When I sit down with Diane Hessan for a recent conversation, the entrepreneur, startup investor, and budding political researcher is nothing but hearty laughs, cool optimism, and earnest passion about her work.
That’s despite having spent the past year and a half corresponding with hundreds of American voters on a weekly basis, during one of the more polarizing periods in U.S. history. Lately, the voters are feeling burned out from the constant political bickering on Capitol Hill and the divisive nature of much of our discourse in the online corridors of Facebook and Twitter, on TV, at the dinner table, and elsewhere. But it seems Hessan’s conversations with voters have energized her and infused her with more hope about America and its people.
“We are so much less divided than people think we are,” she says, as we chat in a conference room in the Boston offices of C Space, the market research and consulting firm she co-founded in 1999 and now chairs.
In the summer of 2016, Hessan (pictured above) left her job as CEO of Startup Institute to consult for Hillary Clinton’s presidential campaign. She was tasked with finding undecided voters in swing states and gathering insights that might help Clinton’s team better understand them. Hessan drew from skills and experience gained through running C Space (formerly called Communispace) for about 14 years, and she found that she enjoyed and was fascinated by talking with voters. After Donald Trump won the election, Hessan decided to continue having regular conversations with voters and self-fund the project.
She says she recruited a new group of about 450 voters—45 percent Republicans, 45 percent Democrats, and 10 percent independents. They correspond weekly, mostly through e-mail, Hessan says. She usually poses a question for them to answer, like how they’re doing lately, or perhaps she’ll ask them to do something creative, like fill out a “Mad Libs” word game, she says. She will have occasional phone calls for “really meaty issues,” she says. (She pens columns for the Boston Globe about what she learns.)
“My agenda is I’m trying to understand, I’m trying to find common ground, I’m trying to see if there’s any way that we can move forward together,” Hessan says. “And I’m also trying to just educate everybody about what’s going on on the other side.”
I wanted to speak with Hessan to hear more about her foray into politics and to find out whether her conversations with voters hold any lessons for the tech industry. After all, politics and technology are frequently colliding these days, from fake news spreading through social media to rising concerns about online privacy and cybersecurity. In a wide-ranging discussion, we explored some of these topics, as well as Hessan’s thoughts on improving diversity in tech and the venture capital industry, the challenges around retraining workers for an evolving economy, her prescription for fighting fake news and social media’s ills (it’s not all Mark Zuckerberg’s fault), and one of her (many) new startup ideas.
Here are the highlights of our conversation:
Xconomy: Your most recent column talked about burnout among American voters. Do you feel like people have reached their breaking point? And if they have, what follows?
Diane Hessan: Well, look, what follows burnout? It either gets worse and people totally freak out, or somebody makes change, or there are enough people who are fed up that something productive comes out of it.
I see one outcome of people being so exhausted is that they are more open to compromise in the name of progress. If they understand other people, they’re a little more open to shifting their views—not necessarily radically, but enough to be able to say, “OK, so now that I understand what’s going on for you, I think I see a way through the madness.”
X: How will that sentiment that you’re seeing among the voters manifest in Washington? Do you think it will lead to more moderates in Congress?
DH: I don’t know. … I’d bet that we’d have more moderates. But it’s hard for moderates to win in primaries because the extremes all come out passionately and vote for what they care about. But yeah, I think this is the time for moderates. I think Mitt Romney is going to win in a landslide, whether he’s in Utah or elsewhere.
There are Democratic voters that admire Susan Collins more than they admire Elizabeth Warren. There are Republican voters that admire Lindsey Graham more than they admire Ted Cruz or the like. I think it’ll be a really interesting time.
X: What are some of your takeaways from talking to voters every week?
DH: If I get out of Massachusetts and I talk to my voters, I think people know that I’m not a Trump supporter, and yet I’ve got a lot of voters that I talk to on a weekly basis who love Trump. After talking to those people every week for 18 months, I’ve come to have huge respect for and admiration for many of those people, independent of who they voted for. So, I’ve been able to kind of separate how I feel about the president from how I feel about the people who support him.
I’ve really gotten to understand their lives. I will tell you, a 55-year-old, unemployed coal miner is not going to learn to code. And what happens is you get all these politicians up there screaming, “Retraining the workforce, retraining the workforce, retraining the workforce.” We need to really get very, very concrete about what the opportunities are going to be for people who are further along in their careers.
Go to Milwaukee. Look at people who are unemployed there.
Look at people who have lost their jobs in the automobile industry. Will some of them learn to code? Sure. But it’s going to be a small fraction. And so, what I’m really interested in is who’s putting together a jobs policy for the future that really makes sense. Where’s the plan for our workforce when the economy changes all over the place? I think that’s a really interesting area. I’ve got a lot of energy for that.
X: Something Xconomy focused on in interviews at the end of 2017 was what we and others have called a tech backlash because of a confluence of issues: fake news, Russian interference in the presidential election, social media companies not having the best response to those issues, sexual harassment allegations at tech companies, and the growing concentration of power in just a few companies. Does any of that come up in your conversations with voters?
DH: It comes up a little, although I must say I think that’s a really interesting issue, and I could [discuss it] a little bit more with my voters. I think it’d be interesting to see what they’d say about that.
They’re all upset about the media. They’re all upset about fake news, across the spectrum. I think Facebook and Twitter have done an absolutely horrific job of handling the problem.
Where they have missed is they haven’t
