You’re about to uncover the most profound lessons from my 18-year career with email marketing. It’s a long read.
However, it’s a giant education to help you get a reliable stream of high-paying clients.
My journey has been interesting.
In 2006, I dove into this world when I launched a $47 digital book (back when you could buy Google AdWords clicks for $1). That venture forced me to master copywriting and email. I later sold that business and moved to write copy for others as I enjoyed that more.
By 2009, I took on my first copywriting project on eLance (now Upwork) for $100 on how to quit smoking. Fast forward to 2016, I went all-in on email marketing, focusing specifically on Business Experts. On Upwork alone, I’ve generated $300,000.
I’ve worked with everyone from coaches and consultants to seven and eight-figure business owners. I’ve sold $8,500 seminars, $2,000 cohort programs, and $3 books. I’ve seen it all.
These lessons are NOT micro-tactics, tips, or “hacks.” These lessons are deep, sometimes unconventional insights you often won’t find elsewhere.
Let’s dive in.
Lesson 1: Center Your Content Around Professional Experiences
The internet is flooded with bullshit artists and people looking for shortcuts to get rich.
There’s no shortage of folks who regurgitate information without any real experience. When you craft emails to attract clients, your personal stories and professional experiences provide exceptional proof.
Testimonials can be hit or miss—some believe them, some don’t. But sharing your own stories, lessons, and experiences over time? That’s gold. They’re unique, and engaging, and only you can tell them.
For example, I once came across an article by a marketer so compelling I saved it as a PDF, fearing it might be taken down. It was something like “How I Made $852,124 Selling Kindle Books In 23 Months.” Why was this content so compelling compared to a generic “Five Steps to Selling Kindle Books” method? Because it came from real experience.
Grounding your email marketing in your own professional journey transforms everything. It boosts your credibility and makes converting prospects into clients much easier.
I created an educational case study titled These 10 Tiny Emails Filled £6,750 Seminar Seats for that reason.
Sadly, some people jump straight from a nine-to-five job to starting a business, with their first venture being teaching others how to start a business. Yuck. Don’t be that person. Anchor your emails with your real-world experiences and watch your client base grow.
Lesson 2: Reputation Beats Subject Lines Every Time
You can brainstorm the flashiest hooks and sneaky tricks to get people to open your emails, but at the end of the day, subject lines don’t matter as much as the reputation you’ve built with your list.
When I join an email list, if the sender spends more time talking about unrelated stories—like their BBQ adventures or ice skating outings—instead of providing valuable insights related to their expertise, I’ll unsubscribe.
Obviously, this can be part of a brand strategy. It works for some. But I think it’s a gamble.
You only get three to four emails to solidify the impression your content creates. People need to see who you are, what you do, and how valuable you are to them.
Ideally, you send your very best content in the first few emails. If you rely only on broadcast messages, your subscribers might miss out on your top-notch material. So, if you’ve got a killer YouTube video, an impactful article, or a compelling case study, make sure those come up first. Show people you know your stuff.
Once they see the value you provide, they’ll think highly of you and will be more likely to open your emails, no matter the subject line. When I open my inbox, the sender’s name matters more than the subject line. Reputation first, subject line second.
Lesson 3: How You Position Your Signup Page Matters
I dislike lead magnets.
The way most business experts market them is deceptive.
I once worked with a new thought leader who offered a report on their signup page. They were getting a 19% unsubscribe rate on email# 2.
Why?
Because they advertised it as, “Download This Report.” People wanted the report, not the emails. People will often sign up with their junk emails or unsubscribe because the wrong expectations were set.
Does “Get my report” get a higher opt-in rate than, “Get weekly tips?” Yes. Does it lead to better long-term customers? No.
In the online marketing world, it’s become acceptable to offer a lead magnet, have someone download a report, and then bombard them with emails forever. We’ve all just come to accept this as normal.
But think about it—would you be okay with this in a physical store?
Imagine you buy a basketball, and at checkout, they ask for your email to send a receipt. You agree, and then they start sending you promotional emails.
You would be even more annoyed if they texted you the receipt and then sent endless promos via text.
It seems harmless, but is it the right thing to do?
Not really.
Sure, it might increase conversions, but it’s not ethical. If I sign up for a lead magnet, what’s going to happen when I get your second and third emails? I’m going to wonder why I’m getting them. That’s not what I signed up for.
