He Lost Everything. Then He Found a Way Forward.
Sometimes the most powerful thing a person can do is tell the truth about where they’ve been.
That’s exactly what our keynote speaker Jesse Crosson does — and he does it in a way that is honest, generous, and hard to forget.
Jesse will be joining us on May 28 at Giving Opportunity: Real Stories, Real Success, CFO’s first-ever gala event. We are honoured to have him with us.
A story that starts in the dark
Jesse grew up feeling like he didn’t belong. That feeling, he says, led him to make worse and worse choices — until, just after his eighteenth birthday, those choices led to arrest and a thirty-two-year prison sentence.
For most people, that would feel like the end of a story. For Jesse, it turned out to be the beginning of a different one.
Nineteen years, one decision at a time
During his time in prison, Jesse did something remarkable. Rather than keep running, he stopped. He faced what he had done and who he had become. Over the years that followed, he earned a bachelor’s degree in psychology, became a journeyman electrician, and actively mentored fellow inmates. Along the way, he helped lead a peer-support mental health program and continued to write.
In 2021, Virginia’s Governor granted Jesse a conditional pardon. He walked out and got to work.
Today, he reaches over a million people through social media, where he shares the unvarnished truth about incarceration, rehabilitation, and what real second chances look like. In addition to his advocacy, he founded the Second Chancer Foundation to support people transitioning out of incarceration — connecting them with mentors and opportunities to build new lives. He has also written a book: The Best Part of Prison: The Power of Second Chances and Reclaiming Life Out of Darkness.
Why his story matters to us
At CFO, we believe that recovery is possible. We believe that people are more than the hardest moment in their lives. And we believe that connection — real, honest human connection — is one of the most powerful forces for change that exists.
Jesse lives all of that out loud.
His story is not a fairy tale. He is clear about the harm he caused and equally clear about the long road it took to get here. As a result, what he offers is not a tidy inspirational message — it’s something richer and more real: evidence that change is possible, that people deserve support, and that what we do with our second chances matters.
That is the kind of story worth gathering for.
Join us on May 28
Giving Opportunity: Real Stories, Real Success is more than a gala. It is a celebration of the people and communities that believe in second chances — and a commitment to keep doing the work that makes them possible.
Jesse will be speaking and signing copies of his book at the event. We hope you’ll be there to hear him.
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