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.

Most don't understand the issue until it's too late.

My first startup was what entrepreneurs call the hardest. A two-sided marketplace.

Two-sided marketplaces are the hardest startups because founders must solve the chicken or the egg conundrum.

A two-sided marketplace needs suppliers and buyers. Without suppliers, buyers won't come. Without buyers, suppliers won't come. An empty marketplace and a founder striving to gain momentum result.

My first venture made me a struggling founder seeking to achieve traction for a two-sided marketplace. The company failed, and I vowed never to start another like it.

I didn’t. Unfortunately, my second venture was almost as hard. It failed like the second-hardest startup.

What kind of startup is the second-hardest?

The second-hardest startup, which is almost as hard to develop, is rarely discussed in the startup community. Because of this, I predict more founders fail each year trying to develop the second-toughest startup than the hardest.

Fairly, I have no proof. I see many startups, so I have enough of firsthand experience. From what I've seen, for every entrepreneur developing a two-sided marketplace, I'll meet at least 10 building this other challenging startup.

I'll describe a startup I just met with its two co-founders to explain the second hardest sort of startup and why it's so hard. They created a financial literacy software for parents of high schoolers.

The issue appears plausible. Children struggle with money. Parents must teach financial responsibility. Problems?

It's possible.

Buyers and users are different.

Buyer-user mismatch.

The financial literacy app I described above targets parents. The parent doesn't utilize the app. Child is end-user. That may not seem like much, but it makes customer and user acquisition and onboarding difficult for founders.

The difficulty of a buyer-user imbalance

The company developing a product faces a substantial operational burden when the buyer and end customer are different. Consider classic firms where the buyer is the end user to appreciate that responsibility.

Entrepreneurs selling directly to end users must educate them about the product's benefits and use. Each demands a lot of time, effort, and resources.

Imagine selling a financial literacy app where the buyer and user are different. To make the first sale, the entrepreneur must establish all the items I mentioned above. After selling, the entrepreneur must supply a fresh set of resources to teach, educate, or train end-users.

Thus, a startup with a buyer-user mismatch must market, sell, and train two organizations at once, requiring twice the work with the same resources.

The second hardest startup is hard for reasons other than the chicken-or-the-egg conundrum. It takes a lot of creativity and luck to solve the chicken-or-egg conundrum.

The buyer-user mismatch problem cannot be overcome by innovation or luck. Buyer-user mismatches must be solved by force. Simply said, when a product buyer is different from an end-user, founders have a lot more work. If they can't work extra, their companies fail.

“Poor distribution, not poor goods, is the main reason for failure” — Peter Thiel.

Here's an easy way to conceptualize "go-to-market" for your distribution plan.

One equation captures the concept:

Distribution = Ecosystem Participants + Incentives

Draw your customers' ecosystem. Set aside your goods and consider your consumer's environment. Who do they deal with daily? 

1. First, list each participant. You want an exhaustive list, but here are some broad categories.

• In-person media services

• Websites

• Events\Networks

• Financial education and banking

• Shops

• Staff

• Advertisers

• Twitter influencers

1. Draw influence arrows. Who's affected? I'm not just talking about Instagram selfie-posters. Who has access to your consumer and could promote your product if motivated?

The thicker the arrow, the stronger the relationship. Include more "influencers" if needed. Customer ecosystems are complex.

3. Incentivize ecosystem players. “Show me the incentive and I will show you the result.“, says Warren Buffet's business partner Charlie Munger.

Strong distribution strategies encourage others to promote your product to your target market by incentivizing the most prominent players. Incentives can be financial or non-financial.

Financial rewards

Usually, there's money. If you pay Facebook, they'll run your ad. Salespeople close deals for commission. Giving customers bonus credits will encourage referrals.

Most businesses underuse non-financial incentives.

Non-cash incentives

Motivate key influencers without spending money to expand quickly and cheaply. What can you give a client-connector for free?

Here are some ideas:

Are there any other features or services available?

Titles or status? Tinder paid college "ambassadors" for parties to promote its dating service.

Can I get early/free access? Facebook gave a select group of developers "exclusive" early access to their AR platform.

Are you a good host? Pharell performed at YPlan's New York launch party.

Distribution? Apple's iPod earphones are white so others can see them.

Have an interesting story? PR rewards journalists by giving them a compelling story to boost page views.

Prioritize distribution.

More time spent on distribution means more room in your product design and business plan. Once you've identified the key players in your customer's ecosystem, talk to them.

Money isn't your only resource. Creative non-monetary incentives may be more effective and scalable. Give people something useful and easy to deliver.

A reading list for successful people

Elon Musk reads and talks. So, one learns. Many brilliant individuals & amazing literature.

This article recommends 3 Elon Musk novels. All of them helped me succeed. Hope they'll help you.

Douglas Adams's The Hitchhiker's Guide to the Galaxy

Page Count: 193
Rating on Goodreads: 4.23

Arthur Dent is pulled off Earth by a buddy seconds before it's razed for a cosmic motorway. The trio hitchhikes through space and gets into problems.

I initially read Hitchhiker's as a child. To evade my mum, I'd read with a flashlight under the covers. She'd scold at me for not sleeping on school nights when she found out. Oops.

The Hitchhiker's Guide to the Galaxy is lighthearted science fiction.

My favorite book quotes are:

• “Space is big. You won’t believe how vastly, hugely, mind-bogglingly big it is. I mean, you may think it’s a long way down the road to the chemist’s, but that’s just peanuts to space.”

