How did his money blind me?

Like most fledgling entrepreneurs, I wanted a mentor. I met as many nearby folks with "entrepreneur" in their LinkedIn biographies for coffee.

These meetings taught me a lot, and I'd suggest them to any new creator. Attention! Meeting with many experienced entrepreneurs means getting contradictory advice. One entrepreneur will tell you to do X, then the next one you talk to may tell you to do Y, which are sometimes opposites. You'll have to chose which suggestion to take after the chats.

I experienced this. Same afternoon, I had two coffee meetings with experienced entrepreneurs. The first meeting was with a billionaire entrepreneur who took his company public.

I met him in a swanky hotel lobby and ordered a drink I didn't pay for. As a fledgling entrepreneur, money was scarce.

During the meeting, I demoed the software I'd built, he liked it, and we spent the hour discussing what features would make it a success. By the end of the meeting, he requested I include a killer feature we both agreed would attract buyers. The feature was complex and would require some time. The billionaire I was sipping coffee with in a beautiful hotel lobby insisted people would love it, and that got me enthusiastic.

The second meeting was with a young entrepreneur who had recently raised a small amount of investment and looked as eager to pitch me as I was to pitch him. I forgot his name. I mostly recall meeting him in a filthy coffee shop in a bad section of town and buying his pricey cappuccino. Water for me.

After his pitch, I demoed my app. When I was done, he barely noticed. He questioned my customer acquisition plan. Who was my client? What did they offer? What was my plan? Etc. No decent answers.

After our meeting, he insisted I spend more time learning my market and selling. He ignored my questions about features. Don't worry about features, he said. Customers will request features. First, find them.

Putting your faith in results over relevance

Problems plagued my afternoon. I met with two entrepreneurs who gave me differing advice about how to proceed, and I had to decide which to pursue. I couldn't decide.

Ultimately, I followed the advice of the billionaire.

Obviously.

Who wouldn’t? That was the guy who clearly knew more.

A few months later, I constructed the feature the billionaire said people would line up for.

The new feature was unpopular. I couldn't even get the billionaire to answer an email showing him what I'd done. He disappeared.

Within a few months, I shut down the company, wasting all the time and effort I'd invested into constructing the killer feature the billionaire said I required.

Would follow the struggling entrepreneur's advice have saved my company? It would have saved me time in retrospect. Potential consumers would have told me they didn't want what I was producing, and I could have shut down the company sooner or built something they did want. Both outcomes would have been better.

Now I know, but not then. I favored achievement above relevance.

Success vs. relevance

The millionaire gave me advice on building a large, successful public firm. A successful public firm is different from a startup. Priorities change in the last phase of business building, which few entrepreneurs reach. He gave wonderful advice to founders trying to double their stock values in two years, but it wasn't beneficial for me.

The other failing entrepreneur had relevant, recent experience. He'd recently been in my shoes. We still had lots of problems. He may not have achieved huge success, but he had valuable advice on how to pass the closest hurdle.

The money blinded me at the moment. Not alone So much of company success is defined by money valuations, fundraising, exits, etc., so entrepreneurs easily fall into this trap. Money chatter obscures the value of knowledge.

Don't base startup advice on a person's income. Focus on what and when the person has learned. Relevance to you and your goals is more important than a person's accomplishments when considering advice.

Most don't understand the issue until it's too late.

My first startup was what entrepreneurs call the hardest. A two-sided marketplace.

Two-sided marketplaces are the hardest startups because founders must solve the chicken or the egg conundrum.

A two-sided marketplace needs suppliers and buyers. Without suppliers, buyers won't come. Without buyers, suppliers won't come. An empty marketplace and a founder striving to gain momentum result.

My first venture made me a struggling founder seeking to achieve traction for a two-sided marketplace. The company failed, and I vowed never to start another like it.

I didn’t. Unfortunately, my second venture was almost as hard. It failed like the second-hardest startup.

What kind of startup is the second-hardest?

The second-hardest startup, which is almost as hard to develop, is rarely discussed in the startup community. Because of this, I predict more founders fail each year trying to develop the second-toughest startup than the hardest.

Fairly, I have no proof. I see many startups, so I have enough of firsthand experience. From what I've seen, for every entrepreneur developing a two-sided marketplace, I'll meet at least 10 building this other challenging startup.

