During the dot-com bust, I started my internet career. People used the internet intermittently to check email, plan travel, and do research. The average internet user spent 30 minutes online a day, compared to 7 today. To use the internet, you had to "log on" (most people still used dial-up), unlike today's always-on, high-speed mobile internet. In 2001, Amazon's market cap was $2.2B, 1/500th of what it is today. A study asked Americans if they'd adopt broadband, and most said no. They didn't see a need to speed up email, the most popular internet use. The National Academy of Sciences ranked the internet 13th among the 100 greatest inventions, below radio and phones. The internet was a cool invention, but it had limited uses and wasn't a good place to build a business. 

A small but growing movement of developers and founders believed the internet could be more than a read-only medium, allowing anyone to create and publish. This is web 2. The runner up name was read-write web. (These terms were used in prominent publications and conferences.) 

Web 2 concepts included letting users publish whatever they want ("user generated content" was a buzzword), social graphs, APIs and mashups (what we call composability today), and tagging over hierarchical navigation. Technical innovations occurred. A seemingly simple but important one was dynamically updating web pages without reloading. This is now how people expect web apps to work. Mobile devices that could access the web were niche (I was an avid Sidekick user). 

The contrast between what smart founders and engineers discussed over dinner and on weekends and what the mainstream tech world took seriously during the week was striking. Enterprise security appliances, essentially preloaded servers with security software, were a popular trend. Many of the same people would talk about "serious" products at work, then talk about consumer internet products and web 2. It was tech's biggest news. Web 2 products were seen as toys, not real businesses. They were hobbies, not work-related. 

There's a strong correlation between rich product design spaces and what smart people find interesting, which took me some time to learn and led to blog posts like "The next big thing will start out looking like a toy" Web 2's novel product design possibilities sparked dinner and weekend conversations. Imagine combining these features. What if you used this pattern elsewhere? What new product ideas are next? This excited people. "Serious stuff" like security appliances seemed more limited. 

The small and passionate web 2 community also stood out. I attended the first New York Tech meetup in 2004. Everyone fit in Meetup's small conference room. Late at night, people demoed their software and chatted. I have old friends. Sometimes I get asked how I first met old friends like Fred Wilson and Alexis Ohanian. These topics didn't interest many people, especially on the east coast. We were friends. Real community. Alex Rampell, who now works with me at a16z, is someone I met in 2003 when a friend said, "Hey, I met someone else interested in consumer internet." Rare. People were focused and enthusiastic. Revolution seemed imminent. We knew a secret nobody else did. 

My web 2 startup was called SiteAdvisor. When my co-founders and I started developing the idea in 2003, web security was out of control. Phishing and spyware were common on Internet Explorer PCs. SiteAdvisor was designed to warn users about security threats like phishing and spyware, and then, using web 2 concepts like user-generated reviews, add more subjective judgments (similar to what TrustPilot seems to do today). This staged approach was common at the time; I called it "Come for the tool, stay for the network." We built APIs, encouraged mashups, and did SEO marketing. 

Yahoo's 2005 acquisitions of Flickr and Delicious boosted web 2 in 2005. By today's standards, the amounts were small, around $30M each, but it was a signal. Web 2 was assumed to be a fun hobby, a way to build cool stuff, but not a business. Yahoo was a savvy company that said it would make web 2 a priority. 

As I recall, that's when web 2 started becoming mainstream tech. Early web 2 founders transitioned successfully. Other entrepreneurs built on the early enthusiasts' work. Competition shifted from ideation to execution. You had to decide if you wanted to be an idealistic indie bar band or a pragmatic stadium band. 

Web 2 was booming in 2007 Facebook passed 10M users, Twitter grew and got VC funding, and Google bought YouTube. The 2008 financial crisis tested entrepreneurs' resolve. Smart people predicted another great depression as tech funding dried up. 

Many people struggled during the recession. 2008-2011 was a golden age for startups. By 2009, talented founders were flooding Apple's iPhone app store. Mobile apps were booming. Uber, Venmo, Snap, and Instagram were all founded between 2009 and 2011. Social media (which had replaced web 2), cloud computing (which enabled apps to scale server side), and smartphones converged. Even if social, cloud, and mobile improve linearly, the combination could improve exponentially. 

