Leap Academy with Ilana Golan
Former Obama Foundation President: How to Lead Through the Toughest Moments | David Simas
Tue, 25 Mar 2025
David Simas grew up in a Portuguese immigrant family in Massachusetts. His mother, who lost two fingers in a factory accident, instilled in him the power of resilience and the importance of community. These lessons shaped his career, from practicing law to advising President Obama on key national issues and eventually leading the Obama Foundation, where he worked with global leaders to promote democracy and address critical global challenges. In this episode, David joins Ilana to share valuable insights on navigating political crises, leading with empathy, and maintaining personal balance during high-stress moments in public service. David Simas is a lawyer, political strategist, and former CEO and president of the Obama Foundation. He served as White House Director of Political Strategy and Outreach during the Obama administration and has held key roles in state and federal government. In this episode, Ilana and David will discuss: (00:00) Introduction (01:53) Growing Up in a Portuguese Immigrant Family (05:10) Family Struggles and Community Support (09:03) How Legal Training Shaped His Perspective (16:57) Transitioning from Law to Politics (19:44) The Call That Led Him to the White House (23:19) Why Obama’s Team Chose David (27:30) Giving the People a Voice in the Oval Office (32:11) How Great Leaders Handle Crisis (36:38) Balancing Humility and Authority in Leadership (40:28) Navigating Political Pressure and Public Scrutiny (51:12) The Power of Personal Responsibility David Simas is a lawyer, political strategist, and former CEO and president of the Obama Foundation. He served as White House Director of Political Strategy and Outreach during the Obama administration and has held key roles in state and federal government, advising on political engagement and policy strategy. He is currently the Managing Director of Research and Impact at Emerson Collective, where he focuses on democracy, immigration, education, and climate initiatives. Connect with David: David’s LinkedIn: linkedin.com/in/david-simas/ Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training
Chapter 1: Who is David Simas and what shaped his early life?
So my parents, who are still alive and still live in Taunton, Massachusetts, are two Portuguese immigrants. My mom grew up in rural southern part of Portugal. My dad grew up in the middle of the North Atlantic Ocean in the Azores Archipelago in an island called São Miguel, St. Michael. His village was probably 300 people, literally in the middle of nowhere.
The furthest that they went in school, their formal education ended at the age of 10. Hard workers, folks who left everything behind to start something new in a country that they had never been in. It is the American story, which is so amazing. And so the piece of Taunton, my hometown that stays with me, is I have a very vivid recollection of living in two cultures always.
When I went to school, it was as if I was going to America. When I came back home at the end of the school day, I was going back to Portugal. And when I went back home, the food was Portuguese. The radio was Portuguese music. My aunts, my uncles, my mom, my dad, my grandparents, my cousins, everyone was talking in Portuguese with an English
mixed in, but then you would leave and I'd be with my parents and we'd go to McDonald's or we'd go to someplace else. And it was this, I have a vivid memory of trying to like reconcile wanting to be American, but also being anchored and tethered to the very different way of being of my parents. And so that bicultural tension, that bicultural, how do I fit in? What do I retain?
Chapter 2: How did David Simas's family and community influence his values?
And I guess as many young people that have had that experience, I wanted so desperately to be American that I bristled. I didn't like the Portuguese aspect and wanted to leave it all behind until I was in my 20s and then now in my mid-50s. And oh my goodness, Ilana, that part of me.
That's a big part of you.
And I adore it now. It's something that's so, but that biculturalism and that desire to fit in was always something that I think to this day, I carry with me a little bit.
And I love that. I have the same from Israel. And I always wonder if I ever going to feel home in each one of them because I love both, but I have both. Right. And it's like this mix, which is beautiful. And by the way, my mom's parents all talk Portuguese. They came from Spain and Portugal. So we have a lot to talk about, but kind of funny.
But knowing a little bit about this culture and you'll share more, I think there's something about this culture of everybody helping one another and lifting one another. And I think you also have a really interesting story around that. Would you share a little bit?
They immigrate from Portugal and because they really don't have a formal education, they're working in factories. And my mother worked in a silver factory making forks and spoons and knives and silverware. And it was mostly women on her floor. And one day the machine malfunctioned. And just the way the machine was set up, she couldn't, even though she noticed that it malfunctioned,
you had a split second to remove your hands from the press. And the way the forks and spoons and knives are made is literally it would press down. And unfortunately for her, something impeded her ability to remove her left hand entirely. And in the blink of an eye, this young 20-some-year-old woman loses two fingers on her hands. And for them, all you have
are your arms and your hands and your back and your legs and the physical labor that you're using to build this new life. And everything was thrown at that moment
And I thank you for asking because what I remember so vividly was even though she was suffering and my dad was suffering, even though I was little, the memories of my family and my neighbors and to me, a little boy, this entire community at that moment in time coming to lift up my mom to lift up my dad gave you that sense of, at that moment of peril, at that moment when you fall,
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Chapter 3: What lessons did David Simas learn from his legal training?
They never once complained. I never heard them or my mom specifically complain about what had befallen them. If they did, they would close the door or never show their child, their son, or then their daughter, my sister, who was born, And so it was always this, okay, this terrible thing has happened. What am I going to do? What am I going to adapt?
I remember her doing physical therapy with a tennis ball where just for hours she would be squeezing the ball. Why? Because she needed to and wanted to get back to work.
Ah, so beautiful. I hope they hear this. And I think you bring that with you and we'll talk about it. There's a pattern there that keeps on that compassion, but not going into victim mentality, but staying victor. There's like a pattern that I see throughout your career that I'm sure that has a little bit definitely came from there. But let's fast forward for a second.
