Apple's latest revelation may shock iPod fans and former owners.

Apple discontinued the iPod touch on May 11, 2022. After 21 years, Apple killed the last surviving iPod, a device Steve Jobs believed would revolutionize the music industry.

Jobs was used to making bold predictions, but few expected Apple's digital music player to change the music industry. It did.

This chaos created new business opportunities. Spotify, YouTube, and Amazon are products of that chaotic era.

As the digital landscape changes, so do consumers, and the iPod has lost favor. I'm sure Apple realizes the importance of removing an icon. The iPod was Apple like the Mac and iPhone. I think it's bold to retire such a key Apple cornerstone. What would Jobs do?

iPod evolution across the ages

Here's an iPod family tree for all you enthusiasts.

iPod vintage (Oct 2001 to Sep 2014, 6 generations)

The original iPod had six significant upgrades since 2001. Apple announced an 80 GB ($249) and 160 GB ($349) iPod classic in 2007.

Apple updated the 80 GB model with a 120 GB device in September 2008. Apple upgraded the 120 GB model with a 160 GB variant a year later (2009). This was the last iteration, and Apple discontinued the classic in September 2014.

iPod nano (Jan 2004 to Sep 2005, 2 generations)

Apple debuted a smaller, brightly-colored iPod in 2004. The first model featured 4 GB, enough for 1,000 songs.

Apple produced a new 4 GB or 6 GB iPod mini in February 2005 and discontinued it in September when they released a better-looking iPod nano.

iTouch nano (Sep 2005 to July 2017, 7 generations)

I loved the iPod nano. It was tiny and elegant with enough tech to please most music aficionados, unless you carry around your complete music collection.

Apple owed much of the iPod nano's small form and success to solid-state flash memory. Flash memory doesn't need power because it has no moving parts. This makes the iPod nano more durable than the iPod classic and mini, which employ hard drives.

Apple manufactured seven generations of the iPod nano, improving its design, display screen, memory, battery, and software, but abandoned it in July 2017 due to dwindling demand.

Shuffle iPod (Jan 2005 to Jul 2017, 4 generations)

The iPod shuffle was entry-level. It was a simple, lightweight, tiny music player. The iPod shuffle was perfect for lengthy bike trips, runs, and hikes.

Apple sold 10 million iPod shuffles in the first year and kept making them for 12 years, through four significant modifications.

iOS device (Sep 2007 to May 2022, 7 generations)

The iPod touch's bigger touchscreen interface made it a curious addition to the iPod family. The iPod touch resembled an iPhone more than the other iPods, making them hard to tell apart.

Many were dissatisfied that Apple removed functionality from the iPod touch to avoid making it too similar to the iPhone. Seven design improvements over 15 years brought the iPod touch closer to the iPhone, but not completely.

The iPod touch uses the same iOS operating system as the iPhone, giving it access to many apps, including handheld games.

The iPod touch's long production run is due to the next generation of music-loving gamers.

What made the iPod cool

iPod revolutionized music listening. It was the first device to store and play MP3 music, allowing you to carry over 1,000 songs anywhere.

The iPod changed consumer electronics with its scroll wheel and touchscreen. Jobs valued form and function equally. He showed people that a product must look good to inspire an emotional response and ignite passion.

The elegant, tiny iPod was a tremendous sensation when it arrived for $399 in October 2001. Even at this price, it became a must-have for teens to CEOs.

It's hard to identify any technology that changed how music was downloaded and played like the iPod. Apple iPod and iTunes had 63% of the paid music download market in the fourth quarter of 2012.

The demise of the iPod was inevitable

Apple discontinuing the iPod touch after 21 years is sad. This ends a 00s music icon.

Jobs was a genius at anticipating market needs and opportunities, and Apple launched the iPod at the correct time.

Few consumer electronics items have had such a lasting impact on music lovers and the music industry as the iPod.

Smartphones and social media have contributed to the iPod's decline. Instead of moving to the music, the new generation of consumers is focused on social media. They're no longer passive content consumers; they're active content creators seeking likes and followers. Here, the smartphone has replaced the iPod.