Some might say, “Who cares? It’s not illegal.”
True, but if you get subscribers from Europe, it is.
The GDPR (General Data Protection Regulation) requires that data collected through a lead magnet must be used only for that specific purpose.
If you plan to use the data for multiple purposes, each purpose must be clearly explained. Users must opt in with an unchecked checkbox for further communication.
This shift towards stricter data policies is already happening. Companies like Apple are making privacy a big selling point. We’ve had scandals like Cambridge Analytica, and states like California are tightening their privacy laws. It’s only a matter of time before similar laws come into effect everywhere.
If your business relies on a bait-and-switch with lead magnets, you’re going to be scrambling when the time comes. I’d rather build a business that’s ethical and creates a better experience for everyone involved.
If you DO insist on using a lead magnet, do it ethically.
Give people the option to ALSO sign up for regular communications with a separate unchecked checkbox they can tick.
Lesson 4: The Best Breakthroughs Come From Interviewing Subscribers
I recently helped a client, and before they invested heavily in a new seminar, they spoke to their customers.
They discovered that their original three-day seminar was too time-consuming for many attendees. So, they considered a one-day seminar.
We sent out an email survey to gauge interest, and the response was overwhelmingly positive. Based on that feedback, they moved forward with the one-day seminar, which turned out to be a huge success.
Talking to your customers and prospects is crucial for the success of your email marketing. It’s the key to understanding their needs and delivering exactly what they want.
Ask deep, meaningful questions to understand who they are, what they’re looking for, and what content resonates with them.
- Are they already established in your field, or are they new to it?
- What triggered them to start looking for your solution?
- What have they tried in the past to solve the same problem?
- What did they love and hate about those solutions?
Nothing will boost your revenue and profit more than engaging with your customers. This can be done in many ways: ask them to reply to an email, fill out a survey, or participate in a focus group.
Lesson 5: Split Tests Are the Best Email Education You’ll Ever Get
Ever heard of the term “Kaizen?” It’s a Japanese concept that means “change for the better” or “continuous improvement.”
I was working with a client some time ago who had a treasure trove of data. I could see which emails performed well, their open rates, click-through rates, booking appointments, and sales—all tracked back to specific emails. With this information, I could identify which hooks and topics resonated with their audience, which CTAs worked best, and what type of content was most appealing.
This is where split testing comes in. By continually testing different elements of your emails—subject lines, content, CTAs—you can gradually improve your results, just like Kaizen. Split testing allows you to see what works and what doesn’t, providing you with real-time feedback and invaluable insights.
So, make sure you’re constantly testing and refining your emails. Over time, these incremental improvements will lead to more clients and better results.
Lesson 6: Trust Takes Months to Build and Seconds to Break
Always be transparent and honest in your business. My mission with Email Edge is to rid email marketing of dishonest and deceptive practices and help clean up the industry.
I’ve seen people do all sorts of things that cause irreparable damage to their reputation, especially in email marketing. Tricks like using a subject line that says, “XYZ program is closed, you missed out,” only to reveal inside the email that it’s not true and will happen in a few hours—essentially tricking them.
Some marketers don’t disclose they are affiliates for something they promote, depriving subscribers of the information they need to make informed decisions. I’ve seen experts say something similar to, “You subscribed! I’m so happy that I’m jumping around my kitchen in celebration.”
No, you’re not.
And then there are the famous business experts who use “Re:” at the start of their email, pretending it’s a real reply. What does that say about them? It might seem harmless, but the implications are massive.
If you lie about a subject line, what else are you lying about? This is why trust takes months to build and seconds to break.
You may notice that throughout my website, I don’t post financial results in my case studies, even though their identities are masked. Why? Because earnings are implied claims, and the FTC doesn’t like that. I listened to a lawyer recently say in a podcast that even B2B companies now fall under the same scrutiny to regulations as B2C consumers.
Always be honest and transparent in your email marketing.
It might lower your initial conversions and sales, but it will pay off in the long run. Trust is everything.
Lesson 7: Don’t Be Fooled by Only Opens and Clicks
Sales matter most.
I helped a client run a serious email campaign once. It was the kind of campaign that makes you sweat just putting it together. We spent $3,500 to insert an email into a B2B publication targeting business owners. We ran two versions of each email.
One campaign had a 5.6X higher click-through rate compared to the other one. Awesome.
