In recent years, more and more technology experts have been developing new tools for boosting civic engagement. Sara Gifford embodies the trend. At the end of 2018 she set aside her budding tech career — after a decade at supply-chain software firm Quintiq she'd become chief operating officer for Dispatch, which makes software connecting home-service brands with contractors and clients — and co-founded ActiVote Inc. Its free app aims to increase political participation by giving voters access to information about candidates and elections, as well as encouraging their civic engagement. Her answers have been edited for clarity and length.
What's the tweet-length description of your organization?
We are a safe, nonpartisan space for voters to learn about their elections, the races, how to vote and which candidates believe what they believe. An informed voter feels empowered. And an empowered voter shows up to vote.
Describe your very first civic engagement.
My parents voted at our elementary school in rural Connecticut and would take my sisters and me to the polls with them. I remember not being allowed into my classroom until my parents voted. When I whined and complained, they would tell me there is nothing more important than voting and not to take school — or democracy — for granted.
What was your biggest professional triumph?
When you build something the question is always: But does it work? Well, last month we finished a study showing that downloading our app increases your chance of voting 33 percent. This was very encouraging for us. More importantly it should be encouraging to everyone else in this space. It means there are new and innovative ways to get people to the polls.
And your most disappointing setback?
There is an old saying, "It can take years and years of hard work to become an overnight success." We are working hard for our overnight success to come! But, no worries: See the answer to the question below about advice.
How does your identity influence the way you go about your work?
I have heart. I am relentless. I am dedicated. I take all of those values and apply them to life and to our work increasing voter participation, because it takes all of those things to maintain our democracy.
What's the best advice you've ever been given?
Vince Lombardi said, "Winning isn't everything, but wanting to win is." We may not always be as successful or as fast as we would like, but the one thing we can control is our endless drive to want to do good and to work hard to get there.
Create a new flavor for Ben & Jerry's.
Vote Ready: Strawberry and vanilla ice cream with blue sprinkles built on top of chocolate brownies.
What's your favorite political movie or TV show?
"The West Wing," which ran from 1999 to 2006 on NBC and is now available on Netflix.
What's the last thing you do on your phone at night?
Set up my white noise app so that I sleep like a baby.
What is your deepest, darkest secret?
As a kid I once hid the last piece to a puzzle my little sister and I were doing, knowing it would drive her crazy. But when it came down to finishing the puzzle I couldn't remember where I hid it. Still have never told her!
image of U.S. President Donald Trump is displayed on a digital billboard in Times Square in New York on April 8, 2026.
Trump is stuck between two realities. Neither serves the American people
Normally, I worry that events may overtake a column. But not so with the Iran war.
I don’t worry about running afoul of a headline or Truth Social post from the president because what is said about the situation is no longer very relevant to the reality.
On April 8, Nick Catoggio, my Dispatch colleague, dubbed an earlier stoppage with Iran “Schrödinger’s ceasefire.” This was a reference to the famous thought experiment by the physicist Erwin Schrödinger, who was trying to explain the weirdness of “superpositionality” in quantum physics. A cat in a box is both dead and alive at the same time until you open the box. Schrödinger meant to illustrate the absurdity of the idea that particles aren’t any one thing, but a “cloud of probabilities.”
The Trump administration is stuck in a word cloud of probabilities of his own making. The war is over. The war is on. The war isn’t a war. We have a deal, but we don’t have a deal, but we’re about to have a deal. We destroyed Iran’s military. No, we left it intact. We want regime change. No we don’t. We already accomplished it. We “obliterated” Iran’s nuclear program a year ago. We had to go to war in February to prevent nuclear war. The Strait of Hormuz is open, closed, or something in-between. No deal without “unconditional surrender.” Let’s make a deal!
This everything-all-at-once vibe can be disorienting, particularly since most Americans didn’t have a war with Iran on their bingo cards until the shooting had already started. President Trump didn’t prepare the country or consult with Congress beforehand because he thought it would all be a smashing success in a matter of weeks.
The miscalculation that started it all: killing Iran’s Supreme Leader, Ayatollah Ali Khamenei, and much of Iran’s senior leadership, on the first day of the war. To “the great proud people of Iran, I say tonight that the hour of your freedom is at hand,” Trump announced on Feb. 28. “When we are finished, take over your government. It will be yours to take. This will be probably your only chance for generations.”
I support regime change in Iran and shed no tears for Khamenei or his goons. But when you start a war by killing the regime’s top leaders, it’s not unreasonable for the remaining ones to conclude that you really intend regime change.
Khamenei was a murderous fanatic, but he was a fairly cautious one. He liked to threaten closing the Strait of Hormuz or attacking our regional allies, but he was reluctant to actually do it, fearing it would invite a regime change war. The mullahs and IRGC goons believed, not unreasonably, that if they lost their grip on power, they’d be lynched by the Iranian people they’ve brutalized for decades.
By starting with a regime change war, Trump removed any reason for the regime not to go for broke. When you have nothing to lose — particularly when you are a millenarian religious fanatic — a Persian Alamo strategy makes a lot of sense.
So Iran closed the Strait of Hormuz and attacked its neighbors.
But it turns out this wasn’t the Alamo. In the contest of wills, Trump blinked. The Iranian regime’s tolerance for punishment proved — so far — to be greater than Trump’s and that of our gulf allies. Militarily we could finish the job, but that would require ground troops and much greater economic turmoil. In a conflict Trump launched unilaterally without the prior support of Congress, NATO or the American people, Trump doesn’t have the political capital for that.
But that’s only half the problem. Trump wants the war over, but he doesn’t want to pay — militarily, economically, politically — what that would cost. So he wants to make a deal that ends it. But there is no deal available that wouldn’t come at an equally undesirable cost. Any deal that looks like what President Obama struck with the Iranians would be too embarrassing to bear. But the Iranians are convinced that they can get just such a deal, and they’re willing to drag things out as long as it takes.
The result: Trump’s in a box of his own making. He thinks he can talk his way out by simply asserting a reality that doesn’t exist. When the financial markets get nervous, he announces a breakthrough that is, at best, a possibility. When the Iranians agree to a deal that looks similar to one Obama might negotiate, Trump goes back to his threats.
It can’t go on forever. But I’m sure it’ll last until long after this column is forgotten.
Jonah Goldberg is editor-in-chief of The Dispatch and the host of The Remnant podcast. His Twitter handle is @JonahDispatch.