Are you an idiot at fundraising?

Humans undervalue what they don't grasp. Consider NASCAR. How is that a sport? ask uneducated observers. Circular traffic. Driving near a car's physical limits is different from daily driving. When driving at 200 mph, seemingly simple things like changing gas weight or asphalt temperature might be life-or-death.

Venture investors do something similar in entrepreneurship. Most entrepreneurs don't realize how complex venture finance is.

In my early startup days, I didn't comprehend venture capital's intricacy. I thought VCs were rich folks looking for the next Mark Zuckerberg. I was meant to be a sleek, enthusiastic young entrepreneur who could razzle-dazzle investors.

Finally, one of the VCs I was trying to woo set me straight. He insulted me.

How I learned that I was approaching the wrong investor

I was constructing a consumer-facing, pre-revenue marketplace firm. I looked for investors in my old university's alumni database. My city had one. After some research, I learned he was a partner at a growth-stage, energy-focused VC company with billions under management.

Billions? I thought. Surely he can write a million-dollar cheque. He'd hardly notice.

I emailed the VC about our shared alumni status, explaining that I was building a startup in the area and wanted advice. When he agreed to meet the next week, I prepared my pitch deck.

First error.

The meeting seemed like a funding request. Imagine the awkwardness.

His assistant walked me to the firm's conference room and told me her boss was running late. While waiting, I prepared my pitch. I connected my computer to the projector, queued up my PowerPoint slides, and waited for the VC.

He didn't say hello or apologize when he entered a few minutes later. What are you doing?

Hi! I said, Confused but confident. Dinin Aaron. My startup's pitch.

Who? Suspicious, he replied. Your email says otherwise. You wanted help.

I said, "Isn't that a euphemism for contacting investors?" Fundraising I figured I should pitch you.

As he sat down, he smiled and said, "Put away your computer." You need to study venture capital.

Recognizing the business aspects of venture capital

The VC taught me venture capital in an hour. Young entrepreneur me needed this lesson. I assume you need it, so I'm sharing it.

Most people view venture money from an entrepreneur's perspective, he said. They envision a world where venture capital serves entrepreneurs and startups.

As my VC indicated, VCs perceive their work differently. Venture investors don't serve entrepreneurs. Instead, they run businesses. Their product doesn't look like most products. Instead, the VCs you're proposing have recognized an undervalued market segment. By investing in undervalued companies, they hope to profit. It's their investment thesis.

Your company doesn't fit my investment thesis, the venture capitalist told me. Your pitch won't beat my investing theory. I invest in multimillion-dollar clean energy companies. Asking me to invest in you is like ordering a breakfast burrito at a fancy steakhouse. They could, but why? They don't do that.

Yeah, I’m not a fine steak yet, I laughed, feeling like a fool for pitching a growth-stage VC used to looking at energy businesses with millions in revenues on my pre-revenue, consumer startup.

He stressed that it's not necessary. There are investors targeting your company. Not me. Find investors and pitch them.

Remember this when fundraising. Your investors aren't philanthropists who want to help entrepreneurs realize their company goals. Venture capital is a sophisticated investment strategy, and VC firm managers are industry experts. They're looking for companies that meet their investment criteria. As a young entrepreneur, I didn't grasp this, which is why I struggled to raise money. In retrospect, I probably seemed like an idiot. Hopefully, you won't after reading this.

I read 53 novels last year and hope to do so again.

Books are best if you love learning. You get a range of perspectives, unlike podcasts and YouTube channels where you get the same ones.

Book quality varies. I've read useless books. Most books teach me something.

These 9 novels have changed my outlook in recent years. They've made me rethink what I believed or introduced me to a fresh perspective that changed my worldview.

You can order these books yourself. Or, read my summaries to learn what I've synthesized.

Enjoy!

Fooled By Randomness

Nassim Taleb worked as a Wall Street analyst. He used options trading to bet on unlikely events like stock market crashes.

Using financial models, investors predict stock prices. The models assume constant, predictable company growth.

These models base their assumptions on historical data, so they assume the future will be like the past.

Fooled By Randomness argues that the future won't be like the past. We often see impossible market crashes like 2008's housing market collapse. The world changes too quickly to use historical data: by the time we understand how it works, it's changed.

Most people don't live to see history unfold. We think our childhood world will last forever. That goes double for stable societies like the U.S., which hasn't seen major turbulence in anyone's lifetime.

Fooled By Randomness taught me to expect the unexpected. The world is deceptive and rarely works as we expect. You can't always trust your past successes or what you've learned.

