What they'll do is scarier.

My acquaintance recently joined a VC-funded startup. Money, equity, and upside possibilities were nice, but he had a nagging dread.

They just secured a $40M round and are hiring like crazy to prepare for their IPO in two years. All signals pointed to this startup's (a B2B IT business in a stable industry) success, and its equity-holding workers wouldn't pass that up.

Five months after starting the work, my friend struggled with leaving. We might overlook the awful culture and long hours at the proper price. This price plus the company's fate and survival abilities sent my friend departing in an unpleasant unplanned resignation before jumping on yet another sinking ship.

This affects founders. This affects VC-backed companies (and all businesses). This affects anyone starting, buying, or running a business.

Here's the under-the-table approach that's draining VC capital, leaving staff terrified (or jobless), founders rattled, and investors upset. How to recognize, solve, and avoid it

The unsettling reality behind door #1

You can't raise money off just your looks, right? If "looks" means your founding team's expertise, then maybe. In my friend's case, the founding team's strong qualifications and track records won over investors before talking figures.

They're hardly the only startup to raise money without a profitable customer acquisition strategy. Another firm raised money for an expensive sleep product because it's eco-friendly. They were off to the races with a few keywords and key players.

Both companies, along with numerous others, elected to invest on product development first. Company A employed all the tech, then courted half their market (they’re a tech marketplace that connects two parties). Company B spent millions on R&D to create a palatable product, then flooded the world with marketing.

My friend is on Company B's financial team, and he's seen where they've gone wrong. It's terrible.

Company A (tech market): Growing? Not quite. To achieve the ambitious expansion they (and their investors) demand, they've poured much of their little capital into salespeople: Cold-calling commission and salary salesmen. Is it working? Considering attrition and companies' dwindling capital, I don't think so.

Company B (green sleep) has been hiring, digital marketing, and opening new stores like crazy. Growing expenses should result in growing revenues and a favorable return on investment; if you grow too rapidly, you may neglect to check that ROI.

Once Company A cut headcount and Company B declared “going concerned”, my friend realized both startups had the same ailment and didn't recognize it.

I shouldn't have to ask a friend to verify a company's cash reserves and profitability to spot a financial problem. It happened anyhow.

The frightening part isn't that investors were willing to invest millions without product-market fit, CAC, or LTV estimates. That's alarming, but not as scary as the fact that startups aren't understanding the problem until VC rounds have dried up.

When they question consultants if their company will be around in 6 months. It’s a red flag. How will they stretch $20M through a 2-year recession with a $3M/month burn rate and no profitability? Alarms go off.

Who's in danger?

In a word, everyone who raised money without a profitable client acquisition strategy or enough resources to ride out dry spells.

Money mismanagement and poor priorities affect every industry (like sinking all your capital into your product, team, or tech, at the expense of probing what customer acquisition really takes and looks like).

This isn't about tech, real estate, or recession-proof luxury products. Fast, cheap, easy money flows into flashy-looking teams with buzzwords, trending industries, and attractive credentials.

If these companies can't show progress or get a profitable CAC, they can't raise more money. They die if they can't raise more money (or slash headcount and find shoestring budget solutions until they solve the real problem).

The kiss of death (and how to avoid it)

If you're running a startup and think raising VC is the answer, pause and evaluate. Do you need the money now?

I'm not saying VC is terrible or has no role. Founders have used it as a Band-Aid for larger, pervasive problems. Venture cash isn't a crutch for recruiting consumers profitably; it's rocket fuel to get you what and who you need.

Pay-to-play isn't a way to throw money at the wall and hope for a return. Pay-to-play works until you run out of money, and if you haven't mastered client acquisition, your cash will diminish quickly.

How can you avoid this bottomless pit? Tips:

• Understand your burn rate

• Keep an eye on your growth or profitability.

• Analyze each and every marketing channel and initiative.

