Michael: Here’s a wild thought: the most important skill for a White House Communications Director might not be spinning the press, but knowing how to hide a giant rip in your pants from the President of the United States. Kevin: Wait, what? That sounds like a nightmare scenario from a sitcom, not the West Wing. Please tell me that’s a real story. Michael: It’s absolutely real, and it’s a perfect window into the high-stakes, high-absurdity world we're discussing today. That story comes directly from Daniel Pfeiffer's book, Yes We (Still) Can: Politics in the Age of Obama, Trump, and Twitter. Kevin: Ah, Dan Pfeiffer. I know him from his podcast. He always has that very direct, no-nonsense vibe. Michael: Exactly. And he wasn't just some staffer; he was one of Obama’s earliest hires and eventually his Communications Director. What's fascinating is that he wrote this after leaving the White House and co-founding the massively popular podcast Pod Save America. So the book has this very urgent, conversational tone, like he's trying to figure it all out right alongside the reader. Kevin: Right, it's not a dry political memoir. It's got a pulse. And it was highly rated by readers, though many pointed out how emotionally tough it was to relive the 2016 parts. It feels very personal. Michael: It is. But before we get to the White House chaos and the ripped pants, the book starts somewhere else entirely. It starts with an idea so audacious it changed modern politics: the campaign as a tech start-up.

Kevin: Okay, I’ve heard this comparison before. Obama's 2008 campaign as a "start-up." It sounds like a cool buzzword, but what did that actually mean in practice? Weren't they just running a campaign like everyone else, just with a better candidate? Michael: That’s the brilliant question, because it wasn't just a buzzword. Pfeiffer reveals that Obama himself, years later, told a room full of Silicon Valley executives that his 2008 campaign "might have been the greatest start-up in history." And Pfeiffer breaks it down into five building blocks, just like a business plan: attitude, scaling, culture, strategy, and branding. Kevin: I’m interested in the "attitude" part. What was so different? Michael: The attitude was a complete rejection of political fear. Pfeiffer tells this amazing story about his first real meeting with Obama. He’s a seasoned operative, used to the brutal, cynical world of politics. He’s skeptical. But Obama says to him, "I have a great life. I don’t need this, and if I lose, I will just go back to my life in Chicago." Kevin: Wow. That’s a huge psychological advantage. He wasn't desperate. Michael: Precisely. That lack of desperation, that comfort with the possibility of losing, became the campaign's secret weapon. It allowed them to take huge risks. Their internal motto was basically "WTF"—as in, "Why not try it?" This wasn't a cautious, play-it-safe operation. It was an insurgency. And they had to be, because they were up against the Clinton machine, which was the political equivalent of Microsoft in the 90s. Kevin: So that explains the risk-taking. But what about the scaling? A start-up that grows too fast can implode. How did they handle the explosion of interest in Obama? Michael: With barely-controlled chaos. Pfeiffer paints this hilarious and terrifying picture of the campaign's official launch. They had almost no infrastructure. On the day they announced Obama's exploratory committee, key staff got locked out of their own Senate office. Their temporary headquarters didn't have internet, so a staffer named Nick Shapiro had to wake up at 5 a.m. every day, go to a nearby hotel lobby, and steal their Wi-Fi to send out the morning press releases. Kevin: You're kidding. A presidential campaign was being run on stolen hotel Wi-Fi? Michael: It’s the perfect start-up story! The campaign manager, David Plouffe, described it as "bolting the wings on the plane as it took off." The demand was astronomical. Their first rally at George Mason University was so mobbed they completely lost control of the crowd. They were building the organization in real-time while trying to manage a phenomenon. Kevin: That sounds incredibly stressful. Which brings me to the culture. Pfeiffer mentions a "no assholes" rule. In the high-stress, ego-driven world of a presidential campaign, how on earth do you actually enforce that? It sounds idealistic. Michael: It flowed directly from the top. Obama was famous for his "No Drama Obama" persona, and the campaign culture was a direct reflection of that. It wasn't just a nice-to-have slogan; it was a core operating principle. Plouffe and other leaders actively hired for it and fired people who violated it. They wanted loyalty and commitment, not backstabbing and leaks, which had plagued so many previous Democratic campaigns. Kevin: So it created a sense of trust. Michael: A huge sense of trust. It meant people could focus on the work instead of watching their backs. This culture, combined with a crystal-clear strategy—focus on the caucus states, win Iowa, and build momentum—and a brand that was authentic to the candidate, "Change We Can Believe In," created a machine that the Clinton campaign simply couldn't compete with. It wasn't just a better message; it was a better-run company.

