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!

Know why it's important.

The entrepreneur I was meeting with said, "I should be doing crypto, or maybe AI? Aren't those the hot spots? I should look there for a startup idea.”

I shook my head. Yes, they're exciting, but that doesn't mean they're best for you and your business.

“There are different types of entrepreneurs?” he asked.

I said "obviously." Two types, actually. Knowing what type of entrepreneur you are helps you build the right startup.

The two types of businesspeople

The best way for me to describe the two types of entrepreneurs is to start by telling you exactly the kinds of entrepreneurial opportunities I never get excited about: future opportunities.

In the early 1990s, my older brother showed me the World Wide Web and urged me to use it. Unimpressed, I returned to my Super Nintendo.

My roommate tried to get me to join Facebook as a senior in college. I remember thinking, This is dumb. Who'll use it?

In 2011, my best friend tried to convince me to buy bitcoin and I laughed.

Heck, a couple of years ago I had to buy a new car, and I never even considered buying something that didn’t require fossilized dinosaur bones.

I'm no visionary. I don't anticipate the future. I focus on the present.

This tendency makes me a problem-solving entrepreneur. I identify entrepreneurial opportunities by spotting flaws and/or inefficiencies in the world and devising solutions.

There are other ways to find business opportunities. Visionary entrepreneurs also exist. I don't mean visionary in the hyperbolic sense that implies world-changing impact. I mean visionary as an entrepreneur who identifies future technological shifts that will change how people work and live and create new markets.

Problem-solving and visionary entrepreneurs are equally good. But the two approaches to building companies are very different. Knowing the type of entrepreneur you are will help you build a startup that fits your worldview.

What is the distinction?

Let's use some simple hypotheticals to compare problem-solving and visionary entrepreneurship.

Imagine a city office building without nearby restaurants. Those office workers love to eat. Sometimes they'd rather eat out than pack a lunch. As an entrepreneur, you can solve the lack of nearby restaurants. You'd open a restaurant near that office, say a pizza parlor, and get customers because you solved the lack of nearby restaurants. Problem-solving entrepreneurship.

Imagine a new office building in a developing area with no residents or workers. In this scenario, a large office building is coming. The workers will need to eat then. As a visionary entrepreneur, you're excited about the new market and decide to open a pizzeria near the construction to meet demand.

Both possibilities involve the same product. You opened a pizzeria. How you launched that pizza restaurant and what will affect its success are different.

Why is the distinction important?

Let's say you opened a pizzeria near an office. You'll probably get customers. Because people are nearby and demand isn't being met, someone from a nearby building will stop in within the first few days of your pizzeria's grand opening. This makes solving the problem relatively risk-free. You'll get customers unless you're a fool.

The market you're targeting existed before you entered it, so you're not guaranteed success. This means people in that market solved the lack of nearby restaurants. Those office workers are used to bringing their own lunches. Why should your restaurant change their habits? Even when they eat out, they're used to traveling far. They've likely developed pizza preferences.

To be successful with your problem-solving startup, you must convince consumers to change their behavior, which is difficult.

Unlike opening a pizza restaurant near a construction site. Once the building opens, workers won't have many preferences or standardized food-getting practices. Your pizza restaurant can become the incumbent quickly. You'll be the first restaurant in the area, so you'll gain a devoted following that makes your food a routine.

Great, right? It's easier than changing people's behavior. The benefit comes with a risk. Opening a pizza restaurant near a construction site increases future risk. What if builders run out of money? No one moves in? What if the building's occupants are the National Association of Pizza Haters? Then you've opened a pizza restaurant next to pizza haters.

Which kind of businessperson are you?

This isn't to say one type of entrepreneur is better than another. Each type of entrepreneurship requires different skills.

As my simple examples show, a problem-solving entrepreneur must operate in markets with established behaviors and habits. To be successful, you must be able to teach a market a new way of doing things.

Conversely, the challenge of being a visionary entrepreneur is that you have to be good at predicting the future and getting in front of that future before other people.

Both are difficult in different ways. So, smart entrepreneurs don't just chase opportunities. Smart entrepreneurs pursue opportunities that match their skill sets.

