Five Years of Bootstrapping: Reflections on Building Interview Query

Turns out running a startup isn't easy

Four years ago I wrote about quitting my job to bootstrap my startup. Reading that post now makes me laugh: the naivety is almost endearing. Back then, I thought I had it all mapped out: build a business, find freedom from the 9-5, and work on my own terms.

Interview Query started with a simple idea: help data scientists prepare for technical interviews. We've since grown into what people call "the Leetcode for data science” and have helped place over 10,000+ people into better-paying jobs. But those numbers don't tell the story of sleepless nights, euphoric highs, or moments I questioned everything.

Here's what really happened in the last five years, and where we're headed next.

From Side Project to Startup (2019 to 2021)

Interview Query was initially conceived from a blog post I wrote on my interviewing experience after working for 2.5 years as a data scientist in a previous startup. I was interviewing at the time for mid-level data science roles and dealing with the onslaught of take-home exercises and technical interview questions. When I finally landed a job and wrote about my experience, I received a surprising amount of inbound on LinkedIn from readers asking for mentorship for their own upcoming interviews. And it took six months of me rejecting their replies until a lightbulb struck in my head that I could build some course content and sell it to them instead.

Still the best converting landing page

The initial idea for Interview Query was simple: we emailed data science interviews questions in a newsletter three times a week to users and paywalled the solutions. I reached out to a good friend and former co-worker and he hacked together the MVP over three painfully long months before we went live. And in six months we hit $3K in MRR, I quit my job and went all in.

The early years were a blur of throwing features at the wall. While I churned out blog posts and YouTube videos to drive traffic, a constant anxiety gnawed at me: were we providing enough value? This would trigger frantic sprints of writing more interview questions and solutions. Meanwhile, our customer interviews kept surfacing the same desperate request ("Just show me what questions Facebook asks!") My co-founder and I wrestled with an impossible challenge, how do we convince users to share their real interview experiences while building the ideal learning platform they needed?

This was an exciting time building the business. With COVID lockdowns starting five months after I quit, I had nothing to do but work. But it was great because not only was I bootstrapping it with my friend, we had no investors to report to, no constraints on growth, and nothing beholden to us except to make enough money to cover our monthly expenses. And once we got to that pivotal $10K in MRR a few months later (I had around $5K in monthly expenses pre-Covid) I felt a weight lift off of my back. For the first time, I had the freedom to work on the project without worrying about money.

Then as Covid continued on, it ushered in extreme growth in tech education. And as we built out more features like a question bank, courses, learning paths, and code submitters, our business was slowly growing. By the end of 2020 we were doing around $30K to $40K in MRR and I was still not burning out from juggling Youtube creator work, writing questions and courses, and figuring out product direction as CEO.

In 2021 I finally moved out of SF and moved to Hawaii for four months to escape Covid lockdowns. Then later that year, as Covid started to ease off, my girlfriend and I continued slowmadding, trying new cities like NYC and LA. After hiring our first engineer, my co-founder and I remained committed to running a high-margin lifestyle business. This was despite watching members on Interview Query land $300K+ salary offers or reading about startups on HackerNews raising crazy amounts of venture funding. We had ambitions to grow, but wanted to stay true to our original vision: building something sustainable on our own terms.

Chasing Growth (2021 to 2022)

A single conversation in late 2021 changed my entire perspective. It was with another bootstrapped company in our space, one I'd been watching closely, thinking they were maybe a year ahead of us in growth. The moment we shared revenue numbers, my assumptions about what was possible shattered.

Our numbers were solid for 2021: $650K in annual revenue, triple what we'd done in 2020. But growth was slowing and we'd be lucky to hit 50% in 2022. Then they shared their story: one year ago, they'd been exactly where we were. Now? They were running at $4 million a year.

