Armchair Expert with Dax Shepard

Episode: Michael Calvi (on being wrongfully imprisoned in Russia)
Release Date: June 18, 2025

Introduction

In this gripping episode of Armchair Expert with Dax Shepard, host Dax Shepard engages in a profound conversation with Michael Calvi, an accomplished investor and entrepreneur who experienced wrongful imprisonment in Russia. The discussion delves deep into Michael's extensive career in Russia, the circumstances leading to his incarceration, and the broader geopolitical implications of his ordeal.

Background and Early Career in Russia

Michael Calvi's Journey Begins

• Timestamp [03:01]: Michael shares his origins, being born in Milwaukee, Wisconsin, to parents from the Midwest, and moving to Oklahoma during his upbringing.
• Timestamp [04:20]: He graduated from the University of Oklahoma in 1989 with a degree in computer science and business, initially aspiring for a political career but pivoting to Wall Street after meeting a friend’s older brother working there.

Transition to Russia

• Timestamp [06:34]: In 1991, Michael inadvertently found himself in Russia when plans to join Salomon Brothers' London office changed abruptly. Instead, he was recruited by the European Bank for Reconstruction and Development (EBRD) to invest in the burgeoning Russian oil and gas sector.
• Timestamp [07:18]: Upon arriving in Moscow shortly after the fall of the Soviet Union, Michael witnessed the rapid dissolution of the USSR, a transformative period that set the stage for his future endeavors in Russia.

Life in Post-Soviet Russia

• Timestamp [09:07]: Michael recounts his initial fascination with Russia, describing the harsh climate, the challenging living conditions, and the surprising warmth and generosity of the Russian people beneath their stern exterior.
• Timestamp [12:00]: He details the economic chaos of the 1990s in Russia, highlighting rampant underemployment and the rise of opportunistic entrepreneurs who capitalized on the volatile market.

Building a Business Empire

Successful Investments

• Timestamp [18:36]: Michael discusses his significant investment in Yandex, often referred to as the "Google of Russia." His early faith in the company led to substantial returns, culminating in Yandex's public offering on Nasdaq with a $10 billion valuation.
• Timestamp [20:08]: Despite initial opposition from other investors, Michael's steadfast belief in Yandex's potential paid off, showcasing his strategic foresight in the tech sector.

Personal Life and Community

• Timestamp [22:28]: Michael introduces his wife, Julia, a Russian native, emphasizing the strong personal connections he formed in Russia. He shares heartwarming anecdotes, including an encounter with General Tom Stafford, symbolizing his deep integration into both the business and social fabric of Moscow.

The Downfall: Wrongful Imprisonment

Triggering the Conflict

• Timestamp [23:02]: Michael explains how a merger within a banking investment led to fraudulent activities by the other party, resulting in a series of manipulative tactics aimed at stripping control from his venture fund.
• Timestamp [24:02]: Despite his efforts to negotiate and maintain control, Michael faced aggressive threats and countermeasures, culminating in a sabotage event where his apartment was set on fire by suspicious contractors.

Arrest and Initial Imprisonment

• Timestamp [27:16]: On February 14, 2019, Michael was forcibly taken from his apartment by armed men, leading to a harrowing arrest experience. He describes the chaotic scene as multiple armed individuals stormed his home, marking the beginning of his wrongful imprisonment.
• Timestamp [37:04]: Michael details his first days in prison, the intimidation tactics employed by the interrogators, and the initial shock of being accused of fraud without substantial evidence.

Life in Prison

• Timestamp [38:07]: He paints a vivid picture of the prison conditions, likening the environment to "a 50-year-old prison" with pervasive smells and minimal facilities.
• Timestamp [42:26]: Michael shares his experiences in solitary confinement, the emotional toll it took, and the rare moments of camaraderie with fellow inmates, including a Deputy Minister of Culture and a Chechen general.

Legal Battle and House Arrest

• Timestamp [45:18]: Following months in prison, Michael faced a Kafkaesque trial devoid of proper judicial procedures. Despite a lack of credible evidence against him, the corruption within the Russian legal system made acquittal nearly impossible.
• Timestamp [49:17]: After two years under house arrest, Michael was eventually released due to high-level interventions, including attempts by U.S. political figures to secure his freedom.

Reflections and Insights

Betrayal and Disillusionment

• Timestamp [52:05]: Michael reflects on his deep sense of betrayal by Russia, a country he helped rebuild and believed in. The realization of systemic corruption and the ruthless control of the FSB shattered his trust.
• Timestamp [58:57]: He discusses overcoming cancer during his ordeal, which, combined with his imprisonment, led to a newfound appreciation for life and the importance of family and integrity.

Geopolitical Implications

• Timestamp [68:46]: Michael provides a nuanced analysis of Putin's motivations, linking them to historical grievances and perceived Western provocations. He emphasizes the complexity of the Russia-Ukraine conflict and the challenges in negotiating a lasting peace.
• Timestamp [75:20]: He breaks down the Russian populace's perspectives on Putin, categorizing them into opposition, passive support, and the majority who perceive life as inherently corrupt and are influenced by state-controlled media.

Future Outlook

• Timestamp [82:00]: Michael expresses confidence in Western institutions' resilience in contrast to Russia's totalitarian system. He underscores the importance of investing in businesses that empower individuals and foster transparency.

Notable Quotes

1. On Initial Imprisonment:

   • "And I know immediately that it's related to this case, but still, just, you know, adrenaline."
     — Michael Calvi [27:36]

2. On Friendship in Adversity:

   • "The best part of my book is the story of our camaraderie in that cell. These were not the hardened criminals or killers that I was expecting. They were really decent guys."
     — Michael Calvi [46:46]

3. On Betrayal:

   • "I felt betrayed by Russia. I had done so much to help this country. I believed in it."
     — Michael Calvi [52:05]

4. On Resilience and Integrity:

   • "If I get out of this, I have to give up all my money... But I have my dignity and my kids and my house on the inside."
     — Michael Calvi [58:57]

5. On the Nature of the Russian System:

   • "The FSB's control over life in Russia today is way deeper than it was at the time of the KGB because of technology, manipulate people's information and the degree of control they have inside all the big institutions of the country."
     — Michael Calvi [67:33]

6. On Moving Forward:

   • "I love that look you just gave him right now."
     — Dax Shepard [82:06]

Conclusion

Michael Calvi's harrowing experience as a wrongfully imprisoned American in Russia serves as a stark testament to the perils of doing business in a rapidly changing and often volatile geopolitical landscape. His story underscores the importance of resilience, the human spirit's capacity to endure unimaginable hardships, and the critical need for integrity in the face of systemic corruption. Through his narrative, listeners gain invaluable insights into the complexities of post-Soviet Russia, the ruthless nature of its legal and security institutions, and the profound personal cost of geopolitical conflicts.

For those intrigued by Michael Calvi's journey and the intricate dynamics of international business and politics, his book, Odyssey Moscow: One American's Journey from Russia Optimist to Prisoner of the State, provides an in-depth exploration of these themes.