Johanna Maska: A Role Model for a New Generation of Women on how she grew from Galesburg to the White House to Financial Technology
Interviewed by Ari Ratner
Tell me about your experience growing up.
I grew up in Galesburg, Illinois – President Obama talked about Galesburg in 2004 when he was running for Senate and spoke at the Democratic convention. He talked about this place where the workers at Maytag lost their jobs in a pretty devastating blow to the local economy.
Galesburg is a blue-collar place. I grew up working for my dad at the Pizza Hut. He taught me a lot about the benefit of hard work. I wanted to go away to college. My parents hadn’t finished college, but my grandmother had. She offered to help me visit the University of Kansas. When she offered me support if I went there, it was the only place I applied.
I loved the University of Kansas. I was an honors student, I worked in Student Senate and I worked at the student paper. I made friends with my professors and had this awesomely supportive optimistic place that motivated me to be what I wanted to be.
So after graduation, you entered politics?
As graduation approached I remember reading “What Should I Do With My Life.” People in the book found what inspired them and chose that as a career. I had always loved politics.
I always say I came out to my family as a Democrat. It was Christmas after George W. Bush was elected. At a dinner of 40+ I told them all they’d regret this. It was not well-received. One colorful uncle pulled my dad aside afterwards and said, “Your daughter has balls, Mike.”
I finished college at the same time Kathleen Sebelius was just elected a Democratic Governor of Kansas. I was a big fan. I found connections to get me in the door, I volunteered to do anything. They agreed to bring me in, first in constituent services, then as an assistant to the press secretary.
There’s a lot of talk about how millennials enter the workplace expecting to run the place, but I actually think many of us recognize we all have a lot to learn. I entered Governor Sebelius’s office as one of the youngest staffers. She had a fabulous group of people who surrounded her in Kansas, friends who had helped her work her way up. I remember one of the women had a cartoon in her office pulling up to her grave saying, “Boy that was one hell of a ride.” They taught me to ride the waves and stay afloat, good times and in bad.
So how did you make the jump from Kansas to Iowa, where you worked for the Obama campaign?
My husband - then fiancé - was offered a job in Iowa. A friend of ours encouraged us saying we’d love Iowa. And we did.
He went first and I followed, I got into the political scene there thanks to friends. My friends were involved in a Gubernatorial campaign for Mike Blouin and Andy McGuire. I worked closely with both Mike and Andy. It was fun. And I love Andy, still keep in touch. She’s a doctor who had 7 children and a great story. We lost the campaign. And in that, it was the best lesson that I could have learned. It was a family fight, a primary campaign, I was early in my Iowa political days. I decided I’m not going to work on another campaign until I found the right candidate.
But you found the right candidate, in Barack Obama?
I had been paying attention to Barack Obama from the moment he emerged on the scene in 2004. I watched the 2004 Democratic Convention speech he delivered on TV. He was talking about my hometown, Galesburg, he was talking about his family’s Kansas values. At the end of it I was standing up in my living room screaming – I was like, “YES! I want to work for him!”
My husband is a political reporter so he follows the personalities involved and in 2006 the then-Senator Obama came to the Harkin Steak Fry. My husband said “If you’re really interested, Hildebrand-Tewes seems to be involved. You should get to know them.” Well, the opportunity came in December: It was rumored Paul Tewes was moving to Iowa to be Obama’s Iowa director. So at think point I’m thinking, “Okay, Obama’s running!”
And so, I set it out ‘stalking’ Paul Tewes, hoping he would give me a job. Paul laughs when he tells the story now. We met at a party of a friends and I said to Paul “I am so thrilled you’re moving to town. It’s so nice to meet you, where are you going to live?” And he said, “The 10th Street Lofts.” “That’s where I live!” I said – It really was, I wasn’t making it up. I asked him, “What floor are you going to be on?” He said the 5th floor and I was also on the 5th floor. I was sure this was fate.