Example of an Interview Query SQL question

I kept my poker face, but my mind was racing. I had never actually calculated our market size, I just assumed we were near our ceiling. I also didn’t believe that they were 10x smarter than us. And so there was no reason why we couldn’t do the same thing next year.

At that point in time we were pocketing 75% of the revenue as profit back into our bank accounts. But now knowing what was possible, we doubled down on reinvesting into growth. So at the start of 2022, we committed to hiring more engineers, filming much more Youtube videos, and set much bigger growth targets for 2022 with the goal of at least doubling revenue every year for the next three to five years.

But ironically enough, once I started setting revenue targets, we never hit one again.

From Growth to Survival (2022 to 2023)

By May 2022 I knew that something was wrong. Facebook and Amazon announced hiring freezes after their COVID hiring spree, while Netflix's stock plummeted as growth stalled. Our revenue was stable but falling short of our 2.5x growth target, pushing us to run our first-ever non-Black Friday sales on our premium product offering.

At the same time I was on year two of slowmadding. We traveled to Salt Lake City in the winter for skiing and Santa Cruz in the spring for surfing. In the summer of 2022 my girlfriend and I started going international to places like Vancouver BC, Lisbon, and Scandinavia. Bootstrapping had never been any better. No investor could tell me I couldn’t work from a coffee shop in Lisbon or teach product analytics from my sunny Airbnb in Copenhagen. I was still nervous about the slowdown, but I assumed it wasn’t going to affect us long term because even if tech workers lost their jobs, they would come back to Interview Query.

In the fall of 2022 though, tech stocks crumbled as wall street demanded profitability over growth. The discount sales were not working their magic anymore and we were now just trying to maintain our previous monthly revenue numbers. I watched as our revenues went from $80K/month over the summer to $60K in October and November. Finally in December of 2022, as 150K tech workers got laid off and companies stopped hiring completely, Interview Query’s revenue plummeted to a low of less than $30K. ChatGPT's release that winter also brought a new existential threat: while I was amazed by its capabilities, I also watched in horror as it effortlessly solved the majority of our coding interview prep questions.

We laid off half of our staff and Interview Query was suddenly back to becoming a very lean organization again with just two engineers, myself, and a small offshore ops team. We were still hopeful that revenues would bounce back in January from the influx of laid off workers looking for new jobs. But by mid-month, it was clear no interviews were happening at all and our business was going to stay at this $30K/month range along with many sleepless nights. My co-founder with a baby and another one on the way decided to part ways and work on his own new startup.

I was at what I believed to be rock bottom, but my peers helped me see the bigger picture. This was simply about survival. If we could make it through this downturn, we'd be stronger for whatever came next. So we cut costs and kept building, trusting that the market would recover.

But the old strategy clearly did not work anymore. We spent much of the first few years throwing stuff against the wall expecting it to work because that’s what worked when the tech hiring market was growing. We were never methodical about measuring the impact of new features or A/B testing anything (the irony as a data science product), we just built things we thought customers wanted. But now that the market wasn’t growing, and I couldn’t figure out what to build to increase revenue, I was relentlessly focused on reducing costs and cutting anything that wasn’t necessary.

We spent a few months building peer mock interviews. No regrets but almost no A/B testing happened either during the development…

While a new strategy of selling to universities kept us afloat, I was still burning out. Managing every detail of the business left no energy for growth, and just maintaining felt hollow after our previous success.

Then finally, mid-year through 2023, my girlfriend of five years abruptly left me. We were back in Hawaii for a few months, which was supposedly paradise, but she was unhappy with the last three years of constantly traveling across the world, distanced from family and a consistent community of friends. And so in June, I was running a failing company while also introspectively trying to understand what I was to do as a now single 30 year old guy without a home.

Rebuilding & Reflection (2024)

August 2023 marked the turning point in my year from hell. We launched a lower-priced tier to expand our customer base, and revenue immediately started climbing. The timing couldn't have been better, tech recruiters from FAANG and AI startups were flooding LinkedIn again, signaling the market's recovery.

