Dharmesh Shah co-founded HubSpot. WordPlay reached $90,000 per month in revenue without utilizing any of his wealth.

His method:

Take Advantage Of An Established Trend

Remember Wordle? Dharmesh was instantly hooked. As was the tech world.

HubSpot's co-founder noted inefficiencies in a recent My First Million episode. He wanted to play daily. Dharmesh, a tinkerer and software engineer, decided to design a word game.

He's a billionaire. How could he?

1. Wordle had limitations in his opinion;

2. Dharmesh is fundamentally a developer. He desired to start something new and increase his programming knowledge;

3. This project may serve as an excellent illustration for his son, who had begun learning about software development.

Better It Up

Building a new Wordle wasn't successful.

WordPlay lets you play with friends and family. You could challenge them and compare the results. It is a built-in growth tool.

WordPlay features:

• the capacity to follow sophisticated statistics after creating an account;

• continuous feedback on your performance;

• Outstanding domain name (wordplay.com).

Project Development

WordPlay has 9.5 million visitors and 45 million games played since February.

HubSpot co-founder credits tremendous growth to flywheel marketing, pushing the game through his own following.

Choosing an exploding specialty and making sharing easy also helped.

Shah enabled Google Ads on the website to test earning potential. Monthly revenue was $90,000.

That's just Google Ads. If monetization was the goal, a specialized ad network like Ezoic could double or triple the amount.

Wordle was a great buy for The New York Times at $1 million.

Higher startup valuations are often favorable for all parties. High valuations show a business's potential. New customers and talent are attracted. They earn respect.

Everyone benefits if a company's valuation rises.

Founders and investors have always been incentivized to overestimate a company's value.

Post-money valuations were inflated by 2021 market expectations and the valuation model's mechanisms.

Founders must understand both levers to handle a normalizing market.

2021, the year of miracles

2021 must've seemed miraculous to entrepreneurs, employees, and VCs. Valuations rose, and funding resumed after the first Covid-19 epidemic caution.

In 2021, VC investments increased from $335B to $643B. 518 new worldwide unicorns vs. 134 in 2020; 951 US IPOs vs. 431.

Things can change quickly, as 2020-21 showed.

Rising interest rates, geopolitical developments, and normalizing technology conditions drive down share prices and tech company market caps in 2022. Zoom, the poster-child of early lockdown success, is down 37% since 1st Jan.

Once-inflated valuations can become a problem in a normalizing market, especially for founders, employees, and early investors.

the reason why startups are always overvalued

To see why inflated valuations are a problem, consider one of its causes.

Private company values only fluctuate following a new investment round, unlike publicly-traded corporations. The startup's new value is calculated simply:

(Latest round share price) x (total number of company shares)

This is the industry standard Post-Money Valuation model.

Let’s illustrate how it works with an example. If a VC invests $10M for 1M shares (at $10/share), and the company has 10M shares after the round, its Post-Money Valuation is $100M (10/share x 10M shares).

This approach might seem like the most natural way to assess a business, but the model often unintentionally overstates the underlying value of the company even if the share price paid by the investor is fair. All shares aren't equal.

New investors in a corporation will always try to minimize their downside risk, or the amount they lose if things go wrong. New investors will try to negotiate better terms and pay a premium.

How the value of a struggling SpaceX increased

SpaceX's 2008 Series D is an example. Despite the financial crisis and unsuccessful rocket launches, the company's Post-Money Valuation was 36% higher after the investment round. Why?

Series D SpaceX shares were protected. In case of liquidation, Series D investors were guaranteed a 2x return before other shareholders.

Due to downside protection, investors were willing to pay a higher price for this new share class.

The Post-Money Valuation model overpriced SpaceX because it viewed all the shares as equal (they weren't).

Why entrepreneurs, workers, and early investors stand to lose the most

Post-Money Valuation is an effective and sufficient method for assessing a startup's valuation, despite not taking share class disparities into consideration.

In a robust market, where the firm valuation will certainly expand with the next fundraising round or exit, the inflated value is of little significance.

Fairness endures. If a corporation leaves at a greater valuation, each stakeholder will receive a proportional distribution. (i.e., 5% of a $100M corporation yields $5M).

SpaceX's inherent overvaluation was never a problem. Had it been sold for less than its Post-Money Valuation, some shareholders, including founders, staff, and early investors, would have seen their ownership drop.

The unforgiving world of 2022

In 2022, founders, employees, and investors who benefited from inflated values will face below-valuation exits and down-rounds.

For them, 2021 will be a curse, not a blessing.

Some tech giants are worried. Klarna's valuation fell from $45B (Oct 21) to $30B (Jun 22), Canvas from $40B to $27B, and GoPuffs from $17B to $8.3B.