I've worked in a People role at seven early-stage firms for over 15 years (I enjoy chasing a dream!). Few of the seven achieved profitability, including unicorn status or acquisition.

Did early-stage startups share anything? Was there a difference between winners and losers? YES.

I support founders and entrepreneurs building financially sustainable enterprises with a compelling cause. This isn't something everyone would do. A company's success demands more than guts. Founders drive startup success.

Six Qualities of Successful Startups

Successful startup founders either innately grasped the correlation between strong team engagement and a well-executed business model, or they knew how to ask and listen to others (executive coaches, other company leaders, the team itself) to learn about it.

Successful startups:

1. Co-founders agreed and got along personally.

Multi-founder startups are common. When co-founders agree on strategic decisions and are buddies, there's less friction and politics at work.

As a co-founder, ask your team if you're aligned. They'll explain.

I've seen C-level leaders harbor personal resentments over disagreements. A co-departure founder's caused volatile leadership and work disruptions that the team struggled to manage during and after.

2. Team stayed.

Successful startups have low turnover. Nobody is leaving. There may be a termination for performance, but other team members will have observed the issues and agreed with the decision.

You don't want organizational turnover of 30%+, with leaders citing performance issues but the team not believing them. This breeds suspicion.

Something is wrong if many employees leave voluntarily or involuntarily. You may hear about lack of empowerment, support, or toxic leadership in exit interviews and from the existing team. Intellectual capital loss and resource instability harm success.

3. Team momentum.

A successful startup's team is excited about its progress. Consistently achieving goals and having trackable performance metrics. Some describe this period of productivity as magical, with great talents joining the team and the right people in the right places. Increasing momentum.

I've also seen short-sighted decisions where only some departments, like sales and engineering, had goals. Lack of a unified goals system created silos and miscommunication. Some employees felt apathetic because they didn't know how they contributed to team goals.

4. Employees advanced in their careers.

Even if you haven't created career pathing or professional development programs, early-stage employees will grow and move into next-level roles. If you hire more experienced talent and leaders, expect them to mentor existing team members. Growing companies need good performers.

New talent shouldn't replace and discard existing talent. This creates animosity and makes existing employees feel unappreciated for their early contributions to the company.

5. The company lived its values.

Culture and identity are built on lived values. A company's values affect hiring, performance management, rewards, and other processes. Identify, practice, and believe in company values. Starting with team values instead of management or consultants helps achieve this. When a company's words and actions match, it builds trust.

When company values are beautifully displayed on a wall but few employees understand them, the opposite is true. If an employee can't name the company values, they're useless.

6. Communication was clear.

When necessary information is shared with the team, they feel included, trusted, and like owners. Transparency means employees have the needed information to do their jobs. Disclosure builds trust. The founders answer employees' questions honestly.

Information accessibility decreases office politics. Without transparency, even basic information is guarded and many decisions are made in secret. I've seen founders who don't share financial, board meeting, or compensation and equity information. The founders' lack of trust in the team wasn't surprising, so it was reciprocated.

The Choices

Finally. All six of the above traits (leadership alignment, minimal turnover, momentum, professional advancement, values, and transparency) were high in the profitable startups I've worked at, including unicorn status or acquisition.

I've seen these as the most common and constant signals of startup success or failure.

These characteristics are the product of founders' choices. These decisions lead to increased team engagement and business execution.

Here's something to consider for startup employees and want-to-bes. 90% of startups fail, despite the allure of building something new and gaining ownership. With the emotional and time investment in startup formation, look for startups with these traits to reduce your risk.

Both you and the startup will thrive in these workplaces.

4 Pricey Tools That Are Valuable

I pay based on ROI (return on investment).

If a $20/month tool or $500 online course doubles my return, I'm in.

Investing helps me build wealth.

Canva Pro

I initially refused to pay.

My course content needed updating a few months ago. My Google Docs text looked cleaner and more professional in Canva.

I've used it to:

• product cover pages

• eBook covers

• Product page infographics

See my Google Sheets vs. Canva product page graph.

