My 3 Big Mistakes As a CEO and Co-Founder | by Evgeny Nelepko | Aug, 2022

Thoughts and self-reflection about the closed company Hola! dating app

My pitch to investors

I want to tell you my story as a founder and CEO and share some examples of my fuck-ups. They all refer to the Hola! Dating app, which I co-founded and played the role of a СЕО.

We started the project in Spring 2021. Four guys (two techs and two non-tech) decided to disrupt the dating app market. The idea was to combine the mechanics of Pokemon Go and Tinder.

We decided to do this because online dating looks like a business process, and it takes two weeks from a like to a date. Also, we asked online dating app users: “Have you meet new people offline last year?”

75% said yes, 50% said sometimes and only 25% said regularly.

People are interested in offline dating but have some red flags:

  • Men are afraid to fail in public
  • Women want to know some background about a person who approached them

And so, we created unique mechanics that allowed people to date immediately after a match. There would be no endless chats. Men would feel like cowboys, and the women would stay safe.

There have been many victories and defeats throughout the journey, but I want to highlight three mistakes that led to detachment between the founders.

This detachment ultimately led to us shutting down the company.

Situation

Instead of making a faster MVP and developing an app in a universal stack for two platforms at once, iOS and Android, I defended the idea that we should set the app on the native platforms, piloting separately for iOS and Android. The skills of the technical founders allowed us to do this.

Self-reflection

This strategy was a mistake. We lost a lot of time on the development of the two apps at the same time and started running out of resources. In the end, we had to focus on iOS, which is a more profitable platform. But Apple kicked us out almost immediately after the release, citing Apple Guideline 4.3 Spam. It turned out that we spent 4 months and were left with nothing. The application wasn’t available on the Store, and we still had a long way to go to get it on Android.

I reasoned that we should immediately prepare a standard platform for the development of the company. This way, it would be easier to strategically develop the product in parallel. Unfortunately, lack of experience and knowledge was coupled with the strategist’s expertise, and it turned out to be a piece of shit.

What would I have done differently?

We should have created a universal stack or Android development in the first place. I knew there would be problems with Apple because it was a dating app.

Our strategy should have been to run something first and then polish the product model, but prejudice prevailed.

The lesson

Take more time to discuss with your CTO the tech stack. It can save time and resources for your company. Choose the easiest way to build and test an MVP.

UX description

Situation

Though the “universe” and other founders told me it was better to find investors before you started doing anything, I started pitching and talking to investors when we almost had an app ready.

By the time some angels came along, it was time to close up shop. The application got kicked out of the store, the war broke out, I left the country, and the other co-founders stayed. We had no investment to fall back on.

Self-reflection

I enjoyed conducting interviews with the users so much. I was very proud to have done over 1,000 interviews. I wanted to dig deeper and deeper into people’s pain points and refine the product better and better.

In reality, the results of the interviews were no longer impacting the product. I was scared to go and start pitching “to the world.” I filled out applications for accelerators, redoing my presentation to no end. There’s nothing scary about that; you have to go through a period like that, so you don’t have to be afraid later.

What would I have done differently?

Get a mentor or a buddy (external or internal) who would guide me to my first pitch, and help me take that step as early as possible. If there were criticism, I’d be supported. If there were enthusiasm, then he would cheer with me.

Taking a leap into the unknown is not difficult for me in 99% of cases, but there are situations when it is difficult for some reason. The mentor support would have encouraged me to take this step before it was too late.

The lesson

Start fundraising as soon as you can. It might take several months. Don’t be afraid to show your project to investors in the pre-MVP stage. Get feedback and make conclusions.

Situation

My technical co-founders were also part-time lead developers, which caused a dichotomy in our heads and our communication. As co-founders, we had excellent communication and understood all the challenges. We had an agreement on key issues of stakes, vesting, target markets, and strategy.

That said, we had an extremely strong deviation from the set timeline. Only the technical debt and strategic gap were growing.

The bi-daily and weekly reviews weren’t helping much. Each time there were reasons that explained what had happened. I pretended to understand, but inside I was freaking out.

Our team

Self-reflection

I am a fairly easy person to talk to. I always try to stick to agreements; otherwise, my head gets stuffed with unnecessary information, interpretations, and emotions.

Sit down -> talk -> decide -> do -> evaluate the results. Repeat it.

Now I know that if I don’t get feedback in the kind of detail that would allow me to draw conclusions, I start messing up the mood of everyone around me. I also know that if there is a systematic violation of agreements without a comprehensible reason, I will not enter the project, or I’d terminate the collaboration.

What would I do differently?

This is where it’s scariest to draw conclusions. Probably the most logical thing would have been not to start the project as we started it. But that was already a completely different project. So I would not have done anything differently and would have failed again.

But I drew conclusions for the future.

The lesson

Find an adviser or a team coach for a strategic session at the beginning of your startup’s journey if you are a first-time founder. It helps split the roles and responsibilities.