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.

Reflections on the closed company Hola! Dating app

I'll discuss my fuckups as an entrepreneur and CEO. All of them refer to the dating app Hola!, which I co-founded and starred in.

Spring 2021 was when we started. Two techies and two non-techies created a dating app. Pokemon Go and Tinder were combined.

Online dating is a business, and it takes two weeks from a like to a date. We questioned online dating app users if they met anyone offline last year.

75% replied yes, 50% sometimes, 25% usually.

Offline dating is popular, yet people have concerns.

• Men are reluctant to make mistakes in front of others.

• Women are curious about the background of everyone who approaches them.

We designed unique mechanics that let people date after a match. No endless chitchat. Women would be safe while men felt like cowboys.

I wish to emphasize three faults that lead to founders' estrangement.

This detachment ultimately led to us shutting down the company.

The wrong technology stack

Situation

Instead of generating a faster MVP and designing an app in a universal stack for iOS and Android, I argued we should pilot the app separately for iOS and Android. Technical founders' expertise made this possible.

Self-reflection

Mistaken strategy. We lost time and resources developing two apps at once. We chose iOS since it's more profitable. Apple took us out after the release, citing Guideline 4.3 Spam. After 4 months, we had nothing. We had a long way to go to get the app on Android and the Store.

I suggested creating a uniform platform for the company's growth. This makes parallel product development easier. The strategist's lack of experience and knowledge made it a piece of crap.

What would I have changed if I could?

We should have designed an Android universal stack. I expected Apple to have issues with a dating app.

Our approach should have been to launch something and subsequently improve it, but prejudice won.

The lesson

Discuss the IT stack with your CTO. It saves time and money. Choose the easiest MVP method.

2. A tardy search for investments

Situation

Though the universe and other founders encouraged me to locate investors first, I started pitching when we almost had an app.

When angels arrived, it was time to close. The app was banned, war broke out, I left the country, and the other co-founders stayed. We had no savings.

Self-reflection

I loved interviewing users. I'm proud of having done 1,000 interviews. I wanted to understand people's pain points and improve the product.

Interview results no longer affected the product. I was terrified to start pitching. I filled out accelerator applications and redid my presentation. You must go through that so you won't be terrified later.

What would I have changed if I could?

Get an external or internal mentor to help me with my first pitch as soon as possible. I'd be supported if criticized. He'd cheer with me if there was enthusiasm.

In 99% of cases, I'm comfortable jumping into the unknown, but there are exceptions. The mentor's encouragement would have prompted me to act sooner.

The lesson

Begin fundraising immediately. Months may pass. Show investors your pre-MVP project. Draw inferences from feedback.

3. Role ambiguity

Situation

My technical co-founders were also part-time lead developers, which produced communication issues. As co-founders, we communicated well and recognized the problems. Stakes, vesting, target markets, and approach were agreed upon.

We were behind schedule. Technical debt and strategic gap grew.

Bi-daily and weekly reviews didn't help. Each time, there were explanations. Inside, I was freaking out.

Self-reflection

I am a fairly easy person to talk to. I always try to stick to agreements; otherwise, my head gets stuffed with unnecessary information, interpretations, and emotions.

Sit down -> talk -> decide -> do -> evaluate the results. Repeat it.

If I don't get detailed comments, I start ruining everyone's mood. If there's a systematic violation of agreements without a good justification, I won't join the project or I'll end the collaboration.

What would I have done otherwise?

This is where it’s scariest to draw conclusions. Probably the most logical thing would have been not to start the project as we started it. But that was already a completely different project. So I would not have done anything differently and would have failed again.

But I drew conclusions for the future.

The lesson

First-time founders should find an adviser or team coach for a strategic session. It helps split the roles and responsibilities.

It’s Zuora’s, and it’s brilliant. Here’s why.

My friend Tim got a sales position at a Series-C software company that garnered $60 million from A-list investors. He's one of the best salespeople I know, yet he emailed me after starting to struggle.

Tim has a few modest clients. “Big companies ignore my pitch”. Tim said.

I love helping teams write the strategic story that drives sales, marketing, and fundraising. Tim and I had lunch at Amber India on Market Street to evaluate his deck.

After a feast, I asked Tim when prospects tune out.

He said, “several slides in”.

Intent on maximizing dining ROI, Tim went back to the buffet for seconds. When he returned, I pulled out my laptop and launched into a Powerpoint presentation.

“What’s this?” Tim asked.

“This,” I said, “is the greatest sales deck I have ever seen.”

