Not Boring by Packy McCormick

Welcome to the 596 newly Not Boring people who have joined us since Monday! If you haven’t subscribed, join 125,666 smart, curious folks by subscribing here:

Hi friends 👋 ,

Happy Thursday!

This really will be the shortest Not Boring in history. You have a Memorial Day Weekend to get to. But since odds are you’ll be in a car for a couple hours at some point in the next few days, I thought it would be the perfect time to listen to my favorite episode of Not Boring Founders yet.

Not Boring Founders is a twice-weekly podcast on which I talk to founders — often Not Boring Capital portfolio founders — about what the world looks like if they’re wildly successful, and how they’re making that version of the world a reality.

Normally, the episodes are about 30 minutes. For this one, with Replit co-founder and CEO Amjad Masad, we went a full 1 hour 41 minutes, covering a wide range of topics:

* Decentralized software creation

* How the internet could have been built differently

* The history and future of coding (aka when Wordcels rule the code)

* Amjad’s story: from Jordan to Codecademy, Facebook, and Replit

* Authenticity Alpha

* Balancing theory and just doing things

* Replit’s hiring spree and talent density

* The software economy being built on Replit

* Aggressiveness vs. caution in the current market

I hate listening to myself talk, and I listened to this one all the way through.

Amjad has quickly become one of my favorite people in tech, and is someone who I genuinely believe will play a big role in shaping the future. I believed that when I wrote about Replit in December, and I believe it even more strongly after this conversation.

You can listen to this episode right in this post — just press play above — or wherever you like to listen. All Not Boring Founders episodes are available on Spotify…

Apple Podcasts…

…or on the podcast player of your choice. If you liked this conversation, we’d really appreciate it if you subscribed and rated.

Big thanks our friends at FTX US for sponsoring all of Season 2.

For more Not Boring Founders — including links to all Season 2 Episodes with show notes and links — check out this fancy Notion page we made.

That’s it! Told you, short and sweet.

Not Boring will be off for Memorial Day. Have a great long weekend!

Thanks for listening,

Packy

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Today’s Not Boring is brought to you by … Secureframe

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Hi friends 👋 ,

Happy Thursday!

There are a lot of things that confuse me, but maybe none more than prescription drug commercials. People eating ice cream while a voiceover talks about herpes. The Cialis couple in the bathtubs in a field (backstory revealed below). The long list of side effects that seem much worse than whatever disease the advertised drug claims to cure.

I’ve been curious about why prescription drug commercials are the way they are forever; challenge was, I don’t know very much about healthcare. I haven’t been to the doctor in years. I’m not the guy to solve this mystery. But I know the guy.

Nikhil Krishnan’s twitter profile says it all: “Thinkboi. Making healthcare understandable through memes, shitposts, and novelty products.” He writes the funniest healthcare newsletter out there, approachable for newbies (like me) and deep enough to be valuable to industry professionals. You should subscribe:

He’s the perfect guy to explain something as simultaneously ludicrous and technical as prescription drug commercials. Mystery solved.

Let’s get to it.

Prescription Drug Commercials

A guest post by Nikhil Krishnan

As the Meghan/Harry + Oprah interview aired in March, Americans were shocked. How could the British Royal Family treat them that way?

Meanwhile, people in the UK watching the interview were also shocked. At the fact that pharmaceutical companies were advertising during the interview. 

There are only two countries in the world that allow for direct-to-consumer pharmaceutical advertising: the US and New Zealand. The only other thing these two countries share are people buying a lot of property in New Zealand.

But why exactly do pharmaceutical companies advertise to us? Does it work or affect care? What’s the deal with the million side effects they list at the end? 

I’m here to talk to you about the world of pharma marketing and how it works. But I actually want to get into how pharma marketing is evolving with technology, look at whether consumer advertising is definitively bad, and suggest that we should actually be focusing our scrutiny on physician marketing.

Why Do Pharma Companies Market to Consumers?

The first question is an obvious one. It’s the one the Brits had. Why do pharma companies market to the consumers when the consumers need to go to the doctor, and the doctor’s going to decide anyway?

Pharma advertising has largely two main goals. 

First is for undiagnosed patients. Increasing general awareness about a disease is going to make you more likely to see a doctor in the first place, which increases the chance of you getting the drug prescribed. For example if you hear a commercial that says, “If you suffer from insomnia, hot sweats, or are having nightmares that you have no idea where your social security card is,” you might suddenly realize that you have those issues and there might be something to fix them. You’ll especially see that for disease areas which are lifestyle hampering or easily self-diagnosed (sexual issues, skin and hair issues, pain, mental health, sleep issues, weight issues, stomach problems, and more). Below is some data on advertising spend by disease area.

Fun fact, Claritin was really one of the first significant direct-to-consumer pharma campaigns with their “blue skies” campaign in the mid 1990s. Now allergy meds are all over-the-counter, so the spend has dropped like crazy.

For already diagnosed patients, these ads are helpful for patients who are especially active in looking for different treatments for their diseases. This happens a lot in diseases for which there’s high variance in physician recommendations. Areas like cancer or rare diseases want to arm you with information about a drug so you actually ask your doctor if the drug might make sense for your cancer type. As personalized advertising gets more targeted and the therapies themselves target smaller and smaller patient segments, ads for these drugs become a better investment. They have exploded accordingly. 

What Are the Rules Around Marketing to Consumers?

As you can imagine, pharma marketing is murky and there are tons and tons of rules around what you can and can’t do. But I thought I’d just go into a few.

Rule 1: The product name has to be memorable for consumers but cannot be even close to confused with any drug that’s already on the market.

Quick game, which of these is a drug name and which are Lord of the Ring Characters? Galadriel, Horizant, Zestril, Elendil, Denethor, Afinitor. Be honest, you got less than 50% right.

Drug companies want you to remember the name (feat Fort Minor) but also will 100% get sued for trademark issues by other drug companies if you even slightly seem to be riding the coattails of their brand success. Plus, the FDA obviously doesn’t want consumers to get two drugs confused; taking the wrong one can cause serious health issues. That’s why you have these very strange sounding, un-Googlable drug names, advertised directly to consumers.

Rule 2: The advertisements need to say the name of the drug (brand and generic), at least one FDA-approved use for the drug, and the most significant risks of the drug.

While there are some nuanced differences between print, television, radio, etc. the general gist is that drug manufacturers need to give a “fair and balanced” view of the drug. That means including the major side effects.

This is usually the most jarring part of pharma advertising. When an ad airs, it sounds like the drug is just as likely to kill you as it is to help you, and the side effect listing will happen over some lovely couple running through a field of tulips or whatever so it doesn’t actually seem that bad. Non-US residents can see an example here.

Rule 3: There are different rules between “product claim” advertisements, “reminder” advertisements, and “help seeking” ads.

I was on the subway the other day and I saw what I thought was possibly the worst advertisement I’ve ever seen. Oh you wanna know what this product is? F*** you.

This is an example of a “reminder” advertisement. It’s not actually making any claims about what the product does. It’s just reminding people who might already know about the product that it does in fact exist. Really high-risk products will still have to include a “boxed warning” on these ads. These are different from the “product claim” advertisements I’ve been talking about where the drug actually says what it treats and how well it works.

So those are two types of pharma ads, but to make it even more confusing there’s a third called “help seeking” ads. These are ads that actually aren’t about a product at all, they’re just talking about symptoms of a condition generally and HAPPEN to have the logo of a drug company on it without talking about the drug itself, and will say things vaguely like, “There is help, ask your doctor today.” These kinds of ads actually fall under the FTC instead of the FDA.