Shazam and Blue Apron have to exit or IPO at a cheaper price. Premium share classes are protected, while others receive less. The same goes for bankrupts.

Those who continue at lower valuations will lose reputation and talent. When their value declines by half, generous employee stock options become less enticing, and their ability to return anything is questioned.

What can we infer about the present situation?

Such techniques to enhance your company's value or stop a normalizing market are fiction.

The current situation is a painful reminder for entrepreneurs and a crucial lesson for future firms.

The devastating market fall of the previous six months has taught us one thing:

1. Keep in mind that any valuation is speculative. Money Post A startup's valuation is a highly simplified approximation of its true value, particularly in the early phases when it lacks significant income or a cutting-edge product. It is merely a projection of the future and a hypothetical meter. Until it is achieved by an exit, a valuation is nothing more than a number on paper.
   

2. Assume the value of your company is lower than it was in the past. Your previous valuation might not be accurate now due to substantial changes in the startup financing markets. There is little reason to think that your company's value will remain the same given the 50%+ decline in many newly listed IT companies. Recognize how the market situation is changing and use caution.
   

3. Recognize the importance of the stake you hold. Each share class has a unique value that varies. Know the sort of share class you own and how additional contractual provisions affect the market value of your security. Frameworks have been provided by Metrick and Yasuda (Yale & UC) and Gornall and Strebulaev (Stanford) for comprehending the terms that affect investors' cash-flow rights upon withdrawal. As a result, you will be able to more accurately evaluate your firm and determine the worth of each share class.
   

4. Be wary of approving excessively protective share terms.
   The trade-offs should be considered while negotiating subsequent rounds. Accepting punitive contractual terms could first seem like a smart option in order to uphold your inflated worth, but you should proceed with caution. Such provisions ALWAYS result in misaligned shareholders, with common shareholders (such as you and your staff) at the bottom of the list.

The comeback tour continues…

First, he founded a $47 billion co-working company (sorry, a “tech company”).

He established WeLive to disrupt apartment life.

Then he created WeGrow, a school that tossed aside the usual curriculum to feed children's souls and release their potential.

He raised the world’s consciousness.

Then he blew it all up (without raising the world’s consciousness). (He bought a wave pool.)

Adam Neumann's WeWork business burned investors' money. The founder sailed off with unimaginable riches, leaving long-time employees with worthless stocks and the company bleeding money. His track record, which includes a failing baby clothing company, should have stopped investors cold.

Once the dust settled, folks went on. We forgot about the Neumanns! We forgot about the private jets, company retreats, many houses, and WeWork's crippling. In that moment, the prodigal son of entrepreneurship returned, choosing the blockchain as his industry. His homecoming tour began with Flowcarbon, which sold Goddess Nature Tokens to lessen companies' carbon footprints.

Did it work?

Of course not.

Despite receiving $70 million from Andreessen Horowitz's a16z, the project has been halted just two months after its announcement.

This triumph should lower his grade.

Neumann seems to have moved on and has another revolutionary idea for the future of living. Flow (not Flowcarbon) aims to help people live in flow and will launch in 2023. It's the classic Neumann pitch: lofty goals, yogababble, and charisma to attract investors.

It's a winning formula for one investment fund. a16z has backed the project with its largest single check, $350 million. It has a splash page and 3,000 rental units, but is valued at over $1 billion. The blog post praised Neumann for reimagining the office and leading a paradigm-shifting global company.

Flow's mission is to solve the nation's housing crisis. How? Idk. It involves offering community-centric services in apartment properties to the same remote workforce he once wooed with free beer and a pingpong table. Revolutionary! It seems the goal is to apply WeWork's goals of transforming physical spaces and building community to apartments to solve many of today's housing problems.

The elevator pitch probably sounded great.

At least a16z knows it's a near-impossible task, calling it a seismic shift. Marc Andreessen opposes affordable housing in his wealthy Silicon Valley town. As details of the project emerge, more investors will likely throw ethics and morals out the window to go with the flow, throwing money at a man known for burning through it while building toxic companies, hoping he can bank another fantasy valuation before it all crashes.

Insanity is repeating the same action and expecting a different result. Everyone on the Neumann hype train needs to sober up.

Like WeWork, this venture Won’tWork.

Like before, it'll cause a shitstorm.

Some AI-generated artworks sell for enormous sums of money.

But can you sell AI-Generated Artwork?

Simple answer: yes.

However, not all AI services enable allow usage and redistribution of images.

Let's check some of my favorite AI text-to-image generators:

• Dall-E2 by OpenAI

• MidJourney

• Dream by Wombo

Dall-E2 by OpenAI

The AI art generator Dall-E2 is powerful. Since it’s still in beta, you can join the waitlist here.

OpenAI DOES NOT allow the use and redistribution of any image for commercial purposes.

