Reflections on the closed company Hola! Dating app

I'll discuss my fuckups as an entrepreneur and CEO. All of them refer to the dating app Hola!, which I co-founded and starred in.

Spring 2021 was when we started. Two techies and two non-techies created a dating app. Pokemon Go and Tinder were combined.

Online dating is a business, and it takes two weeks from a like to a date. We questioned online dating app users if they met anyone offline last year.

75% replied yes, 50% sometimes, 25% usually.

Offline dating is popular, yet people have concerns.

• Men are reluctant to make mistakes in front of others.

• Women are curious about the background of everyone who approaches them.

We designed unique mechanics that let people date after a match. No endless chitchat. Women would be safe while men felt like cowboys.

I wish to emphasize three faults that lead to founders' estrangement.

This detachment ultimately led to us shutting down the company.

The wrong technology stack

Situation

Instead of generating a faster MVP and designing an app in a universal stack for iOS and Android, I argued we should pilot the app separately for iOS and Android. Technical founders' expertise made this possible.

Self-reflection

Mistaken strategy. We lost time and resources developing two apps at once. We chose iOS since it's more profitable. Apple took us out after the release, citing Guideline 4.3 Spam. After 4 months, we had nothing. We had a long way to go to get the app on Android and the Store.

I suggested creating a uniform platform for the company's growth. This makes parallel product development easier. The strategist's lack of experience and knowledge made it a piece of crap.

What would I have changed if I could?

We should have designed an Android universal stack. I expected Apple to have issues with a dating app.

Our approach should have been to launch something and subsequently improve it, but prejudice won.

The lesson

Discuss the IT stack with your CTO. It saves time and money. Choose the easiest MVP method.

2. A tardy search for investments

Situation

Though the universe and other founders encouraged me to locate investors first, I started pitching when we almost had an app.

When angels arrived, it was time to close. The app was banned, war broke out, I left the country, and the other co-founders stayed. We had no savings.

Self-reflection

I loved interviewing users. I'm proud of having done 1,000 interviews. I wanted to understand people's pain points and improve the product.

Interview results no longer affected the product. I was terrified to start pitching. I filled out accelerator applications and redid my presentation. You must go through that so you won't be terrified later.

What would I have changed if I could?

Get an external or internal mentor to help me with my first pitch as soon as possible. I'd be supported if criticized. He'd cheer with me if there was enthusiasm.

In 99% of cases, I'm comfortable jumping into the unknown, but there are exceptions. The mentor's encouragement would have prompted me to act sooner.

The lesson

Begin fundraising immediately. Months may pass. Show investors your pre-MVP project. Draw inferences from feedback.

3. Role ambiguity

Situation

My technical co-founders were also part-time lead developers, which produced communication issues. As co-founders, we communicated well and recognized the problems. Stakes, vesting, target markets, and approach were agreed upon.

We were behind schedule. Technical debt and strategic gap grew.

Bi-daily and weekly reviews didn't help. Each time, there were explanations. Inside, I was freaking out.

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.

If I don't get detailed comments, I start ruining everyone's mood. If there's a systematic violation of agreements without a good justification, I won't join the project or I'll end the collaboration.

What would I have done otherwise?

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

First-time founders should find an adviser or team coach for a strategic session. It helps split the roles and responsibilities.

Most don't understand the issue until it's too late.

My first startup was what entrepreneurs call the hardest. A two-sided marketplace.

Two-sided marketplaces are the hardest startups because founders must solve the chicken or the egg conundrum.

A two-sided marketplace needs suppliers and buyers. Without suppliers, buyers won't come. Without buyers, suppliers won't come. An empty marketplace and a founder striving to gain momentum result.

My first venture made me a struggling founder seeking to achieve traction for a two-sided marketplace. The company failed, and I vowed never to start another like it.

I didn’t. Unfortunately, my second venture was almost as hard. It failed like the second-hardest startup.

What kind of startup is the second-hardest?

The second-hardest startup, which is almost as hard to develop, is rarely discussed in the startup community. Because of this, I predict more founders fail each year trying to develop the second-toughest startup than the hardest.

Fairly, I have no proof. I see many startups, so I have enough of firsthand experience. From what I've seen, for every entrepreneur developing a two-sided marketplace, I'll meet at least 10 building this other challenging startup.

I'll describe a startup I just met with its two co-founders to explain the second hardest sort of startup and why it's so hard. They created a financial literacy software for parents of high schoolers.

The issue appears plausible. Children struggle with money. Parents must teach financial responsibility. Problems?

It's possible.

Buyers and users are different.

Buyer-user mismatch.

The financial literacy app I described above targets parents. The parent doesn't utilize the app. Child is end-user. That may not seem like much, but it makes customer and user acquisition and onboarding difficult for founders.

The difficulty of a buyer-user imbalance

The company developing a product faces a substantial operational burden when the buyer and end customer are different. Consider classic firms where the buyer is the end user to appreciate that responsibility.

Entrepreneurs selling directly to end users must educate them about the product's benefits and use. Each demands a lot of time, effort, and resources.

Imagine selling a financial literacy app where the buyer and user are different. To make the first sale, the entrepreneur must establish all the items I mentioned above. After selling, the entrepreneur must supply a fresh set of resources to teach, educate, or train end-users.

Thus, a startup with a buyer-user mismatch must market, sell, and train two organizations at once, requiring twice the work with the same resources.

The second hardest startup is hard for reasons other than the chicken-or-the-egg conundrum. It takes a lot of creativity and luck to solve the chicken-or-egg conundrum.

The buyer-user mismatch problem cannot be overcome by innovation or luck. Buyer-user mismatches must be solved by force. Simply said, when a product buyer is different from an end-user, founders have a lot more work. If they can't work extra, their companies fail.

