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.

I've written a lot about Y Combinator's success, but as any startup founder or investor knows, many startups fail.

Rebel Fund invests in the top 5-10% of new Y Combinator startups each year, so we focus on identifying and supporting the most promising technology startups in our ecosystem. Given the power law dynamic and asymmetric risk/return profile of venture capital, we worry more about our successes than our failures. Since the latter still counts, this essay will focus on the proportion of YC startups that fail.

Since YC's launch in 2005, the figure below shows the percentage of active, inactive, and public/acquired YC startups by batch.

As more startups finish, the blue bars (active) decrease significantly. By 12 years, 88% of startups have closed or exited. Only 7% of startups reach resolution each year.

YC startups by status after 12 years:

Half the startups have failed, over one-third have exited, and the rest are still operating.

In venture investing, it's said that failed investments show up before successful ones. This is true for YC startups, but only in their early years.

Below, we only present resolved companies from the first chart. Some companies fail soon after establishment, but after a few years, the inactive vs. public/acquired ratio stabilizes around 55:45. After a few years, a YC firm is roughly as likely to quit as fail, which is better than I imagined.

I prepared this post because Rebel investors regularly question me about YC startup failure rates and how long it takes for them to exit or shut down.

Early-stage venture investors can overlook it because 100x investments matter more than 0x investments.

YC founders can ignore it because it shouldn't matter if many of their peers succeed or fail ;)

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.

Let's see this once-dominant IT corporation crumble.

What's the capital of Kazakhstan? If you don't know the answer, you can probably find it by Googling. Google Search returned results for Nur-Sultan in 0.66 seconds.

Google is the best search engine I've ever used. Did you know another search engine ruled the Internet? I'm sure you guessed Yahoo!

Google's friendly UI and wide selection of services make it my top choice. Let's explore Yahoo's decline.

Yahoo!

YAHOO stands for Yet Another Hierarchically Organized Oracle. Jerry Yang and David Filo established Yahoo.

Yahoo is primarily a search engine and email provider. It offers News and an advertising platform. It was a popular website in 1995 that let people search the Internet directly. Yahoo began offering free email in 1997 by acquiring RocketMail.

According to a study, Yahoo used Google Search Engine technology until 2000 and then developed its own in 2004.

Yahoo! rejected buying Google for $1 billion

Larry Page and Sergey Brin, Google's founders, approached Yahoo in 1998 to sell Google for $1 billion so they could focus on their studies. Yahoo denied the offer, thinking it was overvalued at the time.

Yahoo realized its error and offered Google $3 billion in 2002, but Google demanded $5 billion since it was more valuable. Yahoo thought $5 billion was overpriced for the existing market.

In 2022, Google is worth $1.56 Trillion.

What happened to Yahoo!

Yahoo refused to buy Google, and Google's valuation rose, making a purchase unfeasible.

Yahoo started losing users when Google launched Gmail. Google's UI was far cleaner than Yahoo's.

Yahoo offered $1 billion to buy Facebook in July 2006, but Zuckerberg and the board sought $1.1 billion. Yahoo rejected, and Facebook's valuation rose, making it difficult to buy.

Yahoo was losing users daily while Google and Facebook gained many. Google and Facebook's popularity soared. Yahoo lost value daily.

Microsoft offered $45 billion to buy Yahoo in February 2008, but Yahoo declined. Microsoft increased its bid to $47 billion after Yahoo said it was too low, but Yahoo rejected it. Then Microsoft rejected Yahoo’s 10% bid increase in May 2008.

In 2015, Verizon bought Yahoo for $4.5 billion, and Apollo Global Management bought 90% of Yahoo's shares for $5 billion in May 2021. Verizon kept 10%.

Yahoo's opportunity to acquire Google and Facebook could have been a turning moment. It declined Microsoft's $45 billion deal in 2008 and was sold to Verizon for $4.5 billion in 2015. Poor decisions and lack of vision caused its downfall. Yahoo's aim wasn't obvious and it didn't stick to a single domain.

Hence, a corporation needs a clear vision and a leader who can see its future.

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No other calendar is simpler, smaller, and reusable year after year. It works and is used here.

Most of us discard and replace our calendars annually. Each month, we move our calendar ahead another page, thus if we need to know which day of the week corresponds to a given day/month combination, we have to calculate it or flip forward/backward to the corresponding month. Questions like:

• What day does this year's American Thanksgiving fall on?

• Which months contain a Friday the thirteenth?

• When is July 4th? What day of the week?

• Alternatively, what day of the week is Christmas?

They're hard to figure out until you switch to the right month or look up all the months.

However, mathematically, the answers to these questions or any question that requires matching the day of the week with the day/month combination in a year are predictable, basic, and easy to work out. If you use this one-page calendar instead of a 12-month calendar, it lasts the whole year and is easy to alter for future years. Let me explain.

