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.

It's ok and even desired to be unprofitable if you're gaining revenue at a reasonable cost and have 100%+ net dollar retention, meaning you never lose customers and expand them. To estimate the acceptable cost of new SaaS revenue, we compare new revenue to operating loss and payback period. If you pay back the customer acquisition cost in 1.5 years and never lose them (100%+ NDR), you're doing well.

To evaluate payback period, we compared new revenue to net operating loss for the last 73 SaaS companies to IPO since October 2017. (55 out of 73). Here's the data. 1/(new revenue/operating loss) equals payback period. New revenue/operating loss equals cost of new revenue.

Payback averages a year. 55 SaaS companies that weren't profitable at IPO got a 1-year payback. Outstanding. If you pay for a customer in a year and never lose them (100%+ NDR), you're establishing a valuable business. The average was 1.3 years, which is within the 1.5-year range.

New revenue costs $0.96 on average. These SaaS companies lost $0.96 every $1 of new revenue last year. Again, impressive. Average new revenue per operating loss was $1.59.

Loss-in-operations definition. Operating loss revenue COGS S&M R&D G&A (technical point: be sure to use the absolute value of operating loss). It's wrong to only consider S&M costs and ignore other business costs. Operating loss and new revenue are measured over one year to eliminate seasonality.

Operating losses are desirable if you never lose a customer and have a quick payback period, especially when SaaS enterprises are valued on ARR. The payback period should be under 1.5 years, the cost of new income < $1, and net dollar retention 100%.

New ventures are exciting. It's fun to imagine yourself rich, successful, and famous (if that's your thing). How you'll help others and make your family proud. This excitement can pull you forward for years, even when you intuitively realize that the path you're on may not lead to your desired success.

Know when to change course. Switching course can mean pivoting or changing direction.

In this not-so-short blog, I'll describe the journey of building your dream. And how the journey might look when you think you're building your dream, but fall short of that vision. Both can feel similar in the beginning, but there are subtle differences.

Let’s dive in.

How an exciting journey to a dead end looks and feels.

You want to help many people. You're business-minded, creative, and ambitious. You jump into entrepreneurship. You're excited, free, and in control.

I'll use tech as an example because that's what I know best, but this applies to any entrepreneurial endeavor.

So you start learning the basics of your field, say coding/software development. You read books, take courses, and may even join a bootcamp. You start practicing, and the journey begins. Once you reach a certain level of skill (which can take months, usually 12-24), you gain the confidence to speak with others in the field and find common ground. You might attract a co-founder this way with time. You and this person embark on a journey (Tip: the idea you start with is rarely the idea you end with).

Amateur mistake #1: You spend months building a product before speaking to customers.

Building something pulls you forward blindly. You make mistakes, avoid customers, and build with your co-founder or small team in the dark for months, usually 6-12 months.

You're excited when the product launches. We'll be billionaires! The market won't believe it. This excites you and the team. Launch.

….

Nothing happens.

Some people may sign up out of pity, only to never use the product or service again.

You and the team are confused, discouraged and in denial. They don't get what we've built yet. We need to market it better, we need to talk to more investors, someone will understand our vision.

This is a hopeless path, and your denial could last another 6 months. If you're lucky, while talking to consumers and investors (which you should have done from the start), someone who has been there before would pity you and give you an idea to pivot into that can create income.

Suppose you get this idea and pivot your business. Again, you've just pivoted into something limited by what you've already built. It may be a revenue-generating idea, but it's rarely new. Now you're playing catch-up, doing something others are doing but you can do better. (Tip #2: Don't be late.) Your chances of winning are slim, and you'll likely never catch up.

You're finally seeing revenue and feel successful. You can compete, but if you're not a first mover, you won't earn enough over time. You'll get by or work harder than ever to earn what a skilled trade could provide. You didn't go into business to stress out and make $100,000 or $200,000 a year. When you can make the same amount by becoming a great software developer, electrician, etc.

You become stuck. Either your firm continues this way for years until you realize there isn't enough growth to recruit a strong team and remove yourself from day-to-day operations due to competition. Or a catastrophic economic event forces you to admit that what you were building wasn't new and unique and wouldn't get you where you wanted to be.

This realization could take 6-10 years. No kidding.

The good news is, you’ve learned a lot along the way and this information can be used towards your next venture (if you have the energy).

Key Lesson: Don’t build something if you aren’t one of the first in the space building it just for the sake of building something.

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Let's discuss what it's like to build something that can make your dream come true.

Case 2: Building something the market loves is difficult but rewarding.

