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.

Startup entrepreneurs assume what risks when pitching?

Last week I signed four NDAs.

Four!

NDA stands for non-disclosure agreement. A legal document given to someone receiving confidential information. By signing, the person pledges not to share the information for a certain time. If they do, they may be in breach of contract and face legal action.

Companies use NDAs to protect trade secrets and confidential internal information from employees and contractors. Appropriate. If you manage a huge, successful firm, you don't want your employees selling their information to your competitors. To be true, business NDAs don't always prevent corporate espionage, but they usually make employees and contractors think twice before sharing.

I understand employee and contractor NDAs, but I wasn't asked to sign one. I counsel entrepreneurs, thus the NDAs I signed last week were from startups that wanted my feedback on their concepts.

I’m not a startup investor. I give startup guidance online. Despite that, four entrepreneurs thought their company ideas were so important they wanted me to sign a generically written legal form they probably acquired from a shady, spam-filled legal templates website before we could chat.

False. One company tried to get me to sign their NDA a few days after our conversation. I gently rejected, but their tenacity encouraged me. I considered sending retroactive NDAs to everyone I've ever talked to about one of my startups in case they establish a successful company based on something I said.

Two of the other three NDAs were from nearly identical companies. Good thing I didn't sign an NDA for the first one, else they may have sued me for talking to the second one as though I control the firms people pitch me.

I wasn't talking to the fourth NDA company. Instead, I received an unsolicited email from someone who wanted comments on their fundraising pitch deck but required me to sign an NDA before sending it.

That's right, before I could read a random Internet stranger's unsolicited pitch deck, I had to sign his NDA, potentially limiting my ability to discuss what was in it.

You should understand. Advisors, mentors, investors, etc. talk to hundreds of businesses each year. They cannot manage all the companies they deal with, thus they cannot risk legal trouble by talking to someone. Well, if I signed NDAs for all the startups I spoke with, half of the 300+ articles I've written on Medium over the past several years could get me sued into the next century because I've undoubtedly addressed topics in my articles that I discussed with them.

The four NDAs I received last week are part of a recent trend of entrepreneurs sending out NDAs before meetings, despite the practical and legal issues. They act like asking someone to sign away their right to talk about all they see and hear in a day is as straightforward as asking for a glass of water.

Given this inflow of NDAs, I wanted to briefly remind entrepreneurs reading this blog about the merits and cons of requesting investors (or others in the startup ecosystem) to sign your NDA.

Benefits of having investors sign your NDA include:

None. Zero. Nothing.

Disadvantages of requesting investor NDAs:

• You'll come off as an amateur who has no idea what it takes to launch a successful firm.

• Investors won't trust you with their money since you appear to be a complete amateur.

• Printing NDAs will be a waste of paper because no genuine entrepreneur will ever sign one.

I apologize for missing any cons. Please leave your remarks.

Know why it's important.

The entrepreneur I was meeting with said, "I should be doing crypto, or maybe AI? Aren't those the hot spots? I should look there for a startup idea.”

I shook my head. Yes, they're exciting, but that doesn't mean they're best for you and your business.

“There are different types of entrepreneurs?” he asked.

I said "obviously." Two types, actually. Knowing what type of entrepreneur you are helps you build the right startup.

The two types of businesspeople

The best way for me to describe the two types of entrepreneurs is to start by telling you exactly the kinds of entrepreneurial opportunities I never get excited about: future opportunities.

In the early 1990s, my older brother showed me the World Wide Web and urged me to use it. Unimpressed, I returned to my Super Nintendo.

My roommate tried to get me to join Facebook as a senior in college. I remember thinking, This is dumb. Who'll use it?

In 2011, my best friend tried to convince me to buy bitcoin and I laughed.

Heck, a couple of years ago I had to buy a new car, and I never even considered buying something that didn’t require fossilized dinosaur bones.

I'm no visionary. I don't anticipate the future. I focus on the present.

This tendency makes me a problem-solving entrepreneur. I identify entrepreneurial opportunities by spotting flaws and/or inefficiencies in the world and devising solutions.

There are other ways to find business opportunities. Visionary entrepreneurs also exist. I don't mean visionary in the hyperbolic sense that implies world-changing impact. I mean visionary as an entrepreneur who identifies future technological shifts that will change how people work and live and create new markets.

Problem-solving and visionary entrepreneurs are equally good. But the two approaches to building companies are very different. Knowing the type of entrepreneur you are will help you build a startup that fits your worldview.

What is the distinction?

Let's use some simple hypotheticals to compare problem-solving and visionary entrepreneurship.

Imagine a city office building without nearby restaurants. Those office workers love to eat. Sometimes they'd rather eat out than pack a lunch. As an entrepreneur, you can solve the lack of nearby restaurants. You'd open a restaurant near that office, say a pizza parlor, and get customers because you solved the lack of nearby restaurants. Problem-solving entrepreneurship.

Imagine a new office building in a developing area with no residents or workers. In this scenario, a large office building is coming. The workers will need to eat then. As a visionary entrepreneur, you're excited about the new market and decide to open a pizzeria near the construction to meet demand.

Both possibilities involve the same product. You opened a pizzeria. How you launched that pizza restaurant and what will affect its success are different.

Why is the distinction important?

Let's say you opened a pizzeria near an office. You'll probably get customers. Because people are nearby and demand isn't being met, someone from a nearby building will stop in within the first few days of your pizzeria's grand opening. This makes solving the problem relatively risk-free. You'll get customers unless you're a fool.

