Leap Academy with Ilana Golan

From Homeless Shelter to Building a Billion-Dollar Mortgage Company | Damian Maldonado | E146

Leap Academy with Ilana Golan

Show Notes

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 res...

More from Leap Academy with Ilana Golan

Oct 13, 2026

Founders and executives: Stacy Brown-Philpot traces her path from Detroit to Google, TaskRabbit CEO, and a $172M debut venture fund. Stacy spent nearly a decade at Google, growing from a 14-person team to leading over 1,000 people in India. She later became CEO of TaskRabbit and sold it to IKEA after launching it into four new countries. To build Cherryrock Capital, she met 366 investors over two years and closed 83 of them, including Goldman Sachs, JP Morgan, and the Ford Foundation. Her c...

Oct 6, 2026

This episode is dedicated to food creators and entrepreneurs: how Carleigh Bodrug built PlantYou into a bestselling cookbook brand while privately grieving her mother's lung cancer death. Carleigh grew PlantYou to 13 million followers while filming recipe videos from chemo waiting rooms. She signed her second book deal two weeks before her mom's diagnosis and kept the ordeal off social media. Her debut cookbook sold out in two days and hit the New York Times list. She also covers the infogr...

Sep 29, 2026

We’re bringing back one of our favorite conversations from the Leap Academy podcast with Shopify President Harley Finkelstein. Harley Finkelstein didn’t set out to be an entrepreneur. He had no choice. With his father out of the picture, he had to pay for university and support his mother and sisters. So, he turned to his go-to problem-solving tool: entrepreneurship. Starting a t-shirt business changed his life, eventually leading him to Shopify, where he became one of their first merchants a...

Sep 22, 2026

We’re bringing back one of our favorite conversations from the Leap Academy podcast with digital marketing expert and entrepreneur Neil Patel.

Sep 15, 2026

Mike Fisher’s career has taken him from West Point and flying helicopters in the U.S. Army to leading technology teams at PayPal, serving as CTO of Etsy, and ultimately becoming CEO of MyFitnessPal.

See all episodes →