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.

I recently wrote about getting VCs excited about Marketplace start-ups. SaaS founders became envious!

Understanding how people wire tens of millions is the only Series A hack I recommend.

Few people understand the intellectual process behind investing.

VC is risk management.

Series A-focused VCs must cover two risks.

1. Market risk

You need a large market to cross a threshold beyond which you can build defensibilities. Series A VCs underwrite market risk.

They must see you have reached product-market fit (PMF) in a large total addressable market (TAM).

2. Execution risk

When evaluating your growth engine's blitzscaling ability, execution risk arises.

When investors remove operational uncertainty, they profit.

Series A VCs like businesses with derisked revenue streams. Don't raise unless you have a predictable model, pipeline, and growth.

Please beat these 3 metrics before Series A:

Achieve $1.5m ARR in 12-24 months (Market risk)

Above 100% Net Dollar Retention. (Market danger)

Lead Velocity Rate supporting $10m ARR in 2–4 years (Execution risk)

Hit the 3 and you'll raise $10M in 4 months. Discussing 2/3 may take 6–7 months.

If none, don't bother raising and focus on becoming a capital-efficient business (Topics for other posts).

Let's examine these 3 metrics for the brave ones.

1. Lead Velocity Rate supporting €$10m ARR in 2 to 4 years

Last because it's the least discussed. LVR is the most reliable data when evaluating a growth engine, in my opinion.

SaaS allows you to see the future.

Monthly Sales and Sales Pipelines, two predictive KPIs, have poor data quality. Both are lagging indicators, and minor changes can cause huge modeling differences.

Analysts and Associates will trash your forecasts if they're based only on Monthly Sales and Sales Pipeline.

LVR, defined as month-over-month growth in qualified leads, is rock-solid. There's no lag. You can See The Future if you use Qualified Leads and a consistent formula and process to qualify them.

With this metric in your hand, scaling your company turns into an execution play on which VCs are able to perform calculations risk.

2. Above-100% Net Dollar Retention.

Net Dollar Retention is a better-known SaaS health metric than LVR.

Net Dollar Retention measures a SaaS company's ability to retain and upsell customers. Ask what $1 of net new customer spend will be worth in years n+1, n+2, etc.

Depending on the business model, SaaS businesses can increase their share of customers' wallets by increasing users, selling them more products in SaaS-enabled marketplaces, other add-ons, and renewing them at higher price tiers.

If a SaaS company's annualized Net Dollar Retention is less than 75%, there's a problem with the business.

Slack's ARR chart (below) shows how powerful Net Retention is. Layer chart shows how existing customer revenue grows. Slack's S1 shows 171% Net Dollar Retention for 2017–2019.

Slack S-1

3. $1.5m ARR in the last 12-24 months.

According to Point 9, $0.5m-4m in ARR is needed to raise a $5–12m Series A round.

Target at least what you raised in Pre-Seed/Seed. If you've raised $1.5m since launch, don't raise before $1.5m ARR.

Capital efficiency has returned since Covid19. After raising $2m since inception, it's harder to raise $1m in ARR.

P9's 2016-2021 SaaS Funding Napkin

In summary, less than 1% of companies VCs meet get funded. These metrics can help you win.

If there’s demand for it, I’ll do one on direct-to-consumer.

Cheers!

Are you an idiot at fundraising?

Humans undervalue what they don't grasp. Consider NASCAR. How is that a sport? ask uneducated observers. Circular traffic. Driving near a car's physical limits is different from daily driving. When driving at 200 mph, seemingly simple things like changing gas weight or asphalt temperature might be life-or-death.

Venture investors do something similar in entrepreneurship. Most entrepreneurs don't realize how complex venture finance is.

In my early startup days, I didn't comprehend venture capital's intricacy. I thought VCs were rich folks looking for the next Mark Zuckerberg. I was meant to be a sleek, enthusiastic young entrepreneur who could razzle-dazzle investors.