Google Sheets vs Canva

Yesterday, I used it to make a LinkedIn video thumbnail. It took less than 5 minutes and improved my video.

In 30 hours, the video had 39,000 views.

Here's more.

HypeFury

Hypefury rocks!

It builds my brand as I sleep. What else?

Because I'm traveling this weekend, I planned tweets for 10 days. It took me 80 minutes.

So while I travel or am absent, my content mill keeps producing.

Also I like:

• I can reach hundreds of people thanks to auto-DMs. I utilize it to advertise freebies; for instance, leave an emoji remark to receive my checklist. And they automatically receive a message in their DM.

• Scheduled Retweets: By appearing in a different time zone, they give my tweet a second chance.

It helps me save time and expand my following, so that's my favorite part.

It’s also super neat:

Zoom Pro

My course involves weekly and monthly calls for alumni.

Google Meet isn't great for group calls. The interface isn't great.

Zoom Pro is expensive, and the monthly payments suck, but it's necessary.

It gives my students a smooth experience.

Previously, we'd do 40-minute meetings and then reconvene.

Zoom's free edition limits group calls to 40 minutes.

This wouldn't be a good online course if I paid hundreds of dollars.

So I felt obligated to help.

YouTube Premium

My laptop has an ad blocker.

I bought an iPad recently.

When you're self-employed and work from home, the line between the two blurs. My bed is only 5 steps away!

When I read or watched videos on my laptop, I'd slide into work mode. Only option was to view on phone, which is awkward.

YouTube premium handles it. No more advertisements and I can listen on the move.

3 Expensive Tools That Aren't Valuable

Marketing strategies are sometimes aimed to make you feel you need 38474 cool features when you don’t.

Certain tools are useless.

I found it useless.

Depending on your needs. As a writer and creator, I get no return.

They could for other jobs.

Shield Analytics

It tracks LinkedIn stats, like:

• follower growth

• trend chart for impressions

• Engagement, views, and comment stats for posts

• and much more.

Middle-tier creator costs $12/month.

I got a 25% off coupon but canceled my free trial before writing this. It's not worth the discount.

Why?

LinkedIn provides free analytics. See:

Not thorough and won't show top posts.

I don't need to see my top posts because I love experimenting with writing.

Slack Premium

Slack was my classroom. Slack provided me a premium trial during the prior cohort.

I skipped it.

Sure, voice notes are better than a big paragraph. I didn't require pro features.

Marketing methods sometimes make you think you need 38474 amazing features. Don’t fall for it.

Calendly Pro

This may be worth it if you get many calls.

I avoid calls. During my 9-5, I had too many pointless calls.

I don't need:

• ability to schedule calls for 15, 30, or 60 minutes: I just distribute each link separately.

• I have a Gumroad consultation page with a payment option.

• follow-up emails: I hardly ever make calls, so

• I just use one calendar, therefore I link to various calendars.

I'll admit, the integrations are cool. Not for me.

If you're a coach or consultant, the features may be helpful. Or book meetings.

Conclusion

Investing is spending to make money.

Use my technique — put money in tools that help you make money. This separates it from being an investment instead of an expense.

Try free versions of these tools before buying them since everyone else is.

Late in 2018, I published my first Medium article, but I didn't start writing seriously until 2019. Since then, I've written more than 240 articles, earned over $50,000 through Medium's Partner Program, and had over 2.5 million page views.

Write A Lot

Most people don't have the patience and persistence for this simple writing secret:

Write + Write + Write = possible success

Writing more improves your skills.

The more articles you publish, the more likely one will go viral.

If you only publish once a month, you have no views. If you publish 10 or 20 articles a month, your success odds increase 10- or 20-fold.

Tim Denning, Ayodeji Awosika, Megan Holstein, and Zulie Rane. Medium is their jam. How are these authors alike? They're productive and consistent. They're prolific.

80% is publishable

Many writers battle perfectionism. 

To succeed as a writer, you must publish often. You'll never publish if you aim for perfection.

Adopt the 80 percent-is-good-enough mindset to publish more. It sounds terrible, but it'll boost your writing success.

