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

What they'll do is scarier.

My acquaintance recently joined a VC-funded startup. Money, equity, and upside possibilities were nice, but he had a nagging dread.

They just secured a $40M round and are hiring like crazy to prepare for their IPO in two years. All signals pointed to this startup's (a B2B IT business in a stable industry) success, and its equity-holding workers wouldn't pass that up.

Five months after starting the work, my friend struggled with leaving. We might overlook the awful culture and long hours at the proper price. This price plus the company's fate and survival abilities sent my friend departing in an unpleasant unplanned resignation before jumping on yet another sinking ship.

This affects founders. This affects VC-backed companies (and all businesses). This affects anyone starting, buying, or running a business.

Here's the under-the-table approach that's draining VC capital, leaving staff terrified (or jobless), founders rattled, and investors upset. How to recognize, solve, and avoid it

The unsettling reality behind door #1

You can't raise money off just your looks, right? If "looks" means your founding team's expertise, then maybe. In my friend's case, the founding team's strong qualifications and track records won over investors before talking figures.

They're hardly the only startup to raise money without a profitable customer acquisition strategy. Another firm raised money for an expensive sleep product because it's eco-friendly. They were off to the races with a few keywords and key players.

Both companies, along with numerous others, elected to invest on product development first. Company A employed all the tech, then courted half their market (they’re a tech marketplace that connects two parties). Company B spent millions on R&D to create a palatable product, then flooded the world with marketing.

My friend is on Company B's financial team, and he's seen where they've gone wrong. It's terrible.

Company A (tech market): Growing? Not quite. To achieve the ambitious expansion they (and their investors) demand, they've poured much of their little capital into salespeople: Cold-calling commission and salary salesmen. Is it working? Considering attrition and companies' dwindling capital, I don't think so.

Company B (green sleep) has been hiring, digital marketing, and opening new stores like crazy. Growing expenses should result in growing revenues and a favorable return on investment; if you grow too rapidly, you may neglect to check that ROI.

Once Company A cut headcount and Company B declared “going concerned”, my friend realized both startups had the same ailment and didn't recognize it.

I shouldn't have to ask a friend to verify a company's cash reserves and profitability to spot a financial problem. It happened anyhow.

The frightening part isn't that investors were willing to invest millions without product-market fit, CAC, or LTV estimates. That's alarming, but not as scary as the fact that startups aren't understanding the problem until VC rounds have dried up.

When they question consultants if their company will be around in 6 months. It’s a red flag. How will they stretch $20M through a 2-year recession with a $3M/month burn rate and no profitability? Alarms go off.

Who's in danger?

In a word, everyone who raised money without a profitable client acquisition strategy or enough resources to ride out dry spells.

Money mismanagement and poor priorities affect every industry (like sinking all your capital into your product, team, or tech, at the expense of probing what customer acquisition really takes and looks like).

This isn't about tech, real estate, or recession-proof luxury products. Fast, cheap, easy money flows into flashy-looking teams with buzzwords, trending industries, and attractive credentials.

If these companies can't show progress or get a profitable CAC, they can't raise more money. They die if they can't raise more money (or slash headcount and find shoestring budget solutions until they solve the real problem).

The kiss of death (and how to avoid it)

If you're running a startup and think raising VC is the answer, pause and evaluate. Do you need the money now?

I'm not saying VC is terrible or has no role. Founders have used it as a Band-Aid for larger, pervasive problems. Venture cash isn't a crutch for recruiting consumers profitably; it's rocket fuel to get you what and who you need.

Pay-to-play isn't a way to throw money at the wall and hope for a return. Pay-to-play works until you run out of money, and if you haven't mastered client acquisition, your cash will diminish quickly.

How can you avoid this bottomless pit? Tips:

• Understand your burn rate

• Keep an eye on your growth or profitability.

• Analyze each and every marketing channel and initiative.

• Make lucrative customer acquisition strategies and satisfied customers your top two priorities. not brand-new products. not stellar hires. avoid the fundraising rollercoaster to save time. If you succeed in these two tasks, investors will approach you with their thirsty offers rather than the other way around, and your cash reserves won't diminish as a result.

Not as much as your grandfather

My family friend always justified expensive, impractical expenditures by saying it was only monopoly money. In business, startups, and especially with money from investors expecting a return, that's not true.

More founders could understand that there isn't always another round if they viewed VC money as their own limited pool. When the well runs dry, you must refill it or save the day.

Venture financing isn't your grandpa's money. A discerning investor has entrusted you with dry powder in the hope that you'll use it wisely, strategically, and thoughtfully. Use it well.

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!

After viewing its insanity, I had to leave this platform.

I joined LinkedIn recently. That's how I aim to increase my readership and gain recognition. LinkedIn's premise appealed to me: a Facebook-like platform for professional networking.

I don't use Facebook since it's full of propaganda. It seems like a professional, apolitical space, right?

I expected people to:

• be more formal and respectful than on Facebook.

• Talk about the inclusiveness of the workplace. Studies consistently demonstrate that inclusive, progressive workplaces outperform those that adhere to established practices.

• Talk about business in their industry. Yep. I wanted to read articles with advice on how to write better and reach a wider audience.

Oh, sh*t. I hadn't anticipated that.

