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.

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.

Writing for readers:

14 years of daily writing.

I post practically everything on social media. I authored hundreds of articles, thousands of tweets, and numerous volumes to almost no one.

Tens of thousands of readers regularly praise me.

I despised writing. I'm stuck now.

I've learned what readers like and what doesn't.

Here are some essential guidelines for writing with impact:

Readers won't understand your work if you can't.

Though obvious, this slipped me up. Share your truths.

Stories engage human brains.

Showing the journey of a person from worm to butterfly inspires the human spirit.

Overthinking hinders powerful writing.

The best ideas come from inner understanding in between thoughts.

Avoid writing to find it. Write.

Writing a masterpiece isn't motivating.

Write for five minutes to simplify. Step-by-step, entertaining, easy steps.

Good writing requires a willingness to make mistakes.

So write loads of garbage that you can edit into a good piece.

Courageous writing.

A courageous story will move readers. Personal experience is best.

Go where few dare.

Templates, outlines, and boundaries help.

Limitations enhance writing.

Excellent writing is straightforward and readable, removing all the unnecessary fat.

Use five words instead of nine.

Use ordinary words instead of uncommon ones.

Readers desire relatability.

Too much perfection will turn it off.

Write to solve an issue if you can't think of anything to write.

Instead, read to inspire. Best authors read.

Every tweet, thread, and novel must have a central idea.

What's its point?

This can make writing confusing.

️ Don't direct your reader.

Readers quit reading. Demonstrate, describe, and relate.

Even if no one responds, have fun. If you hate writing it, the reader will too.

Smarter work yields better results.

17-year-old me worked and studied 20 hours a day. During school breaks, I did coursework and ran a nonprofit at night. Long hours earned me national campaigns, A-list opportunities, and a great career. As I aged, my thoughts changed. Working harder isn't necessarily the key to success.

In some cases, doing less work might lead to better outcomes.

Consider a hard-working small business owner. He can't beat his corporate rivals by working hard. Time's limited. An entrepreneur can work 24 hours a day, 7 days a week, but a rival can invest more money, create a staff, and put in more man hours. Why have small startups done what larger companies couldn't? Facebook paid $1 billion for 13-person Instagram. Snapchat, a 30-person startup, rejected Facebook and Google bids. Luck and efficiency each contributed to their achievement.

The key to success is not working hard. It’s working smart.

Being busy and productive are different. Busy doesn't always equal productive. Productivity is less about time management and more about energy management. Life's work. It's using less energy to obtain more rewards. I cut my work week from 80 to 40 hours and got more done. I value simplicity.

Here are seven activities I gave up in order to be more productive.

1. Give up working extra hours and boost productivity instead.

When did the five-day, 40-hour work week start? Henry Ford, Ford Motor Company founder, experimented with his workers in 1926.

He decreased their daily hours from 10 to 8, and shortened the work week from 6 days to 5. As a result, he saw his workers’ productivity increase.

According to a 1980 Business Roundtable report, Scheduled Overtime Effect on Construction Projects, the more you work, the less effective and productive you become.

“Where a work schedule of 60 or more hours per week is continued longer than about two months, the cumulative effect of decreased productivity will cause a delay in the completion date beyond that which could have been realized with the same crew size on a 40-hour week.” Source: Calculating Loss of Productivity Due to Overtime Using Published Charts — Fact or Fiction

AlterNet editor Sara Robinson cited US military research showing that losing one hour of sleep per night for a week causes cognitive impairment equivalent to a.10 blood alcohol level. You can get fired for showing up drunk, but an all-nighter is fine.

Irrespective of how well you were able to get on with your day after that most recent night without sleep, it is unlikely that you felt especially upbeat and joyous about the world. Your more-negative-than-usual perspective will have resulted from a generalized low mood, which is a normal consequence of being overtired. More important than just the mood, this mind-set is often accompanied by decreases in willingness to think and act proactively, control impulses, feel positive about yourself, empathize with others, and generally use emotional intelligence. Source: The Secret World of Sleep: The Surprising Science of the Mind at Rest

To be productive, don't overwork and get enough sleep. If you're not productive, lack of sleep may be to blame. James Maas, a sleep researcher and expert, said 7/10 Americans don't get enough sleep.

Did you know?

• Leonardo da Vinci slept little at night and frequently took naps.

• Napoleon, the French emperor, had no qualms about napping. He splurged every day.

• Even though Thomas Edison felt self-conscious about his napping behavior, he regularly engaged in this ritual.

• President Franklin D. Roosevelt's wife Eleanor used to take naps before speeches to increase her energy.

• The Singing Cowboy, Gene Autry, was known for taking regular naps in his dressing area in between shows.

• Every day, President John F. Kennedy took a siesta after eating his lunch in bed.

• Every afternoon, oil businessman and philanthropist John D. Rockefeller took a nap in his office.

• It was unavoidable for Winston Churchill to take an afternoon snooze. He thought it enabled him to accomplish twice as much each day.

• Every afternoon around 3:30, President Lyndon B. Johnson took a nap to divide his day into two segments.

• Ronald Reagan, the 40th president, was well known for taking naps as well.

Source: 5 Reasons Why You Should Take a Nap Every Day — Michael Hyatt

Since I started getting 7 to 8 hours of sleep a night, I've been more productive and completed more work than when I worked 16 hours a day. Who knew marketers could use sleep?

2. Refrain from accepting too frequently

Pareto's principle states that 20% of effort produces 80% of results, but 20% of results takes 80% of effort. Instead of working harder, we should prioritize the initiatives that produce the most outcomes. So we can focus on crucial tasks. Stop accepting unproductive tasks.

