Most don't understand the issue until it's too late.

My first startup was what entrepreneurs call the hardest. A two-sided marketplace.

Two-sided marketplaces are the hardest startups because founders must solve the chicken or the egg conundrum.

A two-sided marketplace needs suppliers and buyers. Without suppliers, buyers won't come. Without buyers, suppliers won't come. An empty marketplace and a founder striving to gain momentum result.

My first venture made me a struggling founder seeking to achieve traction for a two-sided marketplace. The company failed, and I vowed never to start another like it.

I didn’t. Unfortunately, my second venture was almost as hard. It failed like the second-hardest startup.

What kind of startup is the second-hardest?

The second-hardest startup, which is almost as hard to develop, is rarely discussed in the startup community. Because of this, I predict more founders fail each year trying to develop the second-toughest startup than the hardest.

Fairly, I have no proof. I see many startups, so I have enough of firsthand experience. From what I've seen, for every entrepreneur developing a two-sided marketplace, I'll meet at least 10 building this other challenging startup.

I'll describe a startup I just met with its two co-founders to explain the second hardest sort of startup and why it's so hard. They created a financial literacy software for parents of high schoolers.

The issue appears plausible. Children struggle with money. Parents must teach financial responsibility. Problems?

It's possible.

Buyers and users are different.

Buyer-user mismatch.

The financial literacy app I described above targets parents. The parent doesn't utilize the app. Child is end-user. That may not seem like much, but it makes customer and user acquisition and onboarding difficult for founders.

The difficulty of a buyer-user imbalance

The company developing a product faces a substantial operational burden when the buyer and end customer are different. Consider classic firms where the buyer is the end user to appreciate that responsibility.

Entrepreneurs selling directly to end users must educate them about the product's benefits and use. Each demands a lot of time, effort, and resources.

Imagine selling a financial literacy app where the buyer and user are different. To make the first sale, the entrepreneur must establish all the items I mentioned above. After selling, the entrepreneur must supply a fresh set of resources to teach, educate, or train end-users.

Thus, a startup with a buyer-user mismatch must market, sell, and train two organizations at once, requiring twice the work with the same resources.

The second hardest startup is hard for reasons other than the chicken-or-the-egg conundrum. It takes a lot of creativity and luck to solve the chicken-or-egg conundrum.

The buyer-user mismatch problem cannot be overcome by innovation or luck. Buyer-user mismatches must be solved by force. Simply said, when a product buyer is different from an end-user, founders have a lot more work. If they can't work extra, their companies fail.

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!

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.

A completely operating application requires many processes and technical challenges. Implementing coding standards can make apps right, work, and faster.

With years of experience working in software houses. Many client apps are scarcely maintained.

Why are these programs "barely maintainable"? If we're used to coding concepts, we can probably tell if an app is awful or good from its codebase.

This is how I coded much of my app.

Make It Work

Before adopting any concept, make sure the apps are completely functional. Why have a fully maintained codebase if the app can't be used?

The user doesn't care if the app is created on a super server or uses the greatest coding practices. The user just cares if the program helps them.

After the application is working, we may implement coding principles.

You Aren’t Gonna Need It

As a junior software engineer, I kept unneeded code, components, comments, etc., thinking I'd need them later.

In reality, I never use that code for weeks or months.

First, we must remove useless code from our primary codebase. If you insist on keeping it because "you'll need it later," employ version control.

If we remove code from our codebase, we can quickly roll back or copy-paste the previous code without preserving it permanently.

The larger the codebase, the more maintenance required.

Keep It Simple Stupid

Indeed. Keep things simple.

Why complicate something if we can make it simpler?

Our code improvements should lessen the server load and be manageable by others.

If our code didn't pass those benchmarks, it's too convoluted and needs restructuring. Using an open-source code critic or code smell library, we can quickly rewrite the code.

Simpler codebases and processes utilize fewer server resources.

Don't Repeat Yourself

Have you ever needed an action or process before every action, such as ensuring the user is logged in before accessing user pages?

As you can see from the above code, I try to call is user login? in every controller action, and it should be optimized, because if we need to rename the method or change the logic, etc. We can improve this method's efficiency.

We can write a constructor/middleware/before action that calls is_user_login?

The code is more maintainable and readable after refactoring.

Each programming language or framework handles this issue differently, so be adaptable.

Clean Code

Clean code is a broad notion that you've probably heard of before.

When creating a function, method, module, or variable name, the first rule of clean code is to be precise and simple.

The name should express its value or logic as a whole, and follow code rules because every programming language is distinct.

If you want to learn more about this topic, I recommend reading https://www.amazon.com/Clean-Code-Handbook-Software-Craftsmanship/dp/0132350882.