I'll describe a startup I just met with its two co-founders to explain the second hardest sort of startup and why it's so hard. They created a financial literacy software for parents of high schoolers.

The issue appears plausible. Children struggle with money. Parents must teach financial responsibility. Problems?

It's possible.

Buyers and users are different.

Buyer-user mismatch.

The financial literacy app I described above targets parents. The parent doesn't utilize the app. Child is end-user. That may not seem like much, but it makes customer and user acquisition and onboarding difficult for founders.

The difficulty of a buyer-user imbalance

The company developing a product faces a substantial operational burden when the buyer and end customer are different. Consider classic firms where the buyer is the end user to appreciate that responsibility.

Entrepreneurs selling directly to end users must educate them about the product's benefits and use. Each demands a lot of time, effort, and resources.

Imagine selling a financial literacy app where the buyer and user are different. To make the first sale, the entrepreneur must establish all the items I mentioned above. After selling, the entrepreneur must supply a fresh set of resources to teach, educate, or train end-users.

Thus, a startup with a buyer-user mismatch must market, sell, and train two organizations at once, requiring twice the work with the same resources.

The second hardest startup is hard for reasons other than the chicken-or-the-egg conundrum. It takes a lot of creativity and luck to solve the chicken-or-egg conundrum.

The buyer-user mismatch problem cannot be overcome by innovation or luck. Buyer-user mismatches must be solved by force. Simply said, when a product buyer is different from an end-user, founders have a lot more work. If they can't work extra, their companies fail.

Most productive people are habitual.

Early in the day, do important tasks.

In his best-selling book Eat That Frog, Brian Tracy advised starting the day with your hardest, most important activity.

Most individuals work best in the morning. Energy and willpower peak then.

Mornings are also ideal for memory, focus, and problem-solving.

Thus, the morning is ideal for your hardest chores.

It makes sense to do these things during your peak performance hours.

Additionally, your morning sets the tone for the day. According to Brian Tracy, the first hour of the workday steers the remainder.

After doing your most critical chores, you may feel accomplished, confident, and motivated for the remainder of the day, which boosts productivity.

Develop Your Essentialism

In Essentialism, Greg McKeown claims that trying to be everything to everyone leads to mediocrity and tiredness.

You'll either burn out, be spread too thin, or compromise your ideals.

Greg McKeown advises Essentialism:

Clarify what’s truly important in your life and eliminate the rest.

Eliminating non-essential duties, activities, and commitments frees up time and energy for what matters most.

According to Greg McKeown, Essentialists live by design, not default.

You'll be happier and more productive if you follow your essentials.

Follow these three steps to live more essentialist.

Prioritize Your Tasks First

What matters most clarifies what matters less. List your most significant aims and values.

The clearer your priorities, the more you can focus on them.

On Essentialism, McKeown wrote, The ultimate form of effectiveness is the ability to deliberately invest our time and energy in the few things that matter most.

#2: Set Your Priorities in Order

Prioritize your priorities, not simply know them.

“If you don’t prioritize your life, someone else will.” — Greg McKeown

Planning each day and allocating enough time for your priorities is the best method to become more purposeful.

#3: Practice saying "no"

If a request or demand conflicts with your aims or principles, you must learn to say no.

Saying no frees up space for our priorities.

Place Sleep Above All Else

Many believe they must forego sleep to be more productive. This is false.

A productive day starts with a good night's sleep.

Matthew Walker (Why We Sleep) says:

“Getting a good night’s sleep can improve cognitive performance, creativity, and overall productivity.”

Sleep helps us learn, remember, and repair.

Unfortunately, 35% of people don't receive the recommended 79 hours of sleep per night.

Sleep deprivation can cause:

• increased risk of diabetes, heart disease, stroke, and obesity

• Depression, stress, and anxiety risk are all on the rise.

• decrease in general contentment

• decline in cognitive function

To live an ideal, productive, and healthy life, you must prioritize sleep.

Follow these six sleep optimization strategies to obtain enough sleep:

• Establish a nightly ritual to relax and prepare for sleep.

• Avoid using screens an hour before bed because the blue light they emit disrupts the generation of melatonin, a necessary hormone for sleep.