• “Far out in the uncharted backwaters of the unfashionable end of the western spiral arm of the Galaxy lies a small unregarded yellow sun. Orbiting this at a distance of roughly ninety-two million miles is an utterly insignificant little blue-green planet whose ape-descended life forms are so amazingly primitive that they still think digital watches are a pretty neat idea.”

• “On planet Earth, man had always assumed that he was more intelligent than dolphins because he had achieved so much — the wheel, New York, wars, and so on — whilst all the dolphins had ever done was muck about in the water having a good time. But conversely, the dolphins had always believed that they were far more intelligent than man — for precisely the same reasons.”

the Sun Tzu book The Art Of War

Page Count: 273
Rating on Goodreads: 3.97

It's a classic. You may apply The Art of War's ideas to (nearly) every facet of life. Ex:

• Pick your fights.

• Keep in mind that timing is crucial.

• Create a backup plan in case something goes wrong.

• Obstacles provide us a chance to adapt and change.

This book was my first. Since then, I'm a more strategic entrepreneur. Excellent book. And read it ASAP!

My favorite book quotes are:

• “Victorious warriors win first and then go to war, while defeated warriors go to war first and then seek to win.”

• “Engage people with what they expect; it is what they are able to discern and confirms their projections. It settles them into predictable patterns of response, occupying their minds while you wait for the extraordinary moment — that which they cannot anticipate.”

• “If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained, you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle.”

Peter Thiel's book Zero to One

Page Count: 195
Rating on Goodreads: 4.18

Peter argues the best money-making strategies are typically unproven. Entrepreneurship should never have a defined path to success. Whoever says differently is lying.

Zero to One explores technology and society. Peter is a philosophy major and law school graduate, which informs the work.

Peters' ideas, depth, and intellect stood out in Zero to One. It's a top business book.

My favorite book quotes are:

• “The most valuable businesses of coming decades will be built by entrepreneurs who seek to empower people rather than try to make them obsolete.”

• “The next Bill Gates will not build an operating system. The next Larry Page or Sergey Brin won’t make a search engine. And the next Mark Zuckerberg won’t create a social network. If you are copying these guys, you aren’t learning from them.”

• “If your goal is to never make a mistake in your life, you shouldn’t look for secrets. The prospect of being lonely but right — dedicating your life to something that no one else believes in — is already hard. The prospect of being lonely and wrong can be unbearable.”

Most productive people are habitual.

Early in the day, do important tasks.

In his best-selling book Eat That Frog, Brian Tracy advised starting the day with your hardest, most important activity.

Most individuals work best in the morning. Energy and willpower peak then.

Mornings are also ideal for memory, focus, and problem-solving.

Thus, the morning is ideal for your hardest chores.

It makes sense to do these things during your peak performance hours.

Additionally, your morning sets the tone for the day. According to Brian Tracy, the first hour of the workday steers the remainder.

After doing your most critical chores, you may feel accomplished, confident, and motivated for the remainder of the day, which boosts productivity.

Develop Your Essentialism

In Essentialism, Greg McKeown claims that trying to be everything to everyone leads to mediocrity and tiredness.

You'll either burn out, be spread too thin, or compromise your ideals.

Greg McKeown advises Essentialism:

Clarify what’s truly important in your life and eliminate the rest.

Eliminating non-essential duties, activities, and commitments frees up time and energy for what matters most.

According to Greg McKeown, Essentialists live by design, not default.

You'll be happier and more productive if you follow your essentials.

Follow these three steps to live more essentialist.

Prioritize Your Tasks First

What matters most clarifies what matters less. List your most significant aims and values.

The clearer your priorities, the more you can focus on them.

On Essentialism, McKeown wrote, The ultimate form of effectiveness is the ability to deliberately invest our time and energy in the few things that matter most.

#2: Set Your Priorities in Order

Prioritize your priorities, not simply know them.

“If you don’t prioritize your life, someone else will.” — Greg McKeown

Planning each day and allocating enough time for your priorities is the best method to become more purposeful.

#3: Practice saying "no"

If a request or demand conflicts with your aims or principles, you must learn to say no.

Saying no frees up space for our priorities.

Place Sleep Above All Else

Many believe they must forego sleep to be more productive. This is false.

A productive day starts with a good night's sleep.

Matthew Walker (Why We Sleep) says:

“Getting a good night’s sleep can improve cognitive performance, creativity, and overall productivity.”

Sleep helps us learn, remember, and repair.

Unfortunately, 35% of people don't receive the recommended 79 hours of sleep per night.

Sleep deprivation can cause:

• increased risk of diabetes, heart disease, stroke, and obesity

• Depression, stress, and anxiety risk are all on the rise.

• decrease in general contentment

• decline in cognitive function

To live an ideal, productive, and healthy life, you must prioritize sleep.

Follow these six sleep optimization strategies to obtain enough sleep:

• Establish a nightly ritual to relax and prepare for sleep.

• Avoid using screens an hour before bed because the blue light they emit disrupts the generation of melatonin, a necessary hormone for sleep.

• Maintain a regular sleep schedule to control your body's biological clock (and optimizes melatonin production)

• Create a peaceful, dark, and cool sleeping environment.

• Limit your intake of sweets and caffeine (especially in the hours leading up to bedtime)

• Regular exercise (but not right before you go to bed, because your body temperature will be too high)

Sleep is one of the best ways to boost productivity.

Sleep is crucial, says Matthew Walker. It's the key to good health and longevity.

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!