What I Learned From Bootstrapping My Own Business That Shaped My Done-for-You Email Marketing Service

There comes a point in growing a business when doing everything yourself stops saving you money.

And starts costing you.

You’re not necessarily doing anything wrong. That’s how you got through the startup phase, and you’ve probably gotten pretty good at wearing seventeen different hats.

But now there are clients to serve, decisions to make, projects to oversee, opportunities to pursue, and a million other things competing for your attention.

Email marketing is somewhere on that list.

So you send an email when you can.

Maybe you have a newsletter or send something when you have an offer to promote. You were consistent for a while, and then a client emergency happened, you launched something, or life got busy.

You dropped the email marketing ball.

And then forgot to pick it back up.

Or maybe you are emailing your list.

But nobody seems to be buying.

That’s a big part of why I created my done-for-you email marketing service.

You’re perfectly capable of writing an email.

But is that email helping turn subscribers into clients?

Because writing an email and managing email marketing are two different things.

You need someone who can take email marketing off your plate and actually manage it.

But the story of how I got there starts with massage therapy, four weeks of “marketing classes,” fake ivy, and one truly terrible advertising decision involving grocery store receipts.

I Learned Marketing by Doing Almost Everything Wrong

After graduating from massage school and passing my boards, I opened my massage business.

I had always known I wanted to work for myself and, because apparently my timing has always been impeccable, decided the financial crisis of 2007–2008 was the perfect time to do it.

My first “office” was a room inside a hair salon with pale yellow walls and fake ivy trailing along the open ceiling.

If that doesn’t tell you everything you need to know about where I started, I don’t know what will.

My formal marketing “education” consisted of about four weeks of classes, and I use the word “education” pretty loosely.

We learned how to write a business plan for a fictitious massage business—which, if I were trying to get a loan from a bank, at least taught me the proper sections.

Mine involved converting an old school bus into a mobile massage studio.

Which, obviously, was not what I did when I graduated.

I opened a real business with basically no idea how to grow it and started figuring things out as I went.

I joke that if someone had handed me a book called If You Want to Be Successful as a Massage Therapist, Don’t Do Anything in This Book, I would have opened that puppy to page one and started using it as my playbook.

Deep discounts?

Yep.

Free chair massage?

Did that.

Coupons handed out to small business owners around town hoping they would lead to referrals?

Absolutely.

Donated gift certificates?

You bet.

I was even talked into advertising on the back of a grocery store receipt.

I know.

I didn’t know anything about anything.

I was also a single mom with zero financial cushion or marketing budget. I was working a full-time job that, on top of supporting myself and my daughter, was funding my startup business.

Having a dependent does not give you the luxury of deciding, “Well, this business thing isn’t really working. Guess I’ll quit.”

So I kept figuring it out.

I Decided to Get Serious About Marketing

About a year and a half into my massage career, I was close to giving up.

I told myself I was going to give it one more real try.

Six months.

And if I still wasn’t better off, I’d throw in the towel.

So I grabbed every free webinar, tutorial, template, and guidebook I could find online and tried to adapt what I was learning to my massage business.

With mixed results at best.

Eventually, I stopped looking only for the next thing to try and started learning about the pieces underneath the tactics.

Strategy.

Ideal client personas.

USPs.

Data.

The foundational stuff that makes the visible marketing actually work.

And that six-month ultimatum?

It did not end in some dramatic movie montage where I suddenly figured out the secret to marketing and everything took off.

It turned into several more years of learning what worked, what didn’t, what worked for somebody else’s business but made absolutely no sense for mine, and how to make better decisions based on the business in front of me.

Some marketing activities had a huge positive effect on my business.

Others taught me very expensive or time-consuming lessons.

But one thing became a constant.

Email.

Email Was the One Constant

I had already been building a list through my appointment-booking CRM, but I hadn’t really done anything with it.

Then I switched to software that had built-in email marketing and started sending regular emails.

Clients started telling me how much they enjoyed them.

They’d tell me I was a good writer.

And the emails weren’t just promotions.

I used them to teach people things.

I explained why massage had a cumulative effect and why regular massage could be more useful than waiting until everything hurt before booking an appointment.

I busted myths.

No, drinking extra water after a massage does not “flush toxins.”

No, you cannot effectively roll your IT band.

And icing your plantar fasciitis may not be doing what you think it’s doing.

These are hills I will die on to this day, which is kind of my point.

The emails weren’t just informative.