• Maintain a regular sleep schedule to control your body's biological clock (and optimizes melatonin production)

• Create a peaceful, dark, and cool sleeping environment.

• Limit your intake of sweets and caffeine (especially in the hours leading up to bedtime)

• Regular exercise (but not right before you go to bed, because your body temperature will be too high)

Sleep is one of the best ways to boost productivity.

Sleep is crucial, says Matthew Walker. It's the key to good health and longevity.

Move people with tiny words.

Apple fanboy here.

• Macs are awesome.

• Their iPhones rock.

• $19 cloths are great.

• $999 stands are amazing.

I love Apple's microcopy even more.

It's like the marketing goddess bit into the Apple logo and blessed the world with microcopy.

I took on a 30-day micro-stalking mission.

Every time I caught myself wasting time on YouTube, I had to visit Apple’s website to learn the secrets of the marketing goddess herself.

We've learned. Golden apples are calling.

Cut the friction

Benefit-first, not commitment-first.

Brands lose customers through friction.

Most brands don't think like customers.

• Brands want sales.

• Brands want newsletter signups.

Here's their microcopy:

• “Buy it now.”

• “Sign up for our newsletter.”

Both are difficult. They ask for big commitments.

People are simple creatures. Want pleasure without commitment.

Apple nails this.

So, instead of highlighting the commitment, they highlight the benefit of the commitment.

Saving on the latest iPhone sounds easier than buying it. Everyone saves, but not everyone buys.

A subtle change in framing reduces friction.

Apple eliminates customer objections to reduce friction.

Less customer friction means simpler processes.

Apple's copy expertly reassures customers about shipping fees and not being home. Apple assures customers that returning faulty products is easy.

Apple knows that talking to a real person is the best way to reduce friction and improve their copy.

Always rhyme

Learn about fine rhyme.

Poets make things beautiful with rhyme.

Copywriters use rhyme to stand out.

Apple’s copywriters have mastered the art of corporate rhyme.

Two techniques are used.

1. Perfect rhyme

Here, rhymes are identical.

2. Imperfect rhyme

Here, rhyming sounds vary.

Apple prioritizes meaning over rhyme.

Apple never forces rhymes that don't fit.

It fits so well that the copy seems accidental.

Add alliteration

Alliteration always entertains.

Alliteration repeats initial sounds in nearby words.

Apple's copy uses alliteration like no other brand I've seen to create a rhyming effect or make the text more fun to read.

For example, in the sentence "Sam saw seven swans swimming," the initial "s" sound is repeated five times. This creates a pleasing rhythm.

Microcopy overuse is like pouring ketchup on a Michelin-star meal.

Alliteration creates a memorable phrase in copywriting. It's subtler than rhyme, and most people wouldn't notice; it simply resonates.

I love how Apple uses alliteration and contrast between "wonders" and "ease".

Assonance, or repeating vowels, isn't Apple's thing.

You ≠ Hero, Customer = Hero

Your brand shouldn't be the hero.

Because they'll be using your product or service, your customer should be the hero of your copywriting. With your help, they should feel like they can achieve their goals.

I love how Apple emphasizes what you can do with the machine in this microcopy.

It's divine how they position their tools as sidekicks to help below.

This one takes the cake:

Dialogue-style writing

Conversational copy engages.

Excellent copy Like sharing gum with a friend.

This helps build audience trust.

Apple does this by using natural connecting words like "so" and phrases like "But that's not all."

Snowclone-proof

The mother of all microcopy techniques.

A snowclone uses an existing phrase or sentence to create a new one. The new phrase or sentence uses the same structure but different words.

It’s usually a well know saying like:

To be or not to be.

This becomes a formula:

To _ or not to _.

Copywriters fill in the blanks with cause-related words. Example:

To click or not to click.

Apple turns "survival of the fittest" into "arrival of the fittest."

It's unexpected and surprises the reader.

So this was fun.

But my fun has just begun.

Microcopy is 21st-century poetry.

I came as an Apple fanboy.

I leave as an Apple fanatic.

Now I’m off to find an apple tree.

Cause you know how it goes.

(Apples, trees, etc.)

This post is a summary. Original post available here.