American politics has changed dramatically over the past two decades. The rise of podcasts, digital media, and independent content creators has transformed how people consume political news and engage with current events.
Few people have played a bigger role in that shift than Jon Favreau, a former White House speechwriter, who helped build one of the most influential political media companies in the country. That’s exactly why Lauryn and Michael invited Jon onto The Bossticks.
He has experience with both the inner workings of the White House and the rise of modern political media. This gives Jon a unique perspective on how politics, news, and public discourse have evolved over the years. In the conversation, he discusses his time working for President Obama, the creation of Crooked Media, and how podcasting changed the way millions of Americans engage with politics. You can listen to the entire Jon Favreau podcast with The Bossticks below. But for now, we’ll cover some of the highlights below.
Who Is Jon Favreau of Crooked Media? From Politics to Podcasts
Jon Favreau is an American political commentator, co-founder of Crooked Media, podcast host, and former White House speechwriter. Before moving into media, Jon served as Director of Speechwriting for Barack Obama. Though he was the youngest person to ever hold this role at just 27 years old, he helped craft some of President Obama’s most memorable speeches. This includes the 2009 inauguration address and the 2011 Tucson memorial speech.
After leaving the White House in 2016, Jon and several fellow Obama administration alumni launched Crooked Media. They pioneered the company to provide political news, commentary, and civic engagement through podcasts and digital media rather than traditional cable networks. Through the brand, Jon and his colleagues produce one of the most influential political podcasts in the United States, Pod Save America.
Today, Jon continues to host podcasts, analyze current events, and engage audiences in political discussions. He currently lives in Los Angeles, home to Crooked Media’s headquarters, with his wife, Emily Black, and their two sons, Charlie and Teddy. Though he no longer works directly in government, he remains one of the most recognizable voices in modern political media.
What Did Jon Favreau Do in the Obama Administration?
As you’d imagine, holding the title of Assistant to the President comes with plenty of responsibilities. For example, while working under the Obama administration, Jon Favreau:
- Served as Director of Speechwriting in the Obama White House
- Wrote and edited major presidential addresses, including policy speeches and public remarks
- Helped shape the administration’s messaging on key national issues
- Worked closely with senior advisors, including David Axelrod, on communications strategy and political messaging
- Served as a member of the White House’s core communications team
Jon Favreau Career Timeline
Jon Favreau’s trajectory to the White House, while certainly career-defining, wasn’t directly intentional. His interests originally fluctuated among writing, becoming a lawyer, entering journalism, and pursuing public service. However, after meeting President Barack Obama in 2004, the two quickly bonded, sparking Jon’s interest in future political work.
As a result, Jon Favreau’s career timeline looks a little like this:
- Early 2000s: Began his career in political communications and speechwriting after graduating from college
- 2005: Joined Senator Barack Obama’s team as a speechwriter
- 2008: Worked on Obama’s presidential campaign, helping craft speeches and campaign messaging
- 2009: Appointed Director of Speechwriting in the Obama White House
- 2009–2013: Led speechwriting efforts for major presidential addresses, policy speeches, and public communications
- 2013: Left the White House and transitioned into political commentary and media work.
- 2017: Co-founded Crooked Media alongside fellow Obama aides and alumni
- 2017–Present: Co-hosts Pod Save America and helps expand Crooked Media into a leading political podcast network
- 2024: Wrote and published his New York Times Bestselling book, Democracy or Else: How to Save America in 10 Easy Steps
- Present Day: Continues working as a podcast host, media executive, political commentator, and author
What Is Crooked Media?
Crooked Media is a political media company founded in 2017 by former Obama administration staffers John Favreau (speechwriter), Jon Lovett (speechwriter), and Tommy Vietor (national spokesman). The whole idea was to reconnect the public to politics. They saw cable network news as overly serious, scripted, and completely out of touch with real people. Crooked Media set out to make politics more authentic and accessible by delivering conversations, analysis, and news through non-traditional channels—meaning podcasts, youtube channels, live shows, and in-person events.
