College teacher turned ghostwriter | Scaling founders, coaches, and consultants to $100K+ /mo | Writing to build wealth and better self | 98,000 on Twitter (X)

Taylin John Simmonds

I just want you to know, it’s possible to become a full time writer. 

It might take longer than expected. It might not happen the way you expected. But it is possible. 

Please, on the hard days, remember that.

College teacher turned Substack ghostwriter | Helping multi-passionate writers and creatives earn on the internet | 2 billion impressions | $4,000,000+ revenue generated | All in on Substack

I ghostwrote for 6 months with zero pay.

3am writing sessions to hit deadlines. Then I’d teach college classes from 8am to 6pm (exhausting).

I tracked every win. Saved the screenshots. Studied what worked.

That invisible work became my portfolio.
That portfolio landed my first paid client at $3,000 a month.

To get paid, get proof.

I’m 31, Canadian, introverted, and run a small online writing biz with my high school best friend.

Last year, we did $315,000 in revenue.

What we sell (copy us if you like):

– Social media ghostwriting: $4,700/mo + 10% commission
– Newsletter ghostwriting: $2,000 /mo
– Ghostwriting coaching: $5,700/qtr
- Ghostwriting course: $500
- Paid Substack newsletter: $99/yr

How we market:

– Post on LinkedIn 5x/week
– Post on Substack 7x/week
– Post on Twitter 14x/week
– Email my list 2-3x/week
– DM 100 people/mo on LinkedIn

Tools we use:

– Loom (SOPs and audits)
– Stripe + Whop (payment processors)
– Calendly (calendar bookings and pre-sale automation sequences)
– Heartbeat (community platform for coaching)
– Eden (all writing + my entire life in systems)
– Notion (company systems)
– Claude + ChatGPT (AI assistance)

Where I started:

4 years ago I was a college teacher who knew nothing about business, marketing, or sales. I just wanted more control over my time and to make a little more money. Today, I have exactly that.

if you do a fraction of this, you can make $100K /yr on Substack alone. You just need the right offers, strategy, and time.

I hope this gives you some direction.

—Taylin

My tiny writing biz did $315,000 last year.

If I were starting over and wanted 6 figures, I’d ghostwrite newsletters on Substack.

Go to LinkedIn, find business owners, health coaches, and tech founders. DM them. Show them how a paid newsletter will make them more per mo than they pay you.

Do this well and you’ll have more clients than you can handle.

Funny... After 31 years of exploring, my happy life turned out to the simple one.

• Reading great books
• Going on walks to think
• Writing what I’d love to read

A little breathwork. A lot of time with my gf.

That’s it. That’s happiness.

Build in public (show your process)
Think in public (share your insights)
Write in public (show your skill)

Public credibility creates private opportunities.

If you want to level up in life, you must create more than you consume.

Create art, books, content, products, and businesses. Shape your body, mind, and environment. Build your ideal life one tiny step at a time.

Most people are stuck because they only watch. Don’t be like them.

Create something. Anything.

You only need 1 client.

Not one who underpays, drains your energy, and ignores boundaries.

1 client who pays more than most corporate salaries, treats you like a professional, and builds with you long term.

That single client will permanently change what you think is possible with a one person business.

You're exhausted because you have too many open loops.

Too many books you’re reading. Articles you’re writing. Skills you’re learning. Businesses you’re building. Problems you’re solving.

Pick one thing (for now). And grieve the rest. 
Energy will follow.

Don’t write with AI. Write assisted by AI.

AI can come up with ideas. You decide which are worth writing.
AI can research. You fact-check.
AI can give feedback. You choose what to keep.

You think. You write. You lead.

You bring the perspective, taste, and truth that no machine can.

AI saves you time.

Not so you can write less, but so you can write more, write better, and write more you.

Solo building is overrated.

Find your people. Meet daily. Build cool sh*t together.

I’m creating a newsletter ghostwriting course with two close friends and it’s the most fun I’ve had in months.

Few things beat building with people who care as much as you do.

The happiest people I know are not doing more. 
They are noticing more.

They pause to celebrate small wins others ignore. Ten minutes of focused work. One uncomfortable email sent. An honest start on a low-energy day.

That habit will make you effective.

Because people who notice progress keep going.

Multi-passionate people get stuck because they over-consume and under-create.

You don’t have to give up learning. But you do need to devote yourself to producing work daily.

Create for 2-4 hours in the morning. Explore for 1-2 hours in the evenings.

That’s how you both learn and earn with multiple interests.

You don't need motivation to achieve great things.

