“One of the deals I learned the most from was also one of my biggest losses,” Jamie Wooley admitted ruefully. “It was a historic renovation (images top and below), so we took a 700-square-foot property and added 2,000 square feet. It’s one of my favorite transformations, but it was also one of my biggest losses. That hurts, too, because it was 100-percent my fault. I learned a lot.”

Here are four things Wooley hopes new investors can learn from her, so they do not have to learn these hard lessons firsthand:

1. You can’t do real estate on a handshake, especially not with someone you don’t know.

“That huge loss was a direct result of my choosing the wrong contractor, not setting out a scope of work, and agreeing to the relationship with just a handshake. You want to just be honest and shake hands, but that is not realistic with strangers in real estate. It’s not good for anyone.”


2. Find the resources to get a mentor, a coach, or educational training.

“It used to be that you could not have a real estate investing coach unless you had the resources to pay pretty big money for a personal mentor or program. Today, there is so much information online, for free, that you can start there. I still think if you have the financial ability to do so, you should pay a coach or mentor, but if you don’t, then identify someone in your local area doing what you want to do and ask them if you can help out with their business in exchange for advice and experience.”

Read more about Jamie’s investing background an success here.

3. Stay with your strategy of choice for at least six months.

“Every market is competitive right now, but I think the real reason a lot of investors do not make it in real estate is because they run around chasing four or five different things. They go to a meetup and they hear terms like owner-financed, subject-to, flip, wholesale, and they do not focus on one thing. Without an action plan and sustained focus, you won’t be successful. Once you experience that first success and master that first strategy, then you can start adding things to it.”

4. Fear and failure can be beautiful.

“The mindset and experience you gain from failure are rewards in themselves. Learn to love failure and fear, then learn from failure and fear. You must never let fear of failure alter the goals you set out to achieve!”

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  • Carole VanSickle Ellis

    Carole VanSickle Ellis serves as the news editor and COO of Self-Directed Investor (SDI) Society, a membership organization dedicated to the needs of self-directed investors interested in alternative investment vehicles, including real estate. Learn more at SelfDirected.org or reach Carole directly by emailing Carole@selfdirected.org.

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