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.

I recently wrote about getting VCs excited about Marketplace start-ups. SaaS founders became envious!

Understanding how people wire tens of millions is the only Series A hack I recommend.

Few people understand the intellectual process behind investing.

VC is risk management.

Series A-focused VCs must cover two risks.

1. Market risk

You need a large market to cross a threshold beyond which you can build defensibilities. Series A VCs underwrite market risk.

They must see you have reached product-market fit (PMF) in a large total addressable market (TAM).

2. Execution risk

When evaluating your growth engine's blitzscaling ability, execution risk arises.

When investors remove operational uncertainty, they profit.

Series A VCs like businesses with derisked revenue streams. Don't raise unless you have a predictable model, pipeline, and growth.

Please beat these 3 metrics before Series A:

Achieve $1.5m ARR in 12-24 months (Market risk)

Above 100% Net Dollar Retention. (Market danger)

Lead Velocity Rate supporting $10m ARR in 2–4 years (Execution risk)

Hit the 3 and you'll raise $10M in 4 months. Discussing 2/3 may take 6–7 months.

If none, don't bother raising and focus on becoming a capital-efficient business (Topics for other posts).

Let's examine these 3 metrics for the brave ones.

1. Lead Velocity Rate supporting €$10m ARR in 2 to 4 years

Last because it's the least discussed. LVR is the most reliable data when evaluating a growth engine, in my opinion.

SaaS allows you to see the future.

Monthly Sales and Sales Pipelines, two predictive KPIs, have poor data quality. Both are lagging indicators, and minor changes can cause huge modeling differences.

Analysts and Associates will trash your forecasts if they're based only on Monthly Sales and Sales Pipeline.

LVR, defined as month-over-month growth in qualified leads, is rock-solid. There's no lag. You can See The Future if you use Qualified Leads and a consistent formula and process to qualify them.

With this metric in your hand, scaling your company turns into an execution play on which VCs are able to perform calculations risk.

2. Above-100% Net Dollar Retention.

Net Dollar Retention is a better-known SaaS health metric than LVR.

Net Dollar Retention measures a SaaS company's ability to retain and upsell customers. Ask what $1 of net new customer spend will be worth in years n+1, n+2, etc.

Depending on the business model, SaaS businesses can increase their share of customers' wallets by increasing users, selling them more products in SaaS-enabled marketplaces, other add-ons, and renewing them at higher price tiers.

If a SaaS company's annualized Net Dollar Retention is less than 75%, there's a problem with the business.

Slack's ARR chart (below) shows how powerful Net Retention is. Layer chart shows how existing customer revenue grows. Slack's S1 shows 171% Net Dollar Retention for 2017–2019.

Slack S-1

3. $1.5m ARR in the last 12-24 months.

According to Point 9, $0.5m-4m in ARR is needed to raise a $5–12m Series A round.

Target at least what you raised in Pre-Seed/Seed. If you've raised $1.5m since launch, don't raise before $1.5m ARR.

Capital efficiency has returned since Covid19. After raising $2m since inception, it's harder to raise $1m in ARR.

P9's 2016-2021 SaaS Funding Napkin

In summary, less than 1% of companies VCs meet get funded. These metrics can help you win.

If there’s demand for it, I’ll do one on direct-to-consumer.

Cheers!

Open to ideas or acquisitions

Failure is an unavoidable aspect of life, yet many recoil at the word.

I've worked on unrelated startup projects. This is a list of products I developed (often as the tech lead or co-founder) and why they failed to launch.

Chess Bet (Betting)

As a chess player who plays 5 games a day and has an ELO rating of 2100, I tried to design a chess engine to rival stockfish and Houdini.

While constructing my chess engine, my cofounder asked me about building a p2p chess betting app. Chess Bet. There couldn't be a better time.

Two people in different locations could play a staked game. The winner got 90% of the bet and we got 10%. The business strategy was clear, but our mini-launch was unusual.

People started employing the same cheat engines I mentioned, causing user churn and defaming our product.

It was the first programming problem I couldn't solve after building a cheat detection system based on player move strengths and prior games. Chess.com, the most famous online chess software, still suffers from this.

We decided to pivot because we needed an expensive betting license.

We relaunched as Chess MVP after deciding to focus on chess learning. A platform for teachers to create chess puzzles and teach content. Several chess students used our product, but the target market was too tiny.

We chose to quit rather than persevere or pivot.

BodaCare (Insure Tech)

‘BodaBoda’ in Swahili means Motorcycle. My Dad approached me in 2019 (when I was working for a health tech business) about establishing an Insurtech/fintech solution for motorbike riders to pay for insurance using SNPL.

We teamed up with an underwriter to market motorcycle insurance. Once they had enough premiums, they'd get an insurance sticker in the mail. We made it better by splitting the cover in two, making it more reasonable for motorcyclists struggling with lump-sum premiums.

Lack of capital and changing customer behavior forced us to close, with 100 motorcyclists paying 0.5 USD every day. Our unit econ didn't make sense, and CAC and retention capital only dug us deeper.

