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.

New ventures are exciting. It's fun to imagine yourself rich, successful, and famous (if that's your thing). How you'll help others and make your family proud. This excitement can pull you forward for years, even when you intuitively realize that the path you're on may not lead to your desired success.

Know when to change course. Switching course can mean pivoting or changing direction.

In this not-so-short blog, I'll describe the journey of building your dream. And how the journey might look when you think you're building your dream, but fall short of that vision. Both can feel similar in the beginning, but there are subtle differences.

Let’s dive in.

How an exciting journey to a dead end looks and feels.

You want to help many people. You're business-minded, creative, and ambitious. You jump into entrepreneurship. You're excited, free, and in control.

I'll use tech as an example because that's what I know best, but this applies to any entrepreneurial endeavor.

So you start learning the basics of your field, say coding/software development. You read books, take courses, and may even join a bootcamp. You start practicing, and the journey begins. Once you reach a certain level of skill (which can take months, usually 12-24), you gain the confidence to speak with others in the field and find common ground. You might attract a co-founder this way with time. You and this person embark on a journey (Tip: the idea you start with is rarely the idea you end with).

Amateur mistake #1: You spend months building a product before speaking to customers.

Building something pulls you forward blindly. You make mistakes, avoid customers, and build with your co-founder or small team in the dark for months, usually 6-12 months.

You're excited when the product launches. We'll be billionaires! The market won't believe it. This excites you and the team. Launch.

….

Nothing happens.

Some people may sign up out of pity, only to never use the product or service again.

You and the team are confused, discouraged and in denial. They don't get what we've built yet. We need to market it better, we need to talk to more investors, someone will understand our vision.

This is a hopeless path, and your denial could last another 6 months. If you're lucky, while talking to consumers and investors (which you should have done from the start), someone who has been there before would pity you and give you an idea to pivot into that can create income.

Suppose you get this idea and pivot your business. Again, you've just pivoted into something limited by what you've already built. It may be a revenue-generating idea, but it's rarely new. Now you're playing catch-up, doing something others are doing but you can do better. (Tip #2: Don't be late.) Your chances of winning are slim, and you'll likely never catch up.

You're finally seeing revenue and feel successful. You can compete, but if you're not a first mover, you won't earn enough over time. You'll get by or work harder than ever to earn what a skilled trade could provide. You didn't go into business to stress out and make $100,000 or $200,000 a year. When you can make the same amount by becoming a great software developer, electrician, etc.

You become stuck. Either your firm continues this way for years until you realize there isn't enough growth to recruit a strong team and remove yourself from day-to-day operations due to competition. Or a catastrophic economic event forces you to admit that what you were building wasn't new and unique and wouldn't get you where you wanted to be.

This realization could take 6-10 years. No kidding.

The good news is, you’ve learned a lot along the way and this information can be used towards your next venture (if you have the energy).

Key Lesson: Don’t build something if you aren’t one of the first in the space building it just for the sake of building something.

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Let's discuss what it's like to build something that can make your dream come true.

Case 2: Building something the market loves is difficult but rewarding.

It starts with a problem that hasn't been adequately solved for a long time but is now solvable due to technology. Or a new problem due to a change in how things are done.

Let's examine each example.

Example #1: Mass communication. The problem is now solvable due to some technological breakthrough.

Twitter — One of the first web 2 companies that became successful with the rise of smart mobile computing.

People can share their real-time activities via mobile device with friends, family, and strangers. Web 2 and smartphones made it easy and fun.

Example #2: A new problem has emerged due to some change in the way things are conducted.

Zoom- A web-conferencing company that reached massive success due to the movement towards “work from home”, remote/hybrid work forces.

Online web conferencing allows for face-to-face communication.

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These two examples show how to build a unicorn-type company. It's a mix of solving the right problem at the right time, either through a technological breakthrough that opens up new opportunities or by fundamentally changing how people do things.

Let's find these opportunities.

Start by examining problems, such as how the world has changed and how we can help it adapt. It can also be both. Start team brainstorming. Research technologies, current world-trends, use common sense, and make a list. Then, choose the top 3 that you're most excited about and seem most workable based on your skillsets, values, and passion.

Once you have this list, create the simplest MVP you can and test it with customers. The prototype can be as simple as a picture or diagram of user flow and end-user value. No coding required. Market-test. Twitter's version 1 was simple. It was a web form that asked, "What are you doing?" Then publish it from your phone. A global status update, wherever you are. Currently, this company has a $50 billion market cap.

Here's their MVP screenshot.

Small things grow. Tiny. Simplify.

Remember Frequency and Value when brainstorming. Your product is high frequency (Twitter, Instagram, Snapchat, TikTok) or high value (Airbnb for renting travel accommodations), or both (Gmail).

