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

In the early 2000s, I began developing SaaS. I helped launch an internet fax service that delivered faxes to email inboxes. Back then, it saved consumers money and made the procedure easier.

Google AdWords was young then. Anyone might establish a new website, spend a few hundred dollars on keywords, and see dozens of new paying clients every day. That's how we launched our new SaaS, and these clients stayed for years. Our early ROI was sky-high.

Changing times

The situation changed dramatically after 15 years. Our paid advertising cost $200-$300 for every new customer. Paid advertising takes three to four years to repay.

Fortunately, we still had tens of thousands of loyal clients. Good organic rankings gave us new business. We needed less sponsored traffic to run a profitable SaaS firm.

Is it still possible?

Since selling our internet fax firm, I've dreamed about starting a SaaS company. One I could construct as a lone developer and progressively grow a dedicated customer base, as I did before in a small team.

It seemed impossible to me. Solo startups couldn't afford paid advertising. SEO was tough. Even the worst SaaS startup ideas attracted VC funding. How could I compete with startups that could hire great talent and didn't need to make money for years (or ever)?

The One and Only Way to Learn

After years of talking myself out of SaaS startup ideas, I decided to develop and launch one. I needed to know if a solitary developer may create a SaaS app in 2022.

Thus, I did. I invented webwriter.ai, an AI-powered writing tool for website content, from hero section headlines to blog posts, this year. I soft-launched an MVP in July.

Considering the Issue

Now that I've developed my own fully capable SaaS app for site builders and developers, I wonder if it's still possible. Can webwriter.ai be successful?

I know webwriter.ai's proposal is viable because Jasper.ai and Grammarly are also AI-powered writing tools. With competition comes validation.

To Win, Differentiate

To compete with well-funded established brands, distinguish to stand out to a portion of the market. So I can speak directly to a target user, unlike larger competition.

I created webwriter.ai to help web builders and designers produce web content rapidly. This may be enough differentiation for now.

Budget-Friendly Promotion

When paid search isn't an option, we get inventive. There are more tools than ever to promote a new website.

• Organic Results

• on social media (Twitter, Instagram, TikTok, LinkedIn)

• Marketing with content that is compelling

• Link Creation

• Listings in directories

• references made in blog articles and on other websites

• Forum entries

The Beginning of the Journey

As I've labored to construct my software, I've pondered a new mantra. Not sure where that originated from, but I like it. I'll live by it and teach my kids:

“Do the work.”

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.

No wonder brands use Twitter to reach their audience. 53% of Twitter users buy new products first. 

Twitter growth does more than make your brand look popular. It helps clients trust your business. It boosts your industry standing. It shows clients, prospects, and even competitors you mean business.

How can you naturally gain Twitter followers?

• Share useful information

• Post visual content

• Tweet consistently

• Socialize

• Spread your @name everywhere.

• Use existing customers

• Promote followers

Share useful information

Twitter users join conversations and consume material. To build your followers, make sure your material appeals to them and gives value, whether it's sales, product lessons, or current events.

Use Twitter Analytics to learn what your audience likes.

Explore popular topics by utilizing relevant keywords and hashtags. Check out this post on how to use Twitter trends.

Post visual content

97% of Twitter users focus on images, so incorporating media can help your Tweets stand out. Visuals and videos make content more engaging and memorable.

Tweet often

Your audience should expect regular content updates. Plan your ideas and tweet during crucial seasons and events with a content calendar.

Socialize

Twitter connects people. Do more than tweet. Follow industry leaders. Retweet influencers, engage with thought leaders, and reply to mentions and customers to boost engagement.

Micro-influencers can promote your brand or items. They can help you gain new audiences' trust.

Spread your @name everywhere.

Maximize brand exposure. Add a follow button on your website, link to it in your email signature and newsletters, and promote it on business cards or menus.

Use existing customers

Emails can be used to find existing Twitter clients. Upload your email contacts and follow your customers on Twitter to start a dialogue.

Promote followers

Run a followers campaign to boost your organic growth. Followers campaigns promote your account to a particular demographic, and you only pay when someone follows you.

Consider short campaigns to enhance momentum or an always-on campaign to gain new followers.

Increasing your brand's Twitter followers takes effort and experimentation, but the payback is huge.

👋 Follow me on twitter

Google announced 6% layoffs recently (or 12,000 people). This aligns it with most tech companies. A publicly contrite CEO explained that they had overhired during the COVID-19 pandemic boom and had to address it, but they were sorry and took full responsibility. I thought this was "bullshit" too. Meta, Amazon, Microsoft, and others must feel similarly. I spent 10 years at Google, and these things don't reflect well on the company's leaders.

All publicly listed companies have a fiduciary duty to act in the best interests of their shareholders. Dodge vs. Ford Motor Company established this (1919). Henry Ford wanted to reduce shareholder payments to offer cheaper cars and better wages. Ford stated.

My ambition is to employ still more men, to spread the benefits of this industrial system to the greatest possible number, to help them build up their lives and their homes. To do this we are putting the greatest share of our profits back in the business.

