More on Leadership
Sam Hickmann
3 years ago
Improving collaboration with the Six Thinking Hats
Six Thinking Hats was written by Dr. Edward de Bono. "Six Thinking Hats" and parallel thinking allow groups to plan thinking processes in a detailed and cohesive way, improving collaboration.
Fundamental ideas
In order to develop strategies for thinking about specific issues, the method assumes that the human brain thinks in a variety of ways that can be intentionally challenged. De Bono identifies six brain-challenging directions. In each direction, the brain brings certain issues into conscious thought (e.g. gut instinct, pessimistic judgement, neutral facts). Some may find wearing hats unnatural, uncomfortable, or counterproductive.
The example of "mismatch" sensitivity is compelling. In the natural world, something out of the ordinary may be dangerous. This mode causes negative judgment and critical thinking.
Colored hats represent each direction. Putting on a colored hat symbolizes changing direction, either literally or metaphorically. De Bono first used this metaphor in his 1971 book "Lateral Thinking for Management" to describe a brainstorming framework. These metaphors allow more complete and elaborate thought separation. Six thinking hats indicate ideas' problems and solutions.
Similarly, his CoRT Thinking Programme introduced "The Five Stages of Thinking" method in 1973.
| HAT | OVERVIEW | TECHNIQUE |
|---|---|---|
| BLUE | "The Big Picture" & Managing | CAF (Consider All Factors); FIP (First Important Priorities) |
| WHITE | "Facts & Information" | Information |
| RED | "Feelings & Emotions" | Emotions and Ego |
| BLACK | "Negative" | PMI (Plus, Minus, Interesting); Evaluation |
| YELLOW | "Positive" | PMI |
| GREEN | "New Ideas" | Concept Challenge; Yes, No, Po |
Strategies and programs
After identifying the six thinking modes, programs can be created. These are groups of hats that encompass and structure the thinking process. Several of these are included in the materials for franchised six hats training, but they must often be adapted. Programs are often "emergent," meaning the group plans the first few hats and the facilitator decides what to do next.
The group agrees on how to think, then thinks, then evaluates the results and decides what to do next. Individuals or groups can use sequences (and indeed hats). Each hat is typically used for 2 minutes at a time, although an extended white hat session is common at the start of a process to get everyone on the same page. The red hat is recommended to be used for a very short period to get a visceral gut reaction – about 30 seconds, and in practice often takes the form of dot-voting.
| ACTIVITY | HAT SEQUENCE |
|---|---|
| Initial Ideas | Blue, White, Green, Blue |
| Choosing between alternatives | Blue, White, (Green), Yellow, Black, Red, Blue |
| Identifying Solutions | Blue, White, Black, Green, Blue |
| Quick Feedback | Blue, Black, Green, Blue |
| Strategic Planning | Blue, Yellow, Black, White, Blue, Green, Blue |
| Process Improvement | Blue, White, White (Other People's Views), Yellow, Black, Green, Red, Blue |
| Solving Problems | Blue, White, Green, Red, Yellow, Black, Green, Blue |
| Performance Review | Blue, Red, White, Yellow, Black, Green, Blue |
Use
Speedo's swimsuit designers reportedly used the six thinking hats. "They used the "Six Thinking Hats" method to brainstorm, with a green hat for creative ideas and a black one for feasibility.
Typically, a project begins with extensive white hat research. Each hat is used for a few minutes at a time, except the red hat, which is limited to 30 seconds to ensure an instinctive gut reaction, not judgement. According to Malcolm Gladwell's "blink" theory, this pace improves thinking.
De Bono believed that the key to a successful Six Thinking Hats session was focusing the discussion on a particular approach. A meeting may be called to review and solve a problem. The Six Thinking Hats method can be used in sequence to explore the problem, develop a set of solutions, and choose a solution through critical examination.
Everyone may don the Blue hat to discuss the meeting's goals and objectives. The discussion may then shift to Red hat thinking to gather opinions and reactions. This phase may also be used to determine who will be affected by the problem and/or solutions. The discussion may then shift to the (Yellow then) Green hat to generate solutions and ideas. The discussion may move from White hat thinking to Black hat thinking to develop solution set criticisms.
Because everyone is focused on one approach at a time, the group is more collaborative than if one person is reacting emotionally (Red hat), another is trying to be objective (White hat), and another is critical of the points which emerge from the discussion (Black hat). The hats help people approach problems from different angles and highlight problem-solving flaws.

