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.

A top-down company plan facilitates decision-making and impresses investors.

A startup business plan starts with the product, the target customers, how to reach them, and how to grow the business.

Bottom-up is terrific unless venture investors fund it.

If it can prove how it can exceed $100M in sales, investors will invest. If not, the business may be wonderful, but it's not venture capital-investable.

As a rule, venture investors only fund firms that expect to reach $100M within 5 years.

Investors get nothing until an acquisition or IPO. To make up for 90% of failed investments and still generate 20% annual returns, portfolio successes must exit with a 25x return. A $20M-valued company must be acquired for $500M or more.

This requires $100M in sales (or being on a nearly vertical trajectory to get there). The company has 5 years to attain that milestone and create the requisite ROI.

This motivates venture investors (venture funds and angel investors) to hunt for $100M firms within 5 years. When you pitch investors, you outline how you'll achieve that aim.

I'm wary of pitches after seeing a million hockey sticks predicting $5M to $100M in year 5 that never materialized. Doubtful.

Startups fail because they don't have enough clients, not because they don't produce a great product. That jump from $5M to $100M never happens. The company reaches $5M or $10M, growing at 10% or 20% per year.  That's great, but not enough for a $500 million deal.

Once it becomes clear the company won’t reach orbit, investors write it off as a loss. When a corporation runs out of money, it's shut down or sold in a fire sale. The company can survive if expenses are trimmed to match revenues, but investors lose everything.

When I hear a pitch, I'm not looking for bright income projections but a viable plan to achieve them. Answer these questions in your pitch.

• Is the market size sufficient to generate $100 million in revenue?

• Will the initial beachhead market serve as a springboard to the larger market or as quicksand that hinders progress?

• What marketing plan will bring in $100 million in revenue? Is the market diffuse and will cost millions of dollars in advertising, or is it one, focused market that can be tackled with a team of salespeople?

• Will the business be able to bridge the gap from a small but fervent set of early adopters to a larger user base and avoid lock-in with their current solution?

• Will the team be able to manage a $100 million company with hundreds of people, or will hypergrowth force the organization to collapse into chaos?

• Once the company starts stealing market share from the industry giants, how will it deter copycats?

The requirement to reach $100M may be onerous, but it provides a context for difficult decisions: What should the product be? Where should we concentrate? who should we hire? Every strategic choice must consider how to reach $100M in 5 years.

Focusing on $100M streamlines investor pitches. Instead of explaining everything, focus on how you'll attain $100M.

As an investor, I know I'll lose my money if the startup doesn't reach this milestone, so the revenue prediction is the first thing I look at in a pitch deck.

Reaching the $100M goal needs to be the first thing the entrepreneur thinks about when putting together the business plan, the central story of the pitch, and the criteria for every important decision the company makes.

Price Intelligently put out amazing content on pricing your SaaS product. This blog's link to the whole report is worth reading. Our key takeaways are below.

Don't base prices on the competition. Competitor-based pricing has clear drawbacks. Their pricing approach is yours. Your company offers customers something unique. Otherwise, you wouldn't create it. This strategy is static, therefore you can't add value by raising prices without outpricing competitors. Look, but don't touch is the competitor-based moral. You want to know your competitors' prices so you're in the same ballpark, but they shouldn't guide your selections. Competitor-based pricing also drives down prices.

Value-based pricing wins. This is customer-based pricing. Value-based pricing looks outward, not inward or laterally at competitors. Your clients are the best source of pricing information. By valuing customer comments, you're focusing on buyers. They'll decide if your pricing and packaging are right. In addition to asking consumers about cost savings or revenue increases, look at data like number of users, usage per user, etc.

Value-based pricing increases prices. As you learn more about the client and your worth, you'll know when and how much to boost rates. Every 6 months, examine pricing.

Cloning top customers. You clone your consumers by learning as much as you can about them and then reaching out to comparable people or organizations. You can't accomplish this without knowing your customers. Segmenting and reproducing them requires as much detail as feasible. Offer pricing plans and feature packages for 4 personas. The top plan should state Contact Us. Your highest-value customers want more advice and support.

Question your 4 personas. What's the one item you can't live without? Which integrations matter most? Do you do analytics? Is support important or does your company self-solve? What's too cheap? What's too expensive?