Five Essentials of a Great Sales Narrative

I showed Tim a sales slide from IPO-bound Zuora, which sells a SaaS platform for subscription billing. Zuora supports recurring payments (e.g. enterprise software).

Ex-Zuora salesman gave me the deck, saying it helped him close his largest business. (I don't know anyone who works at Zuora.) After reading this, a few Zuora employees contacted me.)

Tim abandoned his naan in a pool of goat curry and took notes while we discussed the Zuora deck.

We remarked how well the deck led prospects through five elements:

(The ex-Zuora salesperson begged me not to release the Zuora deck publicly.) All of the images below originate from Zuora's website and SlideShare channel.)

#1. Name a Significant Change in the World

Don't start a sales presentation with mentioning your product, headquarters, investors, clients, or yourself.

Name the world shift that raises enormous stakes and urgency for your prospect.

Every Zuora sales deck begins with this slide:

Zuora coined the term subscription economy to describe a new market where purchasers prefer regular service payments over outright purchases. Zuora then shows a slide with the change's history.

Most pitch recommendation advises starting with the problem. When you claim a problem, you put prospects on the defensive. They may be unaware of or uncomfortable admitting the situation.

When you highlight a global trend, prospects open up about how it affects them, worries them, and where they see opportunity. You capture their interest. Robert McKee says:

…what attracts human attention is change. …if the temperature around you changes, if the phone rings — that gets your attention. The way in which a story begins is a starting event that creates a moment of change.

#2. Show There’ll Be Winners and Losers

Loss aversion affects all prospects. They avoid a loss by sticking with the status quo rather than risking a gain by changing.

To fight loss aversion, show how the change will create winners and losers. You must show both

1. that if the prospect can adjust to the modification you mentioned, the outcome will probably be quite favorable; and

2. That failing to do so is likely to have an unacceptable negative impact on the prospect's future

Zuora shows a mass extinction among Fortune 500 firms.

…and then showing how the “winners” have shifted from product ownership to subscription services. Those include upstarts…

…as well as rejuvenated incumbents:

To illustrate, Zuora asks:

Winners utilize Zuora's subscription service models.

#3. Tease the Promised Land

It's tempting to get into product or service details now. Resist that urge.

Prospects won't understand why product/service details are crucial if you introduce them too soon, therefore they'll tune out.

Instead, providing a teaser image of the happily-ever-after your product/service will assist the prospect reach.

Your Promised Land should be appealing and hard to achieve without support. Otherwise, why does your company exist?

Zuora shows this Promised Land slide after explaining that the subscription economy will have winners and losers.

Not your product or service, but a new future state.

(I asked my friend Tim to describe his Promised Land, and he answered, "You’ll have the most innovative platform for ____." Nope: the Promised Land isn't possessing your technology, but living with it.)

Your Promised Land helps prospects market your solution to coworkers after your sales meeting. Your coworkers will wonder what you do without you. Your prospects are more likely to provide a persuasive answer with a captivating Promised Land.

#4. Present Features as “Mystic Gifts” for Overcoming Difficulties on the Road to the Promised Land

Successful sales decks follow the same format as epic films and fairy tales. Obi Wan gives Luke a lightsaber to help him destroy the Empire. You're Gandalf, helping Frodo destroy the ring. Your prospect is Cinderella, and you're her fairy godmother.

Position your product or service's skills as mystical gifts to aid your main character (prospect) achieve the Promised Land.

Zuora's client record slide is shown above. Without context, even the most technical prospect would be bored.

Positioned in the context of shifting from an “old” to a “new world”, it's the foundation for a compelling conversation with prospects—technical and otherwise—about why traditional solutions can't reach the Promised Land.

#5. Show Proof That You Can Make the Story True.

In this sense, you're promising possibilities that if they follow you, they'll reach the Promised Land.

The journey to the Promised Land is by definition rocky, so prospects are right to be cautious. The final part of the pitch is proof that you can make the story come true.

The most convincing proof is a success story about how you assisted someone comparable to the prospect. Zuora's sales people use a deck of customer success stories, but this one gets the essence.

I particularly appreciate this one from an NCR exec (a Zuora customer), which relates more strongly to Zuora's Promised Land:

Not enough successful customers? Product demos are the next best evidence, but features should always be presented in the context of helping a prospect achieve the Promised Land.

The best sales narrative is one that is told by everyone.

Success rarely comes from a fantastic deck alone. To be effective, salespeople need an organization-wide story about change, Promised Land, and Magic Gifts.

