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.

I've spent over 50 hours researching one-person firms, which interest me. I've found countless one-person enterprises that made millions on the founder's determination and perseverance.

Throughout my investigation, I found three of the most outstanding one-person enterprises. These enterprises show that people who work hard and dedicate themselves to their ideas may succeed.

Eric Barone (@ConcernedApe) created Stardew Valley in 2011 to better his job prospects. Eric loved making the game, in which players inherit a farm, grow crops, raise livestock, make friends with the villagers, and form a family.

Eric handled complete game production, including 3D graphics, animations, and music, to maintain creative control. He stopped job hunting and worked 8-15 hours a day on the game.

Eric developed a Stardew Valley website and subreddit to engage with gamers and get feedback. Eric's devoted community helped him meet Steam's minimum vote requirement for single creators.

Stardew Valley sold 1 million copies in two months after Eric launched it for $15 in 2016. The game has sold 20 million copies and made $300 million.

The game's inexpensive price, outsourcing of PR, marketing, and publication, and loyal player base helped it succeed. Eric has turned down million-dollar proposals from Sony and Nintendo to sell the game and instead updates and improves it. Haunted Chocolatier is Eric's new game.

Is farming not profitable? Ask Stardew Valley creator Eric Barone.

Gary Brewer established BuiltWith to assist users find website technologies and services. BuiltWith boasts 3000 paying customers and $14 million in yearly revenue, making it a significant resource for businesses wishing to generate leads, do customer analytics, obtain business insight, compare websites, or search websites by keyword.

BuiltWith has one full-time employee, Gary, and one or two part-time contractors that help with the blog. Gary handles sales, customer service, and other company functions alone.

BuiltWith acquired popularity through blog promotions and a top Digg ranking. About Us, a domain directory, connected to BuiltWith on every domain page, boosting it. Gary introduced $295–$995 monthly subscriptions to search technology, keywords, and potential consumers in response to customer demand.

Gary uses numerous methods to manage a firm without staff. He spends one to two hours every day answering user queries, most of which are handled quickly by linking to BuiltWiths knowledge store. Gary creates step-by-step essays or videos for complex problems. Gary can focus on providing new features based on customer comments and requests since he makes it easy to unsubscribe.

BuiltWith is entirely automated and successful due to its unique approach and useful offerings. It works for Google, Meta, Amazon, and Twitter.

Digital Inspiration develops Google Documents, Sheets, and Slides plugins. Digital Inspiration, founded by Amit Agarwal, receives 5 million monthly visits and earns $10 million. 40 million individuals have downloaded Digital Inspirations plugins.

Amit started Digital Inspiration by advertising his blog at tech events and getting Indian filter blogs and other newspapers to promote his articles. Amit built plugins and promoted them on the blog once the blog acquired popularity, using ideas from comments, friends, and Reddit. Digital Inspiration has over 20 free and premium plugins.

Mail Merge, Notifications for Google Forms, YouTube Uploader, and Document Studio are some of Digital Inspiration's most popular plugins. Mail Merge allows users to send personalized emails in bulk and track email opens and clicks.

Since Amits manages Digital Inspiration alone, his success is astounding. Amit developed a successful company via hard work and creativity, despite platform dependence. His tale inspires entrepreneurs.

SaaS spending is 40/40/20. 40% of operating expenses should be R&D, 40% sales and marketing, and 20% G&A. We wanted to see the statistics behind the rules of thumb. Since October 2017, 73 SaaS startups have gone public. Perhaps the rule of thumb should be 30/50/20. The data is below.

30/50/20. R&D accounts for 26% of opex, sales and marketing 48%, and G&A 22%. We think R&D/S&M/G&A should be 30/50/20.

There are outliers. There are exceptions to rules of thumb. Dropbox spent 45% on R&D whereas Zoom spent 13%. Zoom spent 73% on S&M, Dropbox 37%, and Bill.com 28%. Snowflake spent 130% of revenue on S&M, while their EBITDA margin is -192%.

G&A shouldn't stand out. Minimize G&A spending. Priorities should be product development and sales. Cloudflare, Sendgrid, Snowflake, and Palantir spend 36%, 34%, 37%, and 43% on G&A.

Another myth is that COGS is 20% of revenue. Median and averages are 29%.

