How to Find Your Personal Monopoly - Part 1

Lessons from watching 250 peers on the journey

Loomings

In 1993, I wrote my college thesis on Moby Dick and never thought about it again. But in the summer of 2021, I started to recall the opening chapter. I was like the restless Ishmael, ready to knock hats off of people and walk behind funeral processions. 

My head hurt from the divisive voices and rising tribalism in the world. I imagined renting billboards to deliver messages the world needed to hear. Professionally, I wanted a change. I’d spent 20 years helping founders identify their best opportunities. I helped them navigate or jumped in as CEO. But now, I wanted to work on a vision of my own.

If it were 200 years earlier, I would have loaded up the wagon and headed west. But it was 2021, so I headed out to the online frontier. I signed up for a 5-week online writing course that turned into a 2-year journey. 

Longings

Many chapters in Moby Dick are tedious. This next section may feel that way for readers who haven’t spent time staring at the stars and black holes of Twitter and other social platforms. Those readers should feel free to skim or skip to the last section. But if you know what it’s like to stare at the online game and want to play, read on.

In 2014, I started logging into Twitter daily to help build an audience for our early-stage startup. If you watched me, you’d see me spend a few minutes trying to draw attention to the company before consuming the curiosities and expertise shared by other people.

You wouldn’t see my faint feelings of envy and frustration as I logged in. I wanted to be like venture capitalist Andrew Chen, for example, who would periodically ask if anyone could introduce him to X person, share Y data, or take 10-15 min to explain Z topic to him. Like magic, he’d obtain in an hour or two what he wanted and cancel the request

I’ll never forget when Andrew tweeted and asked if you’d rather have $1 million or 30,000 high-quality followers. I instantly answered in my head: 30,000 high-quality followers. The majority of comments shared that view. 

Andrew created $1 million in value just by sharing his observations and insights to attract what he wanted: more startups coming to him for investment, information for faster decision-making, to potential hires for his portfolio companies. 

There was also emotional and social value. People with accounts like Andrew’s could, in the morning, announce they would be in a different city that night and ask if anyone wanted to meet up. Later that evening, they’d post photos from the impromptu bar gathering or small dinner party that had taken place. These internet strangers had become friends in real life.

This all felt like another dimension of time and space. This phenomenon extended beyond venture capitalists and startup founders. Every topic seemed to have emerging niche experts. These people all employed the model of giving more value than they received.

I continued to watch but couldn’t give it a name.

The Personal Monopoly

In 2018, Erik Torenberg started discussing Personal Moats for one’s career. The idea was to stack skills into a unique combination that made you the most desirable person for a role. The more specialized your role, the more value you can deliver and compensation you can demand. 

A few months later, David Perell stopped me in my tracks. He called them personal monopolies. 

Perell understood how someone like Mr. Beast was the perfect example of the Creator Economy, where an individual creator could leverage the internet’s global size and lack of gatekeepers, along with new distribution platforms and monetization models, to create more than just a personal brand.

Perell focused most of his attention on people like himself, writers who lived in the world of ideas. He described how you could write online to share your unique wisdom and be recognized as the go-to expert. Your niche expertise came from a combination of experience, interests, and personal qualities. You’d have virtually no competition because no one else can offer what you offer, in the way you offer it. 

I read David’s writing multiple times. The term was irresistible to my brain. “Personal” meant something I owned and controlled. “Monopoly” conveyed freedom, financial security, and influence. A personal monopoly enables you to be you and is the real estate from which you launch a future product niche or brand.

I sighed with relief. I understood the concept and had the instructions to find and build my own.

Failure to Launch

I knew I could use my startup background to opportunistically plant a flag, create a personal brand, and seek “riches in the niches.” But even if I could keep boredom away, eventually it would arrive, and I would either be trapped performing for my audience, or I would abandon them as my attention moved on. 

I also realized that a personal monopoly was more than an economic concept in the accelerating creator economy. It was about finding that place in your heart and mind where you wanted to live for the next 10-20 years.

