Here is the ugly stuff, read this if you have a founder in your life or are trying to become one. Your call.

#1 You'll try to talk yourself to sleep, but it won't always work.

As founders, we're all driven. Good and bad, you're restless. Success requires resistance and discipline. Your startup will be on your mind 24/7, and not everyone will have the patience to listen to your worries, ideas, and coffee runs. You become more self-sufficient than ever before.

#2 No one will understand what you're going through unless they've been a founder.

Some of my closest friends don't understand the work that goes into starting a business, and we can't blame them.

#3 You'll feel alienated.

Your problems aren't common; calling your bestie won't help. You must search hard for the right resources. It alienates you from conversations you no longer relate to. (No 4th of July, no long weekends!)

#4 Since you're your "own boss," people assume you have lots of free time.

Do you agree? I was on a webinar with lots of new entrepreneurs, and one woman said, "I started my own business so I could have more time for myself." This may be true for some lucky people, and you can be flexible with your schedule. If you want your business to succeed, you'll probably be its slave for a while.

#5 No time for illness or family emergencies.

Both last month. Oh, no! Physically and emotionally withdrawing at the worst times will give you perspective. I learned this the hard way because I was too stubborn to postpone an important interview. I thought if I rested all day and only took one call, I'd be fine. Nope. I had a fever and my mind wasn't as sharp, so my performance and audience interaction suffered. Nope. Better to delay than miss out.

Oh, and setting a "OoO" makes you cringe.

#6 Good luck with your mental health, perfectionists.

When building a startup, it's difficult to accept that there won't be enough time to do everything. You can't make them all, not perfectly. You must learn to accept things that are done but not perfect.

#7 As a founder, you'll make mistakes, but you'll want to make them quickly so you can learn.

Hard lessons are learned quicker. You'll need to pivot and try new things often; some won't work, and it's best to discover them sooner rather than later.

#8 Pyramid schemes abound.

I didn't realize how bad it was until I started a company. You must spy and constantly research. As a founder, you'll receive many emails from people claiming to "support" you. Be wary and keep your eyes open. When it's too good to be true. Some "companies" will try to get you to pay for "competitions" to "pitch at events." Don't do it.

#9 Keep your competitor research to a minimum.

Actually, competition is good. It means there's a market for those solutions. However, this can be mentally exhausting too. Learn about their geography and updates, but that's it.

#10 You'll feel guilty taking vacation.

I don't know what to say, but I no longer enjoy watching TV, and that's okay. Pay attention to things that enrich you, bring you joy, and have fun. It boosts creativity.

Being a startup founder may be one of the hardest professional challenges you face, but it's also a great learning experience. Your passion will take you places you never imagined and open doors to opportunities you wouldn't have otherwise. You'll meet amazing people. No regrets, no complaints. It's a roller coaster, but the good days are great.

Miss anything? Comment below

It's ok and even desired to be unprofitable if you're gaining revenue at a reasonable cost and have 100%+ net dollar retention, meaning you never lose customers and expand them. To estimate the acceptable cost of new SaaS revenue, we compare new revenue to operating loss and payback period. If you pay back the customer acquisition cost in 1.5 years and never lose them (100%+ NDR), you're doing well.

To evaluate payback period, we compared new revenue to net operating loss for the last 73 SaaS companies to IPO since October 2017. (55 out of 73). Here's the data. 1/(new revenue/operating loss) equals payback period. New revenue/operating loss equals cost of new revenue.

Payback averages a year. 55 SaaS companies that weren't profitable at IPO got a 1-year payback. Outstanding. If you pay for a customer in a year and never lose them (100%+ NDR), you're establishing a valuable business. The average was 1.3 years, which is within the 1.5-year range.

New revenue costs $0.96 on average. These SaaS companies lost $0.96 every $1 of new revenue last year. Again, impressive. Average new revenue per operating loss was $1.59.

Loss-in-operations definition. Operating loss revenue COGS S&M R&D G&A (technical point: be sure to use the absolute value of operating loss). It's wrong to only consider S&M costs and ignore other business costs. Operating loss and new revenue are measured over one year to eliminate seasonality.

Operating losses are desirable if you never lose a customer and have a quick payback period, especially when SaaS enterprises are valued on ARR. The payback period should be under 1.5 years, the cost of new income < $1, and net dollar retention 100%.

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.

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.

Unleash the power of the Option key ⌥

#1 Open a link in the Private tab first.

Previously, if I needed to open a Safari link in a private window, I would:

• copied the URL with the right click command,

• choose File > New Private Window to open a private window, and

• clicked return after pasting the URL.

I've found a more straightforward way.

Right-clicking a link shows this, right?

Hold option (⌥) for:

Click Open Link in New Private Window while holding.

Finished!

#2. Instead of searching for specific characters, try this

You may use unicode for business or school. Most people Google them when they need them.

That is lengthy!

You can type some special characters just by pressing ⌥ and a key.

For instance

• ⌥+2 -> ™ (Trademark)
• ⌥+0 -> ° (Degree)
• ⌥+G -> © (Copyright)
• ⌥+= -> ≠ (Not equal to)
• ⌥+< -> ≤ (Less than or equal to)
• ⌥+> -> ≥ (Greater then or equal to)
• ⌥+/ -> ÷ (Different symbol for division)

#3 Activate Do Not Disturb silently.

Do Not Disturb when sharing my screen is awkward for me (because people may think Im trying to hide some secret notifications).

Here's another method.

Hold ⌥ and click on Time (at the extreme right on the menu-bar).

Now, DND is activated (secretly!). To turn it off, do it again.

Note: This works only for DND focus.

#4. Resize a window starting from its center

Although this is rarely useful, it is still a hidden trick.

When you resize a window, the opposite edge or corner is used as the pivot, right?

However, if you want to resize it with its center as the pivot, hold while doing so.

#5. Yes, Cut-Paste is available on Macs as well (though it is slightly different).

I call it copy-move rather than cut-paste. This is how it works.

Carry it out.

Choose a file (by clicking on it), then copy it (⌘+C).

Go to a new location on your Mac. Do you use ⌘+V to paste it? However, to move it, press ⌘+⌥+V.

This removes the file from its original location and copies it here. And it works exactly like cut-and-paste on Windows.

#6. Instantly expand all folders

Set your Mac's folders to List view.

Assume you have one folder with multiple subfolders, each of which contains multiple files. And you wanted to look at every single file that was over there.

How would you do?

You're used to clicking the ⌄ glyph near the folder and each subfolder to expand them all, right? Instead, hold down ⌥ while clicking ⌄ on the parent folder.

This is what happens next.

Everything expands.

View/Copy a file's path as an added bonus

If you want to see the path of a file in Finder, select it and hold ⌥, and you'll see it at the bottom for a moment.

To copy its path, right-click on the folder and hold down ⌥ to see this

Click on Copy <"folder name"> as Pathname to do it.

#7 "Save As"

I was irritated by the lack of "Save As" in Pages when I first got a Mac (after 15 years of being a Windows guy).

It was necessary for me to save the file as a new file, in a different location, with a different name, or both.

Unfortunately, I couldn't do it on a Mac.

However, I recently discovered that it appears when you hold ⌥ when in the File menu.

Yay!