It starts with a problem that hasn't been adequately solved for a long time but is now solvable due to technology. Or a new problem due to a change in how things are done.

Let's examine each example.

Example #1: Mass communication. The problem is now solvable due to some technological breakthrough.

Twitter — One of the first web 2 companies that became successful with the rise of smart mobile computing.

People can share their real-time activities via mobile device with friends, family, and strangers. Web 2 and smartphones made it easy and fun.

Example #2: A new problem has emerged due to some change in the way things are conducted.

Zoom- A web-conferencing company that reached massive success due to the movement towards “work from home”, remote/hybrid work forces.

Online web conferencing allows for face-to-face communication.

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These two examples show how to build a unicorn-type company. It's a mix of solving the right problem at the right time, either through a technological breakthrough that opens up new opportunities or by fundamentally changing how people do things.

Let's find these opportunities.

Start by examining problems, such as how the world has changed and how we can help it adapt. It can also be both. Start team brainstorming. Research technologies, current world-trends, use common sense, and make a list. Then, choose the top 3 that you're most excited about and seem most workable based on your skillsets, values, and passion.

Once you have this list, create the simplest MVP you can and test it with customers. The prototype can be as simple as a picture or diagram of user flow and end-user value. No coding required. Market-test. Twitter's version 1 was simple. It was a web form that asked, "What are you doing?" Then publish it from your phone. A global status update, wherever you are. Currently, this company has a $50 billion market cap.

Here's their MVP screenshot.

Small things grow. Tiny. Simplify.

Remember Frequency and Value when brainstorming. Your product is high frequency (Twitter, Instagram, Snapchat, TikTok) or high value (Airbnb for renting travel accommodations), or both (Gmail).

Once you've identified product ideas that meet the above criteria, they're simple, have a high frequency of use, or provide deep value. You then bring it to market in the simplest, most cost-effective way. You can sell a half-working prototype with imagination and sales skills. You need just enough of a prototype to convey your vision to a user or customer.

With this, you can approach real people. This will do one of three things: give you a green light to continue on your vision as is, show you that there is no opportunity and people won't use it, or point you in a direction that is a blend of what you've come up with and what the customer / user really wants, and you update the prototype and go back to the maze. Repeat until you have enough yeses and conviction to build an MVP.

What does Ukraine's murderous craziness mean?

Vladimir Putin expressed his patience to Israeli Prime Minister Naftali Bennet. Thousands, even hundreds of thousands of young and middle-aged males in his country have no meaning to him.

During a meeting in March with Prime Minister Naftali Bennett of Israel, Mr. Putin admitted that the Ukrainians were tougher “than I was told,” according to two people familiar with the exchange. “This will probably be much more difficult than we thought. But the war is on their territory, not ours. We are a big country and we have patience (The Inside Story of a Catastrophe).”

Putin should explain to Russian mothers how patient he is with his invasion of Ukraine.

Putin is rich. Even while sanctions have certainly limited Putin's access to his fortune, he has access to everything in Russia. Unlimited wealth.

The Russian leader's infrastructure was designed with his whims in mind. Vladimir Putin is one of the wealthiest and most catered-to people alive. He's also all-powerful, as his lack of opposition shows. His incredible wealth and power have isolated him from average people so much that he doesn't mind turning lives upside down to prove a point.

For many, losing a Russian spouse or son is painful. Whether the soldier was a big breadwinner or unemployed, the loss of a male figure leaves many families bewildered and anxious. Putin, Russia's revered president, seems unfazed.

People who know Mr. Putin say he is ready to sacrifice untold lives and treasure for as long as it takes, and in a rare face-to-face meeting with the Americans last month the Russians wanted to deliver a stark message to President Biden: No matter how many Russian soldiers are killed or wounded on the battlefield, Russia will not give up (The Inside Story of a Catastrophe).

Imagine a country's leader publicly admitting a mistake he's made. Imagine getting Putin's undivided attention.

So, I underestimated Ukrainians. I can't allow them make me appear terrible, so I'll utilize as many drunken dopes as possible to cover up my error. They'll die fulfilled and heroic.

Russia's human resources are limited, but its willingness to cause suffering is not. How many Russian families must die before the curse is broken? If mass protests started tomorrow, Russia's authorities couldn't stop them.

When Moscovites faced down tanks in August 1991, the Gorbachev coup ended in three days. Even though few city residents showed up, everything collapsed. This wicked disaster won't require many Russians.

One NATO member is warning allies that Mr. Putin is ready to accept the deaths or injuries of as many as 300,000 Russian troops — roughly three times his estimated losses so far.