Not everyone likes per-user pricing. SaaS organizations often default to per-user analytics. About 80% of companies utilizing per-user pricing should use an alternative value metric because their goods don't give more value with more users, so charging for them doesn't make sense.

At least 3:1 LTV/CAC. Break even on the customer within 2 years, and LTV to CAC is greater than 3:1. Because customer acquisition costs are paid upfront but SaaS revenues accrue over time, SaaS companies face an early financial shortfall while paying back the CAC.

ROI should be >20:1. Indeed. Ensure the customer's ROI is 20x the product's cost. Microsoft Office costs $80 a year, but consumers would pay much more to maintain it.

A/B Testing. A/B testing is guessing. When your pricing page varies based on assumptions, you'll upset customers. You don't have enough customers anyway. A/B testing optimizes landing pages, design decisions, and other site features when you know the problem but not pricing.

Don't discount. It cheapens the product, makes it permanent, and increases churn. By discounting, you're ruining your pricing analysis.

I was entering tens of millions of records per hour when I first published Slonik PostgreSQL client for Node.js. The data being entered was usually flat, making it straightforward to use INSERT INTO ... SELECT * FROM unnset() pattern. I advocated the unnest approach for inserting rows in groups (that was part I).

However, today I’ve found a better way: jsonb_to_recordset.

jsonb_to_recordset expands the top-level JSON array of objects to a set of rows having the composite type defined by an AS clause.

jsonb_to_recordset allows us to query and insert records from arbitrary JSON, like unnest. Since we're giving JSON to PostgreSQL instead of unnest, the final format is more expressive and powerful.

SELECT *
FROM json_to_recordset('[{"name":"John","tags":["foo","bar"]},{"name":"Jane","tags":["baz"]}]')
AS t1(name text, tags text[]);
 name |   tags
------+-----------
 John | {foo,bar}
 Jane | {baz}
(2 rows)

Let’s demonstrate how you would use it to insert data.

Inserting data using json_to_recordset

Say you need to insert a list of people with attributes into the database.

const persons = [
  {
    name: 'John',
    tags: ['foo', 'bar']
  },
  {
    name: 'Jane',
    tags: ['baz']
  }
];

You may be tempted to traverse through the array and insert each record separately, e.g.

for (const person of persons) {
  await pool.query(sql`
    INSERT INTO person (name, tags)
    VALUES (
      ${person.name},
      ${sql.array(person.tags, 'text[]')}
    )
  `);
}

It's easier to read and grasp when working with a few records. If you're like me and troubleshoot a 2M+ insert query per day, batching inserts may be beneficial.

What prompted the search for better alternatives.

Inserting using unnest pattern might look like this:

await pool.query(sql`
  INSERT INTO public.person (name, tags)
  SELECT t1.name, t1.tags::text[]
  FROM unnest(
    ${sql.array(['John', 'Jane'], 'text')},
    ${sql.array(['{foo,bar}', '{baz}'], 'text')}
  ) AS t1.(name, tags);
`);

You must convert arrays into PostgreSQL array strings and provide them as text arguments, which is unsightly. Iterating the array to create slices for each column is likewise unattractive.

However, with jsonb_to_recordset, we can:

await pool.query(sql`
  INSERT INTO person (name, tags)
  SELECT *
  FROM jsonb_to_recordset(${sql.jsonb(persons)}) AS t(name text, tags text[])
`);

In contrast to the unnest approach, using jsonb_to_recordset we can easily insert complex nested data structures, and we can pass the original JSON document to the query without needing to manipulate it.

In terms of performance they are also exactly the same. As such, my current recommendation is to prefer jsonb_to_recordset whenever inserting lots of rows or nested data structures.

A fraud, free-market, antifragility tale

Crypto's only rival is public opinion.

In less than a week, mainstream media, bloggers, and TikTokers turned on FTX's founder.

While some were surprised, almost everyone with a keyboard and a Twitter account predicted the FTX collapse. These financial oracles should have warned the 1.2 million people Sam Bankman-Fried duped.

After happening, unexpected events seem obvious to our brains. It's a bug and a feature because it helps us cope with disasters and makes our reasoning suck.

Nobody predicted the FTX debacle. Bloomberg? Politicians. Non-famous. No cryptologists. Who?

