Before Damian Maldonado was negotiating billion-dollar valuations or building businesses across Puerto Rico, he was a kid living in poverty and sharing bunk beds in a homeless shelter with his brothers. But those early years didn’t break him. They led him to become the co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S. In this episode, Damian joins Ilana to share how growing up in poverty shaped his relationship with risk, money, and resilience, and what it really takes to bootstrap a company through market crashes, massive layoffs, and billion-dollar decisions.

Damian Maldonado is a serial entrepreneur, investor, and co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S., which he helped grow from a small startup into a national brand.

In this episode, Ilana and Damian will discuss:

(00:00) Introduction 

(02:57) Growing Up in Poverty and a Homeless Shelter

(08:42) Key Lessons from Early Jobs

(11:42) Pitching to a CEO at 21 Without Fear of Rejection

(14:38) Damian’s Journey into the Mortgage Industry

(19:14) Starting America Financing With No Safety Net

(22:30) Leading Through Layoffs and Downturns

(27:07) Why He Turned Down a Billion-Dollar Offer

(30:57) Leadership Lessons from Richard Branson

(34:25) Building a Portfolio Career with Adventure

(42:53) Q&A: Crafting a Response to ‘Tell Me About Yourself’

Damian Maldonado is the co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S., which he helped grow from a small startup into a national brand. He also co-founded American Home Agents and has expanded his business interests into hospitality and lifestyle ventures in Puerto Rico, including a boutique beachfront hotel, restaurant, and kiteboarding school, creating jobs and adding value to the local community.

Connect with Damian:

Damian’s Website: https://damianmaldonado.com 

Damian’s Instagram: instagram.com/damiankiteResources Mentioned:

American Financing Website: americanfinancing.net 

Numero Uno Website: numerounopr.com

Awaken the Giant Within by Tony Robbins: https://www.amazon.com/Awaken-Giant-Within-Immediate-Emotional/dp/0671791540

Think And Grow Rich by Napoleon Hill: https://www.amazon.com/Think-Grow-Rich-Landmark-Bestseller/dp/1585424331 

Rich Dad Poor Dad by Robert Kiyosaki: https://www.amazon.com/Rich-Dad-Poor-Teach-Middle/dp/1612681131/ 

The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Tim Ferriss: https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357