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.

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.

Open to ideas or acquisitions

Failure is an unavoidable aspect of life, yet many recoil at the word.

I've worked on unrelated startup projects. This is a list of products I developed (often as the tech lead or co-founder) and why they failed to launch.

Chess Bet (Betting)

As a chess player who plays 5 games a day and has an ELO rating of 2100, I tried to design a chess engine to rival stockfish and Houdini.

While constructing my chess engine, my cofounder asked me about building a p2p chess betting app. Chess Bet. There couldn't be a better time.

Two people in different locations could play a staked game. The winner got 90% of the bet and we got 10%. The business strategy was clear, but our mini-launch was unusual.

People started employing the same cheat engines I mentioned, causing user churn and defaming our product.

It was the first programming problem I couldn't solve after building a cheat detection system based on player move strengths and prior games. Chess.com, the most famous online chess software, still suffers from this.

We decided to pivot because we needed an expensive betting license.

We relaunched as Chess MVP after deciding to focus on chess learning. A platform for teachers to create chess puzzles and teach content. Several chess students used our product, but the target market was too tiny.

We chose to quit rather than persevere or pivot.

BodaCare (Insure Tech)

‘BodaBoda’ in Swahili means Motorcycle. My Dad approached me in 2019 (when I was working for a health tech business) about establishing an Insurtech/fintech solution for motorbike riders to pay for insurance using SNPL.

We teamed up with an underwriter to market motorcycle insurance. Once they had enough premiums, they'd get an insurance sticker in the mail. We made it better by splitting the cover in two, making it more reasonable for motorcyclists struggling with lump-sum premiums.

Lack of capital and changing customer behavior forced us to close, with 100 motorcyclists paying 0.5 USD every day. Our unit econ didn't make sense, and CAC and retention capital only dug us deeper.

Circle (Social Networking)

Having learned from both product failures, I began to understand what worked and what didn't. While reading through Instagram, an idea struck me.

Suppose social media weren't virtual.

Imagine meeting someone on your way home. Like-minded person

People were excited about social occasions after covid restrictions were eased. Anything to escape. I just built a university student-popular experiences startup. Again, there couldn't be a better time.

I started the Android app. I launched it on Google Beta and oh my! 200 people joined in two days.

It works by signaling if people are in a given place and allowing users to IM in hopes of meeting up in near real-time. Playstore couldn't deploy the app despite its success in beta for unknown reasons. I appealed unsuccessfully.

My infrastructure quickly lost users because I lacked funding.

In conclusion

This essay contains many failures, some of which might have been avoided and others not, but they were crucial learning points in my startup path.

If you liked any idea, I have the source code on Github.

Happy reading until then!

This is arguably the best three-minute demonstration I've ever seen of anything. Derek Sivers turns a shaky video of a lone dancing guy at a music festival into a leadership lesson.

A leader must have the courage to stand alone and appear silly. But what he's doing is so straightforward that it's almost instructive. This is critical. You must be simple to follow!

Now comes the first follower, who plays an important role: he publicly demonstrates how to follow. The leader embraces him as an equal, so it's no longer about the leader — it's about them, plural. He's inviting his friends to join him. It takes courage to be the first follower! You stand out and dare to be mocked. Being a first follower is a style of leadership that is underappreciated. The first follower elevates a lone nut to the position of leader. If the first follower is the spark that starts the fire, the leader is the flint.

This link was sent to me by @ottmark, who noted its resemblance to Kurt Vonnegut's three categories of specialists required for revolution.

The rarest of these specialists, he claims, is an actual genius – a person capable generating seemingly wonderful ideas that are not widely known. "A genius working alone is generally dismissed as a crazy," he claims.

The second type of specialist is much easier to find: a highly intellectual person in good standing in his or her community who understands and admires the genius's new ideas and can attest that the genius is not insane. "A person like him working alone can only crave loudly for changes, but fail to say what their shapes should be," Slazinger argues.

Jeff Veen reduced the three personalities to "the inventor, the investor, and the evangelist" on Twitter.

Jobs' secret emails became public due to a litigation with Samsung.

Steve Jobs sent Phil Schiller an email at the end of 2010. Top 100 A was the codename for Apple's annual Top 100 executive meetings. The 2011 one was scheduled.

Everything about this gathering is secret, even attendance. The location is hidden, and attendees can't even drive themselves. Instead, buses transport them to a 2-3 day retreat.

Due to a litigation with Samsung, this Top 100 meeting's agenda was made public in 2014. This was a critical milestone in Apple's history, not a Top 100 meeting. Apple had many obstacles in the 2010s to remain a technological leader. Apple made more money with non-PC goods than with its best-selling Macintosh series. This was the last Top 100 gathering Steve Jobs would attend before passing, and he wanted to make sure his messages carried on before handing over his firm to Tim Cook.

In this post, we'll discuss lessons from Jobs' meeting agenda. Two sorts of entrepreneurs can use these tips:

1. Those who manage a team in a business and must ensure that everyone is working toward the same goals, upholding the same principles, and being inspired by the same future.

2. Those who are sole proprietors or independent contractors and who must maintain strict self-discipline in order to stay innovative in their industry and adhere to their own growth strategy.

Here's Steve Jobs's email outlining the annual meeting agenda. It's an 11-part summary of the company's shape and strategy.

Steve Jobs outlines Apple's 2011 strategy, 10/24/10

1. Correct your data

Business leaders must comprehend their company's metrics. Jobs either mentions critical information he already knows or demands slides showing the numbers he wants. These numbers fall under 2 categories:

Metrics for growth and strategy

• As we will see, this was a crucial statistic for Apple since it signaled the beginning of the Post PC era and required them to make significant strategic changes in order to stay ahead of the curve. Post PC products now account for 66% of our revenues.

