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

We love round numbers, don't we? $100,000 is a frequent freelancing milestone. You feel like six figures means you're doing something properly.

You've most likely already conquered initial freelancing challenges like finding clients, setting fair pricing, coping with criticism, getting through dry spells, managing funds, etc.

You think I must be doing well. Last month, my freelance income topped $100,000.

That may not sound impressive considering I've been freelancing for 2.75 years, but I made 30% of that in the previous four months, which is crazy.

Here are the things I wish I'd known during the early days of self-employment that would have helped me hit $100,000 faster.

1. The Volatility of Freelancing Will Stabilize.

Freelancing is risky. No surprise.

Here's an example.

October 2020 was my best month, earning $7,150. Between $4,004 in September and $1,730 in November. Unsteady.

Freelancing is regrettably like that. Moving clients. Content requirements change. Allocating so much time to personal pursuits wasn't smart, but yet.

Stabilizing income takes time. Consider my rolling three-month average income since I started freelancing. My three-month average monthly income. In February, this metric topped $5,000. Now, it's in the mid-$7,000s, but it took a while to get there.

Finding freelance gigs that provide high pay, high volume, and recurring revenue is difficult. But it's not impossible.

TLDR: Don't expect a steady income increase at first. Be patient.

2. You Have More Value Than You Realize.

Writing is difficult. Assembling words, communicating a message, and provoking action are a puzzle.

People are willing to pay you for it because they can't do what you do or don't have enough time.

Keeping that in mind can have huge commercial repercussions.

When talking to clients, don't tiptoe. You can ignore ridiculous deadlines. You don't have to take unmanageable work.

You solve an issue, so make sure you get rightly paid.

TLDR: Frame services as problem-solutions. This will let you charge more and set boundaries.

3. Increase Your Prices.

I studied hard before freelancing. I read articles and watched videos about writing businesses.

I didn't want to work for pennies. Despite this clarity, I had no real strategy to raise my rates.

I then luckily stumbled into higher-paying work. We discussed fees and hours with a friend who launched a consulting business. It's subjective and speculative because value isn't standardized. One company may laugh at your charges. If your solution helps them create a solid ROI, another client may pay $200 per hour.

When he told me he charged his first client $125 per hour, I thought, Why not?

A new-ish client wanted to discuss a huge forthcoming project, so I raised my rates. They knew my worth, so they didn't blink when I handed them my new number.

TLDR: Increase rates periodically (e.g., every 6 or 12 months). Writing skill develops with practice. You'll gain value over time.

4. Remember Your Limits.

If you can squeeze additional time into a day, let me know. I can't manipulate time yet.

We all have time and economic limits. You could theoretically keep boosting rates, but your prospect pool diminishes. Outsourcing and establishing extra revenue sources might boost monthly revenues.

I've devoted a lot of time to side projects (hopefully extra cash sources), but I've only just started outsourcing. I wish I'd tried this earlier.

If you can discover good freelancers, you can grow your firm without sacrificing time.

TLDR: Expand your writing network immediately. You'll meet freelancers who understand your daily grind and locate reference sources.

5. Every Action You Take Involves an Investment. Be Certain to Select Correctly.

Investing in stocks or crypto requires paying money, right?

In business, time is your currency (and maybe money too). Your daily habits define your future. If you spend time collecting software customers and compiling content in the space, you'll end up with both. So be sure.

I only spend around 50% of my time on client work, therefore it's taken me nearly three years to earn $100,000. I spend the remainder of my time on personal projects including a freelance book, an investment newsletter, and this blog.

Why? I don't want to rely on client work forever. So, I'm working on projects that could pay off later and help me live a more fulfilling life.

TLDR: Consider the long-term impact of your time commitments, and don't overextend. You can only make so many "investments" in a given time.

6. LinkedIn Is an Endless Mine of Gold. Use It.

Why didn't I use LinkedIn earlier?

I designed a LinkedIn inbound lead strategy that generates 12 leads a month and a few high-quality offers. As a result, I've turned down good gigs. Wish I'd begun earlier.

If you want to create a freelance business, prioritize LinkedIn. Too many freelancers ignore this site, missing out on high-paying clients. Build your profile, post often, and interact.

TLDR: Study LinkedIn's top creators. Once you understand their audiences, start posting and participating daily.

For 99% of People, Freelancing is Not a Get-Rich-Quick Scheme.

Here's a list of things I wish I'd known when I started freelancing.

1. Although it is erratic, freelancing eventually becomes stable.

2. You deserve respect and discretion over how you conduct business because you have solved an issue.

3. Increase your charges rather than undervaluing yourself. If necessary, add a reminder to your calendar. Your worth grows with time.

4. In order to grow your firm, outsource jobs. After that, you can work on the things that are most important to you.

5. Take into account how your present time commitments may affect the future. It will assist in putting things into perspective and determining whether what you are doing is indeed worthwhile.

