Cleared Hot Podcast – Ep. 431: Violence Is Escalating | Caleb Gilbert

Date: February 2, 2026
Host: Andy Stumpf
Guest: Caleb Gilbert
Length: Approx. 2 hrs 40 min

Episode Overview

This episode features Caleb Gilbert, an executive protection professional with decades of experience, discussing the escalating nature of violence—particularly high-profile attacks and security in the current climate. Host Andy Stumpf and Caleb reflect on recent assassinations, breakdowns in security protocols, how the nature of violence has changed, as well as practical advice on personal and digital security for both high-net-worth individuals and everyday people.

The conversation draws on Caleb's background in Hollywood and Silicon Valley, the transition to entrepreneurship, and his philosophy on risk, personal success, and living a fulfilled life in a dangerous world.

Key Themes & Discussion Points

1. The Changing Landscape of Violence & Executive Protection

High-profile Assassinations & Security Complexities

• The episode starts with a discussion of the assassination of Charlie Kirk and its impact on the executive protection industry.
• Caleb explains the inherent limitations and complexity of managing risk in public, open-air venues, especially for polarizing figures (00:40–06:20).
  • "There's no legal way for someone in the private sector to cover all the bases of risk that you're looking at in that picture... The assets that are required to pull something like that in this venue are literally illegal for the private sector." – Caleb (04:03)
• The difference in resources and protocols between government-level security (e.g., POTUS) and private sector is vast.

Escalation and Frequency of Attacks

• Noted a spike in attacks on principals and protectees in the past 18 months—catalyzed by incidents like the Charlie Kirk assassination and UHC shooting (09:02–10:10).
  • “I've never seen the thin barrier to violence that we're seeing today.” – Caleb (15:49)
• Attack risk is now felt by those who never thought they’d be targets, including high-net-worth, non-public individuals.

The Unpredictability & Human Factor

• Discussed the reality that no plan can mitigate every risk, especially when the protected person can veto advice, waive off details, or expose themselves (11:59–12:50).
  • "A nefarious actor has the ability to choose the time and the place. And if they're choosing the time and the place, they don't have to get it right every day like we do." – Caleb (11:59)

Liability & Professional Boundaries

• There’s a point where security professionals must declare the risk “unsustainable” and refuse service, even if that jeopardizes contracts or angers clients (21:23–22:39).
  • “...for the well being of the protector...do I want to put my team in harm's way or do we do a full stop?” – Caleb (21:57)

2. Incidents Driving Protocol Change and Industry Shifts

Charlie Kirk Assassination (Utah)

• Provides a detailed breakdown of how teams plan for events, the use of technology, and why resource constraints make full mitigation impossible (19:18–19:47).
  • “Use a combination of tools, combination of redundancy, combination of taking your advanced planning and combining that with your operations, then you reduce the avenues an attacker can get to you and you increase your ability to get your protectee off the X.” – Caleb (19:47)
• Post-incident reviews often suffer from armchair quarterbacking and conspiracy theories, which muddy actionable discussion (30:16–31:12).

Industry Response Cycle to Violence

• Security responses spike after major events, then are cut after the perceived threat declines—until the next crisis (27:35–29:10).
  • “The difference...is the cadence of attacks on principles has increased...That is keeping it at the forefront so you’re not seeing budget cut.” – Caleb (27:46)

3. Caleb's Journey – From Hollywood to Silicon Valley and Entrepreneurship

Breaking Into Executive Protection

• Random encounter in a park with corporate agents led Caleb to pursue executive protection, eventually moving from parking lot gigs to A-list details (33:58–41:42).
• Describes the lengthy grind and sacrifices to break into high-level details, highlighting misconceptions shaped by pop culture (movie “The Bodyguard,” etc.).

The Nature of Protectees: Fame, Wealth, and Human Quirk

• Differences between Hollywood celebrities (fame, less money, more ego) vs. Silicon Valley titans (huge money, less public attention, but greater operational complexity) (47:32–50:32).
  • "All of a sudden, you have these people who are worth 10, 20 billion dollars who nobody knows who they were other than the fact they have six knuckle draggers walking around with them." – Caleb (47:38)
• Created covert protection teams to solve the attention-drawing problem for anonymous billionaires, fusing tech, counter-surveillance, and profile management.

Entrepreneurship & Leadership Philosophy

• Left the corporate world due to frustration with vendor models, founding White Glove with an employee/shareholder model and embedded, continuously trained teams (51:22–69:22).
• Emphasizes company investment in continuous training, mentoring, and objective performance metrics for profit sharing.

4. Protecting the Everyday Person – Digital & Physical Awareness

Digital Threats and Modern Risks

• Emphasizes that the average person’s greatest security risks are now digital (credit card fraud, data compromise, social engineering) over physical violence (72:42–74:27).
• Discussed the digital “footprint” as a key attack vector, especially via children’s online activity (99:08–100:30).

