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7 Key Leadership Insights From a Real Estate Mogul

Real estate executive Nick Segal on what it means to lead with integrity and why not selling is the key to his success.

Nick Segal wears his heart on his sleeve.

“If I’m leading from my heart, I’m never wrong,” he says. “Because my heart has no other agenda, other than to express love.”

If you think that’s a disarmingly tender sentiment, coming as it is from one of Southern California’s most powerful real estate executives, you don’t know Nick.

“Ego is great to get us out of bed in the morning,” says Nick, a senior executive with luxury real estate brokerage Compass in Southern California. “Then I think we ought to check it right there. Leave it on the pillow and bring our hearts forward. Let’s communicate from that place, because those are far more compelling and engaging conversations.”  

That deep compassion for others was forged in the midst of incredible adversity. 

His parents divorced when he was a year old. When he was just 13, his mother committed suicide, which turned his “world upside down.” After his mother’s passing, Nick went to live with his father in Los Angeles. Unfortunately, just over a year later, his father died of colon cancer.

“Suddenly orphaned at 14 years old, life as I’d known it was no more,” Nick says. “It was just a memory.” 

Despite immense tragedy at such a young age, he went on to become a business success.  

Nick’s soulful leadership style has evolved over three trailblazing decades in the real estate industry. He’s an in-demand speaker on entrepreneurship, a business coach and the co-author, with his wife Laura, of On Your Terms: Discovering a More Joyful and Purpose-Filled Life Through Value Conscious Negotiating. In our wide-ranging conversation, he shares a few key insights on his backstory, what it means to lead with integrity and why not selling is the key to his success. 

1. Channel pain into empathy

Nick clearly had a rough start early in life. But, bolstered by the support of his aunts and uncles, he found a place to belong. 

Nick packed his bags for George School, a prestigious Quaker boarding school in Bucks County, Pennsylvania. There, he found stability and community. 

“That’s where I took up roots. I started getting into leadership roles, too. I saw the opportunity to not only be accepted, but to create a place for myself,” he says.

Back then, Nick approached success from a survival mentality: “I took on this mentality of, I’m fine. Don’t worry about me. That demonstration of feigned courage was the opportunity to survive, belong and not call undue attention to myself.”  

With the benefit of hindsight, he now sees those difficult years as “a blessing in certain respects,” he says. 

“It gave me perspective and a sense of compassion. When people tell me their stories, I kick in to another level of empathy, because I’ve experienced so much loss and pain myself. I immediately connect with people, whether in business or personal relationships.”

2. Grow and take risks relentlessly

For Nick, experiencing profound loss and grief offered another valuable insight.

“I found what the bottom was,” he says. “I started taking risks relatively soon after my parents passed. I realized that no matter what the outcome, it wouldn’t be worse than what I’d already been through.”

In that spirit, Nick set his sights on Hollywood. He was no stranger to the entertainment business –– his father, Fred, was a screenwriter, and his uncle is the award-winning actor George Segal. In his 20s, Nick appeared in “Breakin’ 2: Electric Boogaloo” and a few horror flicks before he took on a new role: real estate agent.   

While working as an actor on a commercial, he met a man who worked in real estate. “I said, ‘well, what is that –– real estate?’” Nick remembers. “He answered, ‘Well, you take this book around, and you show people houses…’

“It seemed very nondescript, but I said, ‘I can do that.’”


At the time, Nick was 28 and newly married. He and his wife had just adopted their first child. “I  thought: I gotta lay down my acting cleats and get into something that has a little more stability,” he says.

He joined DBL Realtors, which was then a small, young firm. “I was the twelfth agent there,” Nick says. “I started to work one-on-one with people consistently. I found out what worked, and what didn’t. And I realized that if I was selling, I was pushing people away. But if I was offering genuine value to the best of my ability, people would be attracted to that.”

Although he was still relatively new to the business, Nick consistently looked for ways to innovate. For example, he  came up with a unique service guarantee for DBL’s residential real estate transactions. 

