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(AMA) Ask Me Anything About Email Marketing!

Marketing, social media, advertising

Genium

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Subject:
only for people that like {insert your idea}

Body:
If you're not into {a couple words that describe
your idea} then this email will totally ruin your day.

Look...

I plan on {insert your idea} but I don't want to
annoy everyone else that will not be interested.

So if you want the entire scoop make sure you
you're on this new email list {insert link}.

That way we can talk about {your idea} to our
heart's desires.

Love,
Your name <3
---------------------------------

Then, continually follow up with those that have clearly stated (by opting-in the new list) that they are interested.

And yes you can send your longer messages to the people that will actually read and appreciate it (granted it's not long-winded).

Thanks for the feedback, I really appreciate it. I rewrote my email, sent it out to 700 people, and so far a day in I have 14% open rate, 37 unsubs from the mailing list, and 1.3% click through rate (like 10 people). Hope to see an increase in the next few days but we'll see.

I have been deleting the unsubcribers from the list just to make sure I don't email them again. Would you reccomend sending another email to the people that didn't even open the email? I feel like sending an email in the style you reccomended, but just about the benefits of my product
 
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thecalmpickle

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Thanks for asking this question. I am editing my original answer: yes, they can do online purchases and hotline data. I never would have known to ask those questions! Thanks a million.

ECONOMICS
In any event, in looking at conversion information/assumptions - I think 10,000 email addresses (to an apparently good, bought list) with a good strong letter going to a pretty good optin offer/page) should result in about 10 optins and 2 sales. If so, then my cost per customer would be about $225, which is acceptable in the first phase (not great, but acceptable).

By comparison, a snail mail campaign to 1,000 addresses (3 mailings to each) would cost $2,800 and result in anywhere from 10 - 30 sales (maybe). It's a more expensive initial investment - and I'm a bit nervous about shelling out that much w/o any real confirmation that it will work.

I supposed I could pick 100 names and just make up my own cards and send them through Snapfish, for example, to test...

hmmmmmm.

First of all - I do not know the source of your list or the behaviors of the people on that list.

But with that said, I think your assumptions are TOO LOW.

If you only get 10 optins and 2 sales from 10,000 emails that is terrible. Yes, it could be your offer, but I'd want to know how well that list is nurtured by the list owner first.

At the BARE MINIMUM - I'd expect a 0.05% Conversion Rate - IF the list is nurtured, buys frequently, buys similar offers at similar price points, and the sales page is decent.

That means a minimum of 500 front-end sales. The stick rate on a monthly plan I'd just guess 6 months for now.

I know your numbers, but you can do the math on that to estimate your margins and ROI.

And I'd also expect higher Opt-In Rates if the list met my mentioned criteria.

My question though is what are your current numbers? That should give you some basis to work on.

You don't have to reply - I'll PM you for that.
 

thecalmpickle

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Thanks for doing this!!

What are your opinions on templates? Do you prefer plain text and have you had any experience where a template converts better?

Thanks

I don't like templates at all.

If you're not familiar with Gary Halbert - look up his famous "A Pile, B Pile" talk.

Here:
[video=youtube;8BEpaL1l2PE]https://www.youtube.com/watch?v=8BEpaL1l2PE[/video]

The point?

Even though you may be mailing to potentially hundreds of thousands of people, each email is still being read one person at a time!

Keep it personal, make it look personal, and do everything to get into the A Pile.

Also, I use HTML templates that LOOK PLAIN.

I can't think of any experience where a fancy-looking HTML template converted better. If there's one, my guess is that they didn't email people correctly in the first place.

Curious if you do find one. I'd love to read about it and study why.
 

thecalmpickle

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Thanks for this thecalmpickle - learnt loads already! Would appreciate any feedback on my situation..

We are currently selling 99% on eBay and trying initially to get some repeat business by follow up emails (as we have their name/email address although really shouldn't be using it for this.. but our secret).

Here is my setup for current customers

1) Customer buys something from us - we sent the item out with a nice "thank you" letter (real paper in a envelope) which also contains a candy - finishing the letter it says something along the lines of "Watch out for a email from us it may be of interest to you".
2) One week after the item should have been dispatched I send out my first email - this is a bit "jokey" along the lines of I promised to send you something that interests you but couldnt make up my mind so I sent you a) A discount code off your next sale and b) a joke..I go on to explain how we have more quirky things.
3) 7 days after that I follow up with another email - this time basically saying "i'm intrigued - what did you do with what you bought from us?" with the hope they will respond - then I remind them of the discount. (I couldn't think what else to say)
4) 2 days before the offer is about to expire I send them a email reminding them the offer is about to expire...

