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.

After 10 years of working in scale-ups, I've embraced a few concepts for scaling Tech and Product teams.

First, cross-functionalize teams. Product Managers represent the business, Product Designers the consumer, and Engineers build.

I organize teams of 5-10 individuals, following AWS's two pizza teams guidelines, with a Product Trio guiding each.

If more individuals are needed to reach a goal, I group teams under a Product Trio.

With Engineering being the biggest group, Staff/Principal Engineers often support the Trio on cross-team technical decisions.

Product Managers, Engineering Managers, or Engineers in the team may manage projects (depending on the project or aim), but the trio is collectively responsible for the team's output and outcome.

Once the Product Trio model is created, roles, duties, team ceremonies, and cooperation models must be clarified.

Keep reporting lines by discipline. Line managers are accountable for each individual's advancement, thus it's crucial that they know the work in detail.

Cross-team collaboration becomes more important after 3 teams (15-30 people). Teams can easily diverge in how they write code, run ceremonies, and build products.

Establishing groups of people that are cross-team, but grouped by discipline and skills, sharing and agreeing on working practices becomes critical.

The “Spotify Guild” model has been where I’ve taken a lot of my inspiration from.

Last, establish a taxonomy for communication channels.

In Slack, I create one channel per team and one per guild (and one for me to have discussions with the team leads).

These are just some of the basic principles I follow to organize teams.

A book I particularly like about team types and how they interact with each other is https://teamtopologies.com/.

Dharmesh Shah co-founded HubSpot. WordPlay reached $90,000 per month in revenue without utilizing any of his wealth.

His method:

Take Advantage Of An Established Trend

Remember Wordle? Dharmesh was instantly hooked. As was the tech world.

HubSpot's co-founder noted inefficiencies in a recent My First Million episode. He wanted to play daily. Dharmesh, a tinkerer and software engineer, decided to design a word game.

He's a billionaire. How could he?

1. Wordle had limitations in his opinion;

2. Dharmesh is fundamentally a developer. He desired to start something new and increase his programming knowledge;

3. This project may serve as an excellent illustration for his son, who had begun learning about software development.

Better It Up

Building a new Wordle wasn't successful.

WordPlay lets you play with friends and family. You could challenge them and compare the results. It is a built-in growth tool.

WordPlay features:

• the capacity to follow sophisticated statistics after creating an account;

• continuous feedback on your performance;

• Outstanding domain name (wordplay.com).

Project Development

WordPlay has 9.5 million visitors and 45 million games played since February.

HubSpot co-founder credits tremendous growth to flywheel marketing, pushing the game through his own following.

Choosing an exploding specialty and making sharing easy also helped.

Shah enabled Google Ads on the website to test earning potential. Monthly revenue was $90,000.

That's just Google Ads. If monetization was the goal, a specialized ad network like Ezoic could double or triple the amount.

Wordle was a great buy for The New York Times at $1 million.

Without self-control, you'll waste time chasing dopamine fixes.

I found a powerful quote in Tony Robbins' Awaken The Giant Within:

“Most of the challenges that we have in our personal lives come from a short-term focus” — Tony Robbins

Most people are short-term oriented, but highly successful people are long-term oriented.

Successful people act in line with their long-term goals and values, while the rest are distracted by short-term pleasures and dopamine fixes.

Instant gratification wrecks lives

Instant pleasure is fleeting. Quickly fading effects leave you craving more stimulation.

Before you know it, you're in a cycle of quick fixes. This explains binging on food, social media, and Netflix.

These things cause a dopamine spike, which is entertaining. This dopamine spike crashes quickly, leaving you craving more stimulation.

It's fine to watch TV or play video games occasionally. Problems arise when brain impulses aren't controlled. You waste hours chasing dopamine fixes.

Instant gratification becomes problematic when it interferes with long-term goals, happiness, and life fulfillment.

Most rewarding things require delay

Life's greatest rewards require patience and delayed gratification. They must be earned through patience, consistency, and effort.

Ex:

• A fit, healthy body

• A deep connection with your spouse

• A thriving career/business

• A healthy financial situation

These are some of life's most rewarding things, but they take work and patience. They all require the ability to delay gratification.

To have a healthy bank account, you must save (and invest) a large portion of your monthly income. This means no new tech or clothes.

If you want a fit, healthy body, you must eat better and exercise three times a week. So no fast food and Netflix.

It's a battle between what you want now and what you want most.

Successful people choose what they want most over what they want now. It's a major difference.

Instant vs. delayed gratification

Most people subconsciously prefer instant rewards over future rewards, even if the future rewards are more significant.

We humans aren't logical. Emotions and instincts drive us. So we act against our goals and values.

