The Diary Of A CEOShawn Ryan: There's A Battle For Your Soul, It's Happening Right Now
The Diary Of A CEO
A Claimed Visit To Hell 0:00
Shawn Ryan opens by describing an experience he believes was a visit to hell, calling it more real than anything else he has lived through. He describes overwhelming fear and his body contorting in ways he says a human body should not move. He has since undergone several exorcisms, and he insists the things that have happened to him are undeniable, though he saves the full account for later in the conversation.
From Navy SEAL To Medellín 0:31
Shawn Ryan enlisted in the US Navy at seventeen and entered the SEAL program, serving five and a half years and deploying to Iraq, Haiti, and Afghanistan. After leaving the military he tried real estate, inspired by a Donald Trump book on getting rich, but failed. He then moved into government contracting, working for the State Department and later the CIA through Blackwater and a company called Socom before becoming a direct CIA contractor with no middleman. He later moved to Medellín, Colombia, which he calls the most dangerous thing he has done, becoming involved in mapping out drug dealing networks rather than dealing himself, drawn in by the rush, until a contact named Freddy told him police had planted a bug in the light fixture outside his door.
Inside SEAL Training And Combat 3:31
He explains that SEAL stands for sea, air, and land, describing it as one of the most prolific special operations units in the world, built on a training pipeline lasting a couple of years, including BUDS, jump school, and SEAL Qualification Training. He recounts seeing true poverty and chaos in Haiti in 2004 during the removal of President Aristide, with dead bodies in the water and prisoners who had broken loose. In Afghanistan he arrived after Operation Red Wings, the deadliest loss in SEAL Team history at the time, where a goat herder compromised a sniper team and a helicopter was shot down. He later left the SEALs because the deployment gave him less direct combat than he wanted, though his final mission involved training conventional units to hunt down bomb makers and insurgents.
Podcasting And Being Compromised 9:30
Shawn says he believes, without proof, that podcasters and influencers are sometimes compromised, pointing to how the Trump administration used podcasts heavily during the election cycle. He argues that guests and hosts photographed at events like the White House or holding up Epstein file binders become visibly tied to one team, losing their status as independent thinkers even if they still are one. He says he has turned down invitations to the White House and to ride on Air Force One because he recognizes them as attempts at capture. He also suspects some guests are planted, arriving with no real background yet gaining huge traction, sometimes seeded with a single clippable line, or making geopolitical predictions that later prove accurate in ways that feel engineered rather than coincidental.
Suspicious absence from popular lists 16:01
Shawn Ryan explains that despite getting 150 to 200 million views a month and sometimes beating Joe Rogan in US weekly views, his show never appears in YouTube's popular podcasts section. He traces this back to something he said early on about terrorism, and suspects a human element inside platforms like YouTube, Meta, and TikTok quietly shaping what gets promoted, describing it as cover work where someone's official job title hides a different real function. He brings up Annie Jacobson's term speculative narratives as a more accurate label than conspiracy theories for ideas like this.
Encounters with Trump and Harris 20:00
Shawn says he was supportive of Trump before the election but never issued a formal endorsement, and he also reached out to the Democratic party offering Kamala Harris a spot on his show with no preset topics, an offer her team ultimately declined after early talks. Trump, by contrast, came on with no guidelines at all. Harris did appear after the election, once she had lost and had little to lose, and Shawn describes her as unusually relaxed and honest, admitting Joe Biden had hurt her campaign, which he wishes had happened before the election for comparison. He says he has since changed his opinion of Trump, feeling his actions have not matched what he promised.
Iran, allies, and American decline 20:00
Shawn says he sees no positive outcome in Iran and that colleagues in the military feel the US is serving another country's interests there, likely Israel's, despite JD Vance calling America the senior partner. He doubts the stated nuclear justification for the conflict and worries America may be losing its superpower status, pointing to China going nuclear, unresolved power grid problems, and the weakening petrodollar. He criticizes Trump for punishing Canada with tariffs after it sought other buyers for pipeline oil that the US itself had rejected, comparing US behavior to dealing with someone erratic that no business could trust. He wants to produce a documentary style project visiting the poorest parts of all fifty states to confront politicians with the neglect happening at home while money goes abroad, and plans to explore what Britain's experience looked like when it lost superpower status to compare it to America's possible future. He also discusses a guest named Blair Skoro, a former CIA asset who infiltrated terrorist cells, whose sudden shift mid interview toward claims of Russian nukes entering the US struck Shawn as a possible inserted narrative.