Here's the policy as of April 6, 2022.

Here are some images from Dall-E2’s webpage to show its art quality.

Several Reddit users reported receiving pricing surveys from OpenAI.

This suggests the company may bring out a subscription-based tier and a commercial license to sell images soon.

MidJourney

I like Midjourney's art generator. It makes great AI images. Here are some samples:

Standard Licenses are available for $10 per month.

Standard License allows you to use, copy, modify, merge, publish, distribute, and/or sell copies of the images, except for blockchain technologies.

If you utilize or distribute the Assets using blockchain technology, you must pay MidJourney 20% of revenue above $20,000 a month or engage in an alternative agreement.

Here's their copyright and trademark page.

Dream by Wombo

Dream is one of the first public AI art generators.

This AI program is free, easy to use, and Wombo gives a royalty-free license to copy or share artworks.

Users own all artworks generated by the tool. Including all related copyrights or intellectual property rights.

Here’s Wombos' intellectual property policy.

Final Reflections

AI is creating a new sort of art that's selling well. It’s becoming popular and valued, despite some skepticism.

Now that you know MidJourney and Wombo let you sell AI-generated art, you need to locate buyers. There are several ways to achieve this, but that’s for another story.

Apple's latest revelation may shock iPod fans and former owners.

Apple discontinued the iPod touch on May 11, 2022. After 21 years, Apple killed the last surviving iPod, a device Steve Jobs believed would revolutionize the music industry.

Jobs was used to making bold predictions, but few expected Apple's digital music player to change the music industry. It did.

This chaos created new business opportunities. Spotify, YouTube, and Amazon are products of that chaotic era.

As the digital landscape changes, so do consumers, and the iPod has lost favor. I'm sure Apple realizes the importance of removing an icon. The iPod was Apple like the Mac and iPhone. I think it's bold to retire such a key Apple cornerstone. What would Jobs do?

iPod evolution across the ages

Here's an iPod family tree for all you enthusiasts.

iPod vintage (Oct 2001 to Sep 2014, 6 generations)

The original iPod had six significant upgrades since 2001. Apple announced an 80 GB ($249) and 160 GB ($349) iPod classic in 2007.

Apple updated the 80 GB model with a 120 GB device in September 2008. Apple upgraded the 120 GB model with a 160 GB variant a year later (2009). This was the last iteration, and Apple discontinued the classic in September 2014.

iPod nano (Jan 2004 to Sep 2005, 2 generations)

Apple debuted a smaller, brightly-colored iPod in 2004. The first model featured 4 GB, enough for 1,000 songs.

Apple produced a new 4 GB or 6 GB iPod mini in February 2005 and discontinued it in September when they released a better-looking iPod nano.

iTouch nano (Sep 2005 to July 2017, 7 generations)

I loved the iPod nano. It was tiny and elegant with enough tech to please most music aficionados, unless you carry around your complete music collection.

Apple owed much of the iPod nano's small form and success to solid-state flash memory. Flash memory doesn't need power because it has no moving parts. This makes the iPod nano more durable than the iPod classic and mini, which employ hard drives.

Apple manufactured seven generations of the iPod nano, improving its design, display screen, memory, battery, and software, but abandoned it in July 2017 due to dwindling demand.

Shuffle iPod (Jan 2005 to Jul 2017, 4 generations)

The iPod shuffle was entry-level. It was a simple, lightweight, tiny music player. The iPod shuffle was perfect for lengthy bike trips, runs, and hikes.

Apple sold 10 million iPod shuffles in the first year and kept making them for 12 years, through four significant modifications.

iOS device (Sep 2007 to May 2022, 7 generations)

The iPod touch's bigger touchscreen interface made it a curious addition to the iPod family. The iPod touch resembled an iPhone more than the other iPods, making them hard to tell apart.

Many were dissatisfied that Apple removed functionality from the iPod touch to avoid making it too similar to the iPhone. Seven design improvements over 15 years brought the iPod touch closer to the iPhone, but not completely.

The iPod touch uses the same iOS operating system as the iPhone, giving it access to many apps, including handheld games.

The iPod touch's long production run is due to the next generation of music-loving gamers.

What made the iPod cool

iPod revolutionized music listening. It was the first device to store and play MP3 music, allowing you to carry over 1,000 songs anywhere.

The iPod changed consumer electronics with its scroll wheel and touchscreen. Jobs valued form and function equally. He showed people that a product must look good to inspire an emotional response and ignite passion.

The elegant, tiny iPod was a tremendous sensation when it arrived for $399 in October 2001. Even at this price, it became a must-have for teens to CEOs.

It's hard to identify any technology that changed how music was downloaded and played like the iPod. Apple iPod and iTunes had 63% of the paid music download market in the fourth quarter of 2012.

