The Richest Self-Made Woman In Real Estate Shares Her Best Advice (2024)

How did Dottie Herman become the richest self-made woman in real estate?

As CEO of Douglas Elliman, Herman sits at the helm of one of the nation’s oldest and largest real estate brokerage firms with approximately $27.4 billion in annual sales volume and 7,000 real estate agents.

From her roots as a real estate broker on Long Island in New York to buying Douglas Elliman with her partner, Howard Lorber, Herman is a self-made entrepreneur who is the go-to name for all things real estate.

I interviewed Herman on a variety of topics, including the real estate business, her best advice to entrepreneurs, the one mistake never to make in real estate, what she learned from personal tragedy, and her morning and nighttime routines.

Zack Friedman: Real estate is a relationship business. How have stronger relationships helped foster your career?

Dottie Herman: Most businesses are relational, but especially real estate. It’s all about your relationships.

I truly believe in getting to know people, which generates authentic relationships. That’s why I make it a point to get to know all of the agents and employees who work for my company. This personalization creates a positive rapport, especially with new agents. But I don’t limit myself to our real estate agents.

I want to create strong connections with everyone within the organization regardless of where they work. As a hands-on CEO, I want to hear all perspectives, which helps our company thrive. When we opened new offices in another market, I got to know the local press and merchants. Talking with the locals helped me understand the needs and wants of our perspective customers.

Zack Friedman: Who believed in you before you made it big, and what did you learn in the process?

Dottie Herman: I had a boss at Merrill Lynch named George Rathmann. He always said, “I was a diamond in the rough.”

He saw the potential in me that I was too young and inexperienced to recognize in myself.

I also had a few wonderful mentors, including Diane Nash, who like George saw something in me that no one else did at the time - she always inspired me to be the best I could be.

And finally, my partner at Douglas Elliman, Howard Lorber, believed in me so much, he invested in my business.

Zack Friedman: What’s your best advice to your 20-year-old self?

Dottie Herman: To do what I did, you must reach for the stars.

I’d tell my 20 year old self, “do not let any obstacles stop you. Where there are obstacles there are also great opportunities.”

And most important, I’d drive home how important it is to get to know the people that truly make the decisions within the company you work for.

Zack Friedman: What’s the biggest mistake that people make in real estate?

Dottie Herman: A lot of agents are not consistent. When you work on a big deal for months and it falls apart, you can see people who go into a downward spiral, and struggle to get out of it, and if you are in a rabbit hole, you won’t be able to see the light of day at the same time.

People need to remember that every experience is a teachable moment, and you need to brush yourself off and start again. If you have disappointments, feel bad for yourself for a day or two, then get yourself back in the game.

One of my favorite quotes is, “Success is failure turned inside out.”

Zack Friedman: You experienced a tragedy at an early age. How did that moment impact you?

Dottie Herman: My family was in a terrible car accident that took my mother’s life.

Through that experience, I realized life can end or change in a nanosecond.

Because I lost my mother when I was just 11 years-old, but also the oldest child in our family, I became extremely independent. I had to do a lot on my own that other kids my age weren’t doing. I also learned how to take risks and how to assess the relationship between risk and reward.

Zack Friedman: What is the future of real estate and the role of technology? What do you say to those who think technology will replace human brokers?

Dottie Herman: I think technology and information regardless of how it’s delivered is very important.

However, I believe you need the human element to help navigate through that information and technology platform. It helps to have someone who is familiar with the local markets that you may be considering buying in.

Zack Friedman: What are your three best pieces of career advice?

Dottie Herman:

1. Never let obstacles stop you; figure out a way around it.
2. Be real and authentic.
3. Be passionate about what you are doing.

Zack Friedman: What is your best advice to a startup entrepreneur?

Dottie Herman: Have a business plan and decide how you are capitalizing it.

Most businesses that do not make it fail because they are under-capitalized.

Be willing to eat, sleep and breathe the business. Success doesn’t sleep and it doesn’t wait for anyone. You earn it through hard work and being the best you can be.

If you are hiring people, find the best. If you do not have the capital to hire the best, make sure you train them the way you want things done, especially someone who is new to the business but shows great ambition and potential.

Zack Friedman: What’s your morning routine? Do you have a nighttime routine?

Every morning, I have a cup of coffee and read the New York Times. Then I work out for one hour, either going to a spin class or hitting the gym.

At night, I always finish going over emails that I was unable to get to during the day. When I complete that, I love doing crossword puzzles.