Best Podcasts From Crooked Media
- Pod Save America: U.S. politics and elections, hosted by Jon Favreau, Jon Lovett, Tommy Vietor, and Dan Pfeiffer
- Pod Save the World: Foreign policy and international affairs, hosted by Tommy Vietor and Ben Rhodes
- Offline with Jon Favreau: Technology, media, internet culture, and democracy
- Lovett or Leave It: Political comedy and current events, hosted by Jon Lovett
- What A Day: Daily news and political analysis, hosted by Jane Coaston and Tre’vell Anderson
- Strict Scrutiny: Supreme Court and legal analysis, hosted by Leah Litman, Melissa Murray, and Kate Shaw
- Keep It: Entertainment, pop culture, and media commentary, hosted by Ira Madison III, Louis Virtel, and Aida Osman
- Pod Save the UK: British politics and current affairs, hosted by Nish Kumar and Coco Khan
- Hysteria: Politics, culture, and current events from a woman’s perspective, hosted by Erin Ryan and Alyssa Mastromonaco
- Pod Save the People: Race, justice, activism, and social issues, hosted by DeRay McKesson
How Jon Favreau Influences Modern Political Media
Popularized Podcast-First Progressive Political Commentary
During the 2016 election, Jon Favreau, Jon Lovett, Tommy Vietor, and Dan Pfeiffer launched Keeping It 1600 (referencing the White House’s address). The show gave listeners one of the first behind-the-scenes looks at campaigns, political strategy, media coverage, and current events from the perspective of former Obama administration insiders.
The podcast quickly gained a large audience and demonstrated significant demand for political content outside traditional cable news. At the time, conservative commentators like Glenn Beck, Steven Crowder, and Ben Shapiro had already built large audiences through podcasts, online media, and digital platforms. So, Keeping It 1600 gave progressive voters similar access to long-form political conversations and insider perspectives.
After the election, the group decided to continue and expand the concept. They rebranded the show as Pod Save America and launched Crooked Media. Together, they helped popularize podcast-first political commentary, proving that long-form, on-demand conversations could become a major source of political news and analysis for millions of Americans.
Shifted Political Discussion Beyond Cable News
Through Pod Save America and other Crooked Media shows, Jon Favreau helped popularize a different style of political interview. More specifically, he didn’t rely on short television segments or sound bites. Instead, he created a platform where politicians, journalists, activists, and policy experts could have in-depth conversations about complex issues.
Over the years, the podcast has featured presidential candidates, elected officials, campaign strategists, and influential public figures. These longer discussions gave audiences greater insight into how political decisions are made and helped make policy conversations more accessible to everyday listeners. In doing so, Jon helped establish podcasts as a major venue for political interviews and public discourse.
Want to learn more? Here’s Jon Favreau discussing podcasting vs. cable news with The Bossticks.
Leveraged Government Experience for Analysis
A lot of people who talk about politics either have never worked in government or are speaking on behalf of a political campaign, an elected official, or a media organization. Jon Favreau and his colleagues at Crooked Media are different.
After years of working alongside senior advisors, campaign strategists, communications teams, and policymakers, they have plenty of firsthand experience. They’re able to discuss how campaigns operate, how political messaging is crafted, and how major decisions are made behind the scenes.
Because they no longer work for the government, Favreau and his co-hosts can discuss those processes from an independent perspective. Rather than simply reporting on political events, they often explain the strategy, communications, and decision-making that shaped them. This insider context has helped audiences better understand not just what is happening in politics, but why it is happening.
Built a New Model for Political Media
Before Crooked Media, television networks, newspapers, and established news organizations dominated political media. Favreau and his co-founders proved that they could build a successful political media company around podcasts, digital content, live events, newsletters, and direct audience engagement.
As Crooked Media grew, it inspired journalists, commentators, campaign veterans, and public figures to launch their own independent media ventures. Through that success, Favreau helped reshape how audiences consume political content and how creators distribute it in the digital age.
Want to learn about another political innovator who took the digital world by storm? Listen to The Bossticks episode “Is it Still Okay to Have Conversations in the USA?”
Is Jon Favreau Still Involved in Politics?
Yes, Jon Favreau is still involved in politics, but he is no longer a government official. Instead, he focuses on political commentary, civic engagement, and public education through Crooked Media. As the co-host of Pod Save America, he regularly discusses elections, conducts interviews, analyzes political decisions, and communicates current events to millions of listeners.
While Favreau no longer works in government, he continues to influence political conversations through his podcasts, media appearances, and advocacy efforts. His role today is less about shaping policy directly and more about helping people understand and engage with the political process.
Inspired by his level of dedication? You can learn even more about this in our post, “Crushing It: How Great Entrepreneurs Build Their Business and Influence—and How You Can, Too.”
Jon Favreau knows how people really want to engage in politics.
Jon Favreau’s career proves that influence doesn’t always come from holding office. From writing speeches in the White House to building one of the most successful political media companies in the country, he has spent nearly two decades helping shape how Americans engage with politics. Whether you agree with his views or not, there’s no denying the impact he’s had on modern political media and the rise of podcast-first news and commentary.