Entrepreneur, investor, and former “Shark Tank” star Matt Higgins joins the Chuck ToddCast for a wide-ranging conversation on ambition, politics, media, and the rapidly accelerating drone arms race. Higgins reflects on his rise from humble beginnings to serial entrepreneurship, why highlighting adversity can sometimes unintentionally promote victimhood, and how government should focus on leveling the playing field with empathy—not bureaucracy. He also explains why America is undergoing a political realignment and how leaving politics reshaped his view of its inherent narcissism. From the personalization of media to the implicit bias baked into journalism, Higgins warns about how online life can warp our sense of reality and why LinkedIn has succeeded by avoiding the toxicity of other platforms.

The discussion then turns to the future of warfare, where drones have transformed the battlefield and triggered the most significant arms race since the nuclear age. Higgins breaks down how the Ukraine war changed everything, why the U.S. is dangerously dependent on Chinese drone technology, and how difficult it will be to build a domestic drone industry without key components like magnets. He also outlines what a modern 9/11-style attack might look like, why America still isn’t prepared to defend public spaces from drone terrorism, and the urgent lessons policymakers should take from past failures. The episode wraps with a detour into the NFL: what makes a great owner, why inherited wealth doesn’t equal success, and why both New York football teams continue to puzzle fans and analysts alike.

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Timeline:

(Timestamps may vary based on advertisements)

00:00 Matt Higgins joins the Chuck ToddCast

01:00 Matt’s journey to becoming a “serial entrepreneur”

02:15 There are hurdles, but any American can climb the ladder

03:30 Coming from nothing to finding great success in business

05:00 Do we encourage victimhood by highlighting challenging upbringings

06:15 Some ambitious, successful people need to “chase something”

08:00 Where should government have been more/less involved in your businesses?

09:45 Government’s role should be leveling the playing field with empathy

12:00 America is in the middle of a political realignment

12:45 America needs a “next north star” after winning cold war

13:45 How Matt got started working for Rudy Giuliani

14:45 How did leaving politics change your view of politics?

15:45 There’s a degree of narcissism when you’re in government

16:30 The personalization of the media has politicized it

18:00 Humans are born with original bias, journalists will have it

20:15 There will be implicit bias infused in journalism, but it’s gone too far

22:00 If you spend too much time online it warps your view of reality

23:30 LinkedIn has become a trusted space by not being like Twitter or IG

25:45 Press & comms shops matter more than ever in politics & business

28:30 Drones have completely changed the complexion of modern warfare

29:15 How Matt got into the military drone business

31:00 Everything changed in the drone space after the Ukraine war

32:00 Does automating warfare make killing easier when it looks like a video game?

33:00 The U.S. needs an arsenal of drones it doesn’t currently have

34:15 You can’t make drone motors without magnets & the U.S. doesn’t make them

34:45 Drones are the biggest arms race since nuclear weapons

35:30 A dependency on Chinese drones was created in the U.S.

36:15 Biggest obstacles to building a domestic drone industry

37:30 A modern 9/11 style attack would most likely involve drones

39:00 We haven’t figured out protecting public spaces from drones

41:30 What lessons can we take away from 9/11 for countering drone terrorism?

43:30 What makes a good NFL owner and how much does ownership matter?

45:15 Owners shouldn’t placate media or fans with short term moves

45:45 Why is it so hard to build a winner with the Jets?

48:00 Inherited wealth vs success in business impact on sports owners

49:30 D.C. still isn’t aware of how important the drone arms race is

50:30 America’s enemies are learning how to make drones at scale

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