Digital Social Hour – Episode #1556

Guest: Derek Moneyberg

Host: Sean Kelly
Date: October 6, 2025

Episode Overview

This episode of Digital Social Hour features controversial business coach and entrepreneur Derek Moneyberg. Sean Kelly dives into Derek’s recent headlines – from the uproar around how he earned his black belt in Brazilian Jiu-Jitsu, to online beefs with notable fighters like Sean Strickland and controversies around his aggressive style and rapid rise. Derek gives his unfiltered take on haters, reputation, fighting culture, and the reality of building wealth through discipline – not hype. The conversation also covers long-term investment thinking and the discipline needed to thrive both in martial arts and business.

Key Discussion Points & Insights

1. The Strickland Incident: Clicks, Confrontation & Reputation

• Moneyberg’s Version of Events: Derek recounts how Sean Strickland allegedly acted tough online but avoided a real conversation or grappling session in person.
  • Quote: “He takes the phone out when we’re by the elevator, and then he totally, totally changes his persona. And now he’s a tough guy on camera.” (00:00, 16:04)
  • Derek claims Strickland refused to speak or train off-camera, only to act confrontational for his followers.
  • Derek says he’s invited Strickland to train together and privately messaged him, but Strickland continued posting what Derek calls lies damaging to his reputation.
• Legal and Personal Fallout:
  • Derek mentions he’s only sued two people in his life but plans for Strickland to be the third due to reputational damage (11:40, 18:34).
  • “You can say you doubt my black belt, but you can’t say that I steal money from people.” (17:19)
• Perspective on Online Haters:
  • Haters are often “jealous fans” who hate themselves the most (09:10).
  • “The number one thing a hater hates is himself... It’s almost always a guy.” (09:10)
  • Animal world analogy: Hyenas taking from lions as a metaphor for online critics (07:25).

2. Moneyberg’s Rapid Black Belt in Jiu-Jitsu: Controversy Explained

• How He Did It:
  • Derek says he compressed the normal 10-15 year process into under 4 years by training daily with top coaches and building several private gyms.
  • “I got my black belt in three years and seven months… I put in the same number of hours, just in a more compressed amount of time with… the best coaches in the world.” (00:43)
  • He spent millions of dollars on gyms and training, and objects to accusations that he “bought his belt.”
• Response to Haters:
  • Dismisses the argument he just paid for his credentials: “That doesn’t mean you didn’t do the work.” (05:28)
  • Calls out critics as those who took longer or didn’t have his resources.
  • Perspective: Others are upset by his success or using his name for attention: “They’re trying to use your name to leapfrog and get more clicks and views.” (07:08)
• Realism about Skill Levels:
  • Derek admits there are purple belts in elite gyms who could “kill almost every black belt.” (03:08)
  • Acknowledges he's not a pro fighter and doesn’t compete at the world’s top tournaments, positioning himself as a serious hobbyist.

3. The Craig Jones Invitational & Marketing Games

• Being Used for Publicity:
  • Craig Jones used Derek’s name and likeness to promote his event without prior permission. Derek is more impressed than annoyed (“the audacity of this, in kind of a good way…” 19:24).
  • Finds it “shameless but admirable” in terms of marketing, and acknowledges it made them both bigger talking points.
• Derek’s Approach:
  • Shares DMs with Jones and details their humorous exchange. (22:16–24:10)
  • Would have insisted on contract terms if he were to participate; he respects Jones’ talent and promotional abilities.
  • “He’s a promoter. Clicks and views… Not a very high integrity person in my estimation, but great grappler, great promoter.” (21:10)

4. Perspectives on Martial Arts, Discipline & Culture

• Why He Trains:
  • Derek sees martial arts as part discipline, part self-defense, and a vehicle for personal improvement.
  • “When you’re sixty-something, can you really protect yourself?...If you don’t have good fight training, that’s just not realistic.” (25:51)
• Respect for Fighters:
  • Says that high-level MMA fighters tend to be the most honorable, sincere people he knows: “It’s the last enclave of people that are very sincere, hard working.” (26:36)
• Accountability in Fighting:
  • Tells a story from Lyoto Machida: "There’s nothing to say about the referee. Just be better." (28:34)

