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.

Reflections on the closed company Hola! Dating app

I'll discuss my fuckups as an entrepreneur and CEO. All of them refer to the dating app Hola!, which I co-founded and starred in.

Spring 2021 was when we started. Two techies and two non-techies created a dating app. Pokemon Go and Tinder were combined.

Online dating is a business, and it takes two weeks from a like to a date. We questioned online dating app users if they met anyone offline last year.

75% replied yes, 50% sometimes, 25% usually.

Offline dating is popular, yet people have concerns.

• Men are reluctant to make mistakes in front of others.

• Women are curious about the background of everyone who approaches them.

We designed unique mechanics that let people date after a match. No endless chitchat. Women would be safe while men felt like cowboys.

I wish to emphasize three faults that lead to founders' estrangement.

This detachment ultimately led to us shutting down the company.

The wrong technology stack

Situation

Instead of generating a faster MVP and designing an app in a universal stack for iOS and Android, I argued we should pilot the app separately for iOS and Android. Technical founders' expertise made this possible.

Self-reflection

Mistaken strategy. We lost time and resources developing two apps at once. We chose iOS since it's more profitable. Apple took us out after the release, citing Guideline 4.3 Spam. After 4 months, we had nothing. We had a long way to go to get the app on Android and the Store.

I suggested creating a uniform platform for the company's growth. This makes parallel product development easier. The strategist's lack of experience and knowledge made it a piece of crap.

What would I have changed if I could?

We should have designed an Android universal stack. I expected Apple to have issues with a dating app.

Our approach should have been to launch something and subsequently improve it, but prejudice won.

The lesson

Discuss the IT stack with your CTO. It saves time and money. Choose the easiest MVP method.

2. A tardy search for investments

Situation

Though the universe and other founders encouraged me to locate investors first, I started pitching when we almost had an app.

When angels arrived, it was time to close. The app was banned, war broke out, I left the country, and the other co-founders stayed. We had no savings.

Self-reflection

I loved interviewing users. I'm proud of having done 1,000 interviews. I wanted to understand people's pain points and improve the product.

Interview results no longer affected the product. I was terrified to start pitching. I filled out accelerator applications and redid my presentation. You must go through that so you won't be terrified later.

What would I have changed if I could?

Get an external or internal mentor to help me with my first pitch as soon as possible. I'd be supported if criticized. He'd cheer with me if there was enthusiasm.

In 99% of cases, I'm comfortable jumping into the unknown, but there are exceptions. The mentor's encouragement would have prompted me to act sooner.

The lesson

Begin fundraising immediately. Months may pass. Show investors your pre-MVP project. Draw inferences from feedback.

3. Role ambiguity

Situation

My technical co-founders were also part-time lead developers, which produced communication issues. As co-founders, we communicated well and recognized the problems. Stakes, vesting, target markets, and approach were agreed upon.

We were behind schedule. Technical debt and strategic gap grew.

Bi-daily and weekly reviews didn't help. Each time, there were explanations. Inside, I was freaking out.

Self-reflection

I am a fairly easy person to talk to. I always try to stick to agreements; otherwise, my head gets stuffed with unnecessary information, interpretations, and emotions.

Sit down -> talk -> decide -> do -> evaluate the results. Repeat it.

If I don't get detailed comments, I start ruining everyone's mood. If there's a systematic violation of agreements without a good justification, I won't join the project or I'll end the collaboration.

What would I have done otherwise?

This is where it’s scariest to draw conclusions. Probably the most logical thing would have been not to start the project as we started it. But that was already a completely different project. So I would not have done anything differently and would have failed again.

But I drew conclusions for the future.

The lesson

First-time founders should find an adviser or team coach for a strategic session. It helps split the roles and responsibilities.

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.

Restructuring and layoffs cause career reevaluation. Your career can benefit.

Once you become institutionalized, the corporate ladder is all you know.

You're bubbled. Extremists term it the corporate Matrix. I'm not so severe because the business world brainwashed me, too.

This boosted my corporate career.

Until I hit bottom.