“The difference between successful people and very successful people is that very successful people say “no” to almost everything.” — Warren Buffett

What should you accept? Why say no? Consider doing a split test to determine if anything is worth your attention. Track what you do, how long it takes, and the consequences. Then, evaluate your list to discover what worked (or didn't) to optimize future chores.

Most of us say yes more often than we should, out of guilt, overextension, and because it's simpler than no. Nobody likes being awful.

Researchers separated 120 students into two groups for a 2012 Journal of Consumer Research study. One group was educated to say “I can't” while discussing choices, while the other used “I don't”.

The students who told themselves “I can’t eat X” chose to eat the chocolate candy bar 61% of the time. Meanwhile, the students who told themselves “I don’t eat X” chose to eat the chocolate candy bars only 36% of the time. This simple change in terminology significantly improved the odds that each person would make a more healthy food choice.

Next time you need to say no, utilize I don't to encourage saying no to unimportant things.

The 20-second rule is another wonderful way to avoid pursuits with little value. Add a 20-second roadblock to things you shouldn't do or bad habits you want to break. Delete social media apps from your phone so it takes you 20 seconds to find your laptop to access them. You'll be less likely to engage in a draining hobby or habit if you add an inconvenience.

Lower the activation energy for habits you want to adopt and raise it for habits you want to avoid. The more we can lower or even eliminate the activation energy for our desired actions, the more we enhance our ability to jump-start positive change. Source: The Happiness Advantage: The Seven Principles of Positive Psychology That Fuel Success and Performance at Work

3. Stop doing everything yourself and start letting people help you

I once managed a large community and couldn't do it alone. The community took over once I burned out. Members did better than I could have alone. I learned about community and user-generated content.

Consumers know what they want better than marketers. Octoly says user-generated videos on YouTube are viewed 10 times more than brand-generated videos. 51% of Americans trust user-generated material more than a brand's official website (16%) or media coverage (22%). (14 percent). Marketers should seek help from the brand community.

Being a successful content marketer isn't about generating the best content, but cultivating a wonderful community.

We should seek aid when needed. We can't do everything. It's best to delegate work so you may focus on the most critical things. Instead of overworking or doing things alone, let others help.

Having friends or coworkers around can boost your productivity even if they can't help.

Just having friends nearby can push you toward productivity. “There’s a concept in ADHD treatment called the ‘body double,’ ” says David Nowell, Ph.D., a clinical neuropsychologist from Worcester, Massachusetts. “Distractable people get more done when there is someone else there, even if he isn’t coaching or assisting them.” If you’re facing a task that is dull or difficult, such as cleaning out your closets or pulling together your receipts for tax time, get a friend to be your body double. Source: Friendfluence: The Surprising Ways Friends Make Us Who We Are

4. Give up striving for perfection

Perfectionism hinders professors' research output. Dr. Simon Sherry, a psychology professor at Dalhousie University, did a study on perfectionism and productivity. Dr. Sherry established a link between perfectionism and productivity.

Perfectionism has its drawbacks.

• They work on a task longer than necessary.

• They delay and wait for the ideal opportunity. If the time is right in business, you are already past the point.

• They pay too much attention to the details and miss the big picture.

Marketers await the right time. They miss out.

The perfect moment is NOW.

5. Automate monotonous chores instead of continuing to do them.

A team of five workers who spent 3%, 20%, 25%, 30%, and 70% of their time on repetitive tasks reduced their time spent to 3%, 10%, 15%, 15%, and 10% after two months of working to improve their productivity.

Last week, I wrote a 15-minute Python program. I wanted to generate content utilizing Twitter API data and Hootsuite to bulk schedule it. Automation has cut this task from a day to five minutes. Whenever I do something more than five times, I try to automate it.

Automate monotonous chores without coding. Skills and resources are nice, but not required.  If you cannot build it, buy it.

People forget time equals money. Manual work is easy and requires little investigation. You can moderate 30 Instagram photographs for your UGC campaign. You need digital asset management software to manage 30,000 photographs and movies from five platforms. Filemobile helps individuals develop more user-generated content. You may buy software to manage rich media and address most internet difficulties.

Hire an expert if you can't find a solution. Spend money to make money, and time is your most precious asset.

Visit GitHub or Google Apps Script library, marketers. You may often find free, easy-to-use open source code.

6. Stop relying on intuition and start supporting your choices with data.

You may optimize your life by optimizing webpages for search engines.

Numerous studies might help you boost your productivity. Did you know individuals are most distracted from midday to 4 p.m.? This is what a Penn State psychology professor found. Even if you can't find data on a particular question, it's easy to run a split test and review your own results.

7. Stop working and spend some time doing absolutely nothing.

Most people don't know that being too focused can be destructive to our work or achievements. The Boston Globe's The Power of Lonely says solo time is excellent for the brain and spirit.

One ongoing Harvard study indicates that people form more lasting and accurate memories if they believe they’re experiencing something alone. Another indicates that a certain amount of solitude can make a person more capable of empathy towards others. And while no one would dispute that too much isolation early in life can be unhealthy, a certain amount of solitude has been shown to help teenagers improve their moods and earn good grades in school. Source: The Power of Lonely

Reflection is vital. We find solutions when we're not looking.

We don't become more productive overnight. It demands effort and practice. Waiting for change doesn't work. Instead, learn about your body and identify ways to optimize your energy and time for a happy existence.