You worked Advance for Obama in Iowa. What was that like?
Paul tells the story that he didn’t have a job to give me and he knew I would keep harassing him about it. It got to the point he’d go to the 4th floor to take the stairs up knowing he could better avoid me as I was right by the elevator. But I wasn’t going to give up. Finally he said, you’re going to do press advance. And put me in touch with the folks to make that happen.
I’m so lucky he did. In Iowa I worked with a group of men who had done advance for what felt to me like the newbie for forever. I had only done press/communications. But they helped me learn the ropes, and I got to see history unfold. I traveled for a long time as the only woman of the Iowa advance team to random corners of Iowa. We’d go to retirement homes, into community centers to get folks who wanted to hear from the then Senator Barack Obama. We would find little show barns at the state fairgrounds or the county fair grounds all across Iowa and we’d try to get people there to hear for town halls. There was some reluctance. Many might remember at this point in time his middle name was definitely Hussein, he was relatively new and Hillary Clinton was getting all the press attention, so everyone assumed she was going to be the nominee.
I had no idea before working in Iowa, the value of the Iowa caucuses or the New Hampshire primaries to the overall general elections. But the value is that voters there are seasoned and that they take it so seriously; the vetting process that they do for these candidates is more than awe over celebrity status. They truly ask them, “What are you going to do for my family?” with variances in the situation at hand.
So here in Iowa, people were skeptical. Obama didn’t emerge with the same kind of adoration that I had for him to everyone in Iowa.
What do you think were some of the keys to winning tough states like Iowa?
Have you heard the story of “Fired up, Ready to go”? For those who don’t know the fired up ready to go story, there was a small event in South Carolina and the President was asked to go by the local official and he didn’t really want to go. He gets there, it’s a rainy day and he had travelled so far away and there had been a bad story in The New York Times about him and he was so frustrated and he didn’t want to be there and he goes to talk to all these people and this little lady in a church hat in the back starts yelling, “Fired up, ready to go! Fired up, ready to go! Fired up, ready to go!” and he said, “Before long, I’m feeling a little fired up! I’m feeling a little ready to go!”
He used that story to create a movement. “If one voice can change a room, one voice can change a county, if it can change a county, it can change a state, if it changes the state it can change the world. Let’s go change the world, everybody.” I must have heard that story live and in person more than 100 times. And I’m so lucky for it.
Slowly but surely we were picking up steam. It was right before the Iowa caucuses that the Des Moines Register poll came out, we were ahead; we were going to win according to the Des Moines Register. And Paul Tewes called everyone, in a staff meeting – I think it was a little after midnight – and Paul said, “Polls don’t vote. This doesn’t matter. Every single person has to get to the caucus location tomorrow or we don’t win.”
Hearing an election result can be a funny thing. You have no idea what’s going to happen. After I finished caucusing myself (as a resident of Iowa, I could), I got on my radio for election night and I heard the announcement that we won. It was the most incredible feeling. We had done it.
Tell me about the re-elect. What was it like helping run logistics for the President of the United States during a major milestone of your life— your first pregnancy?
Yeah. Well, so the re-elect was interesting. I was in this position where I was planning the logistics for the President, while I was expecting my first child, my little Hugh, in March of 2012, before the re-election. My husband and I were so excited. We were thrilled to have this little baby, but there was a lot of uncertainty.
I had a colleague Emmett Beliveau whose wife gave birth to his daughter the night before election night in Grant Park. He went the hospital, welcomed his daughter, came back to the site to brief Secret Service and finished that event leading the election night. When I got pregnant, I didn’t want to give up my job either. Alyssa Mastromonaco reassured me, “We did it for the boys, we’ll do it for the girls.” I was determined that I could continue doing my job. I kept on. I think it was Ben Rhodes who would joke, “Isn’t Johanna 15 months pregnant now?” I love that. I probably looked it. I was at Camp David riding golf carts planning the G8 the Thursday before I delivered my son the next Monday.