The Dodge brothers, who owned 10% of Ford, opposed this and sued Ford for the payments to start their own company. They won, preventing Ford from raising prices or salaries. If you have a vocal group of shareholders with the resources to sue you, you must prove you are acting in their best interests. Companies prioritize shareholders. Giving activist investors a stick to threaten you almost enshrines short-term profit over long-term thinking.

This underpins Google's current issues. Institutional investors who can sue Google see it as a wasteful company they can exploit. That doesn't mean you have to maximize profits (thanks to those who pointed out my ignorance of US corporate law in the comments and on HN), but it allows pressure. I feel for those navigating this. This is about unrestrained capitalism.

When Google went public, Larry Page and Sergey Brin knew the risks and worked hard to keep control. In their Founders' Letter to investors, they tried to set expectations for the company's operations.

Our long-term focus as a private company has paid off. Public companies do the same. We believe outside pressures lead companies to sacrifice long-term opportunities to meet quarterly market expectations.

The company has transformed since that letter. The company has nearly 200,000 full-time employees and a trillion-dollar market cap. Large investors have bought company stock because it has been a good long-term bet. Why are they restless now?

Other big tech companies emerged and fought for top talent. This has caused rising compensation packages. Google has also grown rapidly (roughly 22,000 people hired to the end of 2022). At $300,000 median compensation, those 22,000 people added $6.6 billion in salary overheads in 2022. Exorbitant. If the company still makes $16 billion every quarter, maybe not. Investors wonder if this value has returned.

Investors are right. Google uses people wastefully. However, by bluntly reducing headcount, they're not addressing the root causes and hurting themselves. No studies show that downsizing this way boosts productivity. There is plenty of evidence that they'll lose out because people will be risk-averse and distrust their leadership.

The company's approach also stinks. Finding out that you no longer have a job because you can’t log in anymore (sometimes in cases where someone is on call for protecting your production systems) is no way to fire anyone. Being with a narcissistic sociopath is like being abused. First, you receive praise and fancy perks for making the cut. You're fired by text and ghosted. You're told to appreciate the generous severance package. This firing will devastate managers and teams. This type of firing will take years to recover self-esteem. Senior management contributed to this. They chose the expedient answer, possibly by convincing themselves they were managing risk and taking the Macbeth approach of “If it were done when ’tis done, then ’twere well It were done quickly”.

Recap. Google's leadership did a stupid thing—mass firing—in a stupid way. How do we get rid of enough people to make investors happier? and "have 6% less people." Empathetic leaders should not emulate Elon Musk. There is no humane way to fire 12,000 people, but there are better ways. Why is Google so wasteful?

Ambition answers this. There aren't enough VP positions for a group of highly motivated, ambitious, and (increasingly) ruthless people. I’ve loitered around the edges of this world and a large part of my value was to insulate my teams from ever having to experience it. It’s like Game of Thrones played out through email and calendar and over video call.

Your company must look a certain way to be promoted to director or higher. You need the right people at the right levels under you. Long-term, growing your people will naturally happen if you're working on important things. This takes time, and you're never more than 6–18 months from a reorg that could start you over. Ambitious people also tend to be impatient. So, what do you do?

Hiring and vanity projects. To shape your company, you hire at the right levels. You value vanity metrics like active users over product utility. Your promo candidates get through by subverting the promotion process. In your quest for growth, you avoid performance managing people out. You avoid confronting toxic peers because you need their support for promotion. Your cargo cult gets you there.

Its ease makes Google wasteful. Since they don't face market forces, the employees don't see it as a business. Why would you do when the ads business is so profitable? Complacency causes senior leaders to prioritize their own interests. Empires collapse. Personal ambition often trumped doing the right thing for users, the business, or employees. Leadership's ambition over business is the root cause. Vanity metrics, mass hiring, and vague promises have promoted people to VP. Google goes above and beyond to protect senior leaders.

The decision-makers and beneficiaries are not the layoffees. Stock price increase beneficiaries. The people who will post on LinkedIn how it is about misjudging the market and how they’re so sorry and take full responsibility. While accumulating wealth, the dark room dwellers decide who stays and who goes. The billionaire investors. Google should start by addressing its bloated senior management, but — as they say — turkeys don't vote for Christmas. It should examine its wastefulness and make tough choices to fix it. A 6% cut is a blunt tool that admits you're not running your business properly. why aren’t the people running the business the ones shortly to be entering the job market?

This won't fix Google's wastefulness. The executives may never regain trust after their approach. Suppressed creativity. Business won't improve. Google will have lost its founding vision and us all. Large investors know they can force Google's CEO to yield. The rich will get richer and rationalize leaving 12,000 people behind. Cycles repeat.

It doesn’t have to be this way. In 2013, Nintendo's CEO said he wouldn't fire anyone for shareholders. Switch debuted in 2017. Nintendo's stock has increased by nearly five times, or 19% a year (including the drop most of the stock market experienced last year). Google wasted 12,000 talented people. To please rich people.