But as the data came in, it became clear that higher click-through rates didn’t translate to higher sales. Despite the impressive click metrics, these campaigns weren’t generating more sales.
The lesson?
Don’t be fooled by opens and clicks. They’re important, but what really matters is whether your emails are driving sales. Keep your eye on the ultimate goal—conversions.
Lesson 8: Promotions with Deadlines Generate Much More Sales
Many coaches, consultants, and other business experts, often don’t want to promote their products for fear of being “pushy.”
Some prefer ONLY sending content-based emails with a simple, “Hey, if you’re interested, here are 3 ways I can help you” If that works for your business and you’re happy with your income, that’s fine.
But after working with clients for more than a decade, I’ve seen that campaigns with deadlines always perform better.
The best-performing email strategies I’ve seen include something like 80-90% value-based content and 10-20% promotional campaigns.
Think of it like TV. People watch for the shows, not the ads. For example, I helped a client with an email campaign for a $1,995 educational product. We found that the majority of sales—probably about 50-60%—happened on the last day of the promotion.
To maximize this, we sent three emails on the final day: one at 7:00 AM, one at 8:00 PM, and one at 10:00 PM. This ensured we captured as many last-minute buyers as possible.
Is this coercion or being sneaky? Not at all. If what you sell is genuinely valuable and helpful, then a well-structured promotion with added bonuses can drive exceptional sales.
Deadlines work because humans are more motivated by the fear of losing something than by the prospect of gaining something. It’s just human nature. By creating urgency, you move your offer from a low priority in someone’s mind to a high priority.
So, if you want to generate significantly more sales, don’t shy away from promotions with clear deadlines. They work.
Lesson 9: Emphasize Knowledge Over Entertainment
Some experts would scoff at this.
There’s a lot of advice around being funny, silly, and sharing over-the-top personal stories.
It seems like being clever, funny, and quirky would help you go viral and get more attention, and it might. However, it might not be the right attention. In the past, I’ve strategized and been tempted by this direction too. Sure, every business is different, and everyone has a unique brand.
But many people pitch the idea of teaching what to do, not how to do it. I disagree. The more in-depth content you provide, the better you’ll sell.
When I reflected on the business experts I listened to as a consumer, I noticed that I ONLY listen to credible experts, not those who make me laugh.
Take Alex Hormozi, for example.
He recently created a video analyzing his content. He found that while his “infotainment” videos—packed with music, graphics, and sound effects—were popular, they weren’t resonating with his target audience: people making $3 million or more.
Some of these individuals had stopped listening. In the comments, others echoed this sentiment.
When it comes to serious business knowledge and experience, credibility trumps entertainment.
Sharing too many personal anecdotes or trying too hard to be entertaining can diminish your perceived expertise.
If I want to laugh, I’ll watch stand-up comedy.
Humor and personality can be assets, but leaning too heavily on them can alienate potential clients who value expertise and credibility, especially if they don’t jive with your sense of humor.
When I speak to the serious business owners I know, they don’t listen to these so-called experts who prioritize humor over substance.
So what exactly is “value?”
In the context of email marketing, I define “real value” as…
“The act of sharing unique and actionable insights (advice prospects haven’t heard before that addresses their specific pain points or challenges.”
Focus on being knowledgeable and credible—it’s the key to attracting and retaining bigger clients.
By the way, I DO agree with telling stories. Yes, even stories unrelated to the main topic can work. But don’t spend 300 words going off on a random topic before tying it into a business lesson. Make them short, fast, and snappy.
Lesson 10: You Don’t Need to Share Personal Details
As I mentioned before, Alex Hormozi is one of the most respected business people online today. You don’t hear him talking about football, what he had for breakfast, or the funny thing that happened to him in the park.
People don’t listen to him to be entertained—they listen to solve major business problems. Sure, some people get more engagement and views by sharing personal stories, and some even talk about their sex lives.
But others, who say basically nothing about their personal life, still succeed. You don’t have to share what you’re not comfortable with.
Focus on providing value and solving problems for your audience. If your content is impactful and your advice solid, you’ll build a following based on your expertise and credibility, not your personal anecdotes.
Lesson 11: Match the Expectations of the Medium
People skim emails.
Think about how people consume email compared to a book, a YouTube video, or an article. Each form of content has its own expectations.
People check their email and clear it out as quickly as they can, often in short spurts of time. That’s why I try to keep my emails under 300 words, ensuring they can be read in 60 seconds or less. This increases the chances of your email being read rather than archived.
