Increasing Diversity In Real Estate Investing With Deidre Woollard

REW 25 | Diversity In Real Estate


Real estate is a male-dominated industry where women are underrepresented and have a hard time breaking through. Calling for an increase in diversity in real estate investing Moneeka Sawyer interviews writer, editor, and real estate investor, Deidre Woollard of Millionacres. Here, Deidre reminds women investors of their great capacity to find success in the field, inspiring them to get out there and put themselves forward. She talks about investing according to the cycles of our lives, creating a diverse portfolio, real estate crowdfunding, Real Estate Investment Trusts (REITs) and more. Tune into this great episode to receive advice that is for women and given by women. Join Deidre and Moneeka as they provide other great insights unique for women in real estate.

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Increasing Diversity In Real Estate Investing With Deidre Woollard

Real Estate Investing For Women

I am delighted to welcome to the show, Deidre Woollard. She is a writer, editor and real estate investor. Her passion for real estate writing began when she created the first Estate of the Day column online and worked for AOL Real Estate. She later worked for and created the Ask A Realtor column. After that, she moved on to spend several years leading marketing departments at luxury brokerages across Los Angeles before co-founding a real estate public relations firm. She now works with the team at Millionacres, helping to provide education on a wide variety of real estate investing topics. Her passion is helping educate people on the ways that real estate helps build wealth. Deidre, welcome to the show.

Moneeka, thank you.

Before I bring Deidre on, ladies, I want to tell you a little story. David and I got married many years ago. In those early days, one of the things that we knew was that money was important in the world. We both came from families that had open conversations about investing, money and how money worked. We also both had ambitions beyond what we had learned from our family. My husband was working at a startup. We were not making very much money. We were broke. We bought our very first home for $10,000 from our wedding. We had so little money left. We had these dreams. We wanted to travel and see the world. We wanted to focus our lives on the fun of living rather than focusing so much on paying the dues when we were young so that we could live later.

We started to investigate what investing could look like even with us, where we had so little money. At least we had bought a house. Both of us knew that was a good idea, but we had so little money. We were paying a mortgage. We rented out a room in the house. We took that money. We wanted to invest it so that we could travel and we can build for our futures. Motley Fool book had come out the year before. We picked up two books. David and I read together every night. This is another one of those things we’ve been doing for many years before we were married. In those early years, we were reading financial books.

Motley Fool was the very first book that we read. It completely changed our perspective on life, money and the world. A few years later, we shut down our houses. David took a leave of absence from work. We put some backpacks on our backs and we traveled the world for six months. I tell people over and over again that it started because we got a good education. Real estate has been a big piece of that, but on the stock side, this was the big influencer. I got an email from Millionacres, which is the real estate division of Motley Fool. They said that they rated my blog as a top ten blog in real estate. I screamed, jumped up and down, I was clapping my hands. My husband was like, “What is going on?” I told him and both of us were so delighted. I immediately contacted them. That’s why we’re talking to Deidre. You have had such a huge impact on my life. Thank you.

One of the reasons Millionacres exists is because we wanted to take that same idea from the Motley Fool and how it helped people and bring that to real estate. There’s so much information out there, but it’s so confusing sometimes. It’s the same mission but translated into real estate.

That’s the gift. With the Motley Fool, they made it approachable, understandable and unscary. We could take some action. I know that’s where you’re headed with this too. It’s needed out there because it can be confusing.

Our goal is to make you smarter, happier and richer, which we all want to be smarter, happier and richer.

Any good investor knows that there's active and passive elements to all investments. Share on X

Tell us a little bit about how you developed a passion in real estate.

I started from the journalist side, from writing about it. Through writing about it, I started to meet many interesting real estate agents and brokers. This was one of the early days of blogging when there weren’t a lot of blogs. The real estate agents that were getting involved in technology started reaching out to me. It gave me this passion for understanding real estate as a profession and realizing how hard real estate agents work and understanding what the profession is like. I’m seeing the ways how especially women could become entrepreneurs through real estate. That was inspiring to me.

I loved many things about the conversations I’ve had back and forth with you and Sarah. Sarah was the person that reached out to me. When I was connecting with her about who I could bring onto the show to represent Millionacres, she started talking all about the statistics for women in real estate, which is relevant and important. It’s helpful for us women to understand that we’re under-represented, but it doesn’t mean that we don’t have this huge capacity.