They gave clients and prospective clients a clear idea of what I believed and how I thought, written in what I now lovingly refer to as my signature sassy-pants attitude.

They helped people understand what I did and why it mattered without every email becoming:

“Hey, I have an opening Tuesday at 2. Book now.”

At the time, I didn’t think:

Aha. One day I shall become an email marketer.

I just knew I liked long-form content.

I liked teaching.

And I liked taking something people assumed they understood and helping them see it differently.

Email gave me room to do that.

And no matter what else I experimented with over the years, email was the marketing channel I kept coming back to.

Then COVID Changed Everything

Fast-forward to 2020.

The state shut down hair salons, spas, massage practices, and aestheticians.

There was no “pivot to Zoom.”

I literally could not work.

But I needed a job.

I ended up working remotely for a VA agency doing social media marketing.

I already knew I didn’t love doing social media for clients the way the agency model required it, but there was another problem.

There were too many VAs and not enough client work to go around.

A lot of the VAs were only getting part-time or even a quarter-time workload, and I was constantly starving for enough clients to make the job financially sustainable.

I had gone from running my own business to having very little control over how much work I had because my income depended on whether the agency had enough clients to assign me.

Eventually, I decided that wasn’t going to work for me.

So I quit and started freelancing.

At first, I tried to be a Jack of All Trades.

Because that seemed like the smart thing to do.

If you can do a bunch of things, offer a bunch of things, right?

Not really.

The Jack-of-All-Trades Model Taught Me What I Didn’t Want to Build

The problem with technically being able to do all the things is that your energy is never centered on one thing long enough for the client to understand the real value of what you offer.

Clients were often coming to me because they needed their marketing to work like rubbing a magic lamp.

Which I understood.

But marketing doesn’t work that way.

And anyone who tells you otherwise is probably trying to sell you something.

Marketing can absolutely become more effective with a good strategy, but “I need money now” marketing is usually where people lose focus because they start chasing tactics.

Let’s send an email.

Let’s redo the website.

Let’s post more.

Let’s run a promotion.

Let’s try this other thing.

Most of the businesses I worked with didn’t have a broader marketing strategy unless I created one.

But they usually wanted the piece that felt most urgent in that moment.

Then they wouldn’t see a fast enough return and would decide it wasn’t working.

And eventually, I had to recognize that my own service model wasn’t helping.

Because I offered so many different things, clients could hire me to fix whichever piece felt urgent without ever committing to the larger strategy behind it.

I knew the pieces needed to work together.

But I had built a business that made it very easy to buy them separately.

That wasn’t just frustrating for the clients.

It was frustrating for me.

Eventually, I realized I didn’t want to keep trying to be a one-person marketing department.

I wanted to do the work I was actually best at.

Strategy and long-form content.

Social Media Has a Place. I Just Don’t Think It Should Carry the Whole Business.

I’ve spent a lot of time working with social media.

I’m not anti-social media.

It has a place.

But after spending so much time working in it, I also had a much clearer idea of why those were the parts of marketing I kept gravitating toward—and what I didn’t want my work centered around.

I wanted enough room to teach something, explain why I believed what I believed, and help someone look at a problem a little differently.

And I didn’t want to spend my career creating content simply because the content machine needed to be fed again.

That’s where email felt different to me.

It gave me room to do the kind of thinking and writing I was already drawn to, without requiring me to become a completely different kind of marketer.

And for the service-based businesses I wanted to work with, I liked the idea of writing for people who already opted in.

These were people who had already raised their hands and said:

“Yes, I want to hear more from you.”

Email suited the way I wanted to approach marketing much better.

It helped me see more clearly what I wanted to specialize in—and what I didn’t.

My Original Offer Made the Important Parts Optional

When I first started offering email marketing services, writing and strategy were separate.

And given the choice, clients usually chose the thing they could see.

The email.

They would come to me and say:

“I need you to write this email.”

So I would write the email.

I would explain why strategy, automations, list management, segmentation, and everything happening behind the scenes could make their email marketing more effective.

They’d usually agree.

And then choose the writing.

At the time, I had literally structured the service so they could.

I had made the other pieces optional and then watched clients treat them as optional.

Eventually I realized that if I believed those things were part of effective email marketing, I couldn’t keep packaging them like extra services someone could tack on if they felt like it.

Managing email marketing needed to include the writing.

The writing couldn’t continue to be the service.

I didn’t want to keep handing clients one piece and leaving them to figure out how to execute everything else when I already knew they probably wouldn’t.

