Investors Like Me: Deidre Woollard

Deidre Woollard is a writer and editor focused on real estate investing. 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 realtor.com and created the Ask a Realtor column. After that, she spent several years leading marketing departments at luxury brokerages across Los Angeles before co-founding a real estate public relations firm. She has been at The Motley Fool for several years and focuses on providing education on a wide variety of real estate and investing topics.

When I was 12, my father gave me $100 to invest in a stock. I had no idea what to choose and came up with a few options, including Disney and Exxon (now ExxonMobil) because I liked the tiger mascot. My father vetoed me on Disney, so I went with Exxon. I held that stock until college when I -- like so many young adults -- made some dumb decisions with money and had to sell it to get myself out. The ability to pay off debt with a stock made me eager to start investing once I could save a little money.

I had one parent who was extremely frugal and one who was a spender. My parents were divorced, so I shuttled between these two very different relationships with money. I took on characteristics of both and ended up going to college with a fair amount of savings that I went through pretty quickly, but it taught me a valuable lesson about emergency funds.

My father died when I was in my 20s and left me with a small stock portfolio. I understood next to nothing about stocks, and that's when I discovered The Motley Fool. This is back when most people knew of stocks only as strings of tickers printed in the newspaper. I started making notes about each company, following each ticker, reading the annual reports, and understanding more about how investing worked. It really interested me, but because I had grown up being told I was "bad at math," I didn't feel like I could be an investor. It took a while for me to comprehend that my ability to understand a story, history, and marketing was a real advantage as an investor.

One thing I've learned the more I've studied housing issues is that we often carry shame about things we have no control over. We blame ourselves for what we don't know. Women didn't even have equal access to credit until the 1970s. We are entering a time when more women are graduating from college, becoming solo homeowners, and taking control of their money than ever before.

It gets better. Then worse again. Then better. The first time I saw the stock market have a really bad day, I thought it would never recover. The Dow went down 87 points, and it felt like the end of the world to me. Now that type of drop is like a sneeze. It's hard to trust what you haven't experienced, but let history give you some comfort.

I would have understood the value of small bets earlier on. I tended to see risk as a single thing -- you either are or are not a risk taker. Now I know you can be risk-fluid and have both steady stocks and riskier bets in your portfolio.

Watching the democratization of financial markets and how much information has become available has been fascinating.

We are just at the beginning of sustainability reporting, and it's really heartening to see how quickly that is evolving.

I've been following crowdfunding in real estate and other areas and feel it has the potential to be another way to receive a positive return on your investment.

For every good idea, there's a way to use it irresponsibly. We've seen this over and over, with stocks, with crypto, with crowdfunding -- I hate how the hype cycle always ends up hurting the little guy.

I worry that the average hold time of stocks has decreased (currently around 10 months), which will impact returns for people.

I feel housing is still a stacked deck, and I'm scared that some of the past injustices will never be righted, meaning the opportunity to own a home and use the equity as a store of wealth won't be accessible for many people.

I'm a big fan of Sallie Krawcheck and her work with Ellevest. I also love seeing powerful female CEOs like Roz Brewer of Walgreens and Carol Tome over at UPS. I recently read a book about Mary Barra of GM, and something I respect most about her is her ability to make the hard and unpopular calls when the situation warrants.

I love seeing young Instagram influencers like Haley Sacks of Finance is Cool/Mrs Dow Jones. I'm a macroeconomic nerd, so I like things like the Moody's Talks podcast from Moody's Analytics and Behind the Market hosted by Jeremy Schwartz. The TreppWire Podcast is a great source of information on what's happening in the commercial real estate sector.

"Comparisons are odious."

I think one of the core sources of unhappiness is comparing ourselves to others, and often, we use money as that metric. We don't invest to keep score; we invest to provide for ourselves and our families and to fund the things that matter. Treating it like a video game where you are trying to amass the highest score is missing the point.