This is the definitive story of the startup I spent 2+ years of my life building.
I hope that the following chapters, which chronicle twelve of the most momentous turning points in the life of the company, serve as an unfiltered look into the process of starting your own business and “failing” (aka quitting!).
I’ve tried not to spare any details or otherwise add unnecessary color to decisions we made that weren’t founded in sound logic — when I used to spend hours a day scouring Twitter and YouTube for proverbial startup wisdom, I always wished founders weren’t so hand-wavy about questions like “What did you actually do every day?”
Since it’s a near certainty you haven’t been introduced… meet Heyday. Heyday is (was) pretty neat! It helps (helped) Gen Z plan ahead and manage their money.
Unfortunately, Heyday died. My co-founder and I quit working on it.
Let’s start from the beginning!
Disclaimer: I’m close to two years behind on getting this out there 👀… but I’ve written bits and pieces since the company’s inception.
Chapter I — The pitch competition
Visor (our earliest name) started in the most unceremonious way possible in March of 2019.
This wasn’t the storybook startup origin story in which the founders encountered the tragedy of the problem they aimed to solve through a sudden real-world experience — Visor started because two of my close college friends and I signed up for a pitch competition and had to invent an idea to pitch.
This particular pitch competition was organized by First National Bank of Omaha (FNBO) out of Nebraska. The prompt was simple: “How can FNBO help young people have better access to financial advice and guidance?”
My friends and I conceived a naive solution — we would connect young people with personal bankers from hometown bank branches digitally (wow!), fostering relationships centered around financial advice and guidance that could help create long-term customers for FNBO.
We produced a pitch video and suddenly became semi-finalists, receiving a humble prize of $500.
Riding high on our egos, the real work had begun — we had to prepare a 10-minute presentation for a large in-person audience to compete against the other five semi-finalists for a grand prize of $15,000. We were given a “coach” from First National and started talking to FNBO executives about the looming death of bank branches, among other things.
Somehow, somewhere through that process of crafting the narrative of our 10-minute pitch, we started feeling oddly energized about the solution we’d scrapped together.
This was something that banks actually wanted, right? This could seriously be a useful tool for young people, right?
Even if this pitch competition didn’t pan out, we could really do this!
In the well-known-but-often-disregarded lifecycle of a startup, we were unknowingly reaching the peak of the fatal “TechCrunch of Initiation.”
In the interest of getting to the more exciting stuff, the gist of Chapter I is that we ultimately lost the pitch competition finals in April of 2019 and were pretty bummed about it.
Seriously… we felt we were really on to something.
My soon-to-be co-founder, Jacob Gideon, and I chose to march forward . Perhaps some part of our motivation was actually a desire for revenge against the evil judges who didn’t pick us to win the pitch competition; an urge to prove the naysayers wrong.
More importantly, however, we decided to continue our investigation into the problem space out of a genuine, unbridled, yet unfounded optimism. More on this subject later.
Chapter II — This is a startup?
The first thing Jacob and I did post-pitch in May of 2019 was fill out a business model canvas and a one-page brief. *shudder*
The challenge we faced in attempting to partner with a massive banking institution as two Computer Science college students was immense, and we didn’t know what else to do besides follow some arbitrary guidelines for how companies should form.
We talked to personal bankers, execs of banks, and just about anyone in banking we could get a meeting with. The end of these meetings was always the same.
Banking Person: So, what can I do to help you?
Jacob and I: We’d love to keep in touch as we continue figuring things out!
We never knew what to ask for or how to make progress towards our goal of building the product we had initially pitched. Visor was a pipe dream; we aimlessly talked to big names in regional banking with the hope that somehow they would tell us what to do and how to do it.
Ultimately, what became clear was that two college kids were not going to integrate with the tech stack of a regional bank and deliver digital chat-based communication channels between personal bankers and young people — at least not us, without any tangible experience to hang our hats on. Banks, like any large institution, need proof in the pudding. Our only choice was to prove that our idea would generate significant traction.
