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Interview with a Successful Startup Founder

Growing a SaaS to $40,000/year while freelancing

Jen Yip
Jen Yip
June 3, 2020
Category of startup
Country of startup
Revenue of startups
Interview with a Failed Startup Founder

Growing a SaaS to $40,000/year while freelancing

Jen Yip
Jen Yip
June 3, 2020
Category of startup
Country of startup
Cause of failure of the startup

After working at Twitter for 4 years, co-founding a pet-health startup in Silicon Valley, and going on an 8-month adventure abroad, Jen founded Lunch Money, a subscription-based personal finance & budgeting web app. She has grown it to +$3k/mo while working as a freelancer for other companies.



Hi Jen! What's your background, and what are you currently working on?

Hi! I’m the founder, engineer, designer, customer support, and all-in-all one-woman team at Lunch Money, a subscription-based personal finance & budgeting web app.

Lunch Money's pic

I started learning basic web programming (HTML, CSS, PHP, JavaScript) at the tender age of 13 after my older sister suggested that I try my hand at making websites instead of wasting my time playing online games (Neopets!). I was instantly hooked and I remember spending my mornings, evenings, and entire summers in front of the computer with Paint Shop Pro and Notepad crafting all sorts of different websites.

My love for computers only grew fonder over the years. Eventually, I attended the University of Waterloo in Canada and I graduated with a degree in computer engineering.

I’m based in Toronto as a digital snowmad, meaning I aim to spend the harsh Canadian winters abroad in Asia. Last year, my husband and I spent 4 months in Fukuoka, Japan, where the first iteration of Lunch Money was built. This year, my husband and I are in Taipei, Taiwan.

What's your backstory?

I spent the first 4.5 years of my career in Silicon Valley where I worked as a software engineer at Twitter for almost 4 years, experiencing both its startup heydeys and post-IPO growing pains. Eventually, I quit and co-founded a start-up with my roommate in the pet health space. We worked on the company together for a year, during which we went through the first batch of YC Fellowship and 500 Startups (both are seed accelerators).

Shortly into 500 Startups, I came into a general realization that this wasn’t where I wanted to be, especially not as a 26-year-old with so many aspirations beyond the Silicon Valley dream. They say the average age of a start-up is 7 years before it dies or gets acquired, and it spooked me to think the rest of my 20s could be spent chasing this singular dream and “maybe” or “maybe not” succeeding.

Eventually, I made the difficult decision of leaving the start-up. My co-founder was more than capable of running the company on her own and we parted ways on good terms.

Burn-out is a very real feeling and can catalyze some pretty crazy changes. I ended up diving really deep into minimalism, no longer wanting to bear the responsibility of anything aside from the minimum necessities. I gave away or sold almost all my stuff. I said goodbye to my friends and the city I called home for the last 5 years with no regrets and I was ready to finally start living life on my own schedule.

After spending 2 months at home reconnecting with my parents with a newly-refreshed mind, I ended up on an 8-month adventure abroad where I deliberately sought out experiences that would take me far away from anything computer or tech-related. Here’s a sample of what I ended up doing:

I also did some good ol’ fashioned traveling through amazing cities such as Lyon, Tallin, Stockholm, and Copenhagen.

At the end of it all, my parents met me in France and I wrapped up my sabbatical by showing them around my new favorite country for 2.5 weeks. I flew back to Toronto and started the next phase of my life in the city I grew up in and was joined by my now-husband who was also on his own sabbatical during this time.

We spent the first few months back in Toronto enjoying each other’s company and re-discovering Toronto as residents. By this point, I hadn’t done any programming in almost 1.5 years and as is expected in the world of software development, a lot had changed. 

For the next two months, I went to a coffee shop every day to catch up. I decided to learn React and I eventually released a fully-functioning app to the App Store– a Chinese phrasebook app inspired by my own travels. It has almost no downloads aside from my mom.

