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

I've written a lot about Y Combinator's success, but as any startup founder or investor knows, many startups fail.

Rebel Fund invests in the top 5-10% of new Y Combinator startups each year, so we focus on identifying and supporting the most promising technology startups in our ecosystem. Given the power law dynamic and asymmetric risk/return profile of venture capital, we worry more about our successes than our failures. Since the latter still counts, this essay will focus on the proportion of YC startups that fail.

Since YC's launch in 2005, the figure below shows the percentage of active, inactive, and public/acquired YC startups by batch.

As more startups finish, the blue bars (active) decrease significantly. By 12 years, 88% of startups have closed or exited. Only 7% of startups reach resolution each year.

YC startups by status after 12 years:

Half the startups have failed, over one-third have exited, and the rest are still operating.

In venture investing, it's said that failed investments show up before successful ones. This is true for YC startups, but only in their early years.

Below, we only present resolved companies from the first chart. Some companies fail soon after establishment, but after a few years, the inactive vs. public/acquired ratio stabilizes around 55:45. After a few years, a YC firm is roughly as likely to quit as fail, which is better than I imagined.

I prepared this post because Rebel investors regularly question me about YC startup failure rates and how long it takes for them to exit or shut down.

Early-stage venture investors can overlook it because 100x investments matter more than 0x investments.

YC founders can ignore it because it shouldn't matter if many of their peers succeed or fail ;)

Learn these subtle cues to gain influence.

Hate being ignored?

As a 24-year-old, I struggled at work. Attention-getting tips How to avoid being judged by my size, gender, and lack of wrinkles or gray hair?

I've learned seniority hacks. Influence. Within two years as a product manager, I led a team. I'm a Stanford MBA student.

These communication hacks can make you look senior and influential.

1. Slowly speak

We speak quickly because we're afraid of being interrupted.

When I doubt my ideas, I speak quickly. How can we slow down? Jamie Chapman says speaking slowly saps our energy.

Chapman suggests emphasizing certain words and pausing.

2. Interrupted? Stop the stopper

Someone interrupt your speech?

Don't wait. "May I finish?" No pause needed. Stop interrupting. I first tried this in Leadership Laboratory at Stanford. How quickly I gained influence amazed me.

Next time, try “May I finish?” If that’s not enough, try these other tips from Wendy R.S. O’Connor.

3. Context

Others don't always see what's obvious to you.

Through explanation, you help others see the big picture. If a senior knows it, you help them see where your work fits.

4. Don't ask questions in statements

“Your statement lost its effect when you ended it on a high pitch,” a group member told me. Upspeak, it’s called. I do it when I feel uncertain.

Upspeak loses influence and credibility. Unneeded. When unsure, we can say "I think." We can even ask a proper question.

Someone else's boasting is no reason to be dismissive. As leaders and colleagues, we should listen to our colleagues even if they use this speech pattern.

Give your words impact.

5. Signpost structure

Signposts improve clarity by providing structure and transitions.

Communication coach Alexander Lyon explains how to use "first," "second," and "third" He explains classic and summary transitions to help the listener switch topics.

Signs clarify. Clarity matters.

6. Eliminate email fluff

“Fine. When will the report be ready? — Jeff.”

Notice how senior leaders write short, direct emails? I often use formalities like "dear," "hope you're well," and "kind regards"

Formality is (usually) unnecessary.

7. Replace exclamation marks with periods

See how junior an exclamation-filled email looks:

Hi, all!
Hope you’re as excited as I am for tomorrow! We’re celebrating our accomplishments with cake! Join us tomorrow at 2 pm!
See you soon!

Why the exclamation points? Why not just one?

Hi, all.
Hope you’re as excited as I am for tomorrow. We’re celebrating our accomplishments with cake. Join us tomorrow at 2 pm!
See you soon.

8. Take space

"Playing high" means having an open, relaxed body, says Stanford professor and author Deborah Gruenfield.

Crossed legs or looking small? Relax. Get bigger.

Crypto and blockchain have rebranded as web3. They probably thought it sounded better and didn't want the baggage of scam ICOs, STOs, and skirted securities laws.

It was like Facebook becoming Meta. Crypto's biggest players wanted to change public (and regulator) perception away from pump-and-dump schemes.

After the 2018 ICO gold rush, it's understandable. Every project that raised millions (or billions) never shipped a meaningful product.

Like many crazes, charlatans took the money and ran.

Despite its grifter past, web3 is THE hot topic today as more founders, venture firms, and larger institutions look to build the future decentralized internet.

Supposedly.

How often have you heard: This will change the world, fix the internet, and give people power?

Why are most of web3's biggest proponents (and beneficiaries) the same rich, powerful players who built and invested in the modern internet? It's like they want to remake and own the internet.

Something seems off about that.

Why are insiders getting preferential presale terms before the public, allowing early investors and proponents to flip dirt cheap tokens and advisors shares almost immediately after the public sale?

It's a good gig with guaranteed markups, no risk or progress.

If it sounds like insider trading, it is, at least practically. This is clear when people talk about blockchain/web3 launches and tokens.

Fast money, quick flips, and guaranteed markups/returns are common.

Incentives-wise, it's hard to blame them. Who can blame someone for following the rules to win? Is it their fault or regulators' for not leveling the playing field?

It's similar to oil companies polluting for profit, Instagram depressing you into buying a new dress, or pharma pushing an unnecessary pill.

All of that is fair game, at least until we change the playbook, because people (and corporations) change for pain or love. Who doesn't love money?

belief based on money gain

Sinclair:

“It is difficult to get a man to understand something when his salary depends upon his not understanding it.”

