Personal-Expression3•This week
I Watched My Startup Slowly Dying Over Two Years: Mistakes and Lessons Learned
If you are tired of reading successful stories, you may want to listen to my almost failure story. Last year in April, I went full-time on my startup. Nearly two years later, I’ve seen my product gradually dying. I want to share some of the key mistakes I made and the lessons I’ve taken from them so you don't have to go through them. Some mistakes were very obvious in hindsight; others, I’m still not sure if they were mistakes or just bad luck. I’d love to hear your thoughts and advice as well.
Background
I built an English-learning app, with both web and mobile versions. The idea came from recognizing how expensive it is to hire an English tutor in most countries, especially for practicing speaking skills. With the rise of AI, I saw an opportunity in the education space. My target market was Japan, though I later added support for multiple languages and picked up some users from Indonesia and some Latin American countries too. Most of my users came from influencer marketing on Twitter.
The MVP for the web version launched in Japan and got great feedback. People were reposting it on Twitter, and growth was at its peak in the first few weeks. After verifying the requirement with the MVP, I decided to focus on the mobile app to boost user retention, but for various reasons, the mobile version didn’t launch until December 2023— 8 months after the web version. Most of this year has been spent iterating on the mobile app, but it didn’t make much of an impact in the end.
Key Events and Lessons Learned
Here are some takeaways:
Find co-founders as committed as you are
I started with two co-founders—both were tech people and working Part-Time. After the web version launched, one dropped out due to family issues. Unfortunately, we didn’t set clear rules for equity allocation, so even after leaving, they still retained part of the equity. The other co-founder also effectively dropped out this year, contributing only minor fixes here and there.
So If you’re starting a company with co-founders, make sure they’re as committed as you are. Otherwise, you might be better off going solo. I ended up teaching myself programming with AI tools, starting with Flutter and eventually handling both front-end and back-end work using Windsurf. With dev tools getting more advanced, being a solo developer is becoming a more viable option. Also, have crystal-clear rules for equity—especially around what happens if someone leaves.
Outsourcing Pitfalls
Outsourcing development was one of my biggest mistakes. I initially hired a former colleague from India to build the app. He dragged the project on for two months with endless excuses, and the final output was unusable. Then I hired a company, but they didn’t have enough skilled Flutter developers. The company’s owner scrambled to find people, which led to rushed work and poor-quality code which took a lot of time revising myself.
Outsourcing is a minefield. If you must do it, break the project into small tasks, set clear milestones, and review progress frequently. Catching issues early can save you time and money. Otherwise, you’re often better off learning the tools yourself—modern dev tools are surprisingly beginner-friendly.
Trust, but Verify
I have a bad habit of trusting people too easily. I don’t like spending time double-checking things, so I tend to assume people will do what they say they’ll do. This mindset is dangerous in a startup.
For example, if I had set up milestones and regularly verified the progress of my first outsourced project, I would’ve realized something was wrong within two weeks instead of two months. That would’ve saved me a lot of time and frustration. Like what I mentioned above, set up systems to verify their work—milestones, deliverables, etc.—to minimize risk.
Avoid red ocean if you are small
My team was tiny (or non-existent, depending on how you see it), with no technical edge. Yet, I chose to enter Japan’s English-learning market, which is incredibly competitive. It’s a red ocean, dominated by big players who’ve been in the game for years. Initially, my product’s AI-powered speaking practice and automatic grammar correction stood out, but within months, competitors rolled out similar features.
Looking back, I should’ve gone all-in on marketing during the initial hype and focused on rapidly launching the mobile app. But hindsight is 20/20.
'Understanding your user' helps but what if it's not what you want?
I thought I was pretty good at collecting user feedback. I added feedback buttons everywhere in the app and made changes based on what users said. But most of these changes were incremental improvements—not the kind of big updates that spark excitement.
Also, my primary users were from Japan and Indonesia, but I’m neither Japanese nor Indonesian. That made it hard to connect with users on social media in an authentic way. And in my opinion, AI translations can only go so far—they lack the human touch and cultural nuance that builds trust. But honestly I'm not sure if the thought is correct to assume that they will not get touched if they recognize you are a foreigner......
Many of my Japanese users were working professionals preparing for the TOEIC exam. I didn’t design any features specifically for that; instead, I aimed to build a general-purpose English-learning tool since I dream to expand it to other markets someday. While there’s nothing wrong with this idealistic approach, it didn’t give users enough reasons to pay for the app.
Should You Go Full-Time?
From what I read, a lot of successful indie developers started part-time, building traction before quitting their jobs. But for me, I jumped straight into full-time mode, which worked for my lifestyle but might’ve hurt my productivity. I value work-life balance and refused to sacrifice everything for the startup. The reason I chose to leave the corp is I want to escape the 996 toxic working environment in China's internet companies. So even during my most stressful periods, I made time to watch TV with my partner and take weekends off.
Anyways, if you’re also building something or thinking about starting a business, I hope my story helps. If I have other thoughts later, I will add them too. Appreciate any advice.
