If I could tell my younger self a few rules, they would boost my career.

1. Treat design like medicine; don't get attached.

If it doesn't help, you won't be angry, but you'll try to improve it. Designers blame others if they don't like the design, but the rule is the same: we solve users' problems. You're not your design, and neither are they. Be humble with your work because your assumptions will often be wrong and users will behave differently.

2. Consider your design flawed.

Disagree with yourself, then defend your ideas. Most designers forget to dig deeper into a pattern, screen, button, or copywriting. If someone asked, "Have you considered alternatives? How does this design stack up? Here's a functional UX checklist to help you make design decisions.

3. Codeable solutions.

If your design requires more developer time, consider whether it's worth spending more money to code something with a small UX impact. Overthinking problems and designing abstract patterns is easy. Sometimes you see something on dribbble or bechance and try to recreate it, but it's not worth it. Here's my article on it.

4. Communication changes careers

Designers often talk with users, clients, companies, developers, and other designers. How you talk and present yourself can land you a job. Like driving or swimming, practice it. Success requires being outgoing and friendly. If I hadn't said "hello" to a few people, I wouldn't be where I am now.

5. Ignorance of the law is not an excuse.

Copyright, taxation How often have you used an icon without checking its license? If you use someone else's work in your project, the owner can cause you a lot of problems — paying a lot of money isn't worth it. Spend a few hours reading about copyrights, client agreements, and taxes.

6. Always test your design

If nobody has seen or used my design, it's not finished. Ask friends about prototypes. Testing reveals how wrong your assumptions were. Steve Krug, one of the authorities on this topic will tell you more about how to do testing.

7. Run workshops

A UX designer's job involves talking to people and figuring out what they need, which is difficult because they usually don't know. Organizing teamwork sessions is a powerful skill, but you must also be a good listener. Your job is to help a quiet, introverted developer express his solution and control the group. AJ Smart has more on workshops here.

A reading list for successful people

Elon Musk reads and talks. So, one learns. Many brilliant individuals & amazing literature.

This article recommends 3 Elon Musk novels. All of them helped me succeed. Hope they'll help you.

Douglas Adams's The Hitchhiker's Guide to the Galaxy

Page Count: 193
Rating on Goodreads: 4.23

Arthur Dent is pulled off Earth by a buddy seconds before it's razed for a cosmic motorway. The trio hitchhikes through space and gets into problems.

I initially read Hitchhiker's as a child. To evade my mum, I'd read with a flashlight under the covers. She'd scold at me for not sleeping on school nights when she found out. Oops.

The Hitchhiker's Guide to the Galaxy is lighthearted science fiction.

My favorite book quotes are:

• “Space is big. You won’t believe how vastly, hugely, mind-bogglingly big it is. I mean, you may think it’s a long way down the road to the chemist’s, but that’s just peanuts to space.”

• “Far out in the uncharted backwaters of the unfashionable end of the western spiral arm of the Galaxy lies a small unregarded yellow sun. Orbiting this at a distance of roughly ninety-two million miles is an utterly insignificant little blue-green planet whose ape-descended life forms are so amazingly primitive that they still think digital watches are a pretty neat idea.”

• “On planet Earth, man had always assumed that he was more intelligent than dolphins because he had achieved so much — the wheel, New York, wars, and so on — whilst all the dolphins had ever done was muck about in the water having a good time. But conversely, the dolphins had always believed that they were far more intelligent than man — for precisely the same reasons.”

the Sun Tzu book The Art Of War

Page Count: 273
Rating on Goodreads: 3.97

It's a classic. You may apply The Art of War's ideas to (nearly) every facet of life. Ex:

• Pick your fights.

• Keep in mind that timing is crucial.

• Create a backup plan in case something goes wrong.

• Obstacles provide us a chance to adapt and change.

This book was my first. Since then, I'm a more strategic entrepreneur. Excellent book. And read it ASAP!

My favorite book quotes are:

• “Victorious warriors win first and then go to war, while defeated warriors go to war first and then seek to win.”

• “Engage people with what they expect; it is what they are able to discern and confirms their projections. It settles them into predictable patterns of response, occupying their minds while you wait for the extraordinary moment — that which they cannot anticipate.”

• “If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained, you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle.”