Antifragile

More Taleb. Some things, like the restaurant industry and the human body, improve under conditions of volatility and turbulence.

We didn't have a word for this counterintuitive concept until Taleb wrote Antifragile. The human body (which responds to some stressors, like exercise, by getting stronger) and the restaurant industry both benefit long-term from disorder (when economic turbulence happens, bad restaurants go out of business, improving the industry as a whole).

Many human systems are designed to minimize short-term variance because humans don't understand it. By eliminating short-term variation, we increase the likelihood of a major disaster.

Once, we put out every forest fire we found. Then, dead wood piled up in forests, causing catastrophic fires.

We don't like price changes, so politicians prop up markets with stimulus packages and printing money. This leads to a bigger crash later. Two years ago, we printed a ton of money for stimulus checks, and now we have double-digit inflation.

Antifragile taught me how important Plan B is. A system with one or two major weaknesses will fail. Make large systems redundant, foolproof, and change-responsive.

Reality is broken

We dread work. Work is tedious. Right?

Wrong. Work gives many people purpose. People are happiest when working. (That's why some are workaholics.)

Factory work saps your soul, office work is boring, and working for a large company you don't believe in and that operates unethically isn't satisfying.

Jane McGonigal says in Reality Is Broken that meaningful work makes us happy. People love games because they simulate good work. McGonigal says work should be more fun.

Some think they'd be happy on a private island sipping cocktails all day. That's not true. Without anything to do, most people would be bored. Unemployed people are miserable. Many retirees die within 2 years, much more than expected.

Instead of complaining, find meaningful work. If you don't like your job, it's because you're in the wrong environment. Find the right setting.

The Lean Startup

Before the airplane was invented, Harvard scientists researched flying machines. Who knew two North Carolina weirdos would beat them?

The Wright Brothers' plane design was key. Harvard researchers were mostly theoretical, designing an airplane on paper and trying to make it fly in theory. They'd build it, test it, and it wouldn't fly.

The Wright Brothers were different. They'd build a cheap plane, test it, and it'd crash. Then they'd learn from their mistakes, build another plane, and it'd crash.

They repeated this until they fixed all the problems and one of their planes stayed aloft.

Mistakes are considered bad. On the African savannah, one mistake meant death. Even today, if you make a costly mistake at work, you'll be fired as a scapegoat. Most people avoid failing.

In reality, making mistakes is the best way to learn.

Eric Reis offers an unintuitive recipe in The Lean Startup: come up with a hypothesis, test it, and fail. Then, try again with a new hypothesis. Keep trying, learning from each failure.

This is a great startup strategy. Startups are new businesses. Startups face uncertainty. Run lots of low-cost experiments to fail, learn, and succeed.

Don't fear failing. Low-cost failure is good because you learn more from it than you lose. As long as your worst-case scenario is acceptable, risk-taking is good.

The Sovereign Individual

Today, nation-states rule the world. The UN recognizes 195 countries, and they claim almost all land outside of Antarctica.

We agree. For the past 2,000 years, much of the world's territory was ungoverned.

Why today? Because technology has created incentives for nation-states for most of the past 500 years. The logic of violence favors nation-states, according to James Dale Davidson, author of the Sovereign Individual. Governments have a lot to gain by conquering as much territory as possible, so they do.

Not always. During the Dark Ages, Europe was fragmented and had few central governments. Partly because of armor. With armor, a sword, and a horse, you couldn't be stopped. Large states were hard to form because they rely on the threat of violence.

When gunpowder became popular in Europe, violence changed. In a world with guns, assembling large armies and conquest are cheaper.

James Dale Davidson says the internet will make nation-states obsolete. Most of the world's wealth will be online and in people's heads, making capital mobile.

Nation-states rely on predatory taxation of the rich to fund large militaries and welfare programs.

When capital is mobile, people can live anywhere in the world, Davidson says, making predatory taxation impossible. They're not bound by their job, land, or factory location. Wherever they're treated best.

Davidson says that over the next century, nation-states will collapse because they won't have enough money to operate as they do now. He imagines a world of small city-states, like Italy before 1900. (or Singapore today).

We've already seen some movement toward a more Sovereign Individual-like world. The pandemic proved large-scale remote work is possible, freeing workers from their location. Many cities and countries offer remote workers incentives to relocate.

Many Western businesspeople live in tax havens, and more people are renouncing their US citizenship due to high taxes. Increasing globalization has led to poor economic conditions and resentment among average people in the West, which is why politicians like Trump and Sanders rose to popularity with angry rhetoric, even though Obama rose to popularity with a more hopeful message.

