A top-down company plan facilitates decision-making and impresses investors.

A startup business plan starts with the product, the target customers, how to reach them, and how to grow the business.

Bottom-up is terrific unless venture investors fund it.

If it can prove how it can exceed $100M in sales, investors will invest. If not, the business may be wonderful, but it's not venture capital-investable.

As a rule, venture investors only fund firms that expect to reach $100M within 5 years.

Investors get nothing until an acquisition or IPO. To make up for 90% of failed investments and still generate 20% annual returns, portfolio successes must exit with a 25x return. A $20M-valued company must be acquired for $500M or more.

This requires $100M in sales (or being on a nearly vertical trajectory to get there). The company has 5 years to attain that milestone and create the requisite ROI.

This motivates venture investors (venture funds and angel investors) to hunt for $100M firms within 5 years. When you pitch investors, you outline how you'll achieve that aim.

I'm wary of pitches after seeing a million hockey sticks predicting $5M to $100M in year 5 that never materialized. Doubtful.

Startups fail because they don't have enough clients, not because they don't produce a great product. That jump from $5M to $100M never happens. The company reaches $5M or $10M, growing at 10% or 20% per year.  That's great, but not enough for a $500 million deal.

Once it becomes clear the company won’t reach orbit, investors write it off as a loss. When a corporation runs out of money, it's shut down or sold in a fire sale. The company can survive if expenses are trimmed to match revenues, but investors lose everything.

When I hear a pitch, I'm not looking for bright income projections but a viable plan to achieve them. Answer these questions in your pitch.

• Is the market size sufficient to generate $100 million in revenue?

• Will the initial beachhead market serve as a springboard to the larger market or as quicksand that hinders progress?

• What marketing plan will bring in $100 million in revenue? Is the market diffuse and will cost millions of dollars in advertising, or is it one, focused market that can be tackled with a team of salespeople?

• Will the business be able to bridge the gap from a small but fervent set of early adopters to a larger user base and avoid lock-in with their current solution?

• Will the team be able to manage a $100 million company with hundreds of people, or will hypergrowth force the organization to collapse into chaos?

• Once the company starts stealing market share from the industry giants, how will it deter copycats?

The requirement to reach $100M may be onerous, but it provides a context for difficult decisions: What should the product be? Where should we concentrate? who should we hire? Every strategic choice must consider how to reach $100M in 5 years.

Focusing on $100M streamlines investor pitches. Instead of explaining everything, focus on how you'll attain $100M.

As an investor, I know I'll lose my money if the startup doesn't reach this milestone, so the revenue prediction is the first thing I look at in a pitch deck.

Reaching the $100M goal needs to be the first thing the entrepreneur thinks about when putting together the business plan, the central story of the pitch, and the criteria for every important decision the company makes.

There’s a funny part of ‘Steve Jobs’ by Walter Isaacson where Jobs says that Bill Gates was more a copier than an innovator:

“Bill is basically unimaginative and has never invented anything, which is why I think he’s more comfortable now in philanthropy than technology. He just shamelessly ripped off other people’s ideas….He’d be a broader guy if he had dropped acid once or gone off to an ashram when he was younger.”

Gates lacked flavor. Nobody ever got excited about a Microsoft launch, despite their good products. Jobs had the world's best product taste. Apple vs. Microsoft.

A CEO's core job functions are all driven by taste: recruiting, vision, and company culture all require good taste. Depending on the type of company you want to build, know where you stand between Microsoft and Apple.

How can you improve your product judgment? How to acquire taste?

Test and refine

Product development follows two parallel paths: the ‘customer obsession’ path and the ‘taste and iterate’ path.

The customer obsession path involves solving customer problems. Lean Startup frameworks show you what to build at each step.

Taste-and-iterate doesn't involve the customer. You iterate internally and rely on product leaders' taste and judgment.

Creative Selection by Ken Kocienda explains this method. In Creative Selection, demos are iterated and presented to product leaders. Your boss presents to their boss, and so on up to Steve Jobs. If you have good product taste, you can be a panelist.