Not because they weren’t capable.

Because they already had too many other things to worry about.

That’s where the version of my service I offer now really started to take shape.

Yes, plenty of business owners could use better emails.

But the bigger pattern was that they were doing some email marketing without anyone being truly responsible for the whole thing.

Nobody was consistently looking at it and asking:

What are we trying to accomplish here?

What does this audience need?

What’s working?

What isn’t?

What needs to be built?

What needs to be cleaned up?

What should happen next?

To me, all of that is part of the job.

It’s not a collection of bonus features I added to make the service look more valuable.

That is the service.

You’re Not Hiring Me So You Can Manage Me

The last thing I want to do is become another person you technically outsourced something to while you’re still the one responsible for making sure it happens.

The more I worked with business owners, the more I realized that handing off a task wasn’t necessarily the same thing as handing off the responsibility for it.

They could pay someone else to do one piece of the email marketing and still be the person carrying the whole thing around in their head.

That distinction mattered to me.

I didn’t want to build a service where I completed my part and handed the responsibility right back to the client.

I don’t need you to become my email marketing manager.

You’re hiring me to become yours.

And I understand why that can be a bigger mental shift than it sounds.

In the beginning, doing everything yourself is often necessary.

Later, it can become a habit long after it stops being useful.

I understand that mindset because I lived it.

When figuring everything out yourself is how you survived the early years of your business, handing something over can feel irresponsible long after doing it yourself has stopped being the responsible choice.

Your business grows, but part of your brain still operates like the person who had to bootstrap every step of the way.

The justification becomes:

“I can figure this out myself.”

“It’s just email.”

And the short answer is, of course you can.

You’ve already proven that.

The better question is whether you should still be the person responsible for it.

I Think the Future of Small-Business Marketing Requires Better Delegation, Not More Hustle

I really hate all the ads promising small business owners they can replace their entire company with a few key tools.

And I’m not just talking about AI.

You cannot personally become an expert in email strategy, automation, analytics, copywriting, social media, ads, websites, video scripts, SEO, AI, and everything else marketing throws at you.

And I don’t think the answer is to hire one person and expect her to be brilliant at all of those things either.

I know what I’m good at.

I do my best work with strategy and long-form content, especially email and blogs.

The places where I get to dig into what someone is thinking, what they care about, what they need to hear, and how all of that affects a buying decision.

There are people who are much better at the other stuff.

Hire them for that.

Specialization isn’t the same as limitation.

We need to stop paying people to be mediocre at nine things when what we really need is someone to be really damn good at one or two.

I’m Nosy and Proud of It

Professionally speaking, of course.

A lot of agencies and copywriters expect you to arrive with your ideal client completely figured out.

Or they ask questions that barely scratch the surface.

I want more than:

“She’s 42, owns a business, likes coffee, and shops at Target.”

Great.

That tells me almost nothing.

Some might go a little deeper and ask whether she’s frustrated, exhausted, or overwhelmed.

Also useful.

But over time, I realized that wasn’t enough for the kind of marketing work I wanted to do either.

I needed to understand why she feels that way and what she’s making it mean.

What has she already tried? What does she believe about the problem? What would finally make her decide:

“Okay. I’m done trying to solve this myself.”

Because knowing the surface-level problem and understanding how someone actually thinks about that problem are two very different things.

And I came to believe the same thing about the person whose name was going on the email.

I want to understand you just as deeply.

Your personality. Your opinions. The things you would absolutely never say.

But more than anything, I want to understand how you think and how that comes through when you aren’t trying to sound like you’re “writing marketing copy.”

Because I don’t want to hand you a technically proficient, grammatically well-structured email with all the relevant information and absolutely no personality.

That’s what AI is perfectly capable of giving you.

I want you to read the draft and think:

“Damn, that sounds just like me.”

That’s the kind of feedback I’m looking for.

Kendra’s Welcome Sequence Needed… Kendra

Kendra, an estate planning attorney, needed a welcome sequence.

When she came to me, she admitted two things upfront.

One, she had tried using AI-generated copy because she didn’t really know what she was doing when it came to marketing.

Two, she wanted someone else to handle it.

She knew writing a series of emails was not the best use of her time, even though she had been a teacher before becoming an attorney.

And like a lot of small business owners who turn to AI, she didn’t necessarily think there was anything wrong with what it gave her.

The copy was smart.

It was professional.

It had all the relevant information.

It was also flat and sounded nothing like her.

Every sentence had that same polished rhythm that makes you feel like you could dance a waltz to it.

