Episode Details

Rob Menn is back for the fifth and final part of our conversation, and we're ending this one with some serious fight debates.

We start by talking about investing based on cultural trends, whether the massive amount of money pouring into artificial intelligence is creating an AI bubble, and how recognizing where society is heading could potentially create investment opportunities.

Then we get into Rob's world: fighting.

We debate the greatest UFC fighters of all time, Anderson Silva vs. Jon Jones, whether wrestling is scored too heavily in MMA, and whether AI could eventually do a better job judging fights.

From there, we move into boxing and debate Floyd Mayweather's defensive style, whether winning rounds is the same thing as actually beating your opponent, Mayweather vs. Pacquiao, and ultimately our Top 5 boxers of all time.

And Rob makes his position very clear: Prime Mike Tyson beats everybody.

🎙️ In this episode:

•  Investing based on cultural trends 
•  Is AI becoming an investment bubble? 
•  Finding the next major trend before Wall Street does 
•  Why younger generations are drinking less 
•  Rob's MMA training 
•  Will Jon Jones fight again? 
•  Anderson Silva vs. Jon Jones 
•  The Top 5 UFC fighters ever 
•  Why Anderson Silva is Rob's GOAT 
•  GSP, Khabib, Mighty Mouse & Stipe Miocic 
•  Is wrestling scored too heavily in MMA? 
•  Should takedown defense earn points? 
•  Could AI eventually judge UFC fights? 
•  Floyd Mayweather's defensive boxing style 
•  Did Mayweather really beat Oscar De La Hoya? 
•  Why Sugar Ray Leonard and Muhammad Ali fought differently 
•  Winning the scorecard vs. actually beating your opponent 
•  Mike Tyson's incredible rise 
•  Cus D'Amato's influence on Tyson 
•  Would prime Tyson beat Evander Holyfield? 
•  Tyson vs. Jake Paul 
•  Was something off about the Tyson-Paul fight? 
•  Our Top 5 boxers of all time 
•  Manny Pacquiao vs. Floyd Mayweather 
•  Why Canelo deserves more respect 

🧠 Big questions from Part 5:

•  Is AI an investment opportunity or a bubble? 
•  Who is the greatest UFC fighter ever? 
•  Should MMA judging change? 
•  Is Mayweather's style brilliant or just boring? 
•  Is winning a decision the same as truly beating someone? 
•  Who wins: prime Tyson or prime Ali? 
•  Would Pacquiao have beaten Mayweather five years earlier? 
•  Who belongs in the Top 5 boxers ever? 

⏱️ CHAPTERS / TIMESTAMPS
00:00 Investing Based on Cultural Trends
01:30 Is AI Becoming a Bubble?
03:22 Investing in Trends Before Everyone Else
04:21 How Younger Generations Change Markets
05:37 Rob's MMA Training
06:33 Jon Jones & the UFC Heavyweights
07:20 Top 5 UFC Fighters of All Time
07:30 Anderson Silva vs. Jon Jones
08:55 Why Anderson Silva Was Different
09:36 Who Rounds Out the UFC Top 5?
10:18 Mighty Mouse, Stipe & Khabib
10:50 Is Wrestling Scored Too Heavily?
11:37 Should Takedown Defense Score Points?
13:02 Could AI Judge UFC Fights?
14:13 Why Matt Hates Mayweather's Style
15:09 Did Mayweather Beat De La Hoya?
16:13 Why People Wanted Mayweather to Lose
17:05 Ali & Sugar Ray Leonard vs. Mayweather
18:21 Winning a Decision vs. Beating Someone
19:07 Mayweather's Lifestyle & Spending
22:53 Top 5 Boxers of All Time
23:17 Why Prime Mike Tyson Was Terrifying
23:23 Tyson vs. Muhammad Ali
24:12 Would Tyson Have Beaten Holyfield?
24:33 Mike Tyson's Incredible Life Story
25:06 Why Tyson Was Smarter Than People Realized
25:51 How Cus D'Amato Created a Champion
27:03 Tyson vs. Jake Paul — Was Something Off?
29:04 Rob's Top 5 Boxers
29:45 Matt's Top 5 Boxers