5 VC investment criteria

I reviewed 200 startup business concepts last week. Brainache.

The enterprises sold various goods and services. The concepts were achingly similar: give us money, we'll produce a product, then get more to expand. No different from daily plans and pitches.

Most of those 200 plans sounded plausible. But 10% looked venture-worthy. 90% of startups need alternatives to venture finance.

With the success of VC-backed businesses and the growth of venture funds, a common misperception is that investors would fund any decent company idea. Finding investors that believe in the firm and founders is the key to funding.

Incorrect. Venture capital needs investing in certain enterprises. If your startup doesn't match the model, as most early-stage startups don't, you can revise your business plan or locate another source of capital.

Before spending six months pitching angels and VCs, make sure your startup fits these criteria.

Likely to generate $100 million in sales

First, I check the income predictions in a pitch deck. If it doesn't display $100M, don't bother.

The math doesn't work for venture financing in smaller businesses.

Say a fund invests $1 million in a startup valued at $5 million that is later acquired for $20 million. That's a win everyone should celebrate. Most VCs don't care.

Consider a $100M fund. The fund must reach $360M in 7 years with a 20% return. Only 20-30 investments are possible. 90% of the investments will fail, hence the 23 winners must return $100M-$200M apiece. $15M isn't worth the work.

Angel investors and tiny funds use the same ideas as venture funds, but their smaller scale affects the calculations. If a company can support its growth through exit on less than $2M in angel financing, it must have $25M in revenues before large companies will consider acquiring it.

Aiming for Hypergrowth

A startup's size isn't enough. It must expand fast.

Developing a great business takes time. Complex technology must be constructed and tested, a nationwide expansion must be built, or production procedures must go from lab to pilot to factories. These can be enormous, world-changing corporations, but venture investment is difficult.

The normal 10-year venture fund life. Investments are made during first 3–4 years.. 610 years pass between investment and fund dissolution. Funds need their investments to exit within 5 years, 7 at the most, therefore add a safety margin.

Longer exit times reduce ROI. A 2-fold return in a year is excellent. Loss at 2x in 7 years.

Lastly, VCs must prove success to raise their next capital. The 2nd fund is raised from 1st fund portfolio increases. Third fund is raised using 1st fund's cash return. Fund managers must raise new money quickly to keep their jobs.

Branding or technology that is protected

No big firm will buy a startup at a high price if they can produce a competing product for less. Their development teams, consumer base, and sales and marketing channels are large. Who needs you?

Patents, specialist knowledge, or brand name are the only answers. The acquirer buys this, not the thing.

I've heard of several promising startups. It's not a decent investment if there's no exit strategy.

A company that installs EV charging stations in apartments and shopping areas is an example. It's profitable, repeatable, and big. A terrific company. Not a startup.

This building company's operations aren't secret. No technology to protect, no special information competitors can't figure out, no go-to brand name. Despite the immense possibilities, a large construction company would be better off starting their own.

Most venture businesses build products, not services. Services can be profitable but hard to safeguard.

Probable purchase at high multiple

Once a software business proves its value, acquiring it is easy. Pharma and medtech firms have given up on their own research and instead acquire startups after regulatory permission. Many startups, especially in specialized areas, have this weakness.

That doesn't mean any lucrative $25M-plus business won't be acquired. In many businesses, the venture model requires a high exit premium.

A startup invents a new glue. 3M, BASF, Henkel, and others may buy them. Adding more adhesive to their catalogs won't boost commerce. They won't compete to buy the business. They'll only buy a startup at a profitable price. The acquisition price represents a moderate EBITDA multiple.

The company's $100M revenue presumably yields $10m in profits (assuming they’ve reached profitability at all). A $30M-$50M transaction is likely. Not terrible, but not what venture investors want after investing $25M to create a plant and develop the business.

Private equity buys profitable companies for a moderate profit multiple. It's a good exit for entrepreneurs, but not for investors seeking 10x or more what PE firms pay. If a startup offers private equity as an exit, the conversation is over.

Constructed for purchase

The startup wants a high-multiple exit. Unless the company targets $1B in revenue and does an IPO, exit means acquisition.

If they're constructing the business for acquisition or themselves, founders must decide.

