118: Flipping Houses, Buying Apartments, and Selling as an Agent with Tyler Sheff

Tyler Sheff has seen a lot in his real estate career. He started flipping houses in his early twenties and was very successful before the housing crash. Tyler also held some properties as rentals and eventually sold his properties before the crash, which caused him to incur a huge tax bill. Tyler decided there had to be a better way to invest in real estate, so he started buying apartment buildings after the housing crash and held more of his properties instead of selling them.

Tyler eventually got his real estate license and started his own podcast that discusses real estate investing. On this episode of the InvestFourMore Real Estate Podcast, I talk with Tyler about his career and what he has learned over the years.

How did Tyler Sheff get started in real estate?

Tyler started investing in real estate during the housing boom. He was a house flipper but not in the sense that he would fix them up and sell right away. He would buy a house, rent it out for a year, and then sell the property after the market had caused values to increase. Tyler was lucky in that he ended up selling most of his properties before the housing crash. He was not lucky in that he failed to disclose all of his sales to the IRS and ended up with a huge tax bill. During the housing crash, he did a lot of traveling, started a trucking a business, and worked for the federal government doing oceanographic research. He loved the benefits of a government job but did not love paying the taxes that came with the income. He was trying to figure out how to pay less taxes when he discovered real estate agent. However, he knew flipping was not a great way to avoid taxes, so he focused on long-term rentals.

How did Tyler start to buy rentals and slowly get into real estate again full time?

While working for the federal government, Tyler accumulated 6 months of paid time off. He used that time to research single-family rentals and get his real estate license. Tyler bought some single-family houses, wholesaled some properties, and bought multifamily properties. He bought a four-unit multifamily property using his VA benefits, and he had to live in one of the units for a year. He has bought numerous single-family rentals but loves 10- to 20-unit apartment buildings.

Why does Tyler think being a real estate agent helps him as an investor?

Not only does Tyler use his real estate license to help with his own investing, but he also sells houses to make extra money. He specializes in high-end sales and loves the business. He wife is also a real estate agent and sells many houses each year. He thinks becoming a real estate agent is a great way to get into real estate full time. When you become immersed in real estate as an investor and agent, it makes both sides of the business much easier. Since Tyler is an agent, he has also networked with hundreds of people who have helped his business. In a world of shrinking real estate commissions, Tyler has no problem setting his properties apart from the competition by offering higher commissions to buyers agents. Tyler also sees no harm in being both an agent and investor. Many people are concerned about the implications of having a real estate license and buying off-market investment properties, but Tyler sees it as an advantage, and I do as well.

How can you get in touch with Tyler?

Tyler not only helps people buy houses as an agent, but he also helps investors buy multifamily investment properties. We talk about how difficult buying multifamily properties can be when you have never done it before, and Tyler will even become an equity partner on some deals. Tyler also has his own podcast, and you can find him at Cashflowguys.com.

Thank you for all your help with hurricane relief!

Texas was devastated by Hurricane Harvey, and now much of the Southeast and the Caribbean have been devastated by Irma. My wife and I honeymooned in Saint Martin, which is in complete chaos right now. I wrote an article a few weeks ago about how to help people in Texas.

I also ran a book sale over Labor Day Weekend to raise money for Texas. I donated all the profits from my book sales that weekend to East Texas Food Bank. The profit was around $800, but I rounded up to $1,000. I had already donated to the Houston Food Bank before that sale. The dumpster company we used sent a loan of supplies to the Houston Food Bank as well, which Nikki on my team helped fill up.

The sad thing was that when the company got to Houston, the food bank made them wait over 8 hours to drop off supplies, so they went to another town that seemed to need it more! That is why I wanted to donate a second time to the smaller towns who are not getting as much attention as Houston.