Then thats it! my campaign finished...

Now - I myself think this is quite rubbish (and doesn't seem to work), the challenge is (particularly when just starting out) is knowing what copy is going to work? any ideas on a better series would be great!

In terms of how successful - well I must admit I am not using any professional software right now and have written some software which sends out the emails... I don't have great metrics but out of 505 emails sent in last 30 days (for full series) I have had 60 visitors bounce rate of 50% but 0 sales...

So TBH I'm a bit "stuck" I'm sure there are loads and loads of ways to improve this process but i'm a bit out of my depth right now...glad to have at least taken some action though :)

You're saying you're sending customers a stick letter that leads to an email.

In that email, you're sending them to another sales letter with a discount?

And out of 505 sent emails you only get 60 visits? 11.88%

If we're trying to improve your autoresponder, we need to know a couple things.

1. What are they buying? (you can pm if not comfortable sharing)

2. How is the new offer relevant to their purchase?

AND...

3. If you can, can you post a photo or type out what exactly is written on the stick letter?

4. Can also do the same with the email sequence?
 
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thecalmpickle

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Thanks for the feedback, I really appreciate it. I rewrote my email, sent it out to 700 people, and so far a day in I have 14% open rate, 37 unsubs from the mailing list, and 1.3% click through rate (like 10 people). Hope to see an increase in the next few days but we'll see.

I have been deleting the unsubcribers from the list just to make sure I don't email them again. Would you reccomend sending another email to the people that didn't even open the email? I feel like sending an email in the style you reccomended, but just about the benefits of my product

You feel like writing an email next in the style I recommended?

What exactly did you send them in the first place?

Also, a couple other questions:

1. What is the offer? And how relevant is it to the ceramic cutlery?

1.5 How much is the cost of one pre-order?

2. When you say CTR - where exactly are you leading them to?

3. How often do you email your list? And what have you sent them in the past?

4. How was your sent email formatted?
 

Execution=King

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Suggestions for how to approach people to mail for you?

First, thanks for this thread.

My questions: I have a client that sells a certain $200 physical product that I think could do well with a particular narrow demographic in the next few months. (It's kind of a "back to school" item.) I'd like to approach people with email lists catering to this demo, but I don't know how. First, any suggestions on finding people who might have lists like this?

Second, how do you recommend handling the actual interactions with them? I'm assuming you do this with an email, but do you talk money first, or do you just ask for a free mention first? If/when it goes to a discussion of money, how do you handle it? Do you offer a given CPM, and if so, where do you start? If you offer a per-sale commission, any ideas on how much and how should you track it? (The product is an e-comm item; we could probably do a custom coupon or something.)

Also, do you use one approach for what you think are one-man-bands, and another for approaching a larger company?

Thanks again!
 
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thecalmpickle

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I've tried email marketing for my niche and have had 0 response . Some basic advice would be helpful to start . Thx

Why do I get this strange feeling that you're actually the user Mike39, but you've opened a new account just to post in this thread?

It'd be cool to have a MOD check if they're the same person.

About your question...

Some details about your scenario would help.

As in:

1. Roughly how big is your list?
2. What exactly did you send them?
3. How do you know they are proven buyers in the first place?

If you could answer that, that could help me come up with a more detailed answer for you.

For general answers, be sure to read the whole thread. There's bound to be something that'll help.
 

thecalmpickle

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First, thanks for this thread.

My questions: I have a client that sells a certain $200 physical product that I think could do well with a particular narrow demographic in the next few months. (It's kind of a "back to school" item.) I'd like to approach people with email lists catering to this demo, but I don't know how. First, any suggestions on finding people who might have lists like this?

Second, how do you recommend handling the actual interactions with them? I'm assuming you do this with an email, but do you talk money first, or do you just ask for a free mention first? If/when it goes to a discussion of money, how do you handle it? Do you offer a given CPM, and if so, where do you start? If you offer a per-sale commission, any ideas on how much and how should you track it? (The product is an e-comm item; we could probably do a custom coupon or something.)

Also, do you use one approach for what you think are one-man-bands, and another for approaching a larger company?

Thanks again!

I posted some resources to find lists on this post.