Finally, one of the VCs I was trying to woo set me straight. He insulted me.

How I learned that I was approaching the wrong investor

I was constructing a consumer-facing, pre-revenue marketplace firm. I looked for investors in my old university's alumni database. My city had one. After some research, I learned he was a partner at a growth-stage, energy-focused VC company with billions under management.

Billions? I thought. Surely he can write a million-dollar cheque. He'd hardly notice.

I emailed the VC about our shared alumni status, explaining that I was building a startup in the area and wanted advice. When he agreed to meet the next week, I prepared my pitch deck.

First error.

The meeting seemed like a funding request. Imagine the awkwardness.

His assistant walked me to the firm's conference room and told me her boss was running late. While waiting, I prepared my pitch. I connected my computer to the projector, queued up my PowerPoint slides, and waited for the VC.

He didn't say hello or apologize when he entered a few minutes later. What are you doing?

Hi! I said, Confused but confident. Dinin Aaron. My startup's pitch.

Who? Suspicious, he replied. Your email says otherwise. You wanted help.

I said, "Isn't that a euphemism for contacting investors?" Fundraising I figured I should pitch you.

As he sat down, he smiled and said, "Put away your computer." You need to study venture capital.

Recognizing the business aspects of venture capital

The VC taught me venture capital in an hour. Young entrepreneur me needed this lesson. I assume you need it, so I'm sharing it.

Most people view venture money from an entrepreneur's perspective, he said. They envision a world where venture capital serves entrepreneurs and startups.

As my VC indicated, VCs perceive their work differently. Venture investors don't serve entrepreneurs. Instead, they run businesses. Their product doesn't look like most products. Instead, the VCs you're proposing have recognized an undervalued market segment. By investing in undervalued companies, they hope to profit. It's their investment thesis.

Your company doesn't fit my investment thesis, the venture capitalist told me. Your pitch won't beat my investing theory. I invest in multimillion-dollar clean energy companies. Asking me to invest in you is like ordering a breakfast burrito at a fancy steakhouse. They could, but why? They don't do that.

Yeah, I’m not a fine steak yet, I laughed, feeling like a fool for pitching a growth-stage VC used to looking at energy businesses with millions in revenues on my pre-revenue, consumer startup.

He stressed that it's not necessary. There are investors targeting your company. Not me. Find investors and pitch them.

Remember this when fundraising. Your investors aren't philanthropists who want to help entrepreneurs realize their company goals. Venture capital is a sophisticated investment strategy, and VC firm managers are industry experts. They're looking for companies that meet their investment criteria. As a young entrepreneur, I didn't grasp this, which is why I struggled to raise money. In retrospect, I probably seemed like an idiot. Hopefully, you won't after reading this.

VeeFriends is one NFT project I'm sure will last.

I believe in blockchain technology and JPEGs, aka NFTs. NFTs aren't JPEGs. It's not as it seems.

Gary Vaynerchuk is leading the pack with his new NFT project VeeFriends, I wrote a year ago. I was spot-on. It's the most innovative project I've seen.

Since its minting in May 2021, it has given its holders enormous value, most notably the first edition of VeeCon, a multi-day superconference featuring iconic and emerging leaders in NFTs and Popular Culture. First-of-its-kind NFT-ticketed Web3 conference to build friendships, share ideas, and learn together.

VeeFriends holders got free VeeCon NFT tickets. Attendees heard iconic keynote speeches, innovative talks, panels, and Q&A sessions.

It was a unique conference that most of us, including me, are looking forward to in 2023. The lineup was epic, and it allowed many to network in new ways. Really memorable learning. Here are a couple of gratitude posts from the attendees.

VeeFriends Series 2

This article explains VeeFriends if you're still confused.

GaryVee's hand-drawn doodles have evolved into wonderful characters. The characters' poses and backgrounds bring the VeeFriends IP to life.