Where is the profitability? Data-driven operating income calculations were simplified (Revenue COGS R&D S&M G&A). 20 of 73 IPO businesses reported operational income. Median and average operating income margins are -21% and -27%.

As long as you're growing fast, have outstanding retention, and marquee clients, you can burn cash since recurring income that doesn't churn is a valuable annuity.

The data was compelling overall. 30/50/20 is the new 40/40/20 for more established SaaS enterprises, unprofitability is alright as long as your business is expanding, and COGS can be somewhat more than 20% of revenue.

This is how to build a car while driving.

Building a high-growth startup is compared to building a car while it's speeding down the highway.

How to plan without going crazy? Or, without losing team, board, and investor buy-in?

I just delivered our company's product roadmap for the rest of the year. Complete. Thorough. Page-long. I'm optimistic about its chances of surviving as everything around us changes, from internal priorities to the global economy.

It's tricky. This isn't the first time I've created a startup roadmap. I didn't invent a document. It took time to deliver a document that will be relevant for months.

Goals matter.

Although they never change, goals are rarely understood.

This is the third in a series about a startup's unique roadmapping needs. Velocity is the intensity at which a startup must produce to survive.

A high-growth startup moves at breakneck speed, which I alluded to when I said priorities and economic factors can change daily or weekly.

At that speed, a startup's roadmap must be flexible, bend but not break, and be brief and to the point. I can't tell you how many startups and large companies develop a product roadmap every quarter and then tuck it away.

Big, wealthy companies can do this. It's suicide for a startup.

The drawer thing happens because startup product roadmaps are often valid for a short time. The roadmap is a random list of features prioritized by different company factions and unrelated to company goals.

It's not because the goals changed that a roadmap is shelved or ignored. Because the company's goals were never communicated or documented in the context of its product.

In the previous post, I discussed how to turn company goals into a product roadmap. In this post, I'll show you how to make a one-page startup roadmap.

In a future post, I'll show you how to follow this roadmap. This roadmap helps you track company goals, something a roadmap must do.

Be vague for growth, but direct for execution.

Here's my plan. The real one has more entries and more content in each.

Let's discuss smaller boxes.

Product developers and engineers know that the further out they predict, the more wrong they'll be. When developing the product roadmap, this rule is ignored. Then it bites us three, six, or nine months later when we haven't even started.

Why do we put everything in a product roadmap like a project plan?

Yes, I know. We use it when the product roadmap isn't goal-based.

A goal-based roadmap begins with a document that outlines each goal's idea, execution, growth, and refinement.

Once the goals are broken down into epics, initiatives, projects, and programs, only the idea and execution phases should be modeled. Any goal growth or refinement items should be vague and loosely mapped.

Why? First, any idea or execution-phase goal will result in growth initiatives that are unimaginable today. Second, internal priorities and external factors will change, but the goals won't. Locking items into calendar slots reduces flexibility and forces deviation from the single source of truth.

No soothsayers. Predicting the future is pointless; just prepare.

A map is useless if you don't know where you're going.

As we speed down the road, the car and the road will change. Goals define the destination.

This quarter and next quarter's roadmap should be set. After that, you should track destination milestones, not how to get there.

When you do that, even the most critical investors will understand the roadmap and buy in. When you track progress at the end of the quarter and revise your roadmap, the destination won't change.

While we played checkers, we thought billionaires played 3D chess. They're playing the same game on a fancier board.

Every medium has nuances and norms. Texting is authentic and casual. A smaller circle has access, creating intimacy and immediacy. Most people read all their texts, but not all their email and mail. Many of us no longer listen to our voicemails, and calling your kids ages you.

Live interviews and testimony under oath inspire real moments, rare in a world where communications departments sanitize everything powerful people say. When (some of) Elon's text messages became public in Twitter v. Musk, we got a glimpse into tech power. It's bowels.

These texts illuminate the tech community's upper caste.

Checkers, Not Chess

Elon texts with Larry Ellison, Joe Rogan, Sam Bankman-Fried, Satya Nadella, and Jack Dorsey. They reveal astounding logic, prose, and discourse. The world's richest man and his followers are unsophisticated, obtuse, and petty. Possibly. While we played checkers, we thought billionaires played 3D chess. They're playing the same game on a fancier board.

They fumble with their computers.

They lean on others to get jobs for their kids (no surprise).