Where To Find Lists

Those are some good places to start if you do not want to manually google search for websites in your industry that could possibly have a "advertise with us" section.

If you have an SRDS subscription you can actually see what people have bought, through what medium, how much was it, etc.

Also, I'd look at BUYERS of similar products (despite the demo) because you might find people totally outside your initial target market that you've never even thought of marketing to and might be an awesome match.

Btw, I bumped into this lady before:

Cynthia Tiffany

She's the list broker at homeschoolgiveaways.com

She handles lists for the homeschooling market.

Just a heads up: I was about to rent a list with her for a client, but my client's initial test with other solo ads weren't so great - so I never actually did business with her.

But through our interactions, she seems like a SOLID list broker.

How to handle interactions with List Brokers:

Pricing:

Usually they'll have some media kit or rate card that already discusses their CPM.

CPM = Ad Price / # of subscribers (expressed by thousands)

Example:
Solo ad - $300
Active subscribers - 200,000

CPM = 300/200 = $1.50CPM

No one can tell you exactly what you should be paying.

It varies way too much.

Sometimes smaller publishers have to charge more because using CPM doesn't make sense economically.

Also, sometimes you'll get better returns on one list vs. another.

And asking for a FREE solo ad is a JOKE. They're doing YOU a favor. You're tapping into a relationship they've built.

I wouldn't even ask for a discount unless you've earned it, you're advertising regularly...

OR you NEGOTIATE and give them NUMBERS that can only work for you if they offered you a lower CPM.

(TIP: ALWAYS act like you're not the decision maker. That way you can say, "I'll have to check with my boss to see if these numbers work... He says they can only work if it's lowered X amount... I need a yes or no..." - that sorta deal.)

By the way, usually they do NOT get a commission per sale. Renting a list, solo ads, etc. usually works on a CPM basis not a commission basis like joint ventures.

You'll want to know:
1. How many active subscribers they have?
2. How often they mail out solo ads? (Any more than weekly could be a bad sign)
3. Will it benefit their subscribers?

When you contact them, they'll usually ask you questions to make sure you'll even be a good fit for their list.

1. What lists have your run with so far and what kind of open and CTR's have you received?

2. Would you want us to review your product so we can better promote it?

3. etc...

If they don't ask you questions that try to QUALIFY YOU and YOUR OFFER - I'd run. (i.e. If they say okey-dokey no problem that'll be $x.xx - they probably don't have a good relationship or responsive list)

TIP: Opt-in their list (under a different contact) so you can see how frequent they promote solo ads, how they interact with their list, and to MAKE SURE THEY MAIL YOUR AD.

Size of company:

Usually it's best to work with BIGGER publishers.

They know what they're doing.

One man bands USUALLY have no clue what a solo ad is, has ever rented their list before, and is a headache all around.

If there is one that gets the game, I'd handle the interaction the very same way.
 
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cutefinger

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thecalmpickle, let me say a BIG well done for your AMA. Wow, spent every minute going through each of your response and jotting down tips and ideas.

Many of them I know...some I forgot..until you refreshed my memory. I knew somehow that you must have read ARM by Andre Chaperon to be talking about Cliff Hanger etc.

Read ARM 2.0 myself and used it profitably in the niche market that target my home country(Africa). Let me say thanks for posting.

I would love to get in touch as I have just moved to England and would want to start targetting USA, UK, Europe market. I hope that's ok with you.
 
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cutefinger

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Actually I did NOT know spamming is profitable.


Subject Line Examples:
1. how to make women beg you to take their clothes off
2. the one word that makes you rejection proof
3. types of dates that get you laid
4. how to get women to approach YOU
5. do this to avoid competition
6. what to say to soak her panties
7. where to touch her to make her O
8. how to last for hours even if you're banging a perfect 10
9. how to get good girls to release their inner freak
10. how to never have approach anxiety
11. when to say "i love you"
12. why smiling reduces your chances
13. how to initiate threesomes
14. where to find "marriage material" women
15. proven signs your girlfriend is cheating

By the way, I'm curious - if ANYONE reading this would open ONE of the above emails then hit the like button. I want to track this. If you're embarrassed, don't worry the NSA already knows you're reading this - so hit the "Thanks/Like" button.

WARNING: you may or may not want to tone it down depending on how you position yourself.

Raunchy, but surely that hits the hot buttons of people in that market...

