Episode 8
· 21:20
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You know, it's a funny thing.
You pour your heart into something
online, your passion project, right?
Mm-hmm.
And theN sometimes the very act of sharing
that passion just turns into this, uh,
mountain of behind the scenes work.
Yeah.
That pull between the creating you love
and all the, the operational stuff.
It's real.
It really is.
We've all felt that tug of war.
Well, today we're looking at a story
that I think will really hit home,
especially if you're building your world
through something like a newsletter.
Definitely.
There's often this point where the
sheer weight of operations just
starts to pull you away from why you
started creating in the first place.
You know that joy of connecting
and sharing insights.
Exactly.
So let's talk about Cora Now,
Cora isn't one specific person.
Okay.
But her journey, it's like a
mashup of so many real experiences.
We've seen a
familiar pattern,
right?
She built this fantastic newsletter.
It was all about alternative
wealth building strategies,
and it really took off.
I mean, really?
Okay, we're talking
like 48,200 subscribers,
but a significant,
yeah, and great engagement too.
Like a 4% click through rate,
and she was pulling in a solid
$56,000 in annual revenue.
By all measures, you know, a real success.
That's a remarkable achievement,
really shows what happens when valuable
content clicks with the right audience.
But here's where things started to get.
Well, a bit complicated for her.
Mm.
Cora found herself with less and less
time to actually do the things she
loved exploring those wealth strategies.
Oh, okay.
More time on the other stuff.
Exactly.
More time grappling
with the technical side.
Hmm.
She actually described feeling
like an unpaid email technician,
and yet that she was having
three, uh, 3:00 AM panic attacks
oof.
Three in the morning.
Yep.
Over things like broken email templates.
Yeah.
Can anyone out there relate
to that level of like.
Tech induced stress,
I bet they can.
That kind of anxiety, it's just not
sustainable and it really signals a
crucial turning point, doesn't it?
For so many creators.
Totally.
That initial buzz of building an audience,
it can get swamped pretty quickly by
just the sheer volume of tasks needed to
keep things running, let alone growing.
Right?
So a key insight here, maybe
for anyone growing a newsletter.
Is realizing your initial passion,
your skills, they might not be enough.
As you scale up, you're gonna hit
these operational hurdles that need,
well, a different kind of expertise.
Something focused on helping
you make actual progress.
Absolutely.
And that's the core of
the issue, isn't it?
Success for Cora, it brought
more operational headaches than
actual, you know, forward movement
towards her creative goals.
Yeah.
It wasn't a lack of passion or good ideas.
No, not at all.
It was the sheer burden of
managing everything behind the
curtain that was stopping her from
making the progress she wanted.
We often see creators hit this kind
of wall, maybe around the 10,000
subscriber mark, give or take.
Yeah.
What starts as a personal project, it
sort of morphs into something more like
a small media business and the demands
on the infrastructure, they just shift.
Dramatically.
Right.
It's not like the tools, the email
platforms suddenly disappear.
No.
The tools are still there,
but the complexity of using the
retention deliverability, segmenting your
audience, all those moving parts, yeah.
Become so much more demanding.
Exactly.
The complexity just explodes.
And Cora felt this firsthand.
Yeah.
Her content.
Focused on investments.
Totally legit educational stuff.
Yeah,
it kept getting flagged by her
email service provider, her ESP. Ah,
the dreaded high risk flag.
You got it flagged as high risk.
Imagine the frustration, just
constantly battling those kinds
of tech hurdles when you're trying
to share valuable information.
That's a perfect example of what we could
call the paradox of newsletter success.
Okay.
Tell me more.
Well, Cora's audience grew because
her content was insightful.
Right.
It was valuable.
Mm-hmm.
But as that audience got bigger, she
had less and less time to actually
produce that valuable content.
Oh, wow.
Yeah.
The hour she used to spend
researching writing, now they were
eaten up, checking spam scores,
digging through deliverability
reports, trying to make sure her
emails actually landed in inboxes.
Right.
Just keeping the lights on basically.
Pretty much, and it's this really
counterintuitive situation that
catches a lot of successful creators.
The very growth you work so hard for,
it can end up limiting you if you don't
manage the operational side strategically.
If you can't keep making
progress on the content itself.
It's almost like she was being
penalized for doing well.
The very thing driving her
growth was getting choked by the
operational weight of managing it.
That's a great way to put it.
The skills that got her started
connecting with readers, building
that list, they suddenly became less
important than the technical skills
needed just to keep the machine running.
Her expertise in alternative
investments ends up taking a back
seat to figuring out email headers.
Exactly.
It's a real shift.
So she's in this spot.
Her passion is getting buried under
this mountain of tasks, stopping the
very progress she set out to make.
And this isn't just Cora's story, is it?
This is common.
Oh.
