From Prison to Silicon Valley: How One Entrepreneur Spun a Jail Sentence Into a Y-Combinator Backed Startup

For even the most well-connected first-time entrepreneur, pitching investors can be a rejection-filled exercise in angst. Now, swap the stereotypical Stanford education for a four-year stint in federal prison, and replace the quintessential Uber-of-X app built for professionals with a photo-sharing platform designed exclusively for inmates and their loved ones.

Talk about a barrier to entry.

It was fall of 2011, and this was exactly what Frederick Hutson was up against. The then 28-year-old had just been released from prison, where he had served 51 months for distributing marijuana via UPS and FedEx trucks from Mexico to Florida.

A natural-born entrepreneur, Hutson used his sentence to develop a business idea: For inmates, receiving photographs from loved ones is tricky because the pictures have to be physically mailed in (there is no Internet access in prison). Why not, he thought, create an online platform that allows friends and relatives to upload photos, which are then mailed directly to the inmate for a flat fee. That would make it far easier for loved ones to send in photos and, as he knew from personal experience, significantly improve inmates’ lives.

Upon his release, he needed to develop a prototype and convince venture capitalists to invest, no small feat for any untested entrepreneur, not to mention one whose business

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