• Within six months, iPad outsold Mac, another sign of the Post-PC age. As we will see, Jobs thought the iPad would be the next big thing, and item number four on the agenda is one of the most thorough references to the iPad.

• Geographical analysis: Here, Jobs emphasizes China, where the corporation has a slower start than anticipated. China was dominating Apple's sales growth with 16% of revenue one year after this meeting.

Metrics for people & culture

• The individuals that make up a firm are more significant to its success than its headcount or average age. That holds true regardless of size, from a 5-person startup to a Fortune 500 firm. Jobs was aware of this, which is why his suggested agenda begins by emphasizing demographic data.

• Along with the senior advancements in the previous year's requested statistic, it's crucial to demonstrate that if the business is growing, the employees who make it successful must also grow.

2. Recognize the vulnerabilities and strengths of your rivals

Steve Jobs was known for attacking his competition in interviews and in his strategies and roadmaps. This agenda mentions 18 competitors, including:

• Google 7 times

• Android 3 times

• Samsung 2 times

Jobs' agenda email was issued 6 days after Apple's Q4 results call (2010). On the call, Jobs trashed Google and Android. His 5-minute intervention included:

• Google has acknowledged that the present iteration of Android is not tablet-optimized.

• Future Android tablets will not work (Dead On Arrival)

• While Google Play only has 90,000 apps, the Apple App Store has 300,000.

• Android is extremely fragmented and is continuing to do so.

• The App Store for iPad contains over 35,000 applications. The market share of the latest generation of tablets (which debuted in 2011) will be close to nil.

Jobs' aim in blasting the competition on that call was to reassure investors about the upcoming flood of new tablets. Jobs often criticized Google, Samsung, and Microsoft, but he also acknowledged when they did a better job. He was great at detecting his competitors' advantages and devising ways to catch up.

• Jobs doesn't hold back when he says in bullet 1 of his agenda: "We further lock customers into our ecosystem while Google and Microsoft are further along on the technology, but haven't quite figured it out yet tie all of our goods together."

• The plan outlined in bullet point 5 is immediately clear: catch up to Android where we are falling behind (notifications, tethering, and speech), and surpass them (Siri,). It's important to note that Siri frequently let users down and never quite lived up to expectations.

• Regarding MobileMe, see Bullet 6 Jobs admits that when it comes to cloud services like contacts, calendars, and mail, Google is far ahead of Apple.

3. Adapt or perish

Steve Jobs was a visionary businessman. He knew personal computers were the future when he worked on the first Macintosh in the 1980s.

Jobs acknowledged the Post-PC age in his 2010 D8 interview.

Will the tablet replace the laptop, Walt Mossberg questioned Jobs? Jobs' response:

“You know, when we were an agrarian nation, all cars were trucks, because that’s what you needed on the farm. As vehicles started to be used in the urban centers and America started to move into those urban and suburban centers, cars got more popular and innovations like automatic transmission and things that you didn’t care about in a truck as much started to become paramount in cars. And now, maybe 1 out of every 25 vehicles is a truck, where it used to be 100%. PCs are going to be like trucks. They’re still going to be around, still going to have a lot of value, but they’re going to be used by one out of X people.”

Imagine how forward-thinking that was in 2010, especially for the Macintosh creator. You have to be willing to recognize that things were changing and that it was time to start over and focus on the next big thing.

Post-PC is priority number 8 in his 2010 agenda's 2011 Strategy section. Jobs says Apple is the first firm to get here and that Post PC items account about 66% of our income. The iPad outsold the Mac in 6 months, and the Post-PC age means increased mobility (smaller, thinner, lighter). Samsung had just introduced its first tablet, while Apple was working on the iPad 3. (as mentioned in bullet 4).

4. Plan ahead (and different)

Jobs' agenda warns that Apple risks clinging to outmoded paradigms. Clayton Christensen explains in The Innovators Dilemma that huge firms neglect disruptive technologies until they become profitable. Samsung's Galaxy tab, released too late, never caught up to Apple.

Apple faces a similar dilemma with the iPhone, its cash cow for over a decade. It doesn't sell as much because consumers aren't as excited about new iPhone launches and because technology is developing and cell phones may need to be upgraded.

Large companies' established consumer base typically hinders innovation. Clayton Christensen emphasizes that loyal customers from established brands anticipate better versions of current products rather than something altogether fresh and new technologies.

Apple's marketing is smart. Apple's ecosystem is trusted by customers, and its products integrate smoothly. So much so that Apple can afford to be a disruptor by doing something no one has ever done before, something the world's largest corporation shouldn't be the first to try. Apple can test the waters and produce a tremendous innovation tsunami, something few corporations can do.

In March 2011, Jobs appeared at an Apple event. During his address, Steve reminded us about Apple's brand:

“It’s in Apple’s DNA, that technology alone is not enough. That it’s technology married with liberal arts, married with the humanities that yields us the results that make our hearts sink. And nowhere is that more true that in these Post-PC devices.“

More than a decade later, Apple remains one of the most innovative and trailblazing companies in the Post-PC world (industry-disrupting products like Airpods or the Apple Watch came out after that 2011 strategy meeting), and it has reinvented how we use laptops with its M1-powered line of laptops offering unprecedented performance.

A decade after Jobs' death, Apple remains the world's largest firm, and its former CEO had a crucial part in its expansion. If you can do 1% of what Jobs did, you may be 1% as successful.

Not bad.