Leading across great divides: Ian Bassin, Protect Democracy Executive Director

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1:18The night of January 19th, of course, is the famous inaugural balls.

1:27There are a bunch of inaugural balls around D.C., and so I get my tuxedo on, go to an inaugural ball, and I get a message, probably a BlackBerry message, saying, go to this random address in D.C. and pick up a package.

1:44That's Ian Bassin, lawyer, activist, and executive director of Protect Democracy. Ian is taking us back to January 19th, 2009, the night before the historic inauguration of President Barack Obama. Ian is joining the administration as an associate White House counsel. His job? Ensuring the ethics and proper rules of governance. Basically, one of the people who keeps our democracy functioning as a democracy. So I duck out of the ball. It's raining that night. I run across the district in the rain, and I get to the building. There's a doorman who hands me a plastic grocery bag bursting at the seams with three thick binders, like school binders, right?

2:27And it's got my name on the outside of the bag. This sounds like this may be a foreign operation. Totally, right? Like, it's like, you're looking for Jason Bourne, not me, right? And I bring them home that night and open these binders to look at what they were. and they contained memos going back to the Eisenhower administration that White House counsels and chiefs of staff had sent to White House staff and executive branch officials explaining the rules, explaining what people were allowed to do and were not allowed to do in the performance of their duties. And what was striking about it and became so clear over the next three years where these binders became my Bible was that a lot of these rules were not legally binding.

3:07They were just traditions. They were customs that were passed down from administration to administration. And when people in the White House had questions about what was allowed, I'd consult the binders. And if they didn't contain the answer, I called Emmett Flood, who did my job for President Bush. And if Emmett and I couldn't answer it, we called Beth Nolan, who did it for President Clinton. And it didn't matter whether we were working for a Democratic president or a Republican president. The rules were consistent for over decades. The handoff sounds kind of crazy, right? There's no three-hour sit-down and a walkthrough and let me help you understand how this works, etc.

3:39It's in the dark and stormy night. You're being handed a grocery bag full of binders. I mean, why aren't these things codified, and why isn't the process more formalized? So I didn't understand quite why that was the handoff at the time, and I've come to understand it since. So I bring these binders in with me on noon on January 20th of 2009. And then I served for about three years, almost three years. I left the fall of 2011, and I left the binders for my successor so that my successor could use them. Well, flash forward to November of 2016, Donald Trump was elected. And I was concerned about, well, what's going to happen to these binders?

4:15And the incoming political movement that has essentially been organized in opposition to customs, traditions, norms like that might disregard them entirely. And so I reached out to the White House Counsel's office at the end of the Obama administration. I said, hey, I know that you need to keep a copy of those binders because they are a presidential record under a federal law known as the Presidential Records Act. But the physical copies that you have were mine. I brought them into the administration with me. I carried them into the building on January 20, 2009. I'd like them back. But ultimately, they said no.

4:46And I was told if I wanted them, I could file a Freedom of Information Act request for them, which I did. And I was recently informed by the National Archives that they will process my request in 20 years. I all of a sudden realized, light bulb went off. Huh, I see why someone might have just taken these in a plastic grocery bag and handed them off to the next administration. Ian's story of binders in the night is shocking. We don't expect decades of rules and guidance for government ethics to be passed down in such an ad hoc way. It shows how heavily our system rests on seasoned professionals having a respect for democratic norms.

5:24But his story of the binders is also reassuring. It shows how so many people across political eras and divides have worked so hard to uphold the standards that our lawmakers need to follow. And it's that preservation and passing on of standards that Ian Bassin went on to make his life's work. He left the White House and drew on his experience as an administration lawyer to found an organization called Protect Democracy, where, full disclosure, I'm a founding board member. The mission, you guessed it, to protect American democracy. Ian's not-for-profit has had a huge impact. And unlike most policy and litigation-focused not-for-profits, they're also a tech organization, having built and launched software called VoteShield, which helps secretaries of state ensure they're running free and fair elections.

6:11I want to emphasize here that Masters of Scale is not a political show. We explore how to scale businesses, and that is the focus of this episode, massively scaling an organization with a specific, important mission. We invited Ian on to learn how he's built strong partnerships across opposite ends of the political spectrum and how he's done it with a 100 % distributed workforce long before the pandemic work-from-home era began. I'm Jeff Berman, your host, and this is Masters of Scale. You've got to have incredible talent at every position. It's like this huge push. There are fires burning when you're going home.