… We needed to generate traction for banks to partner with us… But we needed banks to partner with us to generate traction…
Without a clear solution to this dilemma, we hunted for answers wherever we could find them. We idolized Y Combinator and consumed endless startup-hustle-growth-mindset content instead of actually working on our startup.
It was June of 2019, about 4 months since the inception of the idea, and we had become convinced that as first-time founders (nonetheless college students), we were destined to fail unless we made a big change.
Thus, our first pivot.
Chapter III — The advising app
I would be remiss not to mention that Jacob and I were not working on Visor full-time in the summer of 2019.
In fact, we weren’t even in the same city: Jacob was interning at Microsoft in Redmond, WA, and I was interning at Hudl in Lincoln, NE. Not only did this present logistical challenges, but it also meant that we didn’t spend a significant amount of time working on our startup (if it could even be called a “startup” at this point).
Anyways… the first pivot…
Could we deliver financial guidance by partnering with banks? Probably not. Could we deliver financial guidance directly to individuals who couldn’t afford a “professional” financial advisor? Maybe… If we could, we would have the traction we needed to partner with banks!
Our belief was that we were much more likely to succeed by taking market risks rather than execution risks. We were unproven, and frankly unlikely to be trusted to execute on lofty technical and security challenges. But, proving ourselves by taking a bet on an untapped market that nobody else believed existed was something we could do.
Around this time, by pure happenstance, I was chatting with a fellow intern at Hudl about what Jacob and I were noodling on that summer and it turned out that he had hundreds of hours of nonprofit personal financial advising experience (!!!). Excited by our vision, he wanted to help and even had a close friend to join forces too.
I recall Jacob and I’s initial hesitation to bring on more members of the team being… equity concerns.
We ended up accepting their help later in the summer, and with two new teammates on board and a renewed sense of urgency to execute our B2C vision, we decided to double down on our startup wisdom consumption and sign up for YC Startup School to help guide us through our uncertainties.
Through Startup School, we participated in weekly calls with other founders. These calls were surprisingly useful in pushing us to make progress in the most important aspects of our business. What problem were we actually solving? Does anyone care?
The net result of these conversations was a renewed sense of urgency to get something in our customer’s hands. If we could deliver a financial advising solution that young people cared about, we’d have real usage data to show banks.
Building something as a method of gathering important feedback from potential users, even in your earliest problem discovery, is not inherently bad. In fact, it’s exactly what you should be doing. The problem is that we didn’t just build a tiny experiment for the explicit purpose of gathering feedback…
Our “MVP” was a cross-platform mobile messaging application. The only thing it did was facilitate messaging between two people (the user and their financial coach) while presenting a few action items, but the complexities of mobile development for us then-inexperienced CS students made the development of our MVP take about three months.
We could have built nothing and just started with simple SMS and shared a Google Sheet with action items for each user. We could have launched a significantly less-scalable experiment but gathered the same feedback in a fraction of the time.
Instead, we burned three months building and launching our app, only to realize what we could’ve learned in three days: nobody cared.
Nothing stuck. The answer to “will young people engage with a free financial advisor on a regular basis?” was, apparently, no.
(I don’t necessarily believe that the answer is actually, unequivocally, “no,” but we had little patience after three months to actually iterate and figure out the nuances of the answer.)
And thus, things were starting to get heated among the Visor team. We did notice a stigma against receiving financial advice. We noticed most young people didn’t even know what to ask when handed a well-educated financial resource, free of charge. We realized the economics of a trained financial advisor giving 1:1 guidance at a very low price would (probably?) never work.
We didn’t know where to go from there. School started up again — Jacob and I’s Junior year, and we were lost.
Chapter IV—An opportunity arises
We took a brief hiatus from Visor to clear our heads and get situated in a new school year. I believe Visor could have very well died at that time if not for a newfound extrinsic motivation that shook everything up once more…
Jacob and I’s college program runs “Design Studio,” which organizes upperclassmen into small teams to work with companies on contracted ($50k) year-long technical projects. Jacob and I were assigned to different teams to work with some regional Nebraska companies that year, but an exciting opportunity was announced Fall of 2019 at an all-school meeting that made our heads spin.
