A Very “Different” Approach To A Legendary Career: YOLO And Achieve Your Personal IPO

Arrrrr! 🏴‍☠️ Welcome to the free edition of Category Pirates. Every Wednesday, we publish radically different ideas with the goal of helping you create, design, and dominate your own category—in business and in life. If you enjoy this letter, we encourage you to check out some of our other favorites:

  1. Miami & Austin Are Wreaking Category Violence On Silicon Valley

  2. Tesla Superconsumers Are Making Millions—Because They Have An Information Advantage Wall Street Doesn’t

  3. The Value Of Bitcoin Most People Can’t See

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Dear Friend, Subscriber, and fellow Category Pirate,

In 1975, the Wall Street Journal ran what is now considered one of the greatest marketing promotions of all time.

It was a sales letter called “The Tale of Two Young Men.” Between 1975 and 2003, this sales letter generated more than $2 billion worth of Wall Street Journal subscriptions. Start to finish, the letter is just under 1,000 words.

It opens with a short tale that goes like this:

“On a beautiful late spring afternoon, twenty-five years ago, two young men graduated from the same college. They were very much alike, these two young men. Both had been better than average students, both were personable and both—as young college graduates are—were filled with ambitious dreams for the future.

Recently, these men returned to their college for their 25th reunion.

They were still very much alike. Both were happily married. Both had three children. And both, it turned out, had gone to work for the same Midwestern manufacturing company after graduation, and were still there.

But there was a difference. One of the men was manager of a small department of that company. The other was its president.”

The letter goes on to explain that the difference between the two young men was that one had access to information the other one didn’t. The young man who went on to become president of the company read TheWall Street Journal. The other, the small department manager, did not.

We love this story. But 1975 was a long time ago, and we would tell it differently today.

We would call it, “The Tale of Two Young Women (And A Pirate).”

On a beautiful late spring afternoon, in the foothills of Silicon Valley, two young women graduated from the same college. They were very much alike, these two young women. Both had been better than average students, both were personable and both—as young college graduates are—were filled with ambitious dreams for the future.

They also had a friend, named Pirate Jane.

Recently, the three of them—the two young women with college degrees, and Pirate Jane—returned to their college for their 25th reunion. Actually, the two young women went to the reunion, and Pirate Jane met up with them afterwards at a bar down the street called Whiskey Waters.

The two young women were very much alike. Both were happily married (at least, that’s what they told the neighbors). Both had three children (although it’s worth noting they called their third kids “surprises”). And both, it turned out, had gone to work for the same technology company after graduation, and were still there.

And there wasn’t much of a difference. Sure, while one was manager of a small department, and the other was president of the company, both had the same number of vacation days. Both had to show up to the office at 8:00 a.m. and were expected to stay until at least 6:00 p.m. And both had a limited amount of agency and freedom over their time, long-term earning potential, and personal autonomy. Aside from the modest gap in their earnings (noticeable, but certainly not astronomical), their lifestyles were nearly identical. They even both drove Teslas.

And, it should also be noted, were avid readers of The Wall Street Journal.

“You need to put that paper-pushing, incremental improvement wahooligarchy babble aside,” Pirate Jane yelled, slamming her mug of craft IPA down on the warped walnut bar. “If you’re a candidate, you’re a commodity. Commodities can easily be traded. And if you have any hope of escaping that rat race (never forget the sage words of Lily Tomlin, ‘The trouble with the rat race is, even if you win, you’re still a rat.’), then what you need to work toward is a Personal IPO.”

Welcome to the YOLO Economy.

A few weeks ago, the New York Times published an article about how exhausted, type-A millennial workers of America are quitting their jobs in search of more personal freedom.

This is yet another one of the stunning effects the pandemic has had on society. It has led millions of people, all at the same time, to ask themselves, “Why do I do what I do? Why do I live where I live? Am I making a difference? How do I integrate my personal and professional life? Does my work matter?” These are seminal life design questions—to which many are concluding, “Screw it—YOLO” and quitting their jobs altogether in search of meaning.

The New York Times named this phenomenon the “YOLO Economy,” (YOLO being an acronym for “You Only Live Once” originally made popular by Grateful Dead drummer, Mickey Hart, and more recently, Hip-hop phenom, Drake.) In the piece, NYT interviews characters like Brett Williams, 33, a lawyer in Orlando, Florida, who have come to the “YOLO epiphany” that spending ten hours a day on Zoom calls at his kitchen island in the name of a paycheck was, to put it lightly, miserable. Instead, he and many others are trading in their salaries and benefits for gig-economy jobs, choosing autonomy and personal agency over job security, corporate credibility, and retirement plans—all things we’re told to strive for early in our lives (and whom many take out five or six figures worth of college debt to pursue).

The NYT article goes on to share some startling statistics about how prevalent this mentality is in today’s working America. 