6:51Can you believe it? Such an idiot. And then you go back to, this is totally going to be amazing. There are so many easy ways. I have no idea what to do. Sorry, we made a mistake. But you have to time it right. Oops. Working out of a three-bedroom apartment. Stuff that just seems absolutely nut balls. Ten years later, we're like, well, that's just how you do it. We haven't made it just how you do it.

7:15This is Masters of Scale.

7:25Today I'm in conversation with my good friend Ian Bassin. Ian is a co-founder and executive director at Protect Democracy. It is a not-for-profit dedicated to preventing America from sliding into authoritarianism. He has over 100 staff members with a wide range of political views. They do things like safeguard free and fair elections by tracking voter registration data and ensuring there's nothing nefarious at play. They provide legal counsel for election workers and others being threatened and defamed for their nonpartisan patriotic work. Ian and I explore how to work together to address massive challenges with no obvious solutions and how to share best practices with your predecessors, your successors, and occasionally even your competitors.

8:12First, let's hear a little more from Ian about his three-year stint in the White House.

8:21The thing that was so striking was that everyone understands from the president on down that we are temporary occupants of an office. We hold an incredibly precious and valuable public trust that we the people, the citizens, give to us temporarily only on the condition that we will exercise it in their best interest, on their behalf. And it was part of my job to drill that into, you know, the minds and the hearts, every way that everyone operated in the building and in the executive branch. And that really did, you know, for the most part, transcend parties and administrations. There's one part of this that I'm really struck by, which is it doesn't matter what party you all were working together to preserve the rule of law and ensure that the White House was operating in an ethical manner.

9:07Is there any prep for this job? Do they give you any context for what you're doing? Or do you just walk in on day one and say, I guess I'm working for the president? So a little bit of both. So one thing that's kind of staggering, and I remember this feeling vividly when we walk into the building, noon on January 20th is the West Wing, the executive office building. The rooms are empty. The desks are clean. There are no papers. There's a computer there for us and nothing else. And this is the seat of the most powerful government in human history. And you walk in, and it's just empty for the new group of people.

9:41And it was just a wild experience to realize that every four years, there's the opportunity to just swap out the old people and bring in the new and start afresh. And a new group of people come in, and they take the keys, and they take over running the federal government. It's a remarkable thing that we've been able to do in this country for 247 years. We've covered the concept of refounding plenty of times on Masters of Scale, most recently in my talk with Reid Hoffman, which you can find in our episode feed. It's something I'm focused on as the relatively new CEO and refounder of Wait What, the company behind this podcast.

10:17It is not easy. So the idea that the federal government goes through a complete refounding every four to eight years is mind-blowing. And the reason it works, at least most of the time, is the deep respect for not just the office, but the rules and conventions that came before. The goal of a peaceful transition of power speaks to the dance every refounder must perform to make their own indelible mark on an organization while keeping its mission intact. After almost three years working in the Obama administration, Ian took on a different challenge in 2011. He went to the not-for-profit Avaz, which is focused on global organizing to protect the environment, human rights, and freedom of speech.

10:58It was here that Ian learned a foundational lesson about building a scaled organization that can sustain a succession of leaders. The thing that was, for me, the most eye-opening was not the subject of the work, which was fascinating and meaningful and important. It was how it was done. It was led by a management savant in how to think about intentional culture in a workplace that built the culture from the ground up from the beginning as the DNA of the organization and wove it into everything the organization did, how it tested in hiring, how it onboarded and trained people to operate within the organization, how it injected that culture into every team meeting, into every interaction, so that ultimately, as the organization scaled, that DNA replicated.

11:39And even if the organization grew to be 1 ,000, 10 ,000, however big you wanted to be in every meeting, even if the original team was not present, you could sort of assume that the way the people in that meeting would approach the problem would carry with it these sort of core principles. In 2015, Ian left of Oz and joined another not-for-profit where the approach to culture was, let's say, less rigorous. Culture became kind of those principles on the wall or like on the website. But if you tapped anyone on the shoulder in the middle of a workday and said, name the values of the organization, they couldn't recite them.

12:16And certainly if you said, when was the last time that you invoked them with a colleague in the course of your work? Never, right? And so it was like a human A-B test for me. I was in two different organizations, seeing what it was like to do intentional culture and seeing what it was like to put cultural principles on a wall. And nothing could have been more powerful at proving the importance of doing that. The opportunity to closely compare two vastly different approaches to culture is a gift to any leader. It hammers home what's needed. You can't just speak an effective company culture into existence.

