EXERCISE 1

Newsletter differentiation

CHAPTER 1: YOUR PERSONAL MONOPOLY

Write down your favourite 4 newsletters. In one sentence or less, write down what you love about each.

Do not write what they are about, but what response they solicit. It can be as simple as “it makes me smile” or
“I feel updated”. Do not overthink this.

Take your responses and try parsing them into a single adjective. For example, “it makes me smile” can be
represented as “funny” or “uplifting”. “I feel updated” effectively means “informative”. If you don’t have 4
favourites, go through a few on this list or this list and contemplate why they are loved.

Now, write down 4 newsletters that you are not longer subscribed to. Think critically about why you
unsubscribed. Was it because it stopped delivering something that you initially loved? Is it because there is now
a better option that you prefer? Do the same exercise of parsing that experience into a certain adjective, like
“spammy” or “biased”.

“Chartr” “It feels easy” “Low-stress”

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EXERCISE 2
What is my personal monopoly?

CHAPTER 1: YOUR PERSONAL MONOPOLY

Ask yourself the following questions:

• What is something that you have done that 95%+ of the population hasn’t done? Or, what unique
insight do you have that 99% of the population doesn’t have?
• What is something that you have spent 5+ years on that you can translate to others in significantly
less time?
• What is something that you could create that you would’ve loved to have exist 5 years ago?
• What is something that I think about in the shower?

Write down 5 things that come to mind.

This exercise is not reserved for individuals. Companies can answer the same questions.
For example, what are 5 things that you have insight into that 95%+ of people or companies
don’t have access to?

Next to each idea, consider what your edge would be, should you decide to write about it. Would you be
more humorous than the incumbents or more contrarian? Would you be more deeply
researched or give people what they need in less time? Would you be more relatable? Do not just write
that you will be “better”. Be specific.

You may get to some of these answers more easily by asking yourself questions like:

• What is something that McKinsey would feel uncomfortable publishing?

• How can you deliver the same information as Gartner in ¼ of the length?
• What would a complete stranger want to learn from me?
• If I were to relearn this I know, how would I like to learn it?

Personal Monopoly My Edge

“remote work” “accuracy”

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EXERCISE 3
What for who?

CHAPTER 1: YOUR PERSONAL MONOPOLY

If you have a publication already, parse the concept into a “what for who” one liner. If you are considering
what to create, take your ideas from Exercise #2 and parse them into a one liner.

I am writing...

for

I want to create...

for

for

for

for

for

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EXERCISE 4
Total addresssable market

CHAPTER 1: YOUR PERSONAL MONOPOLY

Try estimating the total addressable market (TAM) for your current or future publication. The purpose of this is not to be
perfectly accurate. It’s to get a sense of potential scale. There are many ways to go about this, but start by assessing the
competition, search volume for queries that your audience may be searching, and by checking existing communities. Try
to use multiple sources of information.

COMPETITION
1. Are there existing publications in your space? If so, how many people do they reach?
2. Do you realistically think that you’ll be able to capture less, the same, or more?
3. What assumptions are you baking into that prediction?

SEARCH VOLUME
1. Select 5 keywords your target audience would search. What is the search volume for those terms?
2. How competitive are they?

EXISTING COMMUNITIES
1. Is there a subreddit tailored to your target persona? If so, how many people are part of that subreddit?
2. Are there other communities (forums, Facebook groups, Slack channels, Telegram groups, Discords, etc) for my tar-
get persona? If so, how many people are active in them?

Given the above research, roughly how many people do you think you can reach? Does that map out to the scale you’re
looking for? Even if you don’t have an exact number, which of these buckets does it fit into? Circle your answer.

Less than 1000 Tens of thousands Hundreds of thousands Millions Tens of millions Hundreds of millions +

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EXERCISE 5
Audience personas

CHAPTER 1: YOUR PERSONAL MONOPOLY

Try to describe your ideal reader; one of your 100 true fans. If you have multiple target personas, focus on
your primary persona.

