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

Reflections on the closed company Hola! Dating app

I'll discuss my fuckups as an entrepreneur and CEO. All of them refer to the dating app Hola!, which I co-founded and starred in.

Spring 2021 was when we started. Two techies and two non-techies created a dating app. Pokemon Go and Tinder were combined.

Online dating is a business, and it takes two weeks from a like to a date. We questioned online dating app users if they met anyone offline last year.

75% replied yes, 50% sometimes, 25% usually.

Offline dating is popular, yet people have concerns.

• Men are reluctant to make mistakes in front of others.

• Women are curious about the background of everyone who approaches them.

We designed unique mechanics that let people date after a match. No endless chitchat. Women would be safe while men felt like cowboys.

I wish to emphasize three faults that lead to founders' estrangement.

This detachment ultimately led to us shutting down the company.

The wrong technology stack

Situation

Instead of generating a faster MVP and designing an app in a universal stack for iOS and Android, I argued we should pilot the app separately for iOS and Android. Technical founders' expertise made this possible.

Self-reflection

Mistaken strategy. We lost time and resources developing two apps at once. We chose iOS since it's more profitable. Apple took us out after the release, citing Guideline 4.3 Spam. After 4 months, we had nothing. We had a long way to go to get the app on Android and the Store.

I suggested creating a uniform platform for the company's growth. This makes parallel product development easier. The strategist's lack of experience and knowledge made it a piece of crap.

What would I have changed if I could?

We should have designed an Android universal stack. I expected Apple to have issues with a dating app.

Our approach should have been to launch something and subsequently improve it, but prejudice won.

The lesson

Discuss the IT stack with your CTO. It saves time and money. Choose the easiest MVP method.

2. A tardy search for investments

Situation

Though the universe and other founders encouraged me to locate investors first, I started pitching when we almost had an app.

When angels arrived, it was time to close. The app was banned, war broke out, I left the country, and the other co-founders stayed. We had no savings.

Self-reflection

I loved interviewing users. I'm proud of having done 1,000 interviews. I wanted to understand people's pain points and improve the product.

Interview results no longer affected the product. I was terrified to start pitching. I filled out accelerator applications and redid my presentation. You must go through that so you won't be terrified later.

What would I have changed if I could?

Get an external or internal mentor to help me with my first pitch as soon as possible. I'd be supported if criticized. He'd cheer with me if there was enthusiasm.

In 99% of cases, I'm comfortable jumping into the unknown, but there are exceptions. The mentor's encouragement would have prompted me to act sooner.

The lesson

Begin fundraising immediately. Months may pass. Show investors your pre-MVP project. Draw inferences from feedback.

3. Role ambiguity

Situation

My technical co-founders were also part-time lead developers, which produced communication issues. As co-founders, we communicated well and recognized the problems. Stakes, vesting, target markets, and approach were agreed upon.

We were behind schedule. Technical debt and strategic gap grew.

Bi-daily and weekly reviews didn't help. Each time, there were explanations. Inside, I was freaking out.

Self-reflection

I am a fairly easy person to talk to. I always try to stick to agreements; otherwise, my head gets stuffed with unnecessary information, interpretations, and emotions.

Sit down -> talk -> decide -> do -> evaluate the results. Repeat it.

If I don't get detailed comments, I start ruining everyone's mood. If there's a systematic violation of agreements without a good justification, I won't join the project or I'll end the collaboration.

What would I have done otherwise?

This is where it’s scariest to draw conclusions. Probably the most logical thing would have been not to start the project as we started it. But that was already a completely different project. So I would not have done anything differently and would have failed again.

But I drew conclusions for the future.

The lesson

First-time founders should find an adviser or team coach for a strategic session. It helps split the roles and responsibilities.

How did his money blind me?

Like most fledgling entrepreneurs, I wanted a mentor. I met as many nearby folks with "entrepreneur" in their LinkedIn biographies for coffee.

These meetings taught me a lot, and I'd suggest them to any new creator. Attention! Meeting with many experienced entrepreneurs means getting contradictory advice. One entrepreneur will tell you to do X, then the next one you talk to may tell you to do Y, which are sometimes opposites. You'll have to chose which suggestion to take after the chats.

I experienced this. Same afternoon, I had two coffee meetings with experienced entrepreneurs. The first meeting was with a billionaire entrepreneur who took his company public.

I met him in a swanky hotel lobby and ordered a drink I didn't pay for. As a fledgling entrepreneur, money was scarce.