Spotting a possible plant 32:01
Shawn describes challenging a guest on air, telling him he suspected a stray comment had been dropped in deliberately, as if the guest had been sent to insert that one line. The guest seemed taken aback, and Shawn says this is simply what it can look like when someone may still be working on behalf of an agency, even if he cannot say for certain whether that was the case.
Episodes he never aired 32:31
Shawn explains he rarely deletes episodes but has held a few back. One guest claimed the COVID vaccine was patented before COVID existed, but kept slipping and saying SARS vaccine instead of COVID-19 vaccine, which made Shawn doubt the claim enough not to release it, since he did not want millions of listeners making medical decisions based on something false. Another guest claimed expertise on the World Economic Forum but could not even explain what it was, so Shawn ended that interview. Most recently, a woman claiming to have worked for an intelligence agency fixated oddly on discussing polygraphs rather than anything substantive, which struck him as an attempt to sound legitimate, and that episode was also shelved.
Chasing adrenaline in Colombia 39:29
After his SEAL and CIA contracting years, Shawn spent two years in Medellin, Colombia, drinking heavily and getting drawn into drug networks, not for dealing itself but for the thrill of mapping out who controlled what. He says he had little regard for his own life at the time and figured if the excitement ever faded he would simply die there. He describes one reckless night at a bridge called Puente de los Locos, throwing cash into a crowd of homeless addicts and barely escaping as hundreds swarmed in.
The bugged apartment 41:58
After that bridge incident, a doorman named Freddy warned Shawn that police had photos of him throwing money and had asked about his identity, and that a bug had allegedly been planted near his door with surveillance set up across the street. Shawn cleaned out his apartment, ran a surveillance detection route through internet cafes to check if he was being followed, then left the country within twelve hours and never returned.
Slow road to changing course 46:30
Back in the United States, Shawn did not quit right away, continuing shorter trips to Panama, Costa Rica, and Honduras seeking the same adrenaline. A real turning point came when his best friend, battling a severe opiate addiction, left contracting, and helping him recover became Shawn's own purpose, pushing him to clean himself up and eventually start therapy, though his friend ultimately succumbed to the addiction years later.
A Breaking Point on Mother's Day 49:01
Shawn describes realizing his drug use had become life-threatening when things that used to feel fast started to feel slow, a warning sign a friend had once told him about. On Mother's Day, believing it might be his last day alive, he called his mother. That moment pushed him toward seeing a therapist, something he admits was a blow to his ego given the stigma around therapy, especially back then. With no friends nearby in Florida and nothing else to do, he gave it a try and found it genuinely helped, mostly because talking things through with someone neutral let him work out his own problems and gave him a form of accountability.
Two Ibogaine Journeys, Different Outcomes 51:00
Shawn explains his history with the psychedelic ibogaine, taken as a pill originally from a group in Gabon, Africa, which he calls the most powerful psychedelic available. His first experience, taken while struggling to be present with his wife and six-month-old son amid constant business thinking, was transformative. He came out with no desire to drink, quit sleeping medication, quit Adderall, and has now gone over four years without a drop of alcohol or any vices. He also describes using psilocybin and 5-MeO-DMT multiple times, saying these experiences gave him startling clarity on business decisions, relationships, and family matters, though he always treated them with caution and prayer, believing they opened access to a spiritual realm people aren't meant to reach.
Describing an Experience of Hell 57:00
His second ibogaine journey, about three months before this conversation, was different. During a five-MeO-DMT experience lasting roughly an hour and a half, he felt total emptiness, the most intense fear and anxiety of his life, and a sense of complete abandonment with no God and no Christ present, like an exorcism he couldn't stop. His body contorted in ways a friend who checked on him, a Marine Raider combat veteran, said he'd never seen a human body do. Since then Shawn says his life has turned dark, marked by nightmares, strange coincidences, and supernatural occurrences, including a dream that made him furious at Catholicism followed immediately by a picture frame flying off the wall during prayer, and an immediate allergic-seeming reaction moments after taking communion at mass. These events, he says, have drawn him deeper into his Catholic faith and closer to Christ.