Nir Zicherman
3 years ago
The Great Organizational Conundrum
Only two of the following three options can be achieved: consistency, availability, and partition tolerance
Someone told me that growing from 30 to 60 is the biggest adjustment for a team or business.
I remember thinking, That's random. Each company is unique. I've seen teams of all types confront the same issues during development periods. With new enterprises starting every year, we should be better at navigating growing difficulties.
As a team grows, its processes and systems break down, requiring reorganization or declining results. Why always? Why isn't there a perfect scaling model? Why hasn't that been found?
The Three Things Productive Organizations Must Have
Any company should be efficient and productive. Three items are needed:
First, it must verify that no two team members have conflicting information about the roadmap, strategy, or any input that could affect execution. Teamwork is required.
Second, it must ensure that everyone can receive the information they need from everyone else quickly, especially as teams become more specialized (an inevitability in a developing organization). It requires everyone's accessibility.
Third, it must ensure that the organization can operate efficiently even if a piece is unavailable. It's partition-tolerant.
From my experience with the many teams I've been on, invested in, or advised, achieving all three is nearly impossible. Why a perfect organization model cannot exist is clear after analysis.
The CAP Theorem: What is it?
Eric Brewer of Berkeley discovered the CAP Theorem, which argues that a distributed data storage should have three benefits. One can only have two at once.
The three benefits are consistency, availability, and partition tolerance, which implies that even if part of the system is offline, the remainder continues to work.
This notion is usually applied to computer science, but I've realized it's also true for human organizations. In a post-COVID world, many organizations are hiring non-co-located staff as they grow. CAP Theorem is more important than ever. Growing teams sometimes think they can develop ways to bypass this law, dooming themselves to a less-than-optimal team dynamic. They should adopt CAP to maximize productivity.
Path 1: Consistency and availability equal no tolerance for partitions
Let's imagine you want your team to always be in sync (i.e., for someone to be the source of truth for the latest information) and to be able to share information with each other. Only division into domains will do.
Numerous developing organizations do this, especially after the early stage (say, 30 people) when everyone may wear many hats and be aware of all the moving elements. After a certain point, it's tougher to keep generalists aligned than to divide them into specialized tasks.
In a specialized, segmented team, leaders optimize consistency and availability (i.e. every function is up-to-speed on the latest strategy, no one is out of sync, and everyone is able to unblock and inform everyone else).
Partition tolerance suffers. If any component of the organization breaks down (someone goes on vacation, quits, underperforms, or Gmail or Slack goes down), productivity stops. There's no way to give the team stability, availability, and smooth operation during a hiccup.
Path 2: Partition Tolerance and Availability = No Consistency
Some businesses avoid relying too heavily on any one person or sub-team by maximizing availability and partition tolerance (the organization continues to function as a whole even if particular components fail). Only redundancy can do that. Instead of specializing each member, the team spreads expertise so people can work in parallel. I switched from Path 1 to Path 2 because I realized too much reliance on one person is risky.
What happens after redundancy? Unreliable. The more people may run independently and in parallel, the less anyone can be the truth. Lack of alignment or updated information can lead to people executing slightly different strategies. So, resources are squandered on the wrong work.
Path 3: Partition and Consistency "Tolerance" equates to "absence"
The third, least-used path stresses partition tolerance and consistency (meaning answers are always correct and up-to-date). In this organizational style, it's most critical to maintain the system operating and keep everyone aligned. No one is allowed to read anything without an assurance that it's up-to-date (i.e. there’s no availability).
Always short-lived. In my experience, a business that prioritizes quality and scalability over speedy information transmission can get bogged down in heavy processes that hinder production. Large-scale, this is unsustainable.
Accepting CAP
When two puzzle pieces fit, the third won't. I've watched developing teams try to tackle these difficulties, only to find, as their ancestors did, that they can never be entirely solved. Idealized solutions fail in reality, causing lost effort, confusion, and lower production.
As teams develop and change, they should embrace CAP, acknowledge there is a limit to productivity in a scaling business, and choose the best two-out-of-three path.