During the meeting, I demoed the software I'd built, he liked it, and we spent the hour discussing what features would make it a success. By the end of the meeting, he requested I include a killer feature we both agreed would attract buyers. The feature was complex and would require some time. The billionaire I was sipping coffee with in a beautiful hotel lobby insisted people would love it, and that got me enthusiastic.

The second meeting was with a young entrepreneur who had recently raised a small amount of investment and looked as eager to pitch me as I was to pitch him. I forgot his name. I mostly recall meeting him in a filthy coffee shop in a bad section of town and buying his pricey cappuccino. Water for me.

After his pitch, I demoed my app. When I was done, he barely noticed. He questioned my customer acquisition plan. Who was my client? What did they offer? What was my plan? Etc. No decent answers.

After our meeting, he insisted I spend more time learning my market and selling. He ignored my questions about features. Don't worry about features, he said. Customers will request features. First, find them.

Putting your faith in results over relevance

Problems plagued my afternoon. I met with two entrepreneurs who gave me differing advice about how to proceed, and I had to decide which to pursue. I couldn't decide.

Ultimately, I followed the advice of the billionaire.

Obviously.

Who wouldn’t? That was the guy who clearly knew more.

A few months later, I constructed the feature the billionaire said people would line up for.

The new feature was unpopular. I couldn't even get the billionaire to answer an email showing him what I'd done. He disappeared.

Within a few months, I shut down the company, wasting all the time and effort I'd invested into constructing the killer feature the billionaire said I required.

Would follow the struggling entrepreneur's advice have saved my company? It would have saved me time in retrospect. Potential consumers would have told me they didn't want what I was producing, and I could have shut down the company sooner or built something they did want. Both outcomes would have been better.

Now I know, but not then. I favored achievement above relevance.

Success vs. relevance

The millionaire gave me advice on building a large, successful public firm. A successful public firm is different from a startup. Priorities change in the last phase of business building, which few entrepreneurs reach. He gave wonderful advice to founders trying to double their stock values in two years, but it wasn't beneficial for me.

The other failing entrepreneur had relevant, recent experience. He'd recently been in my shoes. We still had lots of problems. He may not have achieved huge success, but he had valuable advice on how to pass the closest hurdle.

The money blinded me at the moment. Not alone So much of company success is defined by money valuations, fundraising, exits, etc., so entrepreneurs easily fall into this trap. Money chatter obscures the value of knowledge.

Don't base startup advice on a person's income. Focus on what and when the person has learned. Relevance to you and your goals is more important than a person's accomplishments when considering advice.

Is iPhone's Dynamic Island invention or a marketing ploy?

First of all, why the notch?

When Apple debuted the iPhone X with the notch, some were surprised, confused, and amused by the goof. Let the Brits keep the new meaning of top-notch.

Apple removed the bottom home button to enhance screen space. The tides couldn't overtake part of the top. This section contained sensors, a speaker, a microphone, and cameras for facial recognition. A town resisted Apple's new iPhone design.

From iPhone X to 13, the notch has gotten smaller. We expected this as technology and engineering progressed, but we hated the notch. Apple approved. They attached it to their other gadgets.

Apple accepted, owned, and ran with the iPhone notch, it has become iconic (or infamous); and that’s intentional.

The Island Where Apple Is

Apple needs to separate itself, but they know how to do it well. The iPhone 14 Pro finally has us oohing and aahing. Life-changing, not just higher pixel density or longer battery.

Dynamic Island turned a visual differentiation into great usefulness, which may not be life-changing. Apple always welcomes the controversy, whether it's $700 for iMac wheels, no charging block with a new phone, or removing the headphone jack.

Apple knows its customers will be loyal, even if they're irritated. Their odd design choices often cause controversy. It's calculated that people blog, review, and criticize Apple's products. We accept what works for them.

While the competition zigs, Apple zags. Sometimes they zag too hard and smash into a wall, but we talk about it anyways, and that’s great publicity for them.

Getting Dependent on the drug

The notch became a crop. Dynamic Island's design is helpful, intuitive, elegant, and useful. It increases iPhone usability, productivity (slightly), and joy. No longer unsightly.

The medication helps with multitasking. It's a compact version of the iPhone's Live Activities lock screen function. Dynamic Island enhances apps and activities with visual effects and animations whether you engage with it or not. As you use the pill, its usefulness lessens. It lowers user notifications and consolidates them with live and permanent feeds, delivering quick app statuses. It uses the black pixels on the iPhone 14's display, which looked like a poor haircut.