Pharma Marketing is Evolving

Like every part of healthcare, eVeRyThinG ChAngEd WiTH TeCh. Here are some examples.

* Ads shifting to the point-of-care

Welcome to the 1,265 newly Not Boring people who have joined us since last Monday! Join 47,388 smart, curious folks by subscribing here:

Today’s Not Boring is brought to you by… Rows

In March, I wrote that Excel Never Dies. I may have spoken too soon. Rows very much wants Excel to die. It has a shot: Rows is one of the most “Holy shit 🤯” new product experiences I’ve had in a long time.

Rows is a spreadsheet powered by APIs, with built-in integrations that let you enrich mailing  lists, learn what’s in a company’s tech stack, find company data via Crunchbase, and much more, right in the spreadsheet. They even made me a template to monitor trending tweets on topics I’m writing about. 

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Everything in Rows is formula-based. It’s kind of like if Excel, Airtable, and Zapier had a baby, plus access to databases that normally live behind paywalls.

It’s really incredible already, and it’s still in beta. Rows wants Not Boring readers -- people who love finance & tech -- to be among the early adopters. You should just try it for yourself, on me:

Hi friends 👋 ,

Happy belated Mother’s Day to all the not boring moms!

Most of the time at Not Boring, I write about companies, with facts and figures and histories and graphs. Occasionally, I’ll write about concepts and business models, like the Metaverse, DAOs, or APIs. Sometimes, I’ll let you into my brain to see what’s going on in there before an idea is fully baked, when its just a bunch of wisps starting to form a braid.

Today is one of those pieces. It’s shorter. It’s meant to be interactive. Most of the fun will happen when you take the idea and try to apply it to your own work or life. 

To be clear, much of today’s essay is based on my own personal experience. I fully understand that not everyone has the luxury of having a roof over their head, food on the table, and an internet connection. Many people can’t afford the time to play the game. 

But if you take the hours it takes to read Not Boring, you’re probably already playing the Great Online Game to some degree. You read this because you want to know how the online economy works, and how you can play it better. But you can’t play to win unless you know you’re playing.

Let’s get to it.

The Great Online Game

(Click this if you just want to jump to reading online)

This didn’t start as a piece about games. I set out to answer this question: why are tech growth stocks sagging while crypto moons and value roars back? 

But I figured out how to explain that out in way fewer words: 

Crypto is just more fun. 

But crypto itself is not the game. It’s just the in-game currency for a much bigger game, played across the internet, that involves CEOs, influencers, artists, researchers, investors, and regular people, like you and me. That’s a much more fun topic to explore than which asset class is outperforming which. This is bigger, more permanent than day-to-day market fluctuations.

We’re all playing a Great Online Game. How well we play determines the rewards we get, online and offline.

The Great Online Game is played concurrently by billions of people, online, as themselves, with real-world consequences. Your financial and psychological wellbeing is at stake, but the downside is limited. The upside, on the other hand, is infinite.

Social media is the clearest manifestation of this meta-game. Beginner-level Twitter feels weird, like a bunch of people exposing their personal thoughts to the world. Medium-level Twitter is Threads and engagement hacks. Twitter Mastery is indistinguishable from an ongoing game. This is also true for Reddit, Discord, Instagram, TikTok, Facebook, and other social networks. 

But social media is just one piece of an interconnected game that spans online and offline spaces. The way you play in one area unlocks opportunities in others. Sharing ideas on Twitter might get you invited to a Discord, your participation in that Discord might get you invited to work on a new project, and that new project might make you rich. Or it might bring you more followers on Twitter and more Discord invites and more project opportunities and new ideas that you want to explore which might kick off any number of new paths. 

We now live in a world in which, by typing things into your phone or your keyboard, or saying things into a microphone, or snapping pictures or videos, you can marshall resources, support, and opportunities. Crypto has the potential to take it up a notch by baking game mechanics -- points, rewards, skins, teams, and more -- right into the whole internet. 

The Great Online Game is free to play, and it starts simply: by realizing that you’re playing a game. Every tweet is a free lottery ticket. That’s a big unlock.

Anyone can play. You can choose how to play given your resources and skills at the current moment. You can level up fast. Financial and social capital are no longer tied so tightly to where you went, who you know, or what your boss thinks of you. This game has different physics and wormholes through which to jump. It’s exponential instead of linear.

To understand how the game works and how to play, we’ll work our way up: 

* What is a Video Game? 

* The Great Online Game 

* Meet the Players

* How Crypto Supercharges the Game

* How to Play the Game

By the end of this post, I hope I’ve convinced you to throw a couple coins in and start playing, but I think I might need to show you that we’re even playing a video game first.

What is a Video Game? 

It’s Monday morning. You’re tired. You have to go to work. You have an assignment that you pushed off on Friday, because it’s practically Hot Vax Summer and you had plans, but now it’s Monday and damn. Now you need to do that thing. This does not seem fun. This does not seem like a game. 

So it might take me a minute to convince you that yes, it is, even for you. I’m going to start my argument like a shitty high school valedictorian: 

The Oxford English Dictionary defines a video game as, “A game played by electronically manipulating images produced by a computer program on a television screen or other display screen.”

If you’re working remotely from a computer, what you’re doing perfectly fits the definition of a video game. 

Nik Milanovic nailed it:

Hit the right keys in the right order, make money. Work is just an often boring sub-game within the meta-game. 

But that’s still a little literal, and a lot reductive. Let’s go deeper. The best games, according to gaming entrepreneur turned top solo investor Josh Buckley, “are creating spaces that bring you into flow.” 

On Invest Like the Best, Buckley said:

The biggest games today really take advantage of this, but you wouldn't actually think of them as a game. I look at Twitter, Facebook, and Instagram as games and 3 billion people are playing them actively. They're essentially big layers on top of a slot machine.

Buckley went on to lay out four elements of successful game design: 

* Frequent Feedback Loops

* Variable Outcomes 

* Sense of Control

* Connection to a Meta-Game

All four are present in the Great Online Game, none more importantly than the connection to the meta-game. 

The Great Online Game 

“The internet is incredible.” You’ll hear that a lot from people who’ve started to master the Game. As I typed that last sentence, Blake Robbins tweeted this: 

Getting good at the Great Online Game makes seemingly absurd things happen. Your business icon? In your DMs. That person whose videos you don’t miss? Just reached out for a collab. Your dream job? Reaching out to you to tell you why Company X might be a fit. 

Blake has successfully translated “hanging out on the edges of the internet” into a career as a venture capitalist at Ludlow Ventures. He’s a go-to source on creators, gaming, and future internet stuff more broadly for some of the smartest peopl…

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Today’s Not Boring, the whole thing, is brought to you by … Truework

Read on to learn how Truework is building the verified identity layer of the internet.

Hi friends 👋 ,

Happy Thursday!

I met Ryan Sandler, Truework’s CEO, via an introduction from Ramp co-founder and CTO Karim Atiyeh. Aside from running NYC’s fastest ever unicorn, Karim is also a top angel investor. One mutual friend told me that no one is better at identifying strong engineering teams than Karim. So when he told me I needed to look into Truework, my ears perked up.

Karim was right. Truework reminds me a lot of Ramp, a Not Boring favorite: Rabois-backed, fintech, Harvard founders, going after an absolutely enormous market led by a too-comfortable incumbent, strong technology chops, and a long-term, worldbuilding strategy starting with a smart wedge.