Once you've identified product ideas that meet the above criteria, they're simple, have a high frequency of use, or provide deep value. You then bring it to market in the simplest, most cost-effective way. You can sell a half-working prototype with imagination and sales skills. You need just enough of a prototype to convey your vision to a user or customer.

With this, you can approach real people. This will do one of three things: give you a green light to continue on your vision as is, show you that there is no opportunity and people won't use it, or point you in a direction that is a blend of what you've come up with and what the customer / user really wants, and you update the prototype and go back to the maze. Repeat until you have enough yeses and conviction to build an MVP.

I've worked in a People role at seven early-stage firms for over 15 years (I enjoy chasing a dream!). Few of the seven achieved profitability, including unicorn status or acquisition.

Did early-stage startups share anything? Was there a difference between winners and losers? YES.

I support founders and entrepreneurs building financially sustainable enterprises with a compelling cause. This isn't something everyone would do. A company's success demands more than guts. Founders drive startup success.

Six Qualities of Successful Startups

Successful startup founders either innately grasped the correlation between strong team engagement and a well-executed business model, or they knew how to ask and listen to others (executive coaches, other company leaders, the team itself) to learn about it.

Successful startups:

1. Co-founders agreed and got along personally.

Multi-founder startups are common. When co-founders agree on strategic decisions and are buddies, there's less friction and politics at work.

As a co-founder, ask your team if you're aligned. They'll explain.

I've seen C-level leaders harbor personal resentments over disagreements. A co-departure founder's caused volatile leadership and work disruptions that the team struggled to manage during and after.

2. Team stayed.

Successful startups have low turnover. Nobody is leaving. There may be a termination for performance, but other team members will have observed the issues and agreed with the decision.

You don't want organizational turnover of 30%+, with leaders citing performance issues but the team not believing them. This breeds suspicion.

Something is wrong if many employees leave voluntarily or involuntarily. You may hear about lack of empowerment, support, or toxic leadership in exit interviews and from the existing team. Intellectual capital loss and resource instability harm success.

3. Team momentum.

A successful startup's team is excited about its progress. Consistently achieving goals and having trackable performance metrics. Some describe this period of productivity as magical, with great talents joining the team and the right people in the right places. Increasing momentum.

I've also seen short-sighted decisions where only some departments, like sales and engineering, had goals. Lack of a unified goals system created silos and miscommunication. Some employees felt apathetic because they didn't know how they contributed to team goals.

4. Employees advanced in their careers.

Even if you haven't created career pathing or professional development programs, early-stage employees will grow and move into next-level roles. If you hire more experienced talent and leaders, expect them to mentor existing team members. Growing companies need good performers.

New talent shouldn't replace and discard existing talent. This creates animosity and makes existing employees feel unappreciated for their early contributions to the company.

5. The company lived its values.

Culture and identity are built on lived values. A company's values affect hiring, performance management, rewards, and other processes. Identify, practice, and believe in company values. Starting with team values instead of management or consultants helps achieve this. When a company's words and actions match, it builds trust.

When company values are beautifully displayed on a wall but few employees understand them, the opposite is true. If an employee can't name the company values, they're useless.

6. Communication was clear.

When necessary information is shared with the team, they feel included, trusted, and like owners. Transparency means employees have the needed information to do their jobs. Disclosure builds trust. The founders answer employees' questions honestly.

Information accessibility decreases office politics. Without transparency, even basic information is guarded and many decisions are made in secret. I've seen founders who don't share financial, board meeting, or compensation and equity information. The founders' lack of trust in the team wasn't surprising, so it was reciprocated.

The Choices

Finally. All six of the above traits (leadership alignment, minimal turnover, momentum, professional advancement, values, and transparency) were high in the profitable startups I've worked at, including unicorn status or acquisition.

I've seen these as the most common and constant signals of startup success or failure.

These characteristics are the product of founders' choices. These decisions lead to increased team engagement and business execution.

Here's something to consider for startup employees and want-to-bes. 90% of startups fail, despite the allure of building something new and gaining ownership. With the emotional and time investment in startup formation, look for startups with these traits to reduce your risk.

Both you and the startup will thrive in these workplaces.

We've all been there: You propose a suggestion to your team at a meeting, and most people appear on board, but a handful or small minority aren't. How can we achieve collective buy-in when we need to go forward but don't know how to deal with some team members' perceived intransigence?

Steps:

1. Investigate the divergent opinions: Begin by sincerely attempting to comprehend the viewpoint of your disagreeing coworkers. Maybe it makes sense to switch horses in the middle of the race. Have you completely overlooked a blind spot, such as a political concern that could arise as an unexpected result of proceeding? This is crucial to ensure that the person or people feel heard as well as to advance the goals of the team. Sometimes all individuals need is a little affirmation before they fully accept your point of view.