Know why it's important.

The entrepreneur I was meeting with said, "I should be doing crypto, or maybe AI? Aren't those the hot spots? I should look there for a startup idea.”

I shook my head. Yes, they're exciting, but that doesn't mean they're best for you and your business.

“There are different types of entrepreneurs?” he asked.

I said "obviously." Two types, actually. Knowing what type of entrepreneur you are helps you build the right startup.

The two types of businesspeople

The best way for me to describe the two types of entrepreneurs is to start by telling you exactly the kinds of entrepreneurial opportunities I never get excited about: future opportunities.

In the early 1990s, my older brother showed me the World Wide Web and urged me to use it. Unimpressed, I returned to my Super Nintendo.

My roommate tried to get me to join Facebook as a senior in college. I remember thinking, This is dumb. Who'll use it?

In 2011, my best friend tried to convince me to buy bitcoin and I laughed.

Heck, a couple of years ago I had to buy a new car, and I never even considered buying something that didn’t require fossilized dinosaur bones.

I'm no visionary. I don't anticipate the future. I focus on the present.

This tendency makes me a problem-solving entrepreneur. I identify entrepreneurial opportunities by spotting flaws and/or inefficiencies in the world and devising solutions.

There are other ways to find business opportunities. Visionary entrepreneurs also exist. I don't mean visionary in the hyperbolic sense that implies world-changing impact. I mean visionary as an entrepreneur who identifies future technological shifts that will change how people work and live and create new markets.

Problem-solving and visionary entrepreneurs are equally good. But the two approaches to building companies are very different. Knowing the type of entrepreneur you are will help you build a startup that fits your worldview.

What is the distinction?

Let's use some simple hypotheticals to compare problem-solving and visionary entrepreneurship.

Imagine a city office building without nearby restaurants. Those office workers love to eat. Sometimes they'd rather eat out than pack a lunch. As an entrepreneur, you can solve the lack of nearby restaurants. You'd open a restaurant near that office, say a pizza parlor, and get customers because you solved the lack of nearby restaurants. Problem-solving entrepreneurship.

Imagine a new office building in a developing area with no residents or workers. In this scenario, a large office building is coming. The workers will need to eat then. As a visionary entrepreneur, you're excited about the new market and decide to open a pizzeria near the construction to meet demand.

Both possibilities involve the same product. You opened a pizzeria. How you launched that pizza restaurant and what will affect its success are different.

Why is the distinction important?

Let's say you opened a pizzeria near an office. You'll probably get customers. Because people are nearby and demand isn't being met, someone from a nearby building will stop in within the first few days of your pizzeria's grand opening. This makes solving the problem relatively risk-free. You'll get customers unless you're a fool.

The market you're targeting existed before you entered it, so you're not guaranteed success. This means people in that market solved the lack of nearby restaurants. Those office workers are used to bringing their own lunches. Why should your restaurant change their habits? Even when they eat out, they're used to traveling far. They've likely developed pizza preferences.

To be successful with your problem-solving startup, you must convince consumers to change their behavior, which is difficult.

Unlike opening a pizza restaurant near a construction site. Once the building opens, workers won't have many preferences or standardized food-getting practices. Your pizza restaurant can become the incumbent quickly. You'll be the first restaurant in the area, so you'll gain a devoted following that makes your food a routine.

Great, right? It's easier than changing people's behavior. The benefit comes with a risk. Opening a pizza restaurant near a construction site increases future risk. What if builders run out of money? No one moves in? What if the building's occupants are the National Association of Pizza Haters? Then you've opened a pizza restaurant next to pizza haters.

Which kind of businessperson are you?

This isn't to say one type of entrepreneur is better than another. Each type of entrepreneurship requires different skills.

As my simple examples show, a problem-solving entrepreneur must operate in markets with established behaviors and habits. To be successful, you must be able to teach a market a new way of doing things.

Conversely, the challenge of being a visionary entrepreneur is that you have to be good at predicting the future and getting in front of that future before other people.

Both are difficult in different ways. So, smart entrepreneurs don't just chase opportunities. Smart entrepreneurs pursue opportunities that match their skill sets.

And why we must keep arming Ukraine

Russian expatriates write about horrific news from home.

Read this from Nadin Brzezinski. She's not a native English speaker, so there are grammar errors, but her tale smells true.

Terrible truth.

There's much more that reveals Russia's grim reality.

Non-leadership. Millions of missing supplies are presumably sold for profit, leaving untrained troops without food or gear. Missile attacks pause because they run out. Fake schemes to hold talks as a way of stalling while they scramble for solutions.

Street men were mobilized. Millions will be ground up to please a crazed despot. Fear, wrath, and hunger pull apart civilization.

It's the most dystopian story, but Ukraine is worse. Destruction of a society, country, and civilization. Only the invaders' corruption and incompetence save the Ukrainians.

Rochester, NY. My suburb had many Soviet-era Ukrainian refugees. Their kids were my classmates. Fifty years later, many are still my friends. I loved their food and culture. My town has 20,000 Ukrainians.

Grieving but determined. They don't quit. They won't quit. Russians are eternal enemies.

It's the Russian people's willingness to tolerate corruption, abuse, and stupidity by their leaders. They are paying. 65000 dead. Ruined economy. No freedom to speak. Americans do not appreciate that freedom as we should.

It lets me write/publish.

Russian friends are shocked. Many are here because their parents escaped Russian anti-semitism and authoritarian oppression. A Russian cultural legacy says a strongman's methods are admirable.

A legacy of a slavery history disguised as serfdom. Peasants and Princes.

Read Tolstoy. Then Anna Karenina. The main characters are princes and counts, whose leaders are incompetent idiots with wealth and power.

Peasants who die in their wars due to incompetence are nameless ciphers.

Sound familiar?