It’s different than Ramp, too. First, it’s not starting with a product that the end-user touches. It built a platform and API used mostly by employers and verifiers. It’s intentionally unsexy. Second, it has a different ambition, which required it to act differently, more quietly, in the beginning. (Until now. That’s why we’re here.) And third, Truework is a privacy-first company.

Truework’s story has lessons for founders, investors, anyone who works in regulated industries, and even incumbents. It’s a masterclass in Worldbuilding.

This essay is a Sponsored Deep Dive on Truework. For those who are new around here, that means that Truework is paying me to write about their business, but that I would have written about it anyway. You can read more about how I pick and work with partners here.

Let’s get to it.

Truework: A True Strategy Masterclass

This is a story about strategy. 

It’s also about privacy, identity, income verification, credit bureaus, breaches, regulations, and owning your data. It’s about worldbuilding and unsexiness. It’s about the ability to fill out a mortgage application simply by clicking “login.” But mostly, it’s about strategy. 

Truework launched in late 2017 with a vision: empower people to own and control their personal information. That’s one of those “much easier said than done” visions. Others have tried and failed. To succeed, you need a strong wedge, and a master plan. 

Truework has both, and is executing on one of the most patient and ambitious worldbuilding strategies I’ve seen, backed by Keith Rabois at Founders Fund, Alfred Lin at Sequoia, and Steve Sarracino at Activant. You don’t assemble that board if you’re fucking around. 

Its master plan starts with employment and income verification, a process that touches all of us. If you want a house, a job, or a car, your lender or employer needs to confirm where you work and what you make. It’s a $5+ billion market with one dominant incumbent, a bunch of small players, and a lot of pen, paper, emails, and faxes. It’s broken, unsecure, and slow. 

But employment and income verification is a wedge into a much bigger opportunity: to become the verified identity layer for the internet, giving people control of which data they share, and where, and speeding up transactions that require trust. 

Truework’s journey thus far, and it’s plan for the next half-decade, is a case study on how tech startups can win huge markets controlled by dominant incumbents without using low-end disruption. Let’s study: 

* Meet Truework

* How to Win a Legacy Industry 

* Regulatory Counter-Positioning

* The Verified Identity Layer

Meet Truework 

In 2017, after product managing LinkedIn Salary (a Glassdoor competitor) to launch, Ryan Sandler left LinkedIn and linked up with his Harvard roommate, Ethan Winchell, and fellow LinkedIn-er, engineer Victor Kabdebon, to explore ideas for their own thing.

Having gotten interested in data ethics in college, Sandler knew that he wanted to start a company in the data privacy space, but he didn’t know exactly what the idea was. He did know which boxes it needed to check: 

* Unsexy 

* Overlooked by Silicon Valley 

* Lots of data

* Large market

Once they identified spaces that met their criteria, they cold emailed companies to pick their brains, narrowed the list down, and started talking to customers to validate the top ideas. After speaking with mortgage lenders, they chose employment and income verification. Sandler told The Venture Brief they chose the category because of: 

How overlooked it was, yet such a big market, and so important in the economy. Every time someone gets a loan, apartment, a new job, there’s sensitive information that needs to be verified about them. Most prominently, their income, employment, assets, credit, other pieces of their identity. And consumers have no idea that this information is being verified and being shared with a ton of third parties.

Employment and income verification checks all the boxes. 

* Privacy has been a huge issue, despite the sensitivity of the data. ✅

* It’s unsexy. ✅

* It’s overlooked by Silicon Valley (quick, name your favorite employment and income verification startup). ✅

* There’s a ton of data: the product is all about collecting and sharing data, fast and securely. ✅

* It’s a massive market. ✅

In 2020, the industry leader did nearly $1.5 billion in revenue, up 51% YoY. Income is one of the best measures for underwriting; verifying that income is the glue that holds lending together. Dodd-Frank, the consumer protection legislation that came out of the housing crash in 2008, even mandates that lenders verify the data before approving a mortgage. 

Verification of employment (VOE) and income (VOI) is so critical that even after a data breach that exposed over 145 million Americans’ data, Morningstar analyst Brett Horn told CNN, “I think, frankly, it’s not in the interest of the industry or even regulators to shut down [a credit bureau involved in the leak]. They provide an essential service for consumer lending.” 

Until 2017, the industry and regulators didn’t have much of a choice. Enter Truework. 

Starting with employment and income verification, Truework is building a digital-first credit bureau that makes it faster for consumers to apply to loans, apartments, jobs, and more, while maintaining privacy. 

It’s a three-sided network: 

* Verifiers: Lenders, landlords, employers, and others need to verify your data in order to give you a loan, rental, or job. They’re the payers in the network, paying each time they need to verify information. 

* Employers: Employment and income data lives, unsurprisingly, in HR and Payroll systems. Truework works directly with companies, and with payroll providers like Gusto, to access that data directly. 

* Consumers: The people whose data is being accessed and shared are typically overlooked in this network. They often don’t even know that Employers, Verifiers, and credit bureaus are sharing their information behind the scenes. 

Truework brings Consumers into the loop. Employers provide data to Truework, but Truework never shares that data with Verifiers without digital consent each time the data is shared. That seems like it’s obviously the right move, but it’s not the way it works today. 

To make the process smooth, fast, and easy for Verifiers, who are the paying customers, Truework has three products that roll up into a one-stop solution for income verification.

The bread and butter is the Instant product. This is what lenders and other Verifiers care about most: with the Consumer’s consent, data is returned cleanly and instantly, without any user friction to cause drop-off. Truework has spent the first 3.5 years of its life building up partnerships with companies and HR and Payroll providers like Gusto, Zenefits, and Paylocity to create a database of 35 million employees. It’s already the second-largest network, and it’s growing quickly (100x in the past year alone).

Truework recently added Credentials to its waterfall. There are a number of players now attackin…

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Today’s Not Boring is presented by… Masterworks

In January I wrote about Masterworks. As a refresher, Masterworks is the first and only platform that lets regular folks (like me) invest in blue-chip artworks at a fraction of the entry price. At the time I had invested in three Masterworks offerings. Since then I have added three more pieces to my portfolio: a Haring, a Bradford, and another Basquiat. Fancy.

Not only do I think it’s prudent to have real asset exposure to hedge against inflation (thanks J Pow 😉 ), but I also love learning about these artists and their markets, and Masterworks brings some intense data analysis to the table.

Art can make sense in everyone’s portfolio. Contemporary art returned 13.6% from 1995-2020 with a low loss rate and virtually no correlation to equities. Plus, unlike other collectables or even BTC, supply is constantly decreasing. It’s kind of like ETH … ultrasound art 🦇🔊

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Hi friends 👋 ,

Happy Monday! 

Mario Gabriele is one of my favorite writers. Read the opening paragraphs in this essay and you’ll understand why. He somehow makes business writing beautiful.

Between his briefings, Startup Ideas, and The S-1 Club, Mario’s The Generalist is can’t miss content. If you like Not Boring, you’ll like The Generalist.

Aside from a general business nerdiness, Mario and I share a few things in common:

* A fascination with conglomerates.

* Large Indian readerships.

This week, with India’s COVID crisis continuing to escalate to frightening heights, we decided to team up to explore the past, present, and future of one of India’s most beloved companies, and one of the leaders in the fight against COVID: Tata Group.

In addition to bringing awareness, Mario and I have both made donations to organizations aiding India's fight against the coronavirus. We'd encourage those of you that can to do the same. Both New York Magazine and the New York Times have lists of reputable NGOs putting funds to good use. If you’re in India, my friends at Pesto put together a website with resources including ICU beds and oxygen supplies.

