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.

Christopher Janz of Point Nine Capital created the SaaS napkin in 2016. This post shows how founders have raised cash in the last 6 years. View raw data.

Round size

Unsurprisingly, round sizes have expanded and will taper down in 2022. In 2016, pre-seed rounds were $200k to $500k; currently, they're $1-$2m. Despite the macroeconomic scenario, Series A have expanded from $3m to $12m in 2016 to $6m and $18m in 2022.

Valuation

There are hints that valuations are rebounding this year. Pre-seed valuations in 2022 are $12m from $3m in 2016, and Series B prices are $270m from $100m in 2016.

Compared to public SaaS multiples, Series B valuations more closely reflect the market, but Seed and Series A prices seem to be inflated regardless of the market.

I'd like to know how each annual cohort performed for investors, based on the year they invested and the valuations. I can't access this information.

ARR

Seed firms' ARR forecasts have risen from $0 to $0.6m to $0 to $1m. 2016 expected $1.2m to $3m, 2021 $0.5m to $4m, and this year $0.5m to $2.5m, suggesting that Series A firms may raise with less ARR today. Series B minutes fell from $4.2m to $3m.

Capitalization Rate

2022 is the year that VCs start discussing capital efficiency in portfolio meetings. Given the economic shift in the markets and the stealthy VC meltdown, it's not surprising. Christopher Janz added capital efficiency to the SaaS Napkin as a new statistic for Series A (3.5x) and Series B. (2.5x). Your investors must live under a rock if they haven't asked about capital efficiency. If you're unsure:

The Capital Efficiency Ratio is the ratio of how much a company has spent growing revenue and how much they’re receiving in return. It is the broadest measure of company effectiveness in generating ARR

What next?

No one knows what's next, including me. All startup and growing enterprises around me are tightening their belts and extending their runways in anticipation of a difficult fundraising ride. If you're wanting to raise money but can wait, wait till the market is more stable and access to money is easier.

40 years pass. After 14 years of retirement, you die. Am I the only one who sees the problem?

I’m the Jedi master of escaping the rat race.

Not to impress. I know this works since I've tried it. Quitting a job to make money online is worse than Kim Kardashian's internet-burning advice.

Let me help you rethink the move from a career to online income to f*ck you money.

To understand why a job is a joke, do some life math.

Without a solid why, nothing makes sense.

The retirement age is 65. Our processed food consumption could shorten our 79-year average lifespan.

You spend 40 years working.

After 14 years of retirement, you die.

Am I alone in seeing the problem?

Life is too short to work a job forever, especially since most people hate theirs. After-hours skills are vital.

Money equals unrestricted power, f*ck you.

F*ck you money is the answer.

Jack Raines said it first. He says we can do anything with the money. Jack, a young rebel straight out of college, can travel and try new foods.

F*ck you money signifies not checking your bank account before buying.

F*ck you” money is pure, unadulterated freedom with no strings attached.

Jack claims you're rich when you rarely think about money.

Avoid confusion.

This doesn't imply you can buy a Lamborghini. It indicates your costs, income, lifestyle, and bank account are balanced.

Jack established an online portfolio while working for UPS in Atlanta, Georgia. So he gained boundless power.

The portion that many erroneously believe

Yes, you need internet abilities to make money, but they're not different from 9-5 talents.

Sahil Lavingia, Gumroad's creator, explains.

A job is a way to get paid to learn.

Mistreat your boss 9-5. Drain his skills. Defuse him. Love and leave him (eventually).

Find another employment if yours is hazardous. Pick an easy job. Make sure nothing sneaks into your 6-12 time slot.

The dumb game that makes you a sheep

A 9-5 job requires many job interviews throughout life.

You email your résumé to employers and apply for jobs through advertisements. This game makes you a sheep.

You're competing globally. Work-from-home makes the competition tougher. If you're not the cheapest, employers won't hire you.

After-hours online talents (say, 6 pm-12 pm) change the game. This graphic explains it better:

Online talents boost after-hours opportunities.

You go from wanting to be picked to picking yourself. More chances equal more money. Your f*ck you fund gets the extra cash.

A novel method of learning is essential.

College costs six figures and takes a lifetime to repay.

Informal learning is distinct. 6-12pm:

• Observe the carefully controlled Twitter newsfeed.

• Make use of Teachable and Gumroad's online courses.

