“Don’t preemptively judge people based on appearance” With Jason Hartman & Deidre Woollard

Don’t preemptively judge people based on appearance — one of the things I learned from interviewing people in the luxury industry and this holds true for real estate is that you can’t determine who someone is based solely on appearance. Stick to data like proof of funds, etc. As a part of my series about […]

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Don’t preemptively judge people based on appearance — one of the things I learned from interviewing people in the luxury industry and this holds true for real estate is that you can’t determine who someone is based solely on appearance. Stick to data like proof of funds, etc.

As a part of my series about strong women leaders of the Real Estate industry, I had the pleasure of interviewing Deidre Woollard.

Deidre Woollard is a writer and editor focused on the real estate industry. She created the first Estate of the Day column online and covered real estate and luxury for She later became part of the social media and public relations team at before serving as a publicist and marketing expert at several luxury brokerages in Los Angeles. She has helped publicize the sale of some of the world’s most famous homes. She co-founded a boutique public relations firm before leaving to join The Motley Fool and help building Millionacres into a brand that serves all real estate investors. Her passion for affordable housing solutions has led her to work with a variety of nonprofits including Giveback Homes and she is a member of the Urban Land Institute’s Housing Initiative Council.

Thank you so much for doing this with us! Can you tell us the “backstory” about what brought you to the Real Estate industry?

Ibecame interested in real estate when I started covering luxury real estate for a website called It was part of an early blog network that later became part of AOL. Through that role I met many real estate agents and started to learn more about the industry. Every move I took after that was to help me learn more about the real estate industry.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

For me one of the most interesting things was being part of the world of celebrity real estate and learning how houses are marketed. There’s an art to the way that celebrity homes are presented, you have a large budget for promotion but what it really comes down to is finding the story that appeals to the potential buyer. That is something that is accessible to anyone, no matter the price point of the house. When you really know who the house will work for and who that potential buyer is, you can find the way to target them effectively.

Are you working on any exciting new projects now? How do you think that will help people?

I’m really energized by my work with Millionacres. Our mission is to demystify real estate investing and show people how many different ways you can invest in real estate. You don’t have to be a landlord to make money and real estate. And if you do want to be a landlord, we can show you what you need to know and what to avoid.

What do you think makes your company stand out? Can you share a story?

We were started by The Motley Fool which has a heritage of taking complicated investing information and making it fun and easy to understand. We are so excited to bring that same idea to real estate. One of the things that makes us stand out is that our writers are investors. We own shares of REITs, we participate in real estate crowdfunding, some of us own rental properties or commercial real estate. It’s that level of engagement and skill across so many real estate disciplines that makes us special.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I worked for a great broker in Los Angeles, Nick Segal, and he wrote a book on value conscious negotiating. He also taught it to agents and one of the things I learned in helping him run some of those classes was that negotiating isn’t about one side winning and the other side losing. You have to both leave the table feeling confident that even if you didn’t get everything you wanted, you were listened to.

Ok. Thank you for all that. Let’s now jump to the main core of our interview. The Real Estate industry, like the Veterinarian, Nursing and Public Relations fields, is a woman dominated industry. Yet despite this, less than 20 percent of senior positions in Real Estate companies are held by women. In your opinion or experience, what do you think is the cause of this imbalance?

For men, the path to leadership is often more clear and more expected. There may be a lot of women who want to be in a leadership position but may not know if they are ready for that role. There is also a perception that women can be better at the soft skills but are not as good at other facets of leadership. Management and leadership are two separate skill sets, women have natural abilities toward both but often get tasked with managerial tasks. Leadership requires stepping back from day-to-day responsibilities to embrace a larger vision. That’s a challenge for some women, including myself.

What 3 things can be done by a)individuals b)companies and/or c) society to support greater gender balance going forward?

Women really need to support each other in leadership. There is room for all of us. I’ve worked with a group called WomanUp which was started through the California Association of Realtors, and they have focused on women in real estate leadership, mentoring and supporting women who want to build their own brokerage or take a leadership role in an existing brokerage. Think about building the next generation of great female leadership.

Watch out for the ways bias sneaks in. There is sometimes an underlying assumption that women don’t understand mathematical concepts as well as men. Commercial real estate has traditionally been far more male than residential real estate because it’s seen as being more numbers-focused. We need to encourage more women into commercial real estate and create a better environment there.

