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.

What they'll do is scarier.

My acquaintance recently joined a VC-funded startup. Money, equity, and upside possibilities were nice, but he had a nagging dread.

They just secured a $40M round and are hiring like crazy to prepare for their IPO in two years. All signals pointed to this startup's (a B2B IT business in a stable industry) success, and its equity-holding workers wouldn't pass that up.

Five months after starting the work, my friend struggled with leaving. We might overlook the awful culture and long hours at the proper price. This price plus the company's fate and survival abilities sent my friend departing in an unpleasant unplanned resignation before jumping on yet another sinking ship.

This affects founders. This affects VC-backed companies (and all businesses). This affects anyone starting, buying, or running a business.

Here's the under-the-table approach that's draining VC capital, leaving staff terrified (or jobless), founders rattled, and investors upset. How to recognize, solve, and avoid it

The unsettling reality behind door #1

You can't raise money off just your looks, right? If "looks" means your founding team's expertise, then maybe. In my friend's case, the founding team's strong qualifications and track records won over investors before talking figures.

They're hardly the only startup to raise money without a profitable customer acquisition strategy. Another firm raised money for an expensive sleep product because it's eco-friendly. They were off to the races with a few keywords and key players.

Both companies, along with numerous others, elected to invest on product development first. Company A employed all the tech, then courted half their market (they’re a tech marketplace that connects two parties). Company B spent millions on R&D to create a palatable product, then flooded the world with marketing.

My friend is on Company B's financial team, and he's seen where they've gone wrong. It's terrible.

Company A (tech market): Growing? Not quite. To achieve the ambitious expansion they (and their investors) demand, they've poured much of their little capital into salespeople: Cold-calling commission and salary salesmen. Is it working? Considering attrition and companies' dwindling capital, I don't think so.

Company B (green sleep) has been hiring, digital marketing, and opening new stores like crazy. Growing expenses should result in growing revenues and a favorable return on investment; if you grow too rapidly, you may neglect to check that ROI.

Once Company A cut headcount and Company B declared “going concerned”, my friend realized both startups had the same ailment and didn't recognize it.

I shouldn't have to ask a friend to verify a company's cash reserves and profitability to spot a financial problem. It happened anyhow.

The frightening part isn't that investors were willing to invest millions without product-market fit, CAC, or LTV estimates. That's alarming, but not as scary as the fact that startups aren't understanding the problem until VC rounds have dried up.

When they question consultants if their company will be around in 6 months. It’s a red flag. How will they stretch $20M through a 2-year recession with a $3M/month burn rate and no profitability? Alarms go off.

Who's in danger?

In a word, everyone who raised money without a profitable client acquisition strategy or enough resources to ride out dry spells.

Money mismanagement and poor priorities affect every industry (like sinking all your capital into your product, team, or tech, at the expense of probing what customer acquisition really takes and looks like).

This isn't about tech, real estate, or recession-proof luxury products. Fast, cheap, easy money flows into flashy-looking teams with buzzwords, trending industries, and attractive credentials.

If these companies can't show progress or get a profitable CAC, they can't raise more money. They die if they can't raise more money (or slash headcount and find shoestring budget solutions until they solve the real problem).

The kiss of death (and how to avoid it)

If you're running a startup and think raising VC is the answer, pause and evaluate. Do you need the money now?

I'm not saying VC is terrible or has no role. Founders have used it as a Band-Aid for larger, pervasive problems. Venture cash isn't a crutch for recruiting consumers profitably; it's rocket fuel to get you what and who you need.

Pay-to-play isn't a way to throw money at the wall and hope for a return. Pay-to-play works until you run out of money, and if you haven't mastered client acquisition, your cash will diminish quickly.

How can you avoid this bottomless pit? Tips:

• Understand your burn rate

• Keep an eye on your growth or profitability.

• Analyze each and every marketing channel and initiative.

• Make lucrative customer acquisition strategies and satisfied customers your top two priorities. not brand-new products. not stellar hires. avoid the fundraising rollercoaster to save time. If you succeed in these two tasks, investors will approach you with their thirsty offers rather than the other way around, and your cash reserves won't diminish as a result.

