Solopreneur Doorway

Issue 2

Read time: 9 minutes

The View from Erik’s Doorway

Email: LinkedIn:


It’s 24/7, 365 days a year. 

In 2023 there are 347.3 billion emails going back and forth around the world. (1)

347.3 billion.

Every. Single. Day.

So, with all that email hitting you morning noon and midnight I’m curious.

What’s your 24/7 strategy with email?

After all, you create them when you go to bed, wake-up, drink coffee, sit at a traffic light, make dinner and sit on Zoom calls.

Are you a passive email user or is email a daily, active campaign to spark sales for your business?

Do you create the 5 day funnel, the 30-day funnel, cold emails to introduce yourself, warm emails to keep the chat moving and hot emails to close the deal?

It’s near impossible to imagine your solo biz without an effective email funnel and strategy.

How else can you sell smart SaaS solutions, online course and coaching expertise?

You must have email, right?

If you’re Cal Newport you write about a world without it.

When I read, “A World Without Email” in 2021 my highlighter was frantic.

Newport tells us.

• Email makes us less productive.
• Email is the pest that eats up our time since we check it too much.
• Email makes us multi-task, which means we perform worse on more tasks.

In his book, Newport sites stats on our email habits that’ll make your mouth drop and your keyboard freeze.

His insight is electric and his perspective sobering. I think you’ll like it.

I was a passive email user in my first business.

It was a tool to touch base, confirm appointments, send a summary or ask about new ideas.

I had no email campaigns and seldom responded to inquiry emails from new companies.

That was ‘yesterday.’

Today, email plays an active, daily role in my business. As of this writing, I’m creating a strategy to provide edutainment and insight on how to solve 1 BIG problem for your clients.

And it’s going to include emails.

It’s a process I enjoy and one where I collaborate with professionals who know what to do.

And since I’m deep into emails and how they can help your business here’s what has my attention:

Email and AI are teaming up for some BIG changes to email strategy and they’re arriving at light speed.

They’ll make you happy, angry, frustrated and ready to re-evaluate how a 50-year old technology shapes your solo biz strategy.

Thank goodness we have email strategists like Toby Myles.

Toby brings clarity on how email can drive your sales and how a stellar email strategy can impress and win clients. Her journey is remarkable and her creativity is sharp.

The Interview Stage

Niche or Passion? How Toby Myles Found Both with Email Strategy

Toby Myles
Toby Myles

It’s tough starting a side gig while keeping up with your full-time role.

When you pivot from freelancer to full-time solopreneur the puzzle gets more complex.

While a handful of solopreneurs find nirvana in their first attempt to mix passion and niche it’s more common to visit many destinations before you find the ideal spot.

You tackle 2 constant questions.

“Are you solving a BIG problem?”

“Will folks pay you to solve it?”

Toby Myles faced these questions when she launched her exciting solopreneur journey.

Toby’s ascent to exceptional email strategist reminds us how tenacity, skill, family support and timing shape the solo path.

For 30+ years Toby has gained insight and implemented valuable strategies in direct response marketing.

She is a certified email strategist, copywriter, copy coach, and best-selling author.

She is the founder of Toby Myles Copywriting and The Big Juicy Copy Club.

Toby has a passion for helping solopreneurs expand their businesses with a fun, helpful and authentic writing style.

When I receive an email from Toby I pay attention. Her writing approach sparks my curiosity.

Toby chatted with me from her workspace in Pennsylvania.

She was funny, candid and direct. All the qualities you want from your email specialist.

Erik: “Toby, take me back to the first days when you were thinking, ‘I’m going to go out and build something on my own. I want to start a firm that I can be proud of.’
What was going through your head when you started that adventure?”

Toby: “I was a project manager. I <coordinated> huge email and direct mail campaigns for a lot of nonprofits.

I really wasn’t writing per se. I was managing a team of creatives, copywriters and designers. Copywriting was something I always loved.

I was at that company for 15 years and actually built a totally different business on the side.

I thought that was what I was going to quit my job <and launch> a jewelry business.

In 2019, I had gotten a promotion at work and I was miserable in the new job.

I was reporting to someone else that I didn’t get along with. And I just was not happy. I was stressed and I wanted to leave. And then my husband got sick. He was diagnosed with cancer.

