Money And Wealth with John Hope Bryant

Episode: "Rowing Through Risk" w/ Tim Crockett

Date: September 18, 2025
Host: John Hope Bryant (The Black Effect and iHeartPodcasts)
Guest: Tim Crockett

Overview of Episode

In this special episode of Money and Wealth, John Hope Bryant welcomes Tim Crockett—Chief Risk Officer at Operation Hope, British Special Forces veteran, security expert, and extreme adventurer. Bryant uses Crockett’s extraordinary life and recent adventure (rowing 2,400 miles across the Pacific with his son) as a masterclass on managing risk, developing resilience, and why risk management is fundamental to building, preserving, and generationally transferring wealth. The conversation covers everything from Special Forces mindset to practical lessons on financial literacy to surviving both literal and metaphorical storms.

Key Discussion Points and Insights

1. Risk Management: From Boardroom to Battlefield

• Visible vs. Invisible Security:

  • Bryant introduces Crockett through the lens of personal and organizational risk management, making clear distinctions among uniformed security presences, plainclothes protection, and the invisible, elite tier Crockett occupies (04:14–07:18).
  • "[Security guards] are managing retail threats…but the guys with the little earpieces—they don’t want to draw any attention to themselves whatsoever. And Tim’s the next level above that." — John Hope Bryant (06:28)

• Why High Performers Need Risk Experts:

  • As success and public exposure increase, so does threat level—requiring professionals like Crockett to create a “bubble” of protection around high-profile individuals and organizations (12:12–14:18).
  • "With success comes elevated risk. You can become a target: the individual, the role, the institution." — Tim Crockett (13:52)

2. Tim Crockett’s Elite Background

• "How does someone get into this field?…When the FBI recommends you, you know you do hot crap." — John Hope Bryant (12:12)

  • Crockett describes his path: Royal Marines ➔ UK Special Boat Service (equivalent of US Navy SEALs), working globally, running event security, then transitioning post-military to high-level project management and security for media, corporations, and non-profits (16:26–20:02).

• Resilience and Pivoting: Lessons in Overcoming Ceilings

  • Crockett hit a promotion ceiling in the Special Forces, pivoted to a new career, and gradually transitioned his skill set to the risk/security sector—a lesson in proactive reinvention (18:33–20:09).

3. Bridging Physical & Financial Risk

• Transference of Skills & Mindset:

  • Crockett highlights how discipline, risk-calculation, and preparation from “the circuit” (exclusive security professionals worldwide) translate into business (20:23–22:09).

• Firsthand in High-Stakes Environments:

  • Crockett recounts being embedded with journalists in Afghanistan, including recovering Osama Bin Laden’s video library post-9/11—a pivotal, dangerous, and high-impact operation (21:29–24:46).
    • "I helped recover Bin Laden’s video library and hand-carried almost 200 VHS tapes from Kandahar to Atlanta." — Tim Crockett (24:35)

4. Mental Health & Financial Stress: Veterans in Civilian Life

• The ‘Kraken’ of PTSD & Financial Stress:

  • Crockett’s ocean rows are charity drives for mental health support among veterans, inspired by losing friends to suicide. He draws a direct connection between resilience, purpose, and both psychological and financial stress (36:17–41:33).
  • "Often, that [financial] stressor—that is why so many people give up. Debt is a stressor." — Tim Crockett (41:33)

• Transitioning Dangers:

  • Many elite service members leave careers with little financial literacy, often resulting in rapid debt and loss of support systems—a situation mirrored across public service professions (43:08–44:42).
  • Bryant powerfully connects this with the history of Black soldiers and the Freedman’s Bank, highlighting how predatory lending is a risk preying on the financially illiterate across generations (44:42–47:42).

5. Rowing Across Oceans: Metaphor and Reality

• Atlantic & Pacific Crossings:

  • Crockett solo-rowed the Atlantic in 2018 and, later, rowed the Pacific (San Francisco to Hawaii) with his 19-year-old son—a feat earning a world record (10:00–10:58, 36:07–51:27).
  • Purpose: Raise awareness and resources for mental health challenges facing veterans.

