Introduction: Your Face Here

“I don’t care about being in the press. That’s not important. It’s the 14th District and changing the narrative that communities like mine aren’t flippable. Because if people around the country believe in the suburban swing districts, then we will win.”

Congresswoman Lauren Underwood, Illinois 14th, March 9, 2018

Imagine this: You’re a newly elected member of Congress, sitting in your office on Capitol Hill, representing thousands of people back home in your Midwest district. Just 18 months ago, you’d never run for office, never launched a campaign, never led campaign rallies, or talked on live national TV — much less flipped your longtime Republican district from red to blue.

And yet here you are. You did it.

You pulled it off because, at some point, you had a feeling that you could. And then something — a desire for change; a dawning awareness that, when it came to the problems in your community, the cavalry wasn’t coming — tipped that feeling of could into should.

We’ve seen it happen over and over again. In fact, the dream vision above is the story of one of our candidates, Congresswoman Lauren Underwood, a nurse with a pre-existing condition who in 2017 was so alarmed by the Trump Administration’s promise to take away affordable health care that she jumped into the ring. A Black woman who had served in the Obama Administration, she ran in Illinois’ 86% white, part-rural, part-suburban 14th District, and — with no prior experience and no meaningful party support when she began — defeated six white male primary opponents and then a four-term Tea Party Republican incumbent. In 2019, at age 32, she became the youngest black woman ever sworn in to the United States House of Representatives, occupying a seat formerly held by Dennis Hastert, the longest-serving Republican House speaker. 

Lauren Underwood’s journey from everyday citizen to Congresswoman may seem daunting, even impossible for you to imagine.  And yet, if you’re reading this, it’s probably because you’ve been bitten by the bug of what-if and why-not-me political daydreaming, too.  You may be someone who’s considering a first run for office or is at the very beginning of their first campaign. Or someone with no experience in the campaign world who’s about to start helping a first-time candidate prepare a run for office and is wondering where to begin.

We hear you. For the past three years, we’ve been working with people like you,   accompanying them on every step of the journey from thinking about entering politics to running to winning to transitioning to office and governing. Or sometimes, to not-winning, and to going on to do other equally valuable things.

“We” are Will Levitt and Miti Sathe, co-founders of Square One, a non-profit PAC we started in the early months of 2017 when, like many Democrats around the country, our shock and grief about Donald Trump’s election turned into a resolve to do something to create change. It was clear to us that the old political playbook wasn’t working for Democrats, who were out of power not just in the White House, but in the House and Senate and, around the country, in 34 state legislatures — the governing bodies that make the all-important decisions about how Congressional boundary lines are drawn. The problem wasn’t just that Democratic candidates weren’t winning; Democratic voters weren’t even turning out to the polls, because such a large portion of the electorate — Democratic-leaning young people and people of color above all — had come to feel that there was no point. Politicians didn’t seem to really understand or care about the challenges that most people were facing — and if they did care, they weren’t acting on the feeling. It was all the same old, same old.

We knew we needed a new cohort of idealistic and deeply committed Democrats — people who weren’t part of the long-entrenched party machine — to take their seats in the rooms where big decisions are made in Washington. We were part of the huge, emerging, and unprecedentedly diverse generation that was starting to make its mark on American politics. And we suspected that we had a collective skill set that we could put to very good use in helping the sorts of insurgent candidates we wanted to see in elected office: a flexible, creative, and go-for-it startup mentality based on decades of combined experience in small business entrepreneurship, creative marketing, and working on political campaigns, with particular expertise in the rapidly-evolving world of digital communications and media. Above all, we shared a mission: To find and help elect new, bold, and highly effective Democratic leaders who look, think, and have experienced life like the full range of the people they represent. If we could find and support candidates who would really excite and mobilize voters and inspire them to turn out at the polls — diverse candidates who know all too well what it is to have to hustle for work, worry about health care, and bear the burden of crushing student loan debt — we believed we could permanently change the face of our country’s political leadership. 

From our previous professional lives in and out of politics, we knew that the structural barriers blocking opportunities for people of color were alive and well and powerful – even in the purportedly “post-racial” Obama era. And from early conversations we had with promising potential leaders who told us they couldn’t run for office because they didn’t have the time, the resources, the connections, or even the slightest clue of where to start, we saw that there were a set of very specific structural impediments that were keeping young people, non-wealthy people, women, people of color, and members of the LGBTQ community from running for office.

We decided to work exclusively, hands-on and intensively, with those kinds of candidates, and to focus on getting them into Congress. We went right into their districts, helping them take down the barriers to entry that have consistently kept people like them out of office. We helped them understand how to find out which paperwork to file and how to fundraise, how to find office space and hire staff, how to conceive and carry out campaign strategy, deal with media, and navigate the inside-baseball world of Washington politics.

We concentrated our efforts on flipping red districts blue — particularly those that were previously overlooked by the Democratic Party — and on making a long-term commitment to those districts so that we could help make sure that talented Democrats would be present on the ground in every single district in the United States. And we made it our mission to support people from underrepresented and underserved communities who lack personal or family wealth, powerful and wealthy connections, institutional backing and the sense of entitlement that helps launch so many political careers in the first place. In fact, our goal has been to make voters, donors and the candidates themselves see that those seeming disadvantages are actually great sources of strength.

We’re proud of the work that we’ve done.  We’ve learned a lot along the way. And we’ve written this guide so that we can share our accumulated knowledge with you. 

 It is not (just) a tool kit. We won’t simply give you a list of bullet points to navigate at your own risk. We’ll show you what it feels like to run. What it costs – emotionally, financially, and in time away from work and family. We’ll demystify the world of paperwork, fundraising, communicating with voters, turning out voters, and navigating the dizzying world of paid campaign consultants who will offer to help you with all the above. We’ll show you how to run a campaign and we’ll tell you the stories of people like you who have done so successfully. We hope we’ll be able to help you see that it’s not only possible for someone like you to run for Congress (or for any office); it’s totally doable.

Our candidates have accomplished great things: they’ve energized thousands of people to become politically active for the first time, flipped districts thought to be unflippable, successfully changed campaign finance law to help working parents run for office, and proven that diverse candidates can win in districts in every corner of America. When we first started in 2017, we picked eight candidates to back and we thought, if we can get one of our candidates past their primary, we’ll consider it a big success. All our candidates won their primaries in 2018. Three of them went on to win their general elections, flipping their seats from red to blue in the U.S. House of Representatives. All of our candidates, whether they won or lost, shifted their districts to the left by an average of 16 points. And in the extraordinarily difficult congressional elections of 2020, all of our incumbent candidates held their seats.

Collectively, our candidates have created a blueprint for leading our country bravely into the future — whether or not they won their individual races. We’re going to show you how they did it. It wasn’t easy, for sure. (But then, as the saying goes, nothing worth having comes easy.) Great candidates do tend to have a kind of magic about them — a special something that makes people’s hearts sing when they speak — but there’s nothing magical about winning. All the things about politics that from the outside look glamorous — the parades, the public adoration, the glory, and the general fandom — actually take months and months of planning and hard, grueling work.

But that’s okay. After all, hard work and careful planning have a big silver lining: unlike magic, they’re real. Anyone can successfully do them. Including someone like you.

So let’s get started, so you can get started on running, (hopefully) winning, and transforming America.