Fortunately, instant gratification bias can be overridden. This is a modern superpower. Effective methods include:

#1: Train your brain to handle overstimulation

Training your brain to function without constant stimulation is a powerful change. Boredom can lead to long-term rewards.

Unlike impulsive shopping, saving money is boring. Having lots of cash is amazing.

Compared to video games, deep work is boring. A successful online business is rewarding.

Reading books is boring compared to scrolling through funny videos on social media. Knowledge is invaluable.

You can't do these things if your brain is overstimulated. Your impulses will control you. To reduce overstimulation addiction, try:

• Daily meditation (10 minutes is enough)

• Daily study/work for 90 minutes (no distractions allowed)

• First hour of the day without phone, social media, and Netflix

• Nature walks, journaling, reading, sports, etc.

#2: Make Important Activities Less Intimidating

Instant gratification helps us cope with stress. Starting a book or business can be intimidating. Video games and social media offer a quick escape in such situations.

Make intimidating tasks less so. Break them down into small tasks. Start a new business/side-hustle by:

• Get domain name

• Design website

• Write out a business plan

• Research competition/peers

• Approach first potential client

Instead of one big mountain, divide it into smaller sub-tasks. This makes a task easier and less intimidating.

#3: Plan ahead for important activities

Distractions will invade unplanned time. Your time is dictated by your impulses, which are usually Netflix, social media, fast food, and video games. It wants quick rewards and dopamine fixes.

Plan your days and be proactive with your time. Studies show that scheduling activities makes you 3x more likely to do them.

To achieve big goals, you must plan. Don't gamble.

Want to get fit? Schedule next week's workouts. Want a side-job? Schedule your work time.

Every week I meet many people interested in VC. Many of them ask me what it's like to be a junior analyst in VC or what I've learned so far.

Looking back, I've learned many things as a junior VC, having gone through an almost-euphoric peak bull market, failed tech IPOs of 2019 including WeWorks' catastrophic fall, and the beginnings of a bearish market.

1. Network, network, network!

VCs spend 80% of their time networking. Junior VCs source deals or manage portfolios. You spend your time bringing startups to your fund or helping existing portfolio companies grow. Knowing stakeholders (corporations, star talent, investors) in your particular areas of investment helps you develop your portfolio.

Networking was one of my strengths. When I first started in the industry, I'd go to startup events and meet 50 people a month. Over time, I realized these relationships were shallow and I was only getting business cards. So I stopped seeing networking as a transaction. VC is a long-term game, so you should work with people you like. Now I know who I click with and can build deeper relationships with them. My network is smaller but more valuable than before.

2. The Most Important Metric Is Founder

People often ask how we pick investments. Why some companies can raise money and others can't is a mystery. The founder is the most important metric for VCs. When a company is young, the product, environment, and team all change, but the founder remains constant. VCs bet on the founder, not the company.

How do we decide which founders are best after 2-3 calls? When looking at a founder's profile, ask why this person can solve this problem. The founders' track record will tell. If the founder is a serial entrepreneur, you know he/she possesses the entrepreneur DNA and will likely succeed again. If it's his/her first startup, focus on industry knowledge to deliver the best solution.

3. A company's fate can be determined by macrotrends.

Macro trends are crucial. A company can have the perfect product, founder, and team, but if it's solving the wrong problem, it won't succeed. I've also seen average companies ride the wave to success. When you're on the right side of a trend, there's so much demand that more companies can get a piece of the pie.

In COVID-19, macro trends made or broke a company. Ed-tech and health-tech companies gained unicorn status and raised funding at inflated valuations due to sudden demand. With the easing of pandemic restrictions and the start of a bear market, many of these companies' valuations are in question.

4. Look for methods to ACTUALLY add value.

You only need to go on VC twitter (read: @vcstartterkit and @vcbrags) for 5 minutes or look at fin-meme accounts on Instagram to see how much VCs claim to add value but how little they actually do. VC is a long-term game, though. Long-term, founders won't work with you if you don't add value.

How can we add value when we're young and have no network? Leaning on my strengths helped me. Instead of viewing my age and limited experience as a disadvantage, I realized that I brought a unique perspective to the table.

As a VC, you invest in companies that will be big in 5-7 years, and millennials and Gen Z will have the most purchasing power. Because you can relate to that market, you can offer insights that most Partners at 40 can't. I added value by helping with hiring because I had direct access to university talent pools and by finding university students for product beta testing.

5. Develop your personal brand.

Generalists or specialists run most funds. This means that funds either invest across industries or have a specific mandate. Most funds are becoming specialists, I've noticed. Top-tier founders don't lack capital, so funds must find other ways to attract them. Why would a founder work with a generalist fund when a specialist can offer better industry connections and partnership opportunities?

