Over one year ago, I decided to quit my data science job and pursue my bootstrapped data science side-project full time. It was a hard decision to make, but once I quit and was freed from the corporate nine to five, my life turned to complete bliss.

That bliss lasted about two weeks before it reverted back to the mean. Honeymoons exist in all facets of life, and bootstrapping a business does not make you impervious to Mondays. Rather every day just became a Thursday. But more on that later...

I wanted to reflect on this past year plus of bootstrapping and add in some frameworks for why anyone reading this on the fence of quitting their job for their side-hustle should do so. Quitting was one of the hardest decisions that I had to make, but the best one I went through with. It's also a decision that many people should not do.

But for the small percentage of the people out there, bootstrapping a startup can be an awesome thing. You resign yourself to make trades.

You trade a steady stream of work and meetings for flexibility in your own time and hours. You trade your current monthly salary now for no income but with future options of money. And you trade office externalities and politics for taking full control of how your career might turn out.

And ultimately if those trades and values are worth it, then quitting your job can make sense in a very real way.

How it got started

On November 1st 2019, I officially quit my job as a data scientist at Nextdoor after working there for exactly a year. I had started a side project called Interview Query with my co-founder, Shane, six months prior.

Interview Query started out as an email newsletter that each day sent a user a data science interview question, and then the solution the next day if the user upgraded to premium. Over the past year we’ve built the product into a fully-fledged data science course, questions database, and became the de-facto data science interview prep resource.

Interview Query SQL
An example of a SQL interview question we would send out. If you paid for premium, we would send a detailed explanation + solution the next day. 

The first time someone purchased a subscription in June of 2019, my co-founder Shane was convinced it was a stolen credit card. It took five more customers before he truly believed that we were not just a test platform for fraudsters. And we watched in fascination as our newsletter grew from $60/mo in revenue to $3,000/mo in revenue.

And while $3K/mo was a lot of money, it still wasn’t enough to constitute quitting our jobs. Shane was working part-time on it while also working a software engineering job. And I was also a pretty senior data scientist making $160K/year. So an apples to apples comparison of going from to $14K/month to $1.5K/month didn’t really seem worth it.

But direct income  isn’t the only comparison you have to make.

Opportunity Cost

The hardest jump to make is almost always on money. Money has always had significance to me. I was born and raised as a Chinese American which meant money was and still is an intrinsic part of my identity. The comedian Ronnie Chieng does a funny bit on what money means to Chinese people.

“Do you know what the direct translation of Happy New Year in Mandarin is? Hope - you - get - rich. That's not Happy New Year!"

To my Chinese parents, they could have added an addendum of - Hope you get rich while working a stable job with low risk. For with all monetary pursuits, the equation that works best within typical Chinese American families is:

Current income * very stable job * years of working = Best Possible Outcome Ever

It’s a pretty linear expectation of wealth that requires a normal day to day grind and the advantages of compound interest. But the equation never really took into account tweaking the risk factor. What happens when your current income drops and risk tolerance increases?

This was the pivotal question that made it difficult for me to quit. But a month before I ended up leaving, I met up with my old startup boss at a company where we exited into an acquisition. I told him about the dilemma I was in, and he illustrated a newer way of looking at it.

If you have a product that’s making $3K/month and you can grow that into $5K/month in a few months by working full time on it, you have to realize that the actual added value of growing your business is turning it from $36K/year in revenue to $60K/year in revenue.

This realization helped me understand the value investment of full-time work. Money and finances can be traded for time and investment in a business in ways that you can't when you work a job. Work your ass off for a year at any FAANG type of tech company and your boss will reward you with a 15% raise. Work hard on your business and double your monthly revenue after a year, well your business also just doubled in value.

So the opportunity cost of trading a job that made me $160K/year didn’t seem that bad anymore if I could at least forecast a rate of growth that would be worth my time and investment as if I was working another full time job.

And at least on my own business, I’d enjoy the work.

Flexibility and Values

Everything gets destroyed when you bulldoze a building. The walls, the appliances, even parts of the foundation. And while throwing a wrecking ball into the corporate 9-5 felt gratifying, picking up the pieces to rebuild exactly how I would work took just as much careful planning and thought.

Balancing structure and life is important when bootstrapping. A lifestyle business allows you flexibility in how you would like to run your business. Before I quit my job, I talked to a career coach (ironically employed by the company) who encouraged me to figure out my values - and try to see if quitting allowed me to prioritize them accordingly.

Eventually I realized it did when I wanted to re-prioritize my activity list from:

  1. Data science job
  2. Surfing
  3. Side-Hustle (Interview Query)
  4. Friends and Relationships
  5. Random data projects


  1. Surfing
  2. Interview Query
  3. Friends and Relationships
  4. Random data projects
  5. Things I don’t want to do but have to do to make money

This clear order of change in my lifestyle made me realize that valuing flexibility was extremely important. It was also something I couldn't attain in my day job.

