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.

Massive Layoffs, record low VC investment, debate over crash... why is it happening and what’s the endgame?

This article generalizes a diverse industry. For objectivity, specific tech company challenges like growing competition within named segments won't be considered. Please comment on the posts.

According to Layoffs.fyi, nearly 120.000 people have been fired from startups since March 2020. More than 700 startups have fired 1% to 100% of their workforce. "The tech market is crashing"

Venture capital investment dropped 19% QoQ in the first four months of 2022, a 2018 low. Since January 2022, Nasdaq has dropped 27%. Some believe the tech market is collapsing.

It's bad, but nothing has crashed yet. We're about to get super technical, so buckle up!

I've written a follow-up article about what's next. For a more optimistic view of the crisis' aftermath, see: Tech Diaspora and Silicon Valley crisis

What happened?

Insanity reigned. Last decade, everyone became a unicorn. Seed investments can be made without a product or team. While the "real world" economy suffered from the pandemic for three years, tech companies enjoyed the "new normal."

COVID sped up technology adoption on several fronts, but this "new normal" wasn't so new after many restrictions were lifted. Worse, it lived with disrupted logistics chains, high oil prices, and WW3. The consumer market has felt the industry's boom for almost 3 years. Inflation, unemployment, mental distress...what looked like a fast economic recovery now looks like unfulfilled promises.

People rethink everything they eat. Paying a Netflix subscription instead of buying beef is moronic if you can watch it for free on your cousin’s account. No matter how great your real estate app's UI is, buying a house can wait until mortgage rates drop. PLGProduct Led Growth (PLG) isn't the go-to strategy when consumers have more basic expense priorities.

Exponential growth and investment

Until recently, tech companies believed that non-exponential revenue growth was fatal. Exponential growth entails doing more with less. From Salim Ismail words:

An Exponential Organization (ExO) has 10x the impact of its peers.

Many tech companies' theories are far from reality.

Investors have funded (sometimes non-exponential) growth. Scale-driven companies throw people at problems until they're solved. Need an entire closing team because you’ve just bought a TV prime time add? Sure. Want gold-weight engineers to colorize buttons? Why not?

Tech companies don't need cash flow to do it; they can just show revenue growth and get funding. Even though it's hard to get funding, this was the market's momentum until recently.

The graph at the beginning of this section shows how industry heavyweights burned money until 2020, despite being far from their market-share seed stage. Being big and being sturdy are different things, and a lot of the tech startups out there are paper tigers. Without investor money, they have no foundation.

A little bit about interest rates

Inflation-driven high interest rates are said to be causing tough times. Investors would rather leave money in the bank than spend it (I myself said it some days ago). It’s not wrong, but it’s also not that simple.

The USA central bank (FED) is a good proxy of global economics. Dollar treasury bonds are the safest investment in the world. Buying U.S. debt, the only country that can print dollars, guarantees payment.

The graph above shows that FED interest rates are low and 10+ year bond yields are near 2018 levels. Nobody was firing at 2018. What’s with that then?

Full explanation is too technical for this article, so I'll just summarize: Bond yields rise due to lack of demand or market expectations of longer-lasting inflation. Safe assets aren't a "easy money" tactic for investors. If that were true, we'd have seen the current scenario before.

Long-term investors are protecting their capital from inflation.

Not a crash, a landing

I bombarded you with info... Let's review:

• Consumption is down, hurting revenue.

• Tech companies of all ages have been hiring to grow revenue at the expense of profit.

• Investors expect inflation to last longer, reducing future investment gains.

Inflation puts pressure on a wheel that was rolling full speed not long ago. Investment spurs hiring, growth, and more investment. Worried investors and consumers reduce the cycle, and hiring follows.

Long-term investors back startups. When the invested company goes public or is sold, it's ok to burn money. What happens when the payoff gets further away? What if all that money sinks? Investors want immediate returns.

Why isn't the market crashing? Technology is not losing capital. It’s expecting change. The market realizes it threw moderation out the window and is reversing course. Profitability is back on the menu.