After posting and reading about inclusivity and pro-choice, I was startled by how many professionals acted unprofessionally. I've seen:

• Men have approached me in the DMs in a really aggressive manner. Yikes. huge yikes Not at all professional.

• I've heard pro-choice women referred to as infant killers by many people. If I were the CEO of a company and I witnessed one of my employees acting that poorly, I would immediately fire them.

• Many posts are anti-LGBTQIA+, as I've noticed. a lot, like, a lot. Some are subtly stating that the world doesn't need to know, while others are openly making fun of transgender persons like myself.

• Several medical professionals were posting explicitly racist comments. Even if you are as white as a sheet like me, you should be alarmed by this. Who's to guarantee a patient who is black won't unintentionally die?

• I won't even get into how many men in STEM I observed pushing for the exclusion of women from their fields. I shouldn't be surprised considering the majority of those men I've encountered have a passionate dislike for women, but goddamn, dude.

Many people appear entirely too at ease displaying their bigotry on their professional profiles.

As a white female, I'm always shocked by people's open hostility. Professional environments are very important.

I don't know if this is still true (people seem too politicized to care), but if I heard many of these statements in person, I'd suppose they feel ashamed. Really.

Are you not ashamed of being so mean? Are you so weak that competing with others terrifies you? Isn't this embarrassing?

LinkedIn isn't great at censoring offensive comments. These people aren't getting warnings. So they were safe while others were unsafe.

The CEO in me would want to know if I had placed a bigot on my staff.

I always wondered if people's employers knew about their online behavior. If they know how horrible they appear, they don't care.

As a manager, I was picky about hiring. Obviously. In most industries, it costs $1,000 or more to hire a full-time employee, so be sure it pays off.

Companies that embrace diversity and tolerance (and are intolerant of intolerance) are more profitable, likely to recruit top personnel, and successful.

People avoid businesses that alienate them. That's why I don't eat at Chic-Fil-A and why folks avoid MyPillow. Being inclusive is good business.

CEOs are harmed by online bigots. Image is an issue. If you're a business owner, you can fire staff who don't help you.

On the one hand, I'm delighted it makes it simpler to identify those with whom not to do business.

Don’t get me wrong. I'm glad I know who to avoid when hiring, getting references, or searching for a job. When people are bad, it saves me time.

What's up with professionalism?

Really. I need to know. I've crossed the boundary between acceptable and unacceptable behavior, but never on a professional platform. I got in trouble for not wearing bras even though it's not part of my gender expression.

If I behaved like that at my last two office jobs, my supervisors would have fired me immediately. Some of the behavior I've seen is so outrageous, I can't believe these people have employment. Some are even leaders.

Like…how? Is hatred now normalized?

Please pay attention whether you're seeking for a job or even simply a side gig.

Do not add to the tragedy that LinkedIn comments can be, or at least don't make uninformed comments. Even if you weren't banned, the site may still bite you.

Recruiters can and do look at your activity. Your writing goes on your résumé. The wrong comment might lose you a job.

Recruiters and CEOs might reject candidates whose principles contradict with their corporate culture. Bigotry will get you banned from many companies, especially if others report you.

If you want a high-paying job, avoid being a LinkedIn asshole. People care even if you think no one does. Before speaking, ponder. Is this how you want to be perceived?

Better advice:

If your politics might turn off an employer, stop posting about them online and ask yourself why you hold such objectionable ideas.

GM Friens

The space had better days. Those greenish spikes...oh wow, haven't felt that in ages. Cryptocurrencies and NFTs have lost popularity. Google agrees. Both are declining.

As seen below, crypto interest spiked in May because of the Luna fall. NFT interest is similar to early October last year.

This makes me think NFTs are mostly hype and FOMO. No art or community. I've seen enough initiatives to know that communities stick around if they're profitable. Once it starts falling, they move on to the next project. The space has no long-term investments. Flip everything.

OpenSea trading volume has stayed steady for months. May's volume is 1.8 million ETH ($3.3 billion).

Despite this, I think NFTs and crypto will stick around. In bad markets, builders gain most.

Only 4k developers are active on Ethereum blockchain. It's low. A great chance for the space enthusiasts.

An employee of OpenSea might get a 40-year prison sentence for insider trading using NFTs.

Nathaniel Chastian, an OpenSea employee, traded on insider knowledge. He'll serve 40 years for that.

Here's what happened if you're unfamiliar.

OpenSea is a secondary NFT marketplace. Their homepage featured remarkable drops. Whatever gets featured there, NFT prices will rise 5x.

Chastian was at OpenSea. He chose forthcoming NFTs for OpenSeas' webpage.

Using anonymous digital currency wallets and OpenSea accounts, he would buy NFTs before promoting them on the homepage, showcase them, and then sell them for at least 25 times the price he paid.

From June through September 2021, this happened. Later caught, fired. He's charged with wire fraud and money laundering, each carrying a 20-year maximum penalty.

Although web3 space is all about decentralization, a step like this is welcomed since it restores faith in the area. We hope to see more similar examples soon.

Here's the press release.

Understanding smart contracts

@cantino.eth has a Twitter thread on smart contracts. Must-read. Also, he appears educated about the space, so follow him.