Last fall, at the annual PopTech conference, I interviewed Lyn Ulbricht, mother of Silk Road founder Ross Ulbricht, and Leonard Pickard, who had been convicted in the largest LSD-production trial in history. A year ago, Ross—who was never actually charged with, much less convicted of, violent crimes—was pardoned by Donald Trump, and became a free man after serving over a decade in federal prison. Leonard, who had had served 20 years of a life sentence, was released in 2020 at age 75 as part of a COVID compassionate-release program. He and Ross became friendly after serving in the same maximum security federal prison.
Lyn Ulbricht, who I first interviewed for Reason in 2014, worked tirelessly and effectively for her son’s release. Since his pardon, she started the nonprofit Mothers Against Cruel Sentencing (MACS), to push for sentencing reform and to call attention to the conditions in prison. For a sense of how screwy things got regarding the persecution (that word is chosen carefully) of Ross, read about how the federal government gagged Reason, where I work, over our coverage of the trial and sentencing phase of Ulbricht’s legal case. Our full coverage of Ross is here.
Neither Lyn nor Leonard are prison abolitionists, but their calls for serious reform are deeply informed not just by their experiences but by a serious understanding of the function of prisons in society.
Here’s the writeup from PopTech’s website, followed by a link to the video at their YouTube page.
Moderated by journalist Nick Gillespie, this conversation brings together Leonard Pickard—once sentenced to two life terms for a nonviolent LSD case—and Lyn Ulbricht, whose son Ross received double life sentences for running the Silk Road marketplace. They share what it means to be told you will die in prison, the inner work required to hold onto hope, and the invisible sentences carried by families and children on the outside.
Pickard describes surviving 20 years in maximum-security prisons through meditation, legal persistence, and faith, then rebuilding a life as a biotech advisor and Harvard law affiliate after his sentence was commuted. Ulbricht recounts her 11½-year fight to free her son and her decision to found Mothers Against Cruel Sentencing to challenge extreme, often drug-related punishments that she sees as unconstitutional and inhumane. Together, they argue that most incarcerated people could safely return to society under supervised conditions, and they challenge us to treat our own freedom like a second life—to use our talents and power to build a more just justice system.
📍 Recorded Live at PopTech 2025: Enigma in Washington DC
A quick note about PopTech: Founded in 1996 by tech-sector titans Bob Metcalfe (he invented Ethernet) and John Scully (who ran Apple for a stint), PopTech embodied the techno-optimism during the rise of the internet as a ubiquitous feature in our lives. At the same time, PopTech also provided an informed and critical forum for discussion of what policies and practices might work best as the world became interconnected in a whole new way. It’s still going strong and will celebrate its 30th anniversary this fall in Washington, D.C. For more info, go here.
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