He graduated from Lyons Township High School and Middlebury College in Vermont (’03) where he majored in political science and served as president of the College Democrats.  He made his way to Washington, working as press secretary for Congresswoman Jan Schakowsky, press secretary to Ohio’s Sherrod Brown in his first U.S. Senate race, press secretary to Illinois’s new senator, Barack Obama, back here as communications director for  Rahm Emanuel during the 2011 campaign,  and then his biggest job, national press secretary for Barack Obama during the 2012 reelection campaign.

Like legions of smart political operatives before him, he’s now settled in DC where, last year, he cofounded (with Robert Gibbs, Obama’s White House press secretary during the first half of the first term) the Incite Agency, a political strategy and PR firm that advises advocacy organizations, non-profits, and  Fortune 500 companies. (Incite advises the latter “on how to transform communications… defend brands under siege and tackle significant customer and public policy initiatives.”)

On a visit home to see his parents—his mother in La Grange and his father in the city’s Edgewater neighborhood—LaBolt, 32,  met me the day after Christmas at Chicago’s offices.  I recognized him immediately in the lobby of the Tribune Tower having seen him recently on Fox News’ The Kelly File arguing with Megyn Kelly about Obamacare. (Predictably, Kelly could find nothing right with the law and LaBolt could find nothing wrong.)

Dressed in jeans and a preppy blue Lacoste sweater over a blue checked shirt, LaBolt is good-looking and loyal, a nice guy seeming to lack the usual harder edges of people who climb the DC ladder as quickly and surefootedly as he did. He says he has no intention of returning to the campaign fray and is enjoying the more settled life as a DC PR/strategy man. He adds that he misses Chicago’s neighborhoods, restaurants, and cultural offerings, but professes no desire to return here. He’s single and lives in the District’s historic—for jazz and blues—U Street Corridor.

Here’s an edited transcript of our conversation:

I’ve seen you a couple of times politely answering Megyn Kelly’s aggressive criticism of the ACA.  I laughed when she patronized your defense of Obamacare with,  “Stop that. You are too smart to believe that.”

I’m eyes-wide-open going into that. I don’t think Democrats should just appear on friendly territory. Fox has a very large viewing audience for some of their shows; two million people get to hear a different viewpoint every once in a while.… I’m always open to doing Fox if they’re clear about what the topic that’s going to be discussed is; clear about what you’re signing up for and you’re actually going to have a dialog on the show, don’t just get talked over….I  think it’s important not to just sing to the choir all the time… Also, remember, there are independents who watch [Fox]. We took a look at that during the campaign.

Any interesting experiences in the green room?

I’ve bumped into Karl Rove—we had contiguous segments—but that’s the DC experience. It’s a smaller town than you think,  and you overlap with a lot of people you see at events…. We joked around about our different viewpoints. I’ve never met anyone [there] who’s been unpleasant.

Growing up in La Grange, what sparked your interest in politics? Were your parents political?

It’s in your blood if you grow up in and around Chicago.  Big personalities, one of the last cities left with a political reporter at every TV news station, and there are four stories in the paper about the mayor every day. Politics always mattered and you could always tell that it mattered. My parents weren’t involved in politics day to day—they were democrats–but they read the Tribune religiously.  I would read it after my dad read it at breakfast.

Your political activity started in college?

In my first year, Howard Dean was governor and had just passed civil unions, first state in the country, and there was a really nasty gubernatorial race that year against Dean. I just volunteered. It was also a presidential election year, so we’d drive down to New Hampshire during the primaries. We’d also do things like put together a phone bank for the local state rep candidate. A winning margin in Vermont is something like a thousand votes,  and so if people at my college came out and voted that was the margin of the campaign, and so it was fun to work on something so small where you knew that if you engaged X number of people you would tip the results of the race.

When I got out of college my first job was working on the New Hampshire primary [in 2004] for Gov. Dean. 

Did you consider another line of work than politics?

I always thought I’d go to law school, took the LSAT in college and at some point I just decided I found my career and I didn’t need to get a JD and spend the next five years editing briefs at 3 am working to pay off my loans.

How did you and Robert Gibbs get together? He’s older and better known.

Robert hired me in [early] 2007 just as Sen. Obama made the decision to run [for president] and he and the other person in the senate office who managed communications there, Tommy Vietor, both headed out to do the presidential campaign, so they needed somebody to do the day-to-day communication in the senate office.

At your new venture, Incite, do you and Gibbs lobby?

It’s strategic communications, and so the vision for the business is to apply all the different communications strategies that we learned on campaigns and in the government to a variety of organizations. They might be companies; they might nonprofits or causes or foundations; or they might be campaigns.

Do you work with Republicans as well as Democrats? Would an organization with a conservative bent come to you?

If somebody is pursuing an ideologically conservative agenda, that wouldn’t be a good match for us. On the business side [we work for them] unless they’re engaged in something we wouldn’t want to be engaged in. If they have a basic business agenda and we can help them structure their communications…. A lot of Republicans have reached out to us because they already have the Republican perspective in the room and they wonder if we approach something in a different way or if there’s a lesson we learned on a campaign… that they could use to their benefit.