I’m incredibly busy, and when I see huge blocks of text in an email, I think, “This person doesn’t get it.” Even email marketing experts sometimes miss this. You have to get to the point—everyone’s busy, and we’re all subscribed to many email lists. Hook your reader right away with something engaging.
Don’t risk your email being starred or archived only to never be read. I once helped a client with a multi-part educational course via email. He insisted on sending lengthy emails, some over 1,000 words, even hitting 2,000 words. Most people aren’t going to read that.
Keep it short, engaging, and to the point. Match the expectations of the medium, and your emails will be far more effective.
Lesson 12: Sending Daily Emails Only Works If You Provide REAL Value
I subscribe to a lot of newsletters and email lists, and one thing I’ve noticed is that many people who send daily emails don’t always deliver real value.
When you’re forced to write daily, you might end up just filling space. Yes, consistency is important, but the quality of your content matters more. Not every day will allow for crafting something truly valuable. Writing daily emails versus three times a week is a massive difference in content creation.
There are people whose daily emails I still subscribe to, but I rarely read them because they lack substance. It’s a shame because it dilutes the overall impact of their communication.
The lesson here is simple: if you want to send emails once a week, do it. If you prefer three times a week, that’s fine too.
Many of the eight-figure earners I’ve worked with send emails three times a week. The key is to provide real value consistently, regardless of your frequency.
Focus on delivering quality content that truly benefits your readers. If you can’t maintain that daily, it’s better to scale back and ensure every email you send is worth their time.
Lesson 13: Subject Line Tricks Won’t Save a Terrible Offer
I worked with a client who had numerous partnerships and joint ventures. Together, we promoted 29 offers as affiliates. I got to see firsthand how each of these courses and coaching programs converted from email to sale or from email to webinar to sale.
What stood out was that the best-selling products were designed to address common objections in the marketplace. These products had superior methodologies and enticing offers. Their solutions were genuinely better than what was already available. Often, they incorporated technology, AI, or software tools to make implementation faster and easier.
A course on its own holds little value. People don’t have the time or willingness to invest in a course, then watch it, and finally implement the information. It’s a hard sell. We saw webinars with 2,000 registrants and barely any sales.
No matter how good your emails are, they won’t save a bad offer. Your subject lines can be catchy, and your email copy can be top-notch, but if your offer isn’t compelling, it won’t convert.
Focus on creating an offer that addresses real pain points with a superior solution. Make it easy for your audience to see the value and implement it. That’s what will drive sales, not tricks with subject lines and clicks.
Lesson 14: Autoresponders Are Magical
Broadcasts have their place, and some people choose to run their newsletters entirely through broadcasts. That works for them. But I choose to run my email list with autoresponders, and here’s why: I have very limited time, so I need to maximize the value I get from everything I do.
On X, Naval Ravikant once said…
“Code and media are permissionless leverage. They’re the leverage behind the newly rich. You can create software and media that works for you while you sleep.”
Most wealth is created with LEVERAGE.
Put in effort once and get almost unlimited mileage out of it long term.
Autoresponders are a force multiplier.
With an autoresponder, you can queue up a year’s worth of emails.
Just like using a washing machine leverages your time (put in clothes, press a button, clothes come out clean), creating high-quality content that is used only once (like in a broadcast) isn’t efficient.
You could repurpose content into a YouTube short, LinkedIn post, or Twitter thread, but these will eventually disappear. However, if you create a valuable email and put it in your autoresponder, whether someone joins today or in three years, they’ll see that same valuable information.
Over time, as you gather data on click-through rates, sales, and opens, you can identify which content resonates most with your audience. Move your best-performing emails to the front of your autoresponder sequence to build relationships quickly.
I worked with a marketer who never disclosed their earnings, but I conservatively estimate they made $10 million a year, running most of their email lists through autoresponders. It makes sense. You can queue up emails and promotions, even setting deadlines for the future.
Autoresponders provide the leverage you need to maximize your time and impact, ensuring your audience receives consistent, high-quality content without constant effort.
Lesson 15: To Make More Profit, Sell More Offers via Email
I once worked with a client who was a master marketer, running about 30 different offers each year. Each offer incorporated similar elements but was unique in its own way. Now, you don’t need to have 30 offers, but you should have more than one.