The 2023 one-page calendar is above. The days of the month are on the lower left, which works for all months if you know that:

• There are 31 days in January, March, May, July, August, October, and December.

• All of the months of April, June, September, and November have 30 days.

• And depending on the year, February has either 28 days (in non-leap years) or 29 days (in leap years).

If you know this, this calendar makes it easy to match the day/month of the year to the weekday.

Here are some instances. American Thanksgiving is always on the fourth Thursday of November. You'll always know the month and day of the week, but the date—the day in November—changes each year.

On any other calendar, you'd have to flip to November to see when the fourth Thursday is. This one-page calendar only requires:

• pick the month of November in the top-right corner to begin.

• drag your finger down until Thursday appears,

• then turn left and follow the monthly calendar until you reach the fourth Thursday.

It's obvious: 2023 is the 23rd American Thanksgiving. For every month and day-of-the-week combination, start at the month, drag your finger down to the desired day, and then move to the left to see which dates match.

What if you knew the day of the week and the date of the month, but not the month(s)?

A different method using the same one-page calendar gives the answer. Which months have Friday the 13th this year? Just:

• begin on the 13th of the month, the day you know you desire,

• then swipe right with your finger till Friday appears.

• and then work your way up until you can determine which months the specific Friday the 13th falls under.

One Friday the 13th occurred in January 2023, and another will occur in October.

The most typical reason to consult a calendar is when you know the month/day combination but not the day of the week.

Compared to single-month calendars, the one-page calendar excels here. Take July 4th, for instance. Find the weekday here:

• beginning on the left on the fourth of the month, as you are aware,

• also begin with July, the month of the year you are most familiar with, at the upper right,

• you should move your two fingers in the opposite directions till they meet: on a Tuesday in 2023.

That's how you find your selected day/month combination's weekday.

Another example: Christmas. Christmas Day is always December 25th, however unless your conventional calendar is open to December of your particular year, a question like "what day of the week is Christmas?" difficult to answer.

Unlike the one-page calendar!

Remember the left-hand day of the month. Top-right, you see the month. Put two fingers, one from each hand, on the date (25th) and the month (December). Slide the day hand to the right and the month hand downwards until they touch.

They meet on Monday—December 25, 2023.

For 2023, that's fine, but what happens in 2024? Even worse, what if we want to know the day-of-the-week/day/month combo many years from now?

I think the one-page calendar shines here.

Except for the blue months in the upper-right corner of the one-page calendar, everything is the same year after year. The months also change in a consistent fashion.

Each non-leap year has 365 days—one more than a full 52 weeks (which is 364). Since January 1, 2023 began on a Sunday and 2023 has 365 days, we immediately know that December 31, 2023 will conclude on a Sunday (which you can confirm using the one-page calendar) and that January 1, 2024 will begin on a Monday. Then, reorder the months for 2024, taking in mind that February will have 29 days in a leap year.

Please note the differences between 2023 and 2024 month placement. In 2023:

• October and January began on the same day of the week.

• On the following Monday of the week, May began.

• August started on the next day,

• then the next weekday marked the start of February, March, and November, respectively.

• Unlike June, which starts the following weekday,

• While September and December start on the following day of the week,

• Lastly, April and July start one extra day later.

Since 2024 is a leap year, February has 29 days, disrupting the rhythm. Month placements change to:

• The first day of the week in January, April, and July is the same.

• October will begin the following day.

• Possibly starting the next weekday,

• February and August start on the next weekday,

• beginning on the following day of the week between March and November,

• beginning the following weekday in June,

• and commencing one more day of the week after that, September and December.

Due to the 366-day leap year, 2025 will start two days later than 2024 on January 1st.

Now, looking at the 2025 calendar, you can see that the 2023 pattern of which months start on which days is repeated! The sole variation is a shift of three days-of-the-week ahead because 2023 had one more day (365) than 52 full weeks (364), and 2024 had two more days (366). Again,

• On Wednesday this time, January and October begin on the same day of the week.

• Although May begins on Thursday,

• August begins this Friday.

• March, November, and February all begin on a Saturday.

• Beginning on a Sunday in June

• Beginning on Monday are September and December,

• and on Tuesday, April and July begin.

In 2026 and 2027, the year will commence on a Thursday and a Friday, respectively.

We must return to our leap year monthly arrangement in 2028. Yes, January 1, 2028 begins on a Saturday, but February, which begins on a Tuesday three days before January, will have 29 days. Thus:

• Start dates for January, April, and July are all Saturdays.

• Given that October began on Sunday,

• Although May starts on a Monday,

• beginning on a Tuesday in February and August,

• Beginning on a Wednesday in March and November,

• Beginning on Thursday, June

• and Friday marks the start of September and December.

This is great because there are only 14 calendar configurations: one for each of the seven non-leap years where January 1st begins on each of the seven days of the week, and one for each of the seven leap years where it begins on each day of the week.

