Introduction to Joe

I was born on Sunday, October 18th, 1987 in Lansing, Michigan. My parents were both born in Michigan. My father, James Holberg, was the son of Robert M Holberg who rose to the rank of 2nd Lieutenant in the US Army and served in both World War II and the Korean War. My mother, Lynda Wall, was the daughter of Robert James Grinnell, a seaman on the U.S.S. Toledo during the Korean War. Robert was married for 50 years to Janenne Grinnell who spent 25 years supporting hearing-impaired students in the Lansing School District. Many of my ancestors on both sides came to America in the early to mid-19th Century from myriad places such as Denmark, Scandinavia, England, and Germany. My maternal grandmother's mother was half Native American - hailing from the Iroquois Nation. I proudly consider myself an American Mutt given this amalgamation of origin. No one dimension dominates, but all are cherished.

I grew up in the rural farm town of Eaton Rapids, a small town of just 5,000 people, which was founded in 1837, coincidentally the same year as Chicago. ² I graduated sixth in my class and in order to apply to the University of Michigan, I had to go down the street to borrow $40 from a neighbor to pay the application fee. Finances were always tumultuous and scarce given my father's inconsistent work changing out long fluorescent lightbulbs for large stores like Home Depot and Best Buy. My mother's part-time work as a teacher's aide at the local schools helped out, but the looming prospect of being a first-generation college student - wholly reliant on federal student aid and loans - was beyond daunting. I knew there was no safety net or financial support to be had - save for what I could earn on my own.

By my senior year of college, I ran out of money and was forced to choose between paying for housing or tuition. I opted to pay to stay in school and graduate. But this meant I slept in my car, was homeless, showered at the student rec center, and relied on food stamps to finish my studies. I ultimately graduated during the Great Recession in 2010 with - as I now say - two degrees: an Economics diploma and a hard-earned certificate in the school of hard knocks. Both have been immensely valuable and treasured, although one is hung on a wall and the other is worn on my sleeve, as they say.

At graduation, I felt a deep sense of responsibility. To pay forward the government's investment in my education - to others and to society. So I signed up for Americorps ³ and joined the Executive Director of the Capital Good Fund, a microfinance nonprofit, as the first employee. I helped bring their financial systems into existence ⁴ by building their small business and financial coaching programs, starting a low-income tax preparation site, and creating a non-traditional underwriting system to scale their socially conscious lending program and combat predatory financial firms.

After my year of service in Americorps, I became a middle school math teacher on the West Side of Chicago near Chicago and Pulaski. The Black and brown students at my school challenged me to become the best teacher I could be for them. Society wrote them off, redlined them, and gave up on them, but it was clear to me that their talent and hunger for knowledge was immense and untapped. But before they could listen and learn math, they needed to know I could be trusted and that I believed in them. I built that trust through a balance of fun and accountability: games at the end of class, visual trackers that celebrated their growth in fractions and algebra, and showing up in their community—cheering on the sidelines of sports on Saturday morning and sitting in the pews on Sunday. Whether through small daily check-ins or weekend visits, I did whatever it took to show I cared. It took time, but showing them that I was all-in and that they were worth my time and effort changed everything.

Once we started rowing in the same direction, they put in the hard work as did I to focus on learning as much as possible. They achieved three years of academic growth in one academic year. For context, Chicago Public Schools' (CPS) average growth rate is less than one year of growth each year ⁵ (meaning the average CPS student falls further and further behind each year in our city's broken educational system). Of course their parents and caregivers cared deeply about their success so much so that many were working second and third jobs to make ends meet. This may have meant that many couldn't make it to report card pickup, but they were entirely invested in seeing their children thrive and excel.

Over time, I noticed my students' increasing attention to their cell phones. I realized that I wanted them to be creators of technology, not just consumers. So I raised money from Donors Choose, an online education crowdfunding platform, to buy laptops as our school couldn't afford enough of them. I introduced a simple trade: finish your math and then there's a computer here to learn how to code. At the time, I didn't know how to code myself, but I figured if I could teach myself something the night before at 9pm, I could show and teach them the next day at 9am.

It worked. They absolutely loved it. They loved manipulating code and seeing its immediate impact on the screen in front of them. They loved animating little pictures and characters, building games and puzzles for each other to play with. They loved having a sense of control and ownership over technology. They loved making things. And while I loved seeing their minds humming, I also loved that they focused on and did their math so they could get on the computers to code.