People solve problems and make money, but they also cost money. Huge cost for the tech industry. Engineers, Product Managers, and Designers earn up to 100% more than similar roles. Businesses must be careful about who they keep and in what positions to avoid wasting money.

What the future holds

From here on, it's all speculation. I found many great articles while researching this piece. Some are cited, others aren't (like this and this). We're in an adjustment period that may or may not last long.

Big companies aren't laying off many workers. Netflix firing 100 people makes headlines, but it's only 1% of their workforce. The biggest seem to prefer not hiring over firing.

Smaller startups beyond the seeding stage may be hardest hit. Without structure or product maturity, many will die.

I expect layoffs to continue for some time, even at Meta or Amazon. I don't see any industry names falling like they did during the .com crisis, but the market will shrink.

If you are currently employed, think twice before moving out and where to.
If you've been fired, hurry, there are still many opportunities.
If you're considering a tech career, wait.
If you're starting a business, I respect you. Good luck.

My ego is so huge it won't fit through the door.

I don't know how I feel about it. I should be excited. Many of you have this exact dream to publish a book with a well-known book publisher and get a juicy advance.

Let me dissect how I'm thinking about it to help you.

How it happened

An email comes in. A generic "can we put a backlink on your website and get a freebie" email.

Almost deleted it.

Then I noticed the logo. It seemed shady. I found the URL. Check. I searched the employee's LinkedIn. Legit. I avoided middlemen. Check.

Mixed feelings. LinkedIn hasn't valued my writing for years. I'm just a guy in an unironed t-shirt whose content they sell advertising against.

They get big dollars. I get $0 and a few likes, plus some email subscribers.

Still, I felt adrenaline for hours.

I texted a few friends to see how they felt. I wrapped them.

Messages like "No shocker. You're entertaining online." I didn't like praises, so I blushed.

The thrill faded after hours. Who knows?

Most authors desire this chance.

"You entitled piece of crap, Denning!"

You may think so. Okay. My job is to stand on the internet and get bananas thrown at me.

I approached writing backwards. More important than a book deal was a social media audience converted to an email list.

Romantic authors think backward. They hope a fantastic book will land them a deal and an audience.

Rarely occurs. So I never pursued it. It's like permission-seeking or the lottery.

Not being a professional writer, I've never written a good book. I post online for fun and to express my opinions.

Writing is therapeutic. I overcome mental illness and rebuilt my life this way. Without blogging, I'd be dead.

I've always dreamed of staying alive and doing something I love, not getting a book contract. Writing is my passion. I'm a winner without a book deal.

Why I was given a book deal

You may assume I received a book contract because of my views or follows. Nope.

They gave me a deal because they like my writing style. I've heard this for eight years.

Several authors agree. One asked me to improve their writer's voice.

Takeaway: highlight your writer's voice.

What if they discover I'm writing incompetently?

An edited book is published. It's edited.

I need to master writing mechanics, thus this concerns me. I need help with commas and sentence construction.

I must learn verb, noun, and adjective. Seriously.

Writing a book may reveal my imposter status to a famous publisher. Imagine the email

"It happened again. He doesn't even know how to spell. He thinks 'less' is the correct word, not 'fewer.' Are you sure we should publish his book?"

Fears stink.

I'm capable of blogging. Even listicles. So what?

Writing for a major publisher feels advanced.

I only blog. I'm good at listicles. Digital media executives have criticized me for this.

• It is allegedly clickbait.

• Or it is following trends.

• Alternately, growth hacking.

Never. I learned copywriting to improve my writing.

Apple, Amazon, and Tesla utilize copywriting to woo customers. Whoever thinks otherwise is the wisest person in the room.

Old-schoolers loathe copywriters.

Their novels sell nothing.

They assume their elitist version of writing is better and that the TikTok generation will invest time in random writing with no subheadings and massive walls of text they can't read on their phones.

I'm terrified of book proposals.

My friend's book proposal suggestion was contradictory and made no sense.