Two sides of psychedelics 1:07:00
The guest says he has long supported the psychedelic community and the good it has done, but he insists there is another side people need to know about before making their own decisions. He is not certain his own troubles came from psychedelics, but that seemed to be the trigger point. He suggests psychedelics may open a forbidden realm, lifting a veil that perhaps exists for a reason.
Oppression versus possession 1:10:02
Asked to explain exorcism beyond the movie version, he says he has not had anything as extreme as a backwards spider crawl up a wall. He describes two categories, possession, where a person loses control of body and mind, and oppression, where troubling things happen around a person in areas like finances, health, family, or faith while the person stays in control. The priests who have worked with him believe his case is oppression, not possession, carried out through prayers in Latin and English meant to provoke reactions and narrow down what is happening.
Strain on family and faith 1:12:02
He describes coming home after his fifth exorcism and imagining what his wife and kids must think, wondering if he is still in control of his own mind. He says military figures, including SEALs and Delta operators, have privately told him they had similar experiences and called him brave for speaking out. The host shares his own path from a Christian upbringing through an atheist phase to his current agnostic but curious outlook, noting he was baptized on Easter 2024. The guest says these frightening events have actually strengthened his and his wife's faith.
A planned Bible series 1:18:02
He explains his decision to speak publicly, saying his huge platform and access to high-profile guests make it almost a responsibility to ask spiritual questions. Having grown disillusioned with political guests, he plans to spend several years covering every book of the Bible on his podcast, a project sparked by strange events the night before his interview with Cardinal Burke. He calls his current experience a real-time battle over his soul, requiring several daily prayers to release oppression, with no way to know how long it will last except that he will simply know when it ends.
Advertiser pulls out 1:21:02
He describes a long-standing advertiser, a life insurance company, canceling because it does not want to appear on faith-based content, even though its stated audience is people who care about protecting their families. He sees this as another sign of influence trying to stop him from discussing faith, tied to the broader battle he believes is underway, and says he cannot abandon the Bible series over lost revenue since he believes in heaven and hell and cannot take money with him.
Choosing Alignment Over Easy Wins 1:23:00
Steven points out a pattern among highly successful people: a moment when they chose against their short-term incentives. Jimmy Carr kept a good job but spent five or ten years doing unpaid comedy in pubs, and illusionist Derren Brown spent a decade doing card tricks in Bristol instead of easier work. In the moment these choices look foolish, but they consistently lead somewhere better. Shawn agrees, comparing it to choosing podcast guests. Booking a famous name might bring more subscribers short term, but it pulls him away from his own alignment, and living out of alignment leads to a life he would hate. He adds that it is easy to become part of the herd instead.
Why Shawn Keeps Doing This 1:24:31
Asked what drives him now, Shawn says he wants people to stop being afraid to ask questions and stop being so tribal. He keeps an open mind, talking to figures across the spectrum, from Brohan to Tucker Carlson, and he is willing to admit mistakes publicly, including times he unknowingly spread misinformation. He values courage and believes the country needs more of it, wanting to show that asking hard questions brings less backlash than people fear. On what a good life means, he points to creating memories with his wife and kids, insisting that money cannot buy peace or happiness, only remove some financial stress while adding new kinds. He describes himself as a workaholic who has learned to work smarter, sometimes turning down deals because they are not the right fit rather than bad ones.
The Cost of Building While Raising Kids 1:28:01
Shawn warns Steven that business can destroy a family, speaking from experience as someone who watches his son grow in fast, aching jumps. He describes the pull between urgent business calls and a two-year-old who just wants to play trains, admitting there is guilt in being close to his kids but not as close as he could be. Steven reflects on his own parents working constantly, framing that absence as a trade rather than a regret, since necessity shaped it rather than choice. Shawn's unresolved conclusion is to keep looking for power plays, only pursuing ventures he truly believes in, which led him to build Glacier, a phone privacy app offering secure DNS, a VPN, and burner numbers to block data brokers from harvesting personal information. He plans to eventually cut back to one podcast a week, valuing business as a creative outlet but insisting there is always another way to reach a goal. Asked what love is, he answers that it is what you are willing to die for, naming his family. Steven closes by praising Shawn's integrity and originality as a podcaster and a man.
Algorithm Picks Your Next Video 1:39:30
The closing moment points out that an AI-driven algorithm analyzes your viewing behavior to select a personalized next video, different for every viewer, and suggests checking it out.
AI-generated summary. It can be wrong or incomplete - check anything that matters against the original.