A friend heard I was teaching coding to my students and she passed along an opportunity to apply to a fellowship program Google was starting called the "Computer Science Teaching Fellowship." I thought it was a long shot - my three roommates actually laughed at me when I told them I applied to get a job at Google - but they called the next day and offered me an interview and soon thereafter, a spot on the team. After the school year concluded, I started the fellowship and was a newly minted Noogler (aka "New Googler") - colorful hat with spinny propeller and all.

Our Fellowship cohort of 18 was charged with teaching kids about computer science and coding. We asked our managers what age they wanted us to teach and they told us to "figure it out." We asked if we should teach in person, virtual, or some combination thereof and they said "figure it out." We asked how many people they wanted us to teach and they said….you get the point. We quickly realized the Fellowship was essentially a blank check startup where anything we wanted to try out was on the table and any resources we needed would be procured.

Having that in mind, we developed our "moonshot" which was to teach anyone, anytime, anywhere in the world. We determined - after lots of trial and error - that increasing access to engaging and fun computer science materials gave children a positive experience, in particular girls and students of color, and helped to counter socialized perceptions that they didn't belong in technology or that computer science wasn't related to their lives and the things they cared about.

One of the central design elements of our program was to build content around topics and themes that kids already liked and engaged in. So instead of saying "you should learn computer science so that you can make fun computer games or create digital art later," we flipped the script. Our curricula centered around the topic itself so it was more germain to their lives. We focused on sports, games, art, and music, knowing that they could immediately build a game, create music or art, and more while they happened to be using computer science to do it. We started working with local schools in an after school capacity to refine the program and teach students. We knew it needed to be intuitive to set up, easy to use, and fun to engage with to scale so the online version was as easy for an adult to set up as it was for a student to learn.

During the Fellowship I thought a lot about scaling, distribution, and getting the word out. I conducted a state-wide mailing campaign to send information to every school in Mississippi (they were ranked last in the nation academically at the time), collaborated with partners at state education agencies in places like Arkansas, North Carolina, and Utah, and helped to set up the city-wide effort by NYC Public Schools and then mayor Bill DeBlasio to bring CS First ⁶ to every single after school club in the city. Especially important to me was the ability to set up a training workshop at the Google Chicago office in partnership with CPS where we invited over 200 teachers and educators to learn about CS First and how to implement it in their classrooms or in after school settings.

Within six months, over 10,000 students across CPS had access to and were learning about computer science through the program. It scaled internationally and quickly reached over one million students. The two-year Fellowship concluded, but over the course of the program's lifetime it impacted over five million students globally.

As the Fellowship wound down, I was developing an idea around financial education. By this time, I had spent time in finance, education, and technology and I started to meld them in my mind to solve the glaring problem in the US where we have virtually no financial literacy and financial education as part of our K-12 or college curricula. We teach students to write essays, read Shakespeare, analyze biology, and rudimentary math, but we entirely skip what a credit card is, how to do your taxes, how to make a budget, and buy a house.

The void is so large that once you see it, you can't unsee it. And the results are devastating. Hundreds of millions of Americans walk into adulthood completely unprepared to navigate the modern economy and their financial lives.

I kept realizing that even the most educated individuals that I knew in my professional life (think fancy 4.0s from Harvard, UChicago, etc.) had the same basic personal finance questions as lower-income individuals I encountered working in non-profits and who often didn't complete high school. I knew why someone like myself didn't learn anything about personal finances growing up, but it was jarring to see people from all walks of life with the same questions I had.

Everyone had questions, few had answers. I learned about personal finances out of necessity. Now I was becoming the defacto go-to person for friends and colleagues. I was getting pretty good at helping people with their finances. And the big idea was that I could start a company to help people become more financially empowered, educated, and successful.

It was a big leap leaving Google. People told me I was crazy. They couldn't understand why I would leave the comfort, stability, and, quite honestly, the free food ⁷ to be an entrepreneur and small business owner. The irony is that the outside world thought I was taking a big risk by leaving Google, but I knew that the bigger risk was staying. If I had stayed a good 15, 20, or even 30 years my tombstone might read something like "Google employee #76,308" ⁸ - and that terrified me.

I had squirreled away $30,000 in savings between my time as a math teacher and at Google, and the risk of a startup was "now or never". If I ran out of savings I would quit the company and go get a job somewhere else.

I founded Holberg Financial in the summer of 2015, and went all in on bringing financial education to the masses. I was inspired to help as many people as possible work towards and achieve their financial goals and dreams. People wanted to pay off their student loans, budget better, buy a place of their own, travel more. I knew the need was there, I just had to figure out how to bring an affordable solution to people that worked for them.