Same for fund members. Founders want quality investors. Become a thought leader in your industry to meet founders. Create content and share your thoughts on industry-related social media. When I first started building my brand, I found it helpful to interview industry veterans to create better content than I could on my own. Over time, my content attracted quality founders so I didn't have to look for them.

These are my biggest VC lessons. This list isn't exhaustive, but it's my industry survival guide.

Apple's latest revelation may shock iPod fans and former owners.

Apple discontinued the iPod touch on May 11, 2022. After 21 years, Apple killed the last surviving iPod, a device Steve Jobs believed would revolutionize the music industry.

Jobs was used to making bold predictions, but few expected Apple's digital music player to change the music industry. It did.

This chaos created new business opportunities. Spotify, YouTube, and Amazon are products of that chaotic era.

As the digital landscape changes, so do consumers, and the iPod has lost favor. I'm sure Apple realizes the importance of removing an icon. The iPod was Apple like the Mac and iPhone. I think it's bold to retire such a key Apple cornerstone. What would Jobs do?

iPod evolution across the ages

Here's an iPod family tree for all you enthusiasts.

iPod vintage (Oct 2001 to Sep 2014, 6 generations)

The original iPod had six significant upgrades since 2001. Apple announced an 80 GB ($249) and 160 GB ($349) iPod classic in 2007.

Apple updated the 80 GB model with a 120 GB device in September 2008. Apple upgraded the 120 GB model with a 160 GB variant a year later (2009). This was the last iteration, and Apple discontinued the classic in September 2014.

iPod nano (Jan 2004 to Sep 2005, 2 generations)

Apple debuted a smaller, brightly-colored iPod in 2004. The first model featured 4 GB, enough for 1,000 songs.

Apple produced a new 4 GB or 6 GB iPod mini in February 2005 and discontinued it in September when they released a better-looking iPod nano.

iTouch nano (Sep 2005 to July 2017, 7 generations)

I loved the iPod nano. It was tiny and elegant with enough tech to please most music aficionados, unless you carry around your complete music collection.

Apple owed much of the iPod nano's small form and success to solid-state flash memory. Flash memory doesn't need power because it has no moving parts. This makes the iPod nano more durable than the iPod classic and mini, which employ hard drives.

Apple manufactured seven generations of the iPod nano, improving its design, display screen, memory, battery, and software, but abandoned it in July 2017 due to dwindling demand.

Shuffle iPod (Jan 2005 to Jul 2017, 4 generations)

The iPod shuffle was entry-level. It was a simple, lightweight, tiny music player. The iPod shuffle was perfect for lengthy bike trips, runs, and hikes.

Apple sold 10 million iPod shuffles in the first year and kept making them for 12 years, through four significant modifications.

iOS device (Sep 2007 to May 2022, 7 generations)

The iPod touch's bigger touchscreen interface made it a curious addition to the iPod family. The iPod touch resembled an iPhone more than the other iPods, making them hard to tell apart.

Many were dissatisfied that Apple removed functionality from the iPod touch to avoid making it too similar to the iPhone. Seven design improvements over 15 years brought the iPod touch closer to the iPhone, but not completely.

The iPod touch uses the same iOS operating system as the iPhone, giving it access to many apps, including handheld games.

The iPod touch's long production run is due to the next generation of music-loving gamers.

What made the iPod cool

iPod revolutionized music listening. It was the first device to store and play MP3 music, allowing you to carry over 1,000 songs anywhere.

The iPod changed consumer electronics with its scroll wheel and touchscreen. Jobs valued form and function equally. He showed people that a product must look good to inspire an emotional response and ignite passion.

The elegant, tiny iPod was a tremendous sensation when it arrived for $399 in October 2001. Even at this price, it became a must-have for teens to CEOs.

It's hard to identify any technology that changed how music was downloaded and played like the iPod. Apple iPod and iTunes had 63% of the paid music download market in the fourth quarter of 2012.

The demise of the iPod was inevitable

Apple discontinuing the iPod touch after 21 years is sad. This ends a 00s music icon.

Jobs was a genius at anticipating market needs and opportunities, and Apple launched the iPod at the correct time.

Few consumer electronics items have had such a lasting impact on music lovers and the music industry as the iPod.

Smartphones and social media have contributed to the iPod's decline. Instead of moving to the music, the new generation of consumers is focused on social media. They're no longer passive content consumers; they're active content creators seeking likes and followers. Here, the smartphone has replaced the iPod.

It's hard not to feel a feeling of loss, another part of my adolescence now forgotten by the following generation.

So, if you’re lucky enough to have a working iPod, hang on to that relic and enjoy the music and the nostalgia.