The 2023 calendar will function in 2034, 2045, 2051, 2062, 2073, 2079, 2090, 2102, 2113, and 2119. Except when passing over a non-leap year that ends in 00, like 2100, the repeat time always extends to 12 years or shortens to an extra 6 years.

• The pattern is repeated in 2025's calendar in 2031, 2042, 2053, 2059, 2070, 2081, 2087, 2098, 2110, and 2121.

• The extra 6-year repeat at the end of the century on the calendar for 2026 will occur in the years 2037, 2043, 2054, 2065, 2071, 2082, 2093, 2099, 2105, and 2122.

• The 2027s calendar repeats in 2038, 2049, 2055, 2066, 2077, 2083, 2094, 2100, 2106, and 2117, almost exactly matching the 2026s pattern.

For leap years, the recurrence pattern is every 28 years when not passing a non-leap year ending in 00, or 12 or 40 years when we do. 2024's calendar repeats in 2052, 2080, 2120, 2148, 2176, and 2216; 2028's in 2056, 2084, 2124, 2152, 2180, and 2220.

Knowing January 1st and whether it's a leap year lets you construct a one-page calendar for any year. Try it—you might find it easier than any other alternative!

Move people with tiny words.

Apple fanboy here.

• Macs are awesome.

• Their iPhones rock.

• $19 cloths are great.

• $999 stands are amazing.

I love Apple's microcopy even more.

It's like the marketing goddess bit into the Apple logo and blessed the world with microcopy.

I took on a 30-day micro-stalking mission.

Every time I caught myself wasting time on YouTube, I had to visit Apple’s website to learn the secrets of the marketing goddess herself.

We've learned. Golden apples are calling.

Cut the friction

Benefit-first, not commitment-first.

Brands lose customers through friction.

Most brands don't think like customers.

• Brands want sales.

• Brands want newsletter signups.

Here's their microcopy:

• “Buy it now.”

• “Sign up for our newsletter.”

Both are difficult. They ask for big commitments.

People are simple creatures. Want pleasure without commitment.

Apple nails this.

So, instead of highlighting the commitment, they highlight the benefit of the commitment.

Saving on the latest iPhone sounds easier than buying it. Everyone saves, but not everyone buys.

A subtle change in framing reduces friction.

Apple eliminates customer objections to reduce friction.

Less customer friction means simpler processes.

Apple's copy expertly reassures customers about shipping fees and not being home. Apple assures customers that returning faulty products is easy.

Apple knows that talking to a real person is the best way to reduce friction and improve their copy.

Always rhyme

Learn about fine rhyme.

Poets make things beautiful with rhyme.

Copywriters use rhyme to stand out.

Apple’s copywriters have mastered the art of corporate rhyme.

Two techniques are used.

1. Perfect rhyme

Here, rhymes are identical.

2. Imperfect rhyme

Here, rhyming sounds vary.

Apple prioritizes meaning over rhyme.

Apple never forces rhymes that don't fit.

It fits so well that the copy seems accidental.

Add alliteration

Alliteration always entertains.

Alliteration repeats initial sounds in nearby words.

Apple's copy uses alliteration like no other brand I've seen to create a rhyming effect or make the text more fun to read.

For example, in the sentence "Sam saw seven swans swimming," the initial "s" sound is repeated five times. This creates a pleasing rhythm.

Microcopy overuse is like pouring ketchup on a Michelin-star meal.

Alliteration creates a memorable phrase in copywriting. It's subtler than rhyme, and most people wouldn't notice; it simply resonates.

I love how Apple uses alliteration and contrast between "wonders" and "ease".

Assonance, or repeating vowels, isn't Apple's thing.

You ≠ Hero, Customer = Hero

Your brand shouldn't be the hero.

Because they'll be using your product or service, your customer should be the hero of your copywriting. With your help, they should feel like they can achieve their goals.

I love how Apple emphasizes what you can do with the machine in this microcopy.

It's divine how they position their tools as sidekicks to help below.

This one takes the cake:

Dialogue-style writing

Conversational copy engages.

Excellent copy Like sharing gum with a friend.

This helps build audience trust.

Apple does this by using natural connecting words like "so" and phrases like "But that's not all."

Snowclone-proof

The mother of all microcopy techniques.

A snowclone uses an existing phrase or sentence to create a new one. The new phrase or sentence uses the same structure but different words.

It’s usually a well know saying like:

To be or not to be.

This becomes a formula:

To _ or not to _.

Copywriters fill in the blanks with cause-related words. Example:

To click or not to click.

Apple turns "survival of the fittest" into "arrival of the fittest."

It's unexpected and surprises the reader.

So this was fun.

But my fun has just begun.

Microcopy is 21st-century poetry.

I came as an Apple fanboy.

I leave as an Apple fanatic.

Now I’m off to find an apple tree.

Cause you know how it goes.

(Apples, trees, etc.)

This post is a summary. Original post available here.