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!

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!

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.

My kids redesigned the internet because it lacks inventiveness.

Internet today is bland. Everything is generic: fonts, layouts, pages, and visual language. Microtypography is messy.

Web design today seems dictated by technical and ideological constraints rather than creativity and ideas. Text and graphics are in containers on every page. All design is assumed.

Ironically, web technologies can design a lot. We can execute most designs. We make shocking, evocative websites. Experimental typography, generating graphics, and interactive experiences are possible.

Even designer websites use containers in containers. Dribbble and Behance, the two most popular creative websites, are boring. Lead image.

How did this happen?

Several reasons. WordPress and other blogging platforms use templates. These frameworks build web pages by combining graphics, headlines, body content, and videos. Not designs, templates. These rules combine related data types. These platforms don't let users customize pages beyond the template. You filled the template.

Templates are content-neutral. Thus, the issue.

Form should reflect and shape content, which is a design principle. Separating them produces content containers. Templates have no design value.

One of the fundamental principles of design is a deep and meaningful connection between form and content.

Web design lacks imagination for many reasons. Most are pragmatic and economic. Page design takes time. Large websites lack the resources to create a page from scratch due to the speed of internet news and the frequency of new items. HTML, JavaScript, and CSS continue to challenge web designers. Web design can't match desktop publishing's straightforward operations.

Designers may also be lazy. Mobile-first, generic, framework-driven development tends to ignore web page visual and contextual integrity.

How can we overcome this? How might expressive and avant-garde websites look today?

Rediscovering the past helps design the future.

'90s-era web design

At the University of the Arts Bremen's research and development group, I created my first website 23 years ago. Web design was trendy. Young web. Pages inspired me.

We struggled with HTML in the mid-1990s. Arial, Times, and Verdana were the only web-safe fonts. Anything exciting required table layouts, monospaced fonts, or GIFs. HTML was originally content-driven, thus we had to work against it to create a page.

Experimental typography was booming. Designers challenged the established quo from Jan Tschichold's Die Neue Typographie in the twenties to April Greiman's computer-driven layouts in the eighties. By the mid-1990s, an uncommon confluence of technological and cultural breakthroughs enabled radical graphic design. Irma Boom, David Carson, Paula Scher, Neville Brody, and others showed it.

Early web pages were dull compared to graphic design's aesthetic explosion. The Web Design Museum shows this.

Nobody knew how to conduct browser-based graphic design. Web page design was undefined. No standards. No CMS (nearly), CSS, JS, video, animation.

Now is as good a time as any to challenge the internet’s visual conformity.

In 2018, everything is browser-based. Massive layouts to micro-typography, animation, and video. How do we use these great possibilities? Containerized containers. JavaScript-contaminated mobile-first pages. Visually uniform templates. Web design 23 years later would disappoint my younger self.

Our imagination, not technology, restricts web design. We're too conformist to aesthetics, economics, and expectations.

Crisis generates opportunity. Challenge online visual conformity now. I'm too old and bourgeois to develop a radical, experimental, and cutting-edge website. I can ask my students.

I taught web design at the Potsdam Interface Design Programme in 2017. Each team has to redesign a website. Create expressive, inventive visual experiences on the browser. Create with contemporary web technologies. Avoid usability, readability, and flexibility concerns. Act. Ignore Erwartungskonformität.

The class outcome pleased me. This overview page shows all results. Four diverse projects address the challenge.

1. ZKM by Frederic Haase and Jonas Köpfer

Frederic and Jonas began their experiments on the ZKM website. The ZKM is Germany's leading media art exhibition location, but its website remains conventional. It's useful but not avant-garde like the shows' art.

Frederic and Jonas designed the ZKM site's concept, aesthetic language, and technical configuration to reflect the museum's progressive approach. A generative design engine generates new layouts for each page load.

ZKM redesign.

2. Streem by Daria Thies, Bela Kurek, and Lucas Vogel

Street art magazine Streem. It promotes new artists and societal topics. Streem includes artwork, painting, photography, design, writing, and journalism. Daria, Bela, and Lucas used these influences to develop a conceptual metropolis. They designed four neighborhoods to reflect magazine sections for their prototype. For a legible city, they use powerful illustrative styles and spatial typography.

Streem makeover.

3. Medium by Amelie Kirchmeyer and Fabian Schultz

Amelie and Fabian structured. Instead of developing a form for a tale, they dissolved a web page into semantic, syntactical, and statistical aspects. HTML's flexibility was their goal. They broke Medium posts into experimental typographic space.

Medium revamp.

4. Hacker News by Fabian Dinklage and Florian Zia

Florian and Fabian made Hacker News interactive. The social networking site aggregates computer science and IT news. Its voting and debate features are extensive despite its simple style. Fabian and Florian transformed the structure into a typographic timeline and network area. News and comments sequence and connect the visuals. To read Hacker News, they connected their design to the API. Hacker News makeover.

Communication is not legibility, said Carson. Apply this to web design today. Modern websites must be legible, usable, responsive, and accessible. They shouldn't limit its visual palette. Visual and human-centered design are not stereotypes.

I want radical, generative, evocative, insightful, adequate, content-specific, and intelligent site design. I want to rediscover web design experimentation. More surprises please. I hope the web will appear different in 23 years.

Update: this essay has sparked a lively discussion! I wrote a brief response to the debate's most common points: Creativity vs. Usability