Higher startup valuations are often favorable for all parties. High valuations show a business's potential. New customers and talent are attracted. They earn respect.

Everyone benefits if a company's valuation rises.

Founders and investors have always been incentivized to overestimate a company's value.

Post-money valuations were inflated by 2021 market expectations and the valuation model's mechanisms.

Founders must understand both levers to handle a normalizing market.

2021, the year of miracles

2021 must've seemed miraculous to entrepreneurs, employees, and VCs. Valuations rose, and funding resumed after the first Covid-19 epidemic caution.

In 2021, VC investments increased from $335B to $643B. 518 new worldwide unicorns vs. 134 in 2020; 951 US IPOs vs. 431.

Things can change quickly, as 2020-21 showed.

Rising interest rates, geopolitical developments, and normalizing technology conditions drive down share prices and tech company market caps in 2022. Zoom, the poster-child of early lockdown success, is down 37% since 1st Jan.

Once-inflated valuations can become a problem in a normalizing market, especially for founders, employees, and early investors.

the reason why startups are always overvalued

To see why inflated valuations are a problem, consider one of its causes.

Private company values only fluctuate following a new investment round, unlike publicly-traded corporations. The startup's new value is calculated simply:

(Latest round share price) x (total number of company shares)

This is the industry standard Post-Money Valuation model.

Let’s illustrate how it works with an example. If a VC invests $10M for 1M shares (at $10/share), and the company has 10M shares after the round, its Post-Money Valuation is $100M (10/share x 10M shares).

This approach might seem like the most natural way to assess a business, but the model often unintentionally overstates the underlying value of the company even if the share price paid by the investor is fair. All shares aren't equal.

New investors in a corporation will always try to minimize their downside risk, or the amount they lose if things go wrong. New investors will try to negotiate better terms and pay a premium.

How the value of a struggling SpaceX increased

SpaceX's 2008 Series D is an example. Despite the financial crisis and unsuccessful rocket launches, the company's Post-Money Valuation was 36% higher after the investment round. Why?

Series D SpaceX shares were protected. In case of liquidation, Series D investors were guaranteed a 2x return before other shareholders.

Due to downside protection, investors were willing to pay a higher price for this new share class.

The Post-Money Valuation model overpriced SpaceX because it viewed all the shares as equal (they weren't).

Why entrepreneurs, workers, and early investors stand to lose the most

Post-Money Valuation is an effective and sufficient method for assessing a startup's valuation, despite not taking share class disparities into consideration.

In a robust market, where the firm valuation will certainly expand with the next fundraising round or exit, the inflated value is of little significance.

Fairness endures. If a corporation leaves at a greater valuation, each stakeholder will receive a proportional distribution. (i.e., 5% of a $100M corporation yields $5M).

SpaceX's inherent overvaluation was never a problem. Had it been sold for less than its Post-Money Valuation, some shareholders, including founders, staff, and early investors, would have seen their ownership drop.

The unforgiving world of 2022

In 2022, founders, employees, and investors who benefited from inflated values will face below-valuation exits and down-rounds.

For them, 2021 will be a curse, not a blessing.

Some tech giants are worried. Klarna's valuation fell from $45B (Oct 21) to $30B (Jun 22), Canvas from $40B to $27B, and GoPuffs from $17B to $8.3B.

Shazam and Blue Apron have to exit or IPO at a cheaper price. Premium share classes are protected, while others receive less. The same goes for bankrupts.

Those who continue at lower valuations will lose reputation and talent. When their value declines by half, generous employee stock options become less enticing, and their ability to return anything is questioned.

What can we infer about the present situation?

Such techniques to enhance your company's value or stop a normalizing market are fiction.

The current situation is a painful reminder for entrepreneurs and a crucial lesson for future firms.

The devastating market fall of the previous six months has taught us one thing:

1. Keep in mind that any valuation is speculative. Money Post A startup's valuation is a highly simplified approximation of its true value, particularly in the early phases when it lacks significant income or a cutting-edge product. It is merely a projection of the future and a hypothetical meter. Until it is achieved by an exit, a valuation is nothing more than a number on paper.
   

2. Assume the value of your company is lower than it was in the past. Your previous valuation might not be accurate now due to substantial changes in the startup financing markets. There is little reason to think that your company's value will remain the same given the 50%+ decline in many newly listed IT companies. Recognize how the market situation is changing and use caution.
   

3. Recognize the importance of the stake you hold. Each share class has a unique value that varies. Know the sort of share class you own and how additional contractual provisions affect the market value of your security. Frameworks have been provided by Metrick and Yasuda (Yale & UC) and Gornall and Strebulaev (Stanford) for comprehending the terms that affect investors' cash-flow rights upon withdrawal. As a result, you will be able to more accurately evaluate your firm and determine the worth of each share class.
   

4. Be wary of approving excessively protective share terms.
   The trade-offs should be considered while negotiating subsequent rounds. Accepting punitive contractual terms could first seem like a smart option in order to uphold your inflated worth, but you should proceed with caution. Such provisions ALWAYS result in misaligned shareholders, with common shareholders (such as you and your staff) at the bottom of the list.