Not as much as your grandfather

My family friend always justified expensive, impractical expenditures by saying it was only monopoly money. In business, startups, and especially with money from investors expecting a return, that's not true.

More founders could understand that there isn't always another round if they viewed VC money as their own limited pool. When the well runs dry, you must refill it or save the day.

Venture financing isn't your grandpa's money. A discerning investor has entrusted you with dry powder in the hope that you'll use it wisely, strategically, and thoughtfully. Use it well.

40 years pass. After 14 years of retirement, you die. Am I the only one who sees the problem?

I’m the Jedi master of escaping the rat race.

Not to impress. I know this works since I've tried it. Quitting a job to make money online is worse than Kim Kardashian's internet-burning advice.

Let me help you rethink the move from a career to online income to f*ck you money.

To understand why a job is a joke, do some life math.

Without a solid why, nothing makes sense.

The retirement age is 65. Our processed food consumption could shorten our 79-year average lifespan.

You spend 40 years working.

After 14 years of retirement, you die.

Am I alone in seeing the problem?

Life is too short to work a job forever, especially since most people hate theirs. After-hours skills are vital.

Money equals unrestricted power, f*ck you.

F*ck you money is the answer.

Jack Raines said it first. He says we can do anything with the money. Jack, a young rebel straight out of college, can travel and try new foods.

F*ck you money signifies not checking your bank account before buying.

F*ck you” money is pure, unadulterated freedom with no strings attached.

Jack claims you're rich when you rarely think about money.

Avoid confusion.

This doesn't imply you can buy a Lamborghini. It indicates your costs, income, lifestyle, and bank account are balanced.

Jack established an online portfolio while working for UPS in Atlanta, Georgia. So he gained boundless power.

The portion that many erroneously believe

Yes, you need internet abilities to make money, but they're not different from 9-5 talents.

Sahil Lavingia, Gumroad's creator, explains.

A job is a way to get paid to learn.

Mistreat your boss 9-5. Drain his skills. Defuse him. Love and leave him (eventually).

Find another employment if yours is hazardous. Pick an easy job. Make sure nothing sneaks into your 6-12 time slot.

The dumb game that makes you a sheep

A 9-5 job requires many job interviews throughout life.

You email your résumé to employers and apply for jobs through advertisements. This game makes you a sheep.

You're competing globally. Work-from-home makes the competition tougher. If you're not the cheapest, employers won't hire you.

After-hours online talents (say, 6 pm-12 pm) change the game. This graphic explains it better:

Online talents boost after-hours opportunities.

You go from wanting to be picked to picking yourself. More chances equal more money. Your f*ck you fund gets the extra cash.

A novel method of learning is essential.

College costs six figures and takes a lifetime to repay.

Informal learning is distinct. 6-12pm:

• Observe the carefully controlled Twitter newsfeed.

• Make use of Teachable and Gumroad's online courses.

• Watch instructional YouTube videos

• Look through the top Substack newsletters.

Informal learning is more effective because it's not obvious. It's fun to follow your curiosity and hobbies.

The majority of people lack one attitude. It's simple to learn.

One big impediment stands in the way of f*ck you money and time independence. So often.

Too many people plan after 6-12 hours. Dreaming. Big-thinkers. Strategically. They fill their calendar with meetings.

This is after-hours masturb*tion.

Sahil Bloom reminded me that a bias towards action will determine if this approach works for you.

The key isn't knowing what to do from 6-12 a.m. Trust yourself and develop abilities as you go. It's for building the parachute after you jump.

Sounds risky. We've eliminated the risk by finishing this process after hours while you work 9-5.

With no risk, you can have an I-don't-care attitude and still be successful.

When you choose to move forward, this occurs.

Once you try 9-5/6-12, you'll tell someone.

It's bad.

Few of us hang out with problem-solvers.

It's how much of society operates. So they make reasons so they can feel better about not giving you money.

Matthew Kobach told me chasing f*ck you money is easier with like-minded folks.

Without f*ck you money friends, loneliness will take over and you'll think you've messed up when you just need to keep going.

Steal this easy guideline

Let's act. No more fluffing and caressing.