Sean Bloomfield
3 years ago
How Jeff Bezos wins meetings over
We've all been there: You propose a suggestion to your team at a meeting, and most people appear on board, but a handful or small minority aren't. How can we achieve collective buy-in when we need to go forward but don't know how to deal with some team members' perceived intransigence?
Steps:
Investigate the divergent opinions: Begin by sincerely attempting to comprehend the viewpoint of your disagreeing coworkers. Maybe it makes sense to switch horses in the middle of the race. Have you completely overlooked a blind spot, such as a political concern that could arise as an unexpected result of proceeding? This is crucial to ensure that the person or people feel heard as well as to advance the goals of the team. Sometimes all individuals need is a little affirmation before they fully accept your point of view.
It says a lot about you as a leader to be someone who always lets the perceived greatest idea win, regardless of the originating channel, if after studying and evaluating you see the necessity to align with the divergent position.
If, after investigation and assessment, you determine that you must adhere to the original strategy, we go to Step 2.
2. Disagree and Commit: Jeff Bezos, CEO of Amazon, has had this experience, and Julie Zhuo describes how he handles it in her book The Making of a Manager.
It's OK to disagree when the team is moving in the right direction, but it's not OK to accidentally or purposefully damage the team's efforts because you disagree. Let the team know your opinion, but then help them achieve company goals even if they disagree. Unknown. You could be wrong in today's ever-changing environment.
So next time you have a team member who seems to be dissenting and you've tried the previous tactics, you may ask the individual in the meeting I understand you but I don't want us to leave without you on board I need your permission to commit to this approach would you give us your commitment?
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Henrique Centieiro
3 years ago
DAO 101: Everything you need to know
Maybe you'll work for a DAO next! Over $1 Billion in NFTs in the Flamingo DAO Another DAO tried to buy the NFL team Denver Broncos. The UkraineDAO raised over $7 Million for Ukraine. The PleasrDAO paid $4m for a Wu-Tang Clan album that belonged to the “pharma bro.”
DAOs move billions and employ thousands. So learn what a DAO is, how it works, and how to create one!
DAO? So, what? Why is it better?
A Decentralized Autonomous Organization (DAO). Some people like to also refer to it as Digital Autonomous Organization, but I prefer the former.
They are virtual organizations. In the real world, you have organizations or companies right? These firms have shareholders and a board. Usually, anyone with authority makes decisions. It could be the CEO, the Board, or the HIPPO. If you own stock in that company, you may also be able to influence decisions. It's now possible to do something similar but much better and more equitable in the cryptocurrency world.
This article informs you:
DAOs- What are the most common DAOs, their advantages and disadvantages over traditional companies? What are they if any?
Is a DAO legally recognized?
How secure is a DAO?
I’m ready whenever you are!
A DAO is a type of company that is operated by smart contracts on the blockchain. Smart contracts are computer code that self-executes our commands. Those contracts can be any. Most second-generation blockchains support smart contracts. Examples are Ethereum, Solana, Polygon, Binance Smart Chain, EOS, etc. I think I've gone off topic. Back on track. Now let's go!
Unlike traditional corporations, DAOs are governed by smart contracts. Unlike traditional company governance, DAO governance is fully transparent and auditable. That's one of the things that sets it apart. The clarity!
A DAO, like a traditional company, has one major difference. In other words, it is decentralized. DAOs are more ‘democratic' than traditional companies because anyone can vote on decisions. Anyone! In a DAO, we (you and I) make the decisions, not the top-shots. We are the CEO and investors. A DAO gives its community members power. We get to decide.
As long as you are a stakeholder, i.e. own a portion of the DAO tokens, you can participate in the DAO. Tokens are open to all. It's just a matter of exchanging it. Ownership of DAO tokens entitles you to exclusive benefits such as governance, voting, and so on. You can vote for a move, a plan, or the DAO's next investment. You can even pitch for funding. Any ‘big' decision in a DAO requires a vote from all stakeholders. In this case, ‘token-holders'! In other words, they function like stock.
What are the 5 DAO types?
Different DAOs exist. We will categorize decentralized autonomous organizations based on their mode of operation, structure, and even technology. Here are a few. You've probably heard of them:
1. DeFi DAO
These DAOs offer DeFi (decentralized financial) services via smart contract protocols. They use tokens to vote protocol and financial changes. Uniswap, Aave, Maker DAO, and Olympus DAO are some examples. Most DAOs manage billions.
