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!

In the early 2000s, I began developing SaaS. I helped launch an internet fax service that delivered faxes to email inboxes. Back then, it saved consumers money and made the procedure easier.

Google AdWords was young then. Anyone might establish a new website, spend a few hundred dollars on keywords, and see dozens of new paying clients every day. That's how we launched our new SaaS, and these clients stayed for years. Our early ROI was sky-high.

Changing times

The situation changed dramatically after 15 years. Our paid advertising cost $200-$300 for every new customer. Paid advertising takes three to four years to repay.

Fortunately, we still had tens of thousands of loyal clients. Good organic rankings gave us new business. We needed less sponsored traffic to run a profitable SaaS firm.

Is it still possible?

Since selling our internet fax firm, I've dreamed about starting a SaaS company. One I could construct as a lone developer and progressively grow a dedicated customer base, as I did before in a small team.

It seemed impossible to me. Solo startups couldn't afford paid advertising. SEO was tough. Even the worst SaaS startup ideas attracted VC funding. How could I compete with startups that could hire great talent and didn't need to make money for years (or ever)?

The One and Only Way to Learn

After years of talking myself out of SaaS startup ideas, I decided to develop and launch one. I needed to know if a solitary developer may create a SaaS app in 2022.

Thus, I did. I invented webwriter.ai, an AI-powered writing tool for website content, from hero section headlines to blog posts, this year. I soft-launched an MVP in July.

Considering the Issue

Now that I've developed my own fully capable SaaS app for site builders and developers, I wonder if it's still possible. Can webwriter.ai be successful?

I know webwriter.ai's proposal is viable because Jasper.ai and Grammarly are also AI-powered writing tools. With competition comes validation.

To Win, Differentiate

To compete with well-funded established brands, distinguish to stand out to a portion of the market. So I can speak directly to a target user, unlike larger competition.

I created webwriter.ai to help web builders and designers produce web content rapidly. This may be enough differentiation for now.

Budget-Friendly Promotion

When paid search isn't an option, we get inventive. There are more tools than ever to promote a new website.

• Organic Results

• on social media (Twitter, Instagram, TikTok, LinkedIn)

• Marketing with content that is compelling

• Link Creation

• Listings in directories

• references made in blog articles and on other websites

• Forum entries

The Beginning of the Journey

As I've labored to construct my software, I've pondered a new mantra. Not sure where that originated from, but I like it. I'll live by it and teach my kids:

“Do the work.”

5 VC investment criteria

I reviewed 200 startup business concepts last week. Brainache.

The enterprises sold various goods and services. The concepts were achingly similar: give us money, we'll produce a product, then get more to expand. No different from daily plans and pitches.

Most of those 200 plans sounded plausible. But 10% looked venture-worthy. 90% of startups need alternatives to venture finance.

With the success of VC-backed businesses and the growth of venture funds, a common misperception is that investors would fund any decent company idea. Finding investors that believe in the firm and founders is the key to funding.

Incorrect. Venture capital needs investing in certain enterprises. If your startup doesn't match the model, as most early-stage startups don't, you can revise your business plan or locate another source of capital.

Before spending six months pitching angels and VCs, make sure your startup fits these criteria.

Likely to generate $100 million in sales

First, I check the income predictions in a pitch deck. If it doesn't display $100M, don't bother.

The math doesn't work for venture financing in smaller businesses.

Say a fund invests $1 million in a startup valued at $5 million that is later acquired for $20 million. That's a win everyone should celebrate. Most VCs don't care.

Consider a $100M fund. The fund must reach $360M in 7 years with a 20% return. Only 20-30 investments are possible. 90% of the investments will fail, hence the 23 winners must return $100M-$200M apiece. $15M isn't worth the work.

Angel investors and tiny funds use the same ideas as venture funds, but their smaller scale affects the calculations. If a company can support its growth through exit on less than $2M in angel financing, it must have $25M in revenues before large companies will consider acquiring it.

