How 3 Entrepreneurs Built 6-Figure Businesses by Sending Daily Emails

There’s an old adage in the world of direct-response advertising:

“The money’s in the list.”

When it comes to email marketing, though, it might be more accurate to say that the money is in your relationship with your email list.

It’s not just about your total subscriber count; it’s about how many people look forward to every email you send. Even if you’re emailing them seven days a week. That’s the kind of audience that can take you from an email list to a 6-figure business.

And recently, I talked to three entrepreneurs who have taken that exact journey.

Here are three entrepreneurs who built entire businesses around sending daily emails:

In the Q&A below, you’ll learn their tips and tricks for making the daily emails model work for you. I can’t wait to hear what you think in the comments.

Question: If you’re thinking about emailing subscribers more frequently, how do they keep that list engaged? How do you send daily emails without burning out your list?

Ben: There are a few ways to keep people hooked via email.

The first thing you can do is entertain people. The second is educate people. And the third thing is you can elevate people. Very few email copywriters do the last one—elevating or inspiring prospects—because they either don’t know how or they don’t understand how important this is.

You can tell just by going through your own inbox. I mean, 99% of emails don’t even do one of these. If they do anything, they just try to educate. But without storytelling, or at least attempting to get people to think differently about something, you’re not really expanding people’s minds. You’re not really giving them a reason to listen to you.

If you can get someone thinking differently about something, that’s how you make sales. That’s how you get people to bond with you, instead of just being some faceless company. That’s how you get people looking forward to what you’re writing next.

PhilipThe first thing to understand about daily emails is that it’s a daily thing—and the most powerful habits are daily habits, not weekly or occasional habits. I think that part of having people want to read your emails is that you just send them something every day, even if it’s not great.

That creates an expectation that at 6 AM Pacific every weekday, I’ll be sending them something useful or entertaining. And it’s almost always on a topic that’s interesting to me—and that comes across in the email.

I also don’t just teach in every email. I try to lead with a story or concept, and then transition that into a lesson. The idea of “infotainment” and giving people one nugget of insight per day has helped me maintain open rates of 25% to 30%.

Question: When you’re writing daily emails, what does your automation setup look like? Do you send these emails as new broadcasts from day one, or are you moving people in and out of campaigns?

Jonathan: Most of my subscribers go through a five- or six-email sequence first. I call that my “orientation sequence” after someone downloads a lead magnet. Then I follows up with more emails related to the lead magnet—whatever topic led them to opt in.

Then, after the orientation sequence, I use an automation rule to start a workflow that moves subscribers into the central daily broadcasts.


Jonathan pulls new subscribers out of his “orientation sequence” and puts them into his Central Broadcast workflow.

I have one email that says, “FYI, you’re gonna start getting these daily. Unsubscribe now if that sounds bad.” Most people do stick around to at least check out the daily emails. But I think it’s good to give them a heads up.

move to central broadcast workflow

Philip: As far as automation, I keep it pretty simple. I do use email personalization to customize the calls-to-action in my emails. So if someone has bought my low-end product, The Positioning Manual, they won’t see calls-to-action to buy that anymore.

Instead, they’ll see calls-to-action for my next tier of products—like my group coaching program. I use Liquid in Drip to set up this email personalization.

Using Liquid, Philip pitches different products to subscribers based on their tags in Drip. Aside from the CTA, the rest of each email is the same for each subscriber. Note: to learn more about Liquid, check out our beginner’s guide to email personalization.

Question: What does your daily email writing ritual look like?

Ben: When you go to a party, everybody always asks, “What do you do for a living?” and I never knew how to answer that question until a couple years ago. I started saying, “I’m like a bum, but who gets paid.” I wake up, I let my dog out, then I write an email to my list—and that part of a day, that’s the essential part of the day for me.

Writing my email is the main thing. I’m done, and now I can go do other things. Maybe I write novels, or I work on something as a joint venture with someone else in another business or something, but the main thing is done within 10, 15, 20 minutes a day on most days. It’s just because I have my business down to a one-email-a-day business structure.

My routine is all over the place—some days I email my list first thing in the morning, and other days I write at night. It also depends on when I get ideas for emails.

On the point of email ideas, one easy way to get ideas for copy is to answer questions your subscribers ask you. That’s probably the easiest way.

I don’t necessarily answer questions immediately, but some people do send me a direct email and I will answer them directly, and I’ll say, “Hey, this is a great story,” or, “This is a great question—would you mind if I shared it with the list?” And they almost always say, “Sure, go ahead.”

The next day I might tweak the question and answer a tiny bit for clarity, but usually, I don’t even change it that much. Usually, I just send it out as an email and say something like, “Hey, John Doe from the list yesterday asked this great question, and I thought you guys might benefit from it, so here’s what I told him.”

This makes it really easy to stay connected and solve problems for my list every day without having to constantly think of new ideas.

Question: What specific results have you seen in your business since switching to daily emails?

Philip: My daily emails list has enabled me to build an information products business. That’s been huge. It’s helped me keep my mentoring program pretty much 80% full over the past year. That I don’t think I could have done without email marketing and daily emails.

My average value per subscriber is around $38, which is 2–3X the average value per subscriber of most other information product businesses.

If someone is thinking about trying daily emails, I really can’t think of a better way to learn about your market. Try to create an email list that’s so valuable that people willingly give you a minute or five minutes of their time every day. If you can do that, you have what you need to run a successful business.

Build a Hyper-Responsive Email List with Daily Emails and Drip

If you’re curious about the daily emails model, but you’re convinced that you would annoy subscribers, there’s a great way to test that assumption.

With Drip’s forever-free Starter Plan, you can import up to 100 subscribers at no cost. That means you can import a few subscribers, let them know you’re going to try daily emails, and see what happens. You might be surprised to see an increase in value-per-subscriber, engagement, and word-of-mouth around your business.

To get started in Drip, all you have to do is…

Click Here to Get Started with Drip for Free

I’d love to hear what you think of the daily emails marketing strategy. Would you try this as an experiment in your market? Post your thoughts in the comments below.