Benefit (know your market) + Curiosity = gets opened


Would you be kind enough to give sample "Subject line" examples if one is targeting the weight loss niche for women niche please...

And...

May i say...been to your website...gosh...i love your sales letter style. Is it thesis?
 

thecalmpickle

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Would you be kind enough to give sample "Subject line" examples if one is targeting the weight loss niche for women niche please...

And...

May i say...been to your website...gosh...i love your sales letter style. Is it thesis?

Sure.

Some general ones...

Subject Line Examples:
1. what to eat to get rid of cellulite
2. how I lost xlbs without exercise
3. guilt-free way of eating junk food
4. how busy moms really lose fat
5. what to do to get rid of face fat
6. how I got rid of arm flab
7. easy exercises for a flat stomach
8. how I made my thighs shrink
9. the daily routine that makes me look younger
10. how my friend went down x dress sizes
11. how I finally got rid of my baby belly
12. which healthy foods actually make you fat
13. how I toned my butt
14. the easiest toning exercises
15. how I finally got the attention of the guy I like

And yes, I'm using Thesis.

Thesis on it's own is really plain though. I'm guessing you just like the way I formatted it.

...which is really plain too. Nothing fancy.
 

cutefinger

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Sure.

Some general ones...

Subject Line Examples:
1. what to eat to get rid of cellulite
2. how I lost xlbs without exercise
3. guilt-free way of eating junk food
4. how busy moms really lose fat
5. what to do to get rid of face fat
6. how I got rid of arm flab
7. easy exercises for a flat stomach
8. how I made my thighs shrink
9. the daily routine that makes me look younger
10. how my friend went down x dress sizes
11. how I finally got rid of my baby belly
12. which healthy foods actually make you fat
13. how I toned my butt
14. the easiest toning exercises
15. how I finally got the attention of the guy I like

And yes, I'm using Thesis.

Thesis on it's own is really plain though. I'm guessing you just like the way I formatted it.

...which is really plain too. Nothing fancy.

Many Many thanks for the above email subject line. I want to make a request to swipe them for my own use if that is ok please.

I think I am going to subscribe to thesis once I find a new niche to participate in and will use it as a framework for my new biz. Still researching niches as its a lot different from what I used to do.

Would you have a systematic way of identifying niches. I know the basic three...but I am talking of.....drilling down etc. In my home country...its easy for me to find niches as I have local advantage, but I have noticed that going international has lots of competitors etc.
 
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Runum

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Why do I get this strange feeling that you're actually the user Mike39, but you've opened a new account just to post in this thread?

It'd be cool to have a MOD check if they're the same person.

Nope not the same person. Execution=King has been signed up for 2 years. Interesting that you would think they are the same though.
 

thecalmpickle

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Many Many thanks for the above email subject line. I want to make a request to swipe them for my own use if that is ok please.

I think I am going to subscribe to thesis once I find a new niche to participate in and will use it as a framework for my new biz. Still researching niches as its a lot different from what I used to do.

Would you have a systematic way of identifying niches. I know the basic three...but I am talking of.....drilling down etc. In my home country...its easy for me to find niches as I have local advantage, but I have noticed that going international has lots of competitors etc.

Feel free to swipe!

Here's what I do when I'm looking for ideas...

How to find profitable niches:
1. Check out Amazon Best Sellers
2. Check out Ezines Categories
3. Check out Popular Forums
4. Check out what's getting funded on KickStarter

If people are spending money or if there's a dedicated section for some niche - usually you can pursue it profitably.

After I pick something I have an affinity for, I first check if there ARE COMPETITORS.

I love seeing a lot of competitors - especially if they are advertising similar products I have in mind!!!

It gives me validation that businesses are making money buying customers and that customers in this niche are buyers.

Then I do a ton of research... knowing what really bothers my target market, how they talk, what they really want, etc.

Then from there I try to sell the "version 1.0" of my idea while appealing to their needs (what I discovered via research) before I actually put start creating and advertising my full vision.
 

thecalmpickle

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Nope not the same person. Execution=King has been signed up for 2 years. Interesting that you would think they are the same though.

I was actually replying to the user HeadHunter not Execution=king.

I just have a feeling that after Mike39 and I's argument, he decided to create a new account and post in here.

Just a weird gut feeling.
 
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Mike39

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Why do I get this strange feeling that you're actually the user Mike39, but you've opened a new account just to post in this thread?

It'd be cool to have a MOD check if they're the same person.