At the outset, I called everyone I knew and asked them if they wanted help with their finances. Not surprisingly, virtually everyone said yes. Then I would say "that's great, I'll help you for $20/month," to which most people said no (also not terribly surprising).

After a full year of hustling I was able to sign up about 100 customers. I was at least breaking even. To make the dream work, I didn't pay myself for the first two years so I could invest everything I had into the company. I went so far as to sleep on the floor at a small office I rented in Noble Square from the Polish Roman Catholic Union over on Augusta Boulevard. I had a microwave, but no refrigerator or stove for a long time and sustained myself on cans of beans, bread, and ramen noodles - fortunately food groups that I enjoy! It was this mindset of scrappiness, resourcefulness, and desire to build something that improved people's lives that pushed me forward during the challenging early days.

I knew I was on to something, but those that would benefit the most either could not or didn't want to pay for another service. Financial insecurity becomes more noticeable once we take the time to look for it. It doesn't just go away, it compounds and worsens over time like an open wound that hasn't been properly tended to. It's very challenging to pay for something to solve the problem that you don't have money to pay for. Financial stress and insecurity is a classic catch-22.

So I started to think about how to overcome the challenge. I knew people wanted support, they just needed a way to access it without needing to pay themselves. It dawned on me that all of these folks were employees at companies. Why couldn't the companies themselves pay for a better solution on behalf of their employees? If the company paid for it, then the employee could get access to a novel solution for free. This "business model innovation" unlocked everything - and with the switch to selling to organizations instead of individuals, the company became the first financial wellness benefit offered in the US.

Around this time, I joined Chicago's technology incubator, 1871, in the Merchandise Mart. Being surrounded by hundreds of entrepreneurs, mentors, and investors was a true game-changer. I felt very fortunate to be there. The company started to grow quickly in a dense network of innovators and builders as ideas flew around as fast as the generous offers from the community to lend a helping hand, to share feedback, to make an introduction. I could feel the business foundations getting stronger every day.

With the technology platform I cobbled together - coding late at night, begging software engineering friends for help, and finding part-time help here and there - things were coming together. By early 2017, everyone that used to call me directly for advice was heading to the web platform as their first source of financial education and support instead. Against all odds, I was making something that meant a lot to folks that had questions about finances, could finally get answers.

At this time, most had never heard of financial health or financial wellness. As we created and defined the term itself, we were often doing as much to explain the idea as the product and solution. I knew I needed buyers to trust me as much as the solution itself. Unfortunately, my age was working against me. I'd show up, share how our solution improved employees' lives, then be told I was too young to help people with something as complex as their financial lives. It was disheartening, but I knew what they were saying was "how can we trust you?" It wasn't about my age per se, it was really a question of experience and expertise.

So I decided to write a book on personal finance to help overcome this obstacle. After a lot of keystrokes and editing, I published Rogue Finances on February 17th, 2017 ⁹ and started to take it to meetings. It worked like a charm sliding the book across the table. We picked up six new customers in fairly rapid succession and were off to the races from there.

At that point, a mentor at 1871 said to me "you should raise VC!" To which I said, "what's VC?" He looked at me like he had seen a ghost. "It's venture capital." He proceeded to patiently explain it to me. The next day I was pitching VCs on my idea and eight months later I'd managed to raise one million dollars. I pitched 190 VCs and angel investors and 180 of them said no. It was a soul-crushing yet enliving experience. I knew that I only needed a few people to believe in and invest in the company, not everyone. I tell this story because that is where Chicago is today: we need everyone to believe and invest in our collective future even if there are naysayers telling us it's not worth it or not possible.

We ended up with incredible investors that championed and supported our vision. We hired a few software engineers, a product designer, and a sales person and got to work. Over the next few years we grew at a healthy rate and right when we were getting ready to raise another round of venture capital, COVID-19 hit. All plans went out the window and we retreated to survival mode for the next two years. It was an incredibly trying time leading through chaos and uncertainty, but it sharpened my focus on the things that mattered the most: helping people build their financial health and navigate the financial chaos unfolding around them. Unlike many companies that went under, we emerged stronger and more resilient as financial stress was a marquee issue for employees during the pandemic - arguably second only to the immediate health concerns we all faced. Companies stepped up for their employees and we grew over 400% as we served over 25,000 employees in Chicago and nationwide.

We even changed the old-school sounding "Holberg Financial" company name to "Spring" and built out our technology platform to a one-stop shop where you could track all of your accounts, set financial goals, build a budget, access financial education content, and schedule 30-minute financial coaching meetings with our team of licensed coaches.

