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.”

Could this happen?

Medium isn't like other social media giants. It wasn't a dot-com startup that became a multi-trillion-dollar social media firm. It launched in 2012 but didn't gain popularity until later. Now, it's one of the largest sites by web traffic, but it's still little compared to most. Most of Medium's traffic is external, but they don't run advertisements, so it's all about memberships.

Medium isn't profitable, but they don't disclose how terrible the problem is. Most of the $163 million they raised has been spent or used for acquisitions. If the money turns off, Medium can't stop paying its writers since the site dies. Writers must be paid, but they can't substantially slash payment without hurting the platform. The existing model needs scale to be viable and has a low ceiling. Facebook and other free social media platforms are struggling to retain users. Here, you must pay to appreciate it, and it's bad for writers AND readers. If I had the same Medium stats on YouTube, I'd make thousands of dollars a month.

Then what? Medium has tried to monetize by offering writers a cut of new members, but that's unsustainable. People-based growth is limited. Imagine recruiting non-Facebook users and getting them to pay to join. Some may, but I'd rather write.

Alternatives:

• Donation buttons

• Tiered subscriptions ($5, $10, $25, etc.)

• Expanding content

and these may be short-term fixes, but they're not as profitable as allowing ads. Advertisements can pay several dollars per click and cents every view. If you get 40,000 views a month like me, that's several thousand instead of a few hundred. Also, Medium would have enough money to split ad revenue with writers, who would make more. I'm among the top 6% of Medium writers. Only 6% of Medium writers make more than $100, and I made $500 with 35,000 views last month. Compared to YouTube, the top 1% of Medium authors make a lot. Mr. Beast and PewDiePie make MILLIONS a month, yet top Medium writers make tens of thousands. Sure, paying 3 or 4 people a few grand, or perhaps tens of thousands, will keep them around. What if great authors leveraged their following to go huge on YouTube and abandoned Medium? If people use Medium to get successful on other platforms, Medium will be continuously cycling through authors and paying them to stay.

Ads might make writing on Medium more profitable than making videos on YouTube because they could preserve the present freemium model and pay users based on internal views. The $5 might be ad-free.

Consider: Would you accept Medium ads? A $5 ad-free version + pay-as-you-go, etc. What are your thoughts on this?

Original post available here

The holy grail of plain text task management is finally within reach

Plain text task management? Are you serious?? Dedicated task managers exist for a reason, you know. Sheesh.

—Oh, I know. Believe me, I know! But hear me out.

I've managed projects and tasks in plain text for more than four years. Since reorganizing my to-do list, plain text task management is within reach.

Data completely yours? One billion percent. Beef it up with coding? Be my guest.

Enter: The List

The answer? A list. That’s it!

Write down tasks. Obsidian, Notenik, Drafts, or iA Writer are good plain text note-taking apps.

List too long? Of course, it is! A large list tells you what to do. Feel the itch and friction. Then fix it.

• But I want to be able to distinguish between work and personal life! List two things.

• However, I need to know what should be completed first. Put those items at the top.

• However, some things keep coming up, and I need to be reminded of them! Put those in your calendar and make an alarm for them.

• But since individual X hasn't completed task Y, I can't proceed with this. Create a Waiting section on your list by dividing it.

• But I must know what I'm supposed to be doing right now! Read your list(s). Check your calendar. Think critically.

Before I begin a new one, I remind myself that "Listory Never Repeats."

There’s no such thing as too many lists if all are needed. There is such a thing as too many lists if you make them before they’re needed. Before they complain that their previous room was small or too crowded or needed a new light.

A list that feels too long has a voice; it’s telling you what to do next.

I use one Master List. It's a control panel that tells me what to focus on short-term. If something doesn't need semi-immediate attention, it goes on my Backlog list.

Todd Lewandowski's DWTS (Done, Waiting, Top 3, Soon) performance deserves praise. His DWTS to-do list structure has transformed my plain-text task management. I didn't realize it was upside down.

This is my take on it:

D = Done

Move finished items here. If they pile up, clear them out every week or month. I have a Done Archive folder.

W = Waiting

Things seething in the background, awaiting action. Stir them occasionally so they don't burn.

T = Top 3

Three priorities. Personal comes first, then work. There will always be a top 3 (no more than 5) in every category. Projects, not chores, usually.