Sorry but your flattering yourself to think that I would take the time to create a new account for something as menial and insignificant to my life as your post; what blog post? :rofl:

I really don't care what you do, I am doing my own thing. Chill out dude.
 

bane

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G'day thecalmpickle!

Thanks again for your help.

I have a consistent SEO source of traffic that I am running to a squeeze and collecting emails.

The traffic KWs are related to: Free iphone 5 or Free ipad

With the US traffic, I am sending them a variety of CPA offers (not overly successfully mind you haha)

However, I am not sure how to monetize the international traffic, as there are not relevant CPA offers for them.

Do you have any suggestions, ideas or tips to help me monetize the International Traffic and/or better optimise my US Traffic?

Also, is it possible to sell this traffic source somehow? I don't really like dealing with it anymore. But it's just going to waste.

List Sizes as of Today:
  • US = 722 & growing
  • Non-US = 836 & growing

Thank you very much thecalmpickle.
 

thecalmpickle

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G'day thecalmpickle!

Thanks again for your help.

I have a consistent SEO source of traffic that I am running to a squeeze and collecting emails.

The traffic KWs are related to: Free iphone 5 or Free ipad

With the US traffic, I am sending them a variety of CPA offers (not overly successfully mind you haha)

However, I am not sure how to monetize the international traffic, as there are not relevant CPA offers for them.

Do you have any suggestions, ideas or tips to help me monetize the International Traffic and/or better optimise my US Traffic?

Also, is it possible to sell this traffic source somehow? I don't really like dealing with it anymore. But it's just going to waste.

List Sizes as of Today:
  • US = 722 & growing
  • Non-US = 836 & growing

Thank you very much thecalmpickle.

Not sure what kind of CPA offers you're offering them...

But it would probably help if they were actually relevant to your KWDs and not just a list of random offers that would benefit you and not them.

If you don't like dealing with it all anymore - then don't.

I've literally just stopped working on a business that has been making me money because I truly didn't have an affinity for it. So I literally just stopped traffic to them and let the business die.

When you have an affinity for a market and their needs, it's much more fun, exciting, and lucrative... since you'll be motivated to keep at it.
 
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PaperCraftinc

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Do you recommended using e-flyer blasts for largr targeted groups to build awareness and sales?

For instance, we have a promotional products line that caters to every industry. We have bought multiple marketing lists, and tailor each flyer with the items that we think would best serve that industry, but have seen very little conversions from it.

What am I doing wrong??
 

thecalmpickle

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Do you recommended using e-flyer blasts for largr targeted groups to build awareness and sales?

For instance, we have a promotional products line that caters to every industry. We have bought multiple marketing lists, and tailor each flyer with the items that we think would best serve that industry, but have seen very little conversions from it.

What am I doing wrong??

From my experience, sending out an e-flyer, catalog, magalog, or any sales message that's selling more than one product will usually result in significantly LOWER sales, especially if this is going out to any other list besides your own nurtured house list.

The reason for that is this...

You're sending a sales message to a brand new lead, with no previous interaction with you, too many different choices to buy from... which usually results in less or no response.

A fix would be this...

Choose the one best seller that you provide to each industry and instead of an e-flyer write a sales letter within the email for that specific product.

Keep the e-flyers, catalogs, magalogs, etc. reserved for your own house list.
 
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Not an expert at this but a great way to get good headlines + get to know some of their language is to look for magazines in your niche. Go to magazines.com and look around. They live off their headlines. If magazines don't catch your attention with those headlines they're out of business. You can be damn sure they researched the hell out of their audience and hired the best copywriter they could find.

That being said. Thank you for this thread!
 

JM35

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owning a gaming company, I get hundreds and hundreds of emails from POTENTIAL CUSTOMERS about things like sponsorships, free giveaways, etc.

So, is there anyway easy way to gather up all the emails that have emailed me on my windows live mail, so i can put together an email list?

Also, our only way of tracking sales is through paypal and the bookkeeping we do (which we dont record email addresses), so is there anyway of easily compiling customer info through paypal? I was am quite disappointed with the the options they have for storing customer info, because they dont have any...

Thanks!
 

FreeMan

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No matter what you do, expect some spam complaints.

But if you open with an apology you could reduce that.

--------------------------------------------
Subject:
sorry...

Body:
I know...

It has been a LONG TIME since I last kept in touch.
And for that I'm sorry.

The reason I haven't been in touch is because
I haven't felt like there was anything noteworthy
to update you about.