While I didn’t gain any riches from this app, I did gain the skills necessary to pick up some freelancing jobs. Through my network, I worked as a freelance software engineer for three different companies over the span of the next 2 years, each having different roles and responsibilities ranging from web development to full-stack engineering. 

My husband and I were having a great time in Toronto but we realized we didn’t love it so much during the winter. We were both fully remote in our jobs, so why not take the opportunity to scratch our itch to travel and go abroad during that time? 

In 2019, we kicked off our “digital snowmad” lifestyle by spending a winter abroad in Fukuoka, Japan. During my time there, I was able to work on a few personal goals (learn Japanese cuisine, learn elementary Japanese). I was also continuing to freelance for 2 different companies while starting to work on what is today known as Lunch Money!

How did you come up with Lunch Money’s idea and build it?

The idea of Lunch Money started when my husband and I first moved to Toronto. Since I hadn’t been tracking my spending consistently during my sabbatical, I figured it would be a good time to start doing so since we were now more permanently settled and starting to share our finances. I started a Google Sheet and we diligently tracked all our spending for months. Since we were still traveling a lot, this Google Sheet also had to take into account multiple currencies and exchange rates. It quickly became too much to manage.

I always had the idea to turn our spreadsheet into the app – I knew that if I could break out of the confines of Google Sheet, I could build something that was better designed with more computational freedom. I finally decided that I would start working on this initiative in Fukuoka. The plan was to decrease my freelancing hours to free up more time for this new endeavor.

The initial designs were done in Sketch and I followed very closely the layout of my Google Sheet. I picked my stack to be a mix of familiar (React, Node.js, Postgresql) and unfamiliar (Semantic UI, Typescript, Redis).

From January to April while we were in Fukuoka, my schedule was more or less like so:

  • Wake up at 7:30am to attend stand-up for one of my freelancing companies
  • Work 2 hours for company #1 and another 2 hours for company #2
  • Go to the gym
  • Come home and cook lunch (a.k.a. practice cooking using Japanese ingredients!)
  • Finish lunch and head to a co-working space to hammer out Lunch Money work, usually from 2:30pm until 7pm when our stomachs would start grumbling.
  • Go out for dinner
  • Go home and work until we sleep (usually another 3 more hours of Lunch Money work)

I don’t think I have ever been so disciplined in anything else in my life, but then again it’s hard to think of another time in my life when I was so motivated by what I was doing. It had been a long time since I have been consumed by a programming project and I was loving every single minute of it.

My first goal was to get an MVP that my husband and I could use. I achieved this in early February. My second goal was for us to get completely off of our spreadsheet. I achieved this one month later in early March. 

I started collecting private beta sign-ups via a simple landing page with a few screenshots between February and June. It was a long and arduous process to implement all the features I wanted for private beta and to polish everything up. Finally, in July, I launched a private beta to a group of about 50 friends and a few strangers.

For the next few weeks, I collected feedback and worked tirelessly to continuously improve the product. I hadn’t thought about anything related to marketing or pricing– I just wanted to make my early adopters love the product first. 

It was time to think about pricing. From my previous experience at the pet health start-up, I knew that I would not offer a free tier. We offered a free tier before and it was demoralizing spending so much time answering support emails from people who were never going to pay us for our time. I landed on a free trial which would eventually convert into a monthly or yearly plan. I picked an initial pricing of $3/month or $29/year which I felt was reasonably low for anyone to give my app a chance!

In mid-August, I started having this sinking feeling that not having a solid marketing strategy was going to be my downfall. I had no real plan on how to get more users and my few attempts at posting on Reddit got me banned from some of the most popular finance-related subreddits. Not a great start.

Then one day, on a whim, I decided to post a Show HN on Hacker News to introduce my product. Long story short, I ended up #1 on Show HN and on the front page for almost 24 hours. I got nearly 1000 signups within just a few hours! I stayed up that night responding to every single support email and diligently adding tasks to my Asana. I couldn’t believe that complete strangers were actually excited about something I had built! It took a few days to realize that I was now in a new phase of Lunch Money and there was no going back.