I don't always feel like writing.
I don't always feel like working.
I don't always feel like exercising.

Honestly, MOST days I don't feel like it.

But I do it anyways.
And I never regret it.

The future won’t belong to specialists who refuse to change.

It will belong to people who can become someone new again and again.

Technology is moving too fast for fixed identities.

Agency, learning speed, and keeping cool under uncertainty are the new job security.

A lack of pressure leads to an abundance of procrastination.

New milestone: 100 paid subscribers on Substack!

Chase Dimond

Top Ecommerce Email Marketer & Agency Owner | We’ve sent over 1 billion emails for our clients resulting in $200+ million in email attributable revenue.

I help brands make more money with email marketing.

I’m a Co-Founder of Structured, an ecommerce email marketing agency. Since launching in 2018, our team has helped brands send billions of emails and generate over $200M in email-attributable revenue.

We’re a top agency partner for platforms like Omnisend and Klaviyo.

Shopify featured me as a top email marketing influencer. I’ve also received LinkedIn’s Top Voice Award for Email Marketing, and Favikon has ranked me as the top email marketer across social media.

Some of the brands we’ve worked with include:

Poo~Pourri
Eight Sleep
Health-Ade
Mixtiles
Vessi

If you’re looking to hire an experienced email marketing agency, you can reach me here:

chase@chasedimond.com

——

Outside my agency, I run a number of other fast-growing businesses. I’m fortunate to have over 750,000+ followers and subscribers across my social channels and email newsletter.

I’ve worked with companies including:

LinkedIn
Amazon
TikTok
Gamma
Alibaba
Zapier
ClickUp

I work with a small number of paid sponsors and partners each year.

If you’re interested in exploring a potential fit, please email me with details:

chase@chasedimond.com

Founder

My newsletter is your no BS guide into what's working in email marketing - I'll give you the latest tips + tactics to help you drive more revenue from your email marketing channel. 

Sign up (it's free) here: https://chasedimond.com/chase-email-newsletter

If your job costs you your peace,
it’s too expensive.

You deserve a job that lets you sleep peacefully at night -
not one that keeps you awake questioning your worth, your future, or your sanity.

A healthy career doesn’t rely on:

 ❌ burnout
 ❌ constant anxiety
 ❌ toxic expectations

A healthy career is built on:

 ✔️ clear boundaries
 ✔️ supportive leadership
 ✔️ meaningful work
 ✔️ respect for your time and well-being

Your job should challenge you - not drain you.

It should grow you - not break you.

And it should fit into your life, not become your life.

If your work steals your peace, it’s costing you more than it pays.

Top Ecommerce Email Marketer | $200M+ Generated via Email

Working with smart people is great.
But it is not enough.

Because intelligence can solve problems.
But humility and kindness build cultures where problems don’t have to exist in the first place.

Here’s why it matters so much 👇

Kind and humble people:

They make collaboration effortless.
You don’t waste energy defending ideas or egos. 
You build together - faster, cleaner, and with more trust.

They create psychological safety.
When people feel respected, they speak up, share bold ideas, 
and admit mistakes early. 
That’s how teams innovate and grow.

They inspire long-term loyalty.
People don’t leave companies - they leave toxic dynamics. 
Working with grounded, genuine teammates keeps great talent around.

 Ways to practice kindness and humility at work:

Listen more than you talk.
You don’t need to have the loudest voice to have the strongest impact. 
Listening builds connection and earns respect.

Give credit - generously.
Acknowledging others’ work doesn’t diminish your own. 
It multiplies the trust and energy in your team.

Keep learning.
The moment you think you’ve “arrived,” you stop growing. 
Stay curious, stay open, and never let success make you unapproachable.

Kind people build strong teams.
Strong teams create big results.

Funny how your brain has unlimited energy
for worst-case scenarios.

It can write entire disaster scripts at 3 a.m.
With dialogue.
With consequences.
With a soundtrack.

But ask it to imagine things going well
and suddenly it needs evidence, references, and a peer review.

That’s not intuition.
That’s anxiety pretending to be preparation.

You don’t need to stop overthinking.
You just need to stop letting it bully you into pessimism only.

If your mind insists on spiraling,
at least make it spiral in both directions.

Same brain.
Different hypothesis.

Image credit: bywiseword

Reality:
A small, ordinary action.

LinkedIn:
A “high-impact initiative” with “key learnings” and “next steps.”

Clear communication beats inflated language.
Strong professionals don’t need to oversell normal work.

Say what you did.
Say why it mattered.
Move on.