Let’s get to it.

Transforming Tata

A message to all the tycoons out there: beware of your grandchild. 

Though the Bible advances the parable of the prodigal son — the wasteful offspring that fritters a father’s money — statistically, it is the third generation that marks the end of a family fortune. One American study indicated that 90% of wealth evaporates by that point, the casualty of frivolous investments, generational dilution, and dwindling determination. Even the colossal wealth of Cornelius Vanderbilt — worth $227 billion when adjusted for inflation, giving him a cool $96 billion edge over Bezos — dissolved in his expanding gene pool. 

All of which is to say: that Tata is here at all is remarkable. 

Four generations and more than 150 years after its founding, Tata is not only still standing but essential. Just this week, the company aided in India’s coronavirus response, agreeing to contribute 800 tonnes of oxygen per day to health facilities in need. Far from an isolated example, such civic-mindedness is at the heart of Tata’s history, no doubt part of the reason one Twitter commentator referred to it as India’s “parallel government.” Over a century and a half, the conglomerate has supported (and commercialized) Indian life, unlike any other company. In the process, Tata has constructed a dizzying tessellate of over 100 businesses, from automobiles to apparel, steel production to tea. 

And yet, there’s the sense that despite its durability, Tata’s may be in decline. With infighting beleaguering the founding families and legacy businesses struggling to adapt to a digital world, Tata will need to work hard to ensure it remains a potent force. To do so, the company will need to shed legacy baggage, embrace the opportunities the tech sector presents, and lean into the essence of what makes Tata an enduring brand. 

In today’s piece, we’ll explore: 

* Tata’s rich history, beginning with the opium trade

* The complexion of a messy conglomerate

* The necessary moves to perpetuate the dynasty

History

The story of Tata Group is the story of modern India. The conglomerate’s creation and ascent both influenced and responded to seismic changes in the country beginning under colonialist rule, adapting under socialist independence, and flourishing in an open economy. 

It all begins in 1822 in a city on India’s Western Coast. 

Nusserwanji: Zoroastrianism and family business

Every company is defined by its culture. On that count, Tata can lay claim to an especially ancient heritage: the religion of Zoroastrianism. 

Founded in the 6th century BC, Zoroastrianism is defined by a stark delineation between good and evil, and a gentler gospel of kindness. As noted in the excellent The Tata Group book, adherents believe to attain happiness you must help others, and that salvation is achieved by “Humata, Hukhta, Hvarshta” or “good thoughts, good words, good deeds.” Hundreds of years later, those three words were inscribed on the mausoleum of Tata’s Chairman, emphasizing how Tata’s civic and philanthropic orientation is inextricably linked with the religion. 

Nusserwanji Tata must have been something of a rebel. Born in 1822 in India’s Gujarat region, Nusserwanji was the first family member in over fifteen generations to eschew the call of Zoroastrian priesthood and enter the private sector. He learned the ropes by training with a Hindu banker before setting out on his own, founding an export firm with a focus on opium, and other less scandalous commodities. 

As the firm grew, Nusserwanji began to rely more on his son, Jamsetji, bringing him into the fold in 1859. Educated at the English-influenced Elphinstone College, Jamsetji had the privilege of a more global worldview than his father, fostered by business trips to London and Manchester. The latter city, seething with industrial energy, was believed to have made a particularly strong impact, with the young Jamsetji simultaneously enraptured by Manchester’s industry and disgusted by the “medieval vision of hell” in which workers toiled. 

But amidst the smoke and chaos, he saw promise. It was time to build a “Manchester in the East” with a humanity that would put India’s colonists to shame.  

Jamsetji: Founding Tata Group

In 1868, Jamsetji officially founded Tata Group, beginning with an investment of 21,000 rupees. Over the succeeding 36 years, he would establish a generational business and set in motion a series of ambitious infrastructure plans, earning the nickname of “the man who saw tomorrow.” That growth would be achieved while treating workers with uncommon dignity and respect. 

It started with the acquisition of a decrepit oil mill. Jamsetji promptly transformed it into a cotton production facility before selling for a quick profit. (Let’s get that IRR, Jamsetji.) Aided by a fact-finding trip to Lancashire and the recruitment of English specialists, Jamsetji parlayed that win into the creation of Empress Mills — a new cotton facility that drew on global knowledge. Two additional mills followed. 

Those four cotton mills set the financial groundwork for Tata’s later expansion, as well as pioneering the company’s legendary culture and care for its employees. Among other innovations, Jamsetji took pains to ensure workers had access to filtered water, sanitary facilities, low-cost grain, credit, a library, a pension fund, accident compensation, and much more. All of this at a time when the notion of managerial benevolence was effectively non-existent among Western industrialists. Decades later Upton Sincl…

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Hi friends 👋 ,

Happy Thursday!

Startup stock options are one of those things that startup employees should know a ton about but just don’t. There’s a never-ending debate in tech around whether stock options make sense for employees, or whether they’re just a way for companies to pay less cash. Even when things seemingly go really well for a company, employees’ situations are often murkier than it seems.

That’s why I was so pumped when Shanna Leonard, who runs marketing at Secfi, reached out about working together. I’ve been wanting to write about this forever.

This essay is a Sponsored Deep Dive on Secfi. For those who are new around here, that means that Secfi is paying me to write about their business. You can read more about how I pick and work with partners here.

This one is a little bit different though. The Secfi team really just wants more startup employees to know what their options are, make a plan, and not leave millions of dollars on the table. Each person I’ve spoken to there has their own personal startup equity horror story, and they want to make sure that you don’t go through the same thing. I, too, gave up cash for equity, and it was a terrible financial decision. This one is personal.

Obviously, if Secfi can help you make smarter decisions, that’s a win-win, but more thoughtfulness around employee equity is a win in itself. So we’re going to go deep on how equity works, why people don’t exercise, and what happens when they don’t.

(One note: I wanted to call this post ESOP’s Fables, but ESOPs are a public company thing more than a private company thing. But I thought it was clever, so I couldn’t not share.)

Let’s get to it.

Startup Stock Options Options with Secfi

In 2020, startup employees left $4.9 billion on the table by not exercising their pre-IPO options. 

Not exercising pre-IPO means employees missed out in two major ways:

* They let the typical 90 day window pass after leaving and forfeited unexercised options, either all of their options or a portion. 

* They stayed at the company through IPO, but didn’t exercise before the IPO and had to pay short-term capital gains or ordinary income instead of long-term capital gains because of “cashless exercising.” Costs can soar post-IPO.

That combination cost employees four point nine billion dollars. $4,900,000,000. 4,900 million. At Snowflake alone, ex-employees left 72 million options worth $1.27 billion unexercised. Ouch. 

Those numbers are so big as to feel kind of meaningless, but they represent years of blood, sweat, tears, uncertainty, and financial trade-offs down the drain. 

Most people who work for early stage startups take less cash compensation than they’d be able to get at a more mature company in exchange for a few things: a more fun work environment, the chance to change the world, more responsibility than they’d get elsewhere, and a host of soft benefits, but mainly, they do it for the employee stock options. 

Employee stock options are the lifeblood of a startup. Options are the main way startups compete on comp with big companies like Google and Goldman that can afford to pay infinity times more cash. They offer the promise of millions and millions of dollars if things go really, really well. 

When I left Bank of America Merrill Lynch and went to Breather, I took a 70% pay cut on the cash side, but I got options worth 1% of the company in exchange. Even coming from finance, I didn’t fully understand my options. I just did some hyperoptimistic expected value math (1% * $1 billion = $10 million!) and that was good enough for me. 

