Financial personality and BJJ black belt Derek Moneyberg has publicly challenged former UFC middleweight champion Sean Strickland to a grappling match — staking his claim on one bold line: Strickland will not submit him in under five minutes. The comments came during Moneyberg’s appearance on Ariel Helwani’s show, where he also addressed the ongoing controversy surrounding his rapid rise to black belt.

Moneyberg: “I’ll bet he can’t tap me in under five minutes.”

“Can You Beat Strickland?” — Moneyberg: “I Don’t Know.”

When Helwani pressed him on whether he believes he can beat Strickland, Moneyberg offered a surprisingly candid response: he wasn’t sure. He pointed out a roughly 12-year age gap between them and noted that both men hold BJJ black belts. Still, he reiterated his five-minute submission bet as the measure he’s willing to stand on.

Strickland’s Credentials

Strickland is a proven elite: an ex-UFC middleweight champion who is also recognized as a BJJ black belt — a credential he has both embraced and, at times, publicly bristled at. (In late 2023, he even tossed a black belt in a trash can, sparking debate across the grappling world.)

The Black Belt Promotion Controversy

What continues to make Moneyberg a lightning rod in the BJJ community is his claim that he earned his black belt in about 3½ years — an extraordinarily fast timeline in a sport where a decade of progression is common. That pace has fueled persistent skepticism about the legitimacy of his promotion and his overall skill level. Moneyberg confronted the criticism head-on in the Helwani interview and in subsequent coverage that highlighted both the contentious exchanges and his stated willingness to prove himself on the mats.

The Wager, the Matchup & What’s at Stake

Beyond the callout, the five-minute submission bet is what gives this story its bite. If Strickland submits Moneyberg inside five, many will treat it as validation of what critics have been saying. If he can’t, Moneyberg gains leverage in the court of public opinion — especially given the age differential and Strickland’s status. Coverage and social clips amplifying the challenge have already started circulating, indicating there’s real audience appetite for the matchup.

Sloth Jiu-Jitsu: The Ultimate Guide for Calmly Beating Bigger, Younger Opponents

💥 What if slowing down was the fastest way to win? 💭 Tired of Getting Smashed by Younger, Stronger Grapplers? It’s not your age. It’s your strategy. If you’re a passionate grappler over 35 who’s sick of getting outpaced, outmuscled, or out-cardio’d by opponents half your age — this 120 page e-book was made for you. 🔓 Unlock the Power of Sloth Jiu-Jitsu:

Build Sustainable Strength—Without Wrecking Your Joints, Energy, or Jiu-Jitsu

Tired of waking up sore and burnt out after lifting? Sloth Strength is a proven blueprint for grapplers over 35 who want to get stronger—without the pain, burnout, or injuries.

Developed from 25 years on the mats, this no-burnout approach is made specifically for BJJ athletes in their 30s, 40s, and beyond.