This chart shows how I view product and financial cycles. Product and financial cycles evolve separately. The Nasdaq index is a proxy for the financial sentiment. Financial sentiment wildly fluctuates. 

Next row shows iconic startup or product years. Bottom-row product cycles dictate timing. Product cycles are more predictable than financial cycles because they follow internal logic. In the incubation phase, enthusiasts build products for other enthusiasts on nights and weekends. When the right mix of technology, talent, and community knowledge arrives, products go mainstream. (I show the biggest tech cycles in the chart, but smaller ones happen, like web 2 in the 2000s and fintech and SaaS in the 2010s.) 

Tech has changed since the 2000s. Few tech giants dominate the internet, exerting economic and cultural influence. In the 2000s, web 2 was ignored or dismissed as trivial. Entrenched interests respond aggressively to new movements that could threaten them. Creative patterns from the 2000s continue today, driven by enthusiasts who see possibilities where others don't. Know where to look. Crypto and web 3 are where I'd start. 

Today's negative financial sentiment reminds me of 2008. If we face a prolonged downturn, we can learn from 2008 by preserving capital and focusing on the long term. Keep an eye on the product cycle. Smart people are interested in things with product potential. This becomes true. Toys become necessities. Hobbies become mainstream. Optimists build the future, not cynics.

Full article is available here

Dharmesh Shah co-founded HubSpot. WordPlay reached $90,000 per month in revenue without utilizing any of his wealth.

His method:

Take Advantage Of An Established Trend

Remember Wordle? Dharmesh was instantly hooked. As was the tech world.

HubSpot's co-founder noted inefficiencies in a recent My First Million episode. He wanted to play daily. Dharmesh, a tinkerer and software engineer, decided to design a word game.

He's a billionaire. How could he?

1. Wordle had limitations in his opinion;

2. Dharmesh is fundamentally a developer. He desired to start something new and increase his programming knowledge;

3. This project may serve as an excellent illustration for his son, who had begun learning about software development.

Better It Up

Building a new Wordle wasn't successful.

WordPlay lets you play with friends and family. You could challenge them and compare the results. It is a built-in growth tool.

WordPlay features:

• the capacity to follow sophisticated statistics after creating an account;

• continuous feedback on your performance;

• Outstanding domain name (wordplay.com).

Project Development

WordPlay has 9.5 million visitors and 45 million games played since February.

HubSpot co-founder credits tremendous growth to flywheel marketing, pushing the game through his own following.

Choosing an exploding specialty and making sharing easy also helped.

Shah enabled Google Ads on the website to test earning potential. Monthly revenue was $90,000.

That's just Google Ads. If monetization was the goal, a specialized ad network like Ezoic could double or triple the amount.

Wordle was a great buy for The New York Times at $1 million.

From a simple landing where we tested our MVP to a platform that distributes 20,000 codes per month, we learned a lot.

Starting point

Kwotet was my first startup. Everyone might post book quotes online.

I wanted a change.

Kwotet lacked attention, thus I felt stuck. After experiencing the trials of starting Kwotet, I thought of developing a waitlist service, but I required a strong co-founder.

I knew Dries from school, but we weren't close. He was an entrepreneurial programmer who worked a lot outside school. I needed this.

We brainstormed throughout school hours. We developed features to put us first. We worked until 3 am to launch this product.

Putting in the hours is KEY when building a startup

The instant that we lost our spark

In Belgium, college seniors do their internship in their last semester.

As we both made the decision to pick a quite challenging company, little time was left for Lancero.

Eventually, we lost interest. We lost the spark…

The only logical choice was to find someone with the same spark we started with to acquire Lancero.

And we did @ MicroAcquire.

Sell before your product dies. Make sure to profit from all the gains.

What did we do following the sale?

Not far from selling Lancero I lost my dad. I was about to start a new company. It was focused on positivity. I got none left at the time.

We still didn’t let go of the dream of becoming full-time entrepreneurs. As Dries launched the amazing company Plunk, and I’m still in the discovering stages of my next journey!

Dream!

You’re an entrepreneur if:

• You're imaginative.

• You enjoy disassembling and reassembling things.