• Watch instructional YouTube videos

• Look through the top Substack newsletters.

Informal learning is more effective because it's not obvious. It's fun to follow your curiosity and hobbies.

The majority of people lack one attitude. It's simple to learn.

One big impediment stands in the way of f*ck you money and time independence. So often.

Too many people plan after 6-12 hours. Dreaming. Big-thinkers. Strategically. They fill their calendar with meetings.

This is after-hours masturb*tion.

Sahil Bloom reminded me that a bias towards action will determine if this approach works for you.

The key isn't knowing what to do from 6-12 a.m. Trust yourself and develop abilities as you go. It's for building the parachute after you jump.

Sounds risky. We've eliminated the risk by finishing this process after hours while you work 9-5.

With no risk, you can have an I-don't-care attitude and still be successful.

When you choose to move forward, this occurs.

Once you try 9-5/6-12, you'll tell someone.

It's bad.

Few of us hang out with problem-solvers.

It's how much of society operates. So they make reasons so they can feel better about not giving you money.

Matthew Kobach told me chasing f*ck you money is easier with like-minded folks.

Without f*ck you money friends, loneliness will take over and you'll think you've messed up when you just need to keep going.

Steal this easy guideline

Let's act. No more fluffing and caressing.

1. Learn

If you detest your 9-5 talents or don't think they'll work online, get new ones. If you're skilled enough, continue.

Easlo recommends these skills:

• Designer for Figma

• Designer Canva

• bubble creators

• editor in Photoshop

• Automation consultant for Zapier

• Designer of Webflow

• video editor Adobe

• Ghostwriter for Twitter

• Idea consultant

• Artist in Blender Studio

2. Develop the ability

Every night from 6-12, apply the skill.

Practicing ghostwriting? Write someone's tweets for free. Do someone's website copy to learn copywriting. Get a website to the top of Google for a keyword to understand SEO.

Free practice is crucial. Your 9-5 pays the money, so work for free.

3. Take off stealthily like a badass

Another mistake. Sell to few. Don't be the best. Don't claim expertise.

Sell your new expertise to others behind you.

Two ways:

• Using a digital good

• By providing a service,

Point 1 also includes digital service examples. Digital products include eBooks, communities, courses, ad-supported podcasts, and templates. It's easy. Your 9-5 job involves one of these.

Take ideas from work.

Why? They'll steal your time for profit.

4. Iterate while feeling awful

First-time launches always fail. You'll feel terrible. Okay. Remember your 9-5?

Find improvements. Ask free and paying consumers what worked.

Multiple relaunches, each 1% better.

5. Discover more

Never stop learning. Improve your skill. Add a relevant skill. Learn copywriting if you write online.

After-hours students earn the most.

6. Continue

Repetition is key.

7. Make this one small change.

Consistently. The 6-12 momentum won't make you rich in 30 days; that's success p*rn.

Consistency helps wage slaves become f*ck you money. Most people can't switch between the two.

Putting everything together

It's easy. You're probably already doing some.

This formula explains why, how, and what to do. It's a 5th-grade-friendly blueprint. Good.

Reduce financial risk with your 9-to-5. Replace Netflix with 6-12 money-making talents.

Life is short; do whatever you want. Today.

Kim Kardashian created Skky Partners. Consumer products, internet & e-commerce, consumer media, hospitality, and luxury are company targets.

Some call this another Kardashian publicity gimmick.

This maneuver is brilliance upon closer inspection. Why?

1) Kim has amassed a sizable social media fan base:

Over 320 million Instagram and 70 million Twitter users follow Kim Kardashian.

Kim Kardashian's Instagram account ranks 8th. Three Kardashians in top 10 is ridiculous.

This gives her access to consumer data. She knows what people are discussing. Investment firms need this data.

Quality, not quantity, of her followers matters. Studies suggest that her following are more engaged than Selena Gomez and Beyonce's.

Kim's followers are worth roughly $500 million to her brand, according to a research. They trust her and buy what she recommends.

2) She has a special aptitude for identifying trends.

Kim Kardashian can sense trends.

She's always ahead of fashion and beauty trends. She's always trying new things, too. She doesn't mind making mistakes when trying anything new. Her desire to experiment makes her a good business prospector.

Kim has also created a lifestyle brand that followers love. Kim is an entrepreneur, mom, and role model, not just a reality TV star or model. She's established a brand around her appearance, so people want to buy her things.

