The Chris Voss Show - The Chris Voss Show Podcast – 100,000 First Bosses: My Unlikely Path as a 22-Year-Old Lawmaker by Will Haskell

Episode Date: April 17, 2022

100,000 First Bosses: My Unlikely Path as a 22-Year-Old Lawmaker by Will Haskell The underdog story of Will Haskell, who became a Democratic state Senator in 2018 at age twenty-two—taking on an incumbent who had been undefeated for Haskell’s entire life and earning an endorsement from President Obama—and is determined to pave the way for his peers to transform government from the bottom up. President Obama left office with these parting words for Americans: “If you’re disappointed by your elected officials, grab a clipboard, get some signatures, and run for office yourself.” Twenty-two-year-old Will Haskell decided to do just that. If he ran for office and won, he would become the youngest state Senator in Connecticut history. For years, Haskell’s hometown had reelected the same politician who opposed passing paid family leave, fought increases in the minimum wage, and voted down expansions of voting rights. Haskell’s own vision for Connecticut’s future couldn’t be more different, and he couldn’t stand the idea of an uncontested election. In 2018, he would be a college grad looking for his first job. Why not state Senator? When Haskell kicks off his campaign in the spring of his senior year, he’s an unknown college kid facing a popular incumbent who’s been in office for over two decades—as long as Haskell’s been alive. Haskell’s campaign manager is his roommate and his treasurer is his girlfriend’s mom. He doesn’t have any professional experience. But he does have a powerful message: there’s no minimum age to being on the right side of history. Six months later, Haskell’s shocking upset victory gives him a historic seat in the state Senate and the responsibility to serve the 100,000 constituents in his district. Like any first job, his first term as a legislator is filled with trial and error. Creating a program that funds free tuition at Connecticut’s community colleges—nice work. Falling asleep on the senate floor—needs improvement. In the tradition of Pete Buttigieg’s Shortest Way Home and Greta Thunberg’s No One Is Too Small to Make a Difference, 100,000 First Bosses is the story of how one twentysomething candidate waged the campaign of his young life, fought for change at the state capitol, and proved that his generation is ready to claim a seat at the table.

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Because you're about to go on a monster education rollercoaster with your brain. Now, here's your host, Chris Voss. Are you ready to Chris Voss? I don't know what the hell that means. Hey, guys. Welcome to the show, thechrisvossshow.com. Thanks for tuning in on this beautiful Friday. It's a Friday.

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I've been a CEO for, what is it, like 33, 35 years now. We talk about leadership, the importance of leadership, how to become a great leader, and how anyone can become a great leader as well. Or order the book where refined books are sold. Today we have an amazing gentleman on the show. He has an amazing story and a brand new book. Who saw that one coming? New books coming out.

This is a book that came out January 18th, 2022. You can get it in all different formats. The book is called 100,000 First Bosses, My Unlike unlikely path as a 22-year-old lawmaker. And we're joined today by Will Haskell. He's an amazing young gentleman, and he is an American politician and member of the Connecticut State Senate, representing District 26. The district includes the town of Redding, Redfield, Wilton, and parts of Bethel, Weston, Westport, and New Conn.

I'm not sure if I'm pronouncing that correctly. But what's interesting is he's not only very young, but he also, his district had not been represented by another Democrat since 1973. And he took over some incumbencies in 2018 and again in 2020, holding the seat, which is pretty amazing. I think his story is amazing as well. So Will, welcome to the show. Thank you so much for having me, Chris. Such a pleasure to speak with you. Thank you very much for coming. So give us your plugs, your dot coms where people can find you on the interwebs, please. Sure. Will Haskell for CT on Instagram is my favorite social media platform. I try to use it to give people a behind the scenes look at what actually happens in state government, what it looks like for a bill to become a law.