The following year (2020), Design Studio (DS) would be accepting its first ever student-led startup team. One founding team would be selected to be part of Design Studio in 2020, with the contingency that they take the prior summer off to work full-time on their company.
Applications were immediately open to pitch.
I mentioned the fact that this motivation was entirely extrinsic. There are many false hopes and promises in extrinsic motivation when it comes to building a startup. If you can’t find it in yourself to get up every day to tackle problems out of a desire to improve the lives of your customers, you’re probably in trouble.
Without said understanding, Jacob and I were ecstatic! If accepted to join the 2020 DS cohort of companies as our own student-led startup team, we would be able to recruit other student engineers, designers, and marketers to help us build the company. We’d be given 1:1 coaching, deployment resources, and our own dedicated workspace.
Not to mention, we’d be the talk of the school! We’d forever be the first student-led Design Studio startup team.
Jacob and I went back to the drawing board. We had to develop a compelling narrative around our business within one month to have a shot at being accepted.
In the process of crafting our pitch, we decided to focus solely on college students. We wanted something more niche that would make it easier to identify core problems and eventually develop early traction to learn from, and some early conversations with the Student Money Management Center folks at UNL gave us a small “in” in that market.
“New” idea in hand, we talked to the director of our program and the director of Design Studio about our concept a few weeks ahead of the pitch.
They thought it could never work.
“Students don’t care about finances.”
“Students don’t have financial problems that are that important.”
“You can’t deliver 1:1 financial advice at scale.”
“You can’t change student behavior…”
In some ways, they were right. Of course, we didn’t buy their opinions, but they spoke with a level head only afforded to someone on the outside looking in. We were buried too deep in our own thoughts and strategies to discern truth from opinion.
Per this skepticism from the individuals who would be judging us (note: not due to anything we learned from our customers), we decided to pivot slightly: we planned to build a platform centered around delivering financial advice and guidance to students from other students by partnering with student financial centers on college campuses.
This pivot solved our “do the unit economics work” concern, but it also made things even more complicated. The underlying problem remained: Did students care about receiving financial advice and guidance of any kind?
Instead of addressing this underlying problem immediately, we spent most of our time before the pitch creating some cool graphics that fit a new name we had just come up with: “Findo”
(Find-oh? Fin-doh? Fin-doo? Fine-doo? You decide.)
We also spent some time applying to YC. Why not!
(What problem were we actually trying to solve?)
In the interest of your time, I present the conclusion of this stage of our story:
We were the only student-led team to apply for the program (no other students wanted to commit to foregoing a summer internship to participate).
We were reluctantly accepted under the assumption that we would spend the following eight months before the 2020 Design Studio year kicked off to iron out the problem space and iterate toward the business the world needed to exist.
Chapter V — The chatbot
Having accomplished our extrinsic goal, things got real. We still needed to answer the questions we had been unable to crack.
Despite the many, many mistakes we had made up to this point, we were smart enough to lean further onto our latest source of investigation and validation: the university student financial wellness centers we hoped would eventually use our product to deliver guidance to students.
Those programs struggled to get students on campus to engage/seek help in the context of their finances, just like us. Students with some serious cash-flow issues asked for help, but most didn’t bother.
We jumped on the opportunity to better understand what these money management centers had tried thus far to reach students.
After failing to re-establish contact for a few weeks, we finally had the opportunity to sit down with some of the big names at our college’s financial wellness center. We learned about the existing solutions they used, the tight budgets they worked with, the antiquated approaches to improving financial health that they relied on (i.e. financial literacy tests and paper/pencil budget sheets), and the general challenges of reaching even the most financially stressed of students.
For the first time, we found real problems that we could articulate. The challenge then was conceiving a solution that A) satisfied the operational goals of the college financial wellness center, B) fit within their time, resource, staffing, and budgetary constraints, and C) actually engaged college students and compelled them to seek assistance.
With these problems and challenges in mind, our first instinct was to build something.
A potential solution.
An MVP.
This time, unlike our earlier attempts, we were a little more intentional about how much time we spent building it.