12:47You need to set the example of living the culture. That is how you truly empower your team to embody the culture themselves. Fostering a culture of empowerment, communication, and similar values is crucially important. It cultivates a sense of leadership within every team member. It establishes a common language and mindset that facilitate effective execution of tasks. And it shapes the way work is accomplished. It's a lesson Ian would draw upon when he founded Protect Democracy in 2017. But I'm jumping ahead. For now, let's stay in 2015. Ian had taken a role at a second not-for-profit, coming in as chief operating officer.

13:27However, his role was soon thrown into turmoil, along with his self-confidence. I came into that organization as the COO. And within three months, I was at dinner with the founders. They said, this isn't working. You've lost the trust of the organization. We're going to have to demote you. and I had to appear in front of the entire organization to announce my demotion. I asked if I could announce it, and they said, no, we're going to do it. So you can imagine how humbling an experience that was. Okay, let's just pause here to appreciate how this must have felt for Ian. He'd been successful in the White House as one of the president's most trusted advisors, and now he was being very publicly demoted.

14:04It is hard to stumble professionally, but it is brutal to have your failures publicly paraded. It's also not the end of the world. You can springboard from experiences like this to build your tolerance for failure and your comfort with risk. And that's one heck of a perspective to have when you're leading through uncharted terrain. Let's jump to November 9th, 2016, when the seed of what would become Protect Democracy was planted. I was in voter protection headquarters in Philadelphia in this law office. I was one of the earliest to see what was happening. There was an empty box on the floor, and out of frustration, I wound up to kick the empty cardboard box into the wall, and it wasn't empty.

14:46And so the box didn't budge, and I broke my foot. So I wake up the next morning with my broken foot, and there's an email from a friend and former partner in other projects who had also been in the White House Counsel's office all after me by the name of Justin Florence. and the email said, should we get the White House Council alumni together and talk about what's coming and whether there's something we can do about it? Justin's email brought to Ian's mind that bag full of binders he'd been tasked to collect on that Washington, D.C. evening back in 2009. The insight was that all those binders that I talked about, all those unwritten laws, all the ways in which presidents of both parties had understood that there were restraints on their office and on themselves and that they held a public trust, that we recognize that with the election in 2016, something fundamentally different was about to happen.

15:39And so the question was, what would happen if someone threw out those binders and said, these rules are for suckers? Ian and Justin immediately began brainstorming ways they could deploy their expertise to counter this imminent threat. We had a very clear mission statement from the get-go, which was prevent American democracy from declining into a more authoritarian form of government. As an entrepreneur, that mission resonates because it identifies an urgent need in the market, specifically the need to protect American democracy. The next thing the founders had to do was make the case for why they were the ones best placed to help in this monumental task.

16:17We felt like we had some comparative advantages because having been the lawyers inside the White House, one thing we really understood was how actors outside of government could influence and impact actors inside of government, because we'd been on the receiving end of that. This was their unique selling point. Ian and Justin had seen firsthand the potential for democracy to be undermined by bad actors. Just as white hat hackers used their understanding of a computer network's vulnerabilities to shored up against malicious attacks, Ian and Justin would use their inside knowledge to protect the nation's democratic processes and institutions.

16:55The precise tools they would use to do this, however, remained unclear. We knew the Achilles heels in government, but the actual products we were going to need to create was a little bit TBD. And so we had to build a pretty nimble company from the beginning. This is such a smart way to approach launching an organization. You see an urgent need and you know you have the expertise and drive to address it, but you lack a specific product. If Ian and Justin had waited around until they had concrete approaches, it might have been too late for American democracy. So Ian's insight to focus on how to be nimble and how to pivot was an inspired approach, especially when you consider the breakneck speed of politics and the news cycles at the time right after that election.

17:40Time was of the essence. Ian and Justin had their mission. They had their theory of action. They had their nimble approach. So what did they do next? Nothing. About two or three weeks go by after the election, and are we really going to start a new organization? We just didn't have quite the confidence we needed to do that because it takes a lot of hutzpah to start a new organization. Hey, look, we've all been there. These feelings are usually in direct proportion to the size of the task. and what could be bigger than saving American democracy. As is so often the case in these crisis of confidence moments, the reasons not to act started piling up.

