Think Realty shines a light on some of the many women who are making waves in the real estate investing industry.

Real estate investor Jamie Wooley has always been an entrepreneur at heart, having a few businesses when she was in her early twenties. But those businesses didn’t lend to her financial goals, and they also didn’t fuel her passion. So, she took a step back to reassess and reevaluate a plan.

“I took a year off to work for my dad as an office assistant. I thought it would give me time to decide my next move. That one year turned into eight and I woke up one day asking myself how did this even happen? The next day I gave notice and earned my real estate license to learn how to flip houses. My husband and I did our first flip in 2005, and I enjoyed every moment of the process. I decided to go all in on being a flipper but at that time, I didn’t think of it as a business. I soon realized it’s not easy to find homes in need of repair to fix up on the market,” she said.

Wooley set out to understand the industry and eventually flipped, wholesaled, or rented over 350 properties.

What is a trait you exhibit that has held you back, and did you change from recognizing it?

I have been a people pleaser my entire life, which I’m still working on. When I grew my team, I wanted everyone to love their jobs and expected them to put the effort in that I have for previous companies. This unfortunately is just not the case. I learned how to set clear expectations from day one, so it is clear on paper what the consequences are. I was able to learn how to take feelings out of it.   

When things get tough, how do you get going?  

I believe your “why” must outweigh the toughness knocking at your door. First, get very honest with yourself and determine your “why.” For motivation, go on YouTube, find a video that relates and crank it up. Sometimes I turn off all communication, dive into a movie and just rest my brain for a few hours. I also think about my daughter and what I would say to her in a tough moment then relay that to myself. I think we get stuck in tough times, but if you can mentally pull out and be the person on the other end giving advice, it becomes more manageable.

What is something you plan to do differently with your real estate investing business in 2020 that you haven’t done before? 

I have been so fortunate to learn from some of the best in the business. There are so many ways to achieve your goals in real estate and I chose wholesaling/flipping. I will continue to do that but on a much smaller scale while working towards my end goal of leaving a legacy. I am in the process of developing land to build homes and rent out. I am learning everyday how to work smarter and not harder, which does exist.

Best advice for new investors?  

Don’t give up. But, you must really want it. There is so much opportunity in real estate but don’t just follow the trends; decide what you want, what skills you bring to the table, and create the action plan. You must have a “why,” you must have a “goal,” and you must have a “plan.” Without these three things you might as well be roaming around lost in the woods.

Best advice for seasoned investors?  

Give back when you can. Your successes can give others the fire and mindset to go out and conquer any goal. Your failures can teach so much and allow another lens to look through. If you are a seasoned investor just know someone’s life can change from something as small as a post on social media, a phone call to give encouragement, or even a warning that helps someone from falling hard.

Why is the real estate industry good for women? 

There is nothing more genuine than to truly care, treat people with respect, and help others. We have an innate ability to do this and in turn it helps build genuine relationships that are much needed in the real
estate industry. 

What three strategies or tools have helped you the most?

  1. Masterminds have had such a large impact on my life that my partner and I started Next Level Flipping, which is an online mastermind for experienced investors.
  2. If something is trending, pay close attention as it may be time to go down a different path.
  3. The business tool, Asana, helps my team stay organized and I love it!

Connect with Jamie:





Instagram: Jamie.Wooley

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    We believe in the positive, life-changing impact of real estate investing. Our mission is to help investors achieve their goals to build wealth, better manage time, and live a life full of purpose.

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