Findo, the SMS-based financial guidance system, was born. We posted our phone number on as many college group chats as we could wiggle ourselves into, and encouraged students to text it with anonymous financial questions. These questions would be screened by a “chatbot,” but under the hood, it would actually be Jacob and I answering the questions.
We were pretty proud of it! It fit the YC ethos of “building things that don’t scale” quite nicely.
The bot generated some surprisingly interesting early conversations. College students were willing to trust a random chatbot (stranger?) to provide sensitive financial advice.
This was the first time we felt we had done something right. We took the opportunity to attack the problem even more: We asked folks who had texted us if they’d be willing to sit down with us for an interview, and a few students agreed. Ultimately, we discovered a body of students that literally lived loan-check to loan-check because they were too busy to get jobs (they were full-time students) and their parents couldn’t pay for everything (in some cases, they didn’t pay for anything).
I would be remiss not to mention that around this time, we secured some great mentors. We had casual weekly meetings with a local VC, Ben Williamson (a total blessing), and monthly meetings with other members of the Lincoln startup community. For the first time we not only had great guidance but also some accountability.
Having successfully cornered our market into a niche group of students who struggled to ” cornered our market into a niche group of students who struggled to make it through the school year, we started re-evaluating how to validate assumptions. We set up an “assumptions matrix” — a basic view of our assumptions measured by business impact and ease of investigation. Soon thereafter, our #1 objective became investigation of the “shark bite” problem that this group of struggling students faced.
If we could build something valuable for students living life in debt, we might have something that college financial wellness centers would pay for.
Chapter VI — Lets lend college students money
After many more student interviews and some competitive and market analysis to understand how cash-strapped students get by in the status quo, we took our next stab at a simple-to-build, feedback-gathering-focused solution.
The idea was a bit crazy. We were going to build a simple web-based MVP to loan small amounts of money to college students on a weekly basis at 0% interest (because this was about learning, not making money).
The rationale for this first solution concept was simple. If you’re having trouble getting by financially, you either need more money coming in or less money going out. It sounded hard to do the latter (it would require changing someone’s spending behavior), so we decided to start with the former.
In a sudden twist of good fortune, we managed to convince our university’s student financial center to send the link to the web app to some students who desperately needed financial help! This “partnership” with our Student Money Management Center to offer our MVP cash loan service actually worked. We had a dozen students on the platform getting weekly Venmo’s of $50 from us within a couple of weeks…
… right as the COVID-19 pandemic sent us home from school in March of 2020.
Many students ended up moving back home to their parents’ homes at the time, but some of them stuck with us. Despite the setback, we still ended up lending about $1,000 of our own cash to students over the course of the next month.
It’s impossible to say whether this was due to the small sample size, the pandemic, underlying problems with the way the solution was built, or something else, but about a month in we started having trouble acquiring more “customers” — even after sending tens of thousands of cold emails to university students by hijacking emails from our student directory 😅
We tried to get more students interested, but something about 0% interest didn’t sit with them. They were skeptical. They chose to borrow money from their parents instead. We literally couldn’t hand students free money! Why not?
We stepped back. We interviewed. We listened.
We discovered that students hated borrowing money. They already borrowed tens of thousands of dollars every school year in the form of student loans. They already borrowed from their parents. They’d rather face the wrath of Mom and Dad than go through some random, zero-interest, “sketchy” lender like Findo.
Basically, our lending approach to increase cash inflow wasn’t the solution students wanted.
Chapter VII— Starting over with lessons learned
By this time, May of 2020, we had reached the pivotal summer prior to Design Studio.
We were working full-time on Findo and needed to have some strong convictions about the business we wanted to build going into Design Studio so as to best utilize the influx of engineering resources (peer CS students) we’d soon receive on our team the following school year.
In the face of setbacks, in May of 2020, Jacob and I did the only thing we had learned actually worked in starting a startup: we talked to potential customers.
We interviewed about 150 students, desperately searching for our next rabbit hole to explore. After learning about interesting problems related to credit cards, investing, and parent financial relationships, we started recognizing a common thread in the way students talked about money:
Nobody knew how to plan ahead.
About half the students we talked to regularly ran out of money during the school year (this we already knew). Most of these students could ask their parents for help (which we already knew), but that was not a pleasant experience.
