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How 2-Person Agencies Handle 200+ Clients (With Their Sanity Intact)

Let's address the elephant in your Slack channels:

That polite “looks good” email? It carries the silent scream of:
“Who hired these clowns?”

Fact: Your clients aren't stupid.
You know they smell fake expertise from three screens away.

As a smart agency owner yourself, you refuse to pretend to be an industry expert for everything. Instead, you extract clients' actual genius.

But until now the processes for “genius-extraction” relied on a complex, time-consuming setup. And expensive employees.

With Pressmaster one white-labeled conversation link transforms their brain dump into weeks of authentic thought leadership that makes them say:

“Holy sh*t, this sounds more like me than I do.”

And with another click distribution sparking high engagement on all platforms is solved as well.

Without pulling all-nighters. Or burning out your team. Bold promise. We know.

Discover more

Hey,

As I have said, keeping this newsletter only till a certain number of people is a crime

More people should know about Dark Chocolate and its value.

That’s why I started Dark Chocolate podcast.

And that’s why I reached out to couple of top email marketers and In this 2nd episode of Dark Chocolate podcast I’ve got someone amazing who has been doing it for the last 15 years. 🤯

So, say hi to the second guest of Dark Chocolate podcast…

Karen Grill

I will directly jump to the questions and answers.

1. Can you briefly introduce yourself and share what led you into email marketing?

Karen: Sure! As you mentioned, I’ve been in the online world for over 15 years. I started as a business coach, but I noticed that many people were struggling with email marketing. They weren’t getting the results they wanted, and the challenge grew even bigger after last year’s changes in email authentication rules.

I had a background in email authentication and deliverability, so I started helping clients navigate these issues. That’s how I shifted my focus to email marketing and became an expert in helping businesses land their emails in the inbox.

2. What’s one mistake you made early on in your email marketing career, and how did you overcome it?

Karen: The biggest mistake I made was not starting my email list soon enough. I hear this from a lot of people, they think they need to be at a certain level in their business before starting an email list. But the truth is, the sooner you start, the better.

An email list helps you build an audience, understand what they want to hear from you, and write the right message for them. If I could go back, I would have started my email list much earlier.

3. What trends are you most excited about in email marketing right now?

Karen: One major trend is the shift towards highly personalized and segmented messaging. People don’t want generic, mass emails anymore, they want content that speaks directly to them.

We’re seeing this across platforms like LinkedIn, where engagement is higher when messages feel personal. The same applies to email marketing, customizing messages for different audience segments increases engagement and conversions.

4. What’s the biggest challenge you face when building an email list, and how do you tackle it?

Karen: The biggest challenge is ensuring that your list is engaged. In the past, people focused on just growing their email list, but now it’s more important to have a responsive audience.

I tackle this by regularly analyzing my email metrics to see what resonates with my subscribers. I also clean my email list frequently, removing inactive subscribers to maintain high deliverability rates. It’s not about the number of subscribers, it’s about the quality of engagement.

5. What are your top 3 tips for increasing email open rates?

1. Authenticate your emails – Ensure your emails are properly authenticated (SPF, DKIM, DMARC) so they land in the inbox.

2. Analyze your email analytics – Schedule time to review what’s working and adjust your strategy accordingly.

3. Clean your email list – Remove inactive subscribers and send re-engagement campaigns to boost open rates.

6. How to master the art of email copywriting?

Karen: The key is to talk directly to your audience. The best way to do this is by actually having conversations with them. Listen to how they describe their problems and use their own words in your emails.

Keep your emails clear, concise, and relevant. Write as if you’re speaking to a fifth grader, simple language converts better than overcomplicated messaging.

7. How do you approach segmentation and personalization in your email campaigns?

Karen: Segmentation is all about sending the right message to the right people. You can segment based on factors like business type, interests, or past interactions.

For example, if you’re an accountant, you wouldn’t send the same message to someone with an LLC as you would to someone with no business structure. You can also use email clicks to segment, if someone clicks on a link about SEO, tag them as interested in SEO and send them more content on that topic.

8. Can you share a case study or example of an email campaign that delivered unexpected results?

Karen: Sure! I worked with a social media influencer who lost her Instagram account overnight. She had no way to reach her followers, which made her realize the importance of an email list.

We built an email list from scratch using a lead magnet and within a few months, she had under 500 subscribers but was already making sales. She was shocked because it had taken her years to monetize her Instagram. This case proves that an engaged email list is more valuable than a massive but unengaged social media following.

9. For newcomers in email marketing, what’s one piece of advice you’d give to help them stand out?

Karen: Focus on quality over quantity. You don’t need thousands of subscribers, just a small, engaged audience.

Also, commit to a consistent email schedule. Pick a frequency (weekly, biweekly) that you can sustain long-term. People need to see consistency to trust your brand.

10. Where do you see the future of email marketing?

Karen: The future is all about hyper-personalization and better deliverability. Google, Yahoo, and Outlook are cracking down on spam, so businesses need to ensure their emails are highly relevant and properly authenticated.

I see email marketing evolving into a more relationship-driven strategy, where businesses build deeper connections with their audience rather than just blasting generic emails.

11. What is the biggest myth about email marketing that you’ve had to unlearn over the years?

Karen: The biggest myth is that a bigger email list means more sales. That’s not true.

A smaller, well-segmented, and engaged list will always outperform a massive, unengaged list. Quality trumps quantity in email marketing.

12. What tools or software do you use for email marketing?

Karen: I always recommend choosing tools based on what integrates well with your existing tech stack.

For beginners, MailerLite is great because of its free plan and solid functionality. For more advanced automation, ConvertKit and ActiveCampaign are excellent. If you're in the newsletter business, Beehiiv offers great analytics and deliverability.

Make sure to follow Karen on LinkedIn.

Key takeaways

After taking the interview, here are 3 key takeaways:

1. Send email with a consistency

2. Don’t keep people in your list who are uninterested to listen from you.

3. Always chase the quality not quantity.

Thanks for reading the 74th edition of Dark Chocolate.

So I will see you the next week at 10:00 AM sharp.

Till then, byeeee.

Your “email guy” Anirban.

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