The Cowboy Philosopher
This Hidden Brain episode profiles Riley Shepard, a small-time conman and musician who spent decades creating an ambitious Encyclopedia of Folk Music while deceiving investors and abandoning his family. The episode then transitions to a discussion with Harvard psychologist Leslie John about the psychology of secrets, exploring why people keep them, their costs, and when disclosure can be beneficial.
Summary
The episode opens with host Shankar Vedantam visiting the Library of Congress to examine an obscure archival collection belonging to Richard Riley Shepard, a musician and conman who died in 2009. Through interviews with his daughter Stasia, music researcher Kevin Coffey, and others, a complex portrait emerges of a man who was simultaneously a gifted hustler and a dedicated scholar.
Riley Shepard was born in 1918 in North Carolina, dropped out of school in fifth grade, and pursued a career in hillbilly and country music. He cultivated the persona of 'the cowboy philosopher,' signed with multiple record labels simultaneously using numerous pseudonyms, and was known for charm, deception, and an inability to honor commitments. He had children he never acknowledged, told women he was sterile, wrote pornography under fake names, and regularly fled towns ahead of creditors.
Despite all this, from 1960 onward, Riley devoted himself to creating an Encyclopedia of Folk Music — a hand-indexed, cross-referenced collection of over 43,000 folk song titles documenting 200 years of American musical history. Without a computer, he built an elaborate system largely stored in his own head. Folklorist Steve Winnick at the Library of Congress describes the work as potentially significant in the history of folk song scholarship, calling Riley a genius for the scale and ambition of the project. Riley sought publication and funding for decades, was rejected by publishers and the Library of Congress alike, and continued working on the encyclopedia until shortly before his death.
His daughter Stasia's relationship with her father was defined by the tension between loving a charming, creative man and recognizing him as a con artist who defrauded investors and abandoned his family. In his final days, Riley expressed regret, telling Stasia he was 'flashing back on all the things I did.' After his death, the encyclopedia — 40 boxes of material — was left to his friend Ted Enslin, and copies are now available through the Internet Archive.
The second half of the episode features Leslie John, a Harvard psychologist and author of 'Revealing: The Underrated Power of Oversharing.' She explores why people default to secrecy, the physical and mental health costs of keeping secrets, and how disclosure can build trust and intimacy. Listener stories illustrate various dimensions: a woman haunted for nine years by a trivial embarrassment, a transgender woman who hid her identity for decades, a man who concealed marital affairs, a German listener grappling with his grandfather's Nazi past, and an agnostic who hid his beliefs from his evangelical community. John argues that people systematically overestimate the risks of disclosure and underestimate the burden of secrecy, while also acknowledging that not all secrets are harmful — some, like shared surprises, can strengthen bonds and enhance intimacy.
Key Insights
- Folklorist Steve Winnick argued that Riley Shepard's Encyclopedia of Folk Music represented a potentially significant contribution to American folk song scholarship that almost no one in the field knows about, despite Riley having no formal education.
- Kevin Coffey, who interviewed Riley late in life, concluded that Riley's pattern of moving cities was not for artistic reasons but because he was 'getting out of town before he was being tarred and feathered' by creditors and deceived parties.
- Leslie John argues that when people face disclosure dilemmas, they naturally and almost exclusively focus on the risks of revealing, while rarely considering the risks of not revealing unless explicitly prompted to do so.
- Leslie John found that 80% of people lie to their doctors, illustrating that even relationships explicitly designed to promote wellbeing do not reliably produce honest disclosure.
- Leslie John's research found that people who keep secrets experience measurable negative outcomes including depression, anxiety, physiological stress markers, greater rumination, and poorer relationship quality.
- Leslie John describes the 'spotlight effect' — people drastically overestimate how much others notice and care about their actions — as a key reason why secrets feel far more significant to the keeper than to anyone else.
- Leslie John argues that the longer a secret is kept, the more it compounds and takes on a life of its own in the keeper's mind through rumination, while growing no larger in anyone else's awareness.
- Leslie John distinguishes between secrets kept for self-relief (to alleviate personal guilt) versus secrets kept for the other person's benefit, arguing that the former may actually impose a burden on the recipient rather than help them.
- Leslie John found in a nationally representative survey that approximately 49% of Americans reported having enjoyed keeping a secret, with pleasurable secrets typically involving shared understanding and mutual intimacy rather than concealment of wrongdoing.
- Leslie John's research with colleague Ryan Buell on an Australian credit card company found that voluntarily revealing the downsides of their products (anti-marketing) increased customer trust and extended customer lifetime rather than driving customers away.
- Stasia Shepard's account reveals that Riley's final days were marked by visible psychological torment — he told her he was 'flashing back on all the things I did' and pointed to his head saying 'you don't know what it's like in here,' suggesting late-life reckoning with a lifetime of deception.
- Leslie John argues that the most effective disclosers are those with the greatest 'disclosure flexibility' — the ability to move between complete openness in intimate relationships and complete guardedness in high-stakes professional contexts — rather than those who simply share more on average.
Topics
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