But after so many years, I finally have something
I feel is worth mentioning to you.

{then go into how you found a new product, how it'll
help them, and what they have to do now to get it.}

------------------------------------------

Do this and come back with numbers - should make things spicy in this thread.

Finally got around to sending out an affiliate offer.

My lists are pretty small and I just wanted to test it out on a few hundred subscribers to start with.

Here are the results (these aren't final as I sent them out in the last couple of days):

List 1 (Subscribers added between Oct 2007 - Jun 2009)
Sent: 224 messages
Opened: 69 (31%)
Clicked: 41 (18%)
Bounced: 12.1%
Complaints: 0
Sales: 1

List 2 (Subscribers added between Jan 2010 - Dec 2011)
Sent: 105 messages
Opened: 85 (80%)
Clicked: 42 (40%)
Bounced: 6.7%
Complaints: 0
Sales: 4

Speed+ to thecalmpickle for the script as I used it verbatim.

5 sales and no spam complaints so far which is much better than I expected.

I will send it to the rest of the list and report back later with the full results.
 
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biophase

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I have a question on managing lists. In one of my companies, we have the following sales procedure.

Booking Request --> Deposit --> Final Payment --> Trip Completed

The list building begins with an inquiry for a booking request. So I have my list divided by:

1 Quoted not Booked
2 Booked and trip hasn't started yet
3 Booked and trip is completed

I'm using MailCheat(Chimp) to capture the initial booking request. How do I manage the list, do I go into the list and move them manually after the booked into list #2, and then into list #3 after their trip is done?

Do you think I am segregating my list the correct way?
 

thecalmpickle

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Quote Originally Posted by thecalmpickle View Post
No matter what you do, expect some spam complaints.

But if you open with an apology you could reduce that.

--------------------------------------------
Subject:
sorry...

Body:
I know...

It has been a LONG TIME since I last kept in touch.
And for that I'm sorry.

The reason I haven't been in touch is because
I haven't felt like there was anything noteworthy
to update you about.

But after so many years, I finally have something
I feel is worth mentioning to you.

{then go into how you found a new product, how it'll
help them, and what they have to do now to get it.}

------------------------------------------

Do this and come back with numbers - should make things spicy in this thread.
Finally got around to sending out an affiliate offer.

My lists are pretty small and I just wanted to test it out on a few hundred subscribers to start with.

Here are the results (these aren't final as I sent them out in the last couple of days):

List 1 (Subscribers added between Oct 2007 - Jun 2009)
Sent: 224 messages
Opened: 69 (31%)
Clicked: 41 (18%)
Bounced: 12.1%
Complaints: 0
Sales: 1

List 2 (Subscribers added between Jan 2010 - Dec 2011)
Sent: 105 messages
Opened: 85 (80%)
Clicked: 42 (40%)
Bounced: 6.7%
Complaints: 0
Sales: 4

Speed+ to thecalmpickle for the script as I used it verbatim.

5 sales and no spam complaints so far which is much better than I expected.

I will send it to the rest of the list and report back later with the full results.

First, I just wanted to say props on actually just doing it verbatim.

I wish I could take all the credit (especially for the high open rates and no SPAM complaints), but it looks like you also had a good relationship with your list.

Plus, whatever other copy you wrote worked well enough to get some high click throughs.

Would love to see the results after you roll out to your entire list.

Btw, check your PM. I'mma send you my contact info because you seem like a dude that actually takes action.
 
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thecalmpickle

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I have a question on managing lists. In one of my companies, we have the following sales procedure.

Booking Request --> Deposit --> Final Payment --> Trip Completed

The list building begins with an inquiry for a booking request. So I have my list divided by:

1 Quoted not Booked
2 Booked and trip hasn't started yet
3 Booked and trip is completed

I'm using MailCheat(Chimp) to capture the initial booking request. How do I manage the list, do I go into the list and move them manually after the booked into list #2, and then into list #3 after their trip is done?

Do you think I am segregating my list the correct way?

Manually sounds like a pain. I don't use MailCheat(Chimp) that much. But maybe there's an addon that can automatically do that for you.

For instance, if you use AWeber you can invest inAWeber Pro Tools... and that can segment lists automatically based on certain actions.

I think your list segmentation is fine. I like to further segment lists based on price points they've invested. And I'd start a new list based on selling more to the people on the list that have already booked and finished a trip with you.
 

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