6. Participate on LinkedIn. You'll get better jobs as a result.

If I could give my old self (and other freelancers) one bit of advice, it's this:

Despite appearances, you're making progress.

Each job. Tweets. Newsletters. Progress. It's simpler to see retroactively than in the moment.

Consistent, intentional work pays off. No good comes from doing nothing. You must set goals, divide them into time-based targets, and then optimize your calendar.

Then you'll understand you're doing well.

Want to learn more? I’ll teach you.

I recently wrote about getting VCs excited about Marketplace start-ups. SaaS founders became envious!

Understanding how people wire tens of millions is the only Series A hack I recommend.

Few people understand the intellectual process behind investing.

VC is risk management.

Series A-focused VCs must cover two risks.

1. Market risk

You need a large market to cross a threshold beyond which you can build defensibilities. Series A VCs underwrite market risk.

They must see you have reached product-market fit (PMF) in a large total addressable market (TAM).

2. Execution risk

When evaluating your growth engine's blitzscaling ability, execution risk arises.

When investors remove operational uncertainty, they profit.

Series A VCs like businesses with derisked revenue streams. Don't raise unless you have a predictable model, pipeline, and growth.

Please beat these 3 metrics before Series A:

Achieve $1.5m ARR in 12-24 months (Market risk)

Above 100% Net Dollar Retention. (Market danger)

Lead Velocity Rate supporting $10m ARR in 2–4 years (Execution risk)

Hit the 3 and you'll raise $10M in 4 months. Discussing 2/3 may take 6–7 months.

If none, don't bother raising and focus on becoming a capital-efficient business (Topics for other posts).

Let's examine these 3 metrics for the brave ones.

1. Lead Velocity Rate supporting €$10m ARR in 2 to 4 years

Last because it's the least discussed. LVR is the most reliable data when evaluating a growth engine, in my opinion.

SaaS allows you to see the future.

Monthly Sales and Sales Pipelines, two predictive KPIs, have poor data quality. Both are lagging indicators, and minor changes can cause huge modeling differences.

Analysts and Associates will trash your forecasts if they're based only on Monthly Sales and Sales Pipeline.

LVR, defined as month-over-month growth in qualified leads, is rock-solid. There's no lag. You can See The Future if you use Qualified Leads and a consistent formula and process to qualify them.

With this metric in your hand, scaling your company turns into an execution play on which VCs are able to perform calculations risk.

2. Above-100% Net Dollar Retention.

Net Dollar Retention is a better-known SaaS health metric than LVR.

Net Dollar Retention measures a SaaS company's ability to retain and upsell customers. Ask what $1 of net new customer spend will be worth in years n+1, n+2, etc.

Depending on the business model, SaaS businesses can increase their share of customers' wallets by increasing users, selling them more products in SaaS-enabled marketplaces, other add-ons, and renewing them at higher price tiers.

If a SaaS company's annualized Net Dollar Retention is less than 75%, there's a problem with the business.

Slack's ARR chart (below) shows how powerful Net Retention is. Layer chart shows how existing customer revenue grows. Slack's S1 shows 171% Net Dollar Retention for 2017–2019.

Slack S-1

3. $1.5m ARR in the last 12-24 months.

According to Point 9, $0.5m-4m in ARR is needed to raise a $5–12m Series A round.

Target at least what you raised in Pre-Seed/Seed. If you've raised $1.5m since launch, don't raise before $1.5m ARR.

Capital efficiency has returned since Covid19. After raising $2m since inception, it's harder to raise $1m in ARR.

P9's 2016-2021 SaaS Funding Napkin

In summary, less than 1% of companies VCs meet get funded. These metrics can help you win.

If there’s demand for it, I’ll do one on direct-to-consumer.

Cheers!

Start now.

When it comes to building my business, I’m passionate about a lot of things. I love creating user experiences that simplify branding essentials. I love creating new typefaces and color combinations to inspire logo designers. I love fixing problems to improve my product.

Business marketing isn't my thing.

This is shared by many. Many solopreneurs, like me, struggle to advertise their business and drive themselves to work on it.

Without a lot of promotion, no company will succeed. Marketing is 80% of developing a firm, and when you're starting out, it's even more. Some believe that you shouldn't build anything until you've begun marketing your idea and found enough buyers.

Marketing your business without marketing experience is difficult. There are various outlets and techniques to learn. Instead of figuring out where to start, it's easier to return to your area of expertise, whether that's writing, designing product features, or improving your site's back end. Right?

First, realize that your role as a founder is to market your firm. Being a founder focused on product, I rarely work on it.

Secondly, use these basic methods that have helped me dedicate adequate time and focus to marketing. They're all simple to apply, and they've increased my business's visibility and success.