Kendra’s professional personality has a no-nonsense teacher quality.

She’s clear.

She knows her stuff.

But the way she communicates one-on-one is warmer and slightly more relaxed, with a dry sense of humor.

The AI-generated version had none of that.

It was also missing something much more important: her reason for becoming an estate planning attorney.

After having to settle her parents’ estate through probate without a will, she realized she didn’t want other families to have to go through the same nightmare.

That context explains why she cares about the work.

It shapes the way she talks about it.

And you cannot swap that out for some generic paragraph about “protecting what matters most” and expect it to carry the same weight.

My job was to carefully blend that no-nonsense professionalism with her more conversational style so the sequence sounded like Kendra sitting across a conference table from a client, explaining why estate planning matters.

That’s the difference between writing something that is technically good and writing something you’d actually be proud to put your name on.

AI Isn’t the Villain Here, Either

As a copywriter, you’d probably expect me to hate AI and assume it’s going to make me irrelevant in two or three years.

But this is another place where my opinion may be a little unpopular.

I don’t think small business owners need to stop using AI to create content.

If you’re just starting out and cannot afford to hire someone to write your content for you, AI can be incredibly useful.

A lot of business owners are using it because they’re overwhelmed.

They need help.

They’re trying to get something done with the time, money, and skills they currently have.

Which is why I get especially irritated watching marketing professionals dogpile on business owners who use it.

Telling someone she’s terrible at marketing, ruining her business, or personally contributing to the downfall of humanity is a very strange way to convince her to hire you.

It’s also not how I treat people.

AI is a tool.

And Kendra’s welcome sequence reinforced something important for me about where the tool stops being enough.

AI can generate competent words.

It can sound polished.

It may even pick up some of your favorite phrases and speech patterns.

But sounding vaguely like you and understanding how you think are not the same thing.

That was the problem with Kendra’s original sequence.

There wasn’t necessarily anything technically wrong with it.

What was missing was Kendra.

Her reason for caring about the work. Her point of view. The difference between how she sounded when she was being “professional” and how she actually communicated with another person.

That experience reinforced something I had already been learning about the kind of work I wanted to do.

I didn’t want my job to be producing technically correct words.

I wanted to understand enough about the person, the business, and the people we were talking to to make good marketing decisions on her behalf.

That requires judgment, strategy, context, and human understanding.

I use AI myself.

I think of AI as a collaborator.

Not my junior copywriter.

And there is one place where I draw a very firm line.

I recently saw someone promoting an “AI twin” for a plastic surgeon to use on YouTube as a way to replicate the trust-building people want from an actual human being.

That’s exactly where I think we’ve lost the plot.

If trust is part of why someone chooses to work with you, creating a digital version of yourself and presenting it as the relationship-building substitute misses the whole point.

So the lesson I took from Kendra—and from watching how AI is being used more broadly—was never “AI bad.”

It was that a tool can help with the work without replacing the thinking or the human being behind it.

And for the kind of email marketing service I wanted to build, that distinction mattered.

About More Than Four to Six Emails

When I look back, creating a full-service email marketing offer makes a lot more sense than it probably did while I was figuring it out.

I spent years learning marketing by doing.

I learned that random tactics without a larger strategy don’t get you very far.

I learned that I’m much better when I’m allowed to go deep instead of trying to be everything to everyone.

I learned that good writing matters, but without the right system behind it, it can only do so much.

And I learned that what many established small business owners need most isn’t another person to complete a task.

They need someone who can own a responsibility.

Yes, I write the emails.

But I also manage what happens around them so you don’t have to keep carrying that part of the business in your head.

The strategy.

The systems.

The list.

The testing.

The decisions.

All of it.

Because you’re not paying me for four to six emails.

You’re paying me to take email marketing off your plate.

You Can Keep Doing It Yourself. That Doesn’t Mean You Should.

I have a lot of respect for the bootstrap phase.

I lived it.

I know what it means to figure things out because there isn’t another option.

But eventually, there is another option.

And if you’re past the startup phase, doing everything yourself may no longer be the thing saving your business money.

It may be the thing limiting how much of your attention is available for the work only you can do.

You don’t need to prove you’re capable of handling email marketing yourself.

That was never the question.

The question is whether you still want to be responsible for it.

If the answer is no, fill out an application for my done-for-you email marketing service.

You keep doing the work only you can do.

I’ll handle the email.

Leave a Reply

Your email address will not be published. Required fields are marked *