“I proposed that if we don’t honor everything that we say we’re going to do on your behalf, in the sale of your home, you can cancel the listing with twenty-four hours’ notice,” he says.

Nick, who was already writing that promise into his contracts, asked a DBL executive for feedback. His reply?

“Let’s make it a company policy.”

Through those kinds of customer-service-driven innovations, Nick helped build the firm into a 650-agent powerhouse that was eventually acquired by Sotheby’s in 2004.

“They started to see that they could do things differently. And we grew a company,” he says. 

3. Keep your word –– and value your time

Nick’s father taught him valuable lessons about keeping promises –– and sticking to personal priorities. 

“Once, we were on set at Warner Brothers, and a very famous actor, who my father knew from New York, came up to him said, ‘Fred! Oh my gosh, you’re here now. We gotta get together.’

“My father –– who was impeccable with his word –– just smiled and said, ‘Well, we’ll see.’” 

Afterward, Nick asked his father whether he planned to meet up with the actor. 

“He replied, ‘I’ve got enough friends,’” Nick recalls. “I realized, in that moment, that time is precious. It’s stayed with me to this day. I’m very judicious with my friends.”  

And just like his father, Nick keeps his word.  

“If I say I’m going to do it, I’m going to do it,” he says.

4. ‘Share your why’

Nick’s philosophy on building strong teams is to start with yourself.

“Get clear about what you want to achieve,” Nick advises. “Stay true to what you want to do and how you want to do it. Share your why. Those who are inspired to be a part of it will help do the heavy lifting –– the ‘fox-holers,’ as I call them, the ones who are truly in it with you.” 

What about the people who aren’t as committed to your vision?

“Let them go,” he says. “Let them self-select out, and don’t take it personally.”

5. Lead by example 

“I would never ask someone to do something I wouldn’t do myself.  If I’m going to suggest something, I’m suggesting it because I’ve already tested it out, and I’ve already got a degree of confidence that it works,” Nick says of his management style.

He avoids directing people’s actions and energies — it’s more powerful to make a suggestion.

“You’re going to hear me say, ‘For your consideration, you may want to think about this. This has served me well.’”

6. Raise your vibe

Fast-forward to 2009. Nick’s next act –– a bold one, in the middle of a financial crisis –– was to build a new real estate company from scratch.

“I started Partner’s Trust to raise the level of integrity and consciousness in our industry,” he says. “And we achieved that.”

The company announced its new venture with a full-page ad in an industry publication that proclaimed: Proudly serving our community since last Thursday. 

That’s emblematic of Nick’s leadership style, he says. “Let’s bring humor and joy into what we’re doing. This is not that serious.”

Eight years later, in 2017 –– after more than $11 billion in sales –– Nick and his partners sold the firm to San Francisco-based Pacific Union International. In 2019, the company merged with New York-based Compass.

“Now we’re part of the third-largest company in all of brokerage in the United States,” Nick says. “I’m still getting my arms around it: rebranding, a new culture … what’s keeping me in alignment is staying true to my heart.”

7. Lead with value and take it slow

What does heart-first leadership look like in practice? Start by pumping the brakes.

Early in his career, Nick “tried to sell. Oh, god, I fell on my ass so many times trying.” 

He soon realized that the hard sell wasn’t effective. Instead, he explains, “I took a leap of faith and said, I’m not going to try to sell you anything; I’m just going to tell you: here’s what it is. Does this meet your needs?”

Providing information to enable people to make informed decisions is a key communication element for Nick. It was a game-changer for him. 

“Consistently, people opened up. We had conversations about the best way to proceed, as opposed to how quickly could we get to ‘we’re proceeding now.’ 

“The quality of my life got better, because I slowed down enough to trust that what I had to offer had real value, and to claim that.”  

For Nick, that’s actually where the key to financial success lies: “Money takes care of itself if the service, effort and integrity are fulfilling.”

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