Situational Awareness Principles

• Provided a simple color-coded, “thumbs up/sideways/down” system for evaluating personal safety in environments:
  • Thumbs up: Baseline, all seems normal.
  • Thumbs sideways: Something feels off—pay attention, don't necessarily act.
  • Thumbs down: Clear and present threat—create time and distance, leave or act appropriately. (76:35–80:49)
• Cautions against overcomplicating security—trust intuition, and don’t ignore discomfort signals (76:35–79:10).
  • “But they do have something called intuition...that same level of understanding is something we can all put into play. Doesn’t matter if it’s a secretary or a CEO.” – Caleb (76:35)

Time, Distance, and Managing Escalations

• Numerous anecdotes (e.g., road rage) reinforce the importance of time and distance in de-escalating threats and preventing violence (80:49–87:42).
  • “Everything is fine until it’s not. If you can really flatten that curve between everything being fine and not being fine...you have time and distance.” – Andy (80:58)

5. Current & Future Risks: Polarization, Disinformation, and Looking Ahead

Social Division and Info Warfare

• Significant focus on how disinformation—often from hostile nations—is accelerating social division, conspiracy, and violence (135:36–138:44).
  • “...the vast majority of trending data on social media is being pushed by somebody.” – Caleb (137:19)

Importance of Seeking Truth Over Bias

• Advocates for a mindset of pursuing unbiased truth rather than confirmation, urging listeners not to fill information gaps with conspiracism (139:25–141:31).
  • “My favorite weapon is truth ... that pursuit in and of itself is kind of a distillation process for me.” – Caleb (140:18)

The Future: More Violence, Need for Awareness

• Forecasts that trends indicate an increase in violence and risk, citing upcoming elections and ongoing polarization (134:09–134:51).
• Urges objective thinking, unity, and returning to core American values as an antidote.

6. Philosophy on Success, Money, Fulfillment

• Having observed both “old money” and “new money,” Caleb reflects on the hollowness of wealth as a sole objective (104:14–125:47).
  • “I don't ever want to be worth more than $20 million… I don't want to be controlled by the excess that's in my account.” – Caleb (104:17)
• For him, true success is the freedom to spend time with family and positively impact others, not chasing an ever-increasing paycheck.

Notable Quotes & Memorable Moments

| Timestamp | Speaker | Quote | |-----------|---------|-------| | 04:03 | Caleb | "There's no legal way for someone in the private sector to cover all the bases of risk..." | 15:49 | Caleb | "I've never seen the thin barrier to violence that we're seeing today." | 19:47 | Caleb | "Use a combination of tools... you increase your ability to get your protectee off the X." | 21:57 | Caleb | "Do I want to put my team in harm's way or do we do a full stop?" | 47:38 | Caleb | "...10, 20 billion dollars who nobody knows...other than the fact they have six knuckle draggers walking with them." | 76:35 | Caleb | "But they do have something called intuition...and that same level of understanding is something that we can all put into play." | 80:58 | Andy | "Everything is fine until it's not. If you can really flatten that curve between everything being fine and not being fine...you have time and distance." | 99:08 | Host | "Talk about leverage on a parent. My goodness...there’s no vocabulary to describe what you would do." | 134:51 | Caleb | "At the end of the day, if we just remember we’re all humans...I think we just need a reality check as a nation." | 140:18 | Caleb | "My favorite weapon is truth... that pursuit in and of itself is kind of a distillation process for me." | 104:17 | Caleb | "I don't ever want to be worth more than $20 million..." | 125:47 | Caleb | "As I've achieved different milestones in my life, I want to maintain that cognitive awareness that it's not all about money, it's not all about the experience…it’s about the people around you."

Practical Insights for Listeners

• Everyday security: Don't try to be a secret agent, but don't ignore your intuition. Use "time and distance" to manage risks.
• Digital hygiene: Your greatest exposure is online—protect digital data, watch what your children do online, don't overshare, and consider using privacy/deletion tools.
• Don't seek confirmation, seek truth: Be wary of weaponized information and online polarization. Question if what you see online mirrors your real life.

Timestamps for Key Segments

• 00:40–06:20: Complexity and limitations of protective security (w/ Charlie Kirk reference)
• 09:02–11:59: Recent attacks and industry ripple effect
• 21:23–22:39: Risk threshold and refusing protection
• 19:18–19:47: Technology and redundancy in protective planning
• 30:16–31:12: Social media, conspiracy, and post-incident chaos
• 47:32–50:32: From A-list celebrities to anonymous billionaires
• 76:35–80:49: Thumbs up/sideways/down—intuition-based personal security
• 80:49–87:42: Time and distance stories (road rage, risk management)
• 135:36–138:44: Polarization, info warfare, disinformation
• 134:09–134:51: Future violence trends and need for objective thinking
• 104:17–125:47: Philosophy of money, wealth, success, and meaning

Tone and Style

The episode is candid, storytelling-driven, and at times rawly honest. Both speakers use personal anecdotes, dry humor, occasionally gritty language, and a relentlessly practical lens for both professional and everyday security.

Final Thoughts

Caleb’s closing: Direct gratitude for the audience, veterans, and the reality that those who serve enable both his world and others.
Andy reflects on the shared challenge of living ethically, managing risk, and finding meaning beyond status or money.

For more:
Follow Caleb at White Glove Security and connect with host Andy Stumpf through Cleared Hot.

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