Open to ideas or acquisitions

Failure is an unavoidable aspect of life, yet many recoil at the word.

I've worked on unrelated startup projects. This is a list of products I developed (often as the tech lead or co-founder) and why they failed to launch.

Chess Bet (Betting)

As a chess player who plays 5 games a day and has an ELO rating of 2100, I tried to design a chess engine to rival stockfish and Houdini.

While constructing my chess engine, my cofounder asked me about building a p2p chess betting app. Chess Bet. There couldn't be a better time.

Two people in different locations could play a staked game. The winner got 90% of the bet and we got 10%. The business strategy was clear, but our mini-launch was unusual.

People started employing the same cheat engines I mentioned, causing user churn and defaming our product.

It was the first programming problem I couldn't solve after building a cheat detection system based on player move strengths and prior games. Chess.com, the most famous online chess software, still suffers from this.

We decided to pivot because we needed an expensive betting license.

We relaunched as Chess MVP after deciding to focus on chess learning. A platform for teachers to create chess puzzles and teach content. Several chess students used our product, but the target market was too tiny.

We chose to quit rather than persevere or pivot.

BodaCare (Insure Tech)

‘BodaBoda’ in Swahili means Motorcycle. My Dad approached me in 2019 (when I was working for a health tech business) about establishing an Insurtech/fintech solution for motorbike riders to pay for insurance using SNPL.

We teamed up with an underwriter to market motorcycle insurance. Once they had enough premiums, they'd get an insurance sticker in the mail. We made it better by splitting the cover in two, making it more reasonable for motorcyclists struggling with lump-sum premiums.

Lack of capital and changing customer behavior forced us to close, with 100 motorcyclists paying 0.5 USD every day. Our unit econ didn't make sense, and CAC and retention capital only dug us deeper.

Circle (Social Networking)

Having learned from both product failures, I began to understand what worked and what didn't. While reading through Instagram, an idea struck me.

Suppose social media weren't virtual.

Imagine meeting someone on your way home. Like-minded person

People were excited about social occasions after covid restrictions were eased. Anything to escape. I just built a university student-popular experiences startup. Again, there couldn't be a better time.

I started the Android app. I launched it on Google Beta and oh my! 200 people joined in two days.

It works by signaling if people are in a given place and allowing users to IM in hopes of meeting up in near real-time. Playstore couldn't deploy the app despite its success in beta for unknown reasons. I appealed unsuccessfully.

My infrastructure quickly lost users because I lacked funding.

In conclusion

This essay contains many failures, some of which might have been avoided and others not, but they were crucial learning points in my startup path.

If you liked any idea, I have the source code on Github.

Happy reading until then!

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.

Old power paradigm blocks new planetary paradigm

The difference between our reality and the media's reality is like a tale of two worlds. The greatest and worst of times, really.

Expanding information demands complex skills and understanding to separate important information from ignorance and crap. And that's just the start of determining the source's aim.

Trust who? We see people trust liars in public and then be destroyed by their decisions. Mistakes may be devastating.

Many give up and don't trust anyone. Reality is a choice, though. Same risks.

We must separate our needs and wants from reality. Needs and wants have rules. Greed and selfishness create an unlivable planet.

Culturally, we know this, but we ignore it as foolish. Selfish and greedy people obtain what they want, while others suffer.

We invade, plunder, rape, and burn. We establish civilizations by institutionalizing an exploitable underclass and denying its existence. These cultural lies promote greed and selfishness despite their destructiveness.

Controlling parts of society institutionalize these lies as fact. Many of each age are willing to gamble on greed because they were taught to see greed and selfishness as principles justified by prosperity.

Our cultural understanding recognizes the long-term benefits of collaboration and sharing. This older understanding generates an increasing tension between greedy people and those who see its planetary effects.

Survival requires distinguishing between global and regional realities. Simple, yet many can't do it. This is the first time human greed has had a global impact.

In the past, conflict stories focused on regional winners and losers. Losers lose, winners win, etc. Powerful people see potential decades of nuclear devastation as local, overblown, and not personally dangerous.

Mutually Assured Destruction (MAD) was a human choice that required people to acquiesce to irrational devastation. This prevented nuclear destruction. Most would refuse.

A dangerous “solution” relies on nuclear trigger-pullers not acting irrationally. Since then, we've collected case studies of sane people performing crazy things in experiments. We've been lucky, but the climate apocalypse could be different.

Climate disaster requires only continuing current behavior. These actions already cause global harm, but that's not a threat. These activities must be viewed differently.

Once grasped, denying planetary facts is hard to accept. Deniers can't think beyond regional power. Seeing planet-scale is unusual.

Decades of indoctrination defining any planetary perspective as un-American implies communal planetary assets are for plundering. The old paradigm limits any other view.

In the same way, the new paradigm sees the old regional power paradigm as a threat to planetary civilization and lifeforms. Insane!

While MAD relied on leaders not acting stupidly to trigger a nuclear holocaust, the delayed climatic holocaust needs correcting centuries of lunacy. We must stop allowing craziness in global leadership.