If you want an indefinitely-running business, I applaud you. We need more long-term founders. Most successful organizations are founded around consumer demands, not venture capital's urge to grow fast and exit. Not venture funding.

if you don't match the venture model, what to do

VC funds moonshots. The 10% that succeed are extraordinary. Not every firm is a rocketship, and launching the wrong startup into space, even with money, will explode.

But just because your startup won't make $100M in 5 years doesn't mean it's a bad business. Most successful companies don't follow this model. It's not venture capital-friendly.

Although venture capital gets the most attention due to a few spectacular triumphs (and disasters), it's not the only or even most typical option to fund a firm.

Other ways to support your startup:

• Personal and family resources, such as credit cards, second mortgages, and lines of credit

• bootstrapping off of sales

• government funding and honors

• Private equity & project financing

• collaborating with a big business

• Including a business partner

Before pitching angels and VCs, be sure your startup qualifies. If so, include them in your pitch.

Or the “lie to me” method.

I can predict a startup's success in minutes.

Just interview its founder.

Ask "why?"

I question "why" till I sense him.

I need to feel the person I have in front of me. I need to know if he or she can deliver. Startups aren't easy. Without abilities, a brilliant idea will fail.

Good entrepreneurs have these qualities: He's a leader, determined, and resilient.

For me, they can be split in two categories.

The first entrepreneur aspires to live meaningfully. The second wants to get rich. The second is communicative. He wants to wow the crowd. He's motivated by the thought of one day sailing a boat past palm trees and sunny beaches.

What drives the first entrepreneur is evident in his speech, face, and voice. He will not speak about his product. He's (nearly) uninterested. He's not selling anything. He's not a salesman. He wants to succeed. The product is his fuel.

He'll explain his decision. He'll share his motivations. His desire. And he'll use meaningful words.

Paul Ekman has shown that face expressions aren't cultural. His study influenced the American TV series "lie to me" about body language and speech.

Passionate entrepreneurs are obvious. It's palpable. Faking passion is tough. Someone who wants your favor and money will expose his actual motives through his expressions and language.

The good liar will be able to fool you for a while, but not for long if you pay attention to his body language and how he expresses himself.

And also, if you look at his business plan.

His business plan reveals his goals. Read between the lines.

Entrepreneur 1 will focus on his "why", whereas Entrepreneur 2 will focus on the "how".

Entrepreneur 1 will develop a vision-driven culture.

The second, on the other hand, will focus on his EBITDA.

Why is the culture so critical? Because it will allow entrepreneur 1 to develop a solid team that can tackle his problems and trials. His team's "why" will keep them together in tough times.

"Give me a terrific start-up team with a mediocre idea over a weak one any day." Because a great team knows when to pivot and trusts each other. Weak teams fail.” — Bernhard Schroeder

Closings thoughts

Every VC must ask Why. Entrepreneur's motivations. This "why" will create the team's culture. This culture will help the team adjust to any setback.

During the dot-com bust, I started my internet career. People used the internet intermittently to check email, plan travel, and do research. The average internet user spent 30 minutes online a day, compared to 7 today. To use the internet, you had to "log on" (most people still used dial-up), unlike today's always-on, high-speed mobile internet. In 2001, Amazon's market cap was $2.2B, 1/500th of what it is today. A study asked Americans if they'd adopt broadband, and most said no. They didn't see a need to speed up email, the most popular internet use. The National Academy of Sciences ranked the internet 13th among the 100 greatest inventions, below radio and phones. The internet was a cool invention, but it had limited uses and wasn't a good place to build a business. 

A small but growing movement of developers and founders believed the internet could be more than a read-only medium, allowing anyone to create and publish. This is web 2. The runner up name was read-write web. (These terms were used in prominent publications and conferences.) 

Web 2 concepts included letting users publish whatever they want ("user generated content" was a buzzword), social graphs, APIs and mashups (what we call composability today), and tagging over hierarchical navigation. Technical innovations occurred. A seemingly simple but important one was dynamically updating web pages without reloading. This is now how people expect web apps to work. Mobile devices that could access the web were niche (I was an avid Sidekick user). 

The contrast between what smart founders and engineers discussed over dinner and on weekends and what the mainstream tech world took seriously during the week was striking. Enterprise security appliances, essentially preloaded servers with security software, were a popular trend. Many of the same people would talk about "serious" products at work, then talk about consumer internet products and web 2. It was tech's biggest news. Web 2 products were seen as toys, not real businesses. They were hobbies, not work-related. 