Firms like yours almost always seem to have a Republican and a Democrat at the top.  Does Incite have any Republicans?

We don’t have a Republican on our staff at this stage, but I think that’s largely because we’re so small—five professionals—and just starting. I imagine we will some day. That’s certainly important, particularly important for a lobbying shop, and we’re not a lobbying shop, but I think that’s the sort of team we’d like to build in the long run. I think we will have a Republican on staff.

Do you work for particular candidates; for candidates running in ’14?

Not full-time, but we’ve dabbled, such as helping out Democrats who are supporting education reform.

Do you miss working on campaigns?

It’s different. There’s a certain adrenaline that comes with that, and the experience of the team is always rewarding.  But it takes up your entire life and you’re never sure if you could take a trip or go to a wedding or even go out to dinner, so it’s nice to be not as attached to something like that. At the same time, I stay in close touch with people in politics day to day.  I know that we’ll be involved politically in a number of projects, as mentioned, helping out democrats with education reform, so it feels like I have a foot in both worlds right now…. My two top priorities politically in the next couple of years are seeing democrats keep the senate and seeing the mayor reelected here.

Is it possible you’ll leave business and get back into politics?

I think I can do both right now. I don’t feel like I’ve completely left and I think that’s a good place to be.  I don’t see myself sitting in-house for two years ever again. I think I’ll hand that off to the next generation of people that has the energy and motivation to work those 18-hour days for two years. I’m happy to be the guy that comes into town and takes everybody out to dinner and offers some advice, but no I don’t think I’ll miss the constant activity and commitment.

I was surprised when Robert Gibbs publicly criticized the ACA rollout and called for someone to be fired. Is there some bitterness between him and Obama dating from Gibbs being marginalized during the ’12 campaign?

Not at all. NBC hired Robert to be an analyst, not a surrogate, and to give a frank assessment of what’s happening in the news. And secondly he was frustrated that there were staff that did a disservice to the president on his signature accomplishment, a big piece of his legacy.  There were a lot of people looking at the ACA as a test of what government can do, and the people who worked on the web site failed in that process…. I think Robert felt like that. I don’t think there’s anybody at the White House who disagrees with that assessment.

So how did it happen that Obama knew so little about the kinks in the system that resulted in the launch blowup? Staffers not wanting to be the purveyor of bad news, or the President’s mind being elsewhere?

I think a couple of things. One, it isn’t clear to me that the people who produced the website offered accurate reports as to its functionality. Second, there were too many people involved in the bureaucratic process of developing the site. There were 55 contractors involved and there were a bunch of people in charge, when they should have filtered out to one person who could really do what they do in Silicon Valley when they’re reviewing a new web site, which is have as many people test it out as possible to figure out what the errors are in the site and then learn from that….

I think the hole in the operation was not having one person designated to be the person responsible for ACA implementation…. You have to have a more efficient, transparent accountable process where you catch errors along the way…. The biggest surprise of going to work in the White House is after the President has made a commitment to something and after a law has been passed there’s still a number of bureaucratic barriers within the executive to getting that thing done. 

I still don’t understand how President Obama knew so little; it seems like he was expecting it would work well.

It seems clear to me that people were reporting up that it was ready to go: the Travelocity of websites for healthcare. Nobody wants to disappoint the President, so… somebody communicated a report about functionality that whitewashed… what was going on with the site, or they tested it insufficiently to know what the errors were…. At the end of the day what’s going to matter is how many people enroll and are they satisfied with their health care and do health care costs general go down.

How long will that take?

That’s the political question, right? Does that happen by November 2014 or does it take more time? 

Should the President have fired Kathleen Sebelius?

Remember all of this was before the Senate nomination process was reformed and so if he’d gotten rid of her there would never have been another HHS secretary confirmed in this senate, so I think doing it at that time would have been a mistake. I also think it’s wrong to jump to conclusions about who was at fault until you’ve really seen the report, whether that’s a congressional report or IG report about who ultimately was responsible for the oversight of the process and the contractors. I don’t feel qualified to make an assessment.

Is bringing in John Podesta a good step?

Absolutely. I think it was a very tough year for the President. Nobody sugarcoats that and getting a fresh set of ideas from somebody who built the smartest Democratic think tank in Washington [Center for American Progress], has a ton of policy ideas, and also somebody who came in toward the end of an administration [Clinton’s] when we were able to get less through Congress and still made progress on the agenda.  [LaBolt refers here to Podesta’s penchant for bypassing congress through the use of executive orders.]

Politico’s  Glenn Thrush reported that Podesta has a temper so scary that “even the brash Rahm Emanuel scrambled for cover.”

Let me just say that I’ve never seen Rahm take cover…I loved working for him. I’d kill to have a mayor like him in D.C.  I thank god when my garbage gets picked up in that town. He has great political instincts. Everybody knows that, but he’s also a lot more of a policy wonk than a lot of people think. He’s somebody who has 15 ideas about what to do before 6:30 every morning… limitless energy; more energy than anybody on staff.

Does he have national ambitions?