Peter Thiel's book Zero to One

Page Count: 195
Rating on Goodreads: 4.18

Peter argues the best money-making strategies are typically unproven. Entrepreneurship should never have a defined path to success. Whoever says differently is lying.

Zero to One explores technology and society. Peter is a philosophy major and law school graduate, which informs the work.

Peters' ideas, depth, and intellect stood out in Zero to One. It's a top business book.

My favorite book quotes are:

• “The most valuable businesses of coming decades will be built by entrepreneurs who seek to empower people rather than try to make them obsolete.”

• “The next Bill Gates will not build an operating system. The next Larry Page or Sergey Brin won’t make a search engine. And the next Mark Zuckerberg won’t create a social network. If you are copying these guys, you aren’t learning from them.”

• “If your goal is to never make a mistake in your life, you shouldn’t look for secrets. The prospect of being lonely but right — dedicating your life to something that no one else believes in — is already hard. The prospect of being lonely and wrong can be unbearable.”

Don’t give a number

Google pays its software engineers generously. While many of their employees are competent, they disregard a critical skill to maximize their pay.

Negotiation.

If Google employees have never negotiated, they're as helpless as anyone else.

In this piece, I'll reveal a compensation negotiation tip that will set you apart.

The Fallacy of Negotiating

How do you negotiate your salary? “Just give them a number twice the amount you really want”. - Someplace on the internet

Above is typical negotiation advice. If you ask for more than you want, the recruiter may meet you halfway.

It seems logical and great, but here's why you shouldn't follow that advice.

Haitian hostage rescue

In 1977, an official's aunt was kidnapped in Haiti. The kidnappers demanded $150,000 for the aunt's life. It seems reasonable until you realize why kidnappers want $150,000.

FBI detective and negotiator Chris Voss researched why they demanded so much.

“So they could party through the weekend”

When he realized their ransom was for partying, he offered $4,751 and a CD stereo. Criminals freed the aunt.

These thieves gave 31.57x their estimated amount and got a fraction. You shouldn't trust these thieves to negotiate your compensation.

What happened?

Negotiating your offer and Haiti

This narrative teaches you how to negotiate with a large number.

You can and will be talked down.

If a recruiter asks your wage expectation and you offer double, be ready to explain why.

If you can't justify your request, you may be offered less. The recruiter will notice and talk you down.

Reasonably,

• a tiny bit more than the present amount you earn

• a small premium over an alternative offer

• a little less than the role's allotted amount

Real-World Illustration

Recruiter: What’s your expected salary? Candidate: (I know the role is usually $100,000) $200,000 Recruiter: How much are you compensated in your current role? Candidate: $90,000 Recruiter: We’d be excited to offer you $95,000 for your experiences for the role.

So Why Do They Even Ask?

Recruiters ask for a number to negotiate a lower one. Asking yourself limits you.

You'll rarely get more than you asked for, and your request can be lowered.

The takeaway from all of this is to never give an expected compensation.

Tell them you haven't thought about it when you applied.

Every week I meet many people interested in VC. Many of them ask me what it's like to be a junior analyst in VC or what I've learned so far.

Looking back, I've learned many things as a junior VC, having gone through an almost-euphoric peak bull market, failed tech IPOs of 2019 including WeWorks' catastrophic fall, and the beginnings of a bearish market.

1. Network, network, network!

VCs spend 80% of their time networking. Junior VCs source deals or manage portfolios. You spend your time bringing startups to your fund or helping existing portfolio companies grow. Knowing stakeholders (corporations, star talent, investors) in your particular areas of investment helps you develop your portfolio.

Networking was one of my strengths. When I first started in the industry, I'd go to startup events and meet 50 people a month. Over time, I realized these relationships were shallow and I was only getting business cards. So I stopped seeing networking as a transaction. VC is a long-term game, so you should work with people you like. Now I know who I click with and can build deeper relationships with them. My network is smaller but more valuable than before.

2. The Most Important Metric Is Founder

People often ask how we pick investments. Why some companies can raise money and others can't is a mystery. The founder is the most important metric for VCs. When a company is young, the product, environment, and team all change, but the founder remains constant. VCs bet on the founder, not the company.

