I was a corporate marketing employee working for a global restaurant company, slowly climbing the organizational ladder at the pace of a crawl.
I wasn’t quite entry level anymore, but I was no where near living a life of financial abundance. In fact, I was living paycheck to paycheck and hoping the house I bought a year earlier wouldn’t present anymore maintenance surprises.
As the saying goes, those hopes turned out to truly not be a strategy, as life continued to happen with water leaks, bee-hive infestations, electrical nightmares and general repairs continually in demand. The unexpected continued to compound on top of my growing professional and financial discontent.
I had been out of college working in corporate marketing for a few years for a very successful company I admired. However, one day I looked up and realized through the culture of politicization of corporate America I began “tolerating” my life while waiting to be promoted to the next level. I looked around and recognized that most others had been programmed to do the same, and it became truly a way of life. After years with feeling like my life was in control of anyone but myself, one day I realized I had to snap out of it, immediately, and take charge of my future. Then my journey began.
That’s when I changed from being passive about my future, to actively taking steps to take control of my future.
It took me a while to realize the answers to my personal and professional dissatisfaction with my life were not going to be resolved by updating my resume and simply shifting to a new employer. I knew deep down, and with the help of seeking guidance from people I respected, that I needed to make a more profound transformation and take my future in a whole new direction. I decided after networking with many successful people, buying many lunches & coffees, attending seminars, and ruthlessly searching the internet for inspiration, to get my real estate sales associate license.
Upon becoming a licensed salesperson, I immersed myself in real estate and through my motivation and drive to take control of my future. In addition to this, I was lucky to have been recommended to hire a business coach, to help me collapse the timeframe of the success of my transition to employee to entrepreneur. I was able to double my income within 6 months by selling houses on nights and weekends.
I ultimately realized that residential real estate sales was not the path I wanted to continue down due to the constant time demands and highly emotional nature of the business. However, I reached an epiphany that my effort, creativity, and effectiveness as a person and professional would be endlessly rewarded in the world of entrepreneurship and real estate.
I had reached the first level of transformation through this awakening!
Then, with the help of a business coach, some authors he introduced me to such as Napoleon Hill, and some guy named Robert Kiyosaki, I learned about this whole new world of income producing investment real estate.
I learned how the rich think about money. My entire perspective changed. I learned to look at real estate as a vehicle, rather than just a place to live. As I delved into this rabbit hole of commercial real estate investing, I learned that my future depended on my constant and never ending evolution personally, too. I learned that anything that I wanted began in my mind, and if I followed the persistent path of the committed few, I could do be and have anything too.
I then began brokering commercial real estate, and lots of it. During this run up in the recovery from the financial crisis of 2008 and 2009, there were deals to be had and the market was on the rise. Through my efforts, I became known as “the apartment guy” and was selling multifamily real estate as much or more than any other investment salesperson in the market. Life was good and I had increased my income by over ten times!
Then, in October 2016, I officially invested in my first apartment deal, in an 8 unit multifamily property in Louisville, KY. I had officially taken my first step towards creating cash flow in my life that didn’t constantly demand my input or expertise, or so I thought. I wasn’t trading my time for money, finally! According to Rich Dad, all I had to do was buy a property and make sure the income outpaced the expenses and you’re all set. My real education in real estate had begun. I encountered drug dealers, frozen pipes, high vacancy, negative cash flow, and so much more in that first deal. Ultimately, this deal became a success, but these early challenges served me and forced me to significantly level up my game, not only so my next deal was better, but I could emotionally handle the challenges of being an entrepreneur and investor.
Fast forward, I’ve invested in tens of millions of dollars of real estate, and have been involved in hundreds of millions of dollars of real estate deals. Real estate has become a passion and I’ve learned firsthand the vehicle it can be towards designing a lifestyle, and I am passionate about sharing how others can use it as a tool for their own transformation too.
At age 30, I created and launched the podcast, Elevate, which is all about mindset, mind expansion and personal growth for high performing real estate investors. The separator for me has been constant and never ending personal improvement, and sharing this learning on a public stage through the podcast keeps me sharp, helps me connect to contribution to others, and develop a dynamic and fun network of remarkable people. We’ve been blessed to reach the top 200 business podcast charts globally and guests include globally known thought leaders in personal development, neuroscientists, prolific entrepreneurs, professional athletes, psychologists, economists, pulitzer price winners, #1 New York Times Best Selling Authors, incredibly successful real estate investors and much more.
My wife, Katie, and I live with our twins in Louisville, KY, along with our dog and cat. We frequently travel internationally and are committed to continuous expansion in our life and are passionate about sharing the lifestyle of abundance with others.
More About Tyler
Tyler Chesser, CCIM is a high performance real estate entrepreneur who helps real estate investors and entrepreneurs transform their finances, businesses and lives. A successful real estate investor with a background as a former perennial top performing commercial real estate broker, Tyler started investing in multifamily real estate in 2015 as a way to build wealth and create diverse income streams for his family.
Prior to the 2020 co-founding of the real estate investment firm, CF Capital, Tyler spent over seven years in the business as the founding principal of a successful commercial brokerage company, a real estate investor, keynote speaker and award-winning sales professional after his withdrawal from corporate America in the early 2010's. Today Tyler adds value to others in a range of capacities – from syndication of private placement real estate investments, individual to group business coaching, real estate consulting, keynote speaking and also hosts a top 200 business podcast internationally called Elevate Podcast.
The podcast is well known for the high-level mindset, mind expansion and personal development content which decodes the stories, habits and multifaceted expertise of world-class investors and other experts; to the core this platform propels Tyler's constant and never-ending commitment to improvement. His core belief is that human beings were designed to go big, which is apparent in all that he does.