“Pressure is a Privilege” – Carl Dumesle on Winning in Real Estate Artwork

Skip the Lines Podcast, with Jonathan Mitchell

I interview experts in their field.

Skip the Lines Podcast, with Jonathan Mitchell

“Pressure is a Privilege” – Carl Dumesle on Winning in Real Estate

October 07, 2025 • Jonathan Mitchell • Season 1 • Episode 70

What changes when you stop chasing units and start treating every building like a business that must truly perform?

San Diego developer and operator Carl Dumesle traces a wild path from Haiti to the Dominican Republic and then to the United States after surviving the 2010 earthquake. A Nestle rescue flight got his family out, and nearly a decade in the DR taught him languages and grit before an MBA brought him to San Diego.

Once here, Carl built a student housing startup, raised early capital, then clicked with partner Michael Crawford to create Building SD, while launching Parkside Asset Management to own the full life cycle from acquisition to build to operations to exit. He believes pressure is a privilege, controlling the controllables, and creating abundant neighborhoods where everyone winning lifts the comps for all.

If you are an investor, operator, or San Diego neighbor who cares about smart infill and performance, share this episode with a friend, tag someone who should hear it, and message us your biggest takeaways so we can feature you next time.

Chapters

00:00 Origin vibes, mantra, why pressure is a privilege

03:11 Haiti to DR to resilience

11:00 San Diego choice and the first partnerships

15:27 The Parkside model. Asset management as an operating system

26:32 Building in public. Abundance, comps, complete communities

35:15 Lightning round and the skip the line hack

Quotes:

“Pressure is a privilege.” – Carl Dumesle
“I like to control the controllables.” – Carl Dumesle
“We have about a dozen projects running at any given time.” – Carl Dumesle
“Ask a lot of good questions and you will skip all the lines.” – Carl Dumesle

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📢 Connect with Carl Dumesle!

Website: https://www.parksideam.com

Instagram: https://www.instagram.com/carldumesle

LinkedIn: https://www.linkedin.com/in/carldumesle

📢 Connect with me!

Instagram: https://www.instagram.com/jonathanmitchellre/

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Instagram: https://www.instagram.com/jonathanmitchellre/

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