I’d love to hear how you got where you are today!

[Ashley Turner]

I'm new to this site and loving it so far, great for information and I've learned so much! My dream has always been to be in real estate, and to eventually own multiple LTR & STR. With that being said, there seems to be a ton of intelligent and successful people on here, and I'd love to hear your stories on how you started, how you got where you are today. Your struggles, mistakes, your successes, & any tips or advice in what direction to go in, and how to get started. You can comment on here or send me a private message if you'd like!!

Im Ashley, I’m 28 years old. I’ve lived in the Cleveland area my whole life. I grew up with a single mom very low class and started supporting myself at a young age. I am the first person in my family to ever own a home. That being said, I never really had any help or guidance and have had to learn everything I have in life on my own. So I love to talk to people that are doing well; and are successful in life, so I can brainstorm, learn, and figure out what I can do to be successful. 

[Travis Timmons]

Slowly, steadily, and frustratingly. I started my first business - non RE, traditional business brokering freight -  at 23. It failed, so naturally, I decided to start the same business over again. I took on an investor partner this time because it would be more stable. It wasn't. He was kind of slime ball that stopped paying our vendors and still owes me a small pile of money that I'll never get back. For those keeping count, attempt 2 - also failed. 

Throughout all of this, I was essentially living off of waiting tables and bartending on nights and weekends. I went through a stretch at one point where I went something like 150 days straight without a day off (either working selling freight or at the restaurant - usually both). It was frickin' exhausting. I was just dumb and stubborn enough to keep at it. If I'm honest, the goal that I had was worth the sacrifice. That's why I kept at it. This was after doing the same thing on my first business - living in my uncle's basement, selling during the day, waiting tables at night, only to see those efforts end in failure. It happened again. Different set of circumstances, but the same end result. 27 or 28 at this point. Failed entrepreneur and waiter/bartender. All of my college buddies had good jobs, were buying their first home, on the right track. I was still right where I started with a negative net worth and a hopeful but discouraged spirit. I was newly married and kind of felt like a loser. 

Naturally, I decided to start the same business for the 3rd time. I was able to parlay what was left of my previous business into an agency agreement with a competitor where I convinced some of my customers to come with me. That ended up being about $800/month in income to start; not what I was expecting but better than nothing. A few years later, after growing it, they bought out my book of business, and I could finally exhale financially. I got a good W2 job for 3 years while I waited out a non compete. I then bought a small book of business in 2017 and started slinging freight once again. I've grown that business substantially and am once again being bought out - with a close date in January. 

In the middle of that, we (me, wife, and 2 young daughters) got tired of hot summers in Houston and purchased a vacation property of sorts in Oregon. We planned to spend summers there and would attempt to rent it out when we were not using it. That's how we became accidental landlords and caught the RE bug. We (my wife and I) have since purchased 2 properties in Maine (short term rentals) and expect to scale up more next year after I sell my business. I'll still do some contract work and dabble a bit - things like substitute teaching in my kids school or start a business (to be determined) with my kids - ages 7 and 9, but I see a realistic path to living full time of off dividend, investment, interest, and real estate income next year. 

My advice to those starting out, which is obviously biased by my own experience, is to establish success and economic security outside of your real estate investments. It's exponentially easier to do this when you have a good income (along with a good savings rate and low cost lifestyle). Real estate is so much better when you don't need the income and can let the snowball start to roll downhill. Get to the point where houses buy you houses. Most things worth doing are likely going to be more difficult and take longer than you expect. If you think about a goal or the life you want everyday, don't give up on it. Persistent, focused effort over the long term is close to undefeated. Slow and steady still wins the race.