Yes, this is the second edition of VeeFriends, and at current prices, it's one of the best NFT opportunities in years. If you have the funds and risk appetite to invest in NFTs, VeeFriends Series 2 is worth every penny. Even if you can't invest, learn from their journey.

1. Art Is the Start

Many critics say VeeFriends artwork is below average and not by GaryVee. Art is often the key to future success.

Let's look at one of the first Mickey Mouse drawings. No one would have guessed that this would become one of the most beloved animated short film characters. In Walt Before Mickey, Walt Disney's original mouse Mortimer was less refined.

First came a mouse...

These sketches evolved into Steamboat Willie, Disney's first animated short film.

Fred Moore redesigned the character artwork into what we saw in cartoons as kids. Mickey Mouse's history is here.

Looking at how different cartoon characters have evolved and gained popularity over decades, I believe Series 2 characters like Self-Aware Hare, Kind Kudu, and Patient Pig can do the same.

GaryVee captures this journey on the blockchain and lets early supporters become part of history. Time will tell if it rivals Disney, Pokemon, or Star Wars. Gary has been vocal about this vision.

2. VeeFriends is Intellectual Property for the Coming Generations

Most of us grew up watching cartoons, playing with toys, cards, and video games. Our interactions with fictional characters and the stories we hear shape us.

GaryVee is slowly curating an experience for the next generation with animated videos, card games, merchandise, toys, and more.

VeeFriends UNO, a collaboration with Mattel Creations, features 17 VeeFriends characters.

VeeFriends and Zerocool recently released Trading Cards featuring all 268 Series 1 characters and 15 new ones. Another way to build VeeFriends' collectibles brand.

At Veecon, all the characters were collectible toys. Something will soon emerge.

Kids and adults alike enjoy the YouTube channel's animated shorts and VeeFriends Tunes. Here's a song by the holder's Optimistic Otter-loving daughter.

This VeeFriends story is only the beginning. I'm looking forward to animated short film series, coloring books, streetwear, candy, toys, physical collectibles, and other forms of VeeFriends IP.

3. Veefriends will always provide utilities

Smart contracts can be updated at any time and authenticated on a ledger.

VeeFriends Series 2 gives no promise of any utility whatsoever. GaryVee released no project roadmap. In the first few months after launch, many owners of specific characters or scenes received utilities.

Every benefit or perk you receive helps promote the VeeFriends brand.

Recent partnerships are listed below.

• MaryRuth's Multivitamin Gummies

• Productive Puffin holders from VeeFriends x Primitive

• Pickleball Scene & Clown Holders Only

Pickleball & Competitive Clown Exclusive experience, anteater multivitamin gummies, and Puffin x Primitive merch

Considering the price of NFTs, it may not seem like much. It's just the beginning; you never know what the future holds. No other NFT project offers such diverse, ongoing benefits.

4. Garyvee's team is ready

Gary Vaynerchuk's team and record are undisputed. He's a serial entrepreneur and the Chairman & CEO of VaynerX, which includes VaynerMedia, VaynerCommerce, One37pm, and The Sasha Group.

Gary founded VaynerSports, Resy, and Empathy Wines. He's a Candy Digital Board Member, VCR Group Co-Founder, ArtOfficial Co-Founder, and VeeFriends Creator & CEO. Gary was recently named one of Fortune's Top 50 NFT Influencers.

Gary Vayenerchuk aka GaryVee

Gary documents his daily life as a CEO on social media, which has 34 million followers and 272 million monthly views. GaryVee Audio Experience is a top podcast. He's a five-time New York Times best-seller and sought-after speaker.

Gary can observe consumer behavior to predict trends. He understood these trends early and pioneered them.

• 1997 — Realized e-potential commerce's and started winelibrary.com. In five years, he grew his father's wine business from $3M to $60M.

• 2006 — Realized content marketing's potential and started Wine Library on YouTube. TV

• 2009 — Estimated social media's potential (Web2) and invested in Facebook, Twitter, and Tumblr.