18:22You know, at the time, not only did I have a broken foot, but I had my first child due in two months. I had a good job at another really wonderful nonprofit at the time called Give Directly. So this notion of like, are you going to start something new? We just didn't have that oomph to get over that hump that I'm sure a lot of founders know that moment. We've heard it so many times on this show before, but it's still hard to imagine for leaders as capable as Ian. Fortunately, he soon received a call that helped him rebuild his confidence. It was from two of his former colleagues in the White House Counsel's Office, Karen Dunn and Blake Roberts.

18:55They said that there had been a meeting in Washington, D.C. that day of a lot of meeting lawyers in the district, people who had led the Department of Justice, also had been in the White House Counsel's Office, and that there was a discussion that there was a need for a new organization, given the moment we were in. And my name was floated as someone who should lead it. And everybody agreed. That's quite a moment. Yeah, it was a moment I'll never forget, both for it's what people really think I can do this, right? That sense of it was humbling. It was flattering. But most importantly to the story, it was confidence building.

19:30And maybe not just confidence building, but there was also a little bit of, Uh-oh, people expect me to do something. Right? Well, and also, you just recently suffered this gut punch of being demoted publicly in the company, in the not-for-profit you were working at. So, I hear you on the, it takes chutzpah to write out these culture principles and this mission, and then to get this phone call. Where did you summon the confidence, having just recently been knocked down a peg? How did you manage through that? I remember vividly getting the call from them and flashing back to when I started in the White House Counsel's Office as a baby lawyer in 2009.

20:05And I went into the White House Counsel's Office and I thought, I don't know a lot about how this place works. I should really sit back and listen. And so I would go into every meeting in the West Wing or the Executive Office building. And the first thing I would do is I would take the seat furthest from the center of the room. I would go sit against the wall as a wallflower. and two of my colleagues, who were pretty much the same vintage attorneys that I were, they'd go sit at the head of the table. And you know what? People treated them like they ran the meeting. And it was a real lesson in people will treat you the way you act.

20:37And that doesn't mean that you have to be overconfident. It doesn't mean that there isn't an important place for humility and curiosity and listening and asking questions. But if you treat yourself as on the outskirts, then you'll be treated as on the outskirts. With this lesson in mind, Ian seized the moment. And I remember saying to myself, 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. You listen, but you definitely lead. I love this phrase. It's a concise and strong summation of the constant balance all leaders need to maintain.

21:11And it's applicable far wider than the C-suite. It's something that every team member should adhere to. If everyone acts like they're invested in the mission and listens like a learner, you'll build resilience, belonging, and a propulsive sense of mission throughout your organization. With this vote of confidence, Ian was reinvigorated to launch this new organization, which they named Protect Democracy.

21:47Real leaders don't back down when the stakes are high. They innovate, they push forward, and then they take the stage at the Masters of Scale Summit. Join us in San Francisco, October 7th to 9th, to hear from the CEO of the New York Times, scientists using cutting-edge technology to find cures, the leader of crypto powerhouse Coinbase, a retired four-star general, and many, many more. apply now at mastersofscale.com slash apply25. That's mastersofscale.com slash apply25. If you're ready to take your startup from idea to impact, then AWS is your launchpad. From data storage to machine learning to secure app hosting, AWS gives you the tech trusted by the world's fastest scaling startups.

22:37And here's the best part. Join AWS Activate today and you could score up to$100 ,000 in AWS credits tailored to your stage and network. Go to aws.amazon.com slash activate and start building. Expanding your business in the U.S. can feel like a maze. Every state has its own payroll, benefits, and compliance rules, which can pull your focus away from growth. That's why founders use Deal. Deal is the professional employer organization, or PEO, that gives you a dedicated HR expert plus Fortune 500-level benefits for your team. The National Association of PEOs says businesses can grow twice as fast if they use one.

23:21So if you're scaling, make it simple with Deal. Go to deel.com slash mos and get up to three months free. Welcome back to Masters of Scale. I'm Jeff Berman with our guest, Protect Democracy founder Ian Bassin. If you want to hear our entire conversation, you can find that on our Masters of Scale YouTube channel. Before the break, we heard about Ian's rocky journey in the run-up to founding Protect Democracy. I asked him about those early days, taking the idea from concept to actual scalable organization. You have this concept that you build out. You get this call from Karen Dunn. You identify the problem, but now you actually have to do the thing, right?