• You're adept at making new friends.

• YOU HAVE DREAMS.

You don’t need to believe me if I tell you “everything is possible”… I wouldn't believe it myself if anyone told me this 2 years ago.

Until I started doing, living my dreams.

The Traffic Light Approach to Reviewing Personal, Team and Project Development

What needs improvement? If you want to improve, you need to practice your sport, musical instrument, habit, or work project. You need to assess your progress.

Continuous improvement is the foundation of focused practice and a growth mentality. Not just individually. High-performing teams pursue improvement. Right? Why is it hard?

As a leadership coach, senior manager, and high-level athlete, I've found three key questions that may unlock high performance in individuals and teams.

Problems with Reviews

Reviewing and improving performance is crucial, however I hate seeing review sessions in my diary. I rarely respond to questionnaire pop-ups or emails. Why?

Time constrains. Requests to fill out questionnaires often state they will take 10–15 minutes, but I can think of a million other things to do with that time. Next, review overload. Businesses can easily request comments online. No matter what you buy, someone will ask for your opinion. This bombardment might make feedback seem bad, which is bad.

The problem is that we might feel that way about important things like personal growth and work performance. Managers and team leaders face a greater challenge.

When to Conduct a Review

We must be wise about reviewing things that matter to us. Timing and duration matter. Reviewing the experience as quickly as possible preserves information and sentiments. Time must be brief. The review's importance and size will determine its length. We might only take a few seconds to review our morning coffee, but we might require more time for that six-month work project.

These post-event reviews should be supplemented by periodic reflection. Journaling can help with daily reflections, but I also like to undertake personal reviews every six months on vacation or at a retreat.

As an employee or line manager, you don't want to wait a year for a performance assessment. Little and frequently is best, with a more formal and in-depth assessment (typically with a written report) in 6 and 12 months.

The Easiest Method to Conduct a Review Session

I follow Einstein's review process:

“Make things as simple as possible but no simpler.”

Thus, it should be brief but deliver the necessary feedback. Quality critique is hard to receive if the process is overly complicated or long.

I have led or participated in many review processes, from strategic overhauls of big organizations to personal goal coaching. Three key questions guide the process at either end:

• What ought to stop being done?

• What should we do going forward?

• What should we do first?

Following the Rule of 3, I compare it to traffic lights. Red, amber, and green lights:

• Red What ought should we stop?

• Amber What ought to we keep up?

• Green Where should we begin?

This approach is easy to understand and self-explanatory, however below are some examples under each area.

Red What ought should we stop?

As a team or individually, we must stop doing things to improve.

Sometimes they're bad. If we want to lose weight, we should avoid sweets. If a team culture is bad, we may need to stop unpleasant behavior like gossiping instead of having difficult conversations.

Not all things we should stop are wrong. Time matters. Since it is finite, we sometimes have to stop nice things to focus on the most important. Good to Great author Jim Collins famously said:

“Don’t let the good be the enemy of the great.”

Prioritizing requires this idea. Thus, decide what to stop to prioritize.

Amber What ought to we keep up?

Should we continue with the amber light? It helps us decide what to keep doing during review. Many items fall into this category, so focus on those that make the most progress.

Which activities have the most impact? Which behaviors create the best culture? Success-building habits?

Use these questions to find positive momentum. These are the fly-wheel motions, according to Jim Collins. The Compound Effect author Darren Hardy says:

“Consistency is the key to achieving and maintaining momentum.”

What can you do consistently to reach your goal?

Green Where should we begin?

Finally, green lights indicate new beginnings. Red/amber difficulties may be involved. Stopping a red issue may give you more time to do something helpful (in the amber).

This green space inspires creativity. Kolbs learning cycle requires active exploration to progress. Thus, it's crucial to think of new approaches, try them out, and fail if required.

This notion underpins lean start-build, up's measure, learn approach and agile's trying, testing, and reviewing. Try new things until you find what works. Thomas Edison, the lighting legend, exclaimed:

“There is a way to do it better — find it!”

Failure is acceptable, but if you want to fail forward, look back on what you've done.

John Maxwell concurred with Edison:

“Fail early, fail often, but always fail forward”

A good review procedure lets us accomplish that. To avoid failure, we must act, experiment, and reflect.