As much as I loved and understood the concept of the Personal Monopoly, two years went by, and I never saw an intellectual castle with a moat I believed I could or wanted to own for the long term. The startup landscape felt crowded. Marketing concepts I breathed every day, like targeting-positioning-messaging, felt limiting. 

The situation was maddening, and self-doubt crept in. I was the person people called to troubleshoot their product marketing and sales problems. VCs and PE firms called me to help their CEOs explore new strategic opportunities. Why couldn’t I figure this out?

Purchasing Rocket Fuel

Shortly after coining the term, Perell launched an online writing course called Write of Passage. He promised to teach people how to write online and build an audience. I remember my skepticism that one needed to take a course, let alone pay a lot of money.

Two years later, I finally swiped my credit card for the course which now costs as much as a class at Harvard. I rationalized I wanted to be a rocket, and rocket fuel isn’t cheap. I also hated spending money and knew I would do the work. 

At the Launch Pad

The course ended, and I had a website, three published essays, and enough knowledge to earn my space commander certificate.

All I needed to do was hit the big red launch button and keep writing and publishing to fuel my journey. But I still didn’t have the destination coordinates of my personal monopoly, and I don’t do random.

I wanted something sustainable that would generate income and was 100% aligned with my interests, curiosity, and emotions. But saying this felt dangerously elusive and akin to following your bliss, finding the work you love, or some other eye-catching book title you’d find between the career and self-help sections.

In the weeks that followed, I drafted multiple essays on random topics that hit me. They all felt self-indulgent and many held semi-veiled rants. The world didn’t need more of this. I remember gathering the topics and looking across them, hoping they formed a telescope to show a glimpse of heavenly personal monopoly light. What a cosmic joke. It didn't even reveal the next writing topic or the next steps to take. 

Meanwhile, I watched with frustration, envy, and happiness as classmates’ personal rockets lifted off one by one. I didn’t want to fail because I had already invested significant time and attention. Eventually, I knew nothing I published could feel worse than not publishing. It would be less reckless to act than to remain idle. 

I finally said fuck it and pressed the big red button.

Taking the Journey

I started writing the first of 20 newsletters. Publicly, it was a vehicle for me to simplify complex topics and show positive and curious things in the world. Privately, I wanted to build a writing habit, see how people reacted, and see what serendipity and value followed. 

Each newsletter took a grueling 6-8 hours to write because I was new, and multiple things could get in the way. But by the 5th newsletter, I enjoyed writing it. By the 10th, I sensed I would make it. And by the 20th, I felt like I was floating freely in low earth orbit. 

I had reached a new stage that felt lighter and easier. 

Old modes of thinking and emotions had lost their gravitational pull. True fan subscribers had helped me understand the value they derived from my writing. But I didn’t sense the newsletter would take me where I wanted to go. So I stopped writing. 

It felt like quitting, but my attention and energy had shifted. During the 6-month journey and now in this new space, something curious was happening with growing frequency. 

A Telescope for Others

I regularly spoke with classmates and internet strangers who were on similar journies.

Regardless of the planned topic, I always played a game in the background. Before the call, I looked at their LinkedIn profile and read their writing. During the call, I listened to what they said. It didn’t take long for me to spot unique qualities about them.

In the first weeks of the Write of Passage cohort, I spoke with Christine Carrillo. A few days later, I sent her a note saying she was the 10-Hour CEO. I spoke with John Nicholas and blurted out he was the Accidental Actuary. At times this felt obnoxious. I worried that sharing the lights going off in my mind might interfere with their own discovery process. But no one hung up and most calls ran longer than expected.

They described what they saw me doing and how it helped. A woman said I was like a flashlight shining on the path she’d been walking in the dark. Several people said I gave them 10X or 100X visions of their future selves.

The conversations helped them clarify their thoughts and emotions. This reduced the amount of blind faith required to keep going and created space for easier, more natural writing.