One of the things that I’ve seen is that there are a lot of women who are in residential real estate as a career. There aren’t as many women who understand real estate investing or feel confident. One of the things that is true for a lot of women was a study by the Harvard Business Review that men will apply for a job when they’re 60% qualified. Women will not apply until they’re 100% qualified. Sometimes we as women have that little barrier where we feel like, “I’m not sure if I know enough. I’m not sure if I can handle the risk. I feel like I need to wait on the sidelines longer.” That happens both in real estate leadership and in real estate investing. One of my passions is encouraging people to get out there and to put yourself forward.

We’ve had a lot of real estate agents on the show that are women. They have excelled well. Investing is a completely different thing. For whatever reason, it seems like women are more willing to become an agent. They see their clients invest. A male agent will look at the property first to see if he wants it before he offers it to his clients. I’ve seen this out there because I was a mortgage broker. The women will offer to our clients first before she makes an offer, which is not always true. I don’t want to be over general. I saw it a lot. I was like, “Why is this happening?” I was the only female agent that was out there making offers on investment properties. It was interesting. Could you tell us a little bit more about the statistics?

What we did is we surveyed about 650 people and we got their opinions on real estate investing, both gender diversity and racial diversity, what people are seeing, and if they feel like the situations need to change.

What were your results? Tell us about that.

The first thing I found that’s interesting is there’s a little difference in how men and women invest. Our survey found that men are more likely to invest in REITs, Real Estate Investment Trusts, whereas women are more likely to invest in rental properties. That may be a comfort level thing. Sometimes I feel like women are encouraged more toward owning homes versus owning commercial real estate or owning real estate investment trusts. I’m not sure about you, but I feel like a lot of the stock advice sometimes can tend to feel a bit male skewed.

REW 25 | Diversity In Real Estate

Diversity In Real Estate: As an investor, you don’t necessarily need to be in the same types of investments at different portions of your life.


I was on a class and every single book that was recommended was by a man. They recommended ten books on the show. I thought, “There’s not a single book out there written by a woman that you value.” We see that in our industry a lot.

I see that on the commercial side and also the real estate investment trusts. Most of the books are written by men. I don’t think women understand that especially real estate investment trust or real estate crowdfunding are great passive investments. One of the things I feel is that there’s no such thing as active and passive being separate because they both require a certain level of active and passive. If you’re an active investor, you’re finding ways to automate or to use a property manager. I loved one of your podcasts with Kris Ward talking about how to use automation and things like that. That’s important. Any good investor knows that there are active and passive elements to all investments.

Tell me a little bit about what you perceive as the advantage for women in different investment strategies in real estate.

Some of it is the diversification and understanding what you need in particular time periods in your life. As an investor, you don’t necessarily need to be in the same types of investments at different portions of your life. If you have kids, you might not want to be dealing with individual rental properties when your kids are little or something like that. When you’re older, you may want REITs or something that’s providing you with a little dividend income. If you’re wanting to do short term rentals, let’s say you want to move somewhere else. You may have that short-term rental as that bridge property to get you there. I feel like investing is something that changes throughout your life. We all go through different seasons of our lives. A different type of it can help you with that different stage.

I love the way that you’re talking about the cycles of our life. It’s hitting home for me right now because I’m in a big transition. I started very young. We first bought our first home. There have been a lot of different strategies that we’ve used along the way both for stock and for real estate. For the most part, I’ve had everything in appreciation. I’m in California real estate, most of it is appreciation. We’re changing to cashflow and more passive strategies because David and I are looking at retiring in a couple of years. One of those things that we don’t talk a lot about in the show or anywhere is the cycles. One of the things that I feel that with men, it’s about the strategy and what’s going to make them money and what they’re excited to learn about. For women, we do need to focus a lot more on the cycles, what fits in, where and why and shift as the cycles do. Do you believe that’s true also?

Absolutely. That’s one of the reasons that we have many female writers on Millionacres. We’ve got women who are using different types of strategies throughout their lives. We’ve got one woman who’s investing in a lot of tax notes and she’s traveling the world right now. She and her husband were in Mexico. They own some properties, but they also invest in a variety of other things. It’s about what you want in your life and how real estate can help you no matter where you are and what you’re doing. There have been periods of time in my life when I’ve been more interested in owning property or periods of time in my life where I’m much more interested in something that doesn’t feel quite as labor intensive.

Tell us a little bit about what Mogul does.

