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!

Catching up this week with return guest David Nir, who for over a decade has been an influential election analyst and the creator of Daily Kos Elections. Within the past week, David has moved his analysis to an independent site - now called The Downballot. In this conversation, David provides an update on his transition: what is happening, why now, and David's long-term goals for The Downballot. Then, stay for my original conversation with David - originally released over three years ago in early 2021. David has a fascinating career arc that charts the rise of the online grassroots from a ramshackle group of political junkies in the early 00s to now being one of the pillars of the political universe.

IN THIS EPISODE…

Why David is launching The Downballot as a new independent, site?

Living through the downturn of the online ad economy...

Long-term goals David has the for The Downballot...

Elected officials who rabid political junkies...

What was David’s first introduction to feminism?

How being the child of a Holocaust survivor has informed who David is…

Why David seeing a Geraldine Ferraro rally in 1984 was an ill omen for the ticket’s chances…

David’s early memories of Rudy Giuliani in NYC politics…

The candidate who taught David to avoid getting too attached to any individual politician…

How David fell in love with down-ballot races…

How David made the decision to forego a legal career to plunge full-time into politics…

How unlikely candidates in Kentucky and South Dakota kicked off the rise of the Democratic netroots…

How an "extra penny" let campaigns know the arrival of the progressive netroots…

Lavishing praise upon the DKE Daily News Digest and Elections Data…

David’s tips for candidates and campaigns who want to connect with the Daily Kos community…

The story of Daily Kos and the rise of Jon Ossoff…

David helps topple the “turncoat” IDC legislative coalition in New York…

What one requirement would have to be part of David’s online dating profile…

AND….

Brendan Boyle, Ben Chandler, Wes Clark, Howard Dean, David Dinkins, John Edwards, Marc Elias, Geraldine Ferraro, Rudy Giuliani, Kaili Joy Gray, Paul Hackett, Karen Handel, Stephanie Herseth, John Kerry, Jeff Klein, John Lewis, Rachel Maddow, Walter Mondale, Markos Moulitsas, Wiley Nickel, Jean Schmidt, Jeff Singer, Elliot Spitzer, Tim Tagaris, Trent Thompson, Elizabeth Warren, Stephen Wolf, AND MORE!

Communications expert Tucker Eskew has been a participant in some of the most seminal moments in American political history over the course of the past 30+ years...a protege of the famed Republican strategist Lee Atwater, senior aide to the Bush 2000 win over John McCain in the fractious South Carolina primary, working in the White House the morning of the 9/11 terrorist attacks, a stint representing the Bush Administration at 10 Downing Street in London, one of Sarah Palin's lead handlers during her whirlwhind 2008 VP experience...among many other momentous experiences during his decades in and around politics. In this conversation, Tucker talks his path to politics and his time as both observer and player in some of the most important moments in recent American history.

IN THIS EPISODE

Tucker's roots as the son of a journalist growing up in the Southeast...

The DC internship that set him on a path toward working in politics...

A couple of his favorite Strom Thurmond stories...

Tucker, in his mid 20s, becomes Press Secretary for South Carolina Governor Caroll Campbell...

Tucker remembers lessons learned from his mentor - the famed GOP operative, Lee Atwater...

Tucker's role on the ground during the bruising, fractious 2000 South Carolina primary between Bush and McCain...

Tucker talks the strategic acumen of Karl Rove...

Tucker's role as a Bush spokesman in West Palm Beach during the 2000 post-election chaos...

Tucker recounts his amazing story of working in the White House on the morning of the 9/11 terrorist attacks...

Tucker works out of 10 Downing Street for months, partnering with British Prime Minister Tony Blair, in the aftermath of 9/11...

Tucker's stint as one of the senior handlers for Sarah Palin during her tumultuous 2008 VP experience...

Why John McCain had a sense of relief after losing the 2008 presidential race...

Lessons learned from 19 years as a partner at the corporate comms firm Vianovo...


AND Whit Ayres, the BBC, Doug Bailey, James Baker, Dan Bartlett, John Buckley, Blaine Bull, Alistair Campbell, Chad Man, Lon Chaney, Dick Cheney, Bill Clinton, the Coalition Information Center, Candy Crowley, Matthew Dowd, emergency bunkers, Ray Eskew, flashbulb moments, fog of war, Gerald Ford, Michael Gerson, the Greenville News-Piedmont, Albert Hawkins, Karen Hughes, Jesse Jackson, Greg Jenkins, Lafayette Square, Jim Lake, Joe Lieberman, Larry Lindsey, low bono, Mary Matalin, Bob McAllister, Anita McBride, Tim McBride, mimeographs, next man up, the News Literacy Project, Richard Nixon, Bob Novak, pocket doors, the Presidential Campaign Hotline, the Reagan/Bush 1984 war room, red light moments, Condaleeza Rice, the Roosevelt Room, Mark Sanford, South Lawn moments, sucker optimists, James Taylor, UPI, The University of the South, ugly babies, George Wallace, Jim Wilkinson & more!

David Callahan is a prolific creator and thinker within Democratic politics. He helped start the progressive think tank Demos in the late 90s, founded the media outlet Inside Philanthropy as a Consumer Reports of sorts into the world of charitable giving, and more recently created Blue Tent - an advisory group to help progressive donors get the most bang for their buck. In this conversation, David talks his early days in politics focused on foreign policy, his next stint as a think-tanker trying to pull the Democratic Party left, and why he's more recently been focused on the world of political giving. David is one of the most informed people on the planet on all facets of the political donor world and provides a tour de force on both the current state of play and future trends to better understand how our politics are funded.