The iPhone follows this path. Before seeing an iPhone, consumers couldn't want one. Customer obsession wouldn't have gotten you far because iPhone buyers didn't know they wanted one.

In The Hard Thing About Hard Things, Ben Horowitz writes:

“It turns out that is exactly what product strategy is all about — figuring out the right product is the innovator’s job, not the customer’s job. The customer only knows what she thinks she wants based on her experience with the current product. The innovator can take into account everything that’s possible, but often must go against what she knows to be true. As a result, innovation requires a combination of knowledge, skill, and courage.“

One path solves a problem the customer knows they have, and the other doesn't. Instead of asking a person what they want, observe them and give them something they didn't know they needed.

It's much harder. Apple is the world's most valuable company because it's more valuable. It changes industries permanently.

If you want to build superior products, use the iPhone of your industry.

How to Improve Your Taste

I. Work for a company that has taste.

People with the best taste in products, markets, and people are rewarded for building great companies. Tasteful people know quality even when they can't describe it. Taste isn't writable. It's feel-based.

Moving into a community that's already doing what you want to do may be the best way to develop entrepreneurial taste. Most company-building knowledge is tacit.

Joining a company you want to emulate allows you to learn its inner workings. It reveals internal patterns intuitively. Many successful founders come from successful companies.

Consumption determines taste. Excellence will refine you. This is why restauranteurs visit the world's best restaurants and serious painters visit Paris or New York. Joining a company with good taste is beneficial.

2. Possess a wide range of interests

“Edwin Land of Polaroid talked about the intersection of the humanities and science. I like that intersection. There’s something magical about that place… The reason Apple resonates with people is that there’s a deep current of humanity in our innovation. I think great artists and great engineers are similar, in that they both have a desire to express themselves.” — Steve Jobs

I recently discovered Edwin Land. Jobs modeled much of his career after Land's. It makes sense that Apple was inspired by Land.

A Triumph of Genius: Edwin Land, Polaroid, and the Kodak Patent War notes:

“Land was introverted in person, but supremely confident when he came to his ideas… Alongside his scientific passions, lay knowledge of art, music, and literature. He was a cultured person growing even more so as he got older, and his interests filtered into the ethos of Polaroid.”

Founders' philosophies shape companies. Jobs and Land were invested. It showed in the products their companies made. Different. His obsession was spreading Microsoft software worldwide. Microsoft's success is why their products are bland and boring.

Experience is important. It's probably why startups are built by generalists and scaled by specialists.

Jobs combined design, typography, storytelling, and product taste at Apple. Some of the best original Mac developers were poets and musicians. Edwin Land liked broad-minded people, according to his biography. Physicist-musicians or physicist-photographers.

Da Vinci was a master of art, engineering, architecture, anatomy, and more. He wrote and drew at the same desk. His genius is remembered centuries after his death. Da Vinci's statue would stand at the intersection of humanities and science.

We find incredibly creative people here. Superhumans. Designers, creators, and world-improvers. These are the people we need to navigate technology and lead world-changing companies. Generalists lead.

My ego is so huge it won't fit through the door.

I don't know how I feel about it. I should be excited. Many of you have this exact dream to publish a book with a well-known book publisher and get a juicy advance.

Let me dissect how I'm thinking about it to help you.

How it happened

An email comes in. A generic "can we put a backlink on your website and get a freebie" email.

Almost deleted it.

Then I noticed the logo. It seemed shady. I found the URL. Check. I searched the employee's LinkedIn. Legit. I avoided middlemen. Check.

Mixed feelings. LinkedIn hasn't valued my writing for years. I'm just a guy in an unironed t-shirt whose content they sell advertising against.

They get big dollars. I get $0 and a few likes, plus some email subscribers.

Still, I felt adrenaline for hours.

I texted a few friends to see how they felt. I wrapped them.

Messages like "No shocker. You're entertaining online." I didn't like praises, so I blushed.

The thrill faded after hours. Who knows?