1. What are their demographics?

2. Where do they work?
3. Where do they hang out (both online and offline)?
4. What do they read?
5. What problems do they face daily?
6. How about weekly? Monthly?
7. What do they enjoy doing? What do they hate doing?

EXAMPLE
“The average reader of HBCU Digest is the middle-aged black woman who makes about $150,000 a year.
She might be on Facebook, she probably is not on Twitter, and she’s not on Instagram at all, but she is
checking her email daily. She probably lives in Georgia or Florida or Houston, Texas or Washington, D.C.”

You may be unsure how to answer some of the above questions. Here are some tools to help you.
• If you have existing readers, reach out to your most highly engaged readers and talk to them. Ask them
what they like and don’t like about your offering. Ask them what else they read online and what other
problems they need solved.
• If you have competitors online, you can use tools like SimilarWeb to see what channels they get their
traffic from.
• If you want to find niche communities, you can use this tool to search thousands of Subreddits. Once
you find a relevant one, you can go to Subreddit Stats to see what submissions have gotten the most
attention and which keywords are most frequented. In other words, you can learn more about what
your audience is interested in.

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EXERCISE 6
Distribution vectors

CHAPTER 1: YOUR PERSONAL MONOPOLY

Take a look at your persona identified in Exercise 5. Where would this person hang out? Where would
they get their news? What social channels would they be drawn to?

Write down at least 5 distribution vectors for your audience. If you cannot identify 3, how do you expect
to reach this audience?

1.

2.

3.

4.

5.

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EXERCISE 7
Select a newsletter type

CHAPTER 1: YOUR PERSONAL MONOPOLY

Determine which newsletter format is best for you and your audience. Circle your answer.

Daily Updates Long-form Digest Hybrid Pop-up

Here are some questions to consider:

1. What format allows you to solve your audience’s problems most effectively?
2. Do you have bandwidth to consistently create content?
3. If so, how often can you produce content at a high level of quality?
4. What type of content are you looking to produce? (For example: short listicles or deeply researched
pieces)
5. Are you sharing your opinion or providing resources for people?
6. Are you creating this on behalf of a company or an individual?

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EXERCISE #8
Core values

CHAPTER 1: YOUR PERSONAL MONOPOLY

1. Start by writing down all of the things that you want your newsletter to be/do, with no constraints. For
example, maybe in an ideal world, you want to respond to each and every subscriber. But, maybe you
also want to scale to 100k subscribers in your first year. Or, maybe you want to work on this project no
more than 10 hours a week, but you also want to publish daily. Write all of these things down.
2. After you write these things down, consider if any of them are at odds with one another. If they are,
which are more important? Reorder by what is most important.
3. Which items on the list are non-negotiable? Circle them.
4. Now, are any of the non-negotiables in conflict? If so, resolve these conflicts until you have a list of non-
negotiables that can completely co-exist.
5. Consider what tradeoffs you’re going to have to make. The items that moved to the bottom of your list
will give you some clues.
6. Finally, contemplate if there are any guardrails or policies that you should put in place, such that don’t
disrupt the unwritten contract you have with your audience?

MY WANTS PRIORITIZED WANTS

MY POLICIES

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EXERCISE 9
Design inspiration

CHAPTER 2: WRITING AND BUILDING

If you don’t have a site yet or want to rebuild your site, don’t start right away. Spend the next few weeks
naturally scrolling the web, but every time you see a site or a feature that you like, just jot it down and note
why.

For example, “I liked their nav bar.” “Dynamic colour scheme.” “Clean animations.” “Convincing trust bar.”

I encourage people to do this exercise because your brain isn’t built to retain a great deal of information over
time. That’s why, when someone asks you for an example of something, even though you know you have
dozens of examples, sometimes nothing comes to mind in that moment. Instead of relying on your brain to
retain pieces of inspiration—which it is trained to flush or cache periodically—write them down. You can also
look to tools like Softr or Inspireframe for inspiration.

WEBSITE I LIKE...

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EXERCISE 10
Paid or free?