Mogul is our premium service from Millionacres. It works like the Motley Fool. The Motley Fool has a free site and then there are premium services that do stock recommendations and things like that. Mogul is like that in that we do real estate recommendations for real estate investment trust and some real estate equities. We also do recommendations for individual real estate crowdfunded deals. Those are usually for accredited investors. You have to have a certain income to qualify for those. You’re investing a sum of money and it is held for a period of time to do something like redevelop an office building or build an apartment complex or something like that. At the end of that, you receive distributions throughout the course of the investment. You get your capital back plus the profits when the deal gets sold.

Diversification is the gift that takes a little bit of pressure off. Share on X

Mogul focuses on a lot of different strategies. Could you talk a little bit about some of the specific strategies that you like to recommend to ladies to create some diverse portfolio or how do you recommend that?

It depends on how much money you want to spend and what kinds of things you like to do. One of the reasons I like real estate crowdfunding, especially even with something like one of the smaller regulation A-deals where you don’t need to be qualified to be accredited investor. You can still invest a couple of thousand dollars in a REIT to develop certain types of properties. It’s exciting but also diversification is important. One of the things with rental properties or fix and flips is it can be a lot of pressure. Diversification, the gift of that to me is that it takes a little bit of that pressure off. It’s the same way with stock investing. I like to have my money in different sectors because different sectors perform differently at different times. We’ve been studying what’s happening with the COVID-19 pandemic in real estate. You can see that certain sectors are doing well and certain sectors aren’t doing well. Hotels, malls, and things like that aren’t doing well, but you’re watching warehouses, self-storage, data centers, those things are doing well.

Could you tell us a little bit more about how REITs work? I don’t think I’ve had somebody come onto the show and talk about that.

I love talking about REITs. They’re my favorite. REIT is Real Estate Investment Trust. Most of them are publicly traded. You could buy it like a stock, but it’s a little bit different than the stock because they have to pay out 90% of their income. They have to pay you dividends. One of the reasons people like them in retirement accounts is because you get dividends. Most of them are quarterly, but there are a couple of REITs that pay monthly dividends. You can hold them in a retirement account, which is nice because that way you’re not taxed on those dividends. You can hold them in a Roth IRA or something like that. That’s a great way to grow your retirement portfolio.

They have to pay 90% of their income. Why don’t you explain that?

It’s a little bit different than a stock because the REIT is holding real estate. You don’t look at the earnings per share as much. They move a little bit more slowly than stocks. Another piece of research we did was looking at how REITs versus stocks performed over time. We found that over twenty years, REITs will outperform the S&P 500. It hasn’t been true in 2019 where the S&P 500 has outperformed REITs. Especially in 2020 because tech stocks have been zooming including Zoom. Real estate has not been doing so well because of the pandemic and because of how many things were closed, which makes it a good time. A lot of those real estate investment trusts are undervalued for what they are.

Where would you look for those?

In Millionacres, we have a whole section on REITs. They’re part of the stock market. You can start looking at things like malls. Simon Property Group is the biggest mall REIT. There’s Empire State Realty Trust, which owns the Empire State Building. REITs underlie so much of the real estate in the United States. It’s fascinating. You can invest in warehouses. There’s a REIT called Prologis, which is the biggest warehouse REIT. Amazon is their huge customer.

REW 25 | Diversity In Real Estate

Diversity In Real Estate: Passive does not necessarily mean set-it-and-forget-it. You set it for a certain amount of time, and you revisit it because things change—the economy, your needs, the investment, and the way the market’s moving.


Would you go on Schwab, Fidelity, or whatever and look for REITs? Is that what you would put in there?

They’re like regular stocks.

I had no idea about that. I do this stuff. I didn’t even know about it. I knew about REITs, but I hadn’t done enough research to know very much about them. Do you talk about them on Millionacres?

A lot of our stories are on REITs. We do a lot of talking about this particular sector. That’s one of the things that even within REITs, which is a sector, there are different sectors. There are all those different categories and that’s one of the things that makes it exciting.

It’s so accessible and so easy. It is pretty passive. It’s as passive as you might say with stock. You need to do the initial research.

One of the people at Motley Fool got me into this idea of journaling my investments. Much of the stock market are emotional and you see the market go up and down, and it’s very easy to get caught up in that. When I’m thinking about a new investment, I write down why I want to invest in it, what I think about it. Quarterly, usually when the earnings come out, I love to listen to the earnings calls. I like to hear the voices and the people answering the questions. I go back to that journal entry and it’s like, “Did everything that I believed about that company three months ago still true? Do I still feel the same way? That’s a check-in. It’s passive but it’s not completely passive.

