Seven years ago, when I started my business I had no idea what a copywriter was or did.

I was a school teacher, but I was desperate to start an online business that could get me out of the classroom.

After starting a few wildly UNsuccessful strength and conditioning blogs, I pivoted to the “wrestling coaching” niche.


The niche didn’t really exist at the time.

I was a former Division 1 wrestler and a high school wrestling coach. And I loved it. And I knew the sport had a ravenous following throughout the country.

But there was not a ton of good online content for this sport.


I figured I’d start a site called Wrestling Coach Academy and start publishing content and start creating some digital products.

One of the people I followed from the very beginning of my journey into entrepreneurship as a guy named Ryan Lee.

I gotta tell ya…

I cannot say enough good things about Ryan.

Maybe it’s because he’s an East Coast/NYC guy. Maybe it’s because all of his products have made me a TON of money in my business.

I’m not quite sure.

All I know is that for seven years now, I’ve been following everything he does.

Back when I was running Wrestling Coach Academy, I remember I started emailing daily as per Ryan’s advice that I gleaned from his own emails and programs.

And ya know what?

Good things started to happen in that little, fledgling business.

I started to build a following.

I had a dialogue with my audience.

My content even went viral. I had an article get 48,000 views in 3 days.

(Pretty cool, for a 24-year-old kid who had no idea wtf he was doing online.)

At some point though, I realized the handful of affiliate sales I made from Daryl Weber’s Attack Style Wrestling course wasn’t going to pay all my bills.

Around that time, Ryan Lee was offering some speed-coaching calls.

I think it was a couple hundred bucks for 20 minutes.

I paid for that with my paycheck from my teaching job.

I remember I stayed after school one day, because I think Ryan’s only available appointment was like 3:30 pm that day.

I LOCKED my door, so none of my colleagues would see I was having a skype call with an online business coach.

And we had our call.

Ryan has this impeccable knack for getting right down to brass tacks.

I told him about what I was doing with Wrestling Coach Academy. I told him about my list and my daily emails and my weekly podcast where I’d interview the best coaches in the country… and he said I did a good job with all that.

“But here’s the thing…”

Oh shit.

What was he going to say about my business?

“I know a lot of people who’ve tried to make money in this market. It’s kind of tough. Why not try offering some one-on-one coaching calls to people on your list and see if you gt any takers. If you have 350+ people on your list, you should probably be able to sell like 3-5 of those. And if you can’t it might just show you that it’s going to be a tough market to make money in.”

I took his advice.

I sent an email out, offering some skype coaching calls.

I think I was charging like $50?


Ryan… was right.

I always look back on that one conversation with Ryan. Because that was a pivotal point in my career as an entrepreneur.

After that phone call, I told myself… I gotta build a business that has a chance of actually making money.

Could the wrestling site have worked out?


Seven years and at least $40 million worth of online sales experience later (for my clients)… I 100% agree with the advice he gave me back then. There’s STILL no one making money in that market selling courses and info-products.

One of the things Ryan encouraged me to do was to build my business around something I was excited about.

The ONE thing I loved more than anything about my Wrestling Coach Academy site was writing daily emails.

It was so much fun… even tho I made very little money doing it.

I loved the dialogue with my list.

I loved writing.

I loved watching myself get a little better each day.

And I was amazed that I had a few hundred people who actually liked the stuff I wrote.

It was because of my conversation with Ryan Lee all those years ago that I decided to “pivot” what I was doing and instead find a way to get paid to write emails.


Here’s the thing.

Nowadays, everyone and their mother is an email copywriter.

Back then, there were only a handful of guys who were doing it.

It was Ben Settle, John McIntyre, Andre Chaperon, and Ian Stanley (who was just starting to become a big name).

Perhaps there were others… but those were the only guys I knew who “made a living writing email.”

So this was still kind of uncharted territory for me.

Because it seemed like every copywriter out there wrote long form sales letters, VSLs, and that kind of stuff.

The point of all this is…

Without Ryan Lee… there is no Chris Orzechowski.

The guy has been such a huge influence in my life.

I’ve invested in so many of his products and they have literally changed the course of my business. He’s someone I continue to not only learn from… I try and hire him for coaching calls every chance I get.

And for this week’s Email of the Week, I wanted to pay homage to one of, in my opinion, the World’s Best Email Copywriters.

