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.

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.

We're opening up Maki through a series of Medium posts. We'll describe what Maki is building and how. We'll explain how we built a SaaS in 100 days. This isn't a step-by-step guide to starting a business, but a product philosophy to help you build quickly.

Focus on end-users.

This may seem obvious, but it's important to talk to users first. When we started thinking about Maki, we interviewed 100 HR directors from SMBs, Next40 scale-ups, and major Enterprises to understand their concerns. We initially thought about the future of employment, but most of their worries centered on Recruitment. We don't have a clear recruiting process, it's time-consuming, we recruit clones, we don't support diversity, etc. And as hiring managers, we couldn't help but agree.

Co-create your product with your end-users.

We went to the drawing board, read as many books as possible (here, here, and here), and when we started getting a sense for a solution, we questioned 100 more operational HR specialists to corroborate the idea and get a feel for our potential answer. This confirmed our direction to help hire more objectively and efficiently.

Back to the drawing board, we designed our first flows and screens. We organized sessions with certain survey respondents to show them our early work and get comments. We got great input that helped us build Maki, and we met some consumers. Obsess about users and execute alongside them.

Don’t shoot for the moon, yet. Make pragmatic choices first.

Once we were convinced, we began building. To launch a SaaS in 100 days, we needed an operating principle that allowed us to accelerate while still providing a reliable, secure, scalable experience. We focused on adding value and outsourced everything else. Example:

Concentrate on adding value. Reuse existing bricks.

When determining which technology to use, we looked at our strengths and the future to see what would last. Node.js for backend, React for frontend, both with typescript. We thought this technique would scale well since it would attract more talent and the surrounding mature ecosystem would help us go quicker.

We explored for ways to bootstrap services while setting down strong foundations that might support millions of users. We built our backend services on NestJS so we could extend into microservices later. Hasura, a GraphQL APIs engine, automates Postgres data exposing through a graphQL layer. MUI's ready-to-use components powered our design-system. We used well-maintained open-source projects to speed up certain tasks.

We outsourced important components of our platform (Auth0 for authentication, Stripe for billing, SendGrid for notifications) because, let's face it, we couldn't do better. We choose to host our complete infrastructure (SQL, Cloud run, Logs, Monitoring) on GCP to simplify our work between numerous providers.

Focus on your business, use existing bricks for the rest. For the curious, we'll shortly publish articles detailing each stage.

Most importantly, empower people and step back.

We couldn't have done this without the incredible people who have supported us from the start. Since Powership is one of our key values, we provided our staff the power to make autonomous decisions from day one. Because we believe our firm is its people, we hired smart builders and let them build.

Nicolas left Spendesk to create scalable interfaces using react-router, react-queries, and MUI. JD joined Swile and chose Hasura as our GraphQL engine. Jérôme chose NestJS to build our backend services. Since then, Justin, Ben, Anas, Yann, Benoit, and others have followed suit.

If you consider your team a collective brain, you should let them make decisions instead of directing them what to do. You'll make mistakes, but you'll go faster and learn faster overall.

Invest in great talent and develop a strong culture from the start. Here's how to establish a SaaS in 100 days.

If you think NFTs are awful, check out the art market.

The fervor around NFTs has subsided in recent months due to the crypto market crash and the media's short attention span. They were all anyone could talk about earlier this spring. Last semester, when passions were high and field luminaries were discussing "slurp juices," I asked my students and students from over 20 other universities what they thought of NFTs.

According to many, NFTs were either tasteless pyramid schemes or a new way for artists to make money. NFTs contributed to the climate crisis and harmed the environment, but so did air travel, fast fashion, and smartphones. Some students complained that NFTs were cheap, tasteless, algorithmically generated schlock, but others asked how this was different from other art.

I'm not sure what I expected, but the intensity of students' reactions surprised me. They had strong, emotional opinions about a technology I'd always considered administrative. NFTs address ownership and accounting, like most crypto/blockchain projects.

Art markets can be irrational, arbitrary, and subject to the same scams and schemes as any market. And maybe a few shenanigans that are unique to the art world.

The Fairness Question

Fairness, a deflating moral currency, was the general sentiment (the less of it in circulation, the more ardently we clamor for it.) These students, almost all of whom are artists, complained to the mismatch between the quality of the work in some notable NFT collections and the excessive amounts these items were fetching on the market. They can sketch a Bored Ape or Lazy Lion in their sleep. Why should they buy ramen with school loans while certain swindlers get rich?

I understand students. Art markets are unjust. They can be irrational, arbitrary, and governed by chance and circumstance, like any market. And art-world shenanigans.