It's hard not to feel a feeling of loss, another part of my adolescence now forgotten by the following generation.

So, if you’re lucky enough to have a working iPod, hang on to that relic and enjoy the music and the nostalgia.

Here is the ugly stuff, read this if you have a founder in your life or are trying to become one. Your call.

#1 You'll try to talk yourself to sleep, but it won't always work.

As founders, we're all driven. Good and bad, you're restless. Success requires resistance and discipline. Your startup will be on your mind 24/7, and not everyone will have the patience to listen to your worries, ideas, and coffee runs. You become more self-sufficient than ever before.

#2 No one will understand what you're going through unless they've been a founder.

Some of my closest friends don't understand the work that goes into starting a business, and we can't blame them.

#3 You'll feel alienated.

Your problems aren't common; calling your bestie won't help. You must search hard for the right resources. It alienates you from conversations you no longer relate to. (No 4th of July, no long weekends!)

#4 Since you're your "own boss," people assume you have lots of free time.

Do you agree? I was on a webinar with lots of new entrepreneurs, and one woman said, "I started my own business so I could have more time for myself." This may be true for some lucky people, and you can be flexible with your schedule. If you want your business to succeed, you'll probably be its slave for a while.

#5 No time for illness or family emergencies.

Both last month. Oh, no! Physically and emotionally withdrawing at the worst times will give you perspective. I learned this the hard way because I was too stubborn to postpone an important interview. I thought if I rested all day and only took one call, I'd be fine. Nope. I had a fever and my mind wasn't as sharp, so my performance and audience interaction suffered. Nope. Better to delay than miss out.

Oh, and setting a "OoO" makes you cringe.

#6 Good luck with your mental health, perfectionists.

When building a startup, it's difficult to accept that there won't be enough time to do everything. You can't make them all, not perfectly. You must learn to accept things that are done but not perfect.

#7 As a founder, you'll make mistakes, but you'll want to make them quickly so you can learn.

Hard lessons are learned quicker. You'll need to pivot and try new things often; some won't work, and it's best to discover them sooner rather than later.

#8 Pyramid schemes abound.

I didn't realize how bad it was until I started a company. You must spy and constantly research. As a founder, you'll receive many emails from people claiming to "support" you. Be wary and keep your eyes open. When it's too good to be true. Some "companies" will try to get you to pay for "competitions" to "pitch at events." Don't do it.

#9 Keep your competitor research to a minimum.

Actually, competition is good. It means there's a market for those solutions. However, this can be mentally exhausting too. Learn about their geography and updates, but that's it.

#10 You'll feel guilty taking vacation.

I don't know what to say, but I no longer enjoy watching TV, and that's okay. Pay attention to things that enrich you, bring you joy, and have fun. It boosts creativity.

Being a startup founder may be one of the hardest professional challenges you face, but it's also a great learning experience. Your passion will take you places you never imagined and open doors to opportunities you wouldn't have otherwise. You'll meet amazing people. No regrets, no complaints. It's a roller coaster, but the good days are great.

Miss anything? Comment below

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.

5 VC investment criteria

I reviewed 200 startup business concepts last week. Brainache.

The enterprises sold various goods and services. The concepts were achingly similar: give us money, we'll produce a product, then get more to expand. No different from daily plans and pitches.

Most of those 200 plans sounded plausible. But 10% looked venture-worthy. 90% of startups need alternatives to venture finance.

With the success of VC-backed businesses and the growth of venture funds, a common misperception is that investors would fund any decent company idea. Finding investors that believe in the firm and founders is the key to funding.

Incorrect. Venture capital needs investing in certain enterprises. If your startup doesn't match the model, as most early-stage startups don't, you can revise your business plan or locate another source of capital.

Before spending six months pitching angels and VCs, make sure your startup fits these criteria.

Likely to generate $100 million in sales

First, I check the income predictions in a pitch deck. If it doesn't display $100M, don't bother.

The math doesn't work for venture financing in smaller businesses.

Say a fund invests $1 million in a startup valued at $5 million that is later acquired for $20 million. That's a win everyone should celebrate. Most VCs don't care.

