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Every issue of this newsletter gives you the exact systems, strategies, and principles I’ve used to generate 8 figures (almost entirely) with email marketing. So you can build your own systems that will carry you through the next algorithm change or recession. This is what actually works.

In today's issue:

  • From Terrified Introvert to $10M in Automated Systems

  • Replay is Live: The $448,978.35 Side Hustle I Run In 15 Minutes Per Day

  • What Email Lists That Make Money Have in Common 

  • Secrets of Email Marketing with Kyle Dana

  • Confessions of an Email Millionaire by Igor Kheifets

“The more honest you are with your true self and others, the faster you will see what really motivates people.” — Gary Halbert

FROM MY WORLD

From Terrified Introvert to $10M in Automated Systems

For years, I thought my biggest mistakes were the things I actually tried and failed at. Like launching something that flopped, picking the wrong partner, or chasing an idea that seemed smart but crashed in front of everyone.

But looking back, the real pain came from the things I barely even tried.

In internet marketing, I skipped entire categories without realizing it. Physical products, Software, SaaS. Not because they didn't work, but because I never leaned in long enough to find out. There was a time we built a piece of email software and spent over $200,000 developing it—designed to write full sequences, broadcasts, affiliate promos, the whole engine. The software worked. It still works. But I never released it, never properly launched it, never gave it a fair shot, and to this day I still don't have a clean explanation for why.

But the one opportunity I almost walked past completely was webinars.

I got into webinars five or six years later than I should have because I was afraid of them. I'm introverted. I don't love performing. I was convinced I wouldn't be able to carry a room, hold attention, or deliver cleanly without falling apart afterward. So I avoided them, until I accidentally did one with a JV partner who had a list of people trying to build theirs.

That webinar had no plan, no real strategy, no funnel. I taught for about an hour and twenty minutes, answered questions, and at the end, I casually said, "If you want a solo ad, email me." No website. No opt-in page. Just an inbox.

That single webinar kept producing leads and buyers for eight straight years.

People were still finding it, watching it, and messaging me years later. I had never created an asset that produced so much from so little effort, and the crazy part is that I completely botched what most marketers would call the "right" approach. I just spoke honestly about what I knew, what worked, what didn't, and let people decide.

When I finally stopped resisting and took webinars seriously, one of them brought in about a million dollars in a year. Not overnight; Over time, consistently. That same success also got my PayPal account shut down because the volume and refunds spiked too fast, and I remember sitting there for days feeling genuinely devastated, like something fundamental had been ripped away.

Here's the part most people don't talk about: webinars drained me. Two a week made me physically sick. So I learned to automate them, build systems around them, and let the work compound without burning me out.

Those systems have now generated well over $10 million across several years.

The real mistake wasn't fear. It was underestimating leverage.

So think about this carefully. What's the one asset you keep circling around, knowing it could change everything, and quietly choosing not to finish?

MY GIFT FOR YOU

Replay is Live: The $448,978.35 Side Hustle I Run In 15 Minutes Per Day

I run multiple income streams, but not all of them are the same…

One of them requires just 15 minutes a day of effort and has generated me $448,978.35.

It's not even one I built myself. I simply plugged into Dean Holland's system, and it started working for me.

He calls it the "CEO Commission System" and we just put together a training showing how you can clone it for yourself.

Dean's already built everything. The funnels, the emails, the offers. It's all optimized and proven. 

You just plug in and the system pays you $1,000 commissions without ever talking to anyone on the phone.

Dean walks through exactly how it works, including the 15-minute daily traffic method that feeds the entire system. You'll also see real member results from people who went from zero to $10,000+ per month.

If you're tired of the endless content creation, funnel building, and traffic chasing, watch this before it comes down.

MINDSET MAKEOVER

What Email Lists That Make Money Have in Common 

Most people think the job of an email list is to be helpful—to teach something, explain something, break things down so neatly that nobody can possibly object.

That belief feels safe, reasonable, and completely upside down.

When you optimize for "helpful," you quietly demote yourself to the role of a content provider, which is just a polite way of saying you train people to read, nod, and keep scrolling. You become another article in a long list of articles, competing on clarity instead of conviction.

Here's the truth most people don't want to hear: authority isn't built by teaching steps. It's built by shaping how people think.

Look at the email lists that actually print money. Their emails aren't tutorials—they're stories, opinions, comparisons, warnings, announcements, and unapologetic offers. There's personality everywhere, along with friction and direction, and almost no "here are the five steps."

That's not laziness. It's strategy.

If someone joins your list, it's not because they want another explainer—they can Google that. They joined because they want a shortcut to judgment, someone to tell them what matters, what's nonsense, what to ignore, and what to act on now without second-guessing themselves.

That's also why helpful content works on websites but falls flat in inboxes. A lawyer can rank for a search term, explain the process, then convert with a button at the end, but an email list doesn't work like that. They're already there, already paying attention, waiting for leadership instead of lessons.

Talk about problems the way they actually show up. Call out bad thinking when you see it, make comparisons, take sides, and sell things without apologizing or padding it with value-first excuses.

Now look at your last five emails and be honest: were you trying to be useful, or were you trying to be trusted?

FOR YOUR LISTENING PLEASURE

Secrets of Email Marketing with Kyle Dana

I sat down with Kyle Dana, the Marketing Director at Digistore, and within minutes we were poking at one of the most uncomfortable topics in email marketing: sending more emails without burning your list to the ground.

Kyle sees this from the inside. Vendors and affiliates hesitate to email daily, while the ones who do it right quietly dominate impressions, clicks, and revenue. We talked about why relevance beats frequency, how segmentation actually works in the real world, and why personalization has nothing to do with using someone’s first name.

One moment that stuck with me was our breakdown of why email still outperforms everything else, even with rising ad costs and new platforms popping up every year. It’s not glamorous, but it’s reliable, scalable, and brutally honest.

If email is part of how you make money, this episode will challenge how careful you’ve been playing it.

CURATED READS

Confessions of an Email Millionaire by Igor Kheifets

This book exists because I got tired of watching people overcomplicate email while underusing it. Not theory. Not inspiration. Just a straight account of what actually worked, what didn’t, and the uncomfortable trade-offs I had to accept along the way.

What matters here isn’t the tactics. It’s the pattern. Authority beats helpfulness. Consistency beats brilliance. And most money is made by people willing to send the email everyone else keeps rewriting.

If you want to understand how email turns into income without pretending it’s pretty, this one doesn’t dance around it.

RIDDLE ME THIS

Can You Crack The Code?

The more you obsess over me,
The less money you make.
But without me, you make nothing.

What am I?

Think you've cracked the code? Reply to this email with your guess, and see if you're right!

I grow faster when ignored, 
Disappear when chased, 
And only show up consistently when you stop needing me.

The answer is: Confidence.

Reply

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