15 months later, I view my corporate life differently. You may wish to advance professionally. Read this before you do.

Your happiness in the workplace may be deceptive.

I've been fortunate to spend time with corporate aces.

Working for 2.5 years in banking social media gave me some of these experiences. Earlier in my career, I recorded interviews with business leaders.

These people have titles like Chief General Manager and Head Of. New titles brought life-changing salaries.

They seemed happy.

I’d pass them in the hallway and they’d smile or shake my hand. I dreamt of having their life.

The ominous pattern

Unfiltered talks with some of them revealed a different world.

They acted well. They were skilled at smiling and saying the correct things. All had the same dark pattern, though.

Something felt off.

I found my conversations with them were generally for their benefit. They hoped my online antics as a writer/coach would shed light on their dilemma.

They'd tell me they wanted more. When you're one position away from CEO, it's hard not to wonder if this next move will matter.

What really displeased corporate ladder chasers

Before ascending further, consider these.

Zero autonomy

As you rise in a company, your days get busier.

Many people and initiatives need supervision. Everyone expects you to know business details. Weak when you don't. A poor leader is fired during the next restructuring and left to pursue their corporate ambition.

Full calendars leave no time for reflection. You can't have a coffee with a friend or waste a day.

You’re always on call. It’s a roll call kinda life.

Unable to express oneself freely

My 8 years of LinkedIn writing helped me meet these leaders.

I didn't think they'd care. Mistake.

Corporate leaders envied me because they wanted to talk freely again without corporate comms or a PR firm directing them what to say.

They couldn't share their flaws or inspiring experiences.

They wanted to.

Every day they were muzzled eroded by their business dream.

Limited family time

Top leaders had families.

They've climbed the corporate ladder. Nothing excellent happens overnight.

Corporate dreamers rarely saw their families.

Late meetings, customer functions, expos, training, leadership days, team days, town halls, and product demos regularly occurred after work.

Or they had to travel interstate or internationally for work events. They used bags and motel showers.

Initially, they said business class flights and hotels were nice. They'd get bored. 5-star hotels become monotonous.

No hotel beats home.

One leader said he hadn't seen his daughter much. They used to Facetime, but now that he's been gone so long, she rarely wants to talk to him.

So they iPad-parented.

You're miserable without your family.

Held captive by other job titles

Going up the business ladder seems like a battle.

Leaders compete for business gains and corporate advancement.

I saw shocking filthy tricks. Leaders would lie to seem nice.

Captives included top officials.

A different section every week. If they ran technology, the Head of Sales would argue their CRM cost millions. Or an Operations chief would battle a product team over support requests.

After one conflict, another began.

Corporate echelons are antagonistic. Huge pay and bonuses guarantee bad behavior.

Overly centered on revenue

As you rise, revenue becomes more prevalent. Most days, you'd believe revenue was everything. Here’s the problem…

Numbers drain us.

Unless you're a closet math nerd, contemplating and talking about numbers drains your creativity.

Revenue will never substitute impact.

Incapable of taking risks

Corporate success requires taking fewer risks.

Risks can cause dismissal. Risks can interrupt business. Keep things moving so you may keep getting paid your enormous salary and bonus.

Restructuring or layoffs are inevitable. All corporate climbers experience it.

On this fateful day, a small few realize the game they’ve been trapped in and escape. Most return to play for a new company, but it takes time.

Addiction keeps them trapped. You know nothing else. The rest is strange.

You start to think “I’m getting old” or “it’s nearly retirement.” So you settle yet again for the trappings of the corporate ladder game to nowhere.

Should you climb the corporate ladder?

Let me end on a surprising note.

Young people should ascend the corporate ladder. It teaches you business skills and helps support your side gig and (potential) online business.

Don't get trapped, shackled, or muzzled.

Your ideas and creativity become stifled after too much gaming play.

Corporate success won't bring happiness.

Find fulfilling employment that matters. That's it.

10-sketch explanation

Choosing Tasks

Bringing News

carrying out 1:1s

providing critique

Managing Turbulence

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.