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Picture this: You're at an inaugural ball in your tuxedo when your BlackBerry buzzes with a message telling you to pick up a mysterious package from a random DC address. Sounds like something out of a spy thriller, right? For Ian Bassin, this was just the beginning of a journey that would teach him everything about building organizational culture, scaling across political differences, and leading through uncertainty.
Key Takeaways
- Intentional culture must be baked into an organization's DNA from day one, not treated as an afterthought or wall decoration
- Distributed organizations can actually strengthen culture and efficiency when managed with deliberate systems and processes
- Building across political divides requires shared foundational values while respecting legitimate policy differences
- The "2% principle" suggests leaders can maintain hope and momentum even when success seems unlikely
- "Coopertition" in nonprofit spaces balances necessary collaboration with healthy competition that drives innovation
- Taking charge early in your career means acting like you belong, not waiting for permission to lead
- Mission-driven organizations need clear decision frameworks that prioritize impact over personal advancement or external validation
- Remote work requires hyper-intentional relationship building through structured onboarding and genuine personal connections
The Accidental Path to Democracy Protection
Sometimes the most important work comes from the most unlikely beginnings. Bassin's story starts not with grand political ambitions, but with a moment of clarity at a dingy music club at 5 PM on a Wednesday. He was there covering a band for a small music magazine when he looked around and saw himself decades in the future - just him, the band's girlfriends, and one old guy at the bar who looked like Keith Richards.
"I went home and said to my roommate, 'I think I'm going to go to law school,'" Bassin recalls. That night, he applied.
What's fascinating here is how career pivots often happen not through careful planning, but through moments of honest self-reflection. Bassin had initially planned to be a journalist after covering the NATO bombing in Kosovo, but that Wednesday evening revelation changed everything. Sometimes you need to see your future clearly to realize it's not the future you want.
The path from music journalism to democracy protection wasn't linear, but it was guided by early experiences with civic engagement. Back in college around 1994, Bassin organized across campuses to fight proposed cuts to federal student aid. The experience gave him what he calls "the bug" - that intoxicating realization that citizens can actually shape their country's future.
Here's what's interesting about that early organizing experience: It wasn't abstract policy work. Bassin had skin in the game - he benefited from student loans himself, and his younger brother's future education depended on those programs continuing. The best advocacy often comes from personal stakes, not ideological purity.
The White House Binders That Changed Everything
After law school at George Washington University, a series of fortunate connections led Bassin to Barack Obama's Senate campaign, then to the Obama transition team, and finally to a last-minute Hail Mary email that landed him a job in the White House counsel's office. But it was what happened on inauguration night that really shaped his understanding of how institutions work.
That mysterious package pickup? It contained three thick binders full of memos dating back to the Eisenhower Administration - essentially the unofficial rulebook for how White House staff should conduct themselves. What struck Bassin wasn't just the content, but the continuity across administrations.
"A lot of these rules are not legally binding," he explains. "They were just traditions, customs that were passed down from administration to administration." When questions arose, he'd consult the binders. If those didn't have answers, he'd call his predecessor from the Bush administration. If they couldn't figure it out together, they'd call the person who did the job under Clinton.
Think about that for a moment. Here were people who had worked for presidents of different parties, with fundamentally different philosophies about government's role, yet they maintained consistent standards about how to exercise power responsibly. The rules transcended partisan politics because everyone understood they were temporary stewards of something larger than themselves.
This experience became crucial to Bassin's later work because it showed him both the strength and fragility of democratic norms. These weren't laws enforced by courts - they were shared understandings that held only as long as people chose to honor them. What happens when someone decides those traditions are "for suckers"?
Building Culture From Day One: The DNA Approach
After his White House stint, Bassin worked for two different nonprofits that taught him contrasting lessons about organizational culture. The first, called Avaaz, was led by what he describes as "a management savant" who built culture into everything from hiring processes to daily team meetings. The culture wasn't just articulated - it was lived and breathed throughout the organization.
The second organization had values posted on their website and wall, but when Bassin would tap colleagues on the shoulder and ask them to recite the organization's principles, they couldn't do it. Even worse, they never invoked those values in their actual work decisions.
"It was like a human A/B test," Bassin says. "I was in two different organizations seeing what it was like to do intentional culture and seeing what it was like to put culture principles on the wall."
When he and Justin Florence decided to start Protect Democracy after the 2016 election, Bassin insisted they write out their culture principles alongside their concept note. Florence initially questioned this priority, but Bassin knew from experience that culture had to be baked into the organization's DNA from the beginning.
Their first principle: "Mission is the metric." Every decision gets filtered through a simple question: What best advances our mission of preventing American democracy from declining into authoritarianism? This sounds obvious, but Bassin notes how many organizational decisions actually get influenced by considerations like media coverage, investor opinions, or personal career advancement.
Another core principle: "Work-life balance is a professional responsibility." This wasn't feel-good rhetoric - it was based on social science showing that overworked staff are less innovative, more mistake-prone, and more likely to burn out. In a city like Washington where 14-hour days are worn as badges of honor, this principle required swimming against the dominant culture.
Why They Built a Distributed Organization Before It Was Cool
Years before COVID made remote work mainstream, Protect Democracy made a deliberate choice to build as a distributed organization rather than establishing a traditional headquarters. This decision came from both mission-specific and generally applicable reasons.
The mission-specific rationale was straightforward: They didn't want to be another DC-centric organization. "American democracy doesn't just exist in Washington DC," Bassin explains. "That's part of the problem. It exists all over the country." They needed wisdom from the full nation, not just the Beltway bubble.