5. Wealth Building & Investment Philosophy

• Investment Discipline and Psychology:
  • Warns strongly against emotional reactions and trend chasing in investing: “People that buy individual stocks tend to lose money.” (36:34)
  • Emphasizes boring, overlooked assets over hype, e.g., uranium ETFs as a play on future energy needs (32:09–33:32).
  • “There’s so much capital that goes into that short-term thinking, that I have to think about, well, what are they not focused on yet?” (33:40)
  • Anti-leverage: “It’s mathematically impossible to go bankrupt if you don’t have debt.” (40:09)
• Teaching vs. Tipping:
  • He doesn’t give specific investment picks to followers. Focuses on teaching decision-making frameworks. (35:52)
  • “I teach people how to make better financial decisions and how to be a good independent thinker… I teach people how to think.” (35:52)
• Handling Losses:
  • Recounts being down 70% in 2008-2009, but sticking with it and quadrupling his wealth (38:08–39:44).
  • Experience and education let him weather tough markets.

6. Personal Wealth, Risk, and Security

• Personal vs. Business Risk:
  • Doesn’t like personal debt and prefers to keep leverage low on properties he uses personally (40:27–43:30).
  • Sees more sense in leveraging business/investment properties with strong cash flow.
• Threshold for Freedom:
  • Describes reaching the point where investments can fund his lifestyle, not just business income.
  • “I don’t have to do anything I don’t want to.” (43:47)
• No Get-Rich-Quick Nonsense:
  • Derek rejects the idea of instant riches: “I didn’t get rich quick… You’re not going to be a millionaire overnight.” (46:49)
  • Credits his wealth to decades of work, not shortcuts or hacks.

Notable Quotes & Memorable Moments

• On Haters:
  “The number one thing a hater hates is himself. …It’s almost always a guy.”
  — Derek Moneyberg (09:10)

• On Sean Strickland’s Behavior:
  “He takes the phone out when we’re by the elevator, and then he totally, totally changes his persona. And now he’s a tough guy on camera.”
  — Derek Moneyberg (00:00, 16:04)

• On Buying Your Belt:
  “I paid my coaches. I also paid my tuition at my university… That doesn’t mean you didn’t do the work.”
  — Derek Moneyberg (05:28)

• On Martial Arts Accountability:
  “‘There’s nothing to say about the referee. Just be better.’ That really sticks in my head in other areas of life.”
  — Derek Moneyberg (28:34)

• On Investment Risk:
  “It’s mathematically impossible to go bankrupt if you don’t have debt.”
  — Derek Moneyberg (40:09)

• On Wealth and Paradox:
  “Later in life, there’s days I made a few million dollars in a day, but that took 40 years of me thinking about it and strategizing and doing the right things before those.”
  — Derek Moneyberg (46:49)

Timestamps for Major Segments

• 00:00, 16:04: Derek breaks down the alleged Strickland confrontation and online persona shift.
• 00:43–06:27: Derek explains his accelerated black belt journey and counters accusations that he bought his belt.
• 07:10, 09:10: Philosophizes on haters and online critics; animal kingdom analogies.
• 11:15–18:34: In-depth recounting of the Strickland beef, attempts to resolve it, and legal plans.
• 19:14–24:10: The Craig Jones Invitational’s use of Derek’s name and the inside story from their direct messages.
• 25:18–29:40: Why he trains martial arts, the culture of MMA, and discipline analogies.
• 29:53–36:26: Stock market philosophy, risk, emotional discipline, and learning from losses.
• 38:08–43:47: Surviving massive investment losses, personal property and debt philosophy, security.
• 46:02–47:39: Final thoughts on coaching, investing, and the myth of fast wealth.

Tone & Style

• Derek is blunt, confident, occasionally self-deprecating, and frequently calls out “haters” or critics.
• The conversation is direct and sometimes irreverent, especially when lampooning online “tough guy” behavior.
• Throughout, Derek’s advice is focused on realism, personal accountability, hard work, and thinking long-term – whether in business or martial arts.

For those curious about Derek Moneyberg’s provocative approach – from investing and coaching to fighting and online controversy – this episode delivers a raw, unfiltered, and instructional listen.