I thought, okay, well, now I can’t leave because now I have to be the responsible one and stay here. And we had a heart to heart one day and I said, ‘I just I don’t know what to do. I’m so unhappy and I don’t think I’m going to last.’

And he said, ‘if you want to do this, you should do it.’

Because why not? He was retired. He had his military retirement.

He said, ‘I’m sure you’ll be successful, but you’re not going to be homeless.’

So I gave notice at my company that I was going to leave at the end of 2019 to work on this jewelry business.

But I thought while I’m doing that I’m going to pick up some copywriting clients because it’s something I’ve always wanted to do. And that’s what I did.

There was no strategy or plan. It was <a> willy nilly, ‘Can I write for you?’

I was writing whatever somebody would pay me just to get the experience and to learn and to start to build.

One client led to another, led to another, so that by the end of 2019, I was getting referrals and the copywriting business was taking off.

Then I sustained an injury to my hand and had to have surgery which kept me out of the studio.

That further reinforced what I felt was supposed to be… divine intervention or whatever you want to call it.

Honestly, it’s almost embarrassing, but I went into it with zero plan.

I had a few clients and I took everything. I didn’t care what kind of writing it was. I was writing pretty much anything that anyone needed.  Blogs and emails and product descriptions and web pages.

That was the beginning.”

Can You Shave Your Way to Wealth?

Your Case Study

Source: Giphy

How often do you shave?



Once a month?

Whenever the mood strikes?

While some of you might be shave aficionados and spend big bucks for a sensational shave experience others don’t think twice about their blades, lotions and creams.

As long as you keep it quick, safe and hygienic who cares, right?

One company decided to care and made a ton of money.

The Dollar Shave Club (“DSC”).

When DSC decided to go after Gillette in the consumer razor and blade market they needed a sharp email strategy.

They knew that to defeat the big G (or at least trim their market share) they had to build a loyal consumer community.

After all, a direct to consumer sales and distribution strategy hinges on how fast and for how long you can curate and cater to your online community.

DSC crafted and put forth a 3-pillar email strategy to get their community shaving with a smile.

  • Humor and Storytelling
  • Automated Replenishment
  • Upselling and Cross-Selling

DSC knows ‘edutainment’ matters.

They crafted a tone of voice that brought their community a carefree personality and a company that was serious about, well, not taking themselves that serious.

Make no mistake.

The DSC email campaign is a masterclass.


  1. Introduce and explain the process.
  2. Ask your customers the ‘burning’ question.
  3. Get your customers back to their cart.

Key Takeaways:

  • DSC implemented automated email campaigns to remind customers to replenish their grooming products based on usage or subscription cycles.

  • By providing convenience and making reordering seamless, they increased customer loyalty and generated recurring revenue.

  • By analyzing purchase history and preferences, they personalized product recommendations, leading to increased average order value and customer lifetime value.

Cool New Tools for Your Solopreneur Biz

Here’s what I’m reading and using these days to level up my AI, email and biz strategy game. I have no affiliate links or business ties to these folks. 

💥 Brian O’Connor and Adriana Tica write excellent newsletters.

Brian tackles biz strategy and Adriana explores growth ideas to make your business excel.

Check out their ideas here:

👉 Outlier Growth:

👉 Ideas to Power Your Future:

📝 Cal Newport’s Books Help You Slow Down, Focus and Get to Work
Deep Work
A World Without Email

I’m exploring these tools for email campaigns.
📌 Drip

📌 Moosend

Source: Giphy

Toby Myles Interview, cont…

Erik: As that work started to find its way to your doorstep the biggest surprise you had as a freelance copywriter was what?

Toby: “I started out thinking that I was more of a content writer, long form content and blogging. I realized I didn’t enjoy that as much as I thought I would.

Part of it is the way my brain works.  I’m very conversational in my writing. I realized I’m actually more suited for short form. Social media, captions and email.

I feel <many> solopreneurs don’t think when they go out there. But when they are doing the actual work, unless they’re building a side hustle in that niche, sometimes it takes actually doing the work to realize, ‘wow, I love this or no, I want to pivot in another direction.'”

