How Jason Oppenheim Sustains a Strong Team

Jason Oppenheim, president and CEO of The Oppenheim Group, learned the importance of having a strong team during his time as a lawyer. But when he later switched careers and created his renowned real estate firm, it was difficult to let go, trust others, and delegate tasks.

Now, Oppenheim sustains a strong, happy team to help the company thrive – even while cameras follow their work lives in the Netflix series "Selling Sunset" and "Selling the O.C."

During a recent episode of Office Hours, Oppenheim explained how he aims to create a positive, productive atmosphere where everyone feels empowered.

1. Listen to yourself.

First and foremost, listening to yourself matters, Oppenheim noted.

“I believe in myself and my own critical thinking skills, in my own decision-making skills,” Oppenheim said. “That's probably why I'm successful. If I were to point to one thing, it’s that I believed in my own abilities.”

Additionally, Oppenheim makes sure to take time for personal reflection to help cultivate happiness, he said.

“If you can remember to try to keep perspective and think about the things you're grateful for and that the problems that you have are not significant, I think you can achieve a higher level of happiness,” he said.

2. Learn to trust others.

Though he admittedly thrives under pressure, Oppenheim had to learn to lighten his individual workload at the firm to find greater success.

“I was working so hard that I was getting tears down my face at night because I was so stressed out. I was working 14 hours a day and super overwhelmed,” he said. “I don't think it's healthy and sustainable.”

To move forward, Oppenheim had to let go and start building a team of trustworthy people who can think for themselves, he explained.

“That was the toughest part: eventually learning to let go of every single detail and being so obsessive. In order to grow, you have to start delegating,” he said. “When I started delegating, my whole world changed, and I was able to expand the business. That means hiring really good people and paying them really well.”

3. Create a happy workplace.

According to Oppenheim, supporting his team is crucial – similar to how he checks in with himself.

“Every three to six months, I really ask myself, ‘How happy have I been [from] one to ten? How happy have I been at work?’” Oppenheim said. “I even [ask] my own employees. I think everyone should reflect on that.”

Similarly, he seeks people who have unique ideas and aren't afraid to share them. It can be easy to get stuck in routines at work, he noted, and taking a "holistic approach" can be much better.

“I like people who are like, ‘What if?’" Oppenheim said. "Think for yourself.”

Believing boldly in the team he built, Oppenheim created an ad in The Hollywood Reporter showing and celebrating the team. It's what caught the eyes of producers and led to the Netflix series, giving the company even wider notoriety.

The Takeaway

Jason Oppenheim carefully crafts a strong team culture so his business can thrive – even while in the limelight. No matter what industry you’re in, entrepreneurship isn’t typically a one-person show. It can be important to lean on others – listening to your ideas and finding trustworthy people to help you forge forward.

This article is part of Office Hours, a series that connects you with entrepreneurs and expert tips for running and growing a business right now. Find their can’t-miss conversations here.