This is worth a deeper conversation. When we talk about passive, it does not necessarily mean, at least in my mind, a set it and forget it. You set it for a certain amount of time and you revisit it because things change. The economy changes. Your needs change. The investment changes. The way the market is moving changes, regardless of the economy. Different industries or investment types change. Things change. Set it and forget it means you’re not tinkering with it all the time, but you should have a period of time that you have set for yourself that you’re going to re-evaluate what you’ve invested in. For David and I, it is a quarterly thing. We do it like you do, Deidre. For my father-in-law, he does it once a year. For my dad, he does it once a month. It’s not like they’re constantly tinkering. It’s not like you’re buying, selling and paying commissions. They’re not doing all that stuff, but they’re re-evaluating their portfolio and their investments at a designated period of time. That is what I consider passive investing. You’re not just letting it go.

It helps take the emotion out of it. The thing that I see with the stock market especially right now is people get so wrapped up in, “I want to buy the bottom. I want to get in at the lowest rate. I want to sell it at the highest rate.” It’s a great idea in theory but it is not practical. What you want to do is spend most of your time. It’s like in real estate when people always say, “You make your money when you buy.” The same thing is true with a real estate investment, trust, or any stock. You spend the time on the research. If you trust the company. You look at the management. You trust everything that they’re doing. You see the vision. Those check-ins are just check-ins. They’re not panic moments. When the market is doing something weird and your stock went way down, you don’t panic because you’ve already made your decision. You trust that company. That’s important is to find those ways.

You don't time the market; you time your life. Share on X

I’m an emotional person. I want to find those ways to make myself feel confident. That’s one of the reasons that if I am feeling that way, I do make a note in the journal and talk about that, get it out of my head. I’m not thinking about what the stock market did yesterday and making myself nervous over it and trusting myself. I feel like that’s one of the ways you can learn to trust yourself more, which is important, especially for women in investing.

Much of the time I’ve said, I’ve been told and reminded by my husband, if it wasn’t a good investment when you got it, check that it’s still a good investment and you don’t lose money until you sell. If the market has done crazy things, just check in. Is this still a good investment? If you’re talking about REITs, do you still trust this company? Do you still trust this product? Do you still trust the team? Over time, it will recover. It’s the same with stocks and real estate. If you decide that something has changed in the foundation of that decision, now you can re-evaluate. You don’t lose money until you sell. That freak out mentality and everything’s gone down, let’s sell everything because I don’t want to lose any more money. That’s going to get you into trouble. The other thing that I learned because I was a heavy stock investor early on was this term in stock investing, “Don’t try to catch a falling knife.” Trying to catch the bottom, you’ll get bloody every single time. That’s a terrible analogy. It’s hard to catch the bottom. What you want to do is catch it when it makes good business sense.

A lot of people will get out and then try to get back in. That is a bad idea. Sometimes you have to ride out the bottom. Otherwise, you’re going to miss that return. You’re not going to catch the upswing essentially.

It’s too hard to time it.

It’s like in any type of real estate investing, if you’re buying and selling houses, a lot of people try to time the market. One of the things that I’ve always heard real estate agents say to their clients is you don’t time the market. You time your life.

Real estate is cyclical and it’s long-term. When does it fit into your life? Here’s one other thing around that, you time your life, but understand there’s never a right time. My husband and I were so broke when we bought our first place and we scraped up all our money. It wasn’t a good time for us to own. We wanted to travel the world. Our dreams were not about owning a home. However, we needed to make financial sense so it became a priority. We didn’t feel ready but we did it. I would tell them that all the time. It’s like having kids. Someone would want kids. They wanted kids. It was great. For most people, I know at least this was my experience, there was never a right time to have kids. You have to decide, “This is what I want and do it.” Whether it’s the right time or it doesn’t feel like the right time, if you feel ready or not.

Life will continue to happen. That’s one of the things people do. They try to line up, is this the right time? Sometimes you have to go with what your will is and then use your mind to supplement your will.

Could you tell us what we’re going to be talking about in EXTRA?

REW 25 | Diversity In Real Estate

Diversity In Real Estate: Our financial health is as important as our emotional, spiritual, and physical health. It is important to also give it the attention, respect, and love.


We’re going to talk a little bit about real estate crowdfunding. I touched a little bit on it, but we’re going to dive into it and explain what it is and whether or not it might be right for you.