But the broader organizational benefits were equally compelling. Distributed organizations offer better access to talent, since skilled people live everywhere. They also provide more control over work efficiency and culture. In a physical office, someone might interrupt your flow state because they want to chat right when you need to focus. Remote work allows people to optimize their own productivity rhythms.
However, Bassin acknowledges the real challenges of remote culture, particularly around mentorship and learning. "You have to do all those things, but you do them all super intentionally," he says. "You're able to craft intentional spaces to do all of those things."
For Protect Democracy, this means intensive onboarding bootcamps for new cohorts, followed by one-on-one meetings with everyone in the organization. But here's the key instruction for these meetings: Don't share your resume (people can read that online) or talk about current projects. Instead, have the courage to ask, "What makes you tick?"
This approach builds the deep rapport and trust necessary for a distributed team to function during high-stress moments. When someone says something that could be misinterpreted in a heated discussion, their colleagues give them the benefit of the doubt because they know them as full human beings, not just professional personas.
The Art of Working Across Political Divides
Perhaps Protect Democracy's most impressive achievement is assembling a team that includes people who've worked for everyone from Elizabeth Warren to Ted Cruz, from Jim DeMint to John McCain. How do you create shared purpose among people with such different political philosophies?
The answer starts with distinguishing between legitimate policy disagreements and fundamental democratic values. "We're able to bring people together who disagree, but we agree on the fundamental values of democracy," Bassin explains.
He points to Russia as a stark example: When opposition leader Alexei Navalny was killed, people weren't even allowed to lay flowers in public mourning without being brutally arrested. That crosses the baseline of what's required for healthy democracy, regardless of where you stand on tax policy or healthcare.
Building this kind of coalition requires what Bassin calls "a culture of curiosity and a culture of cherishing feedback and a culture of humility and being willing to learn and listen to one another." It's not about avoiding political differences, but about maintaining respect for people who hold different views within the bounds of democratic norms.
This approach offers lessons for any organization trying to bridge divides. Focus on shared foundational values rather than specific policy positions. Create space for genuine curiosity about different perspectives. And remember that unity doesn't require uniformity - it requires mutual respect and shared commitment to the process of working through differences democratically.
Coopertition: Competing and Cooperating Simultaneously
One of Bassin's most interesting insights involves what he calls "coopertition" - the unique dynamic in nonprofit work where organizations must both compete and cooperate with similar entities.
In the for-profit world, competition is assumed and celebrated because it drives innovation and progress. In the nonprofit sector, donors often ask why organizations can't just merge and eliminate "duplication." But Bassin argues this misses the point.
"You do want us to cooperate with each other," he says. "If we develop an innovative strategy to advance the ball of our democracy, we should share it with the entire sector." But collapsing all similar organizations would eliminate the healthy competition that drives innovation and improvement.
The reality is that nonprofit organizations compete for donors, talent, media attention, and meetings with legislators. This competition makes them better. "That drives us to do better," Bassin acknowledges. The key is balancing this competitive drive with genuine collaboration where it serves the shared mission.
Leading Through Uncertainty: The 2% Principle
Perhaps the most powerful leadership lesson from Bassin's story comes from a moment of deep doubt in fall 2020. As an self-described optimist, he had dipped into thinking there was only a 49% chance that American democracy would end up in a better place - meaning it was more likely than not that the country would slide into authoritarianism.
He called a mentor for advice on how to lead a team from a place of pessimism. The mentor's response was brilliant: "You may think there's only a 49% chance of success, but do you believe that you and your team and the American people have the agency to add that 2% to tip us back to 51%?"
This became Bassin's framework for leadership during uncertain times. You don't need to believe success is guaranteed - you just need to believe you can tip the scales enough to make success more likely than failure. That 2% represents human agency, the capacity to influence outcomes through intentional action.
"Authoritarianism thrives on hopelessness, on despair, on a feeling of isolation and that nothing can possibly get better," Bassin explains. "Democracy as a form of government isn't just a set of laws or amendments in a constitution... it is that belief that we have the agency to chart our own future."
This principle extends far beyond politics. Any leader facing long odds can ask themselves: Do we have the agency to improve our chances by just enough to tip the balance? That question can restore hope and momentum even in the darkest moments.
Early Career Lessons: Acting Like You Belong
Bassin shares a crucial early career insight from his White House days. As a young lawyer, he initially tried to learn by sitting in the back of meetings, literally choosing seats "on the furthest outskirts of the room, right against the wall, not at the center table."
Meanwhile, his colleagues Karen Dunn and Danielle Gray, who were the same level of experience, would walk into rooms and sit at the head of the table. The difference in how people treated them was stark.
"If you behave like a wallflower, people will treat you like one," Bassin realized. His colleagues weren't arrogant or power-hungry - they just acted like they belonged, and others responded accordingly.
This lesson came full circle when Bassin got the call to lead Protect Democracy. Instead of his usual tentative approach, he told himself: "When you get on that call, you take charge, you sit at the head of the room and you tell everyone what we're going to do. You listen, but you definitely lead."
For young professionals, this insight is gold. Competence matters, but so does confidence. Acting like you belong at the table often becomes a self-fulfilling prophecy.
The story of Protect Democracy offers a masterclass in building mission-driven organizations that can operate across traditional divides. From intentional culture design to distributed team management to coalition building across political differences, Bassin's approach demonstrates that principled leadership can bridge seemingly impossible gaps. Most importantly, it shows that even when facing long odds, believing in your agency to tip the scales can make all the difference between success and failure.
