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.

Price Intelligently put out amazing content on pricing your SaaS product. This blog's link to the whole report is worth reading. Our key takeaways are below.

Don't base prices on the competition. Competitor-based pricing has clear drawbacks. Their pricing approach is yours. Your company offers customers something unique. Otherwise, you wouldn't create it. This strategy is static, therefore you can't add value by raising prices without outpricing competitors. Look, but don't touch is the competitor-based moral. You want to know your competitors' prices so you're in the same ballpark, but they shouldn't guide your selections. Competitor-based pricing also drives down prices.

Value-based pricing wins. This is customer-based pricing. Value-based pricing looks outward, not inward or laterally at competitors. Your clients are the best source of pricing information. By valuing customer comments, you're focusing on buyers. They'll decide if your pricing and packaging are right. In addition to asking consumers about cost savings or revenue increases, look at data like number of users, usage per user, etc.

Value-based pricing increases prices. As you learn more about the client and your worth, you'll know when and how much to boost rates. Every 6 months, examine pricing.

Cloning top customers. You clone your consumers by learning as much as you can about them and then reaching out to comparable people or organizations. You can't accomplish this without knowing your customers. Segmenting and reproducing them requires as much detail as feasible. Offer pricing plans and feature packages for 4 personas. The top plan should state Contact Us. Your highest-value customers want more advice and support.

Question your 4 personas. What's the one item you can't live without? Which integrations matter most? Do you do analytics? Is support important or does your company self-solve? What's too cheap? What's too expensive?

Not everyone likes per-user pricing. SaaS organizations often default to per-user analytics. About 80% of companies utilizing per-user pricing should use an alternative value metric because their goods don't give more value with more users, so charging for them doesn't make sense.

At least 3:1 LTV/CAC. Break even on the customer within 2 years, and LTV to CAC is greater than 3:1. Because customer acquisition costs are paid upfront but SaaS revenues accrue over time, SaaS companies face an early financial shortfall while paying back the CAC.

ROI should be >20:1. Indeed. Ensure the customer's ROI is 20x the product's cost. Microsoft Office costs $80 a year, but consumers would pay much more to maintain it.

A/B Testing. A/B testing is guessing. When your pricing page varies based on assumptions, you'll upset customers. You don't have enough customers anyway. A/B testing optimizes landing pages, design decisions, and other site features when you know the problem but not pricing.

Don't discount. It cheapens the product, makes it permanent, and increases churn. By discounting, you're ruining your pricing analysis.

The holy grail of plain text task management is finally within reach

Plain text task management? Are you serious?? Dedicated task managers exist for a reason, you know. Sheesh.

—Oh, I know. Believe me, I know! But hear me out.

I've managed projects and tasks in plain text for more than four years. Since reorganizing my to-do list, plain text task management is within reach.

Data completely yours? One billion percent. Beef it up with coding? Be my guest.

Enter: The List

The answer? A list. That’s it!

Write down tasks. Obsidian, Notenik, Drafts, or iA Writer are good plain text note-taking apps.

List too long? Of course, it is! A large list tells you what to do. Feel the itch and friction. Then fix it.

• But I want to be able to distinguish between work and personal life! List two things.

• However, I need to know what should be completed first. Put those items at the top.

• However, some things keep coming up, and I need to be reminded of them! Put those in your calendar and make an alarm for them.

• But since individual X hasn't completed task Y, I can't proceed with this. Create a Waiting section on your list by dividing it.

• But I must know what I'm supposed to be doing right now! Read your list(s). Check your calendar. Think critically.

Before I begin a new one, I remind myself that "Listory Never Repeats."

There’s no such thing as too many lists if all are needed. There is such a thing as too many lists if you make them before they’re needed. Before they complain that their previous room was small or too crowded or needed a new light.

A list that feels too long has a voice; it’s telling you what to do next.

I use one Master List. It's a control panel that tells me what to focus on short-term. If something doesn't need semi-immediate attention, it goes on my Backlog list.

Todd Lewandowski's DWTS (Done, Waiting, Top 3, Soon) performance deserves praise. His DWTS to-do list structure has transformed my plain-text task management. I didn't realize it was upside down.

This is my take on it:

D = Done

Move finished items here. If they pile up, clear them out every week or month. I have a Done Archive folder.

W = Waiting

Things seething in the background, awaiting action. Stir them occasionally so they don't burn.