• Make lucrative customer acquisition strategies and satisfied customers your top two priorities. not brand-new products. not stellar hires. avoid the fundraising rollercoaster to save time. If you succeed in these two tasks, investors will approach you with their thirsty offers rather than the other way around, and your cash reserves won't diminish as a result.

Not as much as your grandfather

My family friend always justified expensive, impractical expenditures by saying it was only monopoly money. In business, startups, and especially with money from investors expecting a return, that's not true.

More founders could understand that there isn't always another round if they viewed VC money as their own limited pool. When the well runs dry, you must refill it or save the day.

Venture financing isn't your grandpa's money. A discerning investor has entrusted you with dry powder in the hope that you'll use it wisely, strategically, and thoughtfully. Use it well.

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%.

Writing for readers:

14 years of daily writing.

I post practically everything on social media. I authored hundreds of articles, thousands of tweets, and numerous volumes to almost no one.

Tens of thousands of readers regularly praise me.

I despised writing. I'm stuck now.

I've learned what readers like and what doesn't.

Here are some essential guidelines for writing with impact:

Readers won't understand your work if you can't.

Though obvious, this slipped me up. Share your truths.

Stories engage human brains.

Showing the journey of a person from worm to butterfly inspires the human spirit.

Overthinking hinders powerful writing.

The best ideas come from inner understanding in between thoughts.

Avoid writing to find it. Write.

Writing a masterpiece isn't motivating.

Write for five minutes to simplify. Step-by-step, entertaining, easy steps.

Good writing requires a willingness to make mistakes.

So write loads of garbage that you can edit into a good piece.

Courageous writing.

A courageous story will move readers. Personal experience is best.

Go where few dare.

Templates, outlines, and boundaries help.

Limitations enhance writing.

Excellent writing is straightforward and readable, removing all the unnecessary fat.

Use five words instead of nine.

Use ordinary words instead of uncommon ones.

Readers desire relatability.

Too much perfection will turn it off.

Write to solve an issue if you can't think of anything to write.

Instead, read to inspire. Best authors read.

Every tweet, thread, and novel must have a central idea.

What's its point?

This can make writing confusing.

️ Don't direct your reader.

Readers quit reading. Demonstrate, describe, and relate.

Even if no one responds, have fun. If you hate writing it, the reader will too.

Quick, easy and tasty (and dollops of parenting around food).

My wife and mom are both great mothers. They're super-efficient planners. They soak and ferment food. My 104-year-old grandfather loved fermented foods.

When I'm hungry and need something fast, I waffle to the pantry. Like most people, I like to improvise. I wish I knew these 11 hacks sooner.

1. The world's best pasta sauce only has 3 ingredients.

You watch recipe videos with prepped ingredients. In reality, prepping and washing take time. The food's taste isn't guaranteed. The raw truth at a sublime level is not talked about often.

Sometimes a radical recipe comes along that's so easy and tasty, you're dumbfounded. The Classic Italian Cook Book has a pasta recipe.

One 28-ounce can of whole, peeled tomatoes, one medium peeled onion, and 5 tablespoons of butter. And salt to taste.

Combine everything in a single pot and simmer for 45 minutes, uncovered. Stir occasionally. Toss the onion halves after 45 minutes and pour the sauce over pasta. Finish!

This simple recipe fights our deepest fears.

Salt to taste! Customized to perfection, no frills.

2. Reheating rice with ice. Magical.

Most of the world eats rice. I was raised in south India. My grandfather farmed rice in the Cauvery river delta.

The problem with rice With growing kids, you can't cook just enough. Leftovers are a norm. Microwaves help most people. Ice cubes are the frosting.

Before reheating rice in the microwave, add an ice cube. The ice will steam the rice, making it fluffy and delicious again.

3. Pineapple leaf 

if it comes off easy, it is ripe enough to cut. No rethinking.

My daughter loves pineapples like her dad. One daddy task is cutting them. Sharing immediate results is therapeutic.

Timing the cut has been the most annoying part over the years. The pineapple leaf tip reveals the fruitiness inside. Always loved it.

