George was one of the many “friends” I made over the last four months, while working on special assignment for the Clinton campaign. My task was to help her campaign understand undecided voters in swing states. Finding them and getting insights from them was right up my alley — a skill I honed over my 14 years as CEO of C Space — and when I got a call to help, I couldn’t resist. I left my job as CEO of Startup Institute, and was off and running.

WHEN I WAS growing up outside of Philadelphia in the ’60s, a friend lived in Wilkes Barre, Pa., and so I was excited this past July to be on the phone with George, a 58-year-old Democrat from the same town, who was undecided about which presidential candidate would get his vote on Nov. 8.


At first, I couldn’t understand how anyone could be undecided. The distinction between Donald Trump and Hillary Clinton was so clear to me, the gap so wide. Much to my surprise, it was easy to find the Undecideds: people who had significant enough reservations about both candidates that they were searching for a sign, looking for more information, or just waiting it out until November.

Over the summer, I found and interviewed over 300 undecided voters, and 250 of them agreed to stay in touch, to send me weekly diary entries about their emotions, what they were thinking about both Clinton and Trump, and how they were leaning when it came to their vote. I had no responsibility to change their views; instead, I synthesized the data that I was collecting, and reported in to the campaign. I also added the insights that I had and made regular suggestions about how the campaign might better articulate its positions and modify its strategies.


When George and I spoke, I told him I had been in his town several times, and he told me how the Miners Bank building had been turned into luxury condos. “Nice, but not for me and my neighbors,” he added.

George’s story was one I ultimately heard over and over: He had lived in that part of Pennsylvania his entire life, had worked hard, raised a family, paid his debts, sacrificed to get his kids through Wilkes University, and tried to do the right thing for others. “The government never helped me, but I was OK with that,” he said. “I made mistakes, had some scary moments, and my wife worked also at the local library to help out. I paid my bills, including my doctor bills.

“Now I see my tax dollars going to handouts for others who don’t want to work as hard as I did, and I can’t afford my health care. Everyone is being taken care of but me. I feel left out, and it makes me feel that I want my country back.”

All through the summer and into the fall, George was undecided. Clinton was a Democrat, and Democrats historically helped the working class — but Trump painted a new picture.

As time went on, George was more and more disgusted. “All I know is that I am going to hold my nose when I walk into that voting booth,” he said. “Trump is a loose cannon who arrived on third base at birth — and I have never trusted the Clintons, from Whitewater to the Foundation.”


Listening to all of the Undecideds, I thought that there was still hope for the Clinton team.

In July and August, many interesting themes popped up. For instance, early on, I learned that the attraction of Trump was that he was a successful businessman. People did wonder about how successful he really was, and I wrote a piece to the campaign about Trump and his tax returns. Voters didn’t care whether he paid taxes or not — and thought he was smart to pay none. But they thought Trump’s returns could show whether he was charitable (important) and whether he was as rich as he claimed he was (more important).

In September, more themes arose. The undecided voters didn’t really believe Clinton had health problems, and most didn’t believe that Trump was a racist. They were sure that Clinton cared more about climate change (which they mostly also cared about), and that Trump would never get Mexico to pay for the wall. And they weren’t worried that Trump didn’t know what was going on in Crimea, because they didn’t either.

During the debates, I tracked what was compelling and reported in. They liked it when Clinton was calm and not shouting. They were bombarded by NRA ads that claimed Clinton would take away their guns. It bothered them that Trump was a bully and was outrageous in his insensitivity to people with disabilities. It bothered them that someone on Clinton’s staff literally took a hammer and smashed her Blackberries. On the other hand, Bernie Sanders was right: My voters were sick of hearing about e-mails.


Last week, I reread all of my notes. There was one moment when I saw more undecided voters shift to Trump than any other, when it all changed, when voters began to speak differently about their choice. It wasn’t FBI Director James Comey, Part One or Part Two; it wasn’t Benghazi or the e-mails or Bill Clinton’s visit with Attorney General Loretta Lynch on the tarmac. No, the conversation shifted the most during the weekend of Sept. 9, after Clinton said, “You can put half of Trump supporters into what I call the basket of deplorables.”

All hell broke loose.

George told me that his neighborhood was outraged, that many of his hard-working, church-going, family-loving friends resented being called that name. He told me that he looked up the word in the dictionary, and that it meant something so bad that there is no hope, like the aftermath of a tsunami. You know, he said, Clinton ended up being the biggest bully of them all. Whereas Trump bullied her, she bullied Wilkes Barre.

Things were not the same after that, at least with my voters. I remember wondering whether that moment was like Romney’s 47 percent: a comment during a fund-raiser from which the candidate would never recover, proof that, like Romney, Clinton was an out-of-touch rich person who didn’t really get it. It struck me that many of the people who were considering Trump were just hard-working Americans who wanted better odds for a good life.


George stuck with his weekly diaries until the very end. He went to two rallies: a passionate event with 500 attendees honoring Joe Biden — “I like him, but he is not running” — and a rally on Oct. 15 for Trump, along with 10,000 other neighbors. He told me that the Trump rally was “the most fun I have had in years. Trump would say, ‘What am I going to build?’ And we would scream, ‘A wall!’ He would say, ‘And who is going to pay for it?’ We yelled back, ‘Mexico!’ He thought we were smart and he didn’t talk above us. We know that he’s not actually going to get Mexico to pay for it, but it was fun to lighten up, to cheer along with everyone else, just like back in high school, when we would cheer that our teams were definitely going to win, even when they were bad.”

I heard this from scores of undecided voters in swing states. They didn’t like either candidate. They just wanted to be understood. At the end of the day, they cared less about Trump’s temperament and more about whether he “got” them. They were smart, they knew the cheers, Trump gave them a voice, and he certainly didn’t think they were deplorable. I didn’t hear this from everyone, but it was striking to read the comments of voters who were struggling to make a decision, and who went with the candidate who made them feel important. It might have been enough to make 70 electoral votes’ worth of difference.

It is crushing to me that Clinton lost. When my mother was dying, in 2014, she told me that her only regret was that she never saw a woman president. I wanted to see one, and Clinton was my big chance: a smart, committed, experienced woman who would be trusted to deal with the most serious of crises. I could taste her victory: Even with her flaws, she was running against a misogynistic, racist, inexperienced birther.

George voted for Trump. He told me it was a difficult decision, but that he is optimistic that it will be fine. He told me he hopes that I go to Washington on Jan. 21 to send Trump a message that women and minorities still count. I will be there with my daughters, hoping that my new president will try hard to understand me.

So, where do we go from here? I don’t know the full answer, but my recent experience does help me know where to start. Whether you liked Clinton or not, we can probably all agree that we are Stronger Together — and I have learned that instead of speaking about each other, we need to speak with each other. If you had asked me to describe a Trump voter last spring, I would have been largely wrong about their motivations, dreams, and even their values. Sure, there are extremists among them, but it was eye-opening to realize how legitimate the concerns of many are, and to realize that, if I just listened hard, I would find that I have more in common with the Georges of the world that I could ever have imagined. Empathy — trying to understand others as deeply as possible — is an important first step, whether around the Thanksgiving table or in social media. President Obama said it eloquently last week, noting that our election is ultimately an intramural scrimmage because we are all on one team. If we believe in liberty and justice for all, we have to acknowledge how terrible it is to feel left out — and then to ask questions, learn, and walk in each other’s shoes.

Diane Hessan is an entrepreneur, investor, and chairman of C Space.