CHAPTER 2: WRITING AND BUILDING

Spend some time contemplating whether you want to build a paid or free publication, with these
questions in mind:
• What are your financial goals for this publication this year? ($/year)
• Given the audience size that you projected in Exercise #4, how much would you have to make off of
each subscriber? Does that seem realistic?
• How important is scale and building a personal brand?
• How important is it for you to make money off of my publication?
• If monetizing is important, how soon do you need to be profitable?

PAID SUBSCRIBERS FREE SUBSCRIBERS

How many can

you reach in the
next year?

What will you

monetize?

For how much?

Total $/year

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EXERCISE 11
CODES framework

CHAPTER 3: DISTRIBUTION (NON-SEO)

Remember the distribution vectors that you identified in Exercise #6? Take these, or the channels that you’re
currently prioritizing for your publication, and consider how they rank across the CODES framework. Do you
have a balanced portfolio of channels? Do you have any significant bedrock? Do you trust these to be
consistent?

DISTRIBUTION
COST OWNERSHIP DEPENDABILITY EFFORT SCALABILITY
VECTOR

SEO Low-medium Medium High High effort High

cost ownership dependability scalability

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EXERCISE 12
Update your modals

CHAPTER 3: DISTRIBUTION (NON-SEO)

Take what you’ve learned about modals and either create new modals or update your existing ones.

Updates to make:

Clear value alignment (speaks to audience’s problem in their language)

Clear CTA (replace general statements like “subscribe”)
Social proof (add testimonials, “trusted by”, etc.)
Calm any concerns (free, no spam, etc.)
Remove distractions (single action)

Ensure modal coverage including:

Event-triggered
Fixed (floating bar, embedded)
Landing page

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EXERCISE 13
Dream up a lead magnet

CHAPTER 3: DISTRIBUTION (NON-SEO)

Remember the distribution vectors that you identified in Exercise #6? Take these, or the channels that you’re
currently prioritizing for your publication, and consider how they rank across the CODES framework. Do you
have a balanced portfolio of channels? Do you have any significant bedrock? Do you trust these to be
consistent?

Lead magnet ideas:

1.

2.

3.

4.

5.

PRO-TIP: If you’re looking to convert your web-based articles into a PDF and you don’t
want to spend hours formatting them, you can print directly from the
browser, using reader mode.

• In Safari, use the shortcut Cmd + Shift + R or click the “reader” icon.
• In Chrome, go to “chrome://flags/#enable-reader-mode” and enable reader mode.

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EXERCISE 14
Competitor research

CHAPTER 3: DISTRIBUTION (NON-SEO)

Identify your top 3 competitors. Investigate each of them on Moat, Ghostery, and SimilarWeb. Jot down
anything that you learn or ideas that are sparked.

LEARNINGS FROM LEARNINGS FROM LEARNINGS FROM

COMPETITORS
SIMILARWEB GHOSTERY MOAT/FB AD

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EXERCISE 15
SMART goals

CHAPTER 3: DISTRIBUTION (NON-SEO)

Identify your next (1-3) SMART goals. If you don’t have a timeline in mind, try setting goals for the next 30 days.

If you have historical data already, use this to influence your goals and create a bull (best) case, bear (worse)
case, and base case (if you changed nothing). Set your goals somewhere in between the base and the bull.
Then, clearly define what success would look like. Go through each goal and make sure that it is SMART
(specific, measurable, attainable, relevant, time-bound)

GOAL BEAR CASE BASE CASE BULL CASE SMART GOAL

Write more articles No articles 4 articles (aver- 8 articles 5-6 articles pub-
age last month) lished over the
next month

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EXERCISE 16
Mapping out queries to problems

CHAPTER 4: SEARCH ENGINE OPTIMIZATION

If you use Chrome, enter “chrome://history/?q=google%20search” into your browser. This should give you a
list of your recent Google searches. If you use another browser, navigate to your search history.
Go through your last 6 searches and map out what the core problem was that you were trying to solve.