These students tried to plan their summers around making enough money to last through the school year — they threw together Excel spreadsheets to track their future cash flow and tried to get a sense of how much money they’d be able to spend at the bars every Friday the following spring based on the money they were earning the prior summer.
Students not only sucked at basic financial planning, but they were actually trying (this was the new information).
With new problems in mind, we sketched and prototypes dozens of wildly different solutions. Crunched for time to validate our business before the school year and inspired not to repeat mistakes that had doomed us previously, we held two critical goals in mind:
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Remain laser-focused on the niche problem of financial planning going into the next semester of school.
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Build the minimally viable solution to that problem as quickly as possible (optimize for fast feedback).
We prototyped.
We interviewed.
We started over.
We prototyped. We interviewed. We moved forward.
We prototyped some more. We interviewed…
Ultimately, we interviewed about 50 college students from a wide variety of backgrounds with a handful of prototypes for about a month. The solutions we invented sucked at first, but they slowly got better.
About a month later, in June, we were starting to feel a bit demoralized. We had burned an entire month iterating on some glorified wireframes without much of a real product or business to show for it.
I remember one fateful week in mid-June in which I was bogged down in quarantine after testing positive for COVID-19. Bored, I slapped together a web app based on the prototypes Jacob and I had recently validated.
Here’s the link to that first version :)
We sent the web app to some of the people we’d interviewed with prototypes and conducted a few “onboarding” calls with some students we’d never talked to.
As it turned out, our fastest learning ever occurred when we actually built something and put it in people’s hands as opposed to sitting around wondering what to build.
Some students used our silly little web app every day, which was amazing. For the first time, we felt like we had made something people were actually inspired by.
We continued to iterate (and probably spent a little too much time trying to make it look pretty). Truthfully, the web app was pretty bad. It was essentially “move these sliders and a graph of your net worth changes.” It was pretty high-friction: you had to manually log transactions (which people hated) to get tangible value from the product and, of course, it was a web app (people hated opening up their browser to use it).
It wasn’t perfect; as we got closer to the fall semester, usage slowly dropped off.
The web app had served its purpose, though. For the first time, Jacob and I felt like we were actually building a startup!
Chapter VIII — Introducing Heyday
In what felt like the blink of an eye, it was the fall semester of 2020. Jacob and I’s senior year of college.
The whole global pandemic thing wasn’t helpful, but we had to onboard our Design Studio team within a few weeks of the semester getting started. We spent a bunch of time getting ready to bring a team on and started laying the foundations for a mobile app that would have feature parity at the start with the web app.
The decision to build a mobile app sounded great at the time. The web app had seen some moderate usage and was clearly on the right track, but it was too high-friction in ways a mobile app inherently wouldn’t be.
With a mobile app, we thought we could implement automatic transaction monitoring with Plaid (we could’ve done that in a web app too…), send out timely push notifications to keep people coming back, and generally establish ourselves as a competitor to the bad status quo budgeting and banking apps college students used. We’d have a full team of engineers to offset the additional burden of building a cross-platform mobile solution, and it gave us a great initiative to tell others about as we returned to campus.
Jacob and I would later reflect on the decision to go mobile as a terribly costly error. More on that later.
Oh, at this time we also rebranded again. A very positive use of precious time.
Findo was now Heyday.
By the end of August, we were officially loaded up and ready to go. We had brought on three engineers and a business/data science student to bring our vision to life, we were freshly rebranded, and the whole team was extremely optimistic about what was ahead of us.
The early days as a team were an absolute grind at the start for Jacob and I. We learned more about being managers, engineers, designers, marketers, and leaders in that first month than ever before. Leading a startup team is hard! You need to devote 100% of your attention to your business and 100% of your attention to your team and 100% of your attention to your advisors and 100% of your attention to your long-term goals 100% of the time…
I quickly learned about the power of delegation. If somebody doesn’t know what they should be doing and feel empowered to do it autonomously at any time, your own schedule gets derailed trying to get them up to speed and everything grinds to a complete stop.