Have a clear set of standards and performance metrics that are fair and balanced. There’s more than one way to be a success in real estate and it’s not always about aggressive salesmanship.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

Women tend to lead with their expertise rather than their confidence. Sometimes we wait to be asked to lead rather than stepping up. Men are more likely to say they can do a job even if they don’t meet all of the requirements.

Women are also more likely to be caregivers of either children or aging parents and may need more flexible hours. Women work incredibly hard but may not do so sitting at a desk from 9 to 5.

Can you share 3 things that most excite you about the Real Estate industry?

Right now I’m really inspired by seeing how many women in real estate are really thinking about the issues of society and the ways that real estate plays a role. There are a variety of incentive programs in real estate that are encouraging affordable housing development and growth in areas that need support. I’m really excited by what technology can do not only in streamlining the real estate process but also taking the construction process in new directions.

Can you share 3 things that most concern you about the industry? If you had the ability to implement 3 ways to reform or improve the industry, what would you suggest?

I feel that the industry has always struggled with a poor reputation. Agents are portrayed as greedy and commission-focused, landlords are seen as working against tenants, and developers are seen as wanting to destroy neighborhoods. None of that has been my experience in this industry. I know thousands of great agents who want the best for their clients. Many of the landlords I have met are committed to providing a great tenant experience. Developers are becoming smarter about working with communities. This isn’t universal but it’s out there and we need to magnify the good.

If I could reform the industry, I would first say that everyone in real estate should have to study the history of fair housing law and understand the ways that bias works in the industry.

I would like to see the services that teach real estate investing be held to a much higher standard. Too many people pay money for programs that don’t work and wind up in trouble. Be careful when following anyone who tells you they have the “one way” to make money in real estate.

I would like to see the transaction process be moved completely away from paperwork and into an online world. There are some great companies that are building smart transaction platforms that show both sides exactly what is happening in the process.

What advice would you give to other leaders to help their team to thrive?

I believe in open communication. Create an environment where people can come to you and share if they make a mistake. So many times in real estate, it’s lack of communication that can stop a deal. Systematize your business as much as you can and make that system easy to follow.

Ok, here is the main question of our interview. You are a “Real Estate Insider.” If you had to advise someone about 5 non intuitive things one should know to succeed in the Real Estate industry, what would you say? Can you please give a story or an example for each?

Don’t preemptively judge people based on appearance — one of the things I learned from interviewing people in the luxury industry and this holds true for real estate is that you can’t determine who someone is based solely on appearance. Stick to data like proof of funds, etc.

Document everything — in both residential and commercial real estate, networking and relationships are a huge part of the equation. It’s a big industry but also a small one. Document calls, save texts, note interactions etc. This not only keeps the information out of your head where it can be forgotten but you never know when you are able to make new connections based on information you’ve already learned. A good CRM can help you keep things organized.

Understand the basics of construction, HVAC and plumbing — You don’t have to be as knowledgeable as a general contractor but if you are going to be doing real estate deals you need to be conversant in the core issues that impact both residential and commercial buildings. That starts with the land and the foundation and all aspects of the building. You can rely on your inspectors and appraisers sometimes but you have to understand what they are talking about.

Continuing education is a gift, not a chore — Many agents grumble about CE requirements but really everyone in real estate, investor, agent, developer, should constantly be learning. Real estate is always changing, zoning is always changing, stay engaged in the industry and in your community. One of the reasons real estate has fascinated me for so long is that it is always new. At Millionacres, our goal is to be a toolkit for people who know they need to always be learning to stay in the game.

Find the extra — Real estate is very competitive. People fight for deals and there’s that kill or be killed mentality. Instead of engaging in combat, find the thing you can do that might surprise or delight someone. It can be a gift, a note, it can be helping the other person get a win in some way perhaps by providing them with a great resource.

Because of your position, you are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

If I could build a movement it would be around how people consider affordable housing. I’m really inspired by some of the great design I’m seeing out there and the innovative ways people are using modular construction to create affordable housing that is easily accessible. Safe and secure housing is one of the core fundamentals that determines a child’s success in the world. Think of affordable housing not as a necessary evil or something that you have to do. There are ways to build developments that incorporate affordable housing and still provide profits for the developers and investors. Real wealth is about money but it’s also about doing what is right in the world.

How can our readers follow you online?

Visit or follow @Millionacres on Instagram.

Thank you for your time, and your excellent insights!

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