Standing On The Shoulder of Giants

Use industry standards and mature technologies, not your own(s).

There are several resources that explain how to build boilerplate code with tools, how to code with best practices, etc.

I propose following current conventions, best practices, and standardization since we shouldn't innovate on top of them until it gives us a competitive edge.

Boy Scout Rule

What reduces programmers' productivity?

When we have to maintain or build a project with messy code, our productivity decreases.

Having to cope with sloppy code will slow us down (shame of us).

How to cope? Uncle Bob's book says, "Always leave the campground cleaner than you found it."

When developing new features or maintaining current ones, we must improve our codebase. We can fix minor issues too. Renaming variables, deleting whitespace, standardizing indentation, etc.

Make It Fast

After making our code more maintainable, efficient, and understandable, we can speed up our app.

Whether it's database indexing, architecture, caching, etc.

A smart craftsman understands that refactoring takes time and it's preferable to balance all the principles simultaneously. Don't YAGNI phase 1.

Using these ideas in each iteration/milestone, while giving the bottom items less time/care.

You can check one of my articles for further information. https://medium.com/life-at-mekari/why-does-my-website-run-very-slowly-and-how-do-i-optimize-it-for-free-b21f8a2f0162

https://medium.com/life-at-mekari/what-you-need-to-make-your-app-a-high-availability-system-tackling-the-technical-challenges-8896abec363f

These quotes will change your perspective.

I try to reflect on these quotes daily. Reading it in the morning can affect your day, decisions, and priorities. Let's start.

1. Friedrich Nietzsche once said, "He who has a why to live for can bear almost any how."

What's your life goal?

80% of people don't know why they live or what they want to accomplish in life if you ask them randomly.

Even those with answers may not pursue their why. Without a purpose, life can be dull.

Your why can guide you through difficult times.

Create a life goal. Growing may change your goal. Having a purpose in life prevents feeling lost.

2. Seneca said, "He who fears death will never do anything fit for a man in life."

FAILURE STINKS Yes.

This quote is great if you're afraid to try because of failure. What if I'm not made for it? What will they think if I fail?

This wastes most of our lives. Many people prefer not failing over trying something with a better chance of success, according to studies.

Failure stinks in the short term, but it can transform our lives over time.

3. Two men peered through the bars of their cell windows; one saw mud, the other saw stars. — Dale Carnegie

It’s not what you look at that matters; it’s what you see.

The glass-full-or-empty meme is everywhere. It's hard to be positive when facing adversity.

This is a skill. Positive thinking can change our future.

We should stop complaining about our life and how easy success is for others.

Seductive pessimism. Realize this and start from first principles.

4. “Smart people learn from everything and everyone, average people from their experiences, and stupid people already have all the answers.” — Socrates.

Knowing we're ignorant can be helpful.

Every person and situation teaches you something. You can learn from others' experiences so you don't have to. Analyzing your and others' actions and applying what you learn can be beneficial.

Reading (especially non-fiction or biographies) is a good use of time. Walter Issacson wrote Benjamin Franklin's biography. Ben Franklin's early mistakes and successes helped me in some ways.

Knowing everything leads to disaster. Every incident offers lessons.

5. “We must all suffer one of two things: the pain of discipline or the pain of regret or disappointment.“ — James Rohn

My favorite Jim Rohn quote.

Exercise hurts. Healthy eating can be painful. But they're needed to get in shape. Avoiding pain can ruin our lives.

Always choose progress over hopelessness. Myth: overnight success Everyone who has mastered a craft knows that mastery comes from overcoming laziness.

Turn off your inner critic and start working. Try Can't Hurt Me by David Goggins.

6. “A champion is defined not by their wins, but by how they can recover when they fail.“ — Serena Williams

Have you heard of Traf-o-Data?

Gates and Allen founded Traf-O-Data. After some success, it failed. Traf-o-Data's failure led to Microsoft.

Allen said Traf-O-Data's setback was important for Microsoft's first product a few years later. Traf-O-Data was a business failure, but it helped them understand microprocessors, he wrote in 2017.

“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.” — Ryan Holiday.

Bonus Quotes

More helpful quotes:

“Those who cannot change their minds cannot change anything.” — George Bernard Shaw.

“Do something every day that you don’t want to do; this is the golden rule for acquiring the habit of doing your duty without pain.” — Mark Twain.

“Never give up on a dream just because of the time it will take to accomplish it. The time will pass anyway.” — Earl Nightingale.

“A life spent making mistakes is not only more honorable, but more useful than a life spent doing nothing.” — George Bernard Shaw.

“We don’t stop playing because we grow old; we grow old because we stop playing.” — George Bernard Shaw.

Conclusion

Words are powerful. Utilize it. Reading these inspirational quotes will help you.