Incredibly Common creators pour their
souls into their work and then bam,
they find themselves spending most of
their time on things that feel miles
away from the actual creation they love.
And for Cora, that imbalance
became really stark.
She actually sat down and looked
at where her time was going.
And discovered that an astonishing
88%, 88% of her week was
going to operational tasks.
Wow.
Things like managing the platform, dealing
with sponsors, looking at metrics list
management, designing emails, formatting.
All of it,
leaving just 12% for the
actual content creation.
Whoa.
The core of her business,
just 12%.
That is staggering.
It really shows how easily the joy,
the creativity, the progress you want
can get lost in that daily grind.
Mm-hmm.
It's not like these operational
tasks are totally separate
from the content, are they?
They're all linked,
completely intertwined.
If your emails don't get delivered,
who sees your brilliant insights?
Yeah.
Nobody, right?
If you can't manage sponsor relationships
properly, your revenue takes a
hit, which then limits your ability
to invest back into creating more
great content, hitting those goals.
It hinders that progress.
Yeah.
It's all one system.
Indeed, it's a unified system and when
one part starts buckling under the
weight, it pulls everything else down
with it stalling that forward momentum.
Cora, like a lot of folks
initially thought, I can handle
this, I should handle this.
The DIY approach
exactly that it was the
responsible thing to do.
But as the newsletter grew, she realized.
Doing it all just meant she was juggling
like five different demanding jobs badly.
So what did she try next?
Because clearly those 3:03 AM wake
up calls weren't helping her make any
real progress that wasn't sustainable.
No, definitely not.
So her first move, and this is super
common for creators hitting the stage,
was to bring in some outside help.
She hired freelancers.
Yeah.
Got a virtual assistant, a tech
specialist, and a designer.
The thinking was, you
know, divide and conquer.
Lighten the load.
Free up time for content,
make some headway
and on paper that makes total sense.
Delegate the stuff you're not
great at or the just eat your time
seems logical.
Right.
And for a little while, maybe it looked
like it was working, but the reality
managing those freelancers just became
another huge time suck for Cora.
Oh really?
How so?
Well, the VA didn't quite get
the specific metrics that matter
for a newsletter business.
You know, it's different from
e-commerce, the tech specialist.
Sometimes just vanished for days.
Unresponsive.
Mm-hmm.
And the designer made beautiful templates.
Sure.
But they often broke or looked
weird in different email clients,
big deliverability, headache.
Well, so she ended up managing
the managers basically,
pretty much.
She wasn't just doing her core
work, she was now managing this.
Team of people who didn't fully grasp the
specific needs of her newsletter business.
It wasn't helping her progress, it was
adding another layer of complexity.
Ouch.
Okay, so that didn't quite work.
What was attempt number two to solve this
operational knot and get back on track?
Next up, she explored hiring a
general digital marketing agency.
Ah, the agency route.
Yep.
They promised the world, you know,
handle all the email marketing.
Showed her some impressive case studies.
Mostly from e-commerce brands though.
Okay.
Bit of a flag there maybe,
perhaps.
But it was a big investment for her
financially and she was hopeful.
Hopeful this would finally let her
refocus on content and actually drive
the progress she was aiming for.
And I have a feeling, given the pattern
here, that this also didn't quite
hit the mark for her specific needs.
Not really, no.
Not only the way she needed the agency.
They were great at promotional
emails, sales funnels.
You know the standard
e-commerce playbook, right?
But they lack that deep, specialized
understanding of newsletter
publishing as its own business model.
They struggled with her
specific deliverability issues,
the content filtering stuff.
They didn't really have
processes for managing sponsor
relationships effectively,
which are crucial for newsletters.
Absolutely critical.
Yeah.
And their advice for
boosting engagement felt.
Well generic like, oh, just
add more calls to action.
Helpful.
Eventually the account manager
basically admitted they didn't
work with many newsletters.
Their systems were built
for selling products online.
So it sounds like a classic case
of trying to fit a square, peg her
newsletter business into a round hole.
Their e-commerce focus system,
that's a perfect analogy.
The dynamics are just different.
Nurturing a community, managing
sponsors, it's not the same as
driving direct sales for a product.
Okay, so freelancers didn't cut it.
The general agency wasn't
specialized enough.
Did she try anything else?
She did.
She got more specific.
She hired a specialized
email marketing agency.
Next one that specifically said
they worked with content creators.
Ah, getting warmer perhaps.
It seemed promising initially.
They helped with the
technical email stuff.
Migrated her to a new ESP, improved her
analytics setup for a couple of months.
Things felt like they were
moving in the right direction.
Again, maybe some real
progress was possible.
Finally.
A glimmer of hope she could maybe
get back to actually writing.
There was definitely a glimmer.
Her deliverability did get better.
She did claw back some time for
content, but then she wanted
to launch her premium tier.
Okay.
A new strategic initiative.
Exactly.