For me, what felt effortless was more fun and emotionally rewarding than anything I had done before. The people I spoke to had significant experience and wanted to help the world in their own unique way. Each person was like a high-potential startup that wanted to solve a meaningful problem.

Look Backwards to Connect the Dots

Over the past two years, I’ve helped 250 students in countless Zoom sessions with DMs in between:

• March 2022 - Returned to Write of Passage as Personal Monopoly mentor

• May 2022 - Launched my own 5-week Personal Monopoly Accelerator

• September 2022 - Entrepreneur-in-Residence at Write of Passage for 6 months 

• October 2022 - Personal Monopoly Mentor

• Dec to Feb 2023 - Ran a later-stage Creator Accelerator within Write of Passage

• October 2023 - Personal Monopoly Guest Speaker, Write of Passage

Looking back, this all makes sense. I was using the same muscles I’d built over 20 years to identify the best market opportunities for complex software. I’d figure out the uniqueness of the product and its value to different user types. Once clear, we’d choose the highest potential segment and develop an approach to attract customers. 

But what I was doing felt more meaningful and personal. I was helping people who had much to give to the world. My legacy would come from helping produce their dreams.

I don’t have a personal monopoly yet. But I have the coordinates for the next waypoints on the journey. And I have a monopoly-building engine to get there.

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Advice for Liftoff to Low Orbit

So you’re probably muttering, “Ok, Captain Space Metaphors, nice story about how your personal monopoly emerged. What about mine?” Here are first steps to take:

1. Collect yourself. You’ve forgotten how much you know, what you’ve done, to who you’ve helped. Start gathering feedback the world has given you: performance reviews, thank you notes, requests to help, to anything resembling a compliment. Notice what catches your attention and imagination. Pay attention to the books you buy, the people you stare at with envy, to your browser and AI chat history

2. Write to clarify and reveal. You’re currently held in place by known and unseen forces. You need to surface history and memories and connect ideas and emotions. Call this woo, therapy, healing, or any other name. It’s the job to be done. The writing topic in the early days almost doesn’t matter as long as every piece contains observational left-brain writing and personal and playful writing. This is what will free you from gravitational forces.

3. Publish to recruit the helpers, mentors, and patrons on your journey. You can not find your personal monopoly on your own. You will need true fans and people who love you to describe what they see. The only way is to publish so the universe will notice and strangers will knock at your door. You must have live conversations with them and ask why they like your writing. These early true fans will feel like angels. They will tell you what they like about your writing. Of course, they're also telling you what they like about you. They will help you see a future vision of yourself. It might be an image you never considered, or they're confirming something you've felt deep down but never articulated. 

4. Help others from your most natural, authentic self. Your motivation to write can be 99% for yourself, but you need to reserve 1% for helping the world. For example, you may write about a difficult situation that enables you to process it. But by sharing it, you will provide a massive unlock for someone in pain today. As you keep writing and sharing, your writing will help more people. If monetization is important to you, you’re building toward a coaching business, a course, a product, a community, a mastermind, or another monetization option. 

5. Every space program has a support team. You want to have peers, editors, and partners wherever you can. You’ll need help on the journey, whether getting off the ground, objectively monitoring your progress or grabbing you when you’re tempted to jump out as your rocket violently shakes and rumbles on its way to low orbit. 

If you found this useful, please like, comment, or reply to let me know. I plan to write more on how to move faster towards your best opportunities.

P.S. - I’ve launched a cohort-based course called Personal Cartography. You can learn more about it here.

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Huge thanks to the first round of editors in April. Their comments motivated me to stick with it and many of their questions will be the next writing topics. Thank you, Nic Rosslee Kath’s Substack Latham Turner Dekera Greene Rodriguez Alan Hibbard Jordan Boucicaut

It was hard to finish this essay with 200,000 unpublished words on the topic stirring through my brain. Eternal gratitude for these talented, helpful souls: Michael Dean Yehudis Milchtein Michael Ashcroft Simone Silverstein

Lastly, I owe much to the 250+ people who took the time to share their experiences on the journey with me. Thank you.