Clarity builds trust faster than buzzwords.

Image credit: TheSecretAcct on Twitter/X

It’s not about collecting business cards or follower counts.

It’s about building bridges with people who get it - who challenge you, inspire you, and open doors you didn’t know existed.

The right network doesn’t just grow your career - it expands your mindset, your confidence, and your opportunities.

Here are 12 ways to build powerful, authentic connections:

1️⃣ Lead with curiosity. Ask, don’t pitch. People love being seen and heard.

2️⃣ Add value first. Share insights, introductions, or encouragement before asking for anything.

3️⃣ Show up consistently. Comment, engage, and participate where your industry hangs out.

4️⃣ Find your communities. Join professional groups, Slack channels, or niche forums.

5️⃣ Attend events strategically. Go where your next mentor, collaborator, or client might actually be.

6️⃣ Follow up. A short, thoughtful message can turn a conversation into a relationship.

7️⃣ Be generous with your expertise. Give more than you take - it builds reputation fast.

8️⃣ Don’t chase status. The best opportunities often come from peers, not big titles.

9️⃣ Stay authentic. Pretending to be someone you’re not is the fastest way to disconnect.

1️⃣0️⃣ Keep it human. Share stories, not sales pitches.

1️⃣1️⃣ Support others publicly. Celebrate others’ wins - it builds goodwill that lasts.

1️⃣2️⃣ Play the long game. Relationships compound like interest; nurture them with time.

The truth? You’re one conversation away from a completely different path.

Image credit: Tim Stoddart

The advice I wish I could’ve given myself 8 years ago:

Create a culture people never want to leave.

Yes, you can’t keep everyone with a 0% turnover rate. 
Let’s face it.

But what you can do is build an environment people don’t want to walk away from.

Build a culture that makes employees:

↳ Recommend it to their friends as the dream job, 
↳ Stay, even if the paycheck isn't perfect yet, 
↳ Come back when the conditions are right.

Think about it:

👉 A competitive paycheck might keep someone for a while, 
But a toxic culture will drive them away for good.

👉 You can offer all the perks, but if the culture is unhealthy, 
Nothing will make your best people stick around.

People stay where they feel valued.

It’s not just about the money—it’s about creating a workplace 
that makes people excited to show up every day.

♻️ Share this post with your network if you agree. 

 Credit: Victoria Repa ( go follow her )

Small habit.
Big impact.

The way you speak to yourself
every morning
becomes your baseline.

Speak growth.
Speak calm.
Speak possibility.

It adds up.

Image credit: Wordofwise_ on Twitter/X

“Hire the people that…”

Interesting how the list skips:
– constant availability
– performative hustle
– being the loudest voice
– working 24/7 for optics

Great teams grow from maturity, not heroics.
From people who communicate clearly, take ownership, and move in sync.

Ego slows teams down.
Trust speeds them up.
Psychological safety keeps the work moving.

Hire for reliability and collaboration first.
Everything else gets easier after that.

Nobody talks about this part enough.

You can do it tired.
You can do it frustrated.
You can do it unsure.

You just can’t do it if you quit.

Keep going.


Image credit: Dearme2_ on Twitter/X

Here’s a hard truth most people avoid:

If you’re not making mistakes, you’re not moving forward.

I learned this the slow way.

Early on, I tried to get everything right.
Perfect plan.
Perfect timing.
Perfect execution.

And progress?
Basically stalled.

Things only changed when I gave myself permission to be wrong.

To test ideas that might flop.
To ship work that wasn’t perfect.
To learn out loud instead of waiting in silence.

Mistakes aren’t failure.
They’re feedback.

The people doing the most interesting work
aren’t avoiding mistakes.

They’re just willing to make them faster.

Safe paths feel good.
But they don’t teach much.

Growth always comes with friction.
That’s the price of trying something new.

Image credit: Tomas Gorny

Marketing is great they said…


P.S. If you write emails and you’re looking for inspiration, check out:

inboox.ai

“It wasn’t a waste of time if you learned something.”

That’s easy to agree with in theory.
Harder when the lesson came with lost money, bruised confidence, or a year you won’t get back.

Still - experience has a way of paying later.

It sharpens your instincts.
It changes what you tolerate.
It shortens the gap between seeing a red flag and acting on it.

Not every chapter produces visible wins.
Some exist to quietly upgrade your judgment.

And that upgrade shows up in every decision after.

10 years of rejection.

That's how long Squid Game's creator spent pitching his script.

Studio after studio said no.
Too dark. Too violent. Won't work.