Circle (Social Networking)

Having learned from both product failures, I began to understand what worked and what didn't. While reading through Instagram, an idea struck me.

Suppose social media weren't virtual.

Imagine meeting someone on your way home. Like-minded person

People were excited about social occasions after covid restrictions were eased. Anything to escape. I just built a university student-popular experiences startup. Again, there couldn't be a better time.

I started the Android app. I launched it on Google Beta and oh my! 200 people joined in two days.

It works by signaling if people are in a given place and allowing users to IM in hopes of meeting up in near real-time. Playstore couldn't deploy the app despite its success in beta for unknown reasons. I appealed unsuccessfully.

My infrastructure quickly lost users because I lacked funding.

In conclusion

This essay contains many failures, some of which might have been avoided and others not, but they were crucial learning points in my startup path.

If you liked any idea, I have the source code on Github.

Happy reading until then!

Peter Thiel studied philosophy as an undergraduate.

Peter Thiel has $7.36 billion.

Peter is a world-ranked chess player, has a legal degree, and has written profitable novels.

In 1999, he co-founded PayPal with Max Levchin, which merged with X.com.

Peter Thiel made $55 million after selling the company to eBay for $1.5 billion in 2002.

You may be wondering…

How did Peter turn $55 million into his now multi-billion dollar net worth?

One amazing investment?

Facebook.

Thiel was Facebook's first external investor. He bought 10% of the company for $500,000 in 2004.

This investment returned 159% annually, 200x in 8 years.

By 2012, Thiel sold almost all his Facebook shares, becoming a billionaire.

What was the investment thesis of Peter?

This investment appeared ridiculous. Facebook was an innovative startup.

Thiel's $500,000 contribution transformed Facebook.

Harvard students have access to Facebook's 8 features and 1 photo per profile.

How did Peter determine that this would be a wise investment, then?

Facebook is a mimetic desire machine.

Social media's popularity is odd. Why peek at strangers' images on a computer?

Peter Thiel studied under French thinker Rene Girard at Stanford.

Mimetic Desire explains social media's success.

Mimetic Desire is the idea that humans desire things simply because other people do.

If nobody wanted it, would you?

Would you desire a family, a luxury car, or expensive clothes if no one else did? Girard says no.

People we admire affect our aspirations because we're social animals. Every person has a role model.

Our nonreligious culture implies role models are increasingly other humans, not God.

The idea explains why social media influencers are so powerful.

Why would Andrew Tate or Kim Kardashian matter if people weren't mimetic?

Humanity is fundamentally motivated by social comparison.

Facebook takes advantage of this need for social comparison, and puts it on a global scale.

It aggregates photographs and updates from millions of individuals.

Facebook mobile allows 24/7 social comparison.

Thiel studied mimetic desire with Girard and realized Facebook exploits the urge for social comparison to gain money.

Social media is more significant and influential than ever, despite Facebook's decline.

Thiel and Girard show that applied philosophy (particularly in business) can be immensely profitable.

Are you one of these Zoom dogs?

The Person Who Is Apparently Always on Mute

Waffles thinks he can overpower the mute button by shouting loudly.

The person who believed their camera to be off

Barkley's used to remote work, but he hasn't mastered the "Stop Video" button. Everyone is affected.

Who is driving for some reason, exactly?

Why is Pumpkin always late? Who knows? Shouldn't she be driving? If you could hear her over the freeway, she'd answer these questions.

The Person With the Amazing Bookcase

Cicero likes to use SAT-words like "leverage" and "robust" in Zoom sessions, presumably from all the books he wants you to see behind him.

The Individual Who Is Unnecessarily Dressed

We hope Bandit is going somewhere beautiful after this meeting, or else he neglected the quarterly earnings report and is overcompensating to distract us.

The person who works through lunch in between zoom calls

Barksworth has back-to-back meetings all day, so you can watch her eat while she talks.

The Person Who Is A Little Too Comfy

Hercules thinks Zoom meetings happen between sleeps. He'd appreciate everyone speaking more quietly.

The Person Who Answered the Phone Outside

Frisbee has a gorgeous backyard and lives in a place with great weather year-round, and she wants you to think about that during the daily team huddle.

Who Wants You to Pay Attention to Their Pet

Snickers hasn't listened to you in 20 minutes unless you tell her how cute her kitten is.

One who is, for some reason, positioned incorrectly on the screen

Nelson's meetings consist primarily of attempting to figure out how he positioned his laptop so absurdly.

The person who says too many goodbyes

Zeus waves farewell like it's your first day of school while everyone else searches for the "Leave Meeting" button. It's nice.

He who has a poor internet connection

Ziggy's connectivity problems continue... She gives a long speech as everyone waits awkwardly to inform her they missed it.

The Clearly Multitasking Person

Tinkerbell can play fetch during the monthly staff meeting if she works from home, but that's not a good idea.

The Person Using Zoom as a Makeup and Hair Mirror

If Gail and Bob knew Zoom had a "hide self view" option, they'd be distraught.

The person who feels at ease with simply leaving

Rusty bails when a Zoom conference is over. Rusty's concept is decent.