The Mistakes That Doomed My Startup—and How to Avoid Them
Kicking things off strong for my very first article, I'm diving into one of the topics that brings me shame: my failed dating app startup. Most startups fail, so I know I'm far from alone in my experience and the shame I feel for not wildly succeeding as I had envisioned in all my grand fantasies and plans. To really twist the knife in the wound, I devoted over three years of my life to it and lost a significant amount of my own and my parents’ money.
But with every failure comes all the learnings, and boy, did I fucking learn.
So was it really a failure if I came out better for it? Yes.
I’m not going to sugarcoat it and paint the experience like it was rainbows and sunshine like some of these people gallivanting about. We often try to disguise failures behind other labels: lessons learned, growth opportunities, personal or professional betterment, etc. Those are the positive byproducts, of course, but a failure is a failure.
But I digress. Without further ado, let's dive in.
Intro: I Founded a Dating App
In March 2021, I founded the first and only core values dating app with red flag and deal breaker alerts. A brilliant idea, I know. Who isn't exhausted from dating? I wanted to create an app that saved time and energy in the dating process, providing essential insights about potential dates instead of having to suss them out through texts and conversations in person.
I researched the dating and relationship space, found it endlessly interesting, learned about core values, and created the Pillar Questions. I designed the app, confident that if I built a great product, investors would flock to fund it, and I’d be on my way to creating the next big meaningful dating app. I was so bright-eyed and bushy-tailed. How hard could it be?
snort
rolls eyes
Obviously, I now know better.
Of course, you need to be slightly delusional and extremely optimistic to dive into anything as difficult as starting your own company, but I really didn’t have much of a clue.
By investing my own savings and with some financial help from my parents, I managed to get the app developed, launched, and grew it to around 1,000 users. However, I never secured funding, and momentum slowed to a near halt once the money ran out. The experience became a lesson in the power of the sunk cost fallacy, something I couldn’t escape despite my supposed self-awareness.
That's how I ended up here, with a dating app startup that has pretty much failed, yet I still refuse to shut it down until the last dollar is spent. So, through this long and painful experience that I still managed to have some fun with, what were my biggest takeaways? Let’s get into it.
Lesson No. 1: Build in Public
When it comes to consumer products, especially in tech, you CANNOT build in private or stealth mode, whatever you want to call it.
A fellow founder and part-time investor once told me that marketing doesn't matter much—if you have a good product, people will come. HA! Sir, absolutely not. No. You jest.
If you're building a consumer product, you need to start marketing as soon as possible. If people don't know it exists, it doesn't matter how amazing or groundbreaking your product is; no one will download it, buy it, use it, nada. They do not know about it!
I was naive, thinking I could build awareness and a user base just by running paid social media ads. I soon found out that even running ads was challenging due to red tape around potentially inappropriate content. Even if I had been able to run the ads, it wouldn't have been enough, especially with a product that requires location-specific traction.
The biggest mistake I made was in the marketing department—or rather, the lack of it. Being an introvert did not help me in the slightest. I know I needed to push myself far more to broadcast my ideas and what I was building.
Get on social media, post content, build the thing in public, create a loyal following and community, be loud and proud. Do not repeat my mistakes.
Lesson No. 2: If You’re Looking for Funding, Get the Numbers
If you've decided to raise funds or realized that you'll need outside funding, this one's for you.
Concrete user validation in the form of numbers is your lifeblood as an early-stage startup seeking funding. Before investing considerable amounts of money, ensure the numbers are on your side. Whether it's pre-orders, collecting emails on a waitlist, social media followers, or monthly active users—whatever's applicable to your product—identify the most important indicators of user validation and focus on getting them.
These will be your proof and the hill you'll die on in pitches.
Lesson No. 3: Stay Single-Mindedly Focused
It's not very responsible or noble to blame others, but despite my extremely supportive parents, they eventually became fed up with my startup endeavor. Living with them, their frustration with the lack of momentum—and more specifically, the lack of money—became a strain on our daily interactions.
My focus and energy for the dating app started to drain as I had to defend it and provide progress reports regularly, while also combating their exasperation and doubts. It came to a head when I was given a bit of an ultimatum: find a job and move on. This was the unofficial death knell for my startup, as I was forced to start job hunting while still clinging to the dating app.
All the doubts crept in, and I questioned my life decisions every other day. It was a mess. When you're building something new and high-risk, you cannot lose focus. Your focus, mindset, and belief in what you're doing are the only things you can count on and sometimes the only things that will get you through the really tough, dark pits of despair that inevitably come during the process.
If you lose that, it's like living in a house of cards that tumbles down at the faintest breeze.
Final Thoughts
There were things I did right and things I did wrong; overall, I don't regret the experience. Even though failure tastes bitter, at the very least, I have learned a ton. And trying to find a job has proved to be extremely difficult as well! Woo! So here we are, at the beginning of a second endeavor—albeit a less expensive and hopefully less all-encompassing one. Welcome to the first article of Risky Biscuit Club, where I share hopefully helpful content related to entrepreneurship, starting a business, and other things that tickle my fancy.
Update
Sometimes, even when we think there are no other options and failure is inevitable—that we should just quit instead of clinging to something that's dying—unexpected paths forward open up when we're planning the funeral.
So, one more lesson?
Always keep your eyes peeled and remain receptive to new introductions and opportunities, even when you've lost all hope and don't think anything will come of it. If a door closes, look for an open window.
I designed, built, launched, and managed to gain users and paying subscribers (not a lot, but some is more than none) in three years. Never discount your efforts. It was hard, and I built a product I wholeheartedly believed in. Other like-minded people will feel the same and want to either help or be a part of it.
About the Author
Hi! My name’s Mara, also known as Chief Biscuit Officer. As an introvert, I always felt like being an entrepreneur with my personality was doomed based on all the popular "you-have-to-be-an-aggressive-hustler-master-networker-in-a-big-city" advice. Well, here I am, a 2x founder who’s definitely not that, and I want to build a community for people like me because, no, you don’t need to be an extroverted hustler extraordinaire to succeed as an entrepreneur.
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