I don’t think he does. I think he loves the city too much to leave it. I think he thinks being mayor of Chicago is the greatest job in the world and he’s able to spend all day doing his job, but then be home with his family, raise them, and eat at some of the best restaurants in the world and go out and see music or a play at some of the best places in the world, and I don’t think he has interest in leaving that.

I see many similarities between Michael Bloomberg and Rahm.

One of the big similarities is they’re both very outcome-oriented, so rather than being ideological for ideology’s sake, it’s looking at what are the top three problems in the city and who’s the person in the world who knows how to solve that problem the best.

I also think they have extremely strong networks and personal relationships. It’s interesting that clout is a bad word but it’s not a bad word anywhere else in the country. It’s a bad word for a good reason in Chicago… far too much corruption in this city for far too long, but I think the Mayor’s personal relationships that have allowed him to get major CEOs on the phone to move businesses and operations here and his relationships around the world have enhanced the status of the city.  So in that way I think the Mayor’s personal clout has been helpful because  he won’t take no for an answer and he’s got all these relationships with elected officials and business leaders and cultural leaders in the US and around the world  that I think have benefitted the city.

Were you ever on receiving end of his temper or profanity?

I think a lot of that is legend and I think he has probably calmed down over the years. I think what’s interesting is the fact of how long people work for him and how loyal they are to him. I think that’s because he treats his staff with respect. I think most people who worked for him also respect the fact that he’s not a BS artist. If someone’s coming in and telling him time and time again that they’re going to do something that they have no intention of doing he’s stops them right there.

He’s obviously running in ’15 and I see him staying for maybe two terms.  Do you see him as a Rich Daley or a Richard J, as being mayor for life?

I think he could be if he wanted to, but I don’t think being mayor for life is his intention.

Two-term mayor?

I don’t know the answer to that and I’d be surprised if he knew the answer to that. But he ran at a big transition point for the city. He ran on a tough-love message of addressing the big challenges that the city was facing that hadn’t been addressed—the economy, the deficit in particular, and crime and schools, and I think he’s maniacal about making sure that those three things are addressed and I don’t think he’s gonna rest or stop until he feels like we’ve made significant progress in all those ways.

Daley has become the great villain in the reporting about Chicago. He has taken a dive in public opinion here like I’ve never seen before. Bigger dive even than someone accused of corruption. He’s accused of, in effect, planting flowers while Rome burned.

I think it’s framed like that in the press…. For people like me who grew up with him being the mayor he will always be a legend. There are few people who think that the city would be as much of an international city and have reached the heights that it did if he hadn’t been mayor. I think the current mayor has a lot of respect for him.

Did President Obama want Rahm out of the White House? 

I think the timing of Rahm’s leaving the White House was the surprise decision by Mayor Daley not to run again, and I think the President has said many times that the only person who could have gotten his very ambitious agenda—Recovery Act, Affordable Care Act, Wall Street reform—through Congress was Rahm. He’s the only person who had the relationships and the tenacity to get that agenda through.

During the mayoral campaign, did you and Rahm’s other staffers worry about the residency issue, especially when the judge’s ruling came down?

There’s potential peril involved and it was important for the mayor to project confidence, but the best chance anybody had to beat him was to make sure that he didn’t run at all, and so it was strange dragging us political professionals into a court room…. Ultimately I think that was a disservice to the city when we should have had a five-month dialog about education and crime and pensions and the deficit.  And it turned the mayor into a victim because of old school, brass-knuckled political tactics trying to drop him from the ballot.

Mrs. Rahm, Amy Rule, has a very limited public role.

I think she has always been a very private person who focused on raising a family. That being said I think she’s gotten into the job of being first lady, particularly with her organization that helps out students from underprivileged backgrounds get internships and help with long-term education and career prospects.

She seems the opposite of [New York Mayor Bill] De Blasio’s wife who really is in the mix.

I think [for Amy Rule] it’s less photo-ops but more sort of substantive work on the issues that matter to her.

You mentioned before that you read both Chicago papers on line—and extremely thoroughly. Are there reporters here whom you particularly respect?

I think the model political reporter is Dan Balz (of the Washington Post); the sort of gold standard of Washington political reporters, ….if you want someone who is fair and impartial.

What about the Sun-Times and the Tribune?

Lynn Sweet is a legend for her relentlessness. I remember a couple of press conferences when I was working for Sen. Obama where she was sitting under the podium clutching the podium shouting questions from under it. Plenty of good reporters at the Tribune, Christie Parsons, Rick Pearson.

You’ve worked for lots of politicians. You have a favorite?

Obviously it’s a singular experience to have been on the ground floor of electing the first African-American president.  If I look back at the end of my life that would be at the very top of any list that’s made. I had a blast working for the mayor here because he’s such a dynamic personality. He’s so filled with ideas and so ready and willing to go act on something.

Did you sign up for Obamacare?

No, I have employer-based health care…. I was on the individual market earlier this year with one of those crappy plans, catastrophic coverage. Had I remained self-employed I would have gone on the exchange and it would have been, I assume, better than my individual market plan. It wasn’t very good and you have to fill out a 30-page medical history just to qualify.