Most authors desire this chance.

"You entitled piece of crap, Denning!"

You may think so. Okay. My job is to stand on the internet and get bananas thrown at me.

I approached writing backwards. More important than a book deal was a social media audience converted to an email list.

Romantic authors think backward. They hope a fantastic book will land them a deal and an audience.

Rarely occurs. So I never pursued it. It's like permission-seeking or the lottery.

Not being a professional writer, I've never written a good book. I post online for fun and to express my opinions.

Writing is therapeutic. I overcome mental illness and rebuilt my life this way. Without blogging, I'd be dead.

I've always dreamed of staying alive and doing something I love, not getting a book contract. Writing is my passion. I'm a winner without a book deal.

Why I was given a book deal

You may assume I received a book contract because of my views or follows. Nope.

They gave me a deal because they like my writing style. I've heard this for eight years.

Several authors agree. One asked me to improve their writer's voice.

Takeaway: highlight your writer's voice.

What if they discover I'm writing incompetently?

An edited book is published. It's edited.

I need to master writing mechanics, thus this concerns me. I need help with commas and sentence construction.

I must learn verb, noun, and adjective. Seriously.

Writing a book may reveal my imposter status to a famous publisher. Imagine the email

"It happened again. He doesn't even know how to spell. He thinks 'less' is the correct word, not 'fewer.' Are you sure we should publish his book?"

Fears stink.

I'm capable of blogging. Even listicles. So what?

Writing for a major publisher feels advanced.

I only blog. I'm good at listicles. Digital media executives have criticized me for this.

• It is allegedly clickbait.

• Or it is following trends.

• Alternately, growth hacking.

Never. I learned copywriting to improve my writing.

Apple, Amazon, and Tesla utilize copywriting to woo customers. Whoever thinks otherwise is the wisest person in the room.

Old-schoolers loathe copywriters.

Their novels sell nothing.

They assume their elitist version of writing is better and that the TikTok generation will invest time in random writing with no subheadings and massive walls of text they can't read on their phones.

I'm terrified of book proposals.

My friend's book proposal suggestion was contradictory and made no sense.

They told him to compose another genre. This book got three Amazon reviews. Is that a good model?

The process disappointed him. I've heard other book proposal horror stories. Tim Ferriss' book "The 4-Hour Workweek" was criticized.

Because he has thick skin, his book came out. He wouldn't be known without that.

I hate book proposals.

An ongoing commitment

Writing a book is time-consuming.

I appreciate time most. I want to focus on my daughter for the next few years. I can't recreate her childhood because of a book.

No idea how parents balance kids' goals.

My silly face in a bookstore. Really?

Genuine thought.

I don't want my face in bookstores. I fear fame. I prefer anonymity.

I want to purchase a property in a bad Australian area, then piss off and play drums. Is bookselling worth it?

Are there even bookstores anymore?

(Except for Ryan Holiday's legendary Painted Porch Bookshop in Texas.)

What's most important about books

Many were duped.

Tweets and TikTok hopscotch vids are their future. Short-form content creates devoted audiences that buy newsletter subscriptions.

Books=depth.

Depth wins (if you can get people to buy your book). Creating a book will strengthen my reader relationships.

It's cheaper than my classes, so more people can benefit from my life lessons.

A deeper justification for writing a book

Mind wandered.

If I write this book, my daughter will follow it. "Look what you can do, love, when you ignore critics."

That's my favorite.

I'll be her best leader and teacher. If her dad can accomplish this, she can too.

My kid can read my book when I'm gone to remember her loving father.

Last paragraph made me cry.

The positive

This book thing might make me sound like Karen.

The upside is... Building in public, like I have with online writing, attracts the right people.

Proof-of-work over proposals, beautiful words, or huge aspirations. If you want a book deal, try writing online instead of the old manner.

Next steps

No idea.

I'm a rural Aussie. Writing a book in the big city is intimidating. Will I do it? Lots to think about. Right now, some level of reflection and gratitude feels most appropriate.