Almost every mainstream critique leveled against NFTs applies just as easily to art markets

Over 50% of artworks in circulation are fake, say experts. Sincere art collectors and institutions are upset by the prevalence of fake goods on the market. Not everyone. Wealthy people and companies use art as investments. They can use cultural institutions like museums and galleries to increase the value of inherited art collections. People sometimes buy artworks and use family ties or connections to museums or other cultural taste-makers to hype the work in their collection, driving up the price and allowing them to sell for a profit. Money launderers can disguise capital flows by using market whims, hype, and fluctuating asset prices.

Almost every mainstream critique leveled against NFTs applies just as easily to art markets.

Art has always been this way. Edward Kienholz's 1989 print series satirized art markets. He stamped 395 identical pieces of paper from $1 to $395. Each piece was initially priced as indicated. Kienholz was joking about a strange feature of art markets: once the last print in a series sells for $395, all previous works are worth at least that much. The entire series is valued at its highest auction price. I don't know what a Kienholz print sells for today (inquire with the gallery), but it's more than $395.

I love Lee Lozano's 1969 "Real Money Piece." Lozano put cash in various denominations in a jar in her apartment and gave it to visitors. She wrote, "Offer guests coffee, diet pepsi, bourbon, half-and-half, ice water, grass, and money." "Offer real money as candy."

Lee Lozano kept track of who she gave money to, how much they took, if any, and how they reacted to the offer of free money without explanation. Diverse reactions. Some found it funny, others found it strange, and others didn't care. Lozano rarely says:

Apr 17 Keith Sonnier refused, later screws lid very tightly back on. Apr 27 Kaltenbach takes all the money out of the jar when I offer it, examines all the money & puts it all back in jar. Says he doesn’t need money now. Apr 28 David Parson refused, laughing. May 1 Warren C. Ingersoll refused. He got very upset about my “attitude towards money.” May 4 Keith Sonnier refused, but said he would take money if he needed it which he might in the near future. May 7 Dick Anderson barely glances at the money when I stick it under his nose and says “Oh no thanks, I intend to earn it on my own.” May 8 Billy Bryant Copley didn’t take any but then it was sort of spoiled because I had told him about this piece on the phone & he had time to think about it he said.

Smart Contracts (smart as in fair, not smart as in Blockchain)

Cornell University's Cheryl Finley has done a lot of research on secondary art markets. I first learned about her research when I met her at the University of Florida's Harn Museum, where she spoke about smart contracts (smart as in fair, not smart as in Blockchain) and new protocols that could help artists who are often left out of the economic benefits of their own work, including women and women of color.

Her talk included findings from her ArtNet op-ed with Lauren van Haaften-Schick, Christian Reeder, and Amy Whitaker.

NFTs allow us to think about and hack on formal contractual relationships outside a system of laws that is currently not set up to service our community.

The ArtNet article The Recent Sale of Amy Sherald's ‘Welfare Queen' Symbolizes the Urgent Need for Resale Royalties and Economic Equity for Artists discussed Sherald's 2012 portrait of a regal woman in a purple dress wearing a sparkling crown and elegant set of pearls against a vibrant red background.

Amy Sherald sold "Welfare Queen" to Princeton professor Imani Perry. Sherald agreed to a payment plan to accommodate Perry's budget.

Amy Sherald rose to fame for her 2016 portrait of Michelle Obama and her full-length portrait of Breonna Taylor, one of the most famous works of the past decade.

As is common, Sherald's rising star drove up the price of her earlier works. Perry's "Welfare Queen" sold for $3.9 million in 2021.

Imani Perry's early investment paid off big-time. Amy Sherald, whose work directly increased the painting's value and who was on an artist's shoestring budget when she agreed to sell "Welfare Queen" in 2012, did not see any of the 2021 auction money. Perry and the auction house got that money.

Sherald sold her Breonna Taylor portrait to the Smithsonian and Louisville's Speed Art Museum to fund a $1 million scholarship. This is a great example of what an artist can do for the community if they can amass wealth through their work.

NFTs haven't solved all of the art market's problems — fakes, money laundering, market manipulation — but they didn't create them. Blockchain and NFTs are credited with making these issues more transparent. More ideas emerge daily about what a smart contract should do for artists.

NFTs are a copyright solution. They allow us to hack formal contractual relationships outside a law system that doesn't serve our community.

Amy Sherald shows the good smart contracts can do (as in, well-considered, self-determined contracts, not necessarily blockchain contracts.) Giving back to our community, deciding where and how our work can be sold or displayed, and ensuring artists share in the equity of our work and the economy our labor creates.