I’m certainly not alone. Most startup employees don’t understand their options. Some don’t even know they need to exercise them or put out money at all. Because options feel like lottery tickets at the early stage, employees don’t think all that much about things like the tax implications of when they exercise, what happens if they leave the company, and all of the little details that can mean hundreds of thousands or even millions of dollars. Which is crazy, because those options can often represent, on paper, a huge percentage of their net worth. 

For a group of ostensibly intelligent people, startup employees put surprisingly little thought into managing their options. These are builders. They get so immersed in their day-to-day and building great things that they lose sight of their own personal gain at times. Plus, it’s kind of taboo to talk about maximizing the value of your options when there’s real work to be done. 

And most companies don’t do much to help. It’s (generally) not because they don’t want to, but because this stuff is really complicated, and so far in the future, and startups have dozens of more pressing fires to put out at any given time. In the Eisenhower Decision Matrix, employee options fall into the “important, not urgent” bucket...

UNTIL all of a sudden, your company is all over the news. It’s going to IPO. Everyone is talking about it. You did it. Finally! But, wait, what the hell happens to your options? It costs HOW much to buy them and you owe WHAT in taxes? Now, it becomes personal. And urgent. 

A lot of startup employees are going through that emotional arc right now. 2021 looks like it’s going to be even more painful for ex-employees who didn’t exercise their options (and even for current employees who will pay higher taxes if they haven’t planned properly, but it’s hard to feel too bad for them). 

The year is less than four months old, and there have already been 429 IPOs on US exchanges. This time last year, there were 40. That’s a 10x increase. To be fair, a lot of the new IPOs are SPACs -- 308 SPACs have raised $99 billion via IPO already this year versus $83 billion in 248 IPOs all of last year -- but there have been some major tech IPOs already this year: 

That’s an incomplete list, plus those 308 SPACs and many of last year’s 248 are lurking with bags full of money that they need to spend on taking companies public within two years. 

For people who own equity in those startups, this is going to be an amazing year. Thousands of people will become millionaires for the first time, some will generate multi-generational wealth, and a few will even become billionaires. But each of those companies also has tons of former employees consumed by regret at not having purchased their options, and many others who will end up giving the government nearly as much as they take home. 

Secfi wants to change that, starting by helping you get smarter on startup equity: 

* How Startup Equity Works

* Why Employees Don’t Exercise 

* Options Exercise Options 

* Meet Secfi

* The CAC Arbitrage

* Secfi’s Vision

The best time to start thinking about how to handle your options was when you got your offer letter. The next best time is now. 

Secfi can help. I could (and will) nerd out on this problem for hours, but Secfi is paying me and I want to make sure you check them out, so I’ll introduce you to Secfi now, then we’ll come back to them later. 

Secfi is a team of equity experts 100% focused on helping startup employees understand, maximize and unlock the value of their stock options and shares. If you’re an employee at a startup, Secfi wants to make sure you’re on the right track. Really. I badly want this piece to go viral mainly because the team genuinely cares so much about helping startup employees.

So here’s an ask: if you know an employee at a unicorn startup, share this essay with them to make sure they’re thinking through things properly.

Secfi has educational resources, tools (including tax calculators), and real live people who can help you think through your equity. Secfi’s equity strategists have deep experience as financial advisors, wealth managers, investment managers and analysts, and tax professionals, and have worked wi…

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Hi friends 👋 ,

Happy Monday! We have a special one for you today. 

Back in January, I wrote a piece about Alibaba. Lillian Li, whose writing on Chinese tech I’d read and respected, but who I’d never met, DUNKED on it on Twitter. 

She said that “the piece missed local context.” Which, fair. She also wrote a more complete response on her Substack, Alibaba: from growth to value.

I loved getting Lillian’s perspective -- one of the reasons I write is so people who are smarter on a particular topic share their knowledge. And when it comes to China tech, Lillian, who worked as a VC in Europe but is now based in China, is as smart as it gets. She writes a great newsletter called Chinese Characteristics. You should subscribe if you’re interested in China tech, and you should be interested in China tech: 

Lillian and I got to know each other after that exchange. We decided to team up. Reprise the ol’ bull and bear schtick, but together this time. In other words, we shifted our debate method to Real-Time Engagement (I promise, this will make sense /maybe be funny in a minute).

Let’s get to it. 

Today's Not Boring is brought to you by Public

As you read above, the fastest way to get smarter about investing is to put your ideas out there and get dunked on by … errr... have a conversation with other smart investors. That's why I use Public. 

Public is an investing app AND a social network for talking about business trends, and the social features make it fun and easy to share ideas. 

I'll be discussing today's piece on Public. Hit the link below and follow me @packym to join the conversation. Btw, if you’re looking to transfer your account from somewhere else, they’ll even cover the fees.

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Agora: Bull & Bear

In 1997, two Chinese engineers joined the founding team at early video conferencing startup WebEx. A decade and a half later, each started his own company.

One, Eric Yuan, founded a company you’re all too familiar with: Zoom. The other, Bin “Tony” Zhao, founded Agora. 

If you’ve joined a conversation on Clubhouse , attended a virtual event on RunTheWorld, or binged livestreams on Bilibili you’ve experienced Agora. It’s been sitting there, in the background, making sure the audio and video come through clearly. 

Agora builds real-time audio and video capabilities and delivers them as a Software Development Kit (SDK) and Application Programming Interface (API) for app developers. It’s an API-first company that makes it easy for developers to add real-time video and audio into their product. Stripe for Real-Time Voice and Video Engagement, if you will. The company is so API that its ticker is API. 

Agora is also a great excuse to cover a few different relevant topics:

* API-first businesses and business models

* Live video streaming and all of its use cases, like telemedicine and education 

* The audio chat wars

Because Agora sits in the background -- it’s a “picks and shovels” company -- it doesn’t care who wins as long as more people communicate, learn, heal, play, and “live real life online,” in real time. 

Agora, dual-headquartered out of Shanghai and Santa Clara, went public in June last year. It was relatively quiet for its first six months as a public company, bouncing around the $3-6 billion market cap range, until investors picked up on the Clubhouse connection in January and sent shares soaring. In February, the company topped out over $12 billion before crashing after providing conservative 2021 guidance on its last earnings call. 

Source: Atom Finance

Today, the company is trading at a $6.5 billion valuation on projected 2021 revenue of $182 million. It’s cheaper, but it’s not cheap. As Packy was browsing atom for its numbers, he was confused when he saw that FY21 consensus Enterprise Value (EV) / EBITDA was 4.06x. Seemed like a steal. Then he looked more closely: that’s 4.06 thousand times EBITDA. 

It’s less than eight years old and still growing quickly (74% YoY revenue growth) and most of its revenue still comes from China (~80%). It’s young and fast-growing enough that whether you’re bullish or bearish on the company depends less on today’s metrics, and more on how you think about its growth potential and defensibility going forward. There’s a good case to be made on both sides, and we’re going to do just that. 

Packy’s going to take the bull case, and Lillian’s going to take the bear case. Then we’ll fight it out and let you know where we end up. To get there, we’ll cover: 

* Agora’s History

* $API’s API

* China’s Livestreaming Boom

* What Agora Looks Like Today

* The Bull Case for Agora

* The Bear Case Against Agora

* Bull or Bear? 

To kick it off, let’s go back to the granddaddy of online video communication: WebEx. 

Agora’s History: From WebEx to YY to API

Who knows what video communication on the internet would look like today if WebEx just embarrassed its employees a little less. 

