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.

One-hour ebook sales, affiliate relationships, and more.

If you follow me, you may know I started a new ebook in August 2022.

Despite publishing on this platform, my website, and Quora, I'm not a writer.

My writing speed is slow, 2,000 words a day, and I struggle to communicate cohesively.

In April 2022, I wrote a successful guide on How to Write Google-Friendly Blog Posts.

I had no email list or social media presence. I've made $1,600+ selling ebooks.

Evidence:

My first digital offering isn't a book.

It's an actionable guide with my tried-and-true process for writing Google-friendly content.

I'm not bragging.

Established authors like Tim Denning make more from my ebook sales with one newsletter.

This experience taught me writing isn't a privilege.

Writing a book and making money online doesn't require expertise.

Many don't consult experts. They want someone approachable.

Two years passed before I realized my own limits.

I have a brain, two hands, and Internet to spread my message.

I wrote and published a second ebook after the first's success.

On Gumroad, I released my second digital product.

Here's my complete Gumroad evaluation.

Gumroad is a marketplace for content providers to develop and sell sales pages.

Gumroad handles payments and client requests. It's helpful when someone sends a bogus payment receipt requesting an ebook (actual story!).

You'll forget administrative concerns after your first ebook sale.

After my first ebook sale, I did this: I made additional cash!

After every sale, I tell myself, "I built a new semi-passive revenue source."

This thinking shift helps me become less busy while increasing my income and quality of life.

Besides helping others, folks sell evergreen digital things to earn passive money.

It's in my second ebook.

I explain how I built and sold 50+ copies of my SEO writing ebook without being an influencer.

I show how anyone can sell ebooks on Gumroad and automate their sales process.

This is my ebook.

After publicizing the ebook release, I sold three copies within an hour.

Wow, or meh?

I don’t know.

The answer is different for everyone.

These three sales came from a small email list of 40 motivated fans waiting for my ebook release.

I had bigger plans.

I'll market my ebook on Medium, my website, Quora, and email.

I'm testing affiliate partnerships this time.

One of my ebook buyers is now promoting it for 40% commission.

Become my affiliate if you think your readers would like my ebook.

My ebook is a few days old, but I'm interested to see where it goes.

My SEO writing book started without an email list, affiliates, or 4,000 website visitors. I've made four figures.

I'm slowly expanding my communication avenues to have more impact.

Even a small project can open doors you never knew existed.

So began my writing career.

In summary

If you dare, every concept can become a profitable trip.

Before, I couldn't conceive of creating an ebook.

How to Sell eBooks on Gumroad is my second digital product.

Marketing and writing taught me that anything can be sold online.

If asked, run.

An entrepreneur asked me about her pitch deck. A Platform as a Service (PaaS).

She told me she hadn't done her 5-year forecasts but would soon.

I said, Don't bother. I added "time-wasting."

“I've been asked”, she said.

“Who asked?”

“a VC”

“5-year forecast?”

“Yes”

“Get another VC. If he asks, it's because he doesn't understand your solution or to waste your time.”

Some VCs are lagging. They're still using steam engines.

10-years ago, 5-year forecasts were requested.

Since then, we've adopted a 3-year plan.

But It's outdated.

Max one year.

What has happened?

Revolutionary technology. NO-CODE.

Revolution's consequences?

Product viability tests are shorter. Hugely. SaaS and PaaS.

Let me explain:

• Building a minimum viable product (MVP) that works only takes a few months.

• 1 to 2 months for practical testing.

• Your company plan can be validated or rejected in 4 months as a consequence.

After validation, you can ask for VC money. Even while a prototype can generate revenue, you may not require any.

Good VCs won't ask for a 3-year business plan in that instance.

One-year, though.

If you want, establish a three-year plan, but realize that the second year will be different.

You may have changed your business model by then.

A VC isn't interested in a three-year business plan because your solution may change.

Your ability to create revenue will be key.

• But also, to pivot.

• They will be interested in your value proposition.

• They will want to know what differentiates you from other competitors and why people will buy your product over another.

• What will interest them is your resilience, your ability to bounce back.

• Not to mention your mindset. The fact that you won’t get discouraged at the slightest setback.

• The grit you have when facing adversity, as challenges will surely mark your journey.

• The authenticity of your approach. They’ll want to know that you’re not just in it for the money, let alone to show off.

• The fact that you put your guts into it and that you are passionate about it. Because entrepreneurship is a leap of faith, a leap into the void.

• They’ll want to make sure you are prepared for it because it’s not going to be a walk in the park.

• They’ll want to know your background and why you got into it.

• They’ll also want to know your family history.

• And what you’re like in real life.

So a 5-year plan…. You can bet they won’t give a damn. Like their first pair of shoes.

Yes, client meetings are difficult. Especially when I'm alone.

Clients must tell us their problems so we can help.

In-meeting challenges contribute nothing to our work. Consider this:

• Clients are unprepared.

• Clients are distracted.

• Clients are confused.

Introducing Jack Dorsey's Google Doc approach

I endorse his approach to meetings.

Not Google Doc-related. Jack uses it for meetings.

This is what his meetings look like.

• Prior to the meeting, the Chair creates the agenda, structure, and information using Google Doc.

• Participants in the meeting would have 5-10 minutes to read the Google Doc.