So you finished school and you studied law. What are some of those lessons from law school? Because one of the things, David, that I want our audience to hear is that even if you're not staying in law, there's so much transferable skills. There's so much transferable experiences that shape you to where you are going, right? So tell us a little bit and maybe a specific story that shaped you.
So the law for me, actually, it flowed from, I remember the person who represented my mother. And it was from that young age, I said, that's what I want to be. That's who I want to be. And I mean, he was physically like this very short man, but to me, he was this unbelievable giant. So from a young age, I wanted to be a lawyer.
But the biggest takeaway for me once I got to law school was the practice and the discipline of legal training requires the following. It requires a broad understanding of the basic rules and the structures, the system. It requires the regulation not to memorize them, but to have the ability in that moment when you need to, to go find it.
Once you have that understanding then of the rules, because you're dealing with different fact patterns that always arise, how then do I take a series of different facts
that are always up for grabs that it requires you to have a broad and open perspective about memory about recall about perception of the people you're dealing with and then take the ever-changing facts and apply them to the rules to the law to the structure and then most importantly either in writing or verbally, to make the case, to argue the proposition, to tell the story.
And so there are these three components that then I just saw after law school and after the practice of law, that this thinking, this approach is applicable everywhere because what do you do in any environment? What are the basic rules? What is the circumstance that I find myself in? How do I apply that set of circumstances against the rule?
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Chapter 4: How did David Simas transition from law to politics?
And he basically said, honey, do you know who I am? And I'm like, oh God, no. The truth is, beyond his name, I didn't know who he is. And it's a long story, but I will just say, knowing your audience is still probably the most important lesson that I learned from that day. I'm like, oh, darn it, because I said the right thing. I should have said it differently.
I love this story and how it ties into everything. you then eventually go to politics. And I want to understand why do you leave law and, you know, I mean, for everybody in the political, you know, they're trying to get into anything politics, like White House is like a dream. So share a little bit about that story.
My parents, Portugal, when they were being brought up, was a dictatorship. Antonio Salazar was the dictator, had been the dictator for decades. There was secret police all over the place. And so they didn't have an understanding or an appreciation for liberty or basic ideas of freedom or democracy.
And so when they immigrated, especially my dad, oh my goodness, we would watch the news every single day. I remember reading the newspaper with him as a little boy. And it would always be the mindset of a citizen as someone who had a voice and had a responsibility to be informed and to participate. And when he would talk about it, there was a reverence to it.
that was informed by the experience that both he and my mother had come from. And so for me, politics was always this ultimate expression of the sovereignty of the people. And oh, I just followed all of it. I remember being a young man. My father was a very conservative Republican. And so Ronald Reagan was the epitome for him.
But I remember one day where he was saying wonderful things about the governor of New York, a man named Mario Cuomo, a liberal Democrat during the era of Reagan. And I said to him, I'm like, Dad, they could not be more different. And he's like, well, that's kind of where you're wrong. Have you ever listened to the way they talk about this country?
Have you ever listened to the way they talk about the promise of this country? And that when you listen to the poetry of a Mario Cuomo and the poetry of a Ronald Reagan, The means to get there were different. And so I just fell in love with that.
So I ran for office when I was a young man and it just began the political career of engaging that all of a sudden ended up in a crazy way with, it was the inauguration of Barack Obama. I had not worked on the campaign. I had been working for the governor of Massachusetts, a man named Deval Patrick. My wife and I were in Washington. All of a sudden, my flip phone rang. I answered it.
And there was a man who was purporting to be David Axelrod, the chief advisor to the president of the United States. And I thought it was a joke. He's like, this is David Axelrod. I said, yeah, right, I'm Barack Obama. And he said, no, you're not. I was just with him. I said, oh, blank. And I said, how can I help you? Aren't you busy?
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Chapter 5: What was David Simas's journey to the White House?
And I got the job and it began a 14-year relationship with the president, which is amazing.
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And I will see you in the next episode of The Leap Academy with Ilana Golan Show. David, I want to go there for a second because that's one of the most incredible stories. Do you know why they reached out to you? How did you build that credibility, that authority, that reputation for yourself? And I want to make sure that our audience gets it. These kind of jobs are not on the hiring boards.
Everybody gets that, right? It's all in the hidden market. It's who knows you. And it's according to what you want to be known for. So how do you think you were able to build that kind of reputation to be the person that somebody like this calls?
It only happened, obviously, because my boss, the governor, who had known David for a while, vouched for me and vouched for his assessment of my capacity to work, but also his assessment of who I was as a person. A few months after, when I finally asked David, Axelrod, hey, man, I didn't work on the campaign. I didn't go to an Ivy League school. I went to Stonehill College, a commuting school.
I'm a lawyer. I've been in politics. I've never been and worked in Washington. Why me? And essentially his answer, I'm paraphrasing, was that's exactly why. Because what he wanted, what he needed at that moment was someone he trusted implicitly, vouched for from a character and a work ethic perspective, who had never been, tainted is the wrong word, but too immersed in the culture of Washington.
Still had that outsider's perspective. And because of my background in politics, and I think the thing that was most interesting to David, when I ran for office when I was in my early 20s, And in running for office, what I did was I knocked on thousands of doors and had hundreds of conversations, mostly listening to people.
And then you take what you're listening to and you engage with them, both in a conversation, but then to inform how you're gonna approach, if you win, the process of governing. And so what I found out was He wanted someone with a fresh set of eyes who understood politics at the most basic neighborhood, interpersonal level, because, and this is one thing that I learned in love,
To this day, the overwhelming majority of people do not approach democracy, the American Republic, governing or politics via an ideology or a set perspective. Some do. Those are the partisans. But most people are living their lives. They will check in periodically, and they want to make sure that the people that they put in charge are listening to them and connected with them.
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