The pill may be a gimmick to entice customers to use more Apple products and services. Apps may promote to their users like a live billboard.

Be prepared to get a huge dose of Dynamic Island’s “pill” like you never had before with the notch. It might become so satisfying and addicting to use, that every interaction with it will become habit-forming, and you’re going to forget that it ever existed.

WARNING: A Few Potential Side Effects

Vision blurred Dynamic Island's proximity to the front-facing camera may leave behind grease that blurs photos. Before taking a selfie, wipe the camera clean.

Strained thumb To fully use Dynamic Island, extend your thumb's reach 6.7 inches beyond your typical, comfortable range.

Happiness, contentment The Dynamic Island may enhance Endorphins and Dopamine. Multitasking, interactions, animations, and haptic feedback make you want to use this function again and again.

Motion-sickness Dynamic Island's motions and effects may make some people dizzy. If you can disable animations, you can avoid motion sickness.

I'm not a doctor, therefore they aren't established adverse effects.

Does Dynamic Island Include Multiple Tasks?

Dynamic Islands is a placebo for multitasking. Apple might have compromised on iPhone multitasking. It won't make you super productive, but it's a step up.

iPhone is primarily for personal use, like watching videos, messaging friends, sending money to friends, calling friends about the money you were supposed to send them, taking 50 photos of the same leaf, investing in crypto, driving for Uber because you lost all your money investing in crypto, listening to music and hailing an Uber from a deserted crop field because while you were driving for Uber your passenger stole your car and left you stranded, so you used Apple’s new SOS satellite feature to message your friend, who still didn’t receive their money, to hail you an Uber; now you owe them more money… karma?

We won't be watching videos on iPhones while perusing 10,000-row spreadsheets anytime soon. True multitasking and productivity aren't priorities for Apple's iPhone. Apple doesn't to preserve the iPhone's experience. Like why there's no iPad calculator. Apple doesn't want iPad users to do math, but isn't essential for productivity?

Digressing.

Apple will block certain functions so you must buy and use their gadgets and services, immersing yourself in their ecosystem and dictating how to use their goods.

Dynamic Island is a poor man’s multi-task for iPhone, and that’s fine it works for most iPhone users. For substantial productivity Apple prefers you to get an iPad or a MacBook. That’s part of the reason for restrictive features on certain Apple devices, but sometimes it’s based on principles to preserve the integrity of the product, according to Apple’s definition.

Is Apple using deception?

Dynamic Island may be distracting you from a design decision. The answer is kind of. Elegant distraction

When you pull down a smartphone webpage to refresh it or minimize an app, you get seamless animations. It's not simply because it appears better; it's due to iPhone and smartphone processing speeds. Such limits reduce the system's response to your activity, slowing the experience. Designers and developers use animations and effects to distract us from the time lag (most of the time) and sometimes because it looks cooler and smoother.

Dynamic Island makes apps more useable and interactive. It shows system states visually. Turn signal audio and visual cues, voice assistance, physical and digital haptic feedbacks, heads-up displays, fuel and battery level gauges, and gear shift indicators helped us overcome vehicle design problems.

Dynamic Island is a wonderfully delightful (and temporary) solution to a design “problem” until Apple or other companies can figure out a way to sink the cameras under the smartphone screen.

Apple Has Returned to Being an Innovative & Exciting Company

Now Apple's products are exciting. Next, bring back real Apple events, not pre-recorded demos.

Dynamic Island integrates hardware and software. What will this new tech do? How would this affect device use? Or is it just hype?

Dynamic Island may be an insignificant improvement to the iPhone, but it sure is promising for the future of bridging the human and computer interaction gap.

This is arguably the best three-minute demonstration I've ever seen of anything. Derek Sivers turns a shaky video of a lone dancing guy at a music festival into a leadership lesson.

A leader must have the courage to stand alone and appear silly. But what he's doing is so straightforward that it's almost instructive. This is critical. You must be simple to follow!

Now comes the first follower, who plays an important role: he publicly demonstrates how to follow. The leader embraces him as an equal, so it's no longer about the leader — it's about them, plural. He's inviting his friends to join him. It takes courage to be the first follower! You stand out and dare to be mocked. Being a first follower is a style of leadership that is underappreciated. The first follower elevates a lone nut to the position of leader. If the first follower is the spark that starts the fire, the leader is the flint.

This link was sent to me by @ottmark, who noted its resemblance to Kurt Vonnegut's three categories of specialists required for revolution.