Will Haskell, CT on Twitter. Folks are welcome to contact me through my website as well. I really believe that the job of an elected official is to be accessible to the public. So I spend actually a huge chunk of my day writing back to the folks in my district and keeping them updated on my work on their behalf at the state capitol. That's always smart. All politics are local, as they like to say. So what motivated you to want to write this book? So every few months, I would get a call from a young person who wanted to run for office. They

were in Alabama and wanted to run for a Board of Alders seat. They were in Florida and they wanted to run for a state Senate race. And they always ask the same questions. They were questions large and small. How do I find a treasurer? Who should be my campaign manager? And then, you know, what if I feel as though I don't know enough to run? What does it actually mean to bill? How do you learn how to legislate after election day? And I wasn't sure how to answer any of those questions, Chris, because I only represent one tiny corner of one tiny state. But I did learn some things along my journey to the state capitol. I ran, when I was 22 years old, my college roommate became my campaign manager.

And our very first fundraiser was in our college dorm room. We made a lot of mistakes and we got some things right. And I tried to capture all that in a book that shows the good, the bad, the funny, hopefully, and frankly, the ugly of what it actually looks like to run for office, what it takes to legislate and why I desperately hope other young people will take that leap of faith and not just show up at the ballot, but start to show up on the ballot every election day as well. Yeah. So the name of your book is 100,000 First Bosses, and it shows you, it looks like knocking on some doors there in your hometown. Where does the title come from? So this was my first job out of college, and everybody's first job has a lot of stress

associated with it, right? You're eager to please your first boss, to reassure them that they've made the right choice when they went out on a limb and hired you. In my first job, I had 100,000 constituents who lived in my district and I viewed all of them as my bosses. They were 100,000 first bosses. And part of legislating is figuring out how to manage those expectations, how to keep in touch with the folks who voted for you, and as importantly, or more importantly, the folks who didn't vote for you. How to disappoint your friends sometimes, because the campaign trail is all about being popular, but legislating is about much more than that.

It's about doing what you think is right and helping to move the state forward. So it's about learning how to disappoint some of your bosses sometimes and taking responsibility for that, asking for their vote when re-election day comes. That's the reason for the title behind the book. So you're going to college. What are you studying in college? Do you have an interest in political science as a young person? Is there some turning point or prompt that brings you to the moment of going, I'm going to run? Well, I was always sort of interested in politics. You know, my dad, Chris, used to bring me to the New Hampshire primary. We had some family up there and I don't know if you've ever gone to New Hampshire for the primary, but it's like you get to witness democracy on the ground floor. I still think it's the coolest thing in the world.

You're shaking hands with candidates at the dump and you're sitting down with them in living rooms over coffee. You're, you know, sharing a pie with them at the local diner. But instead of those candidates running for, you know, mayor or state senate, one of the down ballot races, like the one I'm in, they're running to be the leader of the free world. It really is humbling and exciting to see. So as a little kid, I just remember, you know, meeting a young state senator named Barack Obama, a young senator named Barack Obama, and just being in awe of the optimism and the hard work that he brought to public service. Anyways, fast forward. And I was studying government in college, going to school in Washington, D.C. Thought that I wanted to work in government in one capacity or another. But I'll be honest, I didn't follow state politics.

I think there are a lot of people out there like that who just they don't know who their state senator is. Maybe they don't even know that they have a state senator. I think people can be forgiven for that. Right. We lead busy lives, all of us. And if you have time to tune into politics, probably going to watch the White House press conference and not what's happening in your local legislature. But here's the thing that I've learned. There's a ton of interesting things. Whether you care about the quality of the roads that you drive on or the quality of the air that you breathe or the water that you drink or the quality of the public schools that your kids go to, all of those decisions are actually made at the local and state level.

So the turning point for me, the aha moment was President Trump's election when I decided, you know what? I didn't agree with what was happening at the national level. I wanted to get involved. And D.C. was going to be rather disappointing for the next few years. The first line of defense, if you were worried about college affordability, environmental protections, gun violence prevention, reproductive health care and freedom, all of those issues, now they were going to be decided at the state level. So for the first time in my life, I found out who my state senator was. All politics are local. Now, let me go back to one thing. You mentioned pie. If I run for Congress, I can get free pie?