They told him to compose another genre. This book got three Amazon reviews. Is that a good model?

The process disappointed him. I've heard other book proposal horror stories. Tim Ferriss' book "The 4-Hour Workweek" was criticized.

Because he has thick skin, his book came out. He wouldn't be known without that.

I hate book proposals.

An ongoing commitment

Writing a book is time-consuming.

I appreciate time most. I want to focus on my daughter for the next few years. I can't recreate her childhood because of a book.

No idea how parents balance kids' goals.

My silly face in a bookstore. Really?

Genuine thought.

I don't want my face in bookstores. I fear fame. I prefer anonymity.

I want to purchase a property in a bad Australian area, then piss off and play drums. Is bookselling worth it?

Are there even bookstores anymore?

(Except for Ryan Holiday's legendary Painted Porch Bookshop in Texas.)

What's most important about books

Many were duped.

Tweets and TikTok hopscotch vids are their future. Short-form content creates devoted audiences that buy newsletter subscriptions.

Books=depth.

Depth wins (if you can get people to buy your book). Creating a book will strengthen my reader relationships.

It's cheaper than my classes, so more people can benefit from my life lessons.

A deeper justification for writing a book

Mind wandered.

If I write this book, my daughter will follow it. "Look what you can do, love, when you ignore critics."

That's my favorite.

I'll be her best leader and teacher. If her dad can accomplish this, she can too.

My kid can read my book when I'm gone to remember her loving father.

Last paragraph made me cry.

The positive

This book thing might make me sound like Karen.

The upside is... Building in public, like I have with online writing, attracts the right people.

Proof-of-work over proposals, beautiful words, or huge aspirations. If you want a book deal, try writing online instead of the old manner.

Next steps

No idea.

I'm a rural Aussie. Writing a book in the big city is intimidating. Will I do it? Lots to think about. Right now, some level of reflection and gratitude feels most appropriate.

Sometimes when you don't feel worthy, it gives you the greatest lessons. That's how I feel about getting offered this book deal.

Perhaps you can relate.

The holy grail of plain text task management is finally within reach

Plain text task management? Are you serious?? Dedicated task managers exist for a reason, you know. Sheesh.

—Oh, I know. Believe me, I know! But hear me out.

I've managed projects and tasks in plain text for more than four years. Since reorganizing my to-do list, plain text task management is within reach.

Data completely yours? One billion percent. Beef it up with coding? Be my guest.

Enter: The List

The answer? A list. That’s it!

Write down tasks. Obsidian, Notenik, Drafts, or iA Writer are good plain text note-taking apps.

List too long? Of course, it is! A large list tells you what to do. Feel the itch and friction. Then fix it.

• But I want to be able to distinguish between work and personal life! List two things.

• However, I need to know what should be completed first. Put those items at the top.

• However, some things keep coming up, and I need to be reminded of them! Put those in your calendar and make an alarm for them.

• But since individual X hasn't completed task Y, I can't proceed with this. Create a Waiting section on your list by dividing it.

• But I must know what I'm supposed to be doing right now! Read your list(s). Check your calendar. Think critically.

Before I begin a new one, I remind myself that "Listory Never Repeats."

There’s no such thing as too many lists if all are needed. There is such a thing as too many lists if you make them before they’re needed. Before they complain that their previous room was small or too crowded or needed a new light.

A list that feels too long has a voice; it’s telling you what to do next.

I use one Master List. It's a control panel that tells me what to focus on short-term. If something doesn't need semi-immediate attention, it goes on my Backlog list.

Todd Lewandowski's DWTS (Done, Waiting, Top 3, Soon) performance deserves praise. His DWTS to-do list structure has transformed my plain-text task management. I didn't realize it was upside down.

This is my take on it:

D = Done

Move finished items here. If they pile up, clear them out every week or month. I have a Done Archive folder.

W = Waiting

Things seething in the background, awaiting action. Stir them occasionally so they don't burn.