• It says a lot about you as a leader to be someone who always lets the perceived greatest idea win, regardless of the originating channel, if after studying and evaluating you see the necessity to align with the divergent position.

• If, after investigation and assessment, you determine that you must adhere to the original strategy, we go to Step 2.

2. Disagree and Commit: Jeff Bezos, CEO of Amazon, has had this experience, and Julie Zhuo describes how he handles it in her book The Making of a Manager.

It's OK to disagree when the team is moving in the right direction, but it's not OK to accidentally or purposefully damage the team's efforts because you disagree. Let the team know your opinion, but then help them achieve company goals even if they disagree. Unknown. You could be wrong in today's ever-changing environment.

So next time you have a team member who seems to be dissenting and you've tried the previous tactics, you may ask the individual in the meeting I understand you but I don't want us to leave without you on board I need your permission to commit to this approach would you give us your commitment?

Consider yourself lucky if your last FAANG interview was rejected.

FAANG—Facebook, Apple, Amazon, Netflix, Google

(I know its manga now, but watch me not care)

These big companies offer many benefits.

1. large salaries and benefits

2. Prestige

3. high expectations for both you and your coworkers.

However, these jobs may have major drawbacks that only become apparent when you're thrown to the wolves, so it's up to you whether you see them as drawbacks or opportunities.

I know most college graduates start working at big tech companies because of their perceived coolness.

I've worked in these companies for years and can tell you what to expect if you get a job here.

Little fish in a vast ocean

The most obvious. Most billion/trillion-dollar companies employ thousands.

You may work on a small, unnoticed product part.

Directors and higher will sometimes make you redo projects they didn't communicate well without respecting your time, talent, or will to work on trivial stuff that doesn't move company needles.

Peers will only say, "Someone has to take out the trash," even though you know company resources are being wasted.

The power imbalance is frustrating.

What you can do about it

Know your WHY. Consider long-term priorities. Though riskier, I stayed in customer-facing teams because I loved building user-facing products.

This increased my impact. However, if you enjoy helping coworkers build products, you may be better suited for an internal team.

I told the Directors and Vice Presidents that their actions could waste Engineering time, even though it was unpopular. Some were receptive, some not.

I kept having tough conversations because they were good for me and the company.

However, some of my coworkers praised my candor but said they'd rather follow the boss.

An outdated piece of technology can take years to update.

Apple introduced Swift for iOS development in 2014. Most large tech companies adopted the new language after five years.

This is frustrating if you want to learn new skills and increase your market value.

Knowing that my lack of Swift practice could hurt me if I changed jobs made writing verbose Objective C painful.

What you can do about it

1. Work on the new technology in side projects; one engineer rewrote the Lyft app in Swift over the course of a weekend and promoted its adoption throughout the entire organization.

2. To integrate new technologies and determine how to combine legacy and modern code, suggest minor changes to the existing codebase.

Most managers spend their entire day in consecutive meetings.

After their last meeting, the last thing they want is another meeting to discuss your career goals.

Sometimes a manager has 15-20 reports, making it hard to communicate your impact.

Misunderstandings and stress can result.

Especially when the manager should focus on selfish parts of the team. Success won't concern them.

What you can do about it

1. Tell your manager that you are a self-starter and that you will pro-actively update them on your progress, especially if they aren't present at the meetings you regularly attend.

2. Keep being proactive and look for mentorship elsewhere if you believe your boss doesn't have enough time to work on your career goals.

3. Alternately, look for a team where the manager has more authority to assist you in making career decisions.

After a certain point, company loyalty can become quite harmful.

Because big tech companies create brand loyalty, too many colleagues stayed in unhealthy environments.

When you work for a well-known company and strangers compliment you, it's fun to tell your friends.

Work defines you. This can make you stay too long even though your career isn't progressing and you're unhappy.

Google may become your surname.

Workplaces are not families.

If you're unhappy, don't stay just because they gave you the paycheck to buy your first home and make you feel like you owe your life to them.

Many employees stayed too long. Though depressed and suicidal.

What you can do about it

1. Your life is not worth a company.

2. Do you want your job title and workplace to be listed on your gravestone? If not, leave if conditions deteriorate.

3. Recognize that change can be challenging. It's difficult to leave a job you've held for a number of years.

4. Ask those who have experienced this change how they handled it.

You still have a bright future if you were rejected from FAANG interviews.

Rejections only lead to amazing opportunities. If you're young and childless, work for a startup.

Companies may pay more than FAANGs. Do your research.

Ask recruiters and hiring managers tough questions about how the company and teams prioritize respectful working hours and boundaries for workers.

I know many 15-year-olds who have a lifelong dream of working at Google, and it saddens me that they're chasing a name on their resume instead of excellence.

This article is not meant to discourage you from working at these companies, but to share my experience about what HR/managers will never mention in interviews.

Read both sides before signing the big offer letter.