I went into labor on a Sunday night. We were hosting NATO in Chicago soon after. I was in a debate about credentials. I’m sure this email is archived somewhere but I was going back and forth with them and finally now I was in labor. I wrote an email that said, “I’ll keep this brief because I’m in labor,” then something to the extent of we need to control credentials. I won the argument. Ultimate trump card.
And after you had Hugh? How did you juggle that?
Hugh was born on March 12. We had subsequent plans that I was unaware of, to go to Afghanistan to mark the one-year anniversary of Osama Bin Laden’s death and do a live address in the nation. Dan Pfeiffer and I had worked on projects like this before, and I think he knew he could trust me. I’d brought Hugh into the White House at 3 weeks after I had him so folks knew I was around. Danielle Crutchfield called me and asked that Dan was hoping I might be able to help. It went something like “Whatever you’re comfortable with. I know we could really use your help.” So seven weeks after delivering Hugh I ended up on a plane to Afghanistan.
In the lead up, I would take Hugh to work, and I didn’t have a nanny, I didn’t know I was going to be at work and I didn’t have childcare arranged. Occasionally when I had to be in a secure call, I’d just give him over to one of the schedulers and say, “Hey, can you watch Hugh for a minute?” A couple other meetings I would host in my office or bring Hugh along, the military guys would come in and Hugh would be in the corner and they would end up planning the logistics for this live address to the nation in Afghanistan with a sleeping baby in the corner. Most of them loved that. I certainly did.
Wow. You worked as Director of Press Advance for years. How did you manage the transition from working in the White House?
We get to the second term and I know now the time is ticking. I remembered my Bush administration counterpart waving me in as I was helping with Inauguration at the White House. I said, “What are you going to do next.” He said, “I have no idea.” I thought – That’s not going to be me. So I had to figure out what was next.
To be honest, this was probably the most challenging time for me at the White House. I absolutely loved what I did and the thought of moving to something new really scared me. But my son was talking now, asking “Mommy, I don’t want you to go.” And I didn’t want to go anymore.
I asked a lot of people for help. What was most interesting to me was how technology over the course of the administration had really changed the landscape.
Can you give me an example?
I remember going to South Africa for the President’s visit; we did the pre-advance. In the pre-advance trip you go and you scout a bunch of places the President could visit. The President will never go to most of these, but the host government may want to show you, or the embassy may want to show you, so it’s your job to visit them.
We went to a lot of really poor communities in South Africa where they don’t have plumbing or access to showers, but at these community centers, all these kids had iPhones. People are communicating, they’re connected, they’re learning so much. In a tech center in Ramallah, kids had hope. They wanted to be the next Mark Zuckerberg.
How did you figure out what was next?
I had decided to go to the LA Times. The CEO and Publisher had a simple mission: He wanted journalists to be able to cover the local news, good and bad, and have a business model to support it. He wanted to use new digital tools at a legacy brand. I was a journalism student in college, I loved what he was trying to do. I had decided to go to the LA Times right before I had a trip to Silicon Valley planned. I had met a fabulous woman who has become my dear friend, Sherry Harmon. She had grown companies from nothing to brilliance and she told me, you started at the beginning of the Obama campaign. You started when he was a start up. You’d really love this world. She helped me connect with some brilliant folks. And right before I met them, in my mind I’d already decided to go to the LA Times. When I told them what I was going to do, they looked at me like I had two heads. Going to a legacy brand.There was one meeting in particular that gave me second thoughts about my path. A very smart investor told me his theories on technology and innovation and having seen the changing world, he was spot on. At the end he encouraged me to look at the fintech space. If it’s done right we open up economic opportunity for millions. I told him I was going to the LA Times. He said he would support me, but that wasn’t where I was going to end up. How right he was.
Can you tell me more about your experience at Karmic Labs? What have you learned about the financial tech industry, and more broadly, about being a woman in an industry traditionally dominated by men?