T = Top 3

Three priorities. Personal comes first, then work. There will always be a top 3 (no more than 5) in every category. Projects, not chores, usually.

S = Soon

This part is action-oriented. It's for anything you can accomplish to finish one of the Top 3. This collection includes thoughts and project lists. The sole requirement is that they should be short-term goals.

Some of you have probably concluded this isn't for you. Please read Todd's piece before throwing out the baby. Often. You shouldn't miss a newborn.

As much as Dancing With The Stars helps me recall this method, I may try switching their order. TSWD; Drilling Tunnel Seismic? Serenity After Task?

Master List Showcase

My Master List lives alone in its own file, but sometimes appears in other places.  It's included in my Weekly List template. Here's a (soon-to-be-updated) demo vault of my Obsidian planning setup to download for free.

Here's the code behind my weekly screenshot:

## [[Master List - 2022|✓]]  TO DO

![[Master List - 2022]]

FYI, I use the Minimal Theme in Obsidian, with a few tweaks.

You may note I'm utilizing a checkmark as a link. For me, that's easier than locating the proper spot to click on the embed.

Blue headings for Done and Waiting are links. Done links to the Done Archive page and Waiting to a general waiting page.

Read my full article here.

WTF is wrong with you people?

When I was laid off as editor of my town's daily newspaper, I went silent on social media. I knew it was coming and had been quietly removing personal items each day, but the pain was intense.

I posted a day later. I didn't bad-mouth GateHouse Media but expressed my sadness at leaving the newspaper industry, pride in my accomplishments, and hope for success in another industry.

Normal job-loss response.

What do you recognize as abnormal?

The bullshit I’ve been reading from laid-off folks on LinkedIn.

If you're there, you know. Many Twitter or Facebook/Meta employees recently lost their jobs.

Well, many of them did not “lose their job,” actually. They were “impacted by the layoffs” at their former employer. I keep seeing that phrase.

Why don’t they want to actually say it? Why the euphemism?

Many are excited about the opportunities ahead. The jobless deny being sad.

They're ecstatic! They have big plans.

Hope so. Sincerely! Being laid off stinks, especially if, like me, your skills are obsolete. It's worse if, like me, you're too old to start a new career. Ageism exists despite denials.

Nowadays, professionalism seems to demand psychotic levels of fake optimism.

Why? Life is unpredictable. That's indisputable. You shouldn't constantly complain or cry in public, but you also shouldn't pretend everything's great.

It makes you look psychotic, not positive. It's like saying at work:

“I was impacted by the death of my spouse of 20 years this week, and many of you have reached out to me, expressing your sympathy. However, I’m choosing to remember the amazing things we shared. I feel confident that there is another marriage out there for me, and after taking a quiet weekend trip to reset myself, I’ll be out there looking for the next great marital adventure! #staypositive #available #opentolove

Also:

“Now looking for our next #dreamhome after our entire neighborhood was demolished by a wildfire last night. We feel so lucky to have lived near so many amazing and inspirational neighbors, all of whom we will miss as we go on our next housing adventure. The best house for us is yet to come! If you have a great neighborhood you’d recommend, please feel free to reach out and touch base with us! #newhouse #newneighborhood #newlife

Admit it. That’s creepy.

The constant optimism makes me feel sick to my stomach.

Viscerally.

I hate fakes.

Imagine a fake wood grain desk. Wouldn't it be better if the designer accepted that it's plastic and went with that?

Real is better but not always nice. When something isn't nice, you don't have to go into detail, but you also shouldn't pretend it's great.

How to announce your job loss to the world.

Do not pretend to be happy, but don't cry and drink vodka all afternoon.

Say you loved your job, and that you're looking for new opportunities.

Yes, if you'll miss your coworkers. Otherwise, don't badmouth. No bridge-burning!

Please specify the job you want. You may want to pivot.

Alternatively, try this.

You could always flame out.

If you've pushed yourself too far into toxic positivity, you may be ready to burn it all down. If so, make it worthwhile by writing something like this:

Well, I was shitcanned by the losers at #Acme today. That bitch Linda in HR threw me under the bus just because she saw that one of my “friends” tagged me in some beach pics on social media after I called in sick with Covid. The good thing is I will no longer have to watch my ass around that #asspincher Ron in accounting, but I’m sad that I will no longer have a cushy job with high pay or access to the primo office supplies I’ve been sneaking home for the last five years. (Those gel pens were the best!) I am going to be taking some time off to enjoy my unemployment and hammer down shots of Jägermeister but in about five months I’ll be looking for anything easy with high pay and great benefits. Reach out if you can help! #officesupplies #unemploymentrocks #drinkinglikeagirlboss #acmesucks

It beats the fake positivity.