Aiming for Hypergrowth

A startup's size isn't enough. It must expand fast.

Developing a great business takes time. Complex technology must be constructed and tested, a nationwide expansion must be built, or production procedures must go from lab to pilot to factories. These can be enormous, world-changing corporations, but venture investment is difficult.

The normal 10-year venture fund life. Investments are made during first 3–4 years.. 610 years pass between investment and fund dissolution. Funds need their investments to exit within 5 years, 7 at the most, therefore add a safety margin.

Longer exit times reduce ROI. A 2-fold return in a year is excellent. Loss at 2x in 7 years.

Lastly, VCs must prove success to raise their next capital. The 2nd fund is raised from 1st fund portfolio increases. Third fund is raised using 1st fund's cash return. Fund managers must raise new money quickly to keep their jobs.

Branding or technology that is protected

No big firm will buy a startup at a high price if they can produce a competing product for less. Their development teams, consumer base, and sales and marketing channels are large. Who needs you?

Patents, specialist knowledge, or brand name are the only answers. The acquirer buys this, not the thing.

I've heard of several promising startups. It's not a decent investment if there's no exit strategy.

A company that installs EV charging stations in apartments and shopping areas is an example. It's profitable, repeatable, and big. A terrific company. Not a startup.

This building company's operations aren't secret. No technology to protect, no special information competitors can't figure out, no go-to brand name. Despite the immense possibilities, a large construction company would be better off starting their own.

Most venture businesses build products, not services. Services can be profitable but hard to safeguard.

Probable purchase at high multiple

Once a software business proves its value, acquiring it is easy. Pharma and medtech firms have given up on their own research and instead acquire startups after regulatory permission. Many startups, especially in specialized areas, have this weakness.

That doesn't mean any lucrative $25M-plus business won't be acquired. In many businesses, the venture model requires a high exit premium.

A startup invents a new glue. 3M, BASF, Henkel, and others may buy them. Adding more adhesive to their catalogs won't boost commerce. They won't compete to buy the business. They'll only buy a startup at a profitable price. The acquisition price represents a moderate EBITDA multiple.

The company's $100M revenue presumably yields $10m in profits (assuming they’ve reached profitability at all). A $30M-$50M transaction is likely. Not terrible, but not what venture investors want after investing $25M to create a plant and develop the business.

Private equity buys profitable companies for a moderate profit multiple. It's a good exit for entrepreneurs, but not for investors seeking 10x or more what PE firms pay. If a startup offers private equity as an exit, the conversation is over.

Constructed for purchase

The startup wants a high-multiple exit. Unless the company targets $1B in revenue and does an IPO, exit means acquisition.

If they're constructing the business for acquisition or themselves, founders must decide.

If you want an indefinitely-running business, I applaud you. We need more long-term founders. Most successful organizations are founded around consumer demands, not venture capital's urge to grow fast and exit. Not venture funding.

if you don't match the venture model, what to do

VC funds moonshots. The 10% that succeed are extraordinary. Not every firm is a rocketship, and launching the wrong startup into space, even with money, will explode.

But just because your startup won't make $100M in 5 years doesn't mean it's a bad business. Most successful companies don't follow this model. It's not venture capital-friendly.

Although venture capital gets the most attention due to a few spectacular triumphs (and disasters), it's not the only or even most typical option to fund a firm.

Other ways to support your startup:

• Personal and family resources, such as credit cards, second mortgages, and lines of credit

• bootstrapping off of sales

• government funding and honors

• Private equity & project financing

• collaborating with a big business

• Including a business partner

Before pitching angels and VCs, be sure your startup qualifies. If so, include them in your pitch.

Without self-control, you'll waste time chasing dopamine fixes.

I found a powerful quote in Tony Robbins' Awaken The Giant Within:

“Most of the challenges that we have in our personal lives come from a short-term focus” — Tony Robbins

Most people are short-term oriented, but highly successful people are long-term oriented.