We’ve had one guest come onto this show talking about crowdfunding. Many of you, ladies loved him. He did not pursue crowdfunding though. That was a report that I got back. I’m not sure whether it is because you weren’t interested or because it was confusing or whatever. I wanted to make sure that we gave you more information on that. When Deidre mentioned that, I thought it would be a great idea. That’s what we’re going to be talking about in EXTRA. Deidre, could you tell people how they can reach you?

They can go on to That is our main site. Our Instagram is @Millionacres. I’m on Twitter @Deidre and Facebook is @Millionacres. I’m out there.

I know that you have a free gift for my ladies. Could you tell us about that?

It’s a real estate investing eBook. It is essentially looking at all of the different ways that you can invest. It also touches on things that we don’t like to talk about like taxes, 1031 exchanges, and things like that. It’s a great basic overview and some of the best writing from a lot of our writers. I’m excited about that one.

Thank you so much for that. Are you ready for our three rapid fire questions?

Let’s do it.

Tell us one super tip on getting started investing in real estate.

Sometimes, you have to go with what your will is and then use your mind to supplement that. Share on X

I’ve talked about them so I’m going to have to say it’s REITs. You can buy a REIT for not a lot of money. You can spend a couple of hundred dollars and get a few shares of a REIT. That’s a great way to dip your toes into real estate, especially if you haven’t done that before. I would encourage people to look at REITs as a way to get started in real estate.

What is one strategy on being successful in real estate investing?

It is keeping track and finding a great way to have a spreadsheet or have a journal or have something that you’re checking in with yourself over time. Some people like to use Excel and pivot tables. Some people like to have an old school journal, but whatever you do, what you measure that’s what grows. Keep track and measure everything.

What would you say is one daily practice that you do that contributes to your personal success?

I would say it’s probably the Pomodoro technique, which is that idea of blocking off time. I liked that idea of blocking off time to do certain things. A lot of us get so distracted. If I’m going to be looking at an investment or reading an earnings report, I don’t want to have my Slack pinging me or something like that. I want to dive in. A lot of times, we’re natural multitaskers, especially for women. Finding places where you can focus on your investing in a deep and intense way is important. Our financial health is as important as our emotional health, spiritual health, physical health, and giving it that attention, respect and love is important.

Thank you for that. Deidre, is there anything else you’d like to say that we missed or a message you’d like to leave the ladies with?

The message is to educate yourself and understand that education can come from a variety of places and that there’s no one way to do things right. Experiment, read everything you can like books and blogs, listen to podcasts and then do it. You call that analysis paralysis. That can happen. That’s happened to me a lot. Just do it, spend a little bit of money, try something and see what happens.

Ladies, we have more coming. We’re going to be talking about crowdfunding. If you’re subscribed to EXTRA, please stay tuned. If not but you would like to subscribe to EXTRA, please go to You get the first seven days for free. You can get this episode. You can get a ton of other episodes and binge as much as you like. You can decide if you want to stay subscribed or not. For those of you who are leaving Deidre and I now, thank you so much for joining us. I look forward to seeing you next time. Until then, remember goals without action are just dreams. Get out there, take action and create the life your heart deeply desires. I’ll see you soon.


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About Deidre Woollard

REW 25 | Diversity In Real EstateDeidre Woollard is a writer and editor with two decades of experience covering all aspects of real estate from luxury residential real estate to the latest in proptech. She created the Ask A Realtor feature at and has led marketing and communications at top residential real estate brokerages.

Real estate investing is a family tradition; she comes from a long line of landlords, renovators, and contractors currently invested from Massachusetts to California. She has an MFA in Writing from Spalding University





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Moneeka Sawyer

Moneeka Sawyer is often described as one of the most blissful people you will ever meet.   She has been investing in Real Estate for over 20 years, so has been through all the different cycles of the market.  Still, she has turned $10,000 into over $5,000,000, working only 5-10 hours per MONTH with very little stress. While building her multi-million dollar business, she has traveled to over 55 countries, dances every single day, supports causes that are important to her, and spends lots of time with her husband of over 20 years. She is the international best-selling author of the multiple award-winning books "Choose Bliss: The Power and Practice of Joy and Contentment" and “Real Estate Investing for Women: Expert Conversations to Increase Wealth and Happiness the Blissful Way.” Moneeka has been featured on stages including Carnegie Hall and Nasdaq, radio, podcasts such as Achieve Your Goals with Hal Elrod,  and TV stations including ABC, CBS, FOX, and the CW, impacting over 150 million people.