Michael: That "no drama" start-up culture was essential for winning the campaign. But keeping it alive inside the White House, when you're facing a media that is actively, commercially incentivized to create drama, is a whole different war. That's where the book's tone really shifts. Kevin: Yeah, this is where it gets darker. Pfeiffer calls it the "New Media Wasteland." What was the biggest shock for him, moving from the campaign trail to the White House press room? Michael: The power dynamics. He tells this story from the very first week. Obama, fresh off his victory, decides to make a surprise visit to the White House press briefing room, just to say hello. His staff, including Rahm Emanuel, are horrified. They know it's a bad idea. Kevin: Why? He’s the president, it’s his house. Michael: That's what Obama thought. But the moment he walked in, the press corps didn't see a friendly greeting. They saw an opportunity. They started shouting aggressive questions, turning it into a hostile press conference. Obama beat a hasty retreat. The lesson was immediate and brutal: the briefing room wasn't his turf. It was the press's turf, and they made the rules. Kevin: That’s a stark realization. And that was with the traditional press. The book gets much more intense when it talks about the rise of what Pfeiffer calls "fake news." Michael: It does. And he argues this wasn't a Trump phenomenon. It was an Obama-era problem that Trump later perfected. The case study that defines this is the "death panel" conspiracy. Kevin: Ugh, I remember this. The claim that Obamacare would have panels of bureaucrats deciding if your grandma gets to live. It sounds insane now. How did that even start? Michael: It started with a single Facebook post by Sarah Palin in the summer of 2009. She claimed the Affordable Care Act would create "death panels" to ration care. It was a complete fabrication, based on a willful misreading of a provision about voluntary end-of-life counseling. But it was a potent, terrifying lie. Kevin: And Fox News just ran with it. Michael: They put it on a rocket. Republican leaders like Chuck Grassley and John Boehner repeated it. It dominated town halls. It created a genuine panic. The White House was in a communications crisis, trying to fight a lie that was more emotionally compelling than the truth. Kevin: This is the part that readers found so infuriating. Why couldn't they just kill that lie with facts? It seems so obviously false. Michael: Because the rules of the game had changed. Pfeiffer argues that the "presidential bully pulpit"—the idea that a president can command the nation's attention and set the record straight—was dead. Trust in mainstream media was collapsing. And new platforms, especially Facebook, were creating partisan echo chambers where these lies could circulate endlessly, reinforced by friends and family. Kevin: So facts were irrelevant. Michael: Worse than irrelevant. The fight itself became the story. And here's the truly chilling data point Pfeiffer shares: six years after the law passed, a survey found that nearly 30% of voters—almost all Republicans—still believed the ACA included death panels. The lie had become a permanent feature of their reality.

Kevin: So if facts don't work and the media landscape is a "wasteland," what's the answer? Does the book just end on a note of despair? It sounds like an impossible situation. Michael: Not at all. And that's why the title, Yes We (Still) Can, is so deliberate. It’s a direct rebuttal to the despair. Pfeiffer's diagnosis is grim, but his prescription is pragmatic. He argues that the Republican party became radicalized by its own media ecosystem, which created the perfect environment for Donald Trump. Kevin: He makes the case that Trump was a symptom, not the disease. Michael: Exactly. The disease was a political party that had decided its only organizing principle was total, absolute opposition to Barack Obama. Pfeiffer tells this incredible, damning story about how, after the 2010 midterms, the White House invited the Republican leadership—Boehner, McConnell—to dinner to find common ground. Kevin: And they refused? Michael: They refused because they were afraid of being photographed breaking bread with Obama. They feared their own base, which had been whipped into a frenzy by right-wing media, would see it as a betrayal. When your opposition won't even have a meal with you for political reasons, bipartisanship is dead. Kevin: So the prescription can't be "reach across the aisle" and "go high when they go low," can it? That sounds like bringing a policy paper to a knife fight. Michael: That's the core of his argument for the future. He says Democrats can't and shouldn't adopt the lying and cynicism of the modern GOP. But they can't be naive, either. They have to fight back, but by being smarter, more organized, and more aggressive in telling their own story. Kevin: What does that look like in practice? Michael: The key, he argues, is building a robust, progressive media ecosystem. This is the big takeaway. It's not about creating a "liberal Fox News" that spews its own propaganda. It's about investing in and building platforms—podcasts, digital media sites, YouTube channels—that can bypass the biased gatekeepers, speak directly to people, and win the daily battle for the narrative on social media. Kevin: So it’s about creating an alternative to the poisoned well. Michael: Precisely. It's about recognizing that the media environment of the 20th century is gone forever. You can't rely on the New York Times to fairly adjudicate your argument anymore. You have to build your own megaphone.

Michael: Ultimately, the book is a journey. It takes you from the peak of "Hope and Change" in 2008, through the brutal trench warfare of governing, to the shocking reality of 2016. It’s a powerful warning that a great message and a great candidate are not enough if the information ecosystem itself is poisoned. Kevin: And it's a call to action, isn't it? It's not just a history lesson. It's about taking responsibility for the information we consume and create. The book ends on a surprisingly hopeful note, echoing a quote from Obama himself. Michael: It does. Obama talks about his hope that a new generation of young people, who grew up online and are more skeptical of misinformation, will get involved and create a "cleansing wave" that washes over the country. Kevin: It leaves you with a question, really. It’s not a neat and tidy answer. It’s a challenge. Michael: Exactly. The book lays out the whole story, the good, the bad, and the ugly, and then it turns to the reader and essentially asks: Now that you know how the game is played, what are you going to do about it? Kevin: A powerful place to end. This is Aibrary, signing off.