Which were your marketing strategies to grow your business?

By no means am I a marketer. I am through and through an engineer with an engineer’s brain (plus maybe a bit of a designer’s brain, too). But to make it clear, it’s hard for me to understand what moves the needle and how to measure the effectiveness of different strategies.

That being said, I’ve tried a number of things, such as: reaching out to journalists, replying to random people on Twitter or Reddit, buying ads, etc.

None of it worked. And I didn’t particularly love inserting a sales pitch into random people’s lives for a product that wasn’t totally fleshed out.

So I continued to do what I love doing, which is 1. improving Lunch Money, and 2. sharing my stories through writing.

Lucky for me, both of these have in one way or another contributed to the biggest spikes I have experienced thus far. Writing about my experience as a solo founder and posting them on mediums such as Hacker News, LinkedIn, Twitter and Indie Hackers have proven to be most successful in drawing new users to Lunch Money. And continuously improving Lunch Money keeps my current users happy and drives word-of-mouth marketing.

As of now, word-of-mouth marketing and blogging are my best marketing tactics. Word-of-mouth is great because it’s effortless on my part and will grow naturally as I continue to invest in my user’s happiness and satisfaction. Blogging about my experiences and learnings is something that I love to do and I always try to find new and interesting angles to write from.

Here are some recent examples of how these tactics helped Lunch Money grow:

  • A few users commented and recommended Lunch Money on a Hacker News post of an article about the downfall of Mint. The comment was probably about 10 comments down from the top, but still drove over 300 signups.
  • A famous Dutch tech influencer Tweeted about Lunch Money and drove over 200 signups.
  • My recent blog post, "The biggest mistakes I’ve made with Lunch Money (so far)", made it to the front page of Hacker News and drove over 500 signups.

The best part is that all of these are compounding since more and more people will become aware of Lunch Money. My recent blog post which first gained exposure on Hacker News ended up being mentioned by a few other publications including a Japanese podcast!

What are your goals for the future?

This is a very loaded question, so I’ll try my best to answer this from various angles.

Revenue-wise, the dream is to have Lunch Money match the income I would be making had I stayed in Silicon Valley. To me, this would help validate everything I’ve done up to this point.

From a personal philosophical standpoint, I don’t like to set goals too far in the future. I don’t think it’s helpful to have big aspirations when the steps to get there are not clearly defined. In general, I like to set goals that I can see myself attaining in the next 1-3 months, and I like to set new goals often. For instance, I recently hit $35,000 ARR. My next goal is to hit $45,000, then $55,000, and so on! 

In terms of growing the company, I would actually love to continue going at this as a one-woman team. I have come this far on my own, and there’s no reason why I shouldn’t continue and I feel a need to find out for myself just how far I can take this. Of course, I have a great network of friends who are experts in areas I have very little knowledge in so I often tap into them for help. But in terms of growing a team and creating a company out of Lunch Money, it’s not currently on my radar.

And finally, the goal has always been to have Lunch Money eventually make my life easier, not harder :)

What were the biggest challenges you faced and the obstacles you overcame?

The biggest challenges in working on Lunch Money has always been time management and prioritization. When I first started working on Lunch Money, I was splitting my time with 2 other freelancing commitments while living in a country that I was yearning to discover. I wanted to do everything! I knew I needed to make money but I couldn’t stop my brain from thinking about Lunch Money, all while also wanting to explore all the corners of Fukuoka, go on day trips, and spend time with friends and family who took the time to visit us abroad. 

So I guess the issue was that I had too many things that I wanted to do but Lunch Money would always take up a disproportionately large amount of my time and energy. 