Consider a $100M fund. The fund must reach $360M in 7 years with a 20% return. Only 20-30 investments are possible. 90% of the investments will fail, hence the 23 winners must return $100M-$200M apiece. $15M isn't worth the work.

Angel investors and tiny funds use the same ideas as venture funds, but their smaller scale affects the calculations. If a company can support its growth through exit on less than $2M in angel financing, it must have $25M in revenues before large companies will consider acquiring it.

Aiming for Hypergrowth

A startup's size isn't enough. It must expand fast.

Developing a great business takes time. Complex technology must be constructed and tested, a nationwide expansion must be built, or production procedures must go from lab to pilot to factories. These can be enormous, world-changing corporations, but venture investment is difficult.

The normal 10-year venture fund life. Investments are made during first 3–4 years.. 610 years pass between investment and fund dissolution. Funds need their investments to exit within 5 years, 7 at the most, therefore add a safety margin.

Longer exit times reduce ROI. A 2-fold return in a year is excellent. Loss at 2x in 7 years.

Lastly, VCs must prove success to raise their next capital. The 2nd fund is raised from 1st fund portfolio increases. Third fund is raised using 1st fund's cash return. Fund managers must raise new money quickly to keep their jobs.

Branding or technology that is protected

No big firm will buy a startup at a high price if they can produce a competing product for less. Their development teams, consumer base, and sales and marketing channels are large. Who needs you?

Patents, specialist knowledge, or brand name are the only answers. The acquirer buys this, not the thing.

I've heard of several promising startups. It's not a decent investment if there's no exit strategy.

A company that installs EV charging stations in apartments and shopping areas is an example. It's profitable, repeatable, and big. A terrific company. Not a startup.

This building company's operations aren't secret. No technology to protect, no special information competitors can't figure out, no go-to brand name. Despite the immense possibilities, a large construction company would be better off starting their own.

Most venture businesses build products, not services. Services can be profitable but hard to safeguard.

Probable purchase at high multiple

Once a software business proves its value, acquiring it is easy. Pharma and medtech firms have given up on their own research and instead acquire startups after regulatory permission. Many startups, especially in specialized areas, have this weakness.

That doesn't mean any lucrative $25M-plus business won't be acquired. In many businesses, the venture model requires a high exit premium.

A startup invents a new glue. 3M, BASF, Henkel, and others may buy them. Adding more adhesive to their catalogs won't boost commerce. They won't compete to buy the business. They'll only buy a startup at a profitable price. The acquisition price represents a moderate EBITDA multiple.

The company's $100M revenue presumably yields $10m in profits (assuming they’ve reached profitability at all). A $30M-$50M transaction is likely. Not terrible, but not what venture investors want after investing $25M to create a plant and develop the business.

Private equity buys profitable companies for a moderate profit multiple. It's a good exit for entrepreneurs, but not for investors seeking 10x or more what PE firms pay. If a startup offers private equity as an exit, the conversation is over.

Constructed for purchase

The startup wants a high-multiple exit. Unless the company targets $1B in revenue and does an IPO, exit means acquisition.

If they're constructing the business for acquisition or themselves, founders must decide.

If you want an indefinitely-running business, I applaud you. We need more long-term founders. Most successful organizations are founded around consumer demands, not venture capital's urge to grow fast and exit. Not venture funding.

if you don't match the venture model, what to do

VC funds moonshots. The 10% that succeed are extraordinary. Not every firm is a rocketship, and launching the wrong startup into space, even with money, will explode.

But just because your startup won't make $100M in 5 years doesn't mean it's a bad business. Most successful companies don't follow this model. It's not venture capital-friendly.

Although venture capital gets the most attention due to a few spectacular triumphs (and disasters), it's not the only or even most typical option to fund a firm.

Other ways to support your startup:

• Personal and family resources, such as credit cards, second mortgages, and lines of credit

• bootstrapping off of sales

• government funding and honors

• Private equity & project financing

• collaborating with a big business

• Including a business partner

Before pitching angels and VCs, be sure your startup qualifies. If so, include them in your pitch.