From NY Real Estate to Regenerative Living — with Matthew Blesso

Matthew’s Story:

In this episode of Business Love Stories, I sit down with serial entrepreneur Matthew Blesso, founder of Blesso Properties, Shift Esperanza, and multiple ventures in hospitality and real estate.

 

From buying his first apartment in New York to designing a Manhattan penthouse that made the New York Times front page, Matthew’s career looked like a textbook success story.

 

But after years of building bigger and more ambitious projects, he realised success alone wasn’t enough.

 

That insight set him on a journey of self-love, purpose, and eventually to leading Shift Esperanza, a regenerative living community in Costa Rica where real estate development is about healing people, land, and local communities.

 

In This Episode, You Will Learn:

• Why big goals don’t always lead to lasting fulfilment — and what does.

• How to spot when ambition is helping you vs. when it’s harming you.

• Simple practices to grow genuine self-love and resilience.

• How to align both joy in your work and a deeper purpose.

• What it takes to build businesses and communities that give back more than they take.

 

Connect with Matthew:

ShiftEsperanza.com

Instagram: @shiftesperanza