Successful people act in line with their long-term goals and values, while the rest are distracted by short-term pleasures and dopamine fixes.

Instant gratification wrecks lives

Instant pleasure is fleeting. Quickly fading effects leave you craving more stimulation.

Before you know it, you're in a cycle of quick fixes. This explains binging on food, social media, and Netflix.

These things cause a dopamine spike, which is entertaining. This dopamine spike crashes quickly, leaving you craving more stimulation.

It's fine to watch TV or play video games occasionally. Problems arise when brain impulses aren't controlled. You waste hours chasing dopamine fixes.

Instant gratification becomes problematic when it interferes with long-term goals, happiness, and life fulfillment.

Most rewarding things require delay

Life's greatest rewards require patience and delayed gratification. They must be earned through patience, consistency, and effort.

Ex:

• A fit, healthy body

• A deep connection with your spouse

• A thriving career/business

• A healthy financial situation

These are some of life's most rewarding things, but they take work and patience. They all require the ability to delay gratification.

To have a healthy bank account, you must save (and invest) a large portion of your monthly income. This means no new tech or clothes.

If you want a fit, healthy body, you must eat better and exercise three times a week. So no fast food and Netflix.

It's a battle between what you want now and what you want most.

Successful people choose what they want most over what they want now. It's a major difference.

Instant vs. delayed gratification

Most people subconsciously prefer instant rewards over future rewards, even if the future rewards are more significant.

We humans aren't logical. Emotions and instincts drive us. So we act against our goals and values.

Fortunately, instant gratification bias can be overridden. This is a modern superpower. Effective methods include:

#1: Train your brain to handle overstimulation

Training your brain to function without constant stimulation is a powerful change. Boredom can lead to long-term rewards.

Unlike impulsive shopping, saving money is boring. Having lots of cash is amazing.

Compared to video games, deep work is boring. A successful online business is rewarding.

Reading books is boring compared to scrolling through funny videos on social media. Knowledge is invaluable.

You can't do these things if your brain is overstimulated. Your impulses will control you. To reduce overstimulation addiction, try:

• Daily meditation (10 minutes is enough)

• Daily study/work for 90 minutes (no distractions allowed)

• First hour of the day without phone, social media, and Netflix

• Nature walks, journaling, reading, sports, etc.

#2: Make Important Activities Less Intimidating

Instant gratification helps us cope with stress. Starting a book or business can be intimidating. Video games and social media offer a quick escape in such situations.

Make intimidating tasks less so. Break them down into small tasks. Start a new business/side-hustle by:

• Get domain name

• Design website

• Write out a business plan

• Research competition/peers

• Approach first potential client

Instead of one big mountain, divide it into smaller sub-tasks. This makes a task easier and less intimidating.

#3: Plan ahead for important activities

Distractions will invade unplanned time. Your time is dictated by your impulses, which are usually Netflix, social media, fast food, and video games. It wants quick rewards and dopamine fixes.

Plan your days and be proactive with your time. Studies show that scheduling activities makes you 3x more likely to do them.

To achieve big goals, you must plan. Don't gamble.

Want to get fit? Schedule next week's workouts. Want a side-job? Schedule your work time.

Few sentences can have global significance.

Ethan Zuckerman invented the pop-up commercial in 1997.

He was working for Tripod.com, an online service that let people make little web pages for free. Tripod offered advertising to make money. Advertisers didn't enjoy seeing their advertising next to filthy content, like a user's anal sex website.

Zuckerman's boss wanted a solution. Wasn't there a way to move the ads away from user-generated content?

When you visited a Tripod page, a pop-up ad page appeared. So, the ad isn't officially tied to any user page. It'd float onscreen.

Here’s the thing, though: Zuckerman’s bit of Javascript, that created the popup ad? It was incredibly short — a single line of code:

window.open('http://tripod.com/navbar.html'
"width=200, height=400, toolbar=no, scrollbars=no, resizable=no, target=_top");

Javascript tells the browser to open a 200-by-400-pixel window on top of any other open web pages, without a scrollbar or toolbar.