• 2014: Ethereum and Bitcoin investments

• 2021 — Believed in NFTs and Web3 enough to launch VeeFriends

GaryVee isn't all of VeeFriends. Andy Krainak, Dave DeRosa, Adam Ripps, Tyler Dowdle, and others work tirelessly to make VeeFriends a success.

GaryVee has said he'll let other businesses fail but not VeeFriends. We're just beginning his 40-year vision.

I have more confidence than ever in a company with a strong foundation and team.

5. Humans die, but characters live forever

What if GaryVee dies or can't work?

A writer's books can immortalize them. As long as their books exist, their words are immortal. Socrates, Hemingway, Aristotle, Twain, Fitzgerald, and others have become immortal.

Everyone knows Vincent Van Gogh's The Starry Night.

We all love reading and watching Peter Parker, Thor, or Jessica Jones. Their behavior inspires us. Stan Lee's message and stories live on despite his death.

GaryVee represents VeeFriends. Creating characters to communicate ensures that the message reaches even those who don't listen.

Gary wants his values and messages to be omnipresent in 268 characters. Messengers die, but their messages live on.

Gary envisions VeeFriends creating timeless stories and experiences. Ten years from now, maybe every kid will sing Patient Pig.

6. I love the intent.

Gary planned to create Workplace Warriors three years ago when he began designing Patient Panda, Accountable Ant, and Empathy elephant. The project stalled. When NFTs came along, he knew.

Gary wanted to create characters with traits he values, such as accountability, empathy, patience, kindness, and self-awareness. He wants future generations to find these traits cool. He hopes one or more of his characters will become pop culture icons.

These emotional skills aren't taught in schools or colleges, but they're crucial for business and life success. I love that someone is teaching this at scale.

In the end, intent matters.

Humans Are Collectors

Buy and collect things to communicate. Since the 1700s. Medieval people formed communities around hidden metals and stones. Many people still collect stamps and coins, and luxury and fashion are multi-trillion dollar industries. We're collectors.

The early 2020s NFTs will be remembered in the future. VeeFriends will define a cultural and technological shift in this era. VeeFriends Series 1 is the original hand-drawn art, but it's expensive. VeeFriends Series 2 is a once-in-a-lifetime opportunity at $1,000.

If you are new to NFTs, check out How to Buy a Non Fungible Token (NFT) For Beginners

This is a non-commercial article. Not financial or legal advice. Information isn't always accurate. Before making important financial decisions, consult a pro or do your own research.

This post is a summary. Read the full article here

While we played checkers, we thought billionaires played 3D chess. They're playing the same game on a fancier board.

Every medium has nuances and norms. Texting is authentic and casual. A smaller circle has access, creating intimacy and immediacy. Most people read all their texts, but not all their email and mail. Many of us no longer listen to our voicemails, and calling your kids ages you.

Live interviews and testimony under oath inspire real moments, rare in a world where communications departments sanitize everything powerful people say. When (some of) Elon's text messages became public in Twitter v. Musk, we got a glimpse into tech power. It's bowels.

These texts illuminate the tech community's upper caste.

Checkers, Not Chess

Elon texts with Larry Ellison, Joe Rogan, Sam Bankman-Fried, Satya Nadella, and Jack Dorsey. They reveal astounding logic, prose, and discourse. The world's richest man and his followers are unsophisticated, obtuse, and petty. Possibly. While we played checkers, we thought billionaires played 3D chess. They're playing the same game on a fancier board.

They fumble with their computers.

They lean on others to get jobs for their kids (no surprise).

No matter how rich, they always could use more (money).

Differences A social hierarchy exists. Among this circle, the currency of deference is... currency. Money increases sycophantry. Oculus and Elon's "friends'" texts induce nausea.

Autocorrect frustrates everyone.

Elon doesn't stand out to me in these texts; he comes off mostly OK in my view. It’s the people around him. It seems our idolatry of innovators has infected the uber-wealthy, giving them an uncontrollable urge to kill the cool kid for a seat at his cafeteria table. "I'd grenade for you." If someone says this and they're not fighting you, they're a fan, not a friend.