Bitcoin, blockchain, and web3 analogies?

Most blockchain and web3 proponents are true believers, not cynical capitalists. They believe blockchain's inherent transparency and permissionless trust allow humanity to evolve beyond our reptilian ways and build a better decentralized and democratic world.

They highlight issues with the modern internet and monopoly players like Google, Facebook, and Apple. Decentralization fixes everything

If we could give power back to the people and get governments/corporations/individuals out of the way, we'd fix everything.

Blockchain solves supply chain and child labor issues in China.

To meet Paris climate goals, reduce emissions. Create a carbon token.

Fixing online hatred and polarization Web3 Twitter and Facebook replacement.

Web3 must just be the answer for everything… your “perfect” silver bullet.

Nothing fits everyone. Blockchain has pros and cons like everything else.

Blockchain's viral, ponzi-like nature has an MLM (mid level marketing) feel. If you bought Taylor Swift's NFT, your investment is tied to her popularity.

Probably makes you promote Swift more. Play music loudly.

Here's another example:

Imagine if Jehovah’s Witnesses (or evangelical preachers…) got paid for every single person they converted to their cause.

It becomes a self-fulfilling prophecy as their faith and wealth grow.

Which breeds extremism? Ultra-Orthodox Jews are an example. maximalists

Bitcoin and blockchain are causes, religions. It's a money-making movement and ideal.

We're good at convincing ourselves of things we want to believe, hence filter bubbles.

I ignore anything that doesn't fit my worldview and seek out like-minded people, which algorithms amplify.

Then what?

Is web3 merely a new scam?

No, never!

Blockchain has many crucial uses.

Sending money home/abroad without bank fees;

Like fleeing a war-torn country and converting savings to Bitcoin;

Like preventing Twitter from silencing dissidents.

Permissionless, trustless databases could benefit society and humanity. There are, however, many limitations.

Lost password?

What if you're cheated?

What if Trump/Putin/your favorite dictator incites a coup d'état?

What-ifs abound. Decentralization's openness brings good and bad.

No gatekeepers or firefighters to rescue you.

ISIS's fundraising is also frictionless.

Community-owned apps with bad interfaces and service.

Trade-offs rule.

So what compromises does web3 make?

What are your trade-offs? Decentralization has many strengths and flaws. Like Bitcoin's wasteful proof-of-work or Ethereum's political/wealth-based proof-of-stake.

To ensure the survival and veracity of the network/blockchain and to safeguard its nodes, extreme measures have been designed/put in place to prevent hostile takeovers aimed at altering the blockchain, i.e., adding money to your own wallet (account), etc.

These protective measures require significant resources and pose challenges. Reduced speed and throughput, high gas fees (cost to submit/write a transaction to the blockchain), and delayed development times, not to mention forked blockchain chains oops, web3 projects.

Protecting dissidents or rogue regimes makes sense. You need safety, privacy, and calm.

First-world life?

What if you assumed EVERYONE you saw was out to rob/attack you? You'd never travel, trust anyone, accomplish much, or live fully. The economy would collapse.

It's like an ant colony where half the ants do nothing but wait to be attacked.

Waste of time and money.

11% of the US budget goes to the military. Imagine what we could do with the $766B+ we spend on what-ifs annually.

Is so much hypothetical security needed?

Blockchain and web3 are similar.

Does your app need permissionless decentralization? Does your scooter-sharing company really need a proof-of-stake system and 1000s of nodes to avoid Russian hackers? Why?

Worst-case scenario? It's not life or death, unless you overstate the what-ifs. Web3 proponents find improbable scenarios to justify decentralization and tokenization.

Do I need a token to prove ownership of my painting? Unless I'm a master thief, I probably bought it.

despite losing the receipt.

I do, however, love Web 3.

Enough Web3 bashing for now. Understand? Decentralization isn't perfect, but it has huge potential when applied to the right problems.

I see many of the right problems as disrupting big tech's ruthless monopolies. I wrote several years ago about how tokenized blockchains could be used to break big tech's stranglehold on platforms, marketplaces, and social media.

Tokenomics schemes can be used for good and are powerful. Here’s how.

Before the ICO boom, I made a series of predictions about blockchain/crypto's future. It's still true.

Here's where I was then and where I see web3 going:

My 11 Big & Bold Predictions for Blockchain

In the near future, people may wear crypto cash rings or bracelets.

1. While some governments repress cryptocurrency, others will start to embrace it.

2. Blockchain will fundamentally alter voting and governance, resulting in a more open election process.

3. Money freedom will lead to a more geographically open world where people will be more able to leave when there is unrest.

4. Blockchain will make record keeping significantly easier, eliminating the need for a significant portion of government workers whose sole responsibility is paperwork.

5. Overrated are smart contracts.

6. Tokens will replace company stocks.

7. Blockchain increases real estate's liquidity, value, and volatility.

8. Healthcare may be most affected.

9. Crypto could end privacy and lead to Minority Report.

10. New companies with network effects will displace incumbents.

11. Soon, people will wear rings or bracelets with crypto cash.

Some have already happened, while others are still possible.

Time will tell if they happen.

And finally:

What will web3 be?

Who will be in charge?

Closing remarks

Hope you enjoyed this web3 dive. There's much more to say, but that's for another day.

We're writing history as we go.

Tech regulation, mergers, Bitcoin surge How will history remember us?

What about web3 and blockchain?

Is this a revolution or a tulip craze?

Remember, actions speak louder than words (share them in the comments).

Your turn.