4. Magic knife words (rolling and curling)

Cutting hand: Roll the blade's back, not its tip, to cut.

Other hand: If you can’t see your finger tips, you can’t cut them. So curl your fingers.

I dislike that schools don't teach financial literacy or cutting skills.

My wife and I used scissors differently for 25 years. We both used the thumb. My index finger, her middle. We googled the difference when I noticed it and laughed. She's right.

This video teaches knifing skills:

5. Best advice about heat

If it's done in the pan, it's overdone on the plate.

This simple advice stands out when we worry about ingredients and proportions.

6. The truth about pasta water

Pasta water should be sea-salty.

Properly seasoning food separates good from great. Salt depends is a good line.

Want delicious pasta? Well, then kind of a lot, to be perfectly honest.

7. Clean as you go

Clean blender as you go by blending water and dish soap.

I find clean as you go easier than clean afterwords. This easy tip is gold.

8. Clean as you go (bis)

Microwave a bowl of water, vinegar, and a toothpick for 5 minutes.

2 cups water, 2 tablespoons vinegar, and a toothpick to prevent overflow.

5-minute microwave. Let the steam work for another 2 minutes. Sponge-off dirt and food. Simple.

9 and 10. Tools,tools, tools

Immersion blender and pressure cooker save time and money.

Narrative: I experienced fatherly pride. My middle-schooler loves science. We discussed boiling. I spoke. Water doesn't need 100°C to boil. She looked confused. 100 degrees assume something. The world around the water is a normal room. Changing water pressure affects its boiling point. This saves energy. Pressure cooker magic.

I captivated her. She's into science and sustainable living.

Whistling is a subliminal form of self-expression when done right. Pressure cookers remind me of simple pleasures.

Your handiness depends on your home tools. Immersion blenders are great for pre- and post-cooking. It eliminates chopping and washing. Second to the dishwasher, in my opinion.

11. One pepper is plenty

A story I share with my daughters.

Once, everyone thought about spice (not spicy). More valuable than silk. One of the three mighty oceans was named after a source country. Columbus sailed the wrong way and found America. The explorer called the natives after reaching his spice destination.

It was pre-internet days. His Google wasn't working.

My younger daughter listens in awe. Strong roots. Image cast. She can contextualize one of the ocean names.

I struggle with spices in daily life. Combinations are mind-boggling. I have more spices than Columbus. Flavor explosion has repercussions. You must closely follow the recipe without guarantees. Best aha. Double down on one spice and move on. If you like it, it's great.

I naturally gravitate towards cumin soups, fennel dishes, mint rice, oregano pasta, basil thai curry and cardamom pudding.

Variety enhances life. Each of my dishes is unique.

To each their own comfort food and nostalgic memories.

Happy living!

While we played checkers, we thought billionaires played 3D chess. They're playing the same game on a fancier board.

Every medium has nuances and norms. Texting is authentic and casual. A smaller circle has access, creating intimacy and immediacy. Most people read all their texts, but not all their email and mail. Many of us no longer listen to our voicemails, and calling your kids ages you.

Live interviews and testimony under oath inspire real moments, rare in a world where communications departments sanitize everything powerful people say. When (some of) Elon's text messages became public in Twitter v. Musk, we got a glimpse into tech power. It's bowels.

These texts illuminate the tech community's upper caste.

Checkers, Not Chess

Elon texts with Larry Ellison, Joe Rogan, Sam Bankman-Fried, Satya Nadella, and Jack Dorsey. They reveal astounding logic, prose, and discourse. The world's richest man and his followers are unsophisticated, obtuse, and petty. Possibly. While we played checkers, we thought billionaires played 3D chess. They're playing the same game on a fancier board.

They fumble with their computers.

They lean on others to get jobs for their kids (no surprise).

No matter how rich, they always could use more (money).

Differences A social hierarchy exists. Among this circle, the currency of deference is... currency. Money increases sycophantry. Oculus and Elon's "friends'" texts induce nausea.

Autocorrect frustrates everyone.

