Scaling into the Billions, with Chris Ressa

Our guest today is Chris Ressa, a retail investor whose, company DLC Management, operates and manages thousands of units of retail properties. In this episode, we talk about the future of retail, the crucial parts of a commercial real estate team, and the best ways to invest in different asset classes. If you’re planning to take the leap from residential to commercial real estate investing, this episode is for you! Learn more about Chris and his journey at!

“I like to solve challenges people think are unsolvable and do what is considered undoable.”


Chris’s company owns open-air shopping centers and strip malls with thousands of units of retail properties. In retail, leases are generally more complicated, long-term, and challenging.

In the commercial real estate industry, there are more legal decisions to make than in residential, but Chris encourages every business owner to make their own business decisions. The business decision-makers should be moving the strategy forward and the legal advisors should make sure that the business decisions are sound.

“I recommend business owners to hire W-2 employees when they’ve got the capital behind them to grow the business, or when it’s too hard to manage the third-party service providers because they’re too successful.”


Chris talks about some reasons to get into the commercial real estate space:

  • It’s an alternative investment, so you can diversify your portfolio.
  • Depending on the type of commercial real estate, the leases can be set up in a way that they are pure mailbox money for many years to come.
  • The return profile can be very good.

Chris is operating a large business with around 130 employees. According to him, the key to success is to have a great team. In the beginning, he doesn’t recommend hiring everyone as a W-2 employee, because it is much more sustainable to have third-party teams. 

When your business doesn’t just invest in – but owns real estate, that is when you should have W-2 employees who only work for you.

Chris recommends always having someone in your team who helps you identify opportunities and someone who helps you finance deals.

“Everyone shops online and no one shops at the store anymore. So the first thing is… that this is not true.”


Even though recently it is said that retail is struggling, Chris explains that it is not true. 85% of sales are still done in physical stores even during the pandemic. The cost of entry is way lower to start an online store, however, the stores that have a physical presence can scale better.

Groceries, material, and value items are expected to stay mostly in brick-and-mortar stores and not move to the online space any time soon.


At the end of the episode, Chris picks an action step from the REI Clarity Framework that is the most valuable for him. This is the “Build a Team”.

The number one thing he is doing every day when it comes to his team is connecting with them and making sure that he helps them grow their careers. He is trying to remove obstacles in their day job.

Mentioned in the show:

  2. His LinkedIn
  3. Retail Retold Podcast
  5. The REI Clarity Framework

Learn how to grow your portfolio and reach incredible success the right way! Visit us here for everything you need to know:

Special thanks to Chris Ressa for taking the time to share so many great insights with us

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Until the next time, We truly appreciate you listening.

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Show produced by Eni Horvath