Oh, yeah. I have to say, though, the quality of the food that you eat at campaign events, it varies, man. I actually feel like this. I went to my old elementary school last week to talk to students. And I gave a little spiel about local and state government and how their voice was important. And I said, does anybody have any questions? And this one hand in the back shot up. So I, you know, of course, you got to call on that kid first. And he was like, do you ever have to go to events where you eat things that you don't like and i was like yes all the time all the time that's such a great question oh note to self start running for office and have a pie campaign so yeah yeah the the american can be better damn it if we just make better pies

that's turning you know i used to i mean that's how america used to be great when america was America can be better, damn it, if we just make better pies. I mean, that's how America used to be great. When America was great, I mean, I'm just doing a bit here. When America was great, we had apple pie and baseball. And we still have baseball, but it's boring. Anyway, I'm just joking. We lost two people in the baseball crowd there. Oops.

And people on the rhubarb pie are probably like, why did you choose apple? Fuck you. I'm turning this off now. So I've lost that crowd as well. Anyway, so this is an interesting story. You know, I'm seeing here, you overthrew an incumbent who is a Republican. And then, you know, this is,

in my understanding from the wiki here, 26th district had not been represented by another Democrat. So you're not only like young and your first time at this run at this, you're overthrowing a lot of, a lot of establishment. Is that correct? Yeah. So I'll be, I'll be frank because the theme of this book is full disclosure, right? I really thought you were well, not Frank. Okay. I'll be right. I had to do it. Anyways, you know, I, the theme of the book is honesty

and I want to give people a real look at what this process was like. When I found out that my state senator was a member of the opposite political party, I was surprised. When I found out that she and I had fundamentally different views on a whole host of issues, for example, she said that we went too far in regulating guns. I thought we hadn't gone far enough. I lived right around the corner. I live right around the corner from Sandy Hook Elementary School. That tragedy, it's fresh on the minds of the folks that I represent. So I was shocked to find out that the incumbent was somebody who I disagreed with. I was really shocked to find out, Chris, that it was somebody who had been in office for longer than I had been alive. And then the final

straw that broke the camel's back was when I learned that nobody else was running. Sometimes when they're a longtime incumbents, everybody just starts to assume that the seat belongs to them, but that's nonsense, right? In a democracy, the seat belongs to the people who show up on election day. So I decided to throw my hat in the ring, not because I thought we were going to win. The district, as you said, it hadn't been held by a Democrat since the 1970s. But I thought that running was important. Even if we lost, it's just a valuable, even if your listeners disagree with everything else I say today, we all should agree that incumbents should be held accountable for their voting record. Every candidate should have to go out and knock on doors and defend the work that

they've done. When you're speaking on behalf of constituents, you owe it to those constituents to circle back and talk about your voting record and have your feet held to the fire. So that was our goal initially. So how did you beat her initially? What was your strategy? What was the difference that made? Well, the answer to that, I think, is really on the cover of the book. It's nothing all that novel, but a lot of people write off the importance of knocking on doors. And I don't know. I'm no expert.

Maybe they're right. President Biden became the president of the United States in a campaign where door knocking wasn't even really possible. And he earned more votes than any other candidate in American history. So there's an argument that door knocking is a thing of the past, but I disagree with that argument because I found tremendous value in going out. It's the last opportunity, Chris, to meet folks who are apolitical, right? Like I could put a billboard up or I could put an ad on the internet, but you're not really going to reach those folks who they don't care about politics, but they do care about the pothole on their street. They do care about the quality of their kid's kindergarten teacher.

They do care about finding an affordable place for their parents to retire in Connecticut. Right. And when you go out and knock doors, what that provides to a candidate that a billboard doesn't is it teaches you what your community actually cares about. So I knocked on 4000 doors and I asked every voter the same question. I said, what's the most important issue for you? And in doing that, I figured out what actually keeps the folks that I wanted to represent up at night. And sometimes they brought up things I had no idea about, but those were the most valuable conversations because I could read up on those problems, circle back, let them know how I would like to help if I could earn their vote. And it didn't just make me a better candidate. It eventually made me a better state senator, right? I circled back on those houses that had potholes

in the street and I made sure that those potholes were filled. And I just think that there's such value in door knocking and I recommend it to every candidate I speak to. That's why I put that photo on the cover of my book. I love it. All, all politics are local. I mean, AOC, I'm not, I'm not familiar with the two other many people that run campaigns, but I know AOC did a lot of door knocking, you know, there's the famous photo of her shoes wearing out and, uh, you know, and, and I imagine it, you know, it's a good way to get yourself in front of people. I mean, here in Utah, the legislators knock on my door, uh, and they used to want to put a sign way to get yourself in front of people. I mean, here in Utah, the legislators knock on my door, and they usually want to put a sign out, too, on the corner. I had one of those corner lots, so I guess it was popular.