So this week, we’re going to take a look at Rewind, which is Ryan Lee’s e-commerce brand.

Ryan is a guy who eats his own cooking.

And when I think of Hall of Fame email writers, he’s a first ballot pick.

Rewind is a company who does email SO RIGHT.

In fact, Ryan has said that over 90% of Rewind’s sales come from email.

When you see his email game, you’re going to quickly understand why.

Let’s take a look at what makes Ryan Lee’s e-commerce email marketing game so damn good.


Without further ado…

Let’s dive into this week’s Email of the Week!

This is the 25th installment of my Email of the Week series. (Catch up on previous episodes here.)

And in case you’re new around here, here’s how this all works…

The Rules For Email Of The Week

Each week, I go out into the wild to find a super-effective e-commerce marketing email… and I break down what made it work. My goal is for you to tune in each week, so I can teach you strategies and best practices YOU can use to make your own emails better.

I find these emails in my inbox, but I also accept suggestions from readers who have a remarkable email they’d like to share.

If you recently received an email that was so awesome it made your jaw drop, I wanna see it.

Forward it to me (chris at theemailcopywriter dot com) with a brief message about what you liked about it. If I choose to do a breakdown of the email you sent, I’ll give you a shout out and link to your site.

The only rule is… you can’t pick yourself.

Now then, without further ado, let’s check out the Email of the Week!


Today we’re actually going to look at THREE emails from Rewind.


Isn’t this EMAIL of the week, not EMAILS?!?!?


But to be honest with you, I had such a god damn hard time narrowing down which email from Rewind I wanted to use, that I settled for three.

On top of that…

There are so many good things that Ryan does with email, I wanted to make this a masterclass in email writing.

Now, before we go any further and take a look at the copy…

I need you to understand Ryan Lee’s email philosophy.

Ryan has a course called 1-Email a Day, which is absolutely fucking phenomenal… and you’re an asshole if you don’t buy it after reading this.

Ryan believes in utilizing the methodology of daily email, because that’s not only how you build a bond with your subscribers… it’s also how you make a ton of sales.

When I was creating the content for my Pay Yourself First email writing course  (which outlines my own system for e-commerce email marketing, based on my own personal system I use with my own business and my clients)…I looked around the market at companies who seemed to have the same kind of mentality when it came to their own email marketing.

Ryan Lee’s Rewind was one of the companies I always thought embodied this philosophy and style of email marketing… and it gave me a lot of inspiration for the kind of work I do with my private clients, when it comes to email.

Another company that seems to believe it’s worthwhile to “pay themselves first with email” is Truvani. Another one is Underground Cellar.

(BTW: None of these companies, including Ryan’s, used my system – just FYI. But they are committed to consistent email follow up, which I DO teach in my course.)

Companies like Ryan’s – who stay dedicated to writing awesome emails – tend to enjoy higher profits, more brand loyalty… and a streamlined business model. Ryan gets up, he writes an email, puts some money in his pocket… and then takes care of all the other things in his business.

Ryan’s model for running his businesses had a huge inspiration for my own belief and philosophy when it comes to email.


Let’s take a look at one of Rewind’s awesome emails so you can see Ryan’s skills in action…

Rewind Email #1


Subject line: obviously you know I don’t love title casing… but Ryan doesn’t normally do this.

He’s always got great subject lines and normally they’re not title-cased. They look super personal.

This one’s pretty cool…

Because it kind of hints at a “behind the scenes look” at their process for creating their bars.

So that’s a good little open loop.

Plus… the question mark draws you in with curiosity.


Here’s something Ryan does with his Rewind emails that is actually pretty cool.

Every single time he sends an email, he includes a GIF.


How many companies waste this space above the copy with a GIGANTIC FUCKING STOCK PHOTO… or their logo (which always seems to engulf the entire screen), which we’ve all seen a million times?

Ryan is smart about the way he uses this space.

The GIFs make you laugh… and they continue to draw you in with curiosity.

And he always seems to relate them to the copy in the emails.

Look at that first line of copy, to see this in action.

It’s funny.

His target market relates to the GIFs.

It’s very smart.

Ryan does a great job of ALWAYS keeping his emails timely, fun and interesting.