No matter how rich, they always could use more (money).

Differences A social hierarchy exists. Among this circle, the currency of deference is... currency. Money increases sycophantry. Oculus and Elon's "friends'" texts induce nausea.

Autocorrect frustrates everyone.

Elon doesn't stand out to me in these texts; he comes off mostly OK in my view. It’s the people around him. It seems our idolatry of innovators has infected the uber-wealthy, giving them an uncontrollable urge to kill the cool kid for a seat at his cafeteria table. "I'd grenade for you." If someone says this and they're not fighting you, they're a fan, not a friend.

Many powerful people are undone by their fake friends. Facilitators, not well-wishers. When Elon-Twitter started, I wrote about power. Unchecked power is intoxicating. This is a scientific fact, not a thesis. Power causes us to downplay risk, magnify rewards, and act on instincts more quickly. You lose self-control and must rely on others.

You'd hope the world's richest person has advisers who push back when necessary (i.e., not yes men). Elon's reckless, childish behavior and these texts show there is no truth-teller. I found just one pushback in the 151-page document. It came from Twitter CEO Parag Agrawal, who, in response to Elon’s unhelpful “Is Twitter dying?” tweet, let Elon know what he thought: It was unhelpful. Elon’s response? A childish, terse insult.

Scale

The texts are mostly unremarkable. There are some, however, that do remind us the (super-)rich are different. Specifically, the discussions of possible equity investments from crypto-billionaire Sam Bankman-Fried (“Does he have huge amounts of money?”) and this exchange with Larry Ellison:

Ellison, who co-founded $175 billion Oracle, is wealthy. Less clear is whether he can text a billion dollars. Who hasn't been texted $1 billion? Ellison offered 8,000 times the median American's net worth, enough to buy 3,000 Ferraris or the Chicago Blackhawks. It's a bedrock principle of capitalism to have incredibly successful people who are exponentially wealthier than the rest of us. It creates an incentive structure that inspires productivity and prosperity. When people offer billions over text to help a billionaire's vanity project in a country where 1 in 5 children are food insecure, isn't America messed up?

Elon's Morgan Stanley banker, Michael Grimes, tells him that Web3 ventures investor Bankman-Fried can invest $5 billion in the deal: “could do $5bn if everything vision lock... Believes in your mission." The message bothers Elon. In Elon's world, $5 billion doesn't warrant a worded response. $5 billion is more than many small nations' GDP, twice the SEC budget, and five times the NRC budget.

If income inequality worries you after reading this, trust your gut.

Billionaires aren't like the rich.

As an entrepreneur, academic, and investor, I've met modest-income people, rich people, and billionaires. Rich people seem different to me. They're smarter and harder working than most Americans. Monty Burns from The Simpsons is a cartoon about rich people. Rich people have character and know how to make friends. Success requires supporters.

I've never noticed a talent or intelligence gap between wealthy and ultra-wealthy people. Conflating talent and luck infects the tech elite. Timing is more important than incremental intelligence when going from millions to hundreds of millions or billions. Proof? Elon's texting. Any man who electrifies the auto industry and lands two rockets on barges is a genius. His mega-billions come from a well-regulated capital market, enforceable contracts, thousands of workers, and billions of dollars in government subsidies, including a $465 million DOE loan that allowed Tesla to produce the Model S. So, is Mr. Musk a genius or an impressive man in a unique time and place?

The Point

Elon's texts taught us more? He can't "fix" Twitter. For two weeks in April, he was all in on blockchain Twitter, brainstorming Dogecoin payments for tweets with his brother — i.e., paid speech — while telling Twitter's board he was going to make a hostile tender offer. Kimbal approved. By May, he was over crypto and "laborious blockchain debates." (Mood.)

Elon asked the Twitter CEO for "an update from the Twitter engineering team" No record shows if he got the meeting. It doesn't "fix" Twitter either. And this is Elon's problem. He's a grown-up child with all the toys and no boundaries. His yes-men encourage his most facile thoughts, and shitposts and errant behavior diminish his genius and ours.

Post-Apocalyptic

The universe's titans have a sense of humor.

Every day, we must ask: Who keeps me real? Who will disagree with me? Who will save me from my psychosis, which has brought down so many successful people? Elon Musk doesn't need anyone to jump on a grenade for him; he needs to stop throwing them because one will explode in his hand.