
INTERVIEW | Make Money by Shaping Chaos and Making Better Decisions Under Pressure with Kyle Vowinkel
20/9/2026
0:00
29:37
Kyle Vowinkel is a decorated former FBI senior executive, West Point graduate, keynote speaker, and author of the forthcoming book Shaping Chaos. During more than 24 years with the FBI, Kyle served on both the FBI Hostage Rescue Team and Crisis Negotiation Unit, making him one of only five agents to serve on both. He has negotiated with kidnappers, pirates, and terrorists and deployed alongside U.S. Special Operations Forces. Today, he helps leaders assess risk, make better decisions under uncertainty, influence others, and act decisively when the stakes are high.
On this episode we talk about:
Why Kyle decided to serve his country and ultimately pursue a career with the FBI
How earning money from a paper route at 11 taught him the value of saving and investing early
The financial lessons Kyle learned from his father and through government service
How Kyle built nearly 32 years of government service and incorporated his military time into his federal retirement
Launching his business, Inner Perimeter, after retiring from the FBI
How professional connections helped create opportunities for Kyle after leaving the FBI
Why nurturing relationships over the long term is one of the most valuable things you can do for your career
The radically different approaches Kyle learned from serving on both the Hostage Rescue Team and Crisis Negotiation Unit
How lessons from high-stakes FBI operations translate directly into sales, leadership, and entrepreneurship
The four-step “path to influence”: framing, empathy, rapport, and giving people choices
How Kyle used genuine connection and empathy during the Boston Marathon bombing manhunt
Why “control can extract compliance, but choice creates commitment”
How giving people agency can make them more committed to a decision
Why empathy doesn't require agreeing with someone
The importance of seeing a situation from another person's perspective before trying to influence them
What entrepreneurs and leaders can learn from crisis-response decision-making
Why leaders should establish decision-making triggers before a crisis happens
How businesses can prepare for uncertainty by planning for best-case, most likely, and worst-case scenarios
Kyle's forthcoming book, Shaping Chaos, and the lessons he drew from his FBI career
Top 3 Takeaways:
1. Make the hard decisions before the pressure hits.Kyle explains that emotions tend to rise while rational thinking declines as a crisis intensifies. One way to counter that is to establish decision-making triggers in advance. Whether you're responding to a kidnapping or preparing a business for a major market event, knowing ahead of time what circumstances will trigger specific actions can help teams respond decisively rather than emotionally.
2. Influence starts with understanding, not coercion.Kyle's experience as a crisis negotiator taught him that people are more receptive when they feel seen, valued, and heard. Framing the conversation from the other person's perspective, demonstrating empathy, building genuine rapport, and giving people choices can create a much stronger path to influence than simply trying to force compliance.
3. Relationships remain a competitive advantage.Kyle emphasizes that professional relationships need to be nurtured over time rather than activated only when you need something. Checking in, helping others, and building genuine connections creates a network that can support you throughout different seasons of your career. As Kyle puts it, AI may change how we work, but it can't replace the one-on-one relationships that help people succeed.
Notable Quotes:
“I’ve been working since I’m eleven.”
“You can let chaos shape you, or you can try to shape the chaos.”
“Control can extract compliance, but choice creates commitment.”
“When people feel that they are seen, valued, and heard, that’s the kind of three trifecta.”
“Empathy is not judgment.”
“You don’t just want them to go along because they have to go along. You want them choosing to.”
“You make the hard decisions in advance.”
Connect with Kyle Vowinkel:
Website: https://www.kylevowinkel.com/
Book: Shaping Chaos, available for pre-order ahead of its November release
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