Eric Yuan explained to Bessemer partner Byron Deeter, “Every time I talked to a WebEx customer, I felt very embarrassed, because I did not speak with a single happy WebEx customer.”

After fourteen years at WebEx, the last four under Cisco, which acquired WebEx in 2007, Yuan left to found Zoom in 2011. He set out to build what he couldn’t convince Cisco execs to let him build at WebEx, a new version of the product rebuilt from the ground up with customer happiness in mind. 

Bin “Tony” Zhao, another WebEx founding engineer had similar feelings. After building and releasing real-time audio sessions, he said on GGV Capital’s Next Billion Podcast, “I started to regret taking that job, because I got a lot of complaints after the first release, and I realized there are some complaints that I believe I cannot solve at that time.”

Zhao didn’t have Yuan’s patience. He left in 2004 to start NeoTasks, which he describes on his LinkedIn page as: “P2p streaming technology and service provider for various companies in media, advertising, video sharing industries.”

In 2008, Zhao sold NeoTasks to Chinese streaming site YY.com and joined the company as CTO. That experience shaped what he would build at Agora. 

YY during the early 2010s was China’s Second Life. The documentary called People’s Republic of Desires gives a glimpse into this brave new world where fortunes were made and lost overnight. According to Interconnected’s Kevin Xu, “Is one of the first livestreaming platforms to reach scale in China, if not the world. It is arguably one of the first instances where people were ‘living real life online.’” Like Tencent’s QQ, which was early to new forms of online monetization like avatars and digital gifting, YY was early to gifting and tipping with virtual goods and real money, a behavior that’s now common online. 

The company also pushed the boundaries on real-time engagement. Xu told TechBuzz China’s Rui Ma that under Zhao, YY could handle 8 million concurrent users, and up to 100k in the same room, back in 2011. That year, it handled 421 billion voice minutes, more than Skype. 

After working in B2B at WebEx, YY opened Zhao’s eyes to the potential of the consumer internet. He told GGV’s Next Billion Podcast: 

I start to realize this technology is not going to be only sitting in the conference room, not only serve the purpose for people to negotiate or discuss certain business topics, it actually helped people to live online. Like they can play, they can have a party, they can sing karaoke, they can actually make friends online through video chat, audio chat. I can envision from there, people can actually live online and that’s part of the inspiration that led to …

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Today’s Not Boring is brought to you by… BlockFi

BlockFi is a new kind of financial institution. With BlockFi, you can use cryptocurrency to earn interest up to 8.6% APY (I’ll explain how below), borrow cash against your crypto holdings, and buy or sell crypto. No minimum balances or hidden fees. Tip: signup is smoother in the mobile app. Set up your BlockFi account today, and get up to $250 in free bitcoin:

Hi friends 👋 ,

Happy Thursday / Tax Day!

Today’s post couldn’t have been timed any better. I’ve been talking to the BlockFi team for a couple of months, and we picked April 15th about a month ago. We didn’t know that Coinbase would be IPO’ing yesterday, or that I’d be so deep down the crypto rabbit hole at this point. It’s fate.

This is a Sponsored Deep Dive on a company I’ve been wanting to dig into for a long time. BlockFi offers up to 8.6% APY on deposits, which is obviously tempting and also confounding. I’ve had so many text conversations with friends that go something like, “I want to do this, but it has to be bullshit, right? How does that even work? We need you to do a Not Boring on this.”

I’m happy to report that it is not bullshit, and I have the receipts to prove it.

Let’s get to it.

Is BlockFi the Future of Finance?

Coinbase IPO’d yesterday to wild success. After touching $420.69 and going as high as $429.54, it closed at $328.28, up 31% from its reference price of $250. It peaked at a market cap of over $100 billion, and closed at $86 billion. 

I’m more excited about BlockFi, though, and not because they’re sponsoring this post. It’s a more selfish reason, one that makes the sponsorship money seem like peanuts. 

See, if BlockFi existed in 2013 instead of Coinbase, I probably wouldn’t even be writing this newsletter. 

On May 16, 2013, when Coinbase was less than a year old, I set up an account and bought my first bitcoin. I forget why, but I just looked up when Union Square Ventures first invested, and that must have been it: 

That was good enough for me. I bought 10 BTC on May 16th, another 15 on June 14th, and another 13 on July 12th. 

That September, after quitting my job in finance, I flew my unemployed ass to Oktoberfest for a fun weekend with a few friends. On September 24th, after ten too many steins, I woke up in my Munich hotel room a little hungover and feeling dumb for spending so much on the trip and the night out... and made the stupidest financial decision of my life. 

I just sold some of those silly bitcoin I’d bought, and bingo, free Oktoberfest. It felt like such an obviously responsible thing to do that three days later, I sold ten more, then I sold eight in October, five in November, and the last five in May (for a nice little 4x, I might add!). 

I sold all 38 bitcoins for a total of $7,232. At current prices, those 38 bitcoins are worth $2,450,050. Gulp. 

If BlockFi had been around at the time, I could have taken out a USD loan against some of those bitcoin and earned interest on the rest while they sat safely in my account. If BlockFi paid interest on bitcoin that whole time, like they do today, I’d have more than 40 bitcoin today, or over $2.6 million. Double gulp.  

I’ve told you before that I’m an idiot, and I wasn’t kidding. But that’s enough self-chastising for one day. We’re here to talk about BlockFi.

Is BlockFi Legit?

BlockFi, which just announced a $350 million Series D led by Bain Capital Ventures, Pomp Investments, Tiger Global, and partners of DST Global, is building a full-fledged financial institution for crypto investors. BlockFi offers four products to retail investors: 

* BlockFi Interest Account (at rates up to 8.6% APY)

* Trading Accounts

* Crypto-Backed Loans

* Credit Card

It also acts as a prime broker for institutional clients, with custody, financing, execution, and margin. 

BlockFi is building SoFi plus JP Morgan’s prime broker desk, for crypto. 

There’s a race going on among everyone in the financial services space -- centralized crypto companies like BlockFi and Coinbase, neobanks like Chime and Monzo, public fintech companies like Square and PayPal/Venmo, and large brokerages and banks -- to become the financial super-app, the place that customers go for loans, credit cards, trading, insurance, cash management, and more. BlockFi has a unique wedge: a growing suite of products that earn clients high interest rates and free crypto.

The first question anyone has when they hear about BlockFi is: “What’s the catch? 8.6% APY sounds too good to be true. That can’t be legit.” 

I went DEEP to understand how they do it, and it’s legit. Essentially, BlockFi arbitrages the fact that traditional finance and crypto don’t like to deal with each other. 

To understand how it works, we’re going back down the crypto rabbit hole. We’ll cover topics like bitcoin, stablecoins, DeFi, and CeFi, and basis trades. You’ve probably heard the terms, but probably, like me, didn’t fully understand what they mean. We’ll change that. At the very least, we’ll all sound smarter at our next party.

There’s so much to dig into here that it’s hard to know where to start, but we’re going to try:

* What Does a Bank Do? 

* What BlockFi Does

* Stablecoins and 8.6% APY

* Grayscale Bitcoin Trust

* The Race to the Finance Super App

* The Offer

After doing the research for this piece, I moved some of my money into stablecoins on BlockFi, and transferred all of my (much, much smaller than 2013) bitcoin holdings to BlockFi from Coinbase. Yesterday, I was on a YouTube livestream with Ben Carlson talking about the Coinbase IPO, and unprompted, he said that he’d done the same. 

