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.

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.

People are slowly recognizing entrepreneurship's downside.

Growing up, entrepreneurship wasn't common. High school class of 2012 had no entrepreneurs.

Businesses were different.

They had staff and a lengthy history of achievement.

I never wanted a business. It felt unattainable. My friends didn't care.

Weird.

People desired degrees to attain good jobs at big companies.

When graduated high school:

• 9 out of 10 people attend college

• Earn minimum wage (7%) working in a restaurant or retail establishment

• Or join the military (3%)

Later, entrepreneurship became a thing.

2014-ish

I was in the military and most of my high school friends were in college, so I didn't hear anything.

Entrepreneurship soared in 2015, according to Google Trends.

Then more individuals were interested. Entrepreneurship went from unusual to cool.

In 2015, it was easier than ever to build a website, run Facebook advertisements, and achieve organic social media reach.

There were several online business tools.

You didn't need to spend years or money figuring it out. Most entry barriers were gone.

Everyone wanted a side gig to escape the 95.

Small company applications have increased during the previous 10 years.

2011-2014 trend continues.

2015 adds 150,000 applications. 2016 adds 200,000. Plus 300,000 in 2017.

The graph makes it look little, but that's a considerable annual spike with no indications of stopping.

By 2021, new business apps had doubled.

Entrepreneurship will return to its early 2010s level.

I think we'll go backward in 5 years.

Entrepreneurship is half as popular as it was in 2015.

In the late 2020s and 30s, entrepreneurship will again be obscure.

Entrepreneurship's decade-long splendor is fading. People will cease escaping 9-5 and launch fewer companies.

That’s not a bad thing.

I think people have a rose-colored vision of entrepreneurship. It's fashionable. People feel that they're missing out if they're not entrepreneurial.

Reality is showing up.

People say on social media, "I knew starting a business would be hard, but not this hard."

More negative posts on entrepreneurship:

Luke adds:

Is being an entrepreneur ‘healthy’? I don’t really think so. Many like Gary V, are not role models for a well-balanced life. Despite what feel-good LinkedIn tells you the odds are against you as an entrepreneur. You have to work your face off. It’s a tough but rewarding lifestyle. So maybe let’s stop glorifying it because it takes a lot of (bleepin) work to survive a pandemic, mental health battles, and a competitive market.

Entrepreneurship is no longer a pipe dream.

It’s hard.

I went full-time in March 2020. I was done by April 2021. I had a good-paying job with perks.

When that fell through (on my start date), I had to continue my entrepreneurial path. I needed money by May 1 to pay rent.

Entrepreneurship isn't as great as many think.

Entrepreneurship is a serious business.

If you have a 9-5, the grass isn't greener here. Most people aren't telling the whole story when they post on social media or quote successful entrepreneurs.

People prefer to communicate their victories than their defeats.

Is this a bad thing?

I don’t think so.

Over the previous decade, entrepreneurship went from impossible to the finest thing ever.

It peaked in 2020-21 and is returning to reality.

Startups aren't for everyone.

If you like your job, don't quit.

Entrepreneurship won't amaze people if you quit your job.

It's irrelevant.

You're doomed.

And you'll probably make less money.

If you hate your job, quit. Change jobs and bosses. Changing jobs could net you a greater pay or better perks.

When you go solo, your paycheck and perks vanish. Did I mention you'll fail, sleep less, and stress more?

Nobody will stop you from pursuing entrepreneurship. You'll face several challenges.

Possibly.

Entrepreneurship may be romanticized for years.

Based on what I see from entrepreneurs on social media and trends, entrepreneurship is challenging and few will succeed.

Google announced 6% layoffs recently (or 12,000 people). This aligns it with most tech companies. A publicly contrite CEO explained that they had overhired during the COVID-19 pandemic boom and had to address it, but they were sorry and took full responsibility. I thought this was "bullshit" too. Meta, Amazon, Microsoft, and others must feel similarly. I spent 10 years at Google, and these things don't reflect well on the company's leaders.

All publicly listed companies have a fiduciary duty to act in the best interests of their shareholders. Dodge vs. Ford Motor Company established this (1919). Henry Ford wanted to reduce shareholder payments to offer cheaper cars and better wages. Ford stated.

My ambition is to employ still more men, to spread the benefits of this industrial system to the greatest possible number, to help them build up their lives and their homes. To do this we are putting the greatest share of our profits back in the business.

The Dodge brothers, who owned 10% of Ford, opposed this and sued Ford for the payments to start their own company. They won, preventing Ford from raising prices or salaries. If you have a vocal group of shareholders with the resources to sue you, you must prove you are acting in their best interests. Companies prioritize shareholders. Giving activist investors a stick to threaten you almost enshrines short-term profit over long-term thinking.