Use the traffic light system to prioritize queries. Ask:

• Red What needs to stop?

• Amber What should continue to occur?

• Green What might be initiated?

Take a moment to reflect on your day. Check your priorities with these three questions. Even if merely to confirm your direction, it's a terrific exercise!

Apple's latest revelation may shock iPod fans and former owners.

Apple discontinued the iPod touch on May 11, 2022. After 21 years, Apple killed the last surviving iPod, a device Steve Jobs believed would revolutionize the music industry.

Jobs was used to making bold predictions, but few expected Apple's digital music player to change the music industry. It did.

This chaos created new business opportunities. Spotify, YouTube, and Amazon are products of that chaotic era.

As the digital landscape changes, so do consumers, and the iPod has lost favor. I'm sure Apple realizes the importance of removing an icon. The iPod was Apple like the Mac and iPhone. I think it's bold to retire such a key Apple cornerstone. What would Jobs do?

iPod evolution across the ages

Here's an iPod family tree for all you enthusiasts.

iPod vintage (Oct 2001 to Sep 2014, 6 generations)

The original iPod had six significant upgrades since 2001. Apple announced an 80 GB ($249) and 160 GB ($349) iPod classic in 2007.

Apple updated the 80 GB model with a 120 GB device in September 2008. Apple upgraded the 120 GB model with a 160 GB variant a year later (2009). This was the last iteration, and Apple discontinued the classic in September 2014.

iPod nano (Jan 2004 to Sep 2005, 2 generations)

Apple debuted a smaller, brightly-colored iPod in 2004. The first model featured 4 GB, enough for 1,000 songs.

Apple produced a new 4 GB or 6 GB iPod mini in February 2005 and discontinued it in September when they released a better-looking iPod nano.

iTouch nano (Sep 2005 to July 2017, 7 generations)

I loved the iPod nano. It was tiny and elegant with enough tech to please most music aficionados, unless you carry around your complete music collection.

Apple owed much of the iPod nano's small form and success to solid-state flash memory. Flash memory doesn't need power because it has no moving parts. This makes the iPod nano more durable than the iPod classic and mini, which employ hard drives.

Apple manufactured seven generations of the iPod nano, improving its design, display screen, memory, battery, and software, but abandoned it in July 2017 due to dwindling demand.

Shuffle iPod (Jan 2005 to Jul 2017, 4 generations)

The iPod shuffle was entry-level. It was a simple, lightweight, tiny music player. The iPod shuffle was perfect for lengthy bike trips, runs, and hikes.

Apple sold 10 million iPod shuffles in the first year and kept making them for 12 years, through four significant modifications.

iOS device (Sep 2007 to May 2022, 7 generations)

The iPod touch's bigger touchscreen interface made it a curious addition to the iPod family. The iPod touch resembled an iPhone more than the other iPods, making them hard to tell apart.

Many were dissatisfied that Apple removed functionality from the iPod touch to avoid making it too similar to the iPhone. Seven design improvements over 15 years brought the iPod touch closer to the iPhone, but not completely.

The iPod touch uses the same iOS operating system as the iPhone, giving it access to many apps, including handheld games.

The iPod touch's long production run is due to the next generation of music-loving gamers.

What made the iPod cool

iPod revolutionized music listening. It was the first device to store and play MP3 music, allowing you to carry over 1,000 songs anywhere.

The iPod changed consumer electronics with its scroll wheel and touchscreen. Jobs valued form and function equally. He showed people that a product must look good to inspire an emotional response and ignite passion.

The elegant, tiny iPod was a tremendous sensation when it arrived for $399 in October 2001. Even at this price, it became a must-have for teens to CEOs.

It's hard to identify any technology that changed how music was downloaded and played like the iPod. Apple iPod and iTunes had 63% of the paid music download market in the fourth quarter of 2012.

The demise of the iPod was inevitable

Apple discontinuing the iPod touch after 21 years is sad. This ends a 00s music icon.

Jobs was a genius at anticipating market needs and opportunities, and Apple launched the iPod at the correct time.

Few consumer electronics items have had such a lasting impact on music lovers and the music industry as the iPod.