If you want to check it out for yourself, sign up with the Not Boring link to get up to $250 in free bitcoin when you fund your account. 

If you’re still wondering what BlockFi is and how it pulls off such high rates, keep reading. There’s a lot to learn. Let’s start somewhere obvious… 

What Does a Bank Do? 

Banks make money in three main ways: 

* Net Interest Margin. Customers deposit money. Banks lend that money out to other people and businesses at a certain rate, pay depositors a lower rate, and keep the difference.

* Interchange. When you use a credit or debit card at a store, the store pays your bank and its bank, typically as a percentage of the transaction and a small fixed amount. 

* Fees. Banks charge customers money when they overdraft, take money out of an ATM, and for all sorts of other things. 

For our purposes, Net Interest Margin is the most important. It’s the spread between what banks pay on deposits and what they earn on loans. Let’s do the math on a mortgage as an example.

Right now, the Annual Percentage Yield (APY) on a standard Bank of America bank account is 0.01%. Let’s assume they can lend money to a homebuyer on a 30 year fixed rate mortgage at 3.0%. Bank of America’s Net Interest Margin is 3% - 0.01% = 2.99%. 

It’s not that banks want to pay next to nothing on deposits. It’s just that with low rates across the board, banks aren’t able to pay much more and make enough net interest margin to pay for overhead and still generate enough profit to keep shareholders happy. When they could lend money at a higher rate (30-year mortgage rates were 18% in the early ‘80s), savings accounts paid higher rates too. 

Banks would love to pay high interest rates on deposits. Banks compete with all of the different things you can do with your money -- buy a house, stocks, or crypto, pay off loans, travel. The higher the interest rate, the more likely you are to keep your money sitting there. More money sitting there means the banks can lend more means higher income for the banks. Given the low rates they earn from borrowers, they just can’t.

BlockFi, however, can. 

Meet BlockFi

Founded by Zac Prince and Flori Marquez in 2017, BlockFi is a crypto-native financial institution. But while B…

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Hi friends 👋 ,

Happy Monday! This is a big one for me: Not Boring’s first birthday.

Instead of writing about a very big company, which I normally do on Monday, I’m writing about a very small one: Not Boring. It’s been a crazy year, I’ve learned a ton, and it’s just going to get better from here. But it was not at all obvious that this was going to work out a year ago.

Before we get to it, I just want to say a big thank you. Nothing in this story would have happened without you reading, commenting, conversing, and sharing. I feel very lucky that you’re willing to take time out of your day to read what I write.

If you want to bring some smart, curious friends along for year two:

Today's Not Boring is brought to you a Not Boring Day One-er

Fun Fact: Public was the first company ever to sponsor multiple Not Boring newsletters. They sponsored Knock Knock. Who's There? Opendoor. and have been with us ever since.

Public and Not Boring are a perfect match: like Not Boring, Public makes the investing conversation fun. Public is an investing app AND a social network for talking about business trends, and the social features make it easy to share ideas.

Thank Public for making Not Boring possible by hitting the link below and joining me over there. If you want to transfer your account from somewhere else, they’ll even cover the fees.

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A Not Boring Adventure, One Year In

This has been the wildest and most rewarding year of my life, both personally and professionally: our son, Dev, turned 6 months old yesterday, and Not Boring turned one on Friday. 

A year ago, we knew that Dev was coming, but I had no idea what I was going to do. I had quit my job, launched an in-person company that got crushed by lockdowns (and was probably a bad idea anyway), and to top it off, I caught COVID the week I decided to start writing Not Boring. I was lost. 

Somehow, since then, with all of your help, I’ve built my dream job. Over the past 365 days, I’ve:

* Written and sent 417k words. That’s more than all seven Chronicles of Narnia. 

* Grown from under 500 subscribers to over 42,000.

* Run a syndicate which has invested nearly $2 million in fourteen companies. 

* Generated more revenue than I’ve ever made in a full-time job. 

I legitimately didn’t believe this was possible. I would see people with big followings on Twitter or big subscriber lists and think that they had some special je ne sais quoi. I still think that it could end at any moment. 

Today, I want to share the Not Boring story as honestly as possible -- it often looks way easier from the outside -- with lessons I’ve learned on writing, growth, business models, investing, and creator psychology sprinkled in. We’ll cover:

* Getting Here: Per My Last Email → Not Boring Club → Not Boring

* Growth: Luck, Shares, Ups, Downs and Tommy

* The Writing Process and Psychology

* Business Model: Optimize for Growth and Opportunity

* The Not Boring Syndicate

* The Present and Future of Not Boring

If anything in this story seems planned, premeditated, or in any way clean, that’s just my brain going back, filling in gaps, and connecting dots. As much as I write about strategy, this story is about working hard even when it seems silly and following serendipity. 

My biggest lesson so far: this is neither as impossible nor easy as it looks.

The Winding and Uncertain Road to Not Boring

Per My Last Email

I’m cheating a little when I say that it’s Not Boring’s one year birthday. I wrote a different newsletter -- Per My Last Email -- for almost a year before. 

In early 2019, the board at Breather, where I worked, had just brought in a new CEO, who himself was in the middle of bringing in a new, experienced executive team. 

A couple weeks into the new regime, Ben Rollert (then VP, Product at Breather, now CEO at Composer) and I presented at an exec team offsite about the need to differentiate and dig moats in an increasingly crowded and bubbly flex office market. We got cut off halfway through with something to the effect of: “Moats? This is a big market, we don’t need to worry about moats. We have a brand. That’s what Apple has.” 

I realized that my brain was going to shrivel up and rot if I didn’t do something. Ben’s always been smarter than me. He saw the writing on the wall and quit. I couldn’t quit right then -- I managed a 150 person team and didn’t want to abandon them -- so instead, I used my annual learning & development budget to take David Perell’s Write of Passage course.  

That was one of the best decisions I’ve ever made. One of the assignments for the course was to launch a Substack and get twenty people to subscribe. I reserved packym.substack.com, named it Per My Last Email, and begged my few hundred Twitter followers to sign up:

Two days later, I had 28 subscribers, and we were off to the races. I wrote Per My Last Email on the side, spending a few hours each weekend or early in the morning curating links to essays, books, podcasts, and videos with a dash of commentary. It grew to about 400 subscribers in eleven months. It didn’t make a dollar and I didn’t expect that it ever would. 

But I had always told Puja and my family that if I ever got really rich and retired early, all I’d want to do is read and write and talk to really smart people. Per My Last Email let me start doing that in a small way. As someone who’d been so singularly focused on work for a decade, it felt good to have a hobby. 

Lesson: Make room for hobbies, even just a few hours a week. 

Not Boring Club

Writing was also a way for me to test out a startup idea I had in a really lightweight way. 

The idea was Not Boring Club: a mashup of social club and continuing education, Soho House meets college extracurriculars for busy grownups. 

I wrote about education and IRL Member Communities to make sure there was a real opportunity. One of the problems with being good at writing is that you can convince people that bad ideas are good. You can even convince yourself.

In October 2019, I quit Breather to start it. I wrote business plans, memos, started a debate club, made decks, built a website, and tried to write my way into a business model. I couldn’t quite figure it out. I knew what I wanted to exist, but the business model wasn’t clicking.  The people around me -- my sister, Puja, even my mom -- tried to gently tell me that this wasn’t it. They were, in hindsight and in the back of my mind even then, so obviously right. 

But I persisted, and announced the launch in a blog post. Thankfully, I didn’t raise money or sign a lease. Instead, I decided to start experimenting with a Slack group and a series of in-person events. By February, I started onboarding the first 150 (free) members with a series of small group dinners. On March 10th, we had to “postpone” a welcome dinner. Then a Debate Club. Then the next dinner. Then the next dinner.  