The demise of the iPod was inevitable

Apple discontinuing the iPod touch after 21 years is sad. This ends a 00s music icon.

Jobs was a genius at anticipating market needs and opportunities, and Apple launched the iPod at the correct time.

Few consumer electronics items have had such a lasting impact on music lovers and the music industry as the iPod.

Smartphones and social media have contributed to the iPod's decline. Instead of moving to the music, the new generation of consumers is focused on social media. They're no longer passive content consumers; they're active content creators seeking likes and followers. Here, the smartphone has replaced the iPod.

It's hard not to feel a feeling of loss, another part of my adolescence now forgotten by the following generation.

So, if you’re lucky enough to have a working iPod, hang on to that relic and enjoy the music and the nostalgia.

Consider yourself lucky if your last FAANG interview was rejected.

FAANG—Facebook, Apple, Amazon, Netflix, Google

(I know its manga now, but watch me not care)

These big companies offer many benefits.

1. large salaries and benefits

2. Prestige

3. high expectations for both you and your coworkers.

However, these jobs may have major drawbacks that only become apparent when you're thrown to the wolves, so it's up to you whether you see them as drawbacks or opportunities.

I know most college graduates start working at big tech companies because of their perceived coolness.

I've worked in these companies for years and can tell you what to expect if you get a job here.

Little fish in a vast ocean

The most obvious. Most billion/trillion-dollar companies employ thousands.

You may work on a small, unnoticed product part.

Directors and higher will sometimes make you redo projects they didn't communicate well without respecting your time, talent, or will to work on trivial stuff that doesn't move company needles.

Peers will only say, "Someone has to take out the trash," even though you know company resources are being wasted.

The power imbalance is frustrating.

What you can do about it

Know your WHY. Consider long-term priorities. Though riskier, I stayed in customer-facing teams because I loved building user-facing products.

This increased my impact. However, if you enjoy helping coworkers build products, you may be better suited for an internal team.

I told the Directors and Vice Presidents that their actions could waste Engineering time, even though it was unpopular. Some were receptive, some not.

I kept having tough conversations because they were good for me and the company.

However, some of my coworkers praised my candor but said they'd rather follow the boss.

An outdated piece of technology can take years to update.

Apple introduced Swift for iOS development in 2014. Most large tech companies adopted the new language after five years.

This is frustrating if you want to learn new skills and increase your market value.

Knowing that my lack of Swift practice could hurt me if I changed jobs made writing verbose Objective C painful.

What you can do about it

1. Work on the new technology in side projects; one engineer rewrote the Lyft app in Swift over the course of a weekend and promoted its adoption throughout the entire organization.

2. To integrate new technologies and determine how to combine legacy and modern code, suggest minor changes to the existing codebase.

Most managers spend their entire day in consecutive meetings.

After their last meeting, the last thing they want is another meeting to discuss your career goals.

Sometimes a manager has 15-20 reports, making it hard to communicate your impact.

Misunderstandings and stress can result.

Especially when the manager should focus on selfish parts of the team. Success won't concern them.

What you can do about it

1. Tell your manager that you are a self-starter and that you will pro-actively update them on your progress, especially if they aren't present at the meetings you regularly attend.

2. Keep being proactive and look for mentorship elsewhere if you believe your boss doesn't have enough time to work on your career goals.

3. Alternately, look for a team where the manager has more authority to assist you in making career decisions.

After a certain point, company loyalty can become quite harmful.

Because big tech companies create brand loyalty, too many colleagues stayed in unhealthy environments.

When you work for a well-known company and strangers compliment you, it's fun to tell your friends.

Work defines you. This can make you stay too long even though your career isn't progressing and you're unhappy.

Google may become your surname.

Workplaces are not families.

If you're unhappy, don't stay just because they gave you the paycheck to buy your first home and make you feel like you owe your life to them.

Many employees stayed too long. Though depressed and suicidal.

What you can do about it

1. Your life is not worth a company.

2. Do you want your job title and workplace to be listed on your gravestone? If not, leave if conditions deteriorate.

3. Recognize that change can be challenging. It's difficult to leave a job you've held for a number of years.

4. Ask those who have experienced this change how they handled it.

You still have a bright future if you were rejected from FAANG interviews.

Rejections only lead to amazing opportunities. If you're young and childless, work for a startup.

Companies may pay more than FAANGs. Do your research.

Ask recruiters and hiring managers tough questions about how the company and teams prioritize respectful working hours and boundaries for workers.

I know many 15-year-olds who have a lifelong dream of working at Google, and it saddens me that they're chasing a name on their resume instead of excellence.

This article is not meant to discourage you from working at these companies, but to share my experience about what HR/managers will never mention in interviews.

Read both sides before signing the big offer letter.