Elon doesn't stand out to me in these texts; he comes off mostly OK in my view. It’s the people around him. It seems our idolatry of innovators has infected the uber-wealthy, giving them an uncontrollable urge to kill the cool kid for a seat at his cafeteria table. "I'd grenade for you." If someone says this and they're not fighting you, they're a fan, not a friend.

Many powerful people are undone by their fake friends. Facilitators, not well-wishers. When Elon-Twitter started, I wrote about power. Unchecked power is intoxicating. This is a scientific fact, not a thesis. Power causes us to downplay risk, magnify rewards, and act on instincts more quickly. You lose self-control and must rely on others.

You'd hope the world's richest person has advisers who push back when necessary (i.e., not yes men). Elon's reckless, childish behavior and these texts show there is no truth-teller. I found just one pushback in the 151-page document. It came from Twitter CEO Parag Agrawal, who, in response to Elon’s unhelpful “Is Twitter dying?” tweet, let Elon know what he thought: It was unhelpful. Elon’s response? A childish, terse insult.

Scale

The texts are mostly unremarkable. There are some, however, that do remind us the (super-)rich are different. Specifically, the discussions of possible equity investments from crypto-billionaire Sam Bankman-Fried (“Does he have huge amounts of money?”) and this exchange with Larry Ellison:

Ellison, who co-founded $175 billion Oracle, is wealthy. Less clear is whether he can text a billion dollars. Who hasn't been texted $1 billion? Ellison offered 8,000 times the median American's net worth, enough to buy 3,000 Ferraris or the Chicago Blackhawks. It's a bedrock principle of capitalism to have incredibly successful people who are exponentially wealthier than the rest of us. It creates an incentive structure that inspires productivity and prosperity. When people offer billions over text to help a billionaire's vanity project in a country where 1 in 5 children are food insecure, isn't America messed up?

Elon's Morgan Stanley banker, Michael Grimes, tells him that Web3 ventures investor Bankman-Fried can invest $5 billion in the deal: “could do $5bn if everything vision lock... Believes in your mission." The message bothers Elon. In Elon's world, $5 billion doesn't warrant a worded response. $5 billion is more than many small nations' GDP, twice the SEC budget, and five times the NRC budget.

If income inequality worries you after reading this, trust your gut.

Billionaires aren't like the rich.

As an entrepreneur, academic, and investor, I've met modest-income people, rich people, and billionaires. Rich people seem different to me. They're smarter and harder working than most Americans. Monty Burns from The Simpsons is a cartoon about rich people. Rich people have character and know how to make friends. Success requires supporters.

I've never noticed a talent or intelligence gap between wealthy and ultra-wealthy people. Conflating talent and luck infects the tech elite. Timing is more important than incremental intelligence when going from millions to hundreds of millions or billions. Proof? Elon's texting. Any man who electrifies the auto industry and lands two rockets on barges is a genius. His mega-billions come from a well-regulated capital market, enforceable contracts, thousands of workers, and billions of dollars in government subsidies, including a $465 million DOE loan that allowed Tesla to produce the Model S. So, is Mr. Musk a genius or an impressive man in a unique time and place?

The Point

Elon's texts taught us more? He can't "fix" Twitter. For two weeks in April, he was all in on blockchain Twitter, brainstorming Dogecoin payments for tweets with his brother — i.e., paid speech — while telling Twitter's board he was going to make a hostile tender offer. Kimbal approved. By May, he was over crypto and "laborious blockchain debates." (Mood.)

Elon asked the Twitter CEO for "an update from the Twitter engineering team" No record shows if he got the meeting. It doesn't "fix" Twitter either. And this is Elon's problem. He's a grown-up child with all the toys and no boundaries. His yes-men encourage his most facile thoughts, and shitposts and errant behavior diminish his genius and ours.

Post-Apocalyptic

The universe's titans have a sense of humor.