1. Establish buckets for every task.

You've probably heard to schedule tasks you don't like. As simple as it sounds, blocking a substantial piece of my workday for marketing duties like LinkedIn or Twitter outreach, AppSumo customer support, or SEO has forced me to spend time on them.

Giving me lots of room to focus on product development has helped even more. Sure, this means scheduling time to work on product enhancements after my four-hour marketing sprint.

It also involves making space to store product inspiration and ideas throughout the day so I don't get distracted. This is like the advice to keep a notebook beside your bed to write down your insomniac ideas. I keep fonts, color palettes, and product ideas in folders on my desktop. Knowing these concepts won't be lost lets me focus on marketing in the moment. When I have limited time to work on something, I don't have to conduct the research I've been collecting, so I can get more done faster.

2. Look for various accountability systems

Accountability is essential for self-discipline. To keep focused on my marketing tasks, I've needed various streams of accountability, big and little.

Accountability groups are great for bigger things. SaaS Camp, a sales outreach coaching program, is mine. We discuss marketing duties and results every week. This motivates me to do enough each week to be proud of my accomplishments. Yet hearing what works (or doesn't) for others gives me benchmarks for my own marketing outcomes and plenty of fresh techniques to attempt.

… say, I want to DM 50 people on Twitter about my product — I get that many Q-tips and place them in one pen holder on my desk.

The best accountability group can't watch you 24/7. I use a friend's simple method that shouldn't work (but it does). When I have a lot of marketing chores, like DMing 50 Twitter users about my product, That many Q-tips go in my desk pen holder. After each task, I relocate one Q-tip to an empty pen holder. When you have a lot of minor jobs to perform, it helps to see your progress. You might use toothpicks, M&Ms, or anything else you have a lot of.

3. Continue to monitor your feedback loops

Knowing which marketing methods work best requires monitoring results. As an entrepreneur with little go-to-market expertise, every tactic I pursue is an experiment. I need to know how each trial is doing to maximize my time.

I placed Google and Facebook advertisements on hold since they took too much time and money to obtain Return. LinkedIn outreach has been invaluable to me. I feel that talking to potential consumers one-on-one is the fastest method to grasp their problem areas, figure out my messaging, and find product market fit.

Data proximity offers another benefit. Seeing positive results makes it simpler to maintain doing a work you don't like. Why every fitness program tracks progress.

Marketing's goal is to increase customers and revenues, therefore I've found it helpful to track those metrics and celebrate monthly advances. I provide these updates for extra accountability.

Finding faster feedback loops is also motivating. Marketing brings more clients and feedback, in my opinion. Product-focused founders love that feedback. Positive reviews make me proud that my product is benefitting others, while negative ones provide me with suggestions for product changes that can improve my business.

The best advice I can give a lone creator who's afraid of marketing is to just start. Start early to learn by doing and reduce marketing stress. Start early to develop habits and successes that will keep you going. The sooner you start, the sooner you'll have enough consumers to return to your favorite work.

This could cost you.

Content creators may have heard about Google's "Helpful content upgrade."

This change is another Google effort to remove low-quality, repetitive, and AI-generated content.

Why should content creators care?

Because too much content manipulates search results.

My experience includes the following.

Website admins seek high-quality guest posts from me. They send me AI-generated text after I say "yes." My readers are irrelevant. Backlinks are needed.

Companies copy high-ranking content to boost their Google rankings. Unfortunately, it's common.

What does this content offer?

Nothing.

Despite Google's updates and efforts to clean search results, webmasters create manipulative content.

As a marketer, I knew about AI-powered content generation tools. However, I've never tried them.

I use old-fashioned content creation methods to grow my website from 0 to 3,000 monthly views in one year.

Last year, I launched a niche website.

I do keyword research, analyze search intent and competitors' content, write an article, proofread it, and then optimize it.

This strategy is time-consuming.

But it yields results!

Here's proof from Google Analytics:

Proven strategies yield promising results.

To validate my assumptions and find new strategies, I run many experiments.

I tested an AI-powered content generator.

I used a tool to write this Google-optimized article about SEO for startups.

I wanted to analyze AI-generated content's Google performance.

Here are the outcomes of my test.

First, quality.

I dislike "meh" content. I expect articles to answer my questions. If not, I've wasted my time.

My essays usually include research, personal anecdotes, and what I accomplished and achieved.

AI-generated articles aren't as good because they lack individuality.

Read my AI-generated article about startup SEO to see what I mean.

It's dry and shallow, IMO.

It seems robotic.

I'd use quotes and personal experience to show how SEO for startups is different.

My article paraphrases top-ranked articles on a certain topic.

It's readable but useless. Similar articles abound online. Why read it?

AI-generated content is low-quality.

Let me show you how this content ranks on Google.

The Google Search Console report shows impressions, clicks, and average position.

Low numbers.

No one opens the 5th Google search result page to read the article. Too far!