There's a strong correlation between rich product design spaces and what smart people find interesting, which took me some time to learn and led to blog posts like "The next big thing will start out looking like a toy" Web 2's novel product design possibilities sparked dinner and weekend conversations. Imagine combining these features. What if you used this pattern elsewhere? What new product ideas are next? This excited people. "Serious stuff" like security appliances seemed more limited. 

The small and passionate web 2 community also stood out. I attended the first New York Tech meetup in 2004. Everyone fit in Meetup's small conference room. Late at night, people demoed their software and chatted. I have old friends. Sometimes I get asked how I first met old friends like Fred Wilson and Alexis Ohanian. These topics didn't interest many people, especially on the east coast. We were friends. Real community. Alex Rampell, who now works with me at a16z, is someone I met in 2003 when a friend said, "Hey, I met someone else interested in consumer internet." Rare. People were focused and enthusiastic. Revolution seemed imminent. We knew a secret nobody else did. 

My web 2 startup was called SiteAdvisor. When my co-founders and I started developing the idea in 2003, web security was out of control. Phishing and spyware were common on Internet Explorer PCs. SiteAdvisor was designed to warn users about security threats like phishing and spyware, and then, using web 2 concepts like user-generated reviews, add more subjective judgments (similar to what TrustPilot seems to do today). This staged approach was common at the time; I called it "Come for the tool, stay for the network." We built APIs, encouraged mashups, and did SEO marketing. 

Yahoo's 2005 acquisitions of Flickr and Delicious boosted web 2 in 2005. By today's standards, the amounts were small, around $30M each, but it was a signal. Web 2 was assumed to be a fun hobby, a way to build cool stuff, but not a business. Yahoo was a savvy company that said it would make web 2 a priority. 

As I recall, that's when web 2 started becoming mainstream tech. Early web 2 founders transitioned successfully. Other entrepreneurs built on the early enthusiasts' work. Competition shifted from ideation to execution. You had to decide if you wanted to be an idealistic indie bar band or a pragmatic stadium band. 

Web 2 was booming in 2007 Facebook passed 10M users, Twitter grew and got VC funding, and Google bought YouTube. The 2008 financial crisis tested entrepreneurs' resolve. Smart people predicted another great depression as tech funding dried up. 

Many people struggled during the recession. 2008-2011 was a golden age for startups. By 2009, talented founders were flooding Apple's iPhone app store. Mobile apps were booming. Uber, Venmo, Snap, and Instagram were all founded between 2009 and 2011. Social media (which had replaced web 2), cloud computing (which enabled apps to scale server side), and smartphones converged. Even if social, cloud, and mobile improve linearly, the combination could improve exponentially. 

This chart shows how I view product and financial cycles. Product and financial cycles evolve separately. The Nasdaq index is a proxy for the financial sentiment. Financial sentiment wildly fluctuates. 

Next row shows iconic startup or product years. Bottom-row product cycles dictate timing. Product cycles are more predictable than financial cycles because they follow internal logic. In the incubation phase, enthusiasts build products for other enthusiasts on nights and weekends. When the right mix of technology, talent, and community knowledge arrives, products go mainstream. (I show the biggest tech cycles in the chart, but smaller ones happen, like web 2 in the 2000s and fintech and SaaS in the 2010s.) 

Tech has changed since the 2000s. Few tech giants dominate the internet, exerting economic and cultural influence. In the 2000s, web 2 was ignored or dismissed as trivial. Entrenched interests respond aggressively to new movements that could threaten them. Creative patterns from the 2000s continue today, driven by enthusiasts who see possibilities where others don't. Know where to look. Crypto and web 3 are where I'd start. 

Today's negative financial sentiment reminds me of 2008. If we face a prolonged downturn, we can learn from 2008 by preserving capital and focusing on the long term. Keep an eye on the product cycle. Smart people are interested in things with product potential. This becomes true. Toys become necessities. Hobbies become mainstream. Optimists build the future, not cynics.

Full article is available here

Technical books aren't like novels. We need a new approach to technical texts. I've spent years looking for a decent reading method. I tried numerous ways before finding one that worked. This post explains how I read technical books efficiently.

What Do I Mean When I Say Effective?