1. Learn

If you detest your 9-5 talents or don't think they'll work online, get new ones. If you're skilled enough, continue.

Easlo recommends these skills:

• Designer for Figma

• Designer Canva

• bubble creators

• editor in Photoshop

• Automation consultant for Zapier

• Designer of Webflow

• video editor Adobe

• Ghostwriter for Twitter

• Idea consultant

• Artist in Blender Studio

2. Develop the ability

Every night from 6-12, apply the skill.

Practicing ghostwriting? Write someone's tweets for free. Do someone's website copy to learn copywriting. Get a website to the top of Google for a keyword to understand SEO.

Free practice is crucial. Your 9-5 pays the money, so work for free.

3. Take off stealthily like a badass

Another mistake. Sell to few. Don't be the best. Don't claim expertise.

Sell your new expertise to others behind you.

Two ways:

• Using a digital good

• By providing a service,

Point 1 also includes digital service examples. Digital products include eBooks, communities, courses, ad-supported podcasts, and templates. It's easy. Your 9-5 job involves one of these.

Take ideas from work.

Why? They'll steal your time for profit.

4. Iterate while feeling awful

First-time launches always fail. You'll feel terrible. Okay. Remember your 9-5?

Find improvements. Ask free and paying consumers what worked.

Multiple relaunches, each 1% better.

5. Discover more

Never stop learning. Improve your skill. Add a relevant skill. Learn copywriting if you write online.

After-hours students earn the most.

6. Continue

Repetition is key.

7. Make this one small change.

Consistently. The 6-12 momentum won't make you rich in 30 days; that's success p*rn.

Consistency helps wage slaves become f*ck you money. Most people can't switch between the two.

Putting everything together

It's easy. You're probably already doing some.

This formula explains why, how, and what to do. It's a 5th-grade-friendly blueprint. Good.

Reduce financial risk with your 9-to-5. Replace Netflix with 6-12 money-making talents.

Life is short; do whatever you want. Today.

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.

Don't say this in public!

Want to wow your audience? Want to deliver a successful presentation? Do you want practical takeaways from your presentation?

Then avoid these phrases.

Public speaking is difficult. People fear public speaking, according to research.

"Public speaking is people's biggest fear, according to studies. Number two is death. "Sounds right?" — Comedian Jerry Seinfeld

Yes, public speaking is scary. These words and phrases will make your presentation harder.

Using unnecessary words can weaken your message.

You may have prepared well for your presentation and feel confident. During your presentation, you may freeze up. You may blank or forget.

Effective delivery is even more important than skillful public speaking.

Here are 10 presentation pitfalls.

1. I or Me

Presentations are about the audience, not you. Replace "I or me" with "you, we, or us." Focus on your audience. Reward them with expertise and intriguing views about your issue.

Serve your audience actionable items during your presentation, and you'll do well. Your audience will have a harder time listening and engaging if you're self-centered.

2. Sorry if/for

Your presentation is fine. These phrases make you sound insecure and unprepared. Don't pressure the audience to tell you not to apologize. Your audience should focus on your presentation and essential messages.

3. Excuse the Eye Chart, or This slide's busy

Why add this slide if you're utilizing these phrases? If you don't like this slide, change it before presenting. After the presentation, extra data can be provided.

Don't apologize for unclear slides. Hide or delete a broken PowerPoint slide. If so, divide your message into multiple slides or remove the "business" slide.

4. Sorry I'm Nervous

Some think expressing yourself will win over the audience. Nerves are horrible. Even public speakers are nervous.

Nerves aren't noticeable. What's the point? Let the audience judge your nervousness. Please don't make this obvious.

5. I'm not a speaker or I've never done this before.

These phrases destroy credibility. People won't listen and will check their phones or computers.

Why present if you use these phrases?

Good speakers aren't necessarily public speakers. Be confident in what you say. When you're confident, many people will like your presentation.

6. Our Key Differentiators Are

Overused term. It's widely utilized. This seems "salesy," and your "important differentiators" are probably like a competitor's.

This statement has been diluted; say, "what makes us different is..."

7. Next Slide

Many slides or stories? Your presentation needs transitions. They help your viewers understand your argument.