Many powerful people are undone by their fake friends. Facilitators, not well-wishers. When Elon-Twitter started, I wrote about power. Unchecked power is intoxicating. This is a scientific fact, not a thesis. Power causes us to downplay risk, magnify rewards, and act on instincts more quickly. You lose self-control and must rely on others.

You'd hope the world's richest person has advisers who push back when necessary (i.e., not yes men). Elon's reckless, childish behavior and these texts show there is no truth-teller. I found just one pushback in the 151-page document. It came from Twitter CEO Parag Agrawal, who, in response to Elon’s unhelpful “Is Twitter dying?” tweet, let Elon know what he thought: It was unhelpful. Elon’s response? A childish, terse insult.

Scale

The texts are mostly unremarkable. There are some, however, that do remind us the (super-)rich are different. Specifically, the discussions of possible equity investments from crypto-billionaire Sam Bankman-Fried (“Does he have huge amounts of money?”) and this exchange with Larry Ellison:

Ellison, who co-founded $175 billion Oracle, is wealthy. Less clear is whether he can text a billion dollars. Who hasn't been texted $1 billion? Ellison offered 8,000 times the median American's net worth, enough to buy 3,000 Ferraris or the Chicago Blackhawks. It's a bedrock principle of capitalism to have incredibly successful people who are exponentially wealthier than the rest of us. It creates an incentive structure that inspires productivity and prosperity. When people offer billions over text to help a billionaire's vanity project in a country where 1 in 5 children are food insecure, isn't America messed up?

Elon's Morgan Stanley banker, Michael Grimes, tells him that Web3 ventures investor Bankman-Fried can invest $5 billion in the deal: “could do $5bn if everything vision lock... Believes in your mission." The message bothers Elon. In Elon's world, $5 billion doesn't warrant a worded response. $5 billion is more than many small nations' GDP, twice the SEC budget, and five times the NRC budget.

If income inequality worries you after reading this, trust your gut.

Billionaires aren't like the rich.

As an entrepreneur, academic, and investor, I've met modest-income people, rich people, and billionaires. Rich people seem different to me. They're smarter and harder working than most Americans. Monty Burns from The Simpsons is a cartoon about rich people. Rich people have character and know how to make friends. Success requires supporters.

I've never noticed a talent or intelligence gap between wealthy and ultra-wealthy people. Conflating talent and luck infects the tech elite. Timing is more important than incremental intelligence when going from millions to hundreds of millions or billions. Proof? Elon's texting. Any man who electrifies the auto industry and lands two rockets on barges is a genius. His mega-billions come from a well-regulated capital market, enforceable contracts, thousands of workers, and billions of dollars in government subsidies, including a $465 million DOE loan that allowed Tesla to produce the Model S. So, is Mr. Musk a genius or an impressive man in a unique time and place?

The Point

Elon's texts taught us more? He can't "fix" Twitter. For two weeks in April, he was all in on blockchain Twitter, brainstorming Dogecoin payments for tweets with his brother — i.e., paid speech — while telling Twitter's board he was going to make a hostile tender offer. Kimbal approved. By May, he was over crypto and "laborious blockchain debates." (Mood.)

Elon asked the Twitter CEO for "an update from the Twitter engineering team" No record shows if he got the meeting. It doesn't "fix" Twitter either. And this is Elon's problem. He's a grown-up child with all the toys and no boundaries. His yes-men encourage his most facile thoughts, and shitposts and errant behavior diminish his genius and ours.

Post-Apocalyptic

The universe's titans have a sense of humor.

Every day, we must ask: Who keeps me real? Who will disagree with me? Who will save me from my psychosis, which has brought down so many successful people? Elon Musk doesn't need anyone to jump on a grenade for him; he needs to stop throwing them because one will explode in his hand.