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  • Chris & John

Ep 29: Finding the Missing Pieces with Sterling Chapman

One of the joys of real estate is that it is based on a few very graspable concepts, but presents so many avenues and ways to cut deals once they have been learned. Sometimes all it comes down to is identifying the right group of partners who each bring something to the table that the other desires. Today’s guest is Sterling Chapman, and after a few years of climbing the corporate ladder, he joins us on the show to talk about the deals he has breezed through since developing a taste for real estate. Sterling went from being a financial advisor to the regional sales manager at AT&T and got an MBA along the way too. After transitioning to telecom and achieving relative success at his firm, he started having desires for projects that were more entrepreneurial.

Real estate seemed like a good fit and during the interview, Sterling talks about his great first year and a half in the game. Initially, he read a few key texts like Rich Dad Poor Dad and then jumped straight into buying his first few single-family homes. Not long after, he began to scale up into duplexes and fourplexes too. Sterling has made some smart moves so far in his journey. He tells us the story about an amazingly successful deal he cut on a duplex between himself, his brother, and a friend who flips properties that turned out to be a major win-win for everybody involved. This episode packs some great pointers for those of you who are just getting into the game, and the seasoned pros out there should be able to pick up a few tidbits too.

Key Points From This Episode:

  • How Sterling got into real estate as a buffer against the corporate faucet running dry.

  • Ways our guest educated himself: reading Rich Dad Poor Dad and content on BiggerPockets.

  • The first single-family homes and duplexes Sterling bought on his journey in real estate.

  • A steep incline of deals Sterling got into involving fourplexes and basic syndication.

  • Scaling up and states other than Louisiana that Sterling is looking for bigger properties in.

  • Sterling: an example of somebody who didn’t use his W-2 as an excuse not to do real estate.

  • Debt to income ratio and how many of Sterling’s doors are seller-financed: 14.

  • Loan types and why Sterling prefers lenders he knows than ones with the ‘best rates’.

  • How banks often misinform loan shoppers that loans they can’t make don’t exist.

  • Trends Sterling is considering before purchasing properties in other states: rent rates, etc.

  • Lessons learned on previous projects and how Sterling feels confident going into syndication.

  • How Sterling’s sales career and his aim to vet a partner will aid him in future syndications.

  • Why scale up? You will be able to afford a property management company.

  • Nightmare stories of mom-and-pop property management companies mismanaging units.

  • Why Sterling won’t start a property management business despite having no competition.

  • A smart way to get into property management: employ a family member.

  • What Baton Rouge can provide as far as cash flow where it lacks in appreciation value.

  • The finer details of Sterling’s amazing duplex deal involving his brother and a friend.

  • How Sterling’s brother wanted equity on the next deal after his debt went well on the first.

  • What newbies can learn from the mutually beneficial duplex deal Sterling cut with a flipper.


“Another topic on lender shopping is – when you go into banks, if they don’t do it, they’ll tell you nobody does it.” — Sterling Chapman [0:16:43]

“I didn’t sleep at night for the three months it took to fix up those duplexes and refinance them.” — Sterling Chapman [0:22:08]

Links Mentioned in Today’s Episode:

Sterling Chapman

Sterling Chapman on LinkedIn

Crestworth Capital


Rich Dad Poor Dad

Best Ever Apartment Syndication Book

The Rent Roll Radio Show


Chris Grenzig on LinkedIn

Chris Grenzig on Twitter

John Cohen on LinkedIn

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