We were a bit ambitious with our target MVP release date of October 1st. The goal was simple: Build a cross-platform mobile app with bank account linkage via Plaid, synced transactions, future cash flow projection, and total feature parity with the existing web app. v1.0 was supposed to look like this:
In retrospect, we didn’t anticipate how slow we’d move at the start just figuring out how to operate a team.
After about a month we did have a first version of the mobile app, but it absolutely sucked. Completely unusable. We had to scrap all plans we had from that point and work for another month just to make our MVP usable.
We discovered after that second month that the MVP was usable but not actually minimally viable.
All you could do is see transactions from your bank accounts and see how much money you’ll have over the next two months through a rudimentary cash flow calculation with your jobs, bills, and rent. It was essentially useless.
Somewhere in the process of building a fancy mobile app experience, we lost touch of the problem we were actually trying to solve.
We tried desperately to talk to students, but they were stubborn and didn’t want to talk. We tried paying them, but their feedback got worse.
So, we just kept building; another month went by just making the existing product viable. We made the projection useful (beyond just two months), gave users more historical data, made it so you can actual edit information you provided in onboarding and provide new information at any time (that didn’t make it in v1)…
There is so much more that could be said about this 4-ish-month period, like learning how to manage advisor feedback, building a system to maximize learning rather than scalability, etc. All these tangents aside, I have never learned so much in such a short time!
Chapter IX — A Winter Break Shakeup
Before we knew it, we were approaching winter break. The app was finally usable, looked decently good (not that our customers probably cared much), and we were onboarding users as fast as we could.
The metrics didn’t lie: Nobody was sticking.
We knew our MVP had failed. We knew we weren’t seeing the proverbial “product market fit” because we had to do absolutely everything in our power just to get anyone to use the product for any length of time.
We kept telling our stakeholders we were doing everything we could to get people on. They kept telling us we needed to find a niche to target first. They told us we weren’t even solving a problem. We were in denial.
We had spent a long time validating this before we built it. What went wrong? Our stakeholders were right, but why?
In the midst of needing to answer these critical questions, we got distracted once more.
Right as we entered winter break, we were given a transformative opportunity to join a local accelerator: $100k for 20% of our company.
It was more of an incubator-style organization, where we would plausibly be encouraged to start something entirely new coming out of it.
Still in denial, still believing we had something going, still wanting to put on a face that everything was going swimmingly, still wanting to prove everyone wrong, still holding on to hope that we could do this ourselves without giving up such a massive portion of our company to throw a white flag and move on, we said no.
I (can only speak for myself) genuinely believed we could figure things out.
When we told stakeholders we said no, it was clear that they didn’t understand our decision.
Chapter X— Stepping back to step forward
We entered winter break and the team pretty much stopped working with us, which was another sign that the app wasn’t working (why didn’t they want to work with us for fun?).
It was just Jacob and I. We decided after passing up this accelerator that we would run our own “mini accelerator” at the beginning of winter break. We would take a step back, evaluate different ideas in the same space as our product, interview tons of people, and come out with an idea for a niche we could focus on and build some legitimate traction.
We spent a few weeks beating our heads against the wall. We interviewed parents, students, recent grads, high schoolers, and everyone in between. We had a list of ideas and problems in which we documented the feedback we received in addition to a running assessment of how viable the niche could be in terms of finding traction or a sustainable business model quickly, since the pressure of time was getting to us.
Graduation was approaching. Our runway was running out.
Actually, it felt like we were already off the runway; we were still on the ground, cruising into a thick forest with no hope for takeoff. We saw close friends getting great jobs and big signing bonuses and we were about the graduate with no income and a useless mobile app we had poured our time and energy into building for a year and a half.
We looked like the losers here.
We had been told by everyone around us that we needed traction by mid-March-ish to raise enough capital with enough time to build something out of this as we graduated school in May. That was our timeline. We only had a couple of months to do what we couldn’t do in nearly a couple of years.
So, we time-boxed ourselves to two weeks on our “mini-accelerator” step-back. That would give us a decent chunk of time to build an MVP and start getting traction headed into the spring.