But, no, it's a good way to get to know your constituents, get them to know you as a face, brand name recognition. And I guess they like you so much they had you back in two years again. Well, that is a whole other campaign, right? Running for office as a challenger, your role is then just to sort of present some ideas about how we could do better to kind of paint a vision for our community's future and to poke holes in the voting record of the incumbent and say, listen, I don't agree with this person and I don't think you do either. Running for reelection as an incumbent, totally different, right? You are, I voted on, you know, hundreds

and hundreds of bills and your job is to go out there and defend those votes and talk about why you think that they were the right thing to do. Or if you got it wrong to be humble about that and say, listen, I try to get it right more often than I get it wrong, but we're not perfect. Anyways, it was fun to run for re-election. I have to say it was a campaign that was totally different in its nature as the COVID pandemic. So there were other challenges about how to actually, we couldn't go out and door knock at the same level as we had in the first race. But yeah, I'm just now wrapping up my second term. And you, in 2019, you were named as Forbes 30 under 30 in law and policy. You're, are you

still the youngest state Senator in the country? I think I am. There's not a ton of great data out there that I've seen, but folks keep telling me that. So I, I, I think I believe them. I don't want to be, I hope that other young people run for office. I think we should have young people at every table where decisions are made. I think we should have young people at every table where decisions are made. I think we as a generation bring an important and unique perspective that's often lacking right now from the public policymaking process. So I don't want to be the youngest state senator for long, but I think I am right now. I hope your book inspires young people to get involved in politics. We have a big product review and gaming community with the Chris Voss Show

where we've done product reviews for 12 years along with the podcast. And we used to be really into tech for the first 10 years with the podcast. And so, you know, I see a lot of young people and they're really discouraged. They don't care about politics. They think politics are stupid.

I have to admit, when I was young, I thought it was too. And this is their future, you know? And, you know, I am a moderate Democrat, but I was reading, you know, just today about Mrs. Feinstein. And I'm not knocking her record or what she's done. But, you know, she's 88. And I guess there's some leaks coming out that maybe it's time to go. And maybe her mental state is not good.

And I'm not knocking her. I'm just using the example of, we have a lot of very old people in Congress who, who kind of, in my opinion, I'm not saying Mrs. Feinstein is out of touch. I'm just using this as an example. But, you know, when I see a bunch of very old gentlemen and women up on the thing, deuses at Congress and, and they serve well and they serve power. But, you know, when I see like the interviews with technology, you know, we're talking about how to prevent attacks from Russia and cybersecurity, you know, and different things like that. And, you know, these guys don't even know how to operate their cell phone. You know, when I see that sort of thing, I'm like, we need more young people who understand the future of where things are going, who understand the technology basis for where we have to have. I think we had Will Hurd on the other day, the former congressman Will Hurd. You know, and I said to him, I says, I remember watching all those, everybody just lose their minds when Mark Zuckerberg and Google showed up.

They didn't understand anything of what was going on. It was embarrassing. And, you know, well, there's some things to senior statement and stuff like that. We also need more younger blood. There needs to be more of a balance, I guess, is maybe what I try and suggest of people. And I hope your book inspires young people to get involved, to give a damn about their future, because this is their future. It's exactly how I feel, Chris. Every day, whether it's in your local town hall or whether it's at your state capitol, or as you said, whether it's at the Congress of

the United States, folks are sitting around these tables and they're making decisions about what the next 10, 20, 50 years of American life will look like. And by and large, with a few exceptions, they're doing so without any input from the stakeholders in that future. And by and large, with a few exceptions, they're doing so without any input from the stakeholders in that future. And that should scare all of us who believe in the promise of representative democracy. It's not about replacing one generation with the other. It's about anyone who's touched by public policy should have a say in creating that public policy. That's why we fight so hard to elect more women into office. It's why I believe so strongly that we need more people of color in office. And it's why I'm really dedicated to making sure that more young people step up and do decide that they're going to pursue public service