• They have 5-10 minutes to type their comments on the document.

• In-depth discussion begins

There is elegance in simplicity. Here's how Jack's approach is fantastic.

Unprepared clients are given time to read.

During the meeting, they think and work on it.

They can see real-time remarks from others.

Discussion ensues.

Three months ago, I fell for this strategy. After trying it with a client, I got good results.

I conducted social control experiments in a few client workshops.

Context matters.

I am sure Jack Dorsey’s method works well in meetings. What about client workshops?

So, I tested Enterprise of the Future with a consulting client.

I sent multiple emails to client stakeholders describing the new approach.

No PowerPoints that day. I spent the night setting up the Google Doc with conversation topics, critical thinking questions, and a Before and After section.

The client was shocked. First, a Google Doc was projected. Second surprise was a verbal feedback.

“No pre-meeting materials?”

“Don’t worry. I know you are not reading it before our meeting, anyway.”

We laughed. The experiment started.

Observations throughout a 90-minute engagement workshop from beginning to end

For 10 minutes, the workshop was silent.

People read the Google Doc. For some, the silence was unnerving.

“Are you not going to present anything to us?”

I said everything's in Google Doc. I asked them to read, remark, and add relevant paragraphs.

As they unlocked their laptops, they were annoyed.

Ten client stakeholders are typing on the Google Doc. My laptop displays comment bubbles, red lines, new paragraphs, and strikethroughs.

The first 10 minutes were productive. Everyone has seen and contributed to the document.

I was silent.

The move to a classical workshop was smooth. I didn't stimulate dialogue. They did.

Stephanie asked Joe why a blended workforce hinders company productivity. She questioned his comments and additional paragraphs.

That is when a light bulb hit my head. Yes, you want to speak to the right person to resolve issues!

Not only that was discussed. Others discussed their remark bubbles with neighbors. Debate circles sprung up one after the other.

The best part? I asked everyone to add their post-discussion thoughts on a Google Doc.

After the workshop, I have:

• An agreement-based working document

• A post-discussion minutes that are prepared for publication

• A record of the discussion points that were brought up, argued, and evaluated critically

It showed me how stakeholders viewed their Enterprise of the Future. It allowed me to align with them.

Finale Keynotes

Client meetings are a hit-or-miss. I know that.

Jack Dorsey's meeting strategy works for consulting. It promotes session alignment.

It relieves clients of preparation.

I get the necessary information to advance this consulting engagement.

It is brilliant.

This is how to build a car while driving.

Building a high-growth startup is compared to building a car while it's speeding down the highway.

How to plan without going crazy? Or, without losing team, board, and investor buy-in?

I just delivered our company's product roadmap for the rest of the year. Complete. Thorough. Page-long. I'm optimistic about its chances of surviving as everything around us changes, from internal priorities to the global economy.

It's tricky. This isn't the first time I've created a startup roadmap. I didn't invent a document. It took time to deliver a document that will be relevant for months.

Goals matter.

Although they never change, goals are rarely understood.

This is the third in a series about a startup's unique roadmapping needs. Velocity is the intensity at which a startup must produce to survive.

A high-growth startup moves at breakneck speed, which I alluded to when I said priorities and economic factors can change daily or weekly.

At that speed, a startup's roadmap must be flexible, bend but not break, and be brief and to the point. I can't tell you how many startups and large companies develop a product roadmap every quarter and then tuck it away.

Big, wealthy companies can do this. It's suicide for a startup.

The drawer thing happens because startup product roadmaps are often valid for a short time. The roadmap is a random list of features prioritized by different company factions and unrelated to company goals.

It's not because the goals changed that a roadmap is shelved or ignored. Because the company's goals were never communicated or documented in the context of its product.

In the previous post, I discussed how to turn company goals into a product roadmap. In this post, I'll show you how to make a one-page startup roadmap.

In a future post, I'll show you how to follow this roadmap. This roadmap helps you track company goals, something a roadmap must do.

Be vague for growth, but direct for execution.

Here's my plan. The real one has more entries and more content in each.

Let's discuss smaller boxes.

Product developers and engineers know that the further out they predict, the more wrong they'll be. When developing the product roadmap, this rule is ignored. Then it bites us three, six, or nine months later when we haven't even started.

Why do we put everything in a product roadmap like a project plan?

Yes, I know. We use it when the product roadmap isn't goal-based.

A goal-based roadmap begins with a document that outlines each goal's idea, execution, growth, and refinement.

Once the goals are broken down into epics, initiatives, projects, and programs, only the idea and execution phases should be modeled. Any goal growth or refinement items should be vague and loosely mapped.

Why? First, any idea or execution-phase goal will result in growth initiatives that are unimaginable today. Second, internal priorities and external factors will change, but the goals won't. Locking items into calendar slots reduces flexibility and forces deviation from the single source of truth.

No soothsayers. Predicting the future is pointless; just prepare.

A map is useless if you don't know where you're going.

As we speed down the road, the car and the road will change. Goals define the destination.

This quarter and next quarter's roadmap should be set. After that, you should track destination milestones, not how to get there.

When you do that, even the most critical investors will understand the roadmap and buy in. When you track progress at the end of the quarter and revise your roadmap, the destination won't change.