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September 27, 2023 • 64 mins

I talk a lot about new technology with my guests, but maybe the most valuable way to connect with your audience isn't new at all. Email has been used and abused to the point that most people, marketers and salesmen included, have given up on investing any real thoughtfulness into their approach. As an industry, we've reduced email to a numbers game.

But email could be so much more! We should be realizing that email is the last remaining opportunity to claim complete ownership of a communications channel, and it's your best shot at collecting and leveraging the purest first-party customer data you're ever gonna to get.

This week I sat down with Yuval Ackerman for what turned out to be a masterclass in ethical email marketing. Yuval is one of the most thoughtful marketers I've met, and she's somebody who's absolutely nailing the human connection in this present age of terrible AI writing and cold emails that nobody asked for. Trust me, you'll want to take notes on this one.

Join Yuval's email list: https://ackermancopywriting.com/subscribe

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Sam Gerdt (00:08):
Welcome everybody to Roadwork Ahead, a podcast that
explores the unmapped future ofbusiness and technology.
My name is Sam Gerdt and I amyour host.
I talk a lot about newtechnology with my guests, but
maybe the most valuable way toconnect with your audience isn't
new at all.
Email has been used and abusedto the point that most people

(00:29):
marketers and salesmenespecially have given up on
investing any realthoughtfulness into their
approach.
As an industry, we've reducedit to a numbers game, but email
could be so much more.
We should be realizing thatit's the last remaining
opportunity to claim completeownership of a communications
channel, and it's your best shotat collecting and leveraging

(00:50