According to a study by Microsoft, more than 40 percent of the global workforce is considering leaving their employer this year. And according to Blind, an anonymous social network popular among tech workers, 49 percent of its users are planning to land a new position in 2021. A good job, nice car, steady paycheck, and white picket fence are no longer enough. In the words of Loverboy, many are done “Working for the Weekend.” 

Instead, what people want is agency, choice, freedom and meaning. What people want is to be the captain of their own soul, the author of their own destiny. 

What people want is to be Pirates.

Your Personal IPO

This desire for personal autonomy has been around for a long time. It’s a foundational human drive. 

Even before the pandemic, we were writing about how high performers were quitting big companies to work for themselves. The reason is because, eventually, you come to realize that regardless of how high you climb up the corporate ladder, your future is at the mercy of someone else. 

We call this journey working toward your “Personal IPO”: A strategy for finding deeply meaningful work and living a happy, successful, and highly profitable life.

The same way a startup strives to one day achieve a liquidity event, we believe every ambitious worker strives for (and/or eventually realizes the power of) a personal freedom event—whether that means quitting your job and going solo, or hopping aboard someone else’s ship who values your future with a higher multiple. This is the day when you become responsible for your own livelihood, and unlock a world of opportunity, agency, and earning potential that is otherwise impossible taking incremental steps forward in the conventional working world. The question is how to obtain personal agency without driving Uber or delivering Postmates 60 hours a week in order to keep paying the bills.

To be clear, what we are talking about is not a “4-Hour Workweek” for travel-obsessed Millennials, or a Eat, Pray, Love moment for anyone successful but unfulfilled and in need of a retreat to Italy, India, and Indonesia before turning back to the corporate world with a newfound zest for life. 

The fact of the matter is many women and men of every race, religion, and socioeconomic background spend their entire lives thinking they’re on the right path, the “elite” path—Wharton MBA, high-paying job at McKinsey—only to realize five, ten, twenty plus years later, “Wait a minute, I’m still an employee. Someone else cuts my check. And while I might be a ‘Successful Professional,’ all of a sudden that doesn’t seem as good as the lower-rung Pirate who has freedom over their life.” (We know ski bums who “scrape by” but have more joy and agency than some of the CEOs we know.)

Hence today’s YOLO Economy.

The Personal IPO Formula

In order to successfully take control of your life and career, while achieving agency, you don’t need A’s in school—especially in today’s digital-first world. (Pirate Christopher didn’t even go to school! And Pirate Cole failed math and science but got a degree in fiction writing!) 

What you need are answers to these three questions:

  • How much is agency worth to you? 

  • Who is your Archimedes?

  • Who is your auctioneer?

Let’s dig into each one.

How much is agency worth to you?

This is test number one—the fight within yourself. How much do you care about personal freedom? What are you willing to give up in order to obtain in? Be honest. Because it means the buck stops with you. And the reality is, some people don’t want that level of personal responsibility. They want to be taken care of. They would rather stay “safe,” stuck in The Matrix. 

“There can be no joy in living without joy in work.”—Thomas Aquinas 

See, those who declare dominion over their work are different. They are working for something greater than a paycheck, 14 days off, and the occasional raise. They view work as the reward, in and of itself, and proactively design their life accordingly. Furthermore, they are not trying to get “work-life-balance,” because when you love what you do, you have nothing to “balance.” Instead, they start with work that matters to them—and then work toward increasing their point of leverage and monetizing their potential.

Who is your Archimedes?

Archimedes said, “If you give me a lever and a place to stand, I can move the world.” This is what the vast majority of people fail to understand about personal freedom and career autonomy: you don’t need the whole world to approve of your decision. Most of the time, all you need is one supporter, one client, one customer, one opportunity (“to seize everything you ever wanted”).

You need to find your Superconsumer. Because they will find other Superconsumers and bring the market to you. 

For people striking out on their own, this could be your first customer, client, or investor. For people seeking agency in more traditional careers, it is often a senior mentor or someone who hires you into a new job. It’s a sad fact that many people have to change companies and roles to achieve their Personal IPO and experience a meaningful jump in responsibility and compensation—because people who know you and have worked with you for a while tend to see you through the lens of who you were and who you are now, not who you could be tomorrow. 

And too many employers value you based on your past, not your potential. 

Who is your auctioneer?

If you’ve ever gone to an auction, then you know the auctioneer sets the price. Well, in your own life, who is your auctioneer? If you’re a candidate for a job with no point of leverage, then your auctioneer is the person hiring you: “For this role, we are willing to pay $65,000 per year.” If you’re a candidate for a job with a former coworker or someone on the company’s leadership team, then that person becomes your auctioneer: “They won’t take anything less than $150,000.” And if you’re setting out on your own, your auctioneer is probably a friend, mentor, family member or former coworker. And depending on who that person of influence is in the context of your life will reveal where they are on the Personal IPO journey and who their auctioneer is: “There’s no way someone would pay you that!” vs “You need to charge 10x more!”

