personal life?
He lives by the mantra "Why not me? Why not now?" and says that not being afraid to fail is a freedom. What opportunity are you currently overthinking or waiting on "permission" for? What would change if you asked yourself those two questions right now?
David regrets missing parts of his daughters' childhoods while building his businesses, but his daughter told him, "We remember this dad more than that dad." Meaning it's never too late to make a change. What relationship in your life needs you to show up differently, and what's one concrete thing you could change this week?

More Learning From The Learning Leader Show

#126: Jayson Gaignard - Mastermind Talks

#273: Chip Conley – How To Be Wise Beyond Your Years

#476: Kat Cole - Reflection Questions, Humble Confidence, Building Trust

Time Stamps:

01:51 David Edelman's Early Lessons in Business

03:58 Investing at a Young Age

06:12 Family History and Holocaust Survival

09:53 Balancing Ambition and Family

18:17 Sustaining Excellence and Learning from Others

25:38 The Art of Listening and Being Present

26:16 Lessons from Childhood and Parenting