Zuora exemplifies this. If you hear a Zuora executive, including CEO Tien Tzuo, talk, you'll likely hear about the subscription economy and its winners and losers. This is the theme of the company's marketing communications, campaigns, and vision statement.

According to the ex-Zuora salesperson, company-wide story alignment made him successful.

The Zuora marketing folks ran campaigns and branding around this shift to the subscription economy, and [CEO] Tien [Tzuo] talked it up all the time. All of that was like air cover for my in-person sales ground attack. By the time I arrived, prospects were already convinced they had to act. It was the closest thing I’ve ever experienced to sales nirvana.

The largest deal ever

Tim contacted me three weeks after our lunch to tell me that prospects at large organizations were responding well to his new deck, which we modeled on Zuora's framework. First, prospects revealed their obstacles more quickly. The new pitch engages CFOs and other top gatekeepers better, he said.

A week later, Tim emailed that he'd signed his company's biggest agreement.

Next week, we’re headed back to Amber India to celebrate.

Successful workers don't talk this way.

"I know it's unprofessional, but I can't stop." — Author Sandy Hall

Do you realize your unprofessionalism? Do you care? Self-awareness?

Everyone can improve their unprofessionalism. Some workplace phrases and words shouldn't be said.

People often say out loud what they're thinking. They show insecurity, incompetence, and disrespect.

"Think before you speak," goes the saying.

Some of these phrases are "okay" in certain situations, but you'll lose colleagues' respect if you use them often.

Your word choice. Your tone. Your intentions. They matter.

Choose your words carefully to build work relationships and earn peer respect. You should build positive relationships with coworkers and clients.

These 10 phrases are unprofessional. 

1. That Meeting Really Sucked

Wow! Were you there? You should be responsible if you attended. You can influence every conversation.

Alternatives

Improve the meeting instead of complaining afterward. Make it more meaningful and productive.

2. Not Sure if You Saw My Last Email

Referencing a previous email irritates people. Email follow-up can be difficult. Most people get tons of emails a day, so it may have been buried, forgotten, or low priority.

Alternatives

It's okay to follow up, but be direct, short, and let the recipient "save face"

3. Any Phrase About Sex, Politics, and Religion

Discussing sex, politics, and religion at work is foolish. If you discuss these topics, you could face harassment lawsuits.

Alternatives

Keep quiet about these contentious issues. Don't touch them.

4. I Know What I’m Talking About

Adding this won't persuade others. Research, facts, and topic mastery are key to persuasion. If you're knowledgeable, you don't need to say this.

Alternatives

Please don’t say it at all. Justify your knowledge.

5. Per Our Conversation

This phrase sounds like legal language. You seem to be documenting something legally. Cold, stern, and distant. "As discussed" sounds inauthentic.

Alternatives

It was great talking with you earlier; here's what I said.

6. Curse-Word Phrases

Swearing at work is unprofessional. You never know who's listening, so be careful. A child may be at work or on a Zoom or Teams call. Workplace cursing is unacceptable.

Alternatives

Avoid adult-only words.

7. I Hope This Email Finds You Well

This is a unique way to wish someone well. This phrase isn't as sincere as the traditional one. When you talk about the email, you're impersonal.

Alternatives

Genuinely care for others.

8. I Am Really Stressed

Happy, strong, stress-managing coworkers are valued. Manage your own stress. Exercise, sleep, and eat better.

Alternatives

Everyone has stress, so manage it. Don't talk about your stress.

9. I Have Too Much to Do

You seem incompetent. People think you can't say "no" or have poor time management. If you use this phrase, you're telling others you may need to change careers.

Alternatives

Don't complain about your workload; just manage it.

10. Bad Closing Salutations

"Warmly," "best," "regards," and "warm wishes" are common email closings. This conclusion sounds impersonal. Why use "warmly" for finance's payment status?

Alternatives

Personalize the closing greeting to the message and recipient. Use "see you tomorrow" or "talk soon" as closings.

Bringing It All Together

These 10 phrases are unprofessional at work. That meeting sucked, not sure if you saw my last email, and sex, politics, and religion phrases.

Also, "I know what I'm talking about" and any curse words. Also, avoid phrases like I hope this email finds you well, I'm stressed, and I have too much to do.

Successful workers communicate positively and foster professionalism. Don't waste chances to build strong work relationships by being unprofessional.