We glossed over the fact that I did go to the LA Times. It’s all you find on the internet as you mentioned. It’s funny. I spent 8 years off the record working for President Obama. I spent 4 months at the LA Times and that’s what’s on the internet. I think the media loves to cover themselves. But I actually learned so much so quickly about being a woman in business there. Folks react when you give your opinion. And in a different way than if a man says the same thing. I loved working with Austin Beutner because he brought fabulous people, including women, together and empowered them. It was a great experience but without Austin and his vision, I was going to move on.
When I moved on I went right back to the friend of mine who talked about financial technology and reignited the conversation on what he suggested. I joined Karmic Labs, an awesome early stage fintech company with a fabulous product that gives people more economic tools to make better choices in card solutions tied to apps. Karmic has the opportunity to help define the modern payment stack.
I’m new to the fintech space but I benefit from being surrounded by a team of old pros. Folks who built SOFI, Venmo, worked for AMEX, Visa, Wells Fargo, FIS Global, the first engineer from Pinterest (I’m obsessed with Pinterest), one of the engineers who built Netscape. Karmic is Greycroft funded. Greycroft you should know because they bring great ideas into reality, like Plated, My Domaine (I love that company), even the Huffington Post. These tech companies are giving us awesome tools. Connecting our society so that in something like Plated, I can have healthy meals ready for my son and do the work I love. At Karmic Labs I’m really lucky I found a CEO who thinks outside the box and a company where they’ve built an awesome product that few folks know about. I get to market our products, pitch the company, communicate with users. Make sure people know about it. Much like I did in early days trying to make people pay attention to the then Senator Barack Obama.
At Karmic Labs, we have this card program, you know, it’s kind of like Venmo for businesses with cards. You can transfer money to the person who needs to spend money in real time, ending reimbursements. I had for years, been fronting my own money for the Obama campaign and for the government, and waiting for a reimbursement. Our card options are cool. The cards are tied to a mobile app that for an organization allows them to transfer money to the card they need in real time. As soon as the money is spent it gives complete information about the transaction. The employee takes a photo of the receipt and an organization has complete oversight of their expenses. It’s so intuitive. It’s so much more fair than reimbursements. And the technology gives complete oversight. We give people more for less.
I’m very lucky to again be surrounded by motivated people who expect to grow something great. Start-ups are much like campaigns. They grow from zero to thousands over the course of weeks and months. They work to create something great for people and give them more tools to empower them in business or in life. I’m loving it.
I’m loving it so much I’m co-founding the Women’s Advisory Council in San Francisco with a group of women entrepreneurs determined to bring diversity to early-stage companies. I’m so lucky to have found a fabulously supportive environment. And I think that’s all any of us can hope for.
I think what’s most important is as we as women grow in our roles, we find every way to tell other women they can do it too. Women at a young age need to be told “You’re good at math, you can excel in this field. You can be a CEO. You can be all those things.” I wouldn’t be where I am today if not for women and men telling me I’m going to be great at what I’m doing and helping show me the ropes. All I can hope now is that I continue learning while passing along a little of what I’ve learned to the next generation.
And that’s where I’ll leave my last thoughts. I’m really lucky in my life. I’ve gotten to do some extraordinary things. I’ve flown over Petra in King Abdullah’s helicopters. I’ve toured the pyramids in Egypt with the President of the United States. I went to Robben Island in South Africa and saw Nelson Mandela’s prison cell with the first African American President who I worked tirelessly to ensure his election. I’m incredibly lucky to have been privileged to see so much of our history firsthand. But the best thing I’ve ever done is have my son. In having a child, you see everything in fresh eyes, the joy of the little things that make life great, and you get to impart a little of what you’ve learned to them.
Ari Ratner is the Founder and CEO of Inside Revolution, a boutique strategic communications firm. He worked with Johanna Maska on President Obama’s 2008 Presidential Campaign and the 2009 Presidential Inaugural Committee.