You may say the new article will improve.

Marketing-wise, I doubt it.

This article is shorter and less comprehensive than top-ranking pages. It's unlikely to win because of this.

AI-generated content's terrible reality.

I'll compare how this content I wrote for readers and SEO performs.

Both the AI and my article are fresh, but trends are emerging.

My article's CTR and average position are higher.

I spent a week researching and producing that piece, unlike AI-generated content. My expert perspective and unique consequences make it interesting to read.

Human-made.

In summary

No content generator can duplicate a human's tone, writing style, or creativity. Artificial content is always inferior.

Not "bad," but inferior.

Demand for content production tools will rise despite Google's efforts to eradicate thin content.

Most won't spend hours producing link-building articles. Costly.

As guest and sponsored posts, artificial content will thrive.

Before accepting a new arrangement, content creators and website owners should consider this.

"Competition" is beautiful and hateful.

Some people bury their dreams because they are afraid of competition. Others challenge themselves, shaping our world.

Competition is normal.

It spurs innovation and progress.

I wish more people agreed.

As a marketer, content writer, and solopreneur, my readers often ask:

"I want to create a niche website, but I have no ideas. Everything's done"

"Is a website worthwhile?"

I can't count how many times I said, "Yes, it makes sense, and you can succeed in a competitive market."

I encourage and share examples, but it's not enough to overcome competition anxiety.

I launched an SEO writing website for content creators a year ago, knowing it wouldn't beat Ahrefs, Semrush, Backlinko, etc.

Not needed.

Many of my website's pages rank highly on Google.

Everyone can eat the pie.

In a competitive niche, I took a different approach.

Look farther

When chatting with bloggers that want a website, I discovered something fascinating.

They want to launch a website but have no ideas. As a next step, they start listing the interests they believe they should work on, like wellness, lifestyle, investments, etc. I could keep going.

Too many generalists who claim to know everything confuse many.

Generalists aren't trusted.

We want someone to fix our problems immediately.

I don't think broad-spectrum experts are undervalued. People have many demands that go beyond generalists' work. Narrow-niche experts can help.

I've done SEO for three years. I learned from experts and courses. I couldn't find a comprehensive SEO writing resource.

I read tons of articles before realizing that wasn't it. I took courses that covered SEO basics eventually.

I had a demand for learning SEO writing, but there was no solution on the market. My website fills this micro-niche.

Have you ever had trouble online?

Professional courses too general, boring, etc.?

You've bought off-topic books, right?

You're not alone.

Niche ideas!

Big players often disregard new opportunities. Too small. Individual content creators can succeed here.

In a competitive market:

• Never choose wide subjects

• Think about issues you can relate to and have direct experience with.

• Be a consumer to discover both the positive and negative aspects of a good or service.

• Merchandise your annoyances.

• Consider ways to transform your frustrations into opportunities.

The right niche is half-success. Here is what else I did to hit the Google front page with my website.

An innovative method for choosing subjects

Why publish on social media and websites?

Want likes, shares, followers, or fame?

Some people do it for fun. No judgment.

I bet you want more.

You want to make decent money from blogging.

Writing about random topics, even if they are related to your niche, won’t help you attract an audience from organic search. I'm a marketer and writer.

I worked at companies with dead blogs because they posted for themselves, not readers. They did not follow SEO writing rules; that’s why most of their content flopped.

I learned these hard lessons and grew my website from 0 to 3,000+ visitors per month while working on it a few hours a week only. Evidence:

I choose website topics using these criteria:

- Business potential. The information should benefit my audience and generate revenue. There would be no use in having it otherwise.

My topics should help me:

Attract organic search traffic with my "fluff-free" content -> Subscribers > SEO ebook sales.

Simple and effective.

- traffic on search engines. The number of monthly searches reveals how popular my topic is all across the world. If I find that no one is interested in my suggested topic, I don't write a blog article.

- Competition. Every search term is up against rivals. Some are more popular (thus competitive) since more websites target them in organic search. A new website won't score highly for keywords that are too competitive. On the other side, keywords with moderate to light competition can help you rank higher on Google more quickly.

- Search purpose. The "why" underlying users' search requests is revealed. I analyze search intent to understand what users need when they plug various queries in the search bar and what content can perfectly meet their needs.

My specialty website produces money, ranks well, and attracts the target audience because I handpick high-traffic themes.

Following these guidelines, even a new website can stand out.

I wrote a 50-page SEO writing guide where I detailed topic selection and share my front-page Google strategy.

My guide can help you run a successful niche website.

In summary

You're not late to the niche-website party.

The Internet offers many untapped opportunities.

We need new solutions and are willing to listen.

There are unexplored niches in any topic.

Don't fight giants. They have their piece of the pie. They might overlook new opportunities while trying to keep that piece of the pie. You should act now.