You didn't transition well when you said "next slide." Think about organic transitions.

8. I Didn’t Have Enough Time, or I’m Running Out of Time

The phrase "I didn't have enough time" implies that you didn't care about your presentation. This shows the viewers you rushed and didn't care.

Saying "I'm out of time" shows poor time management. It means you didn't rehearse enough and plan your time well.

9. I've been asked to speak on

This phrase is used to emphasize your importance. This phrase conveys conceit.

When you say this sentence, you tell others you're intelligent, skilled, and appealing. Don't utilize this term; focus on your topic.

10. Moving On, or All I Have

These phrases don't consider your transitions or presentation's end. People recall a presentation's beginning and end.

How you end your discussion affects how people remember it. You must end your presentation strongly and use natural transitions.

Conclusion

10 phrases to avoid in a presentation. I or me, sorry if or sorry for, pardon the Eye Chart or this busy slide, forgive me if I appear worried, or I'm really nervous, and I'm not good at public speaking, I'm not a speaker, or I've never done this before.

Please don't use these phrases: next slide, I didn't have enough time, I've been asked to speak about, or that's all I have.

We shouldn't make public speaking more difficult than it is. We shouldn't exacerbate a difficult issue. Better public speakers avoid these words and phrases.

“Remember not only to say the right thing in the right place, but far more difficult still, to leave unsaid the wrong thing at the tempting moment.” — Benjamin Franklin, Founding Father

This is a summary. See the original post here.

I've summarized each.

Anne Lamott said books are important. Books help us understand ourselves and our behavior. They teach us about community, friendship, and death.

I read. One of my few life-changing habits. 100+ books a year improve my life. I'll list life-changing books you can read in a day. I hope you like them too.

Let's get started!

1) Seneca's Letters from a Stoic

One of my favorite philosophy books. Ryan Holiday, Naval Ravikant, and other prolific readers recommend it.

Seneca wrote 124 letters at the end of his life after working for Nero. Death, friendship, and virtue are discussed.

It's worth rereading. When I'm in trouble, I consult Seneca.

It's brief. The book could be read in one day. However, use it for guidance during difficult times.

My favorite book quotes:

• Many men find that becoming wealthy only alters their problems rather than solving them.

• You will never be poor if you live in harmony with nature; you will never be wealthy if you live according to what other people think.

• We suffer more frequently in our imagination than in reality; there are more things that are likely to frighten us than to crush us.

2) Steven Pressfield's book The War of Art

I’ve read this book twice. I'll likely reread it before 2022 is over.

The War Of Art is the best productivity book. Steven offers procrastination-fighting tips.

Writers, musicians, and creative types will love The War of Art. Workplace procrastinators should also read this book.

My favorite book quotes:

• The act of creation is what matters most in art. Other than sitting down and making an effort every day, nothing else matters.

• Working creatively is not a selfish endeavor or an attempt by the actor to gain attention. It serves as a gift for all living things in the world. Don't steal your contribution from us. Give us everything you have.

• Fear is healthy. Fear is a signal, just like self-doubt. Fear instructs us on what to do. The more terrified we are of a task or calling, the more certain we can be that we must complete it.

3) Darren Hardy's The Compound Effect

The Compound Effect offers practical tips to boost productivity by 10x.

The author believes each choice shapes your future. Pizza may seem harmless. However, daily use increases heart disease risk.

Positive outcomes too. Daily gym visits improve fitness. Reading an hour each night can help you learn. Writing 1,000 words per day would allow you to write a novel in under a year.

Your daily choices affect compound interest and your future. Thus, better habits can improve your life.

My favorite book quotes:

• Until you alter a daily habit, you cannot change your life. The key to your success can be found in the actions you take each day.

• The hundreds, thousands, or millions of little things are what distinguish the ordinary from the extraordinary; it is not the big things that add up in the end.

• Don't worry about willpower. Time to use why-power. Only when you relate your decisions to your aspirations and dreams will they have any real meaning. The decisions that are in line with what you define as your purpose, your core self, and your highest values are the wisest and most inspiring ones. To avoid giving up too easily, you must want something and understand why you want it.