To get over this, I realized that I had to reconcile my own feelings of guilt. It felt weird to be in such a privileged position of living abroad in Japan, yet spending almost all my waking hours in front of a laptop. Then I realized, who cares? I was happy. I was feeling fulfilled every day and I felt incredibly lucky to have all this time to work on a side project. I was thriving and I realized I hadn’t felt this way in a long time and I just needed to embrace my new lifestyle.

Which are your greatest disadvantages? What were your worst mistakes?

The biggest disadvantage of starting a personal finance and budgeting app is that building trust with that first cohort of users is very hard. Typically, a beta testing round would include friends and family, but this can be especially difficult when it comes to something as private as finances.

I knew I wasn’t going to try to convince somebody to trust my app with their personal data. That would have to come from within themselves, stemming from a desire to use a product that I created. So the best thing I could focus on to grow my initial user base was to create a product that was irresistible to trial!

No single mistake that I’ve made was detrimental, but I can think of a lot of potential mistakes I could have made which would totally have derailed the progress of Lunch Money. I’d have to attribute the avoidance of these to being a solo founder– since I’m stretched so thin, I don’t actually have time to dive so deep into one thing that I lose sight of where I should be going. I’m constantly re-prioritizing the most important things to do and if something is taking me more than, say, 1 week, I think really hard about whether or not it’s really worth that time.

The biggest mistake I could have made was creating a mobile app pre-launch. Lunch Money’s MVP was a web app and I was continuously haunted by the thought that not having a mobile app would put me at a huge disadvantage. About 3 weeks before my Hacker News launch, I set out to learn an entirely new framework (Flutter) AND programming language (Dart). I followed tutorials, listened to podcasts, and always tried to fit time for mobile app development in between feature improvements and bug fixes. It was a few weeks of frustration with myself that I was so slow to get this mobile app out! Talk about high expectations...

Thankfully, other tasks started piling on so much that I re-evaluated the need for a mobile app and decided that it wasn’t necessary for launch. As a compromise, I priced my product much lower than competitors and hoped for the best.

As it turns out, the demand for a mobile app was not as high as I thought it would be. In fact, after launch, it became apparent that most users were more interested in seeing the product continue to grow and develop, rather than being available on another platform.

If you had the chance to do things differently, what would you do?

To be honest, I don’t think that I would do anything differently. I thoroughly enjoyed the entire process and journey and I wouldn’t trade it for anything else. There are minor things, like being too afraid of launching too early or getting anxious about sending out newsletter campaigns, but in hindsight, it was all necessary for my personal growth as a solo founder. 

What are some sources for learning you would recommend for entrepreneurs who are just starting?

Here are three resources that have inspired me in my journey:

Book: Mindset: The New Psychology of Success by Carol S. Dweck

This book changed the way I viewed my personal growth and provided a new framework to think about self-improvement. I used to read a lot of self-help books thinking that they would make me a better person but none of them have ever stuck the way this has.

Podcast: The Startup Pregnant Podcast

This podcast is for you if you are any number of the following: a woman, an entrepreneur, an aspiring entrepreneur, a mom, a soon-to-be mom, independent, or just simply a bad-ass woman.

Blog: Takuya’s blog about his life as a solo developer on a markdown editing app called Inkdrop was my first exposure to the indie hacker lifestyle. I remember accidentally stumbling upon his story and being in complete awe of what he was doing. His blog is wonderful as he’s totally transparent about the challenges he faces as well as what has worked very well for him to grow his app to a point where it can fully sustain his lifestyle.

Lastly, my friend DK’s blog, “Road to Ramen” is great to follow for anyone interested in the indie hacker’s journey. He blogs candidly every day (yes, every single day!) and it’s a great way to peer inside his mind and witness his learnings along the way– not just related to building a business but also personal development.

Where can we go to learn more?

I am @lunchbag on Twitter, and I also blog at lunchbag.ca where you can sign up for a mailing list in which I send out more personal updates. 

Lunch Money lives at lunchmoney.app and I tweet about new features from @lunchmoney_app.

Some blog posts of interest:


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