And by the end of 2023, I had a lot more hope. I spent the summer in NYC, partying with friends and making new connections before deciding to move back to San Francisco permanently. And at the beginning of the new year, I bought a home in the Richmond district and got back together with my girlfriend as we worked to repair our relationship in one spot.

After five years, Interview Query was slowly but surely maturing as a company. Our contractors had evolved into a true team, growing their careers and working seamlessly together, something we celebrated at our first global offsite in Morocco with eight team members. But even as we rebounded, I remained trapped in the same solo founder role, buried in product decisions, sales calls, and operational tasks. And with my PTSD from our last reinvestment in growth, in 2024 I set a growth goal for revenue but with a healthy safety margin of EBITDA. I believed that most of our efforts now would be reducing costs and siphoning money out of the business into new ventures.

In 2023 as Interview Query was flailing, I decided on a whim to start a Vietnamese Coffee Supplement company that would grow quickly in the consumer packaged goods space. But turns out after I spent a month buying bags, mixing powder in my Airbnb, and shipping coffee to friends, no one really wanted it. Consequently when I was in NYC, I helped advise a few friends on their startups and SEO. And had the idea to start a marketing agency after everything I learned at Interview Query. This lasted a couple months before realizing that I didn’t actually love the work even as we were seeing some good initial results.

And so while I started 2024 motivated to run a holding company empire, with Interview Query funding my endless stream of new business ideas, by mid-2024 I was really unsure of why I wanted to manage multiple businesses when I couldn’t even commit to one successfully.

Mid-2024, I bought an hour of Jason Cohen's time. In one brutally honest session, he stripped away every business concern until we reached a simple but profound question: would doubling revenue each year make me happy running this business? My hesitation spoke volumes, pushing me to consider either selling or bringing in a CEO.

Putting both paths into motion, I got extremely close to hiring a CEO. A potential candidate flew across the country to San Francisco, met my old co-founder and I for dinner, and over food and drinks we gave him an offer. But the next week he reneged on the offer last minute after getting his salary doubled from his existing employer.

It was quite disheartening and I decided it was time to take a true one month break off the business to establish what I wanted. My girlfriend and I planned a trip for a month in December to Vietnam and Japan and I tried my best to stay off Slack to rethink the future.

The Next Chapter (2025 and onwards)

Looking back at my reflection from five years ago, my primary desire was for flexibility and freedom to craft my own lifestyle. While I achieved that initial goal, I've realized that you always create new expectations for yourself, no matter how much freedom you have.

As the company matured, this became clearer: should it morph to suit my evolving needs and lifestyle, or should it grow independently of its founders? While I still don't believe every business needs to follow the venture-backed path to billions, the goal posts always move and I've come to realize that sustainable growth is vital for the long-term health of the business.

There's this concept of "Best Owner" philosophy from M&A - the idea that you should constantly evaluate if you're the optimal steward for your business. After much reflection, I realized I still want to be involved, just in a different role, and not one that goes “Founder Mode” into everything right now. This past year, I flirted with new business ideas but instead discovered that the determination and willpower required to create a company from nothing is so immense that it has to be driven by more than just incremental profits or fun side projects.

What keeps me committed to Interview Query is still our mission. It's hard to imagine working toward anything more meaningful than up-skilling as many people as possible into better jobs. For 2025, we've set ambitious but achievable goals. But part of the learning process has been detaching my personal happiness from the company's revenue metrics or outcomes. So if things don’t go according to plan, it’ll still be okay.

One thing I'd love to do this year is talk to more startup founders. If you're someone with wisdom to share, or thinking about starting the journey and need advice, I'd love to connect. Startups are a lonely journey, and I'm realizing that bootstrapping is an even lonelier one without many investors or people looking out for you.

The future remains unwritten, but I'm excited to see how both Interview Query and I can grow together, even if that growth looks different than I originally imagined.