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.

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