Effectiveness depends on the book. Effective implies I know where to find answers after reading a reference book. Effective implies I learned the book's knowledge after reading it.

I use reference books as tools in my toolkit. I won't carry all my tools; I'll merely need them. Non-reference books teach me techniques. I never have to make an effort to use them since I always have them.

Reference books I like:

• Design Patterns: Elements of Reusable Object-Oriented Software

• Refactoring: Improving the Design of Existing Code 
  You can also check My Top Takeaways from Refactoring here.

• Practical Object-Oriented Design in Ruby: An Agile Primer

Non-reference books I like:

• The Pragmatic Programmer: your journey to mastery

• Clean Code: A Handbook of Agile Software Craftsmans

The Approach

Technical books might be overwhelming to read in one sitting. Especially when you have no idea what is coming next as you read. When you don't know how deep the rabbit hole goes, you feel lost as you read. This is my years-long method for overcoming this difficulty.

Whether you follow the step-by-step guide or not, remember these:

• Understand the terminology. Make sure you get the meaning of any terms you come across more than once. The likelihood that a term will be significant increases as you encounter it more frequently.

• Know when to stop. I've always believed that in order to truly comprehend something, I must delve as deeply as possible into it. That, however, is not usually very effective. There are moments when you have to draw the line and start putting theory into practice (if applicable).

• Look over your notes. When reading technical books or documents, taking notes is a crucial habit to develop. Additionally, you must regularly examine your notes if you want to get the most out of them. This will assist you in internalizing the lessons you acquired from the book. And you'll see that the urge to review reduces with time.

Let's talk about how I read a technical book step by step.

0. Read the Foreword/Preface

These sections are crucial in technical books. They answer Who should read it, What each chapter discusses, and sometimes How to Read? This is helpful before reading the book. Who could know the ideal way to read the book better than the author, right?

1. Scanning

I scan the chapter. Fast scanning is needed.

• I review the headings.

• I scan the pictures quickly.

• I assess the chapter's length to determine whether I might divide it into more manageable sections.

2. Skimming

Skimming is faster than reading but slower than scanning.

• I focus more on the captions and subtitles for the photographs.

• I read each paragraph's opening and closing sentences.

• I examined the code samples.

• I attempt to grasp each section's basic points without getting bogged down in the specifics.

• Throughout the entire reading period, I make an effort to make mental notes of what may require additional attention and what may not. Because I don't want to spend time taking physical notes, kindly notice that I am using the term "mental" here. It is much simpler to recall. You may think that this is more significant than typing or writing “Pay attention to X.”

• I move on quickly. This is something I considered crucial because, when trying to skim, it is simple to start reading the entire thing.

3. Complete reading

Previous steps pay off.

• I finished reading the chapter.

• I concentrate on the passages that I mentally underlined when skimming.

• I put the book away and make my own notes. It is typically more difficult than it seems for me. But it's important to speak in your own words. You must choose the right words to adequately summarize what you have read. How do those words make you feel? Additionally, you must be able to summarize your notes while you are taking them. Sometimes as I'm writing my notes, I realize I have no words to convey what I'm thinking or, even worse, I start to doubt what I'm writing down. This is a good indication that I haven't internalized that idea thoroughly enough.

• I jot my inquiries down. Normally, I read on while compiling my questions in the hopes that I will learn the answers as I read. I'll explore those issues more if I wasn't able to find the answers to my inquiries while reading the book.

Bonus!

Best part: If you take lovely notes like I do, you can publish them as a blog post with a few tweaks.

Conclusion

This is my learning journey. I wanted to show you. This post may help someone with a similar learning style. You can alter the principles above for any technical material.

Security, privacy, and a strategy!

How to manage digital assets in worst-case scenarios is a perennial crypto concern. Since blockchain and bitcoin technology is very new, this hasn't been a major issue. Many early developers are still around, and many groups created around this technology are young and feel they have a lot of life remaining. This is why inheritance and estate planning in crypto should be handled promptly. As cryptocurrency's intrinsic worth rises, many people in the ecosystem are holding on to assets that might represent generational riches. With that much value, it's crucial to have a plan. Creating a solid plan entails several challenges.

• the initial hesitation in coming up with a plan

• The technical obstacles to ensuring the assets' security and privacy

• the passing of assets from a deceased or incompetent person

• Legal experts' lack of comprehension and/or understanding of how to handle and treat cryptocurrency.