Her fragrance collection has sold over $100 million since its 2009 introduction, and her Sears apparel line did over $200 million in its first year.

SKIMS is her latest $3.2bn brand. She can establish multibillion-dollar firms with her enormous distribution platform.

Early founders would kill for Kim Kardashian's network.

Making great products is hard, but distribution is more difficult. — David Sacks, All-in-Podcast

3) She can delegate the financial choices to Jay Sammons, one of the greatest in the industry.

Jay Sammons is well-suited to develop Kim Kardashian's new private equity fund.

Sammons has 16 years of consumer investing experience at Carlyle. This will help Kardashian invest in consumer-facing enterprises.

Sammons has invested in Supreme and Beats Electronics, both of which have grown significantly. Sammons' track record and competence make him the obvious choice.

Kim Kardashian and Jay Sammons have joined forces to create a new business endeavor. The agreement will increase Kardashian's commercial empire. Sammons can leverage one of the world's most famous celebrities.

“Together we hope to leverage our complementary expertise to build the next generation consumer and media private equity firm” — Kim Kardashian

Kim Kardashian is a successful businesswoman. She developed an empire by leveraging social media to connect with fans. By developing a global lifestyle brand, she has sold things and experiences that have made her one of the world's richest celebrities.

She's a shrewd entrepreneur who knows how to maximize on herself and her image.

Imagine how much interest Kim K will bring to private equity and venture capital.

I'm curious about the company's growth.

Jobs' secret emails became public due to a litigation with Samsung.

Steve Jobs sent Phil Schiller an email at the end of 2010. Top 100 A was the codename for Apple's annual Top 100 executive meetings. The 2011 one was scheduled.

Everything about this gathering is secret, even attendance. The location is hidden, and attendees can't even drive themselves. Instead, buses transport them to a 2-3 day retreat.

Due to a litigation with Samsung, this Top 100 meeting's agenda was made public in 2014. This was a critical milestone in Apple's history, not a Top 100 meeting. Apple had many obstacles in the 2010s to remain a technological leader. Apple made more money with non-PC goods than with its best-selling Macintosh series. This was the last Top 100 gathering Steve Jobs would attend before passing, and he wanted to make sure his messages carried on before handing over his firm to Tim Cook.

In this post, we'll discuss lessons from Jobs' meeting agenda. Two sorts of entrepreneurs can use these tips:

1. Those who manage a team in a business and must ensure that everyone is working toward the same goals, upholding the same principles, and being inspired by the same future.

2. Those who are sole proprietors or independent contractors and who must maintain strict self-discipline in order to stay innovative in their industry and adhere to their own growth strategy.

Here's Steve Jobs's email outlining the annual meeting agenda. It's an 11-part summary of the company's shape and strategy.

Steve Jobs outlines Apple's 2011 strategy, 10/24/10

1. Correct your data

Business leaders must comprehend their company's metrics. Jobs either mentions critical information he already knows or demands slides showing the numbers he wants. These numbers fall under 2 categories:

Metrics for growth and strategy

• As we will see, this was a crucial statistic for Apple since it signaled the beginning of the Post PC era and required them to make significant strategic changes in order to stay ahead of the curve. Post PC products now account for 66% of our revenues.

• Within six months, iPad outsold Mac, another sign of the Post-PC age. As we will see, Jobs thought the iPad would be the next big thing, and item number four on the agenda is one of the most thorough references to the iPad.

• Geographical analysis: Here, Jobs emphasizes China, where the corporation has a slower start than anticipated. China was dominating Apple's sales growth with 16% of revenue one year after this meeting.

Metrics for people & culture

• The individuals that make up a firm are more significant to its success than its headcount or average age. That holds true regardless of size, from a 5-person startup to a Fortune 500 firm. Jobs was aware of this, which is why his suggested agenda begins by emphasizing demographic data.

• Along with the senior advancements in the previous year's requested statistic, it's crucial to demonstrate that if the business is growing, the employees who make it successful must also grow.

2. Recognize the vulnerabilities and strengths of your rivals

Steve Jobs was known for attacking his competition in interviews and in his strategies and roadmaps. This agenda mentions 18 competitors, including:

• Google 7 times

• Android 3 times

• Samsung 2 times

Jobs' agenda email was issued 6 days after Apple's Q4 results call (2010). On the call, Jobs trashed Google and Android. His 5-minute intervention included:

• Google has acknowledged that the present iteration of Android is not tablet-optimized.