Sometimes when you don't feel worthy, it gives you the greatest lessons. That's how I feel about getting offered this book deal.

Perhaps you can relate.

ZERO GRACE/ZERO MALICE

Big companies and wealthy people make stupid mistakes too.

Your ancestors kept snakes and drank bad water. You (probably) don't because you've learnt from their failures via instinct+, the ultimate life-lessons streaming network in your head. Instincts foretell the future. If you approach a lion, it'll eat you. Our society's nuanced/complex decisions have surpassed instinct. Human growth depends on how we handle these issues. 80% of people believe they are above-average drivers, yet few believe they make many incorrect mistakes that make them risky. Stupidity hurts others like death. Basic Laws of Human Stupidity by Carlo Cipollas:

1. Everyone underestimates the prevalence of idiots in our society.

2. Any other trait a person may have has no bearing on how likely they are to be stupid.

3. A dumb individual is one who harms someone without benefiting themselves and may even lose money in the process.

4. Non-dumb people frequently underestimate how destructively powerful stupid people can be.

5. The most dangerous kind of person is a moron.

Professor Cippola defines stupid as bad for you and others. We underestimate the corporate world's and seemingly successful people's ability to make bad judgments that harm themselves and others. Success is an intoxication that makes you risk-aggressive and blurs your peripheral vision.

Stupid companies and decisions:

Big Dumber

Big-company bad ideas have more bulk and inertia. The world's most valuable company recently showed its board a VR headset. Jony Ive couldn't destroy Apple's terrible idea in 2015. Mr. Ive said that VR cut users off from the outer world, made them seem outdated, and lacked practical uses. Ives' design team doubted users would wear headsets for lengthy periods.

VR has cost tens of billions of dollars over a decade to prove nobody wants it. The next great SaaS startup will likely come from Florence, not Redmond or San Jose.

Apple Watch and Airpods have made the Cupertino company the world's largest jewelry maker. 10.5% of Apple's income, or $38 billion, comes from wearables in 2021. (seven times the revenue of Tiffany & Co.). Jewelry makes you more appealing and useful. Airpods and Apple Watch do both.

Headsets make you less beautiful and useful and promote isolation, loneliness, and unhappiness among American teenagers. My sons pretend they can't hear or see me when on their phones. VR headsets lack charisma.

Coinbase disclosed a plan to generate division and tension within its workplace weeks after Apple was pitched $2,000 smokes. The crypto-trading platform is piloting a program that rates staff after every interaction. If a coworker says anything you don't like, you should tell them how to improve. Everyone gets a 110-point scorecard. Coworkers should evaluate a person's rating while deciding whether to listen to them. It's ridiculous.

Organizations leverage our superpower of cooperation. This encourages non-cooperation, period. Bridgewater's founder Ray Dalio designed the approach to promote extreme transparency. Dalio has 223 billion reasons his managerial style works. There's reason to suppose only a small group of people, largely traders, will endure a granular scorecard. Bridgewater has 20% first-year turnover. Employees cry in bathrooms, and sex scandals are settled by ignoring individuals with poor believability levels. Coinbase might take solace that the stock is 80% below its initial offering price.

Poor Stupid

Fools' ledgers are valuable. More valuable are lists of foolish rich individuals.

Robinhood built a $8 billion corporation on financial ignorance. The firm's median account value is $240, and its stock has dropped 75% since last summer. Investors, customers, and society lose. Stupid. Luna published a comparable list on the blockchain, grew to $41 billion in market cap, then plummeted.

A podcast presenter is recruiting dentists and small-business owners to invest in Elon Musk's Twitter takeover. Investors pay a 7% fee and 10% of the upside for the chance to buy Twitter at a 35% premium to the current price. The proposal legitimizes CNBC's Trade Like Chuck advertising (Chuck made $4,600 into $460,000 in two years). This is stupid because it adds to the Twitter deal's desperation. Mr. Musk made an impression when he urged his lawyers to develop a legal rip-cord (There are bots on the platform!) to abandon the share purchase arrangement (for less than they are being marketed by the podcaster). Rolls-Royce may pay for this list of the dumb affluent because it includes potential Cullinan buyers.