This article highlights several challenges, a possible web3-native solution, and how to learn more.

The Challenge of Inheritance:

One of the biggest hurdles to inheritance planning is starting the conversation. As humans, we don't like to think about dying. Early adopters will experience crazy gains as cryptocurrencies become more popular. Creating a plan is crucial if you wish to pass on your riches to loved ones. Without a plan, the technical and legal issues I barely mentioned above would erode value by requiring costly legal fees and/or taxes, and you could lose everything if wallets and assets are not distributed appropriately (associated with the private keys). Raising awareness of the consequences of not having a plan should motivate people to make one.

Controlling Change:

Having an inheritance plan for your digital assets is crucial, but managing the guts and bolts poses a new set of difficulties. Privacy and security provided by maintaining your own wallet provide different issues than traditional finances and assets. Traditional finance is centralized (say a stock brokerage firm). You can assign another person to handle the transfer of your assets. In crypto, asset transfer is reimagined. One may suppose future transaction management is doable, but the user must consent, creating an impossible loop.

• I passed away and must send a transaction to the person I intended to deliver it to.

• I have to confirm or authorize the transaction, but I'm dead.

In crypto, scheduling a future transaction wouldn't function. To transfer the wallet and its contents, we'd need the private keys and/or seed phrase. Minimizing private key exposure is crucial to protecting your crypto from hackers, social engineering, and phishing. People have lost private keys after utilizing Life Hack-type tactics to secure them. People that break and hide their keys, lose them, or make them unreadable won't help with managing and/or transferring. This will require a derived solution.

Legal Challenges and Implications

Unlike routine cryptocurrency transfers and transactions, local laws may require special considerations. Even in the traditional world, estate/inheritance taxes, how assets will be split, and who executes the will must be considered. Many lawyers aren't crypto-savvy, which complicates the matter. There will be many hoops to jump through to safeguard your crypto and traditional assets and give them to loved ones.

Knowing RUFADAA/UFADAA, depending on your state, is vital for Americans. UFADAA offers executors and trustees access to online accounts (which crypto wallets would fall into). RUFADAA was changed to limit access to the executor to protect assets. RUFADAA outlines how digital assets are administered following death and incapacity in the US.

A Succession Solution

Having a will and talking about who would get what is the first step to having a solution, but using a Dad Mans Switch is a perfect tool for such unforeseen circumstances. As long as the switch's controller has control, nothing happens. Losing control of the switch initiates a state transition.

Subway or railway operations are examples. Modern control systems need the conductor to hold a switch to keep the train going. If they can't, the train stops.

Enter Sarcophagus

Sarcophagus is a decentralized dead man's switch built on Ethereum and Arweave. Sarcophagus allows actors to maintain control of their possessions even while physically unable to do so. Using a programmable dead man's switch and dual encryption, anything can be kept and passed on. This covers assets, secrets, seed phrases, and other use cases to provide authority and control back to the user and release trustworthy services from this work. Sarcophagus is built on a decentralized, transparent open source codebase. Sarcophagus is there if you're unprepared.

Taking great financial advice is key to financial success.

A wealthy man told me to INVEST MY MONEY when I was young.

As I entered Starbucks, an older man was leaving. I noticed his watch and expensive-looking shirt, not like the guy in the photo, but one made of fine fabric like vicuna wool, which can only be shorn every two to three years. His Bentley confirmed my suspicions about his wealth.

This guy looked like James Bond, so I asked him how to get rich like him.

"Drug dealer?" he laughed.

Whether he was telling the truth, I'll never know, and I didn't want to be an accessory, but he quickly added, "Kid, invest your money; it will do wonders." He left.

When he told me to invest, he didn't say what. Later, I realized the investment game has so many levels that even if he drew me a blueprint, I wouldn't understand it.

The best advice I received was to invest my earnings. I must decide where to invest.

I'll preface by saying I'm not a financial advisor or Your financial advisor, but I'll share what I've learned from books, links, and sources. The rest is up to you.

Basically:

Invest your Money

Money is money, whether you call it cake, dough, moolah, benjamins, paper, bread, etc.

If you're lucky, you can buy one of the gold shirts in the photo.

Investing your money today means putting it towards anything that could be profitable.