To state the obvious: Yes, we could’ve just kept working on this without capital after school. My cofounder wanted to do that, and I did not. Selfishly, I was ready to move on if we couldn’t make it work in two years with such great resources, and I had hopes to return to home to Kansas City after graduation with my soon-to-be-fiancé unless the business happened to take off and demand living elsewhere.
This brings me to an important lesson: every founding team needs a common understanding of the goal. Where do you want your business, your life, to be in 2, 5, or even 10 years?
If you can’t envision where you want things to go and agree on that vision, you will fail. It’s simple.
My co-founder and I had brushed off those conversations until the final few weeks of our business’s life. I’m not even sure it was intentional; we just assumed everything would work out if we did all the things people said we should do along the way.
Needless to say, we didn’t come out of those couple weeks with any solid ideas for niches to target or problems to solve. We waded around for a couple of weeks longer, sometimes barely working in a given day, trying not to acknowledge the reality that was staring us in the face: We had completely lost motivation.
Our minds wanted to be occupied by other things. We weren’t even learning anything anymore. We had little conviction about our business or our solution, so much so that we avoided talking with our closest stakeholders for a brief time.
Chapter XI— The end
One random day over that winter break we hopped on a Zoom call. Somehow we started alluding to our lack of motivation, and then actually said what we were both thinking: we wanted to quit.
What everyone says is true. Startups die when the founders give up! We could’ve kept working at this for years on end as long as we could support ourselves financially. Maybe we would’ve found success one day too.
In the end, we were ready to move on, and that’s that. Nothing to be ashamed of.
The most important thing I’ve learned about this experience is that being a founder is equally as exhilarating and fun as it is unrelentingly demoralizing, exhausting, and lonely. Nobody believes in your business like you do (until you find any hint of success).
I often found myself ashamed and even embarrassed to talk about my “startup” with strangers. I don’t know how normal that is. When I had nothing to show for my hard work I felt like an idiot, but when I did I felt like the smartest person in the room (which was very rare).
If you want to start a company, find people you can lean on. If you don’t have a support system, you’ll probably give up.
My co-founder and I had an amazing support system. Our stakeholders cared so much and were unreasonably giving of their time. We were awarded incredible opportunities that gave us all the resources we needed to be successful. It still sucked a lot along the way, but we had every ability to succeed. We just didn’t.
We would’ve given up way sooner without the help and guidance we received along the way. We are extremely grateful for that.
Chapter XII — Life after Heyday
What I wrote in May 2021:
After we had formally quit pursuing Heyday as a startup over winter break, we were in a weird spot with our Design Studio program in which we had to keep working for another semester before our graduation in May 2021.
We kept things light. We built things that sounded fun to build. We secretly hoped for an overnight explosion in growth, but it never happened… though a random kinda-viral TikTok in late April of 2021 almost convinced us to get back in the game:
Jacob went off to pursue a product management position at a Lincoln-based fintech startup called Crescent, which was a consumer-facing app at the time. I went off to do some product and engineering work for a KC-based govtech company called PayIt.
We both remain interested in starting companies again, but who knows what’s next for me — this was mostly a way to document the transformative experience that was Heyday.
Maybe one day I’ll start a successful startup and look back on this and laugh. Startups are hard! But it’s about the journey, duh.
Me, wrapping up this article in October 2023:
Woo! This was quite a “journey”, as my 22-year-old self called it. At 25 years old, I now look back with fondness on the holistic experience, though I know my vision is cleared by the perspective I simply didn’t have at the time.
Why did I want to start a company? I wish I could ask my younger self. My hunch is that I would’ve provided a mostly-BS explanation about the ethical value of the work, but it was probably some convergence of creative curiosity, ego, unsatisfied ambition, desire for wealth, jealousy, boredom, social pressure, desire for personal growth, etc.
Most founders seek fortune. They start with this ambition and work towards a company that will deliver it, much like they start with the solution and work towards the problem it solves.
Do I?
I’m still yet to dive into my next startup. I’ve been working on lots of things since graduation alongside my fun day job at PayIt, including a social app for live sports called FanCave, some contract work and a few little side projects. You can dive into all of my endeavors on my personal site ⚡️
Thank you for reading!