Nothing in our acknowledged past provides a paradigm for such. Only primitive people have failed to reach our level of sophistication.

Before European colonization, certain North American cultures built sophisticated regional nations but abandoned them owing to authoritarian cruelty and destruction. They were overrun by societies that saw no wrong in perpetual exploitation. David Graeber's The Dawn of Everything is an example of historical rediscovery, which is now crucial.

From the new paradigm's perspective, the old paradigm is irrational, yet it's too easy to see those in it as ignorant or malicious, if not both. These people are both, but the collapsing paradigm they promote is older or more ingrained than we think.

We can't shift that paradigm's view of a dead world. We must eliminate this mindset from our nations' leadership. No other way will preserve the earth.

Change is occurring. As always with tremendous transition, younger people are building the new paradigm.

The old paradigm's disintegration is insane. The ability to detect errors and abandon their sources is more important than age. This is gaining recognition.

The breakdown of the previous paradigm is not due to senile leadership, but to systemic problems that the current, conservative leadership cannot recognize.

Stop following the old paradigm.

The brand-new USB Rubber Ducky is much riskier than before.

With its own programming language, the well-liked hacking tool may now pwn you.

With a vengeance, the USB Rubber Ducky is back.

This year's Def Con hacking conference saw the release of a new version of the well-liked hacking tool, and its author, Darren Kitchen, was on hand to explain it. We put a few of the new features to the test and discovered that the most recent version is riskier than ever.

WHAT IS IT?

The USB Rubber Ducky seems to the untrained eye to be an ordinary USB flash drive. However, when you connect it to a computer, the computer recognizes it as a USB keyboard and will accept keystroke commands from the device exactly like a person would type them in.

Kitchen explained to me, "It takes use of the trust model built in, where computers have been taught to trust a human, in that anything it types is trusted to the same degree as the user is trusted. And a computer is aware that clicks and keystrokes are how people generally connect with it.

Over ten years ago, the first Rubber Ducky was published, quickly becoming a hacker favorite (it was even featured in a Mr. Robot scene). Since then, there have been a number of small upgrades, but the most recent Rubber Ducky takes a giant step ahead with a number of new features that significantly increase its flexibility and capability.

WHERE IS ITS USE?

The options are nearly unlimited with the proper strategy.

The Rubber Ducky has already been used to launch attacks including making a phony Windows pop-up window to collect a user's login information or tricking Chrome into sending all saved passwords to an attacker's web server. However, these attacks lacked the adaptability to operate across platforms and had to be specifically designed for particular operating systems and software versions.

The nuances of DuckyScript 3.0 are described in a new manual. 

The most recent Rubber Ducky seeks to get around these restrictions. The DuckyScript programming language, which is used to construct the commands that the Rubber Ducky will enter into a target machine, receives a significant improvement with it. DuckyScript 3.0 is a feature-rich language that allows users to write functions, store variables, and apply logic flow controls, in contrast to earlier versions that were primarily limited to scripting keystroke sequences (i.e., if this... then that).

This implies that, for instance, the new Ducky can check to see if it is hooked into a Windows or Mac computer and then conditionally run code specific to each one, or it can disable itself if it has been attached to the incorrect target. In order to provide a more human effect, it can also generate pseudorandom numbers and utilize them to add a configurable delay between keystrokes.

The ability to steal data from a target computer by encoding it in binary code and transferring it through the signals intended to instruct a keyboard when the CapsLock or NumLock LEDs should light up is perhaps its most astounding feature. By using this technique, a hacker may plug it in for a brief period of time, excuse themselves by saying, "Sorry, I think that USB drive is faulty," and then take it away with all the credentials stored on it.

HOW SERIOUS IS THE RISK?

In other words, it may be a significant one, but because physical device access is required, the majority of people aren't at risk of being a target.

The 500 or so new Rubber Duckies that Hak5 brought to Def Con, according to Kitchen, were his company's most popular item at the convention, and they were all gone on the first day. It's safe to suppose that hundreds of hackers already possess one, and demand is likely to persist for some time.

Additionally, it has an online development toolkit that can be used to create attack payloads, compile them, and then load them onto the target device. A "payload hub" part of the website makes it simple for hackers to share what they've generated, and the Hak5 Discord is also busy with conversation and helpful advice. This makes it simple for users of the product to connect with a larger community.

It's too expensive for most individuals to distribute in volume, so unless your favorite cafe is renowned for being a hangout among vulnerable targets, it's doubtful that someone will leave a few of them there. To that end, if you intend to plug in a USB device that you discovered outside in a public area, pause to consider your decision.

WOULD IT WORK FOR ME?

Although the device is quite straightforward to use, there are a few things that could cause you trouble if you have no prior expertise writing or debugging code. For a while, during testing on a Mac, I was unable to get the Ducky to press the F4 key to activate the launchpad, but after forcing it to identify itself using an alternative Apple keyboard device ID, the problem was resolved.

From there, I was able to create a script that, when the Ducky was plugged in, would instantly run Chrome, open a new browser tab, and then immediately close it once more without requiring any action from the laptop user. Not bad for only a few hours of testing, and something that could be readily changed to perform duties other than reading technology news.