When FTX imploded, taking billions of dollars with it, an outrage bomb went off, and the resulting shockwave threatens the crypto market's existence.

As someone who lost more than $78,000 in a crypto scam in 2020, I can only understand people’s reactions.  When the dust settles and rationality returns, we'll realize this is a natural occurrence in every free market.

What specifically occurred with FTX? (Skip if you are aware.)

FTX is a cryptocurrency exchange where customers can trade with cash. It reached #3 in less than two years as the fastest-growing platform of its kind.

FTX's performance helped make SBF the crypto poster boy. Other reasons include his altruistic public image, his support for the Democrats, and his company Alameda Research.

Alameda Research made a fortune arbitraging Bitcoin.

Arbitrage trading uses small price differences between two markets to make money. Bitcoin costs $20k in Japan and $21k in the US. Alameda Research did that for months, making $1 million per day.

Later, as its capital grew, Alameda expanded its trading activities and began investing in other companies.

Let's now discuss FTX.

SBF's diabolic master plan began when he used FTX-created FTT coins to inflate his trading company's balance sheets. He used inflated Alameda numbers to secure bank loans.

SBF used money he printed himself as collateral to borrow billions for capital. Coindesk exposed him in a report.

One of FTX's early investors tweeted that he planned to sell his FTT coins over the next few months. This would be a minor event if the investor wasn't Binance CEO Changpeng Zhao (CZ).

The crypto space saw a red WARNING sign when CZ cut ties with FTX. Everyone with an FTX account and a brain withdrew money. Two events followed. FTT fell from $20 to $4 in less than 72 hours, and FTX couldn't meet withdrawal requests, spreading panic.

SBF reassured FTX users on Twitter. Good assets.

He lied.

SBF falsely claimed FTX had a liquidity crunch. At the time of his initial claims, FTX owed about $8 billion to its customers. Liquidity shortages are usually minor. To get cash, sell assets. In the case of FTX, the main asset was printed FTT coins.

Sam wouldn't get out of trouble even if he slashed the discount (from $20 to $4) and sold every FTT. He'd flood the crypto market with his homemade coins, causing the price to crash.

SBF was trapped. He approached Binance about a buyout, which seemed good until Binance looked at FTX's books.

Binance's tweet ended SBF, and he had to apologize, resign as CEO, and file for bankruptcy.

Bloomberg estimated Sam's net worth to be zero by the end of that week. 0!

But that's not all. Twitter investigations exposed fraud at FTX and Alameda Research. SBF used customer funds to trade and invest in other companies.

Thanks to the Twitter indie reporters who made the mainstream press look amateurish. Some Twitter detectives didn't sleep for 30 hours to find answers. Others added to existing threads. Memes were hilarious.

One question kept repeating in my bald head as I watched the Blue Bird. Sam, WTF?

Then I understood.

SBF wanted that FTX becomes a bank.

Think about this. FTX seems healthy a few weeks ago. You buy 2 bitcoins using FTX. You'd expect the platform to take your dollars and debit your wallet, right?

No. They give I-Owe-Yous.

FTX records owing you 2 bitcoins in its internal ledger but doesn't credit your account. Given SBF's tricks, I'd bet on nothing.

What happens if they don't credit my account with 2 bitcoins? Your money goes into FTX's capital, where SBF and his friends invest in marketing, political endorsements, and buying other companies.

Over its two-year existence, FTX invested in 130 companies. Once they make a profit on their purchases, they'll pay you and keep the rest.

One detail makes their strategy dumb. If all FTX customers withdraw at once, everything collapses.

Financially savvy people think FTX's collapse resembles a bank run, and they're right. SBF designed FTX to operate like a bank.

You expect your bank to open a drawer with your name and put $1,000 in it when you deposit $1,000. They deposit $100 in your drawer and create an I-Owe-You for $900. What happens to $900?

Let's sum it up: It's boring and headache-inducing.

When you deposit money in a bank, they can keep 10% and lend the rest. Fractional Reserve Banking is a popular method. Fractional reserves operate within and across banks.

Fractional reserve banking generates $10,000 for every $1,000 deposited. People will pay off their debt plus interest.

As long as banks work together and the economy grows, their model works well.