We quickly moved Not Boring Club online with cocktail making classes, lightning presentations, book clubs, and trivia nights. One day, I was frantically making slides for that night’s Trivia Night. Puja kind of gave me a look, and I realized how fucking ridiculous it seemed. How fucking ridiculous it was. That night, eight people showed up to play trivia. 

That was the final straw. I needed to do something different, but I couldn’t figure out what. One thing I knew for sure: I was a terrible online community leader, and I kind of hated it. If I’m being honest, COVID was a good excuse to erase my mistake. The Not Boring Club went on the back burner. 

Lesson: Don’t be afraid to admit that something you thought was a good idea turned out to be a bad idea. You’ll know it in your gut. Trust that instinct and …

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Today’s Not Boring - the whole thing! - is brought to you by… Secureframe

Secureframe helps companies get enterprise ready by streamlining SOC 2 and ISO 27001 compliance. If you don’t know what that means, I’ll explain. If you do, talk to them:

Hi friends 👋 ,

Happy Thursday!

It’s been a wild week for Not Boring Deep Dive sponsors. Following up on MainStreet’s $60 million Series A a few weeks ago, news came out about two more Deep Divers this week:

* Ramp: On Monday, The Information reported that Ramp raised $65 million from D1 and others at a $1.1 billion valuation, followed immediately by $50 million from Stripe at a $1.6 billion valuation. When we did the Ramp Deep Dive in December, they had just raised $30 million.

* Pipe: Yesterday, TechCrunch reported that Pipe raised a fresh round of $150 million funding at a $2 billion valuation. When we talked about Pipe in October, they had raised $66 million total.

The bar I use for whether I write a Sponsored Deep Dive on a company is whether I would invest my own money in the company if given the chance (disclosure: I invested a small amount in Ramp, MainStreet, and Pipe after writing about them). You can read more about the Deep Dive selection process here.

Today’s Deep Dive Sponsor, Secureframe is fresh off an $18 million Series A itself. I think that’s just the beginning. They make companies more secure, and security has never been more critical.

(I always tell you how I’m paid for Deep Dives — CPA, CPM, or equity. Today is CPM).

Let’s get to it.

This is How They Tell Me Secureframe Saves the World

Let’s start with a riddle. What do Ukrainian accounting software, Southwest Airlines, and Secureframe have to do with each other? 

Any guesses? No? I’ll give you a clue. Secureframe is security compliance software that companies, from 3-person startups to enterprises, use to automate SOC 2 and ISO 27001 compliance, complete audits, and continuously monitor their security. It’s how modern software companies stay safe and compliant with less time, effort, or cost, so they can unlock sales and focus on growing their business. 

But what does that have to do with Southwest and Ukraine? Read on to find out.

This is How They Tell Me the World Ends

Remember the old Southwest Airlines commercial in which a bored employee clicks on an email titled “Sick of your job??” and infects her whole office? Wanna get away? 

It actually sums up why cybersecurity is so petrifying: all it takes to take down a system is finding and exploiting the weakest link. One employee opening the wrong file can infect an entire company’s network; even worse, in an interconnected world in which every company runs on top of a stack of other companies’ software, one employee ignoring a software update can bring down major companies all around the world. 

In This is How They Tell Me the World Ends, New York Times cybersecurity reporter Nicole Perlroth recounts the story of the most damaging cyber attack to date: NotPetya. (Wired tells it here if you don’t want to read the whole book). 

On Wednesday June 27, 2017, the day before Ukraine’s Constitution Day, hospitals, banks, ATMs, power plants, the government, and practically all businesses in the country were hit, seemingly simultaneously, with what appeared to be ransomware. It locked computers, deleted files, and spread at breakneck speed from computer to computer, and company to company. Messing with Ukraine on its Constitution Day had become a Russian hacker pastime -- Ukraine’s neighbor routinely shut off the power or deleted files -- but this was different, more vicious. It was also harder to contain. 

NotPetya spread via “two exploits working in tandem”: EternalBlue and Mimikatz (technically, Mimikatz is not an exploit but an application used to take advantage of the EternalBlue exploit). EternalBlue was a backdoor into any unpatched Windows computer, and Mimikatz used those computers to steal passwords and break into others. Together, they preyed on the weakest links. 

The virus was so hard to contain that it jumped from Ukrainian companies into any company that had an office or even an employee in Ukraine. NotPetya took down systems at: Danish shipping giant Maersk, American pharmaceutical behemoth Merck, FedEx’s European subsidiary TNT Express, and even boomeranged back on Russian state oil company Rosneft. Once the virus was unleashed, there was no stopping it. 

And it started by finding a weak link, or more precisely, a weak Linkos. 

Linkos Group is a small, family-run Ukrainian software business that makes M.E.Doc, a tax product that’s like a Ukrainian TurboTax or Quicken. Practically anyone who does business in Ukraine uses M.E.Doc. That’s how the Russians got in. According to Wired: 

In the spring of 2017, unbeknownst to anyone at Linkos Group, Russian military hackers hijacked the company’s update servers to allow them a hidden back door into the thousands of PCs around the country and the world that have M.E.Doc installed. Then, in June 2017, the saboteurs used that back door to release a piece of malware called NotPetya, their most vicious cyberweapon yet. 

All told, NotPetya did over $10 billion in damages, according to a White House assessment. It’s an extreme example, one of the most devastating cyber attacks in history, and a distant one, launched halfway around the world. But the book is chock full of other examples, big and small, of hackers, private and state-sponsored, finding their way into the networks of the largest companies and richest governments. 

Cyber is the new global battlefield, but unlike traditional warfare, it’s much harder to contain the impact to specified targets, as NotPetya showed. Now, companies are often casualties of war. They fall victim to civilian and state-sponsored hackers alike. 

All of those hackers are constantly looking, or paying, for a way in. They form a global, multi-billion dollar, public-private market for weak links. 

How Not To Be the Weak Linkos

OK, did you solve the riddle? 

If M.E.Doc and the woman in the Southwest Airlines commercial were Secureframe customers, they wouldn’t have unleashed malware on their co-workers or customers.

Chances are, your company isn’t going to be the weak link in the next NotPetya. But if you’re building a software company of any size, you need to care about security.

In order to sell into enterprises, companies need to prove that they’re secure. After reading the NotPetya story, the reason why should be clear: enterprises can’t afford to let in weak links. 

Previously, this prevented smaller companies from selling into larger ones early in their lives. “Bottoms-up” or “product-led” growth is in part a response to slow enterprise sales cycles, which are slow in part due to each enterprise’s bespoke security compliance requirements, which could take months and tens of thousands of dollars to pass, for each company. 

Over the past couple of years, though, a standard called SOC 2 has emerged as the de facto security compliance standard. Since SOC 2 is generally accepted as the gold standard, getting SOC 2 certified means that you can sell into large companies much earlier. That’s a huge revenue unlock for young companies. SOC 2, the humble security compliance standard, is partially responsible for sky-high early stage valuations.  

Today, most software companies are SOC 2 compliant by the time they hit 20-30 employees, with some even getting it when they’re just three people. In a competitive environment, they can’t afford not to be. If your competitor gets its SOC 2 and you don’t, they have free reign to scoop up large customers while you’re stuck down-market. 

But even though SOC 2 (and a host of sector-specific standards like PCI, HIPAA, and FedRAMP) level the playing field by eliminating the n…