• Overcoming the Impossible:

  • Details: 48 days at sea, 2,400+ nautical miles, storms, near capsizes, equipment challenges, exhaustion, danger of missing the Hawaiian islands—narrated in vivid, suspense-filled detail (52:15–59:09, 64:10–73:14).

  • Psychological Resilience: Persevering under hardest conditions is likened to the perseverance needed in financial adversity.

  • Memorable Moment: On Day 3, Crockett’s son, overwhelmed, says: “I’m not sure if I can do this.” Crockett refuses to make the decision for him—reinforcing the lesson that resilience and persistence are choices (64:58–66:35).

6. Translating Adventure to Financial & Business Lessons

• Risk: Not Just Downside Protection, But Upside Opportunity

  • "If you can manage all of the downside, you create opportunities. Once you understand risk, you can exploit and take educated risks." — Tim Crockett (78:51)
  • Whether navigating the ocean or navigating business, knowing your threats (literal or financial) allows you to move faster and more strategically (79:04–80:04).

• Practical Tips on Security for Wealth-Builders:

  • Protect digital reputations, avoid sharing sensitive details publicly, use secure communications, do risk assessments for physical ventures, and always be vigilant in unknown environments (82:13–86:21).
  • "If you take time to analyze, you’ll find the crux of it. As an entrepreneur, by the time I do something, I’ve run all the risk out of it." — John Hope Bryant (86:21)

7. Memorable Quotes & Moments

• On Quiet Confidence and Real Power:
  “He’s the kind of power I like…when you got real power, you don’t need to flex. It’s just an is.” — John Hope Bryant (08:10)

• On the Strong Why:
  “Enthusiasm will get you so far…discipline will get you so far…but you need something that’s bigger than that to keep pulling you through—the strong why.” — Tim Crockett (38:05)

• On Invisible Service:
  “This group of 300 around the world—they live in silence, they serve in secrecy, and often they die without recognition.” — John Hope Bryant (40:30)

• On Parenting & Risk:
  “When it’s your son, it’s different...I was much more measured and risk-averse than when I was solo.” — Tim Crockett (59:09)

• On Resilience:
  "Never ever, ever, ever give up…Success is going from failure to failure without loss of enthusiasm." — John Hope Bryant (75:33)

Timestamps for Major Segments

• Bryant Introduces Risk Management & Tim Crockett: 02:26–06:28
• Crockett’s Special Forces/Early Security Career: 16:26–24:35
• Bin Laden Video Library Recovery: 24:35–34:04
• Mental Health, Veterans, & Financial Literacy: 36:07–47:42
• Rowing the Atlantic & Pacific—Purpose and Ordeal: 51:26–66:45
• Greatest Highs/Lows of the Row: 69:40–73:14
• Why Risk Management Equals Wealth Preservation: 75:57–82:13
• Practical Security/Wealth Protection Advice: 82:13–86:21
• Final Lessons & Reflections: 86:21–End

Actionable Takeaways

• Wealth is not just about what you make, but what you keep—and protect.
• Managing risk is essential for scaling and sustaining personal and organizational wealth.
• Resilience, a clear purpose (“strong why”), and discipline are key to pushing through adversity in business, finance, or life.
• Financial literacy and mental health support are crucial for successful transitions, especially for veterans and underserved communities.
• Modern risk includes physical, digital, and reputational threats—plan for all.
• Leverage the positive side of risk: with preparation, risk management creates room for growth and opportunity.

For More Information

• Tame the Kraken: Crockett’s mental health nonprofit for veterans/row project (website)
• Operation HOPE: Volunteer opportunities in financial counseling

Closing Thoughts

Tim Crockett’s story is a powerful real-world parable on why managing risk—whether at sea, in business, or in life—is indispensable to building lasting wealth, personal resilience, and generational legacy. John Hope Bryant expertly bridges the world of high-stakes security with practical advice for entrepreneurs, business leaders, and anyone striving to thrive while rowing through risk.