Your work won't be perfect. Always improve. Waiting for perfection before publishing will take a long time.

Second, readers are your true critics, not you. What you consider "not perfect" may be life-changing for the reader. Don't let perfectionism hinder the reader.

Don't let perfectionism hinder the reader. ou don't want to publish mediocre articles. When the article is 80% done, publish it. Don't spend hours editing. Realize it. Get feedback. Only this will work.

Make Your Headline Irresistible

We all judge books by their covers, despite the saying. And headlines. Readers, including yourself, judge articles by their titles. We use it to decide if an article is worth reading.

Make your headlines irresistible. Want more article views? Then, whether you like it or not, write an attractive article title.

Many high-quality articles are collecting dust because of dull, vague headlines. It didn't make the reader click.

As a writer, you must do more than produce quality content. You must also make people click on your article. This is a writer's job. How to create irresistible headlines:

Curiosity makes readers click. Here's a tempting example...

• Example: What Women Actually Look For in a Guy, According to a Huge Study by Luba Sigaud

Use Numbers: Click-bait lists. I mean, which article would you click first? ‘Some ways to improve your productivity’ or ’17 ways to improve your productivity.’ Which would I click?

• Example: 9 Uncomfortable Truths You Should Accept Early in Life by Sinem Günel

Most headlines are dull. If you want clicks, get 'sexy'. Buzzword-ify. Invoke emotion. Trendy words.

• Example: 20 Realistic Micro-Habits To Live Better Every Day by Amardeep Parmar

Concise paragraphs

Our culture lacks focus. If your headline gets a click, keep paragraphs short to keep readers' attention.

Some writers use 6–8 lines per paragraph, but I prefer 3–4. Longer paragraphs lose readers' interest.

A writer should help the reader finish an article, in my opinion. I consider it a job requirement. You can't force readers to finish an article, but you can make it 'snackable'

Help readers finish an article with concise paragraphs, interesting subheadings, exciting images, clever formatting, or bold attention grabbers.

Work And Move On

I've learned over the years not to get too attached to my articles. Many writers report a strange phenomenon:

The articles you're most excited about usually bomb, while the ones you're not tend to do well.

This isn't always true, but I've noticed it in my own writing. My hopes for an article usually make it worse. The more objective I am, the better an article does.

Let go of a finished article. 40 or 40,000 views, whatever. Now let the article do its job. Onward. Next story. Start another project.

Disregard Haters

Online content creators will encounter haters, whether on YouTube, Instagram, or Medium. More views equal more haters. Fun, right?

As a web content creator, I learned:

Don't debate haters. Never.

It's a mistake I've made several times. It's tempting to prove haters wrong, but they'll always find a way to be 'right'. Your response is their fuel.

I smile and ignore hateful comments. I'm indifferent. I won't enter a negative environment. I have goals, money, and a life to build. "I'm not paid to argue," Drake once said.

Use Grammarly

Grammarly saves me as a non-native English speaker. You know Grammarly. It shows writing errors and makes article suggestions.

As a writer, you need Grammarly. I have a paid plan, but their free version works. It improved my writing greatly.

Put The Reader First, Not Yourself

Many writers write for themselves. They focus on themselves rather than the reader.

Ask yourself:

This article teaches what? How can they be entertained or educated?

Personal examples and experiences improve writing quality. Don't focus on yourself.

It's not about you, the content creator. Reader-focused. Putting the reader first will change things.

Extreme ownership: Stop blaming others

I remember writing a lot on Medium but not getting many views. I blamed Medium first. Poor algorithm. Poor publishing. All sucked.

Instead of looking at what I could do better, I blamed others.

When you blame others, you lose power. Owning your results gives you power.

As a content creator, you must take full responsibility. Extreme ownership means 100% responsibility for work and results.

You don’t blame others. You don't blame the economy, president, platform, founders, or audience. Instead, you look for ways to improve. Few people can do this.

Blaming is useless. Zero. Taking ownership of your work and results will help you progress. It makes you smarter, better, and stronger.

Instead of blaming others, you'll learn writing, marketing, copywriting, content creation, productivity, and other skills. Game-changer.