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.

My growth-killing mistake

When you initially start developing your audience, you need guidance.

What does my audience like? What do they not like? How can I grow more?

When I started writing two years ago, I inquired daily. Taking cues from your audience to develop more valuable content is a good concept, but it's simple to let them destroy your growth.

A small audience doesn't represent the full picture.

When I had fewer than 100 YouTube subscribers, I tried several video styles and topics. I looked to my audience for what to preserve and what to change.

If my views, click-through rate, or average view % dropped, that topic or style was awful. Avoiding that style helped me grow.

Vlogs, talking head videos on writing, and long-form tutorials didn't fare well.

Since I was small, I've limited the types of films I make. I have decided to make my own videos.

Surprisingly, the videos I avoided making meet or exceed my views, CTR, and audience retention.

A limited audience can't tell you what your tribe wants. Therefore, limiting your innovation will prohibit you from reaching the right audience. Finding them may take longer.

Large Creators Experience The Same Issue

In the last two years, I've heard Vanessa Lau and Cathrin Manning say they felt pigeonholed into generating videos they didn't want to do.

Why does this happen over and over again?

Once you have a popular piece of content, your audience will grow. So when you publish inconsistent material, fewer of your new audience will view it. You interpret the drop in views as a sign that your audience doesn't want the content, so you stop making it.

Repeat this procedure a few times, and you'll create stuff you're not passionate about because you're frightened to publish it.

How to Manage Your Creativity and Audience Development

I'm not recommending you generate random content.

Instead of feeling trapped by your audience, you can cultivate a diverse audience.

Create quality material on a range of topics and styles as you improve. Be creative until you get 100 followers. Look for comments on how to improve your article.

If you observe trends in the types of content that expand your audience, focus 50-75% of your material on those trends. Allow yourself to develop 25% non-performing material.

This method can help you expand your audience faster with your primary trends and like all your stuff. Slowly, people will find 25% of your material, which will boost its performance.

How to Expand Your Audience Without Having More Limited Content

Follow these techniques to build your audience without feeling confined.

• Don't think that you need restrict yourself to what your limited audience prefers.

• Don't let the poor performance of your desired material demotivate you.

• You shouldn't restrict the type of content you publish or the themes you cover when you have less than 100 followers.

• When your audience expands, save 25% of your content for your personal interests, regardless of how well it does.

I relocated my notes database from Roam Research to Obsidian earlier this year expecting to stay there for a long. Obsidian is a terrific tool, and I explained my move in that post.

Moving everything to Tana faster than intended. Tana? Why?

Tana is just another note-taking app, but it does it differently. Three note-taking apps existed before Tana:

1. simple note-taking programs like Apple Notes and Google Keep.

2. Roam Research and Obsidian are two graph-style applications that assisted connect your notes.

3. You can create effective tables and charts with data-focused tools like Notion and Airtable.

Tana is the first great software I've encountered that combines graph and data notes. Google Keep will certainly remain my rapid notes app of preference. This Shu Omi video gives a good overview:

Tana handles everything I did in Obsidian with books, people, and blog entries, plus more. I can find book quotes, log my workouts, and connect my thoughts more easily. It should make writing blog entries notes easier, so we'll see.

Tana is now invite-only, but if you're interested, visit their site and sign up. As Shu noted in the video above, the product hasn't been published yet but seems quite polished.

Whether I stay with Tana or not, I'm excited to see where these apps are going and how they can benefit us all.

Hiring is difficult, but you shouldn't compromise on team members. Or it may suggest you need to look beyond years in a similar role/function.

Every hire should be someone we'd want as one of our first ten employees.

If you hire such people, your team will adapt, initiate, and problem-solve, and your company will grow. You'll stay nimble even as you scale, and you'll learn from your colleagues.

If you only hire for a specific role or someone who can execute the job, you'll become a cluster of optimizers, and talent will depart for a more fascinating company. A startup is continually changing, therefore you want individuals that embrace it.

As a leader, establishing ideal conditions for talent and having a real ideology should be high on your agenda. You can't eliminate attrition, nor would you want to, but you can hire people who will become your company's leaders.