Every day, we must ask: Who keeps me real? Who will disagree with me? Who will save me from my psychosis, which has brought down so many successful people? Elon Musk doesn't need anyone to jump on a grenade for him; he needs to stop throwing them because one will explode in his hand.

Would you abandon your bank for Apple?

Banks are struggling.

• not as a result of inflation

• not due to the economic downturn.

• not due to the conflict in Ukraine.

But because they’re underestimating Apple.

Slowly but surely, Apple is looking more like a bank.

An easy new savings account like Apple

Apple has a new savings account.

Apple says Apple Card users may set up and manage savings straight in Wallet.

• No more charges

• Colorfully high yields

• With no minimum balance

• No minimal down payments

Most consumer-facing banks will have to match Apple's offer or suffer disruption.

Users may set it up from their iPhones without traveling to a bank or filling out paperwork.

It’s built into the iPhone in your pocket.

So now more waiting for slow approval processes.

Once the savings account is set up, Apple will automatically transfer all future Daily Cash into it. Users may also add these cash to an Apple Cash card in their Apple Wallet app and adjust where Daily Cash is paid at any time.

Apple Pay and Apple Wallet VP Jennifer Bailey:

Savings enables Apple Card users to grow their Daily Cash rewards over time, while also saving for the future.

Bailey says Savings adds value to Apple Card's Daily Cash benefit and offers another easy-to-use tool to help people lead healthier financial lives.

Transfer money from a linked bank account or Apple Cash to a Savings account. Users can withdraw monies to a connected bank account or Apple Cash card without costs.

Once set up, Apple Card customers can track their earnings via Wallet's Savings dashboard. This dashboard shows their account balance and interest.

This product targets younger people as the easiest way to start a savings account on the iPhone.

Why would a Gen Z account holder travel to the bank if their iPhone could be their bank?

Using this concept, Apple will transform the way we think about banking by 2030.

Two other nightmares keep bankers awake at night

Apple revealed two new features in early 2022 that banks and payment gateways hated.

• Tap to Pay with Apple

• Late Apple Pay

They startled the industry.

Tap To Pay converts iPhones into mobile POS card readers. Apple Pay Later is pushing the BNPL business in a consumer-friendly direction, hopefully ending dodgy lending practices.

Tap to Pay with Apple

iPhone POS

Millions of US merchants, from tiny shops to huge establishments, will be able to accept Apple Pay, contactless credit and debit cards, and other digital wallets with a tap.

No hardware or payment terminal is needed.

Revolutionary!

Stripe has previously launched this feature.

Tap to Pay on iPhone will provide companies with a secure, private, and quick option to take contactless payments and unleash new checkout experiences, said Bailey.

Apple's solution is ingenious. Brilliant!

Bailey says that payment platforms, app developers, and payment networks are making it easier than ever for businesses of all sizes to accept contactless payments and thrive.

I admire that Apple is offering this up to third-party services instead of closing off other functionalities.

Slow POS terminals, farewell.

Late Apple Pay

Pay Apple later.

Apple Pay Later enables US consumers split Apple Pay purchases into four equal payments over six weeks with no interest or fees.

The Apple ecosystem integration makes this BNPL scheme unique. Nonstick. No dumb forms.

Frictionless.

Just double-tap the button.

Apple Pay Later was designed with users' financial well-being in mind. Apple makes it easy to use, track, and pay back Apple Pay Later from Wallet.

Apple Pay Later can be signed up in Wallet or when using Apple Pay. Apple Pay Later can be used online or in an app that takes Apple Pay and leverages the Mastercard network.

Apple Pay Order Tracking helps consumers access detailed receipts and order tracking in Wallet for Apple Pay purchases at participating stores.

Bad BNPL suppliers, goodbye.

Most bankers will be caught in Apple's eye playing mini golf in high-rise offices.

The big problem:

• Banks still think about features and big numbers just like other smartphone makers did not too long ago.

• Apple thinks about effortlessness, seamlessness, and frictionlessness that just work through integrated hardware and software.

Let me know what you think Apple’s next power moves in the banking industry could be.