top of page
  • Writer's pictureJohn Casmon

From Flips to Small Multifamily Cashflow with Tyler Sheff, Episode 27

After a career as a police officer, Tyler Sheff began flipping houses with tremendous success. However, he did not anticipate the crushing tax bill, which forced him to rethink his strategy. Now Tyler invests in small multifamily properties for cash flow in both Tampa, Florida and Memphis, Tennessee. He is a licensed real estate agent, problem solver, educator, investor, syndicator and the founder of On today’s show, he talks about his strategies, how he invests from afar in Memphis and why Tampa is so hot that buyers are getting into fistfights over properties.

Key Market Insights

  • A former police officer, Tyler got his real estate license in 2000 and began fixing and flipping

  • Noticed values in single family were going up 25% per year and started renting his flips to take advantage of the appreciation

  • Sold them all in 2005 for top dollar, but did not report the sales on all of his properties and was threatened with interest and tax bill from the IRS

  • Burned himself out flipping houses and got a job with the federal government

  • List of limiting beliefs held him back from buying multifamily properties

  • Purchased a 4-plex and then learned how to raise capital from being involved in mastermind groups

  • Focus markets are Memphis, TN and Tampa, FL

  • When working with buyers, he prefers to take an equity position on deals in lieu of a commission

  • Partnered with a brokerage that has been around since 1942

  • Memphis varies wildly from street to street, like to be around the north part of Memphis near the university

  • Need to be direct to the seller when purchasing property

  • Tampa you get some appreciation, Memphis is strictly cashflow

  • People are getting into fist fight over Tampa real estate

  • Minimal multifamily properties in Tampa, while Memphis has a plethora of multifamily

  • Small multifamily are often grossly overpriced or underpriced on the MLS

  • Launching a mastermind in 2018 and teaching a class on non-performing notes

Bull’s Eye Tips:

Winning Your Market: Memphis: Find good management first, Tampa: focus on MLS for small multifamily

Tracking Market Changes: Networking at REIA, connect with team, subscribe to digital newspapers

Daily Habit: Read 60 minutes of self improvement


Best Business Books:

Creature for Jekyll Island by G Edward Griffin

Digital Resources

Tweet This: "I’d rather take $100 monthly than $1,000 one time"

"People are getting into fist fights over properties in Tampa, everyday is Black Friday"

"Flipping houses doesn't build wealth, it pays the IRS"

"A (projected) return is fine, if everything works out"

Places to Grab a Bite:

Connect with Tyler:

Leave us a review and rating on iTunes or Stitcher. Be sure to check out more info at

bottom of page