• Future Android tablets will not work (Dead On Arrival)

• While Google Play only has 90,000 apps, the Apple App Store has 300,000.

• Android is extremely fragmented and is continuing to do so.

• The App Store for iPad contains over 35,000 applications. The market share of the latest generation of tablets (which debuted in 2011) will be close to nil.

Jobs' aim in blasting the competition on that call was to reassure investors about the upcoming flood of new tablets. Jobs often criticized Google, Samsung, and Microsoft, but he also acknowledged when they did a better job. He was great at detecting his competitors' advantages and devising ways to catch up.

• Jobs doesn't hold back when he says in bullet 1 of his agenda: "We further lock customers into our ecosystem while Google and Microsoft are further along on the technology, but haven't quite figured it out yet tie all of our goods together."

• The plan outlined in bullet point 5 is immediately clear: catch up to Android where we are falling behind (notifications, tethering, and speech), and surpass them (Siri,). It's important to note that Siri frequently let users down and never quite lived up to expectations.

• Regarding MobileMe, see Bullet 6 Jobs admits that when it comes to cloud services like contacts, calendars, and mail, Google is far ahead of Apple.

3. Adapt or perish

Steve Jobs was a visionary businessman. He knew personal computers were the future when he worked on the first Macintosh in the 1980s.

Jobs acknowledged the Post-PC age in his 2010 D8 interview.

Will the tablet replace the laptop, Walt Mossberg questioned Jobs? Jobs' response:

“You know, when we were an agrarian nation, all cars were trucks, because that’s what you needed on the farm. As vehicles started to be used in the urban centers and America started to move into those urban and suburban centers, cars got more popular and innovations like automatic transmission and things that you didn’t care about in a truck as much started to become paramount in cars. And now, maybe 1 out of every 25 vehicles is a truck, where it used to be 100%. PCs are going to be like trucks. They’re still going to be around, still going to have a lot of value, but they’re going to be used by one out of X people.”

Imagine how forward-thinking that was in 2010, especially for the Macintosh creator. You have to be willing to recognize that things were changing and that it was time to start over and focus on the next big thing.

Post-PC is priority number 8 in his 2010 agenda's 2011 Strategy section. Jobs says Apple is the first firm to get here and that Post PC items account about 66% of our income. The iPad outsold the Mac in 6 months, and the Post-PC age means increased mobility (smaller, thinner, lighter). Samsung had just introduced its first tablet, while Apple was working on the iPad 3. (as mentioned in bullet 4).

4. Plan ahead (and different)

Jobs' agenda warns that Apple risks clinging to outmoded paradigms. Clayton Christensen explains in The Innovators Dilemma that huge firms neglect disruptive technologies until they become profitable. Samsung's Galaxy tab, released too late, never caught up to Apple.

Apple faces a similar dilemma with the iPhone, its cash cow for over a decade. It doesn't sell as much because consumers aren't as excited about new iPhone launches and because technology is developing and cell phones may need to be upgraded.

Large companies' established consumer base typically hinders innovation. Clayton Christensen emphasizes that loyal customers from established brands anticipate better versions of current products rather than something altogether fresh and new technologies.

Apple's marketing is smart. Apple's ecosystem is trusted by customers, and its products integrate smoothly. So much so that Apple can afford to be a disruptor by doing something no one has ever done before, something the world's largest corporation shouldn't be the first to try. Apple can test the waters and produce a tremendous innovation tsunami, something few corporations can do.

In March 2011, Jobs appeared at an Apple event. During his address, Steve reminded us about Apple's brand:

“It’s in Apple’s DNA, that technology alone is not enough. That it’s technology married with liberal arts, married with the humanities that yields us the results that make our hearts sink. And nowhere is that more true that in these Post-PC devices.“

More than a decade later, Apple remains one of the most innovative and trailblazing companies in the Post-PC world (industry-disrupting products like Airpods or the Apple Watch came out after that 2011 strategy meeting), and it has reinvented how we use laptops with its M1-powered line of laptops offering unprecedented performance.

A decade after Jobs' death, Apple remains the world's largest firm, and its former CEO had a crucial part in its expansion. If you can do 1% of what Jobs did, you may be 1% as successful.

Not bad.