New social media producers' biggest error

The Treadmill of Social Media Content

New creators focus on the wrong platforms.

They post to Instagram, Twitter, TikTok, etc.

They create daily material, but it's never enough for social media algorithms.

Creators recognize they're on a content creation treadmill.

They have to keep publishing content daily just to stay on the algorithm’s good side and avoid losing the audience they’ve built on the platform.

This is exhausting and unsustainable, causing creator burnout.

They focus on short-lived platforms, which is an issue.

Comparing low- and high-return social media platforms

Social media networks are great for reaching new audiences.

Their algorithm is meant to viralize material.

Social media can use you for their aims if you're not careful.

To master social media, focus on the right platforms.

To do this, we must differentiate low-ROI and high-ROI platforms:

Low ROI platforms are ones where content has a short lifespan. High ROI platforms are ones where content has a longer lifespan.

A tweet may be shown for 12 days. If you write an article or blog post, it could get visitors for 23 years.

ROI is drastically different.

New creators have limited time and high learning curves.

Nothing is possible.

First create content for high-return platforms.

ROI for social media platforms

Here are high-return platforms:

1. Your Blog - A single blog article can rank and attract a ton of targeted traffic for a very long time thanks to the power of SEO.

2. YouTube - YouTube has a reputation for showing search results or sidebar recommendations for videos uploaded 23 years ago. A superb video you make may receive views for a number of years.

3. Medium - A platform dedicated to excellent writing is called Medium. When you write an article about a subject that never goes out of style, you're building a digital asset that can drive visitors indefinitely.

These high ROI platforms let you generate content once and get visitors for years.

This contrasts with low ROI platforms:

1. Twitter

2. Instagram

3. TikTok

4. LinkedIn

5. Facebook

The posts you publish on these networks have a 23-day lifetime. Instagram Reels and TikToks are exceptions since viral content can last months.

If you want to make content creation sustainable and enjoyable, you must focus the majority of your efforts on creating high ROI content first. You can then use the magic of repurposing content to publish content to the lower ROI platforms to increase your reach and exposure.

How To Use Your Content Again

So, you’ve decided to focus on the high ROI platforms.

Great!

You've published an article or a YouTube video.

You worked hard on it.

Now you have fresh stuff.

What now?

If you are not repurposing each piece of content for multiple platforms, you are throwing away your time and efforts.

You've created fantastic material, so why not distribute it across platforms?

Repurposing Content Step-by-Step

For me, it's writing a blog article, but you might start with a video or podcast.

The premise is the same regardless of the medium.

Start by creating content for a high ROI platform (YouTube, Blog Post, Medium). Then, repurpose, edit, and repost it to the lower ROI platforms.

Here's how to repurpose pillar material for other platforms:

1. Post the article on your blog.

2. Put your piece on Medium (use the canonical link to point to your blog as the source for SEO)

3. Create a video and upload it to YouTube using the talking points from the article.

4. Rewrite the piece a little, then post it to LinkedIn.

5. Change the article's format to a Thread and share it on Twitter.

6. Find a few quick quotes throughout the article, then use them in tweets or Instagram quote posts.

7. Create a carousel for Instagram and LinkedIn using screenshots from the Twitter Thread.

8. Go through your film and select a few valuable 30-second segments. Share them on LinkedIn, Facebook, Twitter, TikTok, YouTube Shorts, and Instagram Reels.

9. Your video's audio can be taken out and uploaded as a podcast episode.

If you (or your team) achieve all this, you'll have 20-30 pieces of social media content.

If you're just starting, I wouldn't advocate doing all of this at once.

Instead, focus on a few platforms with this method.

You can outsource this as your company expands. (If you'd want to learn more about content repurposing, contact me.)

You may focus on relevant work while someone else grows your social media on autopilot.

You develop high-ROI pillar content, and it's automatically chopped up and posted on social media.

This lets you use social media algorithms without getting sucked in.

Thanks for reading!