This underpins Google's current issues. Institutional investors who can sue Google see it as a wasteful company they can exploit. That doesn't mean you have to maximize profits (thanks to those who pointed out my ignorance of US corporate law in the comments and on HN), but it allows pressure. I feel for those navigating this. This is about unrestrained capitalism.

When Google went public, Larry Page and Sergey Brin knew the risks and worked hard to keep control. In their Founders' Letter to investors, they tried to set expectations for the company's operations.

Our long-term focus as a private company has paid off. Public companies do the same. We believe outside pressures lead companies to sacrifice long-term opportunities to meet quarterly market expectations.

The company has transformed since that letter. The company has nearly 200,000 full-time employees and a trillion-dollar market cap. Large investors have bought company stock because it has been a good long-term bet. Why are they restless now?

Other big tech companies emerged and fought for top talent. This has caused rising compensation packages. Google has also grown rapidly (roughly 22,000 people hired to the end of 2022). At $300,000 median compensation, those 22,000 people added $6.6 billion in salary overheads in 2022. Exorbitant. If the company still makes $16 billion every quarter, maybe not. Investors wonder if this value has returned.

Investors are right. Google uses people wastefully. However, by bluntly reducing headcount, they're not addressing the root causes and hurting themselves. No studies show that downsizing this way boosts productivity. There is plenty of evidence that they'll lose out because people will be risk-averse and distrust their leadership.

The company's approach also stinks. Finding out that you no longer have a job because you can’t log in anymore (sometimes in cases where someone is on call for protecting your production systems) is no way to fire anyone. Being with a narcissistic sociopath is like being abused. First, you receive praise and fancy perks for making the cut. You're fired by text and ghosted. You're told to appreciate the generous severance package. This firing will devastate managers and teams. This type of firing will take years to recover self-esteem. Senior management contributed to this. They chose the expedient answer, possibly by convincing themselves they were managing risk and taking the Macbeth approach of “If it were done when ’tis done, then ’twere well It were done quickly”.

Recap. Google's leadership did a stupid thing—mass firing—in a stupid way. How do we get rid of enough people to make investors happier? and "have 6% less people." Empathetic leaders should not emulate Elon Musk. There is no humane way to fire 12,000 people, but there are better ways. Why is Google so wasteful?

Ambition answers this. There aren't enough VP positions for a group of highly motivated, ambitious, and (increasingly) ruthless people. I’ve loitered around the edges of this world and a large part of my value was to insulate my teams from ever having to experience it. It’s like Game of Thrones played out through email and calendar and over video call.

Your company must look a certain way to be promoted to director or higher. You need the right people at the right levels under you. Long-term, growing your people will naturally happen if you're working on important things. This takes time, and you're never more than 6–18 months from a reorg that could start you over. Ambitious people also tend to be impatient. So, what do you do?

Hiring and vanity projects. To shape your company, you hire at the right levels. You value vanity metrics like active users over product utility. Your promo candidates get through by subverting the promotion process. In your quest for growth, you avoid performance managing people out. You avoid confronting toxic peers because you need their support for promotion. Your cargo cult gets you there.

Its ease makes Google wasteful. Since they don't face market forces, the employees don't see it as a business. Why would you do when the ads business is so profitable? Complacency causes senior leaders to prioritize their own interests. Empires collapse. Personal ambition often trumped doing the right thing for users, the business, or employees. Leadership's ambition over business is the root cause. Vanity metrics, mass hiring, and vague promises have promoted people to VP. Google goes above and beyond to protect senior leaders.

The decision-makers and beneficiaries are not the layoffees. Stock price increase beneficiaries. The people who will post on LinkedIn how it is about misjudging the market and how they’re so sorry and take full responsibility. While accumulating wealth, the dark room dwellers decide who stays and who goes. The billionaire investors. Google should start by addressing its bloated senior management, but — as they say — turkeys don't vote for Christmas. It should examine its wastefulness and make tough choices to fix it. A 6% cut is a blunt tool that admits you're not running your business properly. why aren’t the people running the business the ones shortly to be entering the job market?

This won't fix Google's wastefulness. The executives may never regain trust after their approach. Suppressed creativity. Business won't improve. Google will have lost its founding vision and us all. Large investors know they can force Google's CEO to yield. The rich will get richer and rationalize leaving 12,000 people behind. Cycles repeat.

It doesn’t have to be this way. In 2013, Nintendo's CEO said he wouldn't fire anyone for shareholders. Switch debuted in 2017. Nintendo's stock has increased by nearly five times, or 19% a year (including the drop most of the stock market experienced last year). Google wasted 12,000 talented people. To please rich people.