The Sovereign Individual convinced me that the future will be different than Nassim Taleb's. Large countries like the U.S. will likely lose influence in the coming decades, while Portugal, Singapore, and Turkey will rise. If the trend toward less freedom continues, people may flee the West en masse.

So a traditional life of college, a big firm job, hard work, and corporate advancement may not be wise. Young people should learn as much as possible and develop flexible skills to adapt to the future.

Sapiens

Sapiens is a history of humanity, from proto-humans in Ethiopia to our internet society today, with some future speculation.

Sapiens views humans (and Homo sapiens) as a unique species on Earth. We were animals 100,000 years ago. We're slowly becoming gods, able to affect the climate, travel to every corner of the Earth (and the Moon), build weapons that can kill us all, and wipe out thousands of species.

Sapiens examines what makes Homo sapiens unique. Humans can believe in myths like religion, money, and human-made entities like countries and LLCs.

These myths facilitate large-scale cooperation. Ants from the same colony can cooperate. Any two humans can trade, though. Even if they're not genetically related, large groups can bond over religion and nationality.

Combine that with intelligence, and you have a species capable of amazing feats.

Sapiens may make your head explode because it looks at the world without presupposing values, unlike most books. It questions things that aren't usually questioned and says provocative things.

It also shows how human history works. It may help you understand and predict the world. Maybe.

The 4-hour Workweek

Things can be done better.

Tradition, laziness, bad bosses, or incentive structures cause complacency. If you're willing to make changes and not settle for the status quo, you can do whatever you do better and achieve more in less time.

The Four-Hour Work Week advocates this. Tim Ferriss explains how he made more sales in 2 hours than his 8-hour-a-day colleagues.

By firing 2 of his most annoying customers and empowering his customer service reps to make more decisions, he was able to leave his business and travel to Europe.

Ferriss shows how to escape your 9-to-5, outsource your life, develop a business that feeds you with little time, and go on mini-retirement adventures abroad.

Don't accept the status quo. Instead, level up. Find a way to improve your results. And try new things.

Why Nations Fail

Nogales, Arizona and Mexico were once one town. The US/Mexico border was arbitrarily drawn.

Both towns have similar cultures and populations. Nogales, Arizona is well-developed and has a high standard of living. Nogales, Mexico is underdeveloped and has a low standard of living. Whoa!

Why Nations Fail explains how government-created institutions affect country development. Strong property rights, capitalism, and non-corrupt governments promote development. Countries without capitalism, strong property rights, or corrupt governments don't develop.

Successful countries must also embrace creative destruction. They must offer ordinary citizens a way to improve their lot by creating value for others, not reducing them to slaves, serfs, or peasants. Authors say that ordinary people could get rich on trading expeditions in 11th-century Venice.

East and West Germany and North and South Korea have different economies because their citizens are motivated differently. It explains why Chile, China, and Singapore grow so quickly after becoming market economies.

People have spent a lot of money on third-world poverty. According to Why Nations Fail, education and infrastructure aren't the answer. Developing nations must adopt free-market economic policies.

Elon Musk

Elon Musk is the world's richest man, but that’s not a good way to describe him. Elon Musk is the world's richest man, which is like calling Steve Jobs a turtleneck-wearer or Benjamin Franklin a printer.

Elon Musk does cool sci-fi stuff to help humanity avoid existential threats.

Oil will run out. We've delayed this by developing better extraction methods. We only have so much nonrenewable oil.

Our society is doomed if it depends on oil. Elon Musk invested heavily in Tesla and SolarCity to speed the shift to renewable energy.

Musk worries about AI: we'll build machines smarter than us. We won't be able to stop these machines if something goes wrong, just like cows can't fight humans. Neuralink: we need to be smarter to compete with AI when the time comes.

If Earth becomes uninhabitable, we need a backup plan. Asteroid or nuclear war could strike Earth at any moment. We may not have much time to react if it happens in a few days. We must build a new civilization while times are good and resources are plentiful.

Short-term problems dominate our politics, but long-term issues are more important. Long-term problems can cause mass casualties and homelessness. Musk demonstrates how to think long-term.

The main reason people are impressed by Elon Musk, and why Ashlee Vances' biography influenced me so much, is that he does impossible things.

Electric cars were once considered unprofitable, but Tesla has made them mainstream. SpaceX is the world's largest private space company.

People lack imagination and dismiss ununderstood ideas as impossible. Humanity is about pushing limits. Don't worry if your dreams seem impossible. Try it.

Thanks for reading.

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.