Smartphones and social media have contributed to the iPod's decline. Instead of moving to the music, the new generation of consumers is focused on social media. They're no longer passive content consumers; they're active content creators seeking likes and followers. Here, the smartphone has replaced the iPod.

It's hard not to feel a feeling of loss, another part of my adolescence now forgotten by the following generation.

So, if you’re lucky enough to have a working iPod, hang on to that relic and enjoy the music and the nostalgia.

Believe what you see, what people say

It’s sad that we never get trained to leave assumptions behind. - Sebastian Thrun

Many problems in software development are not because of code but because developers create the wrong software. This isn't rare because software is emergent and most individuals only realize what they want after it's built.

Inquisitive developers who pass the yellow cat test can improve the process.

Carpenters measure twice and cut the wood once. Developers are rarely so careful.

The Yellow Cat Test

Game of Thrones made dragons cool again, so I am reading The Game of Thrones book.

The yellow cat exam is from Syrio Forel, Arya Stark's fencing instructor.

Syrio tells Arya he'll strike left when fencing. He hits her after she dodges left. Arya says “you lied”. Syrio says his words lied, but his eyes and arm told the truth.

Arya learns how Syrio became Bravos' first sword.

“On the day I am speaking of, the first sword was newly dead, and the Sealord sent for me. Many bravos had come to him, and as many had been sent away, none could say why. When I came into his presence, he was seated, and in his lap was a fat yellow cat. He told me that one of his captains had brought the beast to him, from an island beyond the sunrise. ‘Have you ever seen her like?’ he asked of me.

“And to him I said, ‘Each night in the alleys of Braavos I see a thousand like him,’ and the Sealord laughed, and that day I was named the first sword.”

Arya screwed up her face. “I don’t understand.”

Syrio clicked his teeth together. “The cat was an ordinary cat, no more. The others expected a fabulous beast, so that is what they saw. How large it was, they said. It was no larger than any other cat, only fat from indolence, for the Sealord fed it from his own table. What curious small ears, they said. Its ears had been chewed away in kitten fights. And it was plainly a tomcat, yet the Sealord said ‘her,’ and that is what the others saw. Are you hearing?” Reddit discussion.

Development teams should not believe what they are told.

We created an appointment booking system. We thought it was an appointment-booking system. Later, we realized the software's purpose was to book the right people for appointments and discourage the unneeded ones.

The first 3 months of the project had half-correct requirements and software understanding.

Open your eyes

“Open your eyes is all that is needed. The heart lies and the head plays tricks with us, but the eyes see true. Look with your eyes, hear with your ears. Taste with your mouth. Smell with your nose. Feel with your skin. Then comes the thinking afterwards, and in that way, knowing the truth” Syrio Ferel

We must see what exists, not what individuals tell the development team or how developers think the software should work. Initial criteria cover 50/70% and change.

Developers build assumptions problems by assuming how software should work. Developers must quickly explain assumptions.

When a development team's assumptions are inaccurate, they must alter the code, DevOps, documentation, and tests.

It’s always faster and easier to fix requirements before code is written.

First-draft requirements can be based on old software. Development teams must grasp corporate goals and consider needs from many angles.

Testers help rethink requirements. They look at how software requirements shouldn't operate.

Technical features and benefits might misdirect software projects.

The initiatives that focused on technological possibilities developed hard-to-use software that needed extensive rewriting following user testing.

Software development

High-level criteria are different from detailed ones.

• The interpretation of words determines their meaning.

• Presentations are lofty, upbeat, and prejudiced.

• People's perceptions may be unclear, incorrect, or just based on one perspective (half the story)

• Developers can be misled by requirements, circumstances, people, plans, diagrams, designs, documentation, and many other things.

Developers receive misinformation, misunderstandings, and wrong assumptions. The development team must avoid building software with erroneous specifications.

Once code and software are written, the development team changes and fixes them.

Developers create software with incomplete information, they need to fill in the blanks to create the complete picture.

Conclusion

Yellow cats are often inaccurate when communicating requirements.

Before writing code, clarify requirements, assumptions, etc.

Everyone will pressure the development team to generate code rapidly, but this will slow down development.

Code changes are harder than requirements.