Erik: “If you were to go back, any changes you might have made that would have simplified that starting process or maybe given you a stronger base to get the business going?”

Toby: “I would not recommend doing things the way that I did. I was lucky because I was connected in the jewelry industry.

I had a jewelry business and those were some of my first clients. I kept getting referrals because this person knew that person.

In my <jewelry> business, I was doing all the things right. I was taking all the courses and mentorships and learning how to grow a jewelry business.

I was smart enough to know I needed some guidance and structure for a totally separate business. I would definitely recommend working with a mentor or coach.

And if you can tolerate a full- time job to build it on the side because it takes all the pressure off.”

Erik: “You and I see volumes of posts that have opinions on email marketing. The biggest myth about email marketing is what?”

Toby: “That it doesn’t work. I hear from some of my clients who balk at implementing it. But yet statistics show over and over again, still to this day, that it’s an important part of the strategy.

I don’t think social media is the only way.

I don’t think email is the only way. I don’t think blogging is the only way. I think email has a strong place in the overall strategy and I think that’s the biggest myth.

And people think that email is dead, but it’s not.”

Erik: “When you strategize with a new client, what steps do you go through with them to help find their voice and to get you comfortable with writing the way they’d like to write if they had your expertise and background?”

Toby: “If a client comes to me and they’re maybe a little bit more savvy and maybe they’ve worked with someone before and they have some background like voice of customer research or voice of customer data then that is really helpful.

Actually take note of the way that they say things, because we use their exact language in somebody’s emails.

When the person on the other end hears that language, they think, ‘Oh my gosh, that sounds just like me.’ Well, it does sound just like you because it is you.

It starts with research. I would say probably a minimum of 75% of my time, especially in the beginning with a new client is spent doing research…voice of customer, customer interviews, Google research, competitor research.”

Erik: “What are you excited about with respect to AI and what gives you pause as you look at AI from the standpoint of an experienced writer?”

Toby: I think right now it’s the buzz. You can’t be on social media and not read every other post about ChatGPT.

I feel it will settle to some point, but it’s not going away. It’s up to us. I feel I have a responsibility as a writer to understand how to use it responsibly.

I am in the early stages myself of researching how to use it to create an outline or how to use it to help brainstorm ideas or how to use it to optimize existing copy to make it better.

I coach students and young business owners early in their journey on writing copy. And that question comes up all the time. ‘How can I use it? Do you use it? What do you think about it?’

I want to be able to answer in a way that shows that I’ve done my research because it’s not going away. People are using it and will continue to use it.”

Erik: “If we put you in a town hall and somebody raises their hand and says, ‘I love to write. I want to become a content email writer.’ What would be the two pieces of advice you’d give them?”

Toby: “I think it’s great to work for somebody else and get some experience, get some training and be able to do it in an environment that is low stress and ripe for learning because I think you can go more quickly that way.

I’m kind of a risk taker. It’d be hard for me to say to someone, ‘Don’t do it.’

I feel like if somebody is that passionate about doing their own thing they will find a way to do it. The responsible part of me says, ‘go work for somebody else as a copywriter, <and> get some skills for a few years.’ I don’t think it has to be that that long and then start to pick up some freelance clients on the side.”

🔎✔️ That’s a wrap for this issue.

🚪🚶Stay curious and keep opening doors.

Who Should I Interview Next?

I’m always on the lookout for dynamic solopreneurs who want to share their story.

Drop me a note at if you have an ideal interview candidate.

If you are starting your solopreneur biz or ready to improve your current strategy there are two steps you can take.

  1. Visit for resources and strategy ideas
  2. Coordinate a 90-minute strategy session: We can start your biz on the right path or tackle the root cause of problems you want to fix today.

Book a Session with Erik

Note: Coaching sessions are with Erik and offered through Thinkaday, Inc.

Let’s connect on LinkedIn.

Solopreneur Doorway is a Thinkaday, Inc. publication.

© 2023 ThinkaDay, Inc. All rights reserved.

, and ThinkaDay are trademarks of ThinkaDay, Inc.


  1. “How Many Emails are Sent Per Day,” Oberlo, July 18, 2023, to recent data%2C worldwide,day registered at 333.2 billion.