What he does NOT do is ram sales down people’s throats.

Why doesn’t he do that?

Because he probably knows that’s a good way to burn out your list.

People don’t NEED discounts and flash sales to buy.

But they do want to have a relationship with your company.

They wanna feel like they know you.

Ryan does an incredible job of sharing stories from the work he’s doing in his company. He’s always taking you behind the scenes and letting you know what’s “happening on the floor.”

You wanna know why this is so brilliant?

Because this approach will NEVER get old.

In this block of copy, Ryan’s letting you know about what’s going on with their products. He’s got some links, so you can buy.

He’s writing to achieve his objective – to make sales – that’s for damn sure.

But he’s doing it in a super cool, super casual way.



So this email transitioned from here’s what’s happening now… to hear’s some cool stuff coming soon.

Ryan is a master of building anticipation for his products.

What’s really cool about this copy block is how Ryan rehashes Rewind’s value prop.

That is something that’s ALWAYS present in his emails. He’s always reminding you why his products are so awesome.

Also take a look at this delicious little piece of visual persuasion: “And since we don’t use anything artificial – we can’t just cook-up chemicals (like sucralose or sugar alcohol) in a bunsen burner to jam in our bars.”

Ok. We need to dissect this…

I’ve always told you that the secret to injecting your writing with visual persuasion is a combination of specific details + powerful verbs.

  • cook-up
  • Bunsen burner
  • jam in

These words create visuals in your mind. They’re sticky. They get you to “see” all the shady practices Ryan’s competitors are using with their own bars.

This is really good copy.


Ryan also does a great job of being polarizing. He’s basically saying:

“Hey, if you don’t like us… that’s fine. There’s a synthetic bar out there for you! But it ain’t us.”

He’s forcing you to take a stand.

Are you with Rewind… or are you willing to eat fake food from the other guys.

This is a really powerful line of copy.

The rest of this email is building anticipation for good things to come.

When I read Ryan’s emails… I feel a sense of “momentum.”

I know it’s kind of weird to think about.

But that’s the ‘feeling’ I’m left with.






I literally FEEL that way when I read Ryan’s copy.

His positivity is infectious.

I think that’s one of Ryan’s biggest copy secrets… he uses his words to change your mood, for the better.

Really awesome stuff.

Let’s take a look at how he signs off…



Ryan traditionally includes another, reinforced CTA in his PS’s.

He usually pitches within the body, but it’s a soft pitch. And he tends to save the stronger, more blatant CTA for the PS.

People start to learn that Ryan has a value-first mentality when it comes to email. And THAT is part of the reason they keep coming back for me.


One thing Ryan does in his emails that I haven’t seen anyone else in the e-com world do is… he SHOWCASES his customers in EVERY email.

This is probably one of the most effective comunity-building strategies I’ve ever seen.

Ryan is building a TRIBE, not just a company.

He’s making his customers the heroes of the brand.

He makes his customers feel awesome for taking care of their health.

And he features someone different every single day.

Of course, these are all people who submitted reviews and pictures.

But look at how he constantly takes advantage of user-generated content to help him make sales and grow his tribe even more.

So awesome.

Is it hard to wonder why his customers love his brand so much?


This is a great way to get OTHER customers, who might be a bit more shy, to submit their own testimonials… so THEY too can be featured in a future email.

So fucking smart, this guy.

I gotta tell ya.

This is why he’s the best around.

Rewind Email #2

Look at that subject line.

I mean… it’s perfect.

10 out 10.

Fuck it… 20 out of 10.

It looks personal.

It’s short.

It’s intriguing.

You HAVE to open to see what happened. There’s a hint of a story in those three words. So great.


So this email is obviously from last year. Apparently, Rewind sold so many bars that they ran out of certain flavors… and they’d be out of stock for weeks.

Of course, this was a bit of a problem because some people “built” the habit of eating a Rewind bar every morning to start their day.

Obviously… customers probably wouldn’t be thrilled to hear the news that it was going to take a while to get their bars.

So I want you to look at how Ryan handled this situation.

THIS is why Ryan Lee is the fucking GOAT when it comes to email.

He takes something negative… owns up to it… spins it into a positive… and then uses it to sell.

I mean, as an email copy SNOB, I have to admit… this is truly beautiful.



You know what most companies do if they screw up?