For example, when an amazing swell approaches Ocean Beach now, I reschedule meetings, log off, and go surfing. Shane and I both have trust that I'm going to finish the work that needs to get done. But if I were to receive a meeting at my old job that conflicted or I didn't want to attend - there was no way around it.

As controllers of our own fate, we make it a priority to cut down all the things we don’t want to do, and hire for those roles. If we need vacation time, then we take it.

But on that note of flexibility comes the other way - how flexible can we be while still working? And how much did we really want to work in general?

Financial Independence of Sorts

In February of 2020, Interview Query was churning out a consistent $9K/month in revenue. We tripled revenue by increasing our distribution and had transitioned from the email newsletter to building a very simple interface for viewing all of the interview questions and solutions. It was also enough to now cover my rent and general expenses.

Our current interface - much improved from before

And better yet we still weren’t even working that much. I had taken a long vacation in New Zealand and Shane was still working part time. For a moment, it seemed like it was going to be a 4-hour work week kind of business that we could maintain without adding new product features.

But realistically, I had nothing else to work on. I still hadn’t gotten any of my other side-projects off the ground at the time. Surfing season was slowly ramping down. I looked around at what I was doing and realized that this project was the only one working and growing on its own. So why not invest to work on it?

One of my favorite ice breakers is asking people what they would do with their life if they received $10,000/month forever. Kind of like a basic (wealthy) income. Many people say travel (which seems illogical given the extent of traveling for the rest of your life), others say they’d make music, volunteer full time, work on making furniture, even working at a boba shop.

Our New Zealand van!

It’s a thought experiment on the idea of financial independence (FIRE). And at its core, the question is asking about what you would practically do for the rest of your life if money wasn’t an issue. The current existence of career advancement is fueled by a never-ending competition in monetary and title status. But if those were all stripped away, what would be left to complete life satisfaction?

I realized there was nothing else I wanted to do but build a startup anyway. Of course money will always matter and I inherently want to grow the business bigger and bigger. But what happens when it’s just a question of: what do I do with my time when my expenses are accounted for and I want to be productive?

Many people in the FIRE community seem to be at loss when they finally achieve their financial freedom. They grind at a job for 15 years to finally quit and reach the same elation that I felt for maybe a few weeks or even months to suddenly fall back into a depression of sorts. Their life has no purpose after hitting their number. Which makes sense, because for 15 years all they knew about was the grind and all they thought about was hitting their number.

I personally love startups and businesses. Building and running companies requires the experience and skillset to get better at doing so. And so the question posed that helped me understand things was:

Would you rather be completely financially independent at age X and then quit your job to try a startup, or get good at building startups now and be a complete pro at age X instead?

Buy Futures in Yourself

The first few weeks after quitting my job I enjoyed the classic freedom and flexibility I had always envisioned. And then all of a sudden the insomnia kicked in. There was no real reason for it but I found myself waking up at 4 in the morning and not being able to fall back asleep for a few weeks.

What is going on? I’m doing my dream lifestyle business full-time, it’s making money, and I can’t just sleep through the night?

I don’t know what caused it, but I can guess that there was a general stress and anxiety that came from transitions in life. And it was the kind of stress and anxiety that wasn’t really tangible. It doesn’t ruminate on the front of my brain until I cry in frustration. Rather I think it was a combination of irrational fears that just took hold of me for just a few seconds.

What if the business stops making money?
What if I have to find another data science job after being out of the workforce for so long?
What if I’m stuck in a 9–5 forever after failing this time?
Shouldn’t I just go back to a job and make two incomes?

I realized later that this kind of thinking was completely irrational. These questions should be asked, but they shouldn't be asked in a way that brings doubt into my personal goals.

And it’s very easy to say. “You’re being irrational Jay! Get back to it”. But it’s much harder to implement in practice, aka getting your brain to believe in you.

Ultimately what helped me is having confidence that no matter what I tried my best on, at the end I would succeed. It’s not universally true. But creating a business gives you valuable experience other people don't have. That experience isn't taken lightly even if you fail and end up going back into the workforce.

It's a by-product of a belief in many different things. Success from quitting your job and starting a company can be defined in many ways. But to me it was realized when I felt that my execution, my value, and my judgement was worth more than what my employer was giving me in return.

Last Thoughts

Currently Interview Query has grand goals for 2021. We've escaped most of the tougher hurdles of proving our business is worth the effort in building out.

Our goals have changed as we've grown in size. Initially it was just to make some side income and write a newsletter. Then it was to cover rent and expenses and create a data science course. And now our goals are on growth and continued expansion of bringing together a community for anyone who's interested in a data science career.

Personally at some point in my life I can imagine that this won’t be what I want to do anymore. I’ll jump back into a job, or maybe quit tech all together and write full-time. But right now it's really fun. And if you're interested in joining along as well, I definitely encourage it.

If you'd like to follow along, create an account on Interview Query to receive some more emails from me. Or you can subscribe to my personal newsletter where I occasionally write interesting things.