How do we decide which founders are best after 2-3 calls? When looking at a founder's profile, ask why this person can solve this problem. The founders' track record will tell. If the founder is a serial entrepreneur, you know he/she possesses the entrepreneur DNA and will likely succeed again. If it's his/her first startup, focus on industry knowledge to deliver the best solution.

3. A company's fate can be determined by macrotrends.

Macro trends are crucial. A company can have the perfect product, founder, and team, but if it's solving the wrong problem, it won't succeed. I've also seen average companies ride the wave to success. When you're on the right side of a trend, there's so much demand that more companies can get a piece of the pie.

In COVID-19, macro trends made or broke a company. Ed-tech and health-tech companies gained unicorn status and raised funding at inflated valuations due to sudden demand. With the easing of pandemic restrictions and the start of a bear market, many of these companies' valuations are in question.

4. Look for methods to ACTUALLY add value.

You only need to go on VC twitter (read: @vcstartterkit and @vcbrags) for 5 minutes or look at fin-meme accounts on Instagram to see how much VCs claim to add value but how little they actually do. VC is a long-term game, though. Long-term, founders won't work with you if you don't add value.

How can we add value when we're young and have no network? Leaning on my strengths helped me. Instead of viewing my age and limited experience as a disadvantage, I realized that I brought a unique perspective to the table.

As a VC, you invest in companies that will be big in 5-7 years, and millennials and Gen Z will have the most purchasing power. Because you can relate to that market, you can offer insights that most Partners at 40 can't. I added value by helping with hiring because I had direct access to university talent pools and by finding university students for product beta testing.

5. Develop your personal brand.

Generalists or specialists run most funds. This means that funds either invest across industries or have a specific mandate. Most funds are becoming specialists, I've noticed. Top-tier founders don't lack capital, so funds must find other ways to attract them. Why would a founder work with a generalist fund when a specialist can offer better industry connections and partnership opportunities?

Same for fund members. Founders want quality investors. Become a thought leader in your industry to meet founders. Create content and share your thoughts on industry-related social media. When I first started building my brand, I found it helpful to interview industry veterans to create better content than I could on my own. Over time, my content attracted quality founders so I didn't have to look for them.

These are my biggest VC lessons. This list isn't exhaustive, but it's my industry survival guide.

SpaceX's Starship.

Launched last week.

Four minutes in:

SpaceX will succeed. When it does, its massiveness will matter.

Its payload will revolutionize space economics.

Civilization will shift.

We don't yet understand how this will affect space and Earth culture. Grab it.

The Cost of Space Transportation Has Decreased Exponentially

Space launches have increased dramatically in recent years.

We mostly send items to LEO, the green area below:

SpaceX's reusable rockets can send these things to LEO. Each may launch dozens of payloads into space.

With all these launches, we're sending more than simply things to space. Volume and mass. Since the 1980s, launching a kilogram of payload to LEO has become cheaper:

One kilogram in a large rocket cost over $75,000 in the 1980s. Carrying one astronaut cost nearly $5M! Falcon Heavy's $1,500/kg price is 50 times lower. SpaceX's larger, reusable rockets are amazing.

SpaceX's Starship rocket will continue. It can carry over 100 tons to LEO, 50% more than the current Falcon heavy. Thousands of launches per year. Elon Musk predicts Falcon Heavy's $1,500/kg cost will plummet to $100 in 23 years.

In context:

People underestimate this.

2. The Benefits of Affordable Transportation

Compare Earth's transportation costs:

It's no surprise that the US and Northern Europe are the wealthiest and have the most navigable interior waterways.

So what? since sea transportation is cheaper than land. Inland waterways are even better than sea transportation since weather is less of an issue, currents can be controlled, and rivers serve two banks instead of one for coastal transportation.

In France, because population density follows river systems, rivers are valuable. Cheap transportation brought people and money to rivers, especially their confluences.

How come? Why were humans surrounding rivers?

Imagine selling meat for $10 per kilogram. Transporting one kg one kilometer costs $1. Your margin decreases $1 each kilometer. You can only ship 10 kilometers. For example, you can only trade with four cities:

If instead, your cost of transportation is half, what happens? It costs you $0.5 per km. You now have higher margins with each city you traded with. More importantly, you can reach 20-km markets.