T = Top 3

Three priorities. Personal comes first, then work. There will always be a top 3 (no more than 5) in every category. Projects, not chores, usually.

S = Soon

This part is action-oriented. It's for anything you can accomplish to finish one of the Top 3. This collection includes thoughts and project lists. The sole requirement is that they should be short-term goals.

Some of you have probably concluded this isn't for you. Please read Todd's piece before throwing out the baby. Often. You shouldn't miss a newborn.

As much as Dancing With The Stars helps me recall this method, I may try switching their order. TSWD; Drilling Tunnel Seismic? Serenity After Task?

Master List Showcase

My Master List lives alone in its own file, but sometimes appears in other places.  It's included in my Weekly List template. Here's a (soon-to-be-updated) demo vault of my Obsidian planning setup to download for free.

Here's the code behind my weekly screenshot:

## [[Master List - 2022|✓]]  TO DO

![[Master List - 2022]]

FYI, I use the Minimal Theme in Obsidian, with a few tweaks.

You may note I'm utilizing a checkmark as a link. For me, that's easier than locating the proper spot to click on the embed.

Blue headings for Done and Waiting are links. Done links to the Done Archive page and Waiting to a general waiting page.

Read my full article here.

This is how to build a car while driving.

Building a high-growth startup is compared to building a car while it's speeding down the highway.

How to plan without going crazy? Or, without losing team, board, and investor buy-in?

I just delivered our company's product roadmap for the rest of the year. Complete. Thorough. Page-long. I'm optimistic about its chances of surviving as everything around us changes, from internal priorities to the global economy.

It's tricky. This isn't the first time I've created a startup roadmap. I didn't invent a document. It took time to deliver a document that will be relevant for months.

Goals matter.

Although they never change, goals are rarely understood.

This is the third in a series about a startup's unique roadmapping needs. Velocity is the intensity at which a startup must produce to survive.

A high-growth startup moves at breakneck speed, which I alluded to when I said priorities and economic factors can change daily or weekly.

At that speed, a startup's roadmap must be flexible, bend but not break, and be brief and to the point. I can't tell you how many startups and large companies develop a product roadmap every quarter and then tuck it away.

Big, wealthy companies can do this. It's suicide for a startup.

The drawer thing happens because startup product roadmaps are often valid for a short time. The roadmap is a random list of features prioritized by different company factions and unrelated to company goals.

It's not because the goals changed that a roadmap is shelved or ignored. Because the company's goals were never communicated or documented in the context of its product.

In the previous post, I discussed how to turn company goals into a product roadmap. In this post, I'll show you how to make a one-page startup roadmap.

In a future post, I'll show you how to follow this roadmap. This roadmap helps you track company goals, something a roadmap must do.

Be vague for growth, but direct for execution.

Here's my plan. The real one has more entries and more content in each.

Let's discuss smaller boxes.

Product developers and engineers know that the further out they predict, the more wrong they'll be. When developing the product roadmap, this rule is ignored. Then it bites us three, six, or nine months later when we haven't even started.

Why do we put everything in a product roadmap like a project plan?

Yes, I know. We use it when the product roadmap isn't goal-based.

A goal-based roadmap begins with a document that outlines each goal's idea, execution, growth, and refinement.

Once the goals are broken down into epics, initiatives, projects, and programs, only the idea and execution phases should be modeled. Any goal growth or refinement items should be vague and loosely mapped.

Why? First, any idea or execution-phase goal will result in growth initiatives that are unimaginable today. Second, internal priorities and external factors will change, but the goals won't. Locking items into calendar slots reduces flexibility and forces deviation from the single source of truth.

No soothsayers. Predicting the future is pointless; just prepare.

A map is useless if you don't know where you're going.

As we speed down the road, the car and the road will change. Goals define the destination.

This quarter and next quarter's roadmap should be set. After that, you should track destination milestones, not how to get there.

When you do that, even the most critical investors will understand the roadmap and buy in. When you track progress at the end of the quarter and revise your roadmap, the destination won't change.