Worst company? Flowcarbon, founded by WeWork founder Adam Neumann, operates at the convergence of carbon and crypto to democratize access to offsets and safeguard the earth's natural carbon sinks. Can I get an ayahuasca Big Gulp?

Neumann raised $70 million with their yogababble drink. More than half of the consideration came from selling GNT. Goddess Nature Token. I hope the company gets an S-1. Or I'll start a decentralized AI Meta Renewable NFTs company. My Community Based Ebitda coin will fund the company. Possible.

Stupidity inside oneself

This weekend, I was in NYC with my boys. My 14-year-old disappeared. He's realized I'm not cool and is mad I let the charade continue. When out with his dad, he likes to stroll home alone and depart before me. Friends told me hell would return, but I was surprised by how fast the eye roll came.

Not so with my 11-year-old. We went to The Edge, a Hudson Yards observation platform where you can see the city from 100 storeys up for $38. This is hell's seventh ring. Leaning into your boys' interests is key to engaging them (dad tip). Neither loves Crossfit, WW2 history, or antitrust law.

We take selfies on the Thrilling Glass Floor he spots. Dad, there's a bar! Coke? I nod, he rushes to the bar, stops, runs back for money, and sprints back. Sitting on stone seats, drinking Atlanta Champagne, he turns at me and asks, Isn't this amazing? I'll never reach paradise.

Later that night, the lads are asleep and I've had two Zacapas and Cokes. I SMS some friends about my day and how I feel about sons/fatherhood/etc. How I did. They responded and approached. The next morning, I'm sober, have distance from my son, and feel ashamed by my texts. Less likely to impulsively share my emotions with others. Stupid again.

A friend told me of an incident she found particularly irritating: a retailer where she is a frequent client, with an account and loyalty card, asked for the item's receipt.

We all know that stores collect every bit of data they can on us, including our socio-demographic profile, address, shopping habits, and everything we've ever bought, so why would they need a fading receipt? Who knows? That their consumers try to pass off other goods? It's easy to verify past transactions to see when the item was purchased.

That's it. Why require receipts? Companies send us incentives, discounts, and other marketing, yet when we need something, we have to prove we're not cheating.

Why require us to preserve data and documents when our governments and governmental institutions already have them? Why do I need to carry documents like my driver's license if the authorities can check if I have one and what state it's in once I prove my identity?

We shouldn't be required to give someone data or documents they already have. The days of waiting up with our paperwork for a stern official to inform us something is missing are over.

How can retailers still ask if you have a receipt if we've made our slow, bureaucratic, and all-powerful government sensible? Then what? The shop may not accept your return (which has a two-year window, longer than most purchase tickets last) or they may just let you replace the item.

Isn't this an anachronism in the age of CRMs, customer files that know what we ate for breakfast, and loyalty programs? If government and bureaucracies have learnt to use its own files and make life easier for the consumer, why do retailers ask for a receipt?

They're adding friction to the system. They know we can obtain a refund, use our warranty, or get our money back. But if I ask for ludicrous criteria, like keeping the purchase receipt in your wallet (wallet? another anachronism, if I leave the house with only my smartphone! ), it will dissuade some individuals and tip the scales in their favor when it comes to limiting returns. Some manager will take credit for lowering returns and collect her annual bonus. Having the wrong metrics is common in management.

To slow things down, asking for a receipt is like asking us to perform a handstand and leap 20 times on one foot. You have my information, use it to send me everything, and know everything I've bought, yet when I need a two-way service, you refuse to utilize it and require that I keep it and prove it.

Refuse as customers. If retailers want our business, they should treat us well, not just when we spend money. If I come to return a product, claim its use or warranty, or be taught how to use it, I am the same person you treated wonderfully when I bought it. Remember that, and act accordingly.

A store should use my information for everything, not just what it wants. Keep my info, but don't sell me anything.