In my last four jobs I was employee 2, 5, 3, and 5. So while this is all a bit self serving, you’re the one reading my writing — and I have some experience with who works out in the first ten!

First, we'll examine what they do well (and why they're beneficial for startups), then what they don't, and how to hire them.

First 10 are:

• Business partners: Because it's their company, they take care of whatever has to be done and have ideas about how to do it. You can rely on them to always put the success of the firm first because it is their top priority (company success is strongly connected with success for early workers). This approach will eventually take someone to leadership positions.
  

• High Speed Learners: They process knowledge quickly and can reach 80%+ competency in a new subject matter rather quickly. A growing business that is successful tries new things frequently. We have all lost a lot of money and time on employees who follow the wrong playbook or who wait for someone else within the company to take care of them.
  

• Autodidacts learn by trial and error, osmosis, networking with others, applying first principles, and reading voraciously (articles, newsletters, books, and even social media). Although teaching is wonderful, you won't have time.
  

• Self-scaling: They figure out a means to deal with issues and avoid doing the grunt labor over the long haul, increasing their leverage. Great people don't keep doing the same thing forever; as they expand, they use automation and delegation to fill in their lower branches. This is a crucial one; even though you'll still adore them, you'll have to manage their scope or help them learn how to scale on their own.
  

• Free Range: You can direct them toward objectives rather than specific chores. Check-ins can be used to keep them generally on course without stifling invention instead of giving them precise instructions because doing so will obscure their light.
  

• When people are inspired, they bring their own ideas about what a firm can be and become animated during discussions about how to get there.
  

• Novelty Seeking: They look for business and personal growth chances. Give them fresh assignments and new directions to follow around once every three months.

Here’s what the First Ten types may not be:

• Domain specialists. When you look at their resumes, you'll almost certainly think they're unqualified. Fortunately, a few strategically positioned experts may empower a number of First Ten types by serving on a leadership team or in advising capacities.
  

• Balanced. These people become very invested, and they may be vulnerable to many types of stress. You may need to assist them in managing their own stress and coaching them through obstacles. If you are reading this and work at Banza, I apologize for not doing a better job of supporting this. I need to be better at it.
  

• Able to handle micromanagement with ease. People who like to be in charge will suppress these people. Good decision-making should be delegated to competent individuals. Generally speaking, if you wish to scale.

Great startup team members have versatility, learning, innovation, and energy. When we hire for the function, not the person, we become dull and staid. Could this person go to another department if needed? Could they expand two levels in a few years?

First Ten qualities and experience level may have a weak inverse association. People with 20+ years of experience who had worked at larger organizations wanted to try something new and had a growth mentality. College graduates may want to be told what to do and how to accomplish it so they can stay in their lane and do what their management asks.

Does the First Ten archetype sound right for your org? Cool, let’s go hiring. How will you know when you’ve found one?

• They exhibit adaptive excellence, excelling at a variety of unrelated tasks. It could be hobbies or professional talents. This suggests that they will succeed in the next several endeavors they pursue.
  

• Successful risk-taking is doing something that wasn't certain to succeed, sometimes more than once, and making it do so. It's an attitude.
  

• Rapid Rise: They regularly change roles and get promoted. However, they don't leave companies when the going gets tough. Look for promotions at every stop and at least one position with three or more years of experience.

You can ask them:

• Tell me about a time when you started from scratch or achieved success. What occurred en route? You might request a variety of tales from various occupations or even aspects of life. They ought to be energized by this.
  

• What new skills have you just acquired? It is not required to be work-related. They must be able to describe it and unintentionally become enthusiastic about it.
  

• Tell me about a moment when you encountered a challenge and had to alter your strategy. The core of a startup is reinventing itself when faced with obstacles.
  

• Tell me about a moment when you eliminated yourself from a position at work. They've demonstrated they can permanently solve one issue and develop into a new one, as stated above.
  

• Why do you want to leave X position or Y duty? These people ought to be moving forward, not backward, all the time. Instead, they will discuss what they are looking forward to visiting your location.
  

• Any questions? Due to their inherent curiosity and desire to learn new things, they should practically never run out of questions. You can really tell if they are sufficiently curious at this point.