The auctioneer advocates to the audience for you, and helps frame how and why you are different. The auctioneer also sets a minimum price that is higher than people expect, because the auctioneer is there to help you get the highest price for the value you will create. 

Sometimes you have to be your own auctioneer. 

You need to dig deep, look someone in the eye and say, “That will be <insert large dollar amount that makes you scared to ask for here>”. 

So, come to terms with the price you’re willing to pay for agency, find your Archimedes, and name your auctioneer, and arrrrrrrr! you’re a Pirate.

How To Change Out Your Investor Base

In our last letter, we wrote about the impact Superconsumers can have on the growth and profitability of your business.

Well, the same logic applies to your Personal IPO.

The key to unlocking agency and financial freedom in your life is by changing out your investor base from people who buy on past performance (your former employer) to people who buy on potential (and the people who buy on potential pay a lot more than people who buy on past performance—à la the startup giving you a nice chunk of equity, or the big box retailer willing to take a chance on your new, bootstrapped product). 

Said differently, you’re swapping out “value investors” for “growth investors.”

Now clearly, quitting, going solo, and/or becoming an entrepreneur are the “purest forms” of career agency. But, you can still create a high degree of personal and financial freedom when you shift your mindset about what “work” means to you. The way you view yourself, your role, and where it is you want to be in 5 or 10 years, matters. And the words you use to describe the work you do, matters. 

Because often what we tell ourselves, about ourselves, defines ourselves. 

So, who are your current “investors” in your personal life, and what kind of investors are they?

More importantly, who is determining your valuation right now?

  • Parents? Some parents undervalue their children (“If you can just get a good government job, that’ll be great.”) and some overvalue their children (“You’re going to become the next President of the United States!”). Depending on the level of influence your parents have in your life is also going to determine the way in which you value yourself and perceive what is possible for your future.

  • Peers? As the adage goes, you are a reflection of the five people you spend the most time around. Are your friends comfortable in their corporate jobs and happy with their 14 days of vacation time per year? They’re probably going to have a hard time understanding why you would want to give up your fancy job title to hop aboard a ship full of Pirates. On the other hand, if you are a freshman at Stanford and your roommate just flunked Chemistry but sold his dorm-room startup for $10 million bucks, that’s either going to motivate the hell out of you or begin a vicious cycle of comparison.

  • Mentors? The people who see your potential, foster it, encourage it, and maybe even invest financially in it are the ones who end up shaping your definition of success. If those people think small, you will learn how to think small like them. If those people think big, you will raise the roof to meet their expectations. 

Most people live a life dependent upon “value investors.”

Employers are value investors. Parents, family friends, and the Jones’ next door tend to be value investors. This starts as early as high school with ACT and SAT scores, extracurricular activities, the number of semesters you spend on the Honor Roll, and the almighty resumé. Your future is based on your past—and if your past isn’t “good enough,” then the assumption is your future won’t be much better.

This teaches people to enter the working world with a mindset of “competition.”

They see their identity and value in relation to someone else. As a result, they spend much of their adult life following trodden career paths that lead to clearly defined, but less exciting (and less exponential) outcomes. The journey begins at 25, ends at 65, and then you can enjoy your life. Retiring is the Personal IPO in this world, and the price you pay is 40 years of labor.

Growth investors are very different.

This group of people includes the crazy uncle who dropped out of college to start his own business, the former boss-turned-mentor who always said, “Just keep following your curiosity—it’ll lead you somewhere valuable,” and even our irrational mothers who think everything we do is amazing. (Pirate Christopher’s Grandfather told him he was the, “Bestest boy in the world.”) 

These are the people who are completely unconcerned with what you’ve done, and entirely focused on where you’re going. They’re betting on your long-term potential. And certainly not just economically, but intellectually, psychically, and emotionally. They want to go with you on the journey. They want to be part of what you create and discover. And they derive significant joy from encouraging you along the way.

Find these people in your business and your life, and you can change your valuation. Because regardless of whether or not you go solo, you for sure want to YOLO. 

You want to either create or join an environment betting on your future.

Not sure? Here’s a good test:

If you can count on one hand the number of people in your life betting on you, that will reveal whether you yourself are betting on your own past performance (your resumé) or your future.

Pirates hang out with Pirates.


Category Pirates

Eddie Yoon

Nicolas Cole

Christopher Lochhead

PS -- We are extremely passionate about the idea of applying category thinking to personal life design. We are going to continue exploring this topic in future letters with the goal of compiling these perspectives into a book. So if these concepts resonate, give you ideas of your own, or spark questions, please reply and let us know! We’d love to hear from you! Arrrrrrrr!