IN THIS EPISODE

Growing up in New York as the child of academics...

An early experience that showed David he was not cut out to be an activist...

A formative year spent at the liberal magazine, The American Prospect...

David talks getting his PhD and his recommendations for those considering academia...

David helps found the progressive think tank Demos and talks the role of think tanks in American politics...

What led David to start Inside Philanthropy, a media outlet dedicated to understanding political fundraising...

The disturbing trend in political giving that led David to start Blue Tent, a resource for progressive donors...

How David and Blue Tent determine where donors will get the most bang for their buck...

Why David is an advocate of giving to organizations instead of candidates...

David on the phenomenon of "rage giving"...

Are donors pulling Democratic candidates to the left?

Has Democratic giving fallen off this cycle?

David's concern about too many advocacy groups and donor fragmentation on the left compared to more unanimity on the right...

David de-mystifies the world of big "donor advisors"...

David on the Soros factor on the left...

The rough balance of spending from the right vs. spending from the left...

The types of operatives who succeed in the donor advising space...

The political novel David wrote in the late 90s that eerily predicted elements of both the 9/11 attacks and the rise of a Donald Trump-like politician...

AND AOC, Stacey Abrams, Miriam Adelson, The American Enterprise Institute, The American Liberties Project, The American Prospect Magazine, Arabella Advisors, Joe Biden, bioethics, Michael Bloomberg, bureaucratic machinations, the Cato Institute, the Center for Voter Information, Bill Clinton, The Committee on States, credential firepower, the DLC, The Democracy Alliance, Michael Dukakis, The Economic Policy Institute, effective altruism, Federalist Society, Marcus Flowers, Focus for Democracy, Fredrick Forsyth, Forward Montana, Give Well, giving circles, Al Gore, Lindsey Graham, Stanley Greenberg, Jamie Harrison, Hastings-on-Hudson, the Heritage Foundation, Hezbollah, Indian Point Power Plant, Indivisible, the Koch Brothers, LUCHA, Mitch McConnell, Amy McGrath, Michigan United, Mind the Gap, Dustin Moskovitz, Movement Voter Project, neoliberal mindsets, The New America Foundation, Paul Nitze, NYPIRG, Beto O'Rourke, Open Markets, RCTs, Ronald Reagan, The Roosevelt Institute, Run for Something, saber-rattling, Sandinistas, Adam Schiff, Star Wars, the States Project, Swing Left, Marjorie Taylor Greene, transactional donors, Way to Win, Working America & more!

Lisa MacLean, founder of Moxie Media - the first female-founded political direct mail firm in the U.S - talks her path to politics...starting in St Louis and then Vassar, to impactful DC internships, managing campaigns in California and eventually starting her own mail firm in the late 1990s that recently celebrated its 25th Anniversary. In this conversation, Lisa talks overcoming adversity as a young woman in politics, the nuts and bolts of how she started her own firm, some of her big races and wins, direct mail best practices and trends, and much more from her 30+ years as a top political operative.

IN THIS EPISODE

Growing up middle-class in the St. Louis suburbs...

The searing experience in 9th grade that drove home the importance of politics...

How the Senate vote to confirm Clarence Thomas changed the course of Lisa's career...

Lisa talks what it was like to go to college at Vassar in the late 80s...

Lessons learned during and after the 1992 "Year of the Woman"...

A personal story Lisa tells about a very difficult experience as a young woman in a media firm...

How Lisa decided to start her own direct mail firm and how she got it off the ground...

The biggests changes in direct mail over Lisa's 25 years in the business...

Some of the memorable races where Lisa feels smart direct mail made a difference...

The direct mail trends Lisa is monitoring...

Lessons Lisa learned in running and growing a successful mail firm over 25 years...

The story behind the name "Moxie Media"...

A glimpse into living in rural, coastal Washington (state)...

AND Jill Alper, Sasha Bruce, Andrea Campbell, Yadira Caraveo, Amy Chapman, Tony Coehlo, Michael Dukakis, free shrimp cocktail, Patty Garamendi, The Good Neighbor News, Lisa Grove, Anita Hill, Trish Hoppey, Mary Hughes, Tishaura Jones, Celinda Lake, Kevin Mack, Hal Malchow, Laurie Moskowitz, Pat Moynihan, Adnaan Muslin, Amy Pritchard, Rich Schlackman, Amy Simon, Heather Stone, Clarence Thomas, tomboys, Henry Underhill, Karen White, the Womens Information Network, Harriett Woods...& more!

Kinky Friedman passed away yesterday, June 27 2024. This is a re-release of a Pro Politics Podcast episode with Kinky originally released June 4, 2021.

Kinky Friedman wore many hats in his 79 years - country music artist, bestselling novelist, political candidate, animal welfare activist, friend of multiple US Presidents, and a Texas and American icon. In this conversation from roughly three years ago, Kinky talks his connections to figures as varied as Nelson Mandela, Adlai Stevenson, John F Kennedy, Barbara Jordan, Bob Dylan, Bill Clinton, George W. Bush among others - and insight into the life of a truly American original.