People who see their success as being the same as the success of the organization are the best-case team members, in any market. They’ll grow and change with the company, and always try to prioritize what matters. You’ll find yourself more energized by your work because you’re surrounded by others who are as well. Happy teambuilding!

Only two of the following three options can be achieved: consistency, availability, and partition tolerance

Someone told me that growing from 30 to 60 is the biggest adjustment for a team or business.

I remember thinking, That's random. Each company is unique. I've seen teams of all types confront the same issues during development periods. With new enterprises starting every year, we should be better at navigating growing difficulties.

As a team grows, its processes and systems break down, requiring reorganization or declining results. Why always? Why isn't there a perfect scaling model? Why hasn't that been found?

The Three Things Productive Organizations Must Have

Any company should be efficient and productive. Three items are needed:

First, it must verify that no two team members have conflicting information about the roadmap, strategy, or any input that could affect execution. Teamwork is required.

Second, it must ensure that everyone can receive the information they need from everyone else quickly, especially as teams become more specialized (an inevitability in a developing organization). It requires everyone's accessibility.

Third, it must ensure that the organization can operate efficiently even if a piece is unavailable. It's partition-tolerant.

From my experience with the many teams I've been on, invested in, or advised, achieving all three is nearly impossible. Why a perfect organization model cannot exist is clear after analysis.

The CAP Theorem: What is it?

Eric Brewer of Berkeley discovered the CAP Theorem, which argues that a distributed data storage should have three benefits. One can only have two at once.

The three benefits are consistency, availability, and partition tolerance, which implies that even if part of the system is offline, the remainder continues to work.

This notion is usually applied to computer science, but I've realized it's also true for human organizations. In a post-COVID world, many organizations are hiring non-co-located staff as they grow. CAP Theorem is more important than ever. Growing teams sometimes think they can develop ways to bypass this law, dooming themselves to a less-than-optimal team dynamic. They should adopt CAP to maximize productivity.

Path 1: Consistency and availability equal no tolerance for partitions

Let's imagine you want your team to always be in sync (i.e., for someone to be the source of truth for the latest information) and to be able to share information with each other. Only division into domains will do.

Numerous developing organizations do this, especially after the early stage (say, 30 people) when everyone may wear many hats and be aware of all the moving elements. After a certain point, it's tougher to keep generalists aligned than to divide them into specialized tasks.

In a specialized, segmented team, leaders optimize consistency and availability (i.e. every function is up-to-speed on the latest strategy, no one is out of sync, and everyone is able to unblock and inform everyone else).

Partition tolerance suffers. If any component of the organization breaks down (someone goes on vacation, quits, underperforms, or Gmail or Slack goes down), productivity stops. There's no way to give the team stability, availability, and smooth operation during a hiccup.

Path 2: Partition Tolerance and Availability = No Consistency

Some businesses avoid relying too heavily on any one person or sub-team by maximizing availability and partition tolerance (the organization continues to function as a whole even if particular components fail). Only redundancy can do that. Instead of specializing each member, the team spreads expertise so people can work in parallel. I switched from Path 1 to Path 2 because I realized too much reliance on one person is risky.

What happens after redundancy? Unreliable. The more people may run independently and in parallel, the less anyone can be the truth. Lack of alignment or updated information can lead to people executing slightly different strategies. So, resources are squandered on the wrong work.

Path 3: Partition and Consistency "Tolerance" equates to "absence"

The third, least-used path stresses partition tolerance and consistency (meaning answers are always correct and up-to-date). In this organizational style, it's most critical to maintain the system operating and keep everyone aligned. No one is allowed to read anything without an assurance that it's up-to-date (i.e. there’s no availability).

Always short-lived. In my experience, a business that prioritizes quality and scalability over speedy information transmission can get bogged down in heavy processes that hinder production. Large-scale, this is unsustainable.

Accepting CAP

When two puzzle pieces fit, the third won't. I've watched developing teams try to tackle these difficulties, only to find, as their ancestors did, that they can never be entirely solved. Idealized solutions fail in reality, causing lost effort, confusion, and lower production.

As teams develop and change, they should embrace CAP, acknowledge there is a limit to productivity in a scaling business, and choose the best two-out-of-three path.