We had become the top-rated financial wellness benefit in the US for three years running when one day I was working on my computer and the little blue message light went off on LinkedIn. It was a company interested in learning more about Spring. I was hesitant, as we got a lot of inbound inquiries from companies wanting to "explore partnerships" when in actuality they just wanted a free look under the hood to inform their own efforts. The company that reached out, Mariner Wealth Advisors, seemed genuine though and after a few calls, it was clear how aligned we both were in terms of the vision and mission to bring financial education and support to as many people as possible.

They indicated their interest in acquiring the company and asked me how much I would sell the company for. I didn't hesitate to say my number - every small business owner and entrepreneur has one. They didn't bat an eye and agreed to the price. Like any good founder would do, once they said yes, I asked for a higher price. And like any good buyer, they said no. At least I tried!

The next few months involved lots of meetings, providing them with information about the business, and discussing the shared possibilities of working together. Ultimately the company was acquired in early 2023 and my and my family's lives were changed forever…

Our family started when both my wife and I came to Chicago long before we met. Jessica and I were like many that come to Chicago looking for education, opportunities, and a future. We both rented apartments in various neighborhoods throughout the city years before finding each other and being able to save enough for a small condo. She started in the South Loop while a student at Columbia College Chicago and my first place was in Ukrainian Village on Western and Huron. Before we met, we bounced around individually from apartments with roommates trying to find various mixes of places that worked with our budget, commutes to work, and lifestyle. Some places broke the budget while others were in the Goldilocks zone: not too expensive, but not too threadbare! By the time we started dating, she was in Wicker Park renting and I was nomadic: sleeping on a friend's couch in Rogers Park, with no income, as I poured everything I had into my business. As things got more serious between us, I moved into the small two bedroom one bath with her and her roommate and split the rent three ways which was a needed budget boon to each of us.

At a street fair, I told Jess that I was going to start saving for a place to buy and even if we didn't end up together in the long run, we could each set savings goals and help each other work towards them. Sure, I was hinting at wanting to be with her forever, but at the same time, she worked incredibly hard and I cared about her future no matter the outcome. As the summer months of 2017 turned to winter months of 2018 we had each cobbled together enough to think about looking for our first condo. Our lives spun together more tightly everyday as the fabric and patterns of reality shaped our habits and desire to be together as much as possible. We went condo hunting for months often faced disappointment - having been outbid by a slightly higher offer beyond our reach or similar offers where others had more savings, more cash, or higher paying jobs to bolster their efforts. We walked away deflated after envisioning quiet evenings on a back deck and short walks to take the train to work. Building mental movie reels of our days just to see them go up in smoke. Months went by, hundreds of listings and viewings, too many offers to recall until finally, we found a little slice of earth to call our own. Technically we shared that earth as part of a condo building, but in May of 2018 we closed on a little 900 square foot, 2 bedroom 1 bath condo. We were elated and moved in and quickly switched gears from getting engaged under a Kandinsky in the Art Institute of Chicago to wedding planning in Ravenswood and, before we knew it, we were married in January of 2019. Little did we know, we had just one year of freedom. Our world, like millions of others, went quickly from spending time with friends, enjoying the vastness of the city, and ideas of traveling before kids to lockdown.

On Friday, March 13th, 2020 the world shut down and we holed up like everyone else. We freaked out, tried to understand what was happening, educated ourselves on how to stay safe while also staying sane. Gloves were worn, then groceries disinfected, then masks donned. Circles in the park demarcated distance to keep us away from others. We flipped from planning travel to being pregnant and having our first born in 2021. We were living paycheck to paycheck at that point, both working, trying to stay safe, raising our son, and trying to figure out life together.

Joining Mariner in 2023 as COVID "ended" was a fundamental shift in our life that opened up new possibilities that we had never dreamed of or been able to contemplate. At the same time, the newfound freedom strengthened our existing commitment to serving others. We knew we needed to accelerate our commitment to advancing others as Jess had done for over a decade as a teacher and then principal at an elementary school in the Austin neighborhood on Chicago's west side. I too wanted to extend the arc of my experience blending nonprofit, education, technology, and startups. We resolved to fund several nonprofit efforts including one called Model United Nations that engaged Black and brown students on the south and west sides of Chicago in a debate club that culminated with them traveling to New York City alongside students from around the world to debate a range of issues on the United Nations floor. These Chicago students represented our great city with confidence and pride, debating some of the most well-resourced Model UN clubs from around the country and the world. In one recent year, their "delegation" received 15 awards which was the second highest total out of over 50 schools including several international groups from other countries. As Dilla coined, "everything dope about America comes from Chicago." ¹⁰ This Model UN club is just one of infinite examples!

