05 Matt Lewis – Trailblazer, Pundit and Prolific Writer

Matt Lewis is a college graduate with a political science degree, author, CNN contributor and my colleague at The Daily Caller. In this episode I talk with Matt about career trajectory, his success story, this election cycle, becoming a pundit in political journalism, his struggles to get where he is today, choosing the right career path and of course, politics.

Matt’s book Too Dumb to Fail, was written pre-Trump nomination, and sets the bar for explaining where the Republican party stands. This book hits the nail on the head on the state of the Republican party and of the Conservative Movement.

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Show Notes: 

  • Farming, rednecks and rural Maryland
  • Matt’s father’s influence on his political career
  • The focus of Matt’s writing for the last 5 years
  • Why Trump will probably do well in Maryland
  • Matt’s manager role at Roy Rogers fast food restaurant chain
  • The only networking book you’ll ever need
  • Why you should quit a job that isn’t fulfilling
  • Hitting rock bottom and the courage born from desperation
  • Don’t be afraid to quit a job
  • The disenchanting nature of losing a campaign
  • Making the move from political consultant to political journalism
  • How blogging and the internet reinvented Matt’s career
  • Blogging as a volunteer for Human Events online
  • Politics Daily
  • From cable TV show on Tucker to working for Tucker Carlson at The Daily Caller
  • The transition from cut throat television to a prolific writer
  • How TV can make you narcissistic and neurotic if you are not careful
  • Why Matt started hosting his own podcast
  • Advice for the next great pundit or contributor to CNN
  • Why Trump still has a good chance of winning the electoral college
  • Why Matt may not vote in the 2016 presidential election
  • Matt tells the story of his first interaction with Donald Trump
  • Why Trump is the perfect storm
  • What if Mitt Romney decided to run in May as a third party candidate?
  • Matt’s support of Rand Paul
  • If Trump looses what will happen to the Republican party?
  • How opposing Trump is bad for one’s career in conservative commentary
  • Admired historical leaders
  • Which 3 books have most shaped Matt’s world views
  • What Matt believes that no-one else believes
  • What does Matt hope he will be remembered for?

Two turning points in Matt’s life:

  1. 1998 Becoming a professional campaign manager for the Maryland State Senate Campaign
  2. 1999 Interning and working at The Leadership Institute

Links Mentioned:

Facebook | Twitter | The Daily Caller | Roll Call | Podcast


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  • Written by Jamie Weinstein