Maker DAO was one of the first protocols ever created. It is a decentralized organization on the Ethereum blockchain that allows cryptocurrency lending and borrowing without a middleman.
Maker DAO issues DAI, a stable coin. DAI is a top-rated USD-pegged stable coin.
Maker DAO has an MKR token. These token holders are in charge of adjusting the Dai stable coin policy. Simply put, MKR tokens represent DAO “shares”.
2. Investment DAO
Investors pool their funds and make investment decisions. Investing in new businesses or art is one example. Investment DAOs help DeFi operations pool capital. The Meta Cartel DAO is a community of people who want to invest in new projects built on the Ethereum blockchain. Instead of investing one by one, they want to pool their resources and share ideas on how to make better financial decisions.
Other investment DAOs include the LAO and Friends with Benefits.
3. DAO Grant/Launchpad
In a grant DAO, community members contribute funds to a grant pool and vote on how to allocate and distribute them. These DAOs fund new DeFi projects. Those in need only need to apply. The Moloch DAO is a great Grant DAO. The tokens are used to allocate capital. Also see Gitcoin and Seedify.
4. DAO Collector
I debated whether to put it under ‘Investment DAO' or leave it alone. It's a subset of investment DAOs. This group buys non-fungible tokens, artwork, and collectibles. The market for NFTs has recently exploded, and it's time to investigate. The Pleasr DAO is a collector DAO. One copy of Wu-Tang Clan's "Once Upon a Time in Shaolin" cost the Pleasr DAO $4 million. Pleasr DAO is known for buying Doge meme NFT. Collector DAOs include the Flamingo, Mutant Cats DAO, and Constitution DAOs. Don't underestimate their websites' "childish" style. They have millions.
5. Social DAO
These are social networking and interaction platforms. For example, Decentraland DAO and Friends With Benefits DAO.
What are the DAO Benefits?
Here are some of the benefits of a decentralized autonomous organization:
- They are trustless. You don’t need to trust a CEO or management team
- It can’t be shut down unless a majority of the token holders agree. The government can't shut - It down because it isn't centralized.
- It's fully democratic
- It is open-source and fully transparent.
What about DAO drawbacks?
We've been saying DAOs are the bomb? But are they really the shit? What could go wrong with DAO?
DAOs may contain bugs. If they are hacked, the results can be catastrophic.
No trade secrets exist. Because the smart contract is transparent and coded on the blockchain, it can be copied. It may be used by another organization without credit. Maybe DAOs should use Secret, Oasis, or Horizen blockchain networks.
Are DAOs legally recognized??
In most counties, DAO regulation is inexistent. It's unclear. Most DAOs don’t have a legal personality. The Howey Test and the Securities Act of 1933 determine whether DAO tokens are securities. Although most countries follow the US, this is only considered for the US. Wyoming became the first state to recognize DAOs as legal entities in July 2021 after passing a DAO bill. DAOs registered in Wyoming are thus legally recognized as business entities in the US and thus receive the same legal protections as a Limited Liability Company.
In terms of cyber-security, how secure is a DAO?
Blockchains are secure. However, smart contracts may have security flaws or bugs. This can be avoided by third-party smart contract reviews, testing, and auditing
Finally, Decentralized Autonomous Organizations are timeless. Let us examine the current situation: Ukraine's invasion. A DAO was formed to help Ukrainian troops fighting the Russians. It was named Ukraine DAO. Pleasr DAO, NFT studio Trippy Labs, and Russian art collective Pussy Riot organized this fundraiser. Coindesk reports that over $3 million has been raised in Ethereum-based tokens. AidForUkraine, a DAO aimed at supporting Ukraine's defense efforts, has launched. Accepting Solana token donations. They are fully transparent, uncensorable, and can’t be shut down or sanctioned.
DAOs are undeniably the future of blockchain. Everyone is paying attention. Personally, I believe traditional companies will soon have to choose between adapting or being left behind.
Long version of this post: https://medium.datadriveninvestor.com/dao-101-all-you-need-to-know-about-daos-275060016663

Rachel Greenberg
3 years ago
The Unsettling Fact VC-Backed Entrepreneurs Don't Want You to Know
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.

Bastian Hasslinger
3 years ago
Before 2021, most startups had excessive valuations. It is currently causing issues.
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:
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.
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.
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.
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.