RAW QUERY CORE PROBLEM

“black screen mac” “How do I fix my mac?”

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EXERCISE 17
Ranking factors explained

CHAPTER 4: SEARCH ENGINE OPTIMIZATION

Here is a list of ranking factors from SparkToro.

Go through the list and consider what each of these ranking factors is actually signalling to Google. Are they
communicating that the page is usable? Are they communicating that the content is relevant? Are they
communicating that the website and/or content is credible?

RANKING FACTOR SIGNAL TO GOOGLE RANKING FACTOR SIGNAL TO GOOGLE

Relevance of overall page Freshness of publication

content

Quality of linking sites and Anchor text of links pointing

pages to the page

Use of query-relevant Location, frequency, and

words and phrases distance of related words

Domain’s perceived exper- Total amount of on-page

tise, authority, and trust content

Mobile friendliness Use of unique, relevant

images

Exact match keyword use Site accessibility factors

Quantity and diversity of Anchor text of links to other

linking websites pages on the domain

Content’s accuracy with Keyword use in the URL

accepted facts

Link authority of host do- “Unlinked mentions” of the

main site/brand

Page’s perceived expertise, Age of the website

authority and trust

Use of query-relevant enti- Use of Google AMP

ties in page content

Load speed Use of external links on the

page

Usage data, e.g. po- Keyword in the domain

go-sticking, engagement name

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EXERCISE 18
Search intent

CHAPTER 4: SEARCH ENGINE OPTIMIZATION

Take your search history keywords from Exercise #17 and map out the intent. You can also have fun with
the keywords below. After you guess, go to Google and see what is ranking there, to validate or invalidate
your answer.

RAW QUERY INTENT

“black screen mac” informational

“peanut”

“terracotta warriors”

“moleskine notebook”

“zoom keeps freezing”

“transferwise legit”

“art sqool”

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EXERCISE 19
Content competitors

CHAPTER 4: SEARCH ENGINE OPTIMIZATION

Identify 3 “content competitors” and go through the keywords they’re ranking on. Pull out article topics that
are both, 1) interesting to you and 2) aren’t very competitive from an SEO perspective.

DOMAIN KEYWORD IDEA COMPETITION SEARCH VOLUME NOTES

brainpickings.org “a velocity of 3 (low) 800 Would need to

being” create a book
summary

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EXERCISE 20
Build 30 links

CHAPTER 4: SEARCH ENGINE OPTIMIZATION

Go through the list of 17 link-building suggestions and circle which approaches you’d like to try for your
next 30 links. For each tactic that you circle, write down the next step for you to take.

1. Use other assets you own

2. Pay for links
3. Build your own link-building team
4. Buy a domain
5. Guest post
6. Doing interviews
7. Interview others
8. Partnerships/exchanges
9. Give reviews
10. Claim unlinked mentions
11. Help a reporter out (HARO)
12. Become a “reporter”
13. Create a linkable “product”
14. Solve a common problem
15. Submits to communities, directories, listicles
16. Get one big “win”
17. Do competitor research

Next steps:

1.

2.

3.

4.

5.

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EXERCISE 21
Identify associated problems

CHAPTER 4: SEARCH ENGINE OPTIMIZATION

In earlier sections of this book, I encouraged you to clearly identify your audience. Now, write down 3-5
associated problems (like finding routing numbers, jobs, book summaries, etc.) that your target audience
may be looking for online. Consider whether you could create a solution for each of these.

Ideas:

1.

2.

3.

4.

5.

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EXERCISE 22
Monetization

CHAPTER 5: MONETIZATION

Using the monetization matrix, identify whether you’d like to monetize with content, donations, affiliates, web
ads, newsletter sponsorships, products/services, or some combination of the above.

Based on the learnings in this chapter, take a few notes on why you’re making this decision and the next
steps you should take.

CHANNEL IF YES, WHY? NEXT STEPS?

CONTENT

DONATIONS

AFFILIATES

WEB ADS

NEWSLETTER SPONSORSHIPS

PRODUCTS/SERVICES

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