Simple yet harmful! Soon, commercial websites mimicked Zuckerman's concept, infesting the Internet with pop-up advertising. In the early 2000s, a coder for a download site told me that most of their revenue came from porn pop-up ads.

Pop-up advertising are everywhere. You despise them. Hopefully, your browser blocks them.

Zuckerman wrote a single line of code that made the world worse.

I read Zuckerman's story in How 26 Lines of Code Changed the World. Torie Bosch compiled a humorous anthology of short writings about code that tipped the world.

Most of these samples are quite short. Pop-cultural preconceptions about coding say that important code is vast and expansive. Hollywood depicts programmers as blurs spouting out Niagaras of code. Google's success was formerly attributed to its 2 billion lines of code.

It's usually not true. Google's original breakthrough, the piece of code that propelled Google above its search-engine counterparts, was its PageRank algorithm, which determined a web page's value based on how many other pages connected to it and the quality of those connecting pages. People have written their own Python versions; it's only a few dozen lines.

Google's operations, like any large tech company's, comprise thousands of procedures. So their code base grows. The most impactful code can be brief.

The examples are fascinating and wide-ranging, so read the whole book (or give it to nerds as a present). Charlton McIlwain wrote a chapter on the police beat algorithm developed in the late 1960s to anticipate crime hotspots so law enforcement could dispatch more officers there. It created a racial feedback loop. Since poor Black neighborhoods were already overpoliced compared to white ones, the algorithm directed more policing there, resulting in more arrests, which convinced it to send more police; rinse and repeat.

Kelly Chudler's You Are Not Expected To Understand This depicts the police-beat algorithm.

Even shorter code changed the world: the tracking pixel.

Lily Hay Newman's chapter on monitoring pixels says you probably interact with this code every day. It's a snippet of HTML that embeds a single tiny pixel in an email. Getting an email with a tracking code spies on me. As follows: My browser requests the single-pixel image as soon as I open the mail. My email sender checks to see if Clives browser has requested that pixel. My email sender can tell when I open it.

Adding a tracking pixel to an email is easy:

<img src="URL LINKING TO THE PIXEL ONLINE" width="0" height="0">

An older example: Ellen R. Stofan and Nick Partridge wrote a chapter on Apollo 11's lunar module bailout code. This bailout code operated on the lunar module's tiny on-board computer and was designed to prioritize: If the computer grew overloaded, it would discard all but the most vital work.

When the lunar module approached the moon, the computer became overloaded. The bailout code shut down anything non-essential to landing the module. It shut down certain lunar module display systems, scaring the astronauts. Module landed safely.

22-line code

POODOO    INHINT
    CA  Q
    TS  ALMCADR

    TC  BANKCALL
    CADR  VAC5STOR  # STORE ERASABLES FOR DEBUGGING PURPOSES.

    INDEX  ALMCADR
    CAF  0
ABORT2    TC  BORTENT

OCT77770  OCT  77770    # DONT MOVE
    CA  V37FLBIT  # IS AVERAGE G ON
    MASK  FLAGWRD7
    CCS  A
    TC  WHIMPER -1  # YES.  DONT DO POODOO.  DO BAILOUT.

    TC  DOWNFLAG
    ADRES  STATEFLG

    TC  DOWNFLAG
    ADRES  REINTFLG

    TC  DOWNFLAG
    ADRES  NODOFLAG

    TC  BANKCALL
    CADR  MR.KLEAN
    TC  WHIMPER

This fun book is worth reading.

I'm a contributor to the New York Times Magazine, Wired, and Mother Jones. I've also written Coders: The Making of a New Tribe and the Remaking of the World and Smarter Than You Think: How Technology is Changing Our Minds. Twitter and Instagram: @pomeranian99; Mastodon: @clive@saturation.social.