Our next effort was to further our investment in students in Chicago by starting a scholarship fund for first-generation Chicago students to help them pay for college. We are both products of the country's public education system and deeply value and understand the power of this education. We have witnessed and worked in schools and communities where students' true potential is too often limited due to the zip code they are born in and we wanted to do our part to propel the next generation of college-bound students and support their aspirations and ambitions.

Admittedly, it's a small drop in the bucket, but it represents the kind of cumulative investment our society owes the next generation. Young people deserve the opportunity to pursue academics and fulfilling career pathways. They should be able to complete a college degree, trade school, or vocational training with manageable student loans, rather than a crippling cycle of debt that depresses their ability to build a successful life.

As we invested back into Chicago and our young people, we continued to build our own family and careers. I continued to see more and more people of all types struggling to make ends meet. After ten years of helping thousands of people navigate and reduce financial stress and supporting them in reaching their financial goals, I'm actually surprised it didn't dawn on me sooner - but when it did, in 2024 and early 2025, it hit me like a ton of bricks.

What I was observing in our city was that the promise and the hope of the American Dream was quickly devolving into a sick and very expensive version of an American Nightmare. The cost of virtually everything around us exploded to heights rarely seen before. Even swinging by the gas station to fill up or opening your utility bill could send your entire month's plan and budget to the bottom of the financial ravine. Rents were increasing faster than people could afford and the twin problem of watching a home's or starter condo's price slip out of reach - paired with unending property tax increases - meant that even the roof over many peoples' heads felt less secure than the joists that supported them.

Add up day care costs, student loans, and astronomical grocery bills, and the reality becomes clear: a city once known for affordability is pushing residents out to suburbs like Evanston, Wilmette, and Oak Park and even further afield to other states.

When the cost of living forces working families to rethink their future in the city they love, something is fundamentally broken. I knew the answers wouldn't come from City Hall, so I went straight to the source: hardworking people all across the city. It became instantaneously clear through hundreds of conversations that what people wanted was not only change, but a real problem-solver focused on making their lives better rather than enriching themselves and their political career.

I spoke with tens, then hundreds, and now thousands of people from every corner of this city and the message is clear: people in Chicago don't want more of the same. People don't want another career politician. They don't want hollow words without any action. They don't want to be priced out of the homes, the neighborhoods, and the city they love. They don't want failing schools, a broken debt-filled budget, and they don't want to feel scared of stepping foot outside onto their porch, walking to their local grocery store, or going downtown to Michigan Avenue. People want real solutions to real problems and they want the city to fulfil its end of the bargain. People pay taxes and fees and, in return, the city has to deliver on its promise to build a city that works. An affordable, safe, thriving city for all.

We're a city of optimists. Our whole city burned down in 1871 and we shrugged it off and built a bigger, better city like it was no big thing. ¹¹ We took that destruction and created anew. We innovate. We build. We work hard. We solve problems. We get stuff done and we do it by working together and helping each other out. While our city and our people have risen to the occasion, our government and our administrations have not. Our government has let us down. They have prioritized rewarding their friends and special interests instead of putting Chicagoans first. There's too much talk and too little action.

I got tired of sitting on the sidelines watching the political class put themselves first and I got inspired to challenge the status quo - to advocate for hardworking people whose voices too often fade into the black hole of bureaucracy. To roll up my sleeves and do the hard work like I have my whole life. To put the people of Chicago back in the driver's seat and to focus on making your life better and more affordable.

I quit my job to run to be your next mayor. I'm not a politician and that's exactly what we need right now. I've been an underdog my whole life. People and society bet against me just like they are betting against you right now. Just like they are betting against Chicago right now. To that, I say bring it on. If there's one thing worth betting on, it's Chicago. It's our people. It's our future. I'll take that bet all day, any day.

I hope the following vision for Chicago has the magic to stir your blood. I hope that you believe in yourself, this city, and our shared future enough to believe in me as a candidate and as someone whose sole goal is to be a public servant. I hope you think of me as a small stepping stone to bring about a better reality and future for you, your family, and our city. This isn't about me running for mayor. This is about all of us working together to build a better Chicago today, tomorrow, and for the future generations that will take up the mantle after we've put in an honest day's labor.

Together, we will make no little plans.

Let's go Chicago!