because they uniquely know what it's like maybe to participate in a school shooter drill. They know how hard it is to try to afford a degree in the 21st century. They know what affirmative consent should look like on a college campus and maybe tragically what it doesn't always look like. They know that climate change isn't just like an academic problem, but poses a real existential threat to their ability to lead happy and healthy lives. There's so many valuable insights that I think young people could bring to the table that right now are just overlooked at every level of government. Yeah. And they really need, like you say, a seat at the table. I mean, when I had Will Hurd on, he's a Republican. We don't see eye to eye on some things, but he wrote a pretty good book on,

you know, it might've been a blue sky, but you know what politics should be. It might have been a little Pollyanna, but you know, it was a good effort. But to say, you know, his thing is everyone should have a seat at the table. Like you met women, you know, I remember years ago looking at the pictures of the Congress and I'm like, holy crap, that's a lot of white men. That's a lot of, that does not look like America. If I go to my shopping store, that looks nothing like my shopping store. And if it was my shopping store, well, I'm probably be being Alabama. That's a joke. That's a deliverance joke. Anyway,

I like to pick on Alabama. Oh shit. I just lost. I don't know. One of the toothless listeners. Anyway, fun is fun. Anything more we want to plug out in your book or tease out on your book? I would just say that, uh, it's been such a pleasure speaking with you and I, I share your hope that somebody out there, whether it's in Connecticut or whether it's in Utah or whether it's in Alabama, decides to pick up this book and decide that they've got some ideas as to how their community could be just a little bit better. My takeaway on legislating is that it's kind of hard and it takes a lot out of you. But anybody could do this. So long as you're willing to listen, you are ready to legislate. Nobody knows everything about every issue. When my colleagues speak about starting a small business or taking out a mortgage or grappling with declining health

of their parents, I've got to do more listening than I do talking. But when we talk about college affordability issues, I was on a college campus not very long ago myself, so I speak up a little bit louder and I could use some company. We need more voices who are in those rooms fighting for that future that we're going to take part in. So thanks for having me. And I hope maybe some of your listeners decide to run for office. And if they do, maybe they'll find some useful tips or at least mistakes that they can avoid in this book. Definitely, man. Get off the video games. Get your head out of that Instagram, you know, some of the time. And read a book and get into politics, man.

I mean, I didn't get into political science until later in my life when I got bored and had nothing else better to do, I guess. I don't know. But I've followed it roughly, but getting into it much deeper, and, of course, we have a lot of journalists and political stuff on the, on the show and some politicians that have come by learning about it and the science of it. It's actually kind of really fun when you get into it and the depth of it and how it works and the powers that be in the push and the pull.

And it's just everything on how the world world kind of works in that thing. And you, you really get into the minutia of it I think is the right word I'm looking for. Absolutely. Absolutely. Yeah. And we all pay attention to DC, but, you know, if you were disappointed like I was that senators Sinema and Manchin took paid family and medical leave and free community college out of president Biden's build back better plan, you should be heartened to know that a lot of States are moving forward with those policies on their own. Oh, are they really? That's good. Here in Connecticut, I helped to write the Free Community College program. It's helped 7,000

students get a degree. We have 12 weeks of paid family and medical leave implemented this past January. So every new parent can take time to bond with their newborn. So while Washington is talking about problems, state governments are actually solving them. And that's pretty exciting. I think that's the beauty of your message because we do get turned off sometimes by the negative stuff in Washington. And it may be the message to young people that you can do so much different at a local level. Get involved and do stuff. It's been wonderful to have you on the show, Will. Thanks for coming by.

Thanks so much for having me, Chris, and have a great day. Thank you. Give us your plugs one last time so people can find you on the interwebs, please. Absolutely. Will Haskell CT on Twitter, Will Haskell for CT on Instagram. Would love to hear from all of you on those platforms. There you go. Thanks so much for tuning in.

Go to youtube.com, 4chesschrisfoss, hit the bell notification button. Go to goodreads.com, 4chesschrisfoss, see everything we're reading and reviewing on my books over there. Go to all of our groups, Facebook, LinkedIn, Twitter, Instagram, all those places. Those crazy kids, like Will, are playing on the interwebs. Thanks for tuning in.

Be good to each other, stay safe, and we'll see you guys next time.