According to the website Investopedia:
“Investing is allocating money to generate income or profit.”

You can invest in a business, real estate, or a skill that will pay off later.

Everyone has different goals and wants at different stages of life, so investing varies.

He was probably a sugar daddy with his Bentley, nice shirt, and Rolex.

In my twenties, I started making "good" money; now, in my forties, with a family and three kids, I'm building a legacy for my grandkids.

“It’s not how much money you make, but how much money you keep, how hard it works for you, and how many generations you keep it for.” — Robert Kiyosaki.

Money isn't evil, but lack of it is.

Financial stress is a major source of problems, according to studies. 

Being broke hurts, especially if you want to provide for your family or do things.

“An investment in knowledge pays the best interest.” — Benjamin Franklin.

Investing in knowledge is invaluable. Before investing, do your homework.

You probably didn't learn about investing when you were young, like I didn't. My parents were in survival mode, making investing difficult.

In my 20s, I worked in banking to better understand money.

So, why invest?

Growth requires investment.

Investing puts money to work and can build wealth. Your money may outpace inflation with smart investing. Compounding and the risk-return tradeoff boost investment growth.

Investing your money means you won't have to work forever — unless you want to.

Two common ways to make money are;

-working hard,

and

-interest or capital gains from investments.

Capital gains can help you invest.

“How many millionaires do you know who have become wealthy by investing in savings accounts? I rest my case.” — Robert G. Allen

If you keep your money in a savings account, you'll earn less than 2% interest at best; the bank makes money by loaning it out.

Savings accounts are a safe bet, but the low-interest rates limit your gains.

Don't skip it. An emergency fund should be in a savings account, not the market.

Other reasons to invest:

Investing can generate regular income.

If you own rental properties, the tenant's rent will add to your cash flow.

Daily, weekly, or monthly rentals (think Airbnb) generate higher returns year-round.

Capital gains are taxed less than earned income if you own dividend-paying or appreciating stock.

Time is on your side

“Compound interest is the eighth wonder of the world. He who understands it, earns it; he who doesn’t — pays it.” — Albert Einstein

Historical data shows that young investors outperform older investors. So you can use compound interest over decades instead of investing at 45 and having less time to earn.

If I had taken that man's advice and invested in my twenties, I would have made a decent return by my thirties. (Depending on my investments)

So for those who live a YOLO (you only live once) life, investing can't hurt.

Investing increases your knowledge.

Lessons are clearer when you're invested. Each win boosts confidence and draws attention to losses. Losing money prompts you to investigate.

Before investing, I read many financial books, but I didn't understand them until I invested.

Now what?

What do you invest in? Equities, mutual funds, ETFs, retirement accounts, savings, business, real estate, cryptocurrencies, marijuana, insurance, etc.

The key is to start somewhere. Know you don't know everything. You must care.

“A journey of a thousand miles must begin with a single step.” — Lao Tzu.

Start simple because there's so much information. My first investment book was:

Robert Kiyosaki's "Rich Dad, Poor Dad"

This easy-to-read book made me hungry for more. This book is about the money lessons rich parents teach their children, which poor and middle-class parents neglect. The poor and middle-class work for money, while the rich let their assets work for them, says Kiyosaki.

There is so much to learn, but you gotta start somewhere.

More books:

***Wisdom

I hope I'm not suggesting that investing makes everything rosy. Remember three rules:

1. Losing money is possible.

2. Losing money is possible.

3. Losing money is possible.

You can lose money, so be careful.

Read, research, invest.

Golden rules for Investing your money

• Never invest money you can't lose.

• Financial freedom is possible regardless of income.

• "Courage taught me that any sound investment will pay off, no matter how bad a crisis gets." Helu Carlos

• "I'll tell you Wall Street's secret to wealth. When others are afraid, you're greedy. You're afraid when others are greedy. Buffett

• Buy low, sell high, and have an exit strategy.

• Ask experts or wealthy people for advice.

• "With a good understanding of history, we can have a clear vision of the future." Helu Carlos

• "It's not whether you're right or wrong, but how much money you make when you're right." Soros

• "The individual investor should act as an investor, not a speculator." Graham

• "It's different this time" is the most dangerous investment phrase. Templeton

Lastly,

• Avoid quick-money schemes. Building wealth takes years, not months.

Start small and work your way up.

Thanks for reading!

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