Don’t Do That: Don't Ignore Your Instincts with Jack Devine, The Arkin Group (Ep.35)
Summary:
In this powerful and wildly insightful episode, Kelly Waltrich sits down with Jack Devine, former CIA spymaster, intelligence expert, and the man who helped shape some of the most pivotal moments in modern geopolitical history. Jack opens up about the guardrails of intelligence work, the chaos of today’s global landscape, how wealth managers can navigate uncertainty, and why, despite everything, he believes we are heading toward a more stable world.
He also shares stories from the field, what Hollywood gets wrong, what it gets surprisingly right, and the one operation he’s most proud of (hint: it changed the direction of the Cold War). And yes… we even find out how he feels about Jack Bauer.
Kelly and Jack cover:
00:00 – Opening: The chaotic state of the world and the speed of modern information
00:31 – Introduction to Jack Devine: Former CIA Director of Operations and his new intelligence platform for wealth managers
02:13 – Jack’s career highlights: Chile, Iran Contra, Afghanistan, and the Stinger missile that helped end the Cold War
04:48 – The surprising connection between intelligence work and investment banking: It’s all about risk management
07:00 – The hedge fund marble game and what it reveals about calculated risk-taking
08:29 – CIA culture and core principles: “You shall know the truth and it will set you free”
10:54 – Why candor and unvarnished truth are essential for wealth managers and their clients
12:08 – The problem of information overload and the danger of conventional wisdom
14:41 – Case studies: Ukraine offensive and October 7th Israel attack—when groupthink fails
16:07 – How Jack’s intelligence platform delivers actionable insights to wealth managers
19:44 – The professionalization of wealth management and the mission-driven approach of top advisors
23:10 – Beyond intelligence: Comprehensive services including travel security, cyber protection, and crisis support
26:03 – What asset managers vs. wealth managers need from geopolitical intelligence
31:44 – The real “rules of the game” in intelligence work and why guardrails matter
33:01 – How to gather information ethically, legally, and effectively
36:05 – Why the world feels more chaotic than ever, and whether we’re nearing a tipping point
37:13 – The black swan problem and why there may be 20, not three
38:30 – Optimism amid chaos: Historical patterns suggest we’re heading toward more peace
40:41 – Why wealth managers want prosperity for everyone and could be a stabilizing force
42:23 – Why skepticism (not cynicism) is a top intelligence skill: Challenge every assumption
44:16 – The implications of social media and AI, especially for children and society
46:27 – Jack’s coolest operations and what it means to “touch history”
47:26 – Afghanistan and the Stinger missile: How one decision helped end the Cold War
49:20 – What Hollywood gets right (and wrong) about spies: 24, The Americans, Homeland, Jason Bourne
50:21 – Dinner with Sean Connery (James Bond) and the truth about martinis
53:09 – Jack’s “Don’t Do That” Lesson #1: Trust your instincts (but make sure you have a well-developed gut)
54:56 – Jack’s “Don’t Do That” Lesson #2: Never underestimate people’s egos
57:12 – Why wealth management is half psychiatry: The art of sizing up people
58:12 – The surprising parallels between CIA skills and wealth management excellence
1:00:06 – How to access Jack’s intelligence products at The Arkin Group
1:00:27 – Closing remarks and sponsor message
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About Our Guest:
Jack Devine, founder and chairman of The Arkin Group, is a 32-year veteran of the Central Intelligence Agency (CIA) where he served as both Acting Director and Associate Director of the CIA’s operations outside the United States as well as chief of the Latin American Division, the head of CIA’s Counternarcotics Center and the head of CIA’s Afghan Task Force. He was awarded the CIA’s Meritorious Officer Award for this accomplishment and is the recipient of the Agency’s Distinguished Intelligence Medal and several meritorious awards.
Jack has written widely on intelligence including his two books, Spymaster’s Prism: The Fight Against Russian Aggression and Good Hunting: An American Spymaster’s Story, along with Op-Ed articles for The Washington Post, The Wall Street Journal and The Financial Times. He has also made guest appearances on CBS, NBC, MSNBC, Fox News, and Bloomberg News, and is frequently called-upon to share his opinion on myriad geopolitical events. Jack is a member of the Council on Foreign Relations.