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 Scott, sloven appearances, The Tonight Show.. & more!

Mark Jablonowski is the President and Chief Tech Officer of DS Political - one of the leading digital ad firms for Democratic campaigns and progressive causes. Mark's roots in campaign tech go back to 2004 and he was deeply involved in the Obama 2008 primary and general election digital innovations. In this conversation, Mark talks his own path to politics starting in Alaska to Maine to the Obama '08 Chicago HQ and continuing to be on the front lines of the digital political evolution. In addition to his own story, Mark gives his takes on digital best practices and trends on subjects as varied as connected television, questions campaigns should ask their digital vendor, the death of the cookie, AI concerns, and much more on an exploding sector within the political world.

IN THIS EPISODE

Mark grows up in Anchorage, Alaska...

Mark is drawn to politics through the 2004 Alaska Senate race...

What it looks like to head up the IT department of a 2004 US Senate race...

Mark's early tech interest and building his own computer as a teenager...

How Mark connects with the 2008 Obama primary campaign...working from NH to TX to PA to IN to Chicago HQ...

Working as Obama 2008 "IT Special Projects Director" and the tech innovations of the '08 Obama team...

How Mark became President of the large digital firm, DSPolitical...

Mark's take on the common threads of what makes for a successful digital political firm...

The initiative of DS Political offering free digital ad inventory to down-ballot campaigns...

Mark's best practices on how campaigns should think about digital advertising...

The importance of "connected televisions" and being on "the biggest screen in the house"...

Misconceptions and unnecessary mistakes in the world of digital advertising...

Differences in Democratic vs. Republican digital approaches...

Insights into voters' digital habits and where to have the most impact...

The end of digital cookies which is changing the way digital politics operates...

Mark's concern about AI creating massive misinformation in digital ads...

The right type of people to succeed in digital politics...

Bryan Bennett is the Senior Director for Polling & Analytics at The Hub Project and a pollster for Navigator Research who recently spearheaded a 4,000 sample survey among voters 18-34. In this conversation, Bryan talks his path to politics and polling and goes deep on this new massive project among younger Americans. This data unearths new findings on how and where younger voters get their news, views toward both parties and policy priorities, gauging the presidential race both before and after the Biden transition to Harris, comparing 5 different polling methodologies to reach voters, and much more from this massive new trove of polling data among younger Americans.

IN THIS EPISODE

Bryan's roots outside of Austin, TX and how the 2000 election and Iraq War drew him to politics...

Why Bryan gravitated toward polling and his insight as to what makes for an effective political pollster...

How Bryan came to Navigator Research, and its mission in the public opinion sphere...

Some of the influential work Navigator Research has done over the past few years...

The origin of Navigator's project of a 4,000 sample poll of voters under age 35...

The seeming disconnect among younger voters between partisanship and policy preferences...

What Bryan learned by testing 5 different polling methodologies among younger voters...

What is unique about economic sentiments among younger voters...

Some of the most surprising findings in this trove of data...

What this data reveals about how and where younger voters get their news...

What the data showed about a Biden vs. Trump re-match and how it's different with Kamala Harris atop the Democratic ticket...

The set of issues younger voters most prioritize...

The potential for 2024 polling error among younger voters that Bryan is monitoring...

What recent Battleground polling reveals about the 2024 presidential race...

Upcoming Navigator Research projects Bryan is most excited about...

Bryan details the best way to enjoy a few days in Austin, TX...& much more!