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Caleb Smith may be the only political operative who's worked for three consecutive US House Speakers. During over a decade on Capitol Hill, he worked with Speakers Boehner, Ryan, and McCarthy. In this conversation, Caleb talks his path to politics from managing a legislative race in small-town Kentucky to working in some of the most prime real estate at the US Capitol building. He goes in-depth on his time on the Hill - being in the early wave of digital political staffers, joining Speaker Boehner's staff, strengths and weaknesses of the last 3 GOP Speakers, witnessing the rise of Trump from within the walls of the GOP establishment, starting Drive Public Affairs, and much more from a participant in some of the most important political moments of the 21st Century.

IN THIS EPISODE

Growing up in Paducah, KY at an important crossroads of American politics...

Why a young Caleb trekked to DC to attend the memorial for Ronald Reagan...

The skill set Caleb picked up managing a motorcycle shop between campaign gigs...

Caleb spends a year working for prominent pollster & focus group maven Frank Luntz...

Caleb manages a winning hometown Kentucky legislative race, the lone D to R legislative flip of the cycle...

Caleb comes to the Hill as a "new media director" among the digital political revolution...

Caleb's first impressions of working for Speaker John Boehner...

Caleb's "GOP House Conference 101" of how House Republicans operate...

The GOP member Caleb describes as a "snake in the grass" (it's not Matt Gaetz)...

What sold John Boehner on embracing digital politics..

John Boehner meets the pope...

Caleb's memories of the chaos during the Boehner to Ryan Speaker transition and why Caleb stuck it out with Ryan...

The "really unpleasant" first interaction Caleb had with Paul Ryan...

Caleb on the unique skill-set that made Paul Ryan an effective House leader...

Being a fly on the wall of the House GOP leadership during the 2015-2016 rise of Donald Trump...

Paul Ryan's immediate Election Night reaction upon Trump's surprise victory...

Inside the development of the 2017 "Trump Tax Cut" bill...

Paul Ryan's reaction when John McCain scuttled Obamacare Repeal...

Caleb's insights into the Donald Trump and Paul Ryan working relationship...

Why Ryan steps down as Speaker and why Caleb stayed with new House GOP Leader Kevin McCarthy...

Caleb on McCarthy's habit of being a "risk taker"...

Inside the toppling of Speaker McCarthy...

Could Patrick McHenry have won the Speaker's Gavel...

Caleb on one of Speaker Pelosi's strongest qualities...

The controversial high-profile House member Caleb believes will be a future GOP Leader...

Junior members Caleb finds especially impressive...

Caleb on the fundamental difference between House Republicans and House Democrats...

Why Caleb started Drive Public Affairs a few months ago...

AND the American Conservative Union, American University, antiquated radio addresses, Sharron Angle, The Better Way Agenda, Stephanie Bice, Kevin Brady, Tim Burchett, George HW Bush, George W. Bush, CPAC, Dave Camp, Joe Cannon, Eric Cantor, The Capitol Rotunda, Centre College, Jason Chaffetz, Michael Cloud, country clubs vs. truck stops, cults of personality, Howard Dean, debating at Oxford, dial tests, Domino's Pizza, fall guys, famous smokers, fiscal cliffs, The Freedom Caucus, Matt Gaetz, Barry Goldwater, Jeb Hensarling, French Hill, Erin Houchin, Jack Kemp, Sue Lowden, Nancy Mace, John McCain, Mark Meadows, Steve Mnuchin, mopeds, Jack Nicklaus, normalizing ideas,  Ralph Norman, Rand Paul, Harry Reid, Marco Rubio, the SALT deduction, Tim S