Get All Access for $5/mo

From Prison to Y Combinator Graduate to Megamillion-Dollar Business Andrew Medal chats with Frederick Hutson, the co-founder and CEO of Pigeonly. Hutson created a multimillion-dollar business after going to prison for five years.

By Andrew Medal Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.

Frederick is the CEO and founder of Pigeonly, a low-cost communication and financial services platform that makes it easy for people to support an incarcerated loved one. He came up with the idea after serving time in the federal penitentiary for distributing 3,000 kilograms of weed. Hutson leads a growing team of over 20 people from Pigeonly's Las Vegas headquarters and has raised over $5 million in funding from investors including Erik Moore (Base VC) and Mitch Kapor (Lotus).

Related: This Entrepreneur Was Down to His Last Cent When He Got an Order for His First Product. Now, His Company Is Worth More Than $28 Million.

Andrew Medal

Entrepreneur & Angel Investor

Andrew Medal is the founder of The Paper Chase, which is a bi-weekly newsletter. He is an entrepreneur and angel investor.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Side Hustle

The Side Hustle He Started in His College Apartment Turned Into a $70,000-a-Month Income Stream — Then Earned Nearly $2 Million Last Year

Kyle Morrand and his college roommates loved playing retro video games — and the pastime would help launch his career.

Business News

Homeowners in These 10 States Pay the Most in 'Hidden' Upkeep Costs

Hidden home costs pile on top of mortgage payments.

Growing a Business

5 Books to Help You Motivate, Unify and Build Perspective

In a post-Covid world, check out these must-read books to help build a more resilient organization, create a modern work culture and maintain a powerful growth mindset.

Money & Finance

Avoid These 10 Mistakes Entrepreneurs Make with Money

Despite the challenging statistic that only 5% of startups survive beyond five years, common financial pitfalls often contribute to their failure. Through personal observation, I've identified the prevalent financial mistakes made by entrepreneurs.

Growing a Business

How Visionary Leaders Transform Curiosity Into Groundbreaking Ideas

Lee Brian Schrager, founder of the South Beach Wine & Food Festival, discusses the spark that launched FoodieCon, his best practices for running popular food events, and why all business owners need to adapt to social media trends.

Making a Change

Learn All of Rosetta Stone's Languages for $152

A lifetime subscription is nearly $250 off for a limited time.