However, 2x distance 4x surface! You can now trade with sixteen cities instead of four! Metcalfe's law states that a network's value increases with its nodes squared. Since now sixteen cities can connect to yours. Each city now has sixteen connections! They get affluent and can afford more meat.

Rivers lower travel costs, connecting many cities, which can trade more, get wealthy, and buy more.

The right network is worth at least an order of magnitude more than the left! The cheaper the transport, the more trade at a lower cost, the more income generated, the more that wealth can be reinvested in better canals, bridges, and roads, and the wealth grows even more.

Throughout history. Rome was established around cheap Mediterranean transit and preoccupied with cutting overland transportation costs with their famous roadways. Communications restricted their empire.

The Egyptians lived around the Nile, the Vikings around the North Sea, early Japan around the Seto Inland Sea, and China started canals in the 5th century BC.

Transportation costs shaped empires.Starship is lowering new-world transit expenses. What's possible?

3. Change Organizations, Change Companies, Change the World

Starship is a conveyor belt to LEO. A new world of opportunity opens up as transportation prices drop 100x in a decade.

Satellite engineers have spent decades shedding milligrams. Weight influenced every decision: pricing structure, volumes to be sent, material selections, power sources, thermal protection, guiding, navigation, and control software. Weight was everything in the mission. To pack as much science into every millimeter, NASA missions had to be miniaturized. Engineers were indoctrinated against mass.

No way.

Starship is not constrained by any space mission, robotic or crewed.

Starship obliterates the mass constraint and every last vestige of cultural baggage it has gouged into the minds of spacecraft designers. A dollar spent on mass optimization no longer buys a dollar saved on launch cost. It buys nothing. It is time to raise the scope of our ambition and think much bigger. — Casey Handmer, Starship is still not understood

A Tesla Roadster in space makes more sense.

It went beyond bad PR. It told the industry: Did you care about every microgram? No more. My rockets are big enough to send a Tesla without noticing. Industry watchers should have noticed.

Most didn’t. Artemis is a global mission to send astronauts to the Moon and build a base. Artemis uses disposable Space Launch System rockets. Instead of sending two or three dinky 10-ton crew habitats over the next decade, Starship might deliver 100x as much cargo and create a base for 1,000 astronauts in a year or two. Why not? Because Artemis remains in a pre-Starship paradigm where each kilogram costs a million dollars and we must aggressively descope our objective.

Space agencies can deliver 100x more payload to space for the same budget with 100x lower costs and 100x higher transportation volumes. How can space economy saturate this new supply?

Before Starship, NASA supplied heavy equipment for Moon base construction. After Starship, Caterpillar and Deere may space-qualify their products with little alterations. Instead than waiting decades for NASA engineers to catch up, we could send people to build a space outpost with John Deere equipment in a few years.

History is littered with the wreckage of former industrial titans that underestimated the impact of new technology and overestimated their ability to adapt: Blockbuster, Motorola, Kodak, Nokia, RIM, Xerox, Yahoo, IBM, Atari, Sears, Hitachi, Polaroid, Toshiba, HP, Palm, Sony, PanAm, Sega, Netscape, Compaq, GM… — Casey Handmer, Starship is still not understood

Everyone saw it coming, but senior management failed to realize that adaption would involve moving beyond their established business practice. Others will if they don't.

4. The Starship Possibilities

It's Starlink.

SpaceX invented affordable cargo space and grasped its implications first. How can we use all this inexpensive cargo nobody knows how to use?

Satellite communications seemed like the best way to capitalize on it. They tried. Starlink, designed by SpaceX, provides fast, dependable Internet worldwide. Beaming information down is often cheaper than cable. Already profitable.

Starlink is one use for all this cheap cargo space. Many more. The longer firms ignore the opportunity, the more SpaceX will acquire.

What are these chances?

Satellite imagery is outdated and lacks detail. We can improve greatly. Synthetic aperture radar can take beautiful shots like this:

Have you ever used Google Maps and thought, "I want to see this in more detail"? What if I could view Earth live? What if we could livestream an infrared image of Earth?

We could launch hundreds of satellites with such mind-blowing visual precision of the Earth that we would dramatically improve the accuracy of our meteorological models; our agriculture; where crime is happening; where poachers are operating in the savannah; climate change; and who is moving military personnel where. Is that useful?

What if we could see Earth in real time? That affects businesses? That changes society?

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