SBF tried to replicate the system but forgot two details. First, traditional banks need verifiable collateral like real estate, jewelry, art, stocks, and bonds, not digital coupons. Traditional banks developed a liquidity buffer. The Federal Reserve (or Central Bank) injects massive cash into troubled banks.

Massive cash injections come from taxpayers. You and I pay for bankers' mistakes and annual bonuses. Yes, you may think banking is rigged. It's rigged, but it's the best financial game in 150 years. We accept its flaws, including bailouts for too-big-to-fail companies.

Anyway.

SBF wanted Binance's bailout. Binance said no, which was good for the crypto market.

Free markets are resilient.

Nassim Nicholas Taleb coined the term antifragility.

“Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty. Yet, in spite of the ubiquity of the phenomenon, there is no word for the exact opposite of fragile. Let us call it antifragile. Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better.”

The easiest way to understand how antifragile systems behave is to compare them with other types of systems.

• Glass is like a fragile system. It snaps when shocked.

• Similar to rubber, a resilient system. After a stressful episode, it bounces back.

• A system that is antifragile is similar to a muscle. As it is torn in the gym, it gets stronger.

Time-changed things are antifragile. Culture, tech innovation, restaurants, revolutions, book sales, cuisine, economic success, and even muscle shape. These systems benefit from shocks and randomness in different ways, but they all pay a price for antifragility.

Same goes for the free market and financial institutions. Taleb's book uses restaurants as an example and ends with a reference to the 2008 crash.

“Restaurants are fragile. They compete with each other. But the collective of local restaurants is antifragile for that very reason. Had restaurants been individually robust, hence immortal, the overall business would be either stagnant or weak and would deliver nothing better than cafeteria food — and I mean Soviet-style cafeteria food. Further, it [the overall business] would be marred with systemic shortages, with once in a while a complete crisis and government bailout.”

Imagine the same thing with banks.

Independent banks would compete to offer the best services. If one of these banks fails, it will disappear. Customers and investors will suffer, but the market will recover from the dead banks' mistakes.

This idea underpins a free market. Bitcoin and other cryptocurrencies say this when criticizing traditional banking.

The traditional banking system's components never die. When a bank fails, the Federal Reserve steps in with a big taxpayer-funded check. This hinders bank evolution. If you don't let banking cells die and be replaced, your financial system won't be antifragile.

The interdependence of banks (centralization) means that one bank's mistake can sink the entire fleet, which brings us to SBF's ultimate travesty with FTX.

FTX has left the cryptocurrency gene pool.

FTX should be decentralized and independent. The super-star scammer invested in more than 130 crypto companies and linked them, creating a fragile banking-like structure. FTX seemed to say, "We exist because centralized banks are bad." But we'll be good, unlike the centralized banking system.

FTX saved several companies, including BlockFi and Voyager Digital.

FTX wanted to be a crypto bank conglomerate and Federal Reserve. SBF wanted to monopolize crypto markets. FTX wanted to be in bed with as many powerful people as possible, so SBF seduced politicians and celebrities.

Worst? People who saw SBF's plan flaws praised him. Experts, newspapers, and crypto fans praised FTX. When billions pour in, it's hard to realize FTX was acting against its nature.

Then, they act shocked when they realize FTX's fall triggered a domino effect. Some say the damage could wipe out the crypto market, but that's wrong.

Cell death is different from body death.

FTX is out of the game despite its size. Unfit, it fell victim to market natural selection.

Next?

The challengers keep coming. The crypto economy will improve with each failure.

Free markets are antifragile because their fragile parts compete, fostering evolution. With constructive feedback, evolution benefits customers and investors.

FTX shows that customers don't like being scammed, so the crypto market's health depends on them. Charlatans and con artists are eliminated quickly or slowly.

Crypto isn't immune to collapse. Cryptocurrencies can go extinct like biological species. Antifragility isn't immortality. A few more decades of evolution may be enough for humans to figure out how to best handle money, whether it's bitcoin, traditional banking, gold, or something else.

Keep your BS detector on. Start by being skeptical of this article's finance-related claims. Even if you think you understand finance, join the conversation.

We build a better future through dialogue. So listen, ask, and share. When you think you can't find common ground with the opposing view, remember:

Sam Bankman-Fried lied.