Survey your list to find out what they want and create a second or third product. You can also sell affiliate offers, with proper disclosures so your subscribers can make informed decisions. The key is to diversify your offerings.
If one offer isn’t performing well, you won’t make much money. But if another offer does well, it can significantly boost your revenue. Additionally, with advertising costs rising, it’s getting harder to do things on social media. To afford these increasing costs, you need to generate more revenue.
Diversifying your offers not only helps cover advertising expenses but also provides a safety net if one product doesn’t perform as expected. More offers mean more opportunities to connect with your audience and meet their needs, ultimately leading to higher profits.
Lesson 16: What You Say and How You Say It is Incredibly Important
A marketer once told me, “Advertising is a spell.”
In the context of email, I think of it more like a deep flow state.
Don’t say something dumb to make them say, “Why did you say that!?” or “Get lost!” or worse, confuse them so they lose interest.
I made a mistake once with an email that took a harsher, fear angle for a joint venture partner. The campaign targeted doctors and it ended up annoying a lot of people on the list.
The response was bad, especially since we were selling to doctors. You have to be sensitive to your audience and avoid creating objections by accident.
For example, I saw someone once write a “21-step process” to complete X task.
21 steps!
Even if a process has 21 micro-steps, it can usually be broken down into five major steps.
It’s all about perception.
You also see emails with lines like, “Hey, you’re looking good today,” which can feel disingenuous and break the reader’s engagement.
Or, “I’m so excited you joined my email list. I turned to my business partner and said, “[Name], joined our list! Whoo!
No, you didn’t.
Be genuine and thoughtful with your words. Your audience can tell when you’re being authentic and when you’re not. Make sure your message resonates without sounding insincere or creating unnecessary objections.
Lesson 17: There’s No Such Thing as a Perfect Email
I spent years deliberating and overthinking my own email marketing strategy. I could crank out emails for clients in 15-30 minutes, but when it came to my own stuff, I’d overthink it. Since 2016, I’ve probably rewritten similar emails for my own list five times. It’s hard to admit, but I suspect many others suffer from this too.
Perfectionism kills any chances you have of creating effective emails. You have to know when it’s good enough and done, which is a fine line to tread. But over time, you’ll change things anyway. You’ll write something and later realize your market has shifted, your direction has changed, or new insights from your prospects necessitate a revamp.
The longer you wait, the harder it gets. You don’t need to make it complex. There are super advanced features in email systems like ActiveCampaign, popular among coaches and consultants. But ConvertKit offers a simpler, elegant way to start.
Don’t get bogged down by automations, tags, and triggers. Just get started with a few short, valuable emails. Load them into an autoresponder and worry about a proper welcome sequence later. The key is to start and iterate as you go, embracing that there’s no such thing as a perfect email.
Lesson 18: Building a List Will Get Harder
I once saw a guy in a Facebook group pleading for help. He used to get 200 likes and 50 comments on every post, but then the algorithm shifted, and he got around 5 likes and 1 comment. He didn’t have an email list, and he paid the price.
Here’s the thing: You don’t own your audience on social media. The email addresses you collect are an asset you own. Even if your Email Service Provider boots you, you can always take your list and upload it into a new system, as long as you have documented proof of permission-based collection.
The opportunity to build a list will eventually become very difficult. Social media is getting fragmented. Think about how many social channels there are today compared to the old days when MySpace was around. Many experts predict more social media platforms in the future, causing people to split off even more.
If you think back to the early days of TV, there were only a few channels. Then came hundreds on cable. With streaming, we had Netflix, and now there are 10 or 15 streaming services. I think the same thing will happen with social media, making it harder to get attention.
Peter Diamandis once said, “The scarcest thing we have is our time and attention.” I agree. This is why advertising costs (i.e., paying for attention) will continue to rise.
It costs more today to get a click than it did 10 years ago, and it will cost even more in the future. Plus, ad criteria and compliance will get stricter. If you haven’t already started building an email list or taken it seriously, you need to start now.
An email list is your most valuable asset. It’s the direct line to your audience that you control.
When you need to generate more revenue, you can put together an offer, send it to the list, and generate sales.
It’s a beautiful thing.
Don’t rely solely on social media. Build your list and safeguard your ability to reach your audience, no matter what happens with algorithms or platforms.
There you have it. The most impactful lessons I’ve learned having written and run email marketing campaigns over the last 18 years.
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