They issue some bullshit apology that their PR person wrote, after getting it approved by legal so they never have to ‘technically’ admit any fault.

Ryan says F that!

He’s a real dude.

He addresses this issue like a man. Takes responsibility for it. EXPLAINS what happened. Shows you what he’s doing about it to not only fix the problem, but also to make sure it doesn’t happen again.



I mean… THIS should be taught in every single business school around the world:

How to Handle Your Shit like A Man 101 with Professor Lee

He’s open.

He’s honest.

He’s REAL.

This is not a corporate robot speaking to you.

This is a human, a real flesh and blood person.

So many ecom companies send their emails “From the ____ team :)” or some bullshit like that. No one has to take any responsibility.

Not Ryan.

This is why the guy is successful at everything he does.

He’s got integrity.



Again, we see the blatant PS call-to-action.

And a picture of a new bar flavor.

Followed by the Rewinder of the Day…


Rewind Email #3

Ok, I know this is my longest EotW yet but bear with me.

This last email is REALLY good.

I’ve got a question for you…

How do you ignore that subject line?



You can’t.

You’ve GOTTA open up this email to see what the story is here.

Let’s take a look at the body…


Again, Ryan does a great job of always keeping Rewind’s products top of mind.

Again… awesome GIF.

But here’s the best part of this entire email…


When you start emailing (or doing any kind of marketing, consistently)… you’re going to rustle up a few trolls.

Case in point:

This mouth breather who’s essentially “threatening” Ryan into giving him a coupon code.


I sometimes get morons like this replying back to my own emails. It’s kind of fun to mess with them.

It’s even MORE fun to make sales at their expense.

Of course, Ryan takes the high road with this guy and explains to him why he will NOT compromise his values.

And he uses this seemingly small interaction as a hook for an entire email.

Ryan recognized this would be a PERFECT example of him reinforcing his values, even when no one is watching.

And he uses this interaction as an opportunity to not only build a STRONGER level of trust with his email list… I bet he made a ton of sales from this.




All in all… just an incredible example of short, simple e-commerce emails that any business owner can model with their own company to make sales.

Ryan Lee… I know you know you’re the best in the business.

But I’m sure you won’t hate me for reminding you of that fact.

Keep kicking ass.

Keep being an example that ALL e-commerce business owners should follow.

And keep being awesome.

For all the business owners reading this, if I can leave you with ONE big takeaway from this 3,200 word article, it’s this…

Write like Ryan.

(Should we make it a hashtag? Let’s make it a thing: #writelikeryan)

Big Takeaways from Ryan Lee’s Rewind Emails

  1. Be real with people.
  2. Tell stories.
  3. Let people into your world, take them behind the scenes.
  4. ALWAYS keep the main thing the main thing: write to make sales.
  5. Good emails aren’t about products, they are about helping people achieve outcomes in their life. The products are there to facilitate the process.
  6. Keep your subject lines short and intriguing.
  7. Make your customers the HEROES of your brand.
  8. Remind people of your USP every chance you get.
  9. Specific nouns and verbs are good forms of visual persuasion.
  10. GIFs are funny.
  11. Inspire people with your copy. They should feel better after reading your copy, not worse.
  12. Have integrity, even when no one is watching.
  13. Have fun with your emails (notice all the 80s references in Ryan’s emails)
  14. Write your emails to one person.
  15. Make your emails come from a real person, with a name… not a faceless corporation.

What You Should Do Now

  1. Subscribe to my email list so you can get ALL of the Emails of the Week delivered straight to your inbox, automatically.
  2. Leave a comment for me below and let me know what you liked about this email.
  3. Send this breakdown to someone you know who has a physical product business. You might help them make a ton of sales with daily emails.
  4. Get on Ryan’s List and buy his Rewind Bars. I’ve actually tried his original Rewind Bars… they were fantastic. Great taste. Nice and light. They are actually a really good product and they have my full endorsement.

2 thoughts on “[Email of the Week #25]: Ryan Lee”

  1. Hi Chris,

    I tried out your email list-building strategy from the “600 subscribers” article you wrote a while ago.

    157 subscribers from 1 Facebook post… and counting.

    You’re the fucking man.

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top
Make it Rain Book

Sign up to get my FREE book on how to generate massive paydays with email