“Unprofessionalism damages the business reputation and tarnishes the trust of society.” — Pearl Zhu, an American author

This post is a summary. Read full article here

How to reframe irritation and go forward

“… before you can figure out where you are going, you need to know where you are, and once you know and accept where you are, you can design your way to where you want to be.” — Bill Burnett and Dave Evans

“You’ve been here before. But there are some new ingredients this time. What can tell yourself that will make you understand that now isn’t just like last year? That there’s something new in this August.”

My coach paused. I sighed, inhaled deeply, and considered her question.

What could I say? I simply needed a plan from her so everything would fall into place and I could be the happy, successful person I want to be.

Time passed. My mind was exhausted from running all morning, all summer, or the last five years, searching for what to do next and how to get there.

Calmer, I remembered that my coach's inquiry had benefited me throughout the summer. The month before our call, I read Designing Your Work Life — How to Thrive and Change and Find Happiness at Work from Standford University’s Bill Burnett and Dave Evans.

A passage in their book felt like a lifeline: “We have something important to say to you: Wherever you are in your work life, whatever job you are doing, it’s good enough. For now. Not forever. For now.”

As I remembered this book on the coaching call, I wondered if I could embrace where I am in August and say my job life is good enough for now. Only temporarily.

I've done that since. I'm getting unstuck.

Here's how you can take the first step in any area where you feel stuck.

How to acquire the perspective of "Good enough for now" for yourself

We’ve all heard the advice to just make the best of a bad situation. That´s not bad advice, but if you only make the best of a bad situation, you are still in a bad situation. It doesn’t get to the root of the problem or offer an opportunity to change the situation. You’re more cheerfully navigating lousiness, which is an improvement, but not much of one and rather hard to sustain over time.” — Bill Burnett and Dave Evans

Reframing Burnett at Evans says good enough for now is the key to being happier at work. Because, as they write, a designer always has options.

Choosing to believe things are good enough for now is liberating. It helps us feel less victimized and less judged. Accepting our situation helps us become unstuck.

Let's break down the process, which designers call constructing your way ahead, into steps you can take today.

Writing helps get started. First, write down your challenge and why it's essential to you. If pen and paper help, try this strategy:

• Make the decision to accept the circumstance as it is. Designers always begin by acknowledging the truth of the situation. You now refrain from passing judgment. Instead, you simply describe the situation as accurately as you can. This frees us from negative thought patterns that prevent us from seeing the big picture and instead keep us in a tunnel of negativity.

• Look for a reframing right now. Begin with good enough for the moment. Take note of how your body feels as a result. Tell yourself repeatedly that whatever is occurring is sufficient for the time being. Not always, but just now. If you want to, you can even put it in writing and repeatedly breathe it in, almost like a mantra.

• You can select a reframe that is more relevant to your situation once you've decided that you're good enough for now and have allowed yourself to believe it. Try to find another perspective that is possible, for instance, if you feel unappreciated at work and your perspective of I need to use and be recognized for all my new skills in my job is making you sad and making you want to resign. For instance, I can learn from others at work and occasionally put my new abilities to use.

• After that, leave your mind and act in accordance with your new perspective. Utilize the designer's bias for action to test something out and create a prototype that you can learn from. Your beginning point for creating experiences that will support the new viewpoint derived from the aforementioned point is the new perspective itself. By doing this, you recognize a circumstance at work where you can provide value to yourself or your workplace and then take appropriate action. Send two or three coworkers from whom you wish to learn anything an email, for instance, asking them to get together for coffee or a talk.

Choose tiny, doable actions. You prioritize them at work.

Let's assume you're feeling disconnected at work, so you make a list of folks you may visit each morning or invite to lunch. If you're feeling unmotivated and tired, take a daily walk and treat yourself to a decent coffee.

This may be plenty for now. If you want to take this procedure further, use Burnett and Evans' internet tools and frameworks.

Developing the daily practice of reframing

“We’re not discontented kids in the backseat of the family minivan, but how many of us live our lives, especially our work lives, as if we are?” — Bill Burnett and Dave Evans

I choose the good enough for me perspective every day, often. No quick fix. Am a failing? Maybe a little bit, but I like to think of it more as building muscle.

This way, every time I tell myself it's ok, I hear you. For now, that muscle gets stronger.

Hopefully, reframing will become so natural for us that it will become a habit, and not a technique anymore.

If you feel like you’re stuck in your career or at work, the reframe of Good enough, for now, might be valuable, so just go ahead and try it out right now.

And while you’re playing with this, why not think of other areas of your life too, like your relationships, where you live — even your writing, and see if you can feel a shift?