The rarest of these specialists, he claims, is an actual genius – a person capable generating seemingly wonderful ideas that are not widely known. "A genius working alone is generally dismissed as a crazy," he claims.

The second type of specialist is much easier to find: a highly intellectual person in good standing in his or her community who understands and admires the genius's new ideas and can attest that the genius is not insane. "A person like him working alone can only crave loudly for changes, but fail to say what their shapes should be," Slazinger argues.

Jeff Veen reduced the three personalities to "the inventor, the investor, and the evangelist" on Twitter.

As technology develops, you should stay up to date

You don't want to fall behind, do you? This post covers 7 tech-related things you should know.

You'll learn how to operate your computer (and other electronic devices) like an expert and how to leverage the Internet and social media to create your brand and business. Read on to stay relevant in today's tech-driven environment.

You must learn how to code.

Future-language is coding. It's how we and computers talk. Learn coding to keep ahead.

Try Codecademy or Code School. There are also numerous free courses like Coursera or Udacity, but they take a long time and aren't necessarily self-paced, so it can be challenging to find the time.

Artificial intelligence (AI) will transform all jobs.

Our skillsets must adapt with technology. AI is a must-know topic. AI will revolutionize every employment due to advances in machine learning.

Here are seven AI subjects you must know.

What is artificial intelligence?

How does artificial intelligence work?

What are some examples of AI applications?

How can I use artificial intelligence in my day-to-day life?

What jobs have a high chance of being replaced by artificial intelligence and how can I prepare for this?

Can machines replace humans? What would happen if they did?

How can we manage the social impact of artificial intelligence and automation on human society and individual people?

Blockchain Is Changing the Future

Few of us know how Bitcoin and blockchain technology function or what impact they will have on our lives. Blockchain offers safe, transparent, tamper-proof transactions.

It may alter everything from business to voting. Seven must-know blockchain topics:

1. Describe blockchain.

2. How does the blockchain function?

3. What advantages does blockchain offer?

4. What possible uses for blockchain are there?

5. What are the dangers of blockchain technology?

6. What are my options for using blockchain technology?

7. What does blockchain technology's future hold?

Cryptocurrencies are here to stay

Cryptocurrencies employ cryptography to safeguard transactions and manage unit creation. Decentralized cryptocurrencies aren't controlled by governments or financial institutions.

Bitcoin, the first cryptocurrency, was launched in 2009. Cryptocurrencies can be bought and sold on decentralized exchanges.

Bitcoin is here to stay.

Bitcoin isn't a fad, despite what some say. Since 2009, Bitcoin's popularity has grown. Bitcoin is worth learning about now. Since 2009, Bitcoin has developed steadily.

With other cryptocurrencies emerging, many people are wondering if Bitcoin still has a bright future. Curiosity is natural. Millions of individuals hope their Bitcoin investments will pay off since they're popular now.

Thankfully, they will. Bitcoin is still running strong a decade after its birth. Here's why.

The Internet of Things (IoT) is no longer just a trendy term.

IoT consists of internet-connected physical items. These items can share data. IoT is young but developing fast.

20 billion IoT-connected devices are expected by 2023. So much data! All IT teams must keep up with quickly expanding technologies. Four must-know IoT topics:

1. Recognize the fundamentals: Priorities first! Before diving into more technical lingo, you should have a fundamental understanding of what an IoT system is. Before exploring how something works, it's crucial to understand what you're working with.

2. Recognize Security: Security does not stand still, even as technology advances at a dizzying pace. As IT professionals, it is our duty to be aware of the ways in which our systems are susceptible to intrusion and to ensure that the necessary precautions are taken to protect them.

3. Be able to discuss cloud computing: The cloud has seen various modifications over the past several years once again. The use of cloud computing is also continually changing. Knowing what kind of cloud computing your firm or clients utilize will enable you to make the appropriate recommendations.

4. Bring Your Own Device (BYOD)/Mobile Device Management (MDM) is a topic worth discussing (MDM). The ability of BYOD and MDM rules to lower expenses while boosting productivity among employees who use these services responsibly is a major factor in their continued growth in popularity.

IoT Security is key

As more gadgets connect, they must be secure. IoT security includes securing devices and encrypting data. Seven IoT security must-knows:

1. fundamental security ideas

2. Authorization and identification

3. Cryptography

4. electronic certificates

5. electronic signatures

6. Private key encryption

7. Public key encryption

Final Thoughts

With so much going on in the globe, it can be hard to stay up with technology. We've produced a list of seven tech must-knows.