And that's where she hit another wall.
This specialized email marketing agency.
Great.
On the email tech side, but they didn't
have the expertise in the broader
business aspects of a subscription model.
Like payments and paywalls,
precisely seamless payment processing,
integrating content paywalls effectively.
They basically said, uh, you'll
need someone else for that.
Another specialist.
Oh, for crying out loud.
Right.
And again, no real systems
for managing her sponsors.
She was still juggling all
of that herself manually.
Their focus stayed just on the email
itself, not the whole newsletter business
ecosystem she was trying to build.
And importantly, progress.
It's like she kept finding
individual puzzle pieces.
Someone for tech.
Maybe someone else for payments,
but couldn't find anyone to help her
see and assemble the whole picture,
the interconnectedness of it all.
That's exactly it.
She needed someone who understood how
deliverability affects sponsor value,
how content drives premium subscriptions,
how all these pieces work together to
help her make the progress she wanted.
So after all these frustrating
attempts, what was the big realization?
She finally realized she didn't
just need an email marketing
company, even a specialized one.
She needed a full service
newsletter operations partner.
Okay.
What's the distinction there?
It's about depth and breadth.
Someone with deep, specialized
knowledge of the unique challenges
and opportunities of running a
content driven subscription business.
Someone focused on helping
creators achieve their desired
outcomes, their desired progress,
not just ticking off email tasks.
So what was the actual turning point?
How did she shift from feeling like
that Overwhelmed email tech back to
being a creator, making real progress.
The real light bulb moment came
when she took a step back and
did a really thorough audit.
Forensic level.
Yeah.
Every single task involved
in running her newsletter.
Okay.
Focused on where her time was
actually going and what was really
stopping her from focusing on content.
She tracked time per task,
frequency, the whole nine yards,
getting granular,
very, and this exercise just laid it bare.
That huge chunk of time.
The 88% we mentioned was on
everything except creating the
valuable content her audience loved.
And that drove the business forward.
And crucially, she saw how
interconnected it all was.
Plateauing engagement that hurt her
sponsor value, which hit her revenue.
Which limited her ability to
invest in fixing things or growing.
It was a cycle, preventing progress,
seeing the numbers like that,
the actual time breakdown.
Yeah, that must have been a massive
wake up call really highlighting
the barriers to her making progress.
It absolutely was.
And based on that detailed audit, Cora
developed a really clear set of criteria.
What would a real solution need to provide
to help her actually achieve her goals?
Moving beyond.
Just fix my email problems.
Way beyond.
It wasn't just about
sending emails anymore.
It was about comprehensive
operational support, deep
newsletter specific expertise.
Help with growing both
audience and revenue.
Yeah, technical reliability she
could actually count on, and
maybe most importantly, giving her
back that precious time to create
and move her business forward.
Make progress.
So her whole perspective shifted.
It wasn't about finding someone to
just handle emails, it was about
finding a partner who got the
entire business of a newsletter.
Exactly.
Someone who could help her make
significant strides across the board.
And how did that change her search?
She recognized that general marketing
knowledge just wasn't enough.
She needed someone who understood
the specific quirks of ESPs with
content filtering for subscriptions.
Right, like her high risk issue
precisely.
Someone who knew the KPIs that actually
matter for a newsletter business,
which are different from e-commerce.
And crucially, someone who knew how to
effectively manage sponsor relationships.
In that unique newsletter context, her
mindset shifted from I need someone
to do tasks, to, I need a strategic
partner with proof they've solved these
exact problems for other newsletters
and help them achieve real progress.
And with that clarity.
I bet her search for the right
partner looked totally different,
completely different.
No more just looking at the cheapest
option or the biggest agency name.
She focused on finding a specialized
partner who genuinely understood
her specific needs and the kind
of progress she was aiming for.
Yikes.
She actually created a detailed
requirements document, laid out her.
Non-negotiable.
Oh, things like full stack services
covering all the operational bases.
Mm-hmm.
Demonstrable experience
with content first.
Newsletters like hers, established
systems for sponsor management,
deep deliverability expertise.
Got it.
The must haves.
Right.
Then she listed her high
priority wants and nice to haves.
That document became her filter,
her framework for evaluating
potential partners and making
sure they were aligned with.
Her goals for progress.
That's really smart.
It forces you to define what success
and progress actually look like for you
instead of just reacting to sales pitches.
Exactly.
And doing that research, she mapped out
the different players, general email
companies, broad digital agencies,
freelancer platforms, and finally these
newsletter operations specialists.
Damn.
While they all had pros and cons, it
became crystal clear that the newsletter
operations specialists were the only
ones who truly fit her comprehensive
needs and her drive for significant
progress across the whole business.
Okay, so she finds this
specialized partner.
I. What actually happened then?
What did that transformation
look like day to day?