The market you're targeting existed before you entered it, so you're not guaranteed success. This means people in that market solved the lack of nearby restaurants. Those office workers are used to bringing their own lunches. Why should your restaurant change their habits? Even when they eat out, they're used to traveling far. They've likely developed pizza preferences.

To be successful with your problem-solving startup, you must convince consumers to change their behavior, which is difficult.

Unlike opening a pizza restaurant near a construction site. Once the building opens, workers won't have many preferences or standardized food-getting practices. Your pizza restaurant can become the incumbent quickly. You'll be the first restaurant in the area, so you'll gain a devoted following that makes your food a routine.

Great, right? It's easier than changing people's behavior. The benefit comes with a risk. Opening a pizza restaurant near a construction site increases future risk. What if builders run out of money? No one moves in? What if the building's occupants are the National Association of Pizza Haters? Then you've opened a pizza restaurant next to pizza haters.

Which kind of businessperson are you?

This isn't to say one type of entrepreneur is better than another. Each type of entrepreneurship requires different skills.

As my simple examples show, a problem-solving entrepreneur must operate in markets with established behaviors and habits. To be successful, you must be able to teach a market a new way of doing things.

Conversely, the challenge of being a visionary entrepreneur is that you have to be good at predicting the future and getting in front of that future before other people.

Both are difficult in different ways. So, smart entrepreneurs don't just chase opportunities. Smart entrepreneurs pursue opportunities that match their skill sets.

https://tomconnor.me/wp-content/uploads/2021/08/10x-Engineer-Mental-Models.pdf

I keep returning to the same mental models and tricks after writing and reading about a wide range of topics.

Top 12 mental models

12.

Survival bias - We perceive the surviving population as remarkable, yet they may have gotten there through sheer grit.

Survivorship bias affects us in many situations. Our retirement fund; the unicorn business; the winning team. We often study and imitate the last one standing. This can lead to genuine insights and performance improvements, but it can also lead us astray because the leader may just be lucky.

11.

The Helsinki Bus Theory - How to persevere Buss up!

Always display new work, and always be compared to others. Why? Easy. Keep riding. Stay on the fucking bus.

10.

Until it sticks… Turning up every day… — Artists teach engineers plenty. Quality work over a career comes from showing up every day and starting.

9.

WRAP decision making process (Heath Brothers)

Decision-making WRAP Model:

W — Widen your Options

R — Reality test your assumptions

A — Attain Distance

P — Prepare to be wrong or Right

8.

Systems for knowledge worker excellence - Todd Henry and Cal Newport write about techniques knowledge workers can employ to build a creative rhythm and do better work.

Todd Henry's FRESH framework:

1. Focus: Keep the start in mind as you wrap up.

2. Relationships: close a loop that's open.

3. Pruning is an energy.

4. Set aside time to be inspired by stimuli.

5. Hours: Spend time thinking.

7.

Black Box Thinking…..

BBT is learning from mistakes. Science has transformed the world because it constantly updates its theories in light of failures. Complexity guarantees failure. Do we learn or self-justify?

6.

The OODA Loop - Competitive advantage

O: Observe: collect the data. Figure out exactly where you are, what’s happening.

O: Orient: analyze/synthesize the data to form an accurate picture.

D: Decide: select an action from possible options

A: Action: execute the action, and return to step (1)

Boyd's approach indicates that speed and agility are about information processing, not physical reactions. They form feedback loops. More OODA loops improve speed.

5.

Know your Domain 

Leaders who try to impose order in a complex situation fail; those who set the stage, step back, and allow patterns to develop win.

https://vimeo.com/640941172?embedded=true&source=vimeo_logo&owner=11999906

4.

The Three Critical Gaps

• Information Gap - The discrepancy between what we know and what we would like to know

• Gap in Alignment - What individuals actually do as opposed to what we wish them to do

• Effects Gap - the discrepancy between our expectations and the results of our actions

3.

Theory of Constraints — The Goal  - To maximize system production, maximize bottleneck throughput.

• Goldratt creates a five-step procedure:

1. Determine the restriction

2. Improve the restriction.

3. Everything else should be based on the limitation.

4. Increase the restriction

5. Go back to step 1 Avoid letting inertia become a limitation.

Any non-constraint improvement is an illusion.

2.

Serendipity and the Adjacent Possible - Why do several amazing ideas emerge at once? How can you foster serendipity in your work?

You need specialized abilities to reach to the edge of possibilities, where you can pursue exciting tasks that will change the world. Few people do it since it takes a lot of hard work. You'll stand out if you do.

Most people simply lack the comfort with discomfort required to tackle really hard things. At some point, in other words, there’s no way getting around the necessity to clear your calendar, shut down your phone, and spend several hard days trying to make sense of the damn proof.

1.

Boundaries of failure - Rasmussen's accident model.

Rasmussen modeled this. It has economic, workload, and performance boundaries.

The economic boundary is a company's profit zone. If the lights are on, you're within the economic boundaries, but there's pressure to cut costs and do more.

Performance limit reflects system capacity. Taking shortcuts is a human desire to minimize work. This is often necessary to survive because there's always more labor.

Both push operating points toward acceptable performance. Personal or process safety, or equipment performance.

If you exceed acceptable performance, you'll push back, typically forcefully.