S = Soon

This part is action-oriented. It's for anything you can accomplish to finish one of the Top 3. This collection includes thoughts and project lists. The sole requirement is that they should be short-term goals.

Some of you have probably concluded this isn't for you. Please read Todd's piece before throwing out the baby. Often. You shouldn't miss a newborn.

As much as Dancing With The Stars helps me recall this method, I may try switching their order. TSWD; Drilling Tunnel Seismic? Serenity After Task?

Master List Showcase

My Master List lives alone in its own file, but sometimes appears in other places.  It's included in my Weekly List template. Here's a (soon-to-be-updated) demo vault of my Obsidian planning setup to download for free.

Here's the code behind my weekly screenshot:

## [[Master List - 2022|✓]]  TO DO

![[Master List - 2022]]

FYI, I use the Minimal Theme in Obsidian, with a few tweaks.

You may note I'm utilizing a checkmark as a link. For me, that's easier than locating the proper spot to click on the embed.

Blue headings for Done and Waiting are links. Done links to the Done Archive page and Waiting to a general waiting page.

Read my full article here.

Offices without books are like bodies without souls.

After 10 years, my CEO sold his company for $30 million. I've shared many of his lessons on medium. You could ask him anything at his always-open office. He also said we could use his office for meetings while he was away. When I used his office for work, I was always struck by how many books he had.

Books are useful in almost every aspect of learning. Building a business, improving family relationships, learning a new language, a new skill... Books teach, guide, and structure. Whether fiction or nonfiction, books inspire, give ideas, and develop critical thinking skills.

My CEO prefers non-fiction and attends a Friday book club. This article discusses 5 books I found in his office that impacted my life/business. My CEO sold his company for $30 million, but I've built a steady business through blogging and video making.

I recall events and lessons I learned from my CEO and how they relate to each book, and I explain how I applied the book's lessons to my business and life.

Note: This post has no affiliate links.

1. The One Thing — Gary Keller

Gary Keller, a real estate agent, wanted more customers. So he and his team brainstormed ways to get more customers. They decided to write a bestseller about work and productivity. The more people who saw the book, the more customers they'd get.

Gary Keller focused on writing the best book on productivity, work, and efficiency for months. His business experience. Keller's business grew after the book's release.

The author summarizes the book in one question.

"What's the one thing that will make everything else easier or unnecessary?"

When I started my blog and business alongside my 9–5, I quickly identified my one thing: writing. My business relied on it, so it had to be great. Without writing, there was no content, traffic, or business.

My CEO focused on funding when he started his business. Even in his final years, he spent a lot of time on the phone with investors, either to get more money or to explain what he was doing with it. My CEO's top concern was money, and the other super important factors were handled by separate teams.

• Product tech and design

• Incredible customer support team

• Excellent promotion team

• Profitable sales team

My CEO didn't always focus on one thing and ignore the rest. He was on all of those teams when I started my job. He'd start his day in tech, have lunch with marketing, and then work in sales. He was in his office on the phone at night.

He eventually realized his errors. Investors told him he couldn't do everything for the company. If needed, he had to change internally. He learned to let go, mind his own business, and focus for the next four years. Then he sold for $30 million.

The bigger your project/company/idea, the more you'll need to delegate to stay laser-focused. I started something new every few months for 10 years before realizing this. So much to do makes it easy to avoid progress. Once you identify the most important aspect of your project and enlist others' help, you'll be successful.

2. Eat That Frog — Brian Tracy

The author quote sums up book's essence:

Mark Twain said that if you eat a live frog in the morning, it's probably the worst thing that will happen to you all day. Your "frog" is the biggest, most important task you're most likely to procrastinate on.

"Frog" and "One Thing" are both about focusing on what's most important. Eat That Frog recommends doing the most important task first thing in the morning.

I shared my CEO's calendar in an article 10 months ago. Like this:

CEO's average week (some information crossed out for confidentiality)

Notice anything about 8am-8:45am? Almost every day is the same (except Friday). My CEO started his day with a management check-in for 2 reasons:

• Checking in with all managers is cognitively demanding, and my CEO is a morning person.

• In a young startup where everyone is busy, the morning management check-in was crucial. After 10 am, you couldn't gather all managers.