Then Netflix took a chance.

28 days later, it became their most-watched show in history.

A decade of "no" turned into a $900M yes.

Most people quit after a few rejections.
They assume the silence means the idea is bad.

But rejection isn't a verdict.
It's just timing.

The right opportunity doesn't always show up first.
Sometimes it shows up tenth. Or hundredth.

If you're getting rejected right now, consider this:

You might not be wrong.
You might just be early.

Keep going.


Image Credit: Amy Sussman/WireImage; Noh Juhan/Netflix

How to survive marketing in 2026.

Open your laptop.
Check Slack.
Three notifications in…

…and you already feel behind.

Sound familiar?

In 2026, “digital marketer” doesn’t mean one role anymore.
It means the entire agency in one tab.

Copywriter.
Strategist.
Videographer.
Social media manager.
Designer.
Editor.
Analyst.

All before lunch.

From experience, the problem isn’t a lack of skill.
It’s the expectation that one person can do everything at once and do it well.

Burnout doesn’t come from hard work.
It comes from an impossible scope.

The marketers who survive aren’t the busiest.
They’re the ones who set boundaries, prioritize ruthlessly, and stop trying to be great at everything every day.

Because marketing isn’t about doing more.
It’s about doing the right things consistently.

Agree?

Our email domains kept getting blacklisted at my agency.

Everyone assumed we were sending too aggressively.

After diving into the data, we found the real issue.

18% bounce rate.
From a "verified" list.

We had bad data.

𝗧𝗵𝗲 𝗵𝗶𝗱𝗱𝗲𝗻 𝗰𝗼𝘀𝘁𝘀 𝗻𝗼𝗯𝗼𝗱𝘆 𝘁𝗮𝗹𝗸𝘀 𝗮𝗯𝗼𝘂𝘁:

Deals lost during 2-3 weeks of rebuilding.
Hours spent verifying and cleaning lists.
Teams questioning their skills when it's not their fault.
Buying new domains every month.

We thought this was just how outbound worked.

Then I saw a friend's company sending thousands of emails each week.
Same domains. Month after month.
Strong deliverability maintained.

They were using Prospeo.io's data.

SMTP handshakes verify emails before you send.
BounceBan removes risky addresses automatically.
Weekly updates catch job changes that kill domains.

After testing several providers, Prospeo consistently delivered the cleanest data.

Our domains have been going steady for months now.
Data prep time cut by 80%.
Bounce rates dropped from 18% to under 2%.

Clean data isn't just about deliverability.
It's about keeping your team confident and productive.

What hidden costs is bad data creating at your agency?

Brand partnership • Top Ecommerce Email Marketer | $200M+ Generated via Email

6 Copywriting Techniques You Can Leverage for Your Sales Pages:

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January hits different for ecommerce founders.

Sales slow down. Costs don't.

You're staring at:
- Depleted inventory
- Q1 expenses stacking up
- Ad costs that won't wait
- Cash tied up in last quarter's orders

The revenue will come. But the bills are here now.

This is the ecommerce cash flow trap.

Most founders either:
→ Wait it out and lose momentum
→ Take on debt with rigid terms
→ Give up equity way too early

That's where Wayflyer comes in.

Capital in 24-48 hours. Non-dilutive. Flexible repayment based on your actual sales.

No giving up ownership. No waiting weeks for bank approvals.

You restock. You scale Q1 ads. You keep the momentum going.

$6B+ already deployed to brands like yours.

If your cash flow is playing catch-up, get your offer today: 

https://lnkd.in/gJsgPrrm


#WayflyerSponsor

I used to think GTM complexity was just part of the job.

Multiple tools. Manual handoffs. Workflows that took hours to build and days to fix.

Last week I tested Apollo's AI Assistant on something different: workflow creation.

Instead of clicking through menus and configuring triggers manually, I just described what I wanted in plain English.

The AI built the multi-step workflow in minutes.

What used to require:
→ A GTM engineer
→ Multiple tools stitched together
→ Hours of setup and testing

Now happens in a single conversation.

Same thing with building prospect lists, creating sequences, or analyzing campaign performance. Describe what you need. The AI handles the execution.

Most teams are still doing GTM the old way. Clicking through settings, connecting triggers, testing each step manually.

Meanwhile, the fastest operators are just talking to the AI.

GTM shouldn't require an engineering degree.
It should require clear thinking and the right tools.

Join the beta waitlist:

https://lnkd.in/gW2ZeEUb

#ApolloAIAssistant #ApolloPartner

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The Battle

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