Yeah, and for the newsletter's progress,
the impact, it was almost
immediate and pretty profound.
Those Monday mornings freaking
out about tech issues gone nice.
Her time spent on operations, it
dropped from that crushing 88% down to
a much more manageable 30% of her week.
Huge difference.
Massive.
She could finally actually
focus on her content calendar.
Those cool content series that were
just sitting in her drafts forever.
They finally got published, delivering
more value, engaging her audience,
getting back to the core mission,
totally sponsor payments,
suddenly reliable, consistent.
They put in streamlined automated systems.
She even wrote this deep dive piece.
Remember her niche was alternative wealth.
On small business acquisition strategies.
Yeah.
It resonated so much.
It became her most shared piece of
content ever drove a ton of growth.
She basically rediscovered the joy
of creating, you know, and that
satisfaction of making real progress.
Again on her vision.
That sounds like just an incredible
weightlift, that shifting
from constant firefighting to
actually building something.
Yeah.
Focusing on what she loves and
the progress she envisioned.
Absolutely.
And the right partner
didn't just fix problems.
They helped her build robust, sustainable
systems across the whole operation.
Okay, like what kind of systems?
Well, things like data-driven,
strategic planning, effective
audience growth strategies.
They launched a referral program
with a 22% conversion rate,
ran targeted campaigns with a
41% lower cost per subscriber.
Wow.
Real numbers.
Yeah.
Content optimization systems to
boosting engagement, repurposing her
best stuff, technical reliability,
stuff that drastically improved
deliverability revenue optimization,
like developing a proper value-based
sponsorship rate card and that successful
premium tier laundry mentioned.
And finally, a solid analytics and
optimization loop for just continuous
improvement, continuous progress.
So it wasn't just patching halls,
it was building a solid foundation
for sustained growth, always moving
towards those desired outcome.
Exactly.
And the return on that
investment, pretty substantial.
Her sponsor revenue jumped 22%.
That premium tier added
an extra $2,300 a month.
And her effective reach, the
number of people actually seeing
her emails grew by 14% because
deliverability was so much better.
And what was the cost for
this specialized help?
It was $999 a month, which when
you weigh it against the revenue,
increases the time, saved the growth.
It was a very clear win.
And like Cora said, the peace of
mind, priceless, no more, 3:03 AM
panic attacks about email templates.
That really drives home
the point, doesn't it?
Sometimes investing in the
right specialized expertise
isn't just an expense.
It's a strategic move that frees
you up to generate way more value
and make much bigger strides, much
more progress on your core mission.
Exactly.
And through this whole journey, Cora
learned some really valuable principles
for making these partnerships work.
Principles that finally helped her
achieve the progress she'd been chasing.
Okay.
What were those?
She really saw the power of picking
a specialist over a generalist,
prioritizing partners who build
lasting systems, not just.
Offer temporary services, valuing the
freedom that good operations create more
than just a long list of software features
and focusing on overall strategy rather
than just implementing isolated tactics.
Those are fantastic takeaways for anyone
running a creative business online.
It's not just about
offloading tasks, is it?
No.
It's about finding a partner who gets
your long-term vision, understands
the specific game you're playing.
Genuinely helps you
make meaningful progress
and Cora reflected later.
You know, she wished she'd grasped earlier
that newsletter success just brings its
own unique set of operational challenges
and that trying to DIY it or using generic
help actually gets more and more expensive
in times stress and lost opportunity as
you grow and try to make a bigger impact.
Yeah, she really came to appreciate the.
True value of operational freedom,
as she put it, how it reignited her
passion, boosted her creativity,
and ultimately unlocked that
progress she'd always envisioned.
So for everyone listening now, maybe
some folks are hearing echoes of
Cora's story and their own experience.
Mm-hmm.
What are some key questions
they should be asking themselves
about their own progress?
The obstacles they're hitting.
Yeah.
It really starts with some
honest self-assessment.
Take a hard look.
Yeah.
How are you really spending your time?
What percentage is truly on creating the
stuff you love versus everything else?
Mm-hmm.
What are the biggest things
currently stopping you from
hitting your growth goals?
How confident do you really feel managing
all the technical bits and pieces?
Are you maximizing your revenue potential?
Are you making the impact you want?
Maybe the big one.
Yeah, maybe the biggest.
Does running your newsletter feel like
it's empowering you to create and grow and
make progress, or does it feel more like
a drain, like something holding you back?
Right.
If you find you're spending, let's
say, more than 25% of your time just
on operations, or if you just feel
trapped by the demands, it might
genuinely be time to explore if a
specialized partner could be the key to
unlocking some serious progress for you.
Good benchmark.
Ultimately, remember the mechanics,
the tech stuff, it matters, but it's
secondary to your message, your content.
The right partner protects your creative
energy so you can focus on sharing your
unique voice and achieving your goals.
That's the real end game.
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