When I started my blog, writing was my passion. I'm a morning person, so I woke up at 6 am and started writing by 6:30 am every day for a year. This allowed me to publish 3 articles a week for 52 weeks to build my blog and audience. After 2 years, I'm not stopping.

3. Deep Work — Cal Newport

Deep work is focusing on a cognitively demanding task without distractions (like a morning management meeting). It helps you master complex information quickly and produce better results faster. In a competitive world 10 or 20 years ago, focus wasn't a huge advantage. Smartphones, emails, and social media made focus a rare, valuable skill.

Most people can't focus anymore. Screens light up, notifications buzz, emails arrive, Instagram feeds... Many people don't realize they're interrupted because it's become part of their normal workflow.

Cal Newport mentions Bill Gates' "Think Weeks" in Deep Work.

Microsoft CEO Bill Gates would isolate himself (often in a lakeside cottage) twice a year to read and think big thoughts.

Inside Bill's Brain on Netflix shows Newport's lakeside cottage. I've always wanted a lakeside cabin to work in. My CEO bought a lakehouse after selling his company, but now he's retired.

As a company grows, you can focus less on it. In a previous section, I said investors told my CEO to get back to basics and stop micromanaging. My CEO's commitment and ability to get work done helped save the company. His deep work and new frameworks helped us survive the corona crisis (more on this later).

The ability to deep work will be a huge competitive advantage in the next century. Those who learn to work deeply will likely be successful while everyone else is glued to their screens, Bluetooth-synced to their watches, and playing Candy Crush on their tablets.

4. The 7 Habits of Highly Effective People — Stephen R. Covey

It took me a while to start reading this book because it seemed like another shallow self-help bible. I kept finding this book when researching self-improvement. I tried it because it was everywhere.

Stephen Covey taught me 2 years ago to have a personal mission statement.

A 7 Habits mission statement describes the life you want to lead, the character traits you want to embody, and the impact you want to have on others. shortform.com

I've had many lunches with my CEO and talked about Vipassana meditation and Sunday forest runs, but I've never seen his mission statement. I'm sure his family is important, though. In the above calendar screenshot, you can see he always included family events (in green) so we could all see those time slots. We couldn't book him then. Although he never spent as much time with his family as he wanted, he always made sure to be on time for his kid's birthday rather than a conference call.

My CEO emphasized his company's mission. Your mission statement should answer 3 questions.

• What does your company do?

• How does it do it?

• Why does your company do it?

As a graphic designer, I had to create mission-statement posters. My CEO hung posters in each office.

5. Measure What Matters — John Doerr

This book is about Andrew Grove's OKR strategy, developed in 1968. When he joined Google's early investors board, he introduced it to Larry Page and Sergey Brin. Google still uses OKR.

Objective Key Results

• Objective: It explains your goals and desired outcome. When one goal is reached, another replaces it. OKR objectives aren't technical, measured, or numerical. They must be clear.

• Key Result should be precise, technical, and measurable, unlike the Objective. It shows if the Goal is being worked on. Time-bound results are quarterly or yearly.

Our company almost sank several times. Sales goals were missed, management failed, and bad decisions were made. On a Monday, our CEO announced we'd implement OKR to revamp our processes.

This was a year before the pandemic, and I'm certain we wouldn't have sold millions or survived without this change. This book impacted the company the most, not just management but all levels. Organization and transparency improved. We reached realistic goals. Happy investors. We used the online tool Gtmhub to implement OKR across the organization.

My CEO's company went from near bankruptcy to being acquired for $30 million in 2 years after implementing OKR.

I hope you enjoyed this booklist. Here's a recap of the 5 books and the lessons I learned from each.

1. The 7 Habits of Highly Effective People — Stephen R. Covey

Have a mission statement that outlines your goals, character traits, and impact on others.

1. Deep Work — Cal Newport

Focus is a rare skill; master it. Deep workers will succeed in our hyper-connected, distracted world.

1. The One Thing — Gary Keller

What can you do that will make everything else easier or unnecessary? Once you've identified it, focus on it.

1. Eat That Frog — Brian Tracy

Identify your most important task the night before and do it first thing in the morning. You'll have a lighter day.