If 100,000 Russians have died in Ukraine and Putin doesn't mind another 200,000 dying, why don't these 200,000 ghosts stand up and save themselves? Putin plays the role of concerned and benevolent leader effectively, but things aren't going well for Russia.

What would 300,000 or more missing men signify for Russia's future? How many kids will have broken homes? How many families won't form, and what will the economy do?

Putin reportedly cared about his legacy. His place in Russian history Putin's invasion of Ukraine settled his legacy. He has single-handedly weakened and despaired Russia since the 1980s.

Putin will be viewed by sensible people as one of Russia's worst adversaries, but Russians will think he was fantastic despite Ukraine.

The more setbacks Mr. Putin endures on the battlefield, the more fears grow over how far he is willing to go. He has killed tens of thousands in Ukraine, leveled cities, and targeted civilians for maximum pain — obliterating hospitals, schools, and apartment buildings while cutting off power and water to millions before winter. Each time Ukrainian forces score a major blow against Russia, the bombing of their country intensifies. And Mr. Putin has repeatedly reminded the world that he can use anything at his disposal, including nuclear arms, to pursue his notion of victory.

How much death and damage will there be in Ukraine if Putin sends 200,000 more Russians to the front? It's scary, sad, and sick.

Monster.

Genius or lucky?

From the title, you might think I'm selling advertising for a financial influencer, a dubious trading site, or a training organization to attract clients. I'm suspicious. Better safe than sorry.

But not here.

Jake Freeman, 20, made $110 million in a month, according to the Financial Times. At 18, he ran for president. He made his name in markets, not politics. Two years later, he's Wall Street's prince. Interview requests flood the prodigy.

Jake Freeman bought 5 million Bed Bath & Beyond Group shares for $5.5 in July 2022 and sold them for $27 a month later. He thought the stock might double. Since speculation died down, he sold well. The stock fell 40.5% to 11 dollars on Friday, 19 August 2022. On August 22, 2022, it fell 16% to $9.

Smallholders have been buying the stock for weeks and will lose heavily if it falls further. Bed Bath & Beyond is the second most popular stock after Foot Locker, ahead of GameStop and Apple.

Jake Freeman earned $110 million thanks to a significant stock market flurry.

Online broker customers aren't the only ones with jitters. By June 2022, Ken Griffin's Citadel and Stephen Mandel's Lone Pine Capital held nearly a third of the company's capital. Did big managers sell before the stock plummeted?

Recent stock movements (derivatives) and rumors could prompt a SEC investigation.

Jake Freeman wrote to the board of directors after his investment to call for a turnaround, given the company's persistent problems and short sellers. The bathroom and kitchen products distribution group's stock soared in July 2022 due to renewed buying by private speculators, who made it one of their meme stocks with AMC and GameStop.

Second-quarter 2022 results and financial health worsened. He didn't celebrate his miraculous operation in a nightclub. He told a British newspaper, "I'm shocked." His parents dined in New York. He returned to Los Angeles to study math and economics.

Jake Freeman founded Freeman Capital Management with his savings and $25 million from family, friends, and acquaintances. They are the ones who are entitled to the $110 million he raised in one month. Will his investors pocket and withdraw all or part of their profits or will they trust the young prodigy for new stunts on Wall Street?

His operation should attract new clients. Well-known hedge funds may hire him.

Jake Freeman didn't listen to gurus or former traders. At 17, he interned at a quantitative finance and derivatives hedge fund, Volaris. At 13, he began investing with his pharmaceutical executive uncle. All countries have increased their Google searches for the young trader in the last week.

Naturally, his success has inspired resentment.

His success stirs jealousy, and he's attacked on social media. On Reddit, people who lost money on Bed Bath & Beyond, Jake Freeman's fortune, are mourning.

Several conspiracy theories circulate about him, including that he doesn't exist or is working for a Taiwanese amusement park.

If all 20 million American students had the same trading skills, they would have generated $1.46 trillion. Jake Freeman is unique. Apprentice traders' careers are often short, disillusioning, and tragic.

Two years ago, 20-year-old Robinhood client Alexander Kearns committed suicide after losing $750,000 trading options. Great traders start young. Michael Platt of BlueCrest invested in British stocks at age 12 under his grandmother's supervision and made a £30,000 fortune. Paul Tudor Jones started trading before he turned 18 with his uncle. Warren Buffett, at age 10, was discussing investments with Goldman Sachs' head. Oracle of Omaha tells all.