1. Measure What Matters — John Doerr

On a timeline, divide each long-term goal into chunks. Divide those slices into daily tasks (your goals). Time-bound results are quarterly or yearly. Objectives aren't measured or numbered.

Thanks for reading. Enjoy the ride!

Don't overcomplicate to-do lists. DWTS (Done, Waiting, Top 3, Soon) organizes your to-dos.

How Are You Going to Manage Everything?

Modern America is busy. Work involves meetings. Anytime, Slack communications arrive. Many software solutions offer a @-mention notification capability. Emails.

Work obligations continue. At home, there are friends, family, bills, chores, and fun things.

How are you going to keep track of it all? Enter the todo list. It’s been around forever. It’s likely to stay forever in some way, shape, or form.

Everybody has their own system. You probably modified something from middle school. Post-its? Maybe it’s an app? Maybe both, another system, or none.

I suggest a format that has worked for me in 15 years of professional and personal life.

Try it out and see if it works for you. If not, no worries. You do you! Hopefully though you can learn a thing or two, and I from you too.

It is merely a Google Doc, yes.

It's a giant list. One task per line. Indent subtasks on a new line. Add or move new tasks as needed.

I recommend using Google Docs. It's easy to use and flexible for structuring.

Prioritizing these tasks is key. I organize them using DWTS (Done, Waiting, Top 3, Soon). Chronologically is good because it implicitly provides both a priority (high, medium, low) and an ETA (now, soon, later).

Yes, I recognize the similarities to DWTS (Dancing With The Stars) TV Show. Although I'm not a fan, it's entertaining. The acronym is easy to remember and adds fun to something dull.

What each section contains

Done

All tasks' endpoint. Finish here. Don't worry about it again.

Waiting

You're blocked and can't continue. Blocked tasks usually need someone. Write Person Task so you know who's waiting.

Blocking tasks shouldn't last long. After a while, remind them kindly. If people don't help you out of kindness, they will if you're persistent.

Top 3

Mental focus areas. These can be short- to mid-term goals or recent accomplishments. 2 to 5 is a good number to stay focused.

Top 3 reminds us to prioritize. If they don't fit your Top 3 goals, delay them.

Every 1:1 at work is a project update. Another chance to list your top 3. You should know your Top 3 well and be able to discuss them confidently.

Soon

Here's your short-term to-do list. Rank them from highest to lowest.

I usually subdivide it with empty lines. First is what I have to do today, then week, then month. Subsections can be arranged however you like.

Inventories by Concept

Tasks that aren’t in your short or medium future go into the backlog. 
Eventually you’ll complete these tasks, assign them to someone else, or mark them as “wont’ do” (like done but in another sense).

Backlog tasks don't need to be organized chronologically because their timing and priority may change. Theme-organize them. When planning/strategic, you can choose themes to focus on, so future top 3 topics.

More Tips on Todos

Decide Upon a Morning Goal

Morning routines are universal. Coffee and Wordle. My to-do list is next. Two things:

• As needed, update the to-do list: based on the events of yesterday and any fresh priorities.

• Pick a few jobs to complete today: Pick a few goals that you know you can complete today. Push the remainder below and move them to the top of the Soon section. I typically select a few tasks I am confident I can complete along with one stretch task that might extend into tomorrow.

Finally. By setting and achieving small goals every day, you feel accomplished and make steady progress on medium and long-term goals.

Tech companies call this a daily standup. Everyone shares what they did yesterday, what they're doing today, and any blockers. The name comes from a tradition of holding meetings while standing up to keep them short. Even though it's virtual, everyone still wants a quick meeting.

Your team may or may not need daily standups. Make a daily review a habit with your coffee.

Review Backwards & Forwards on a regular basis

While you're updating your to-do list daily, take time to review it.

Review your Done list. Remember things you're proud of and things that could have gone better. Your Done list can be long. Archive it so your main to-do list isn't overwhelming.

Future-gaze. What you considered important may no longer be. Reorder tasks. Backlog grooming is a workplace term.

Backwards-and-forwards reviews aren't required often. Every 3-6 months is fine. They help you see the forest as often as the trees.

Final Remarks

Keep your list simple. Done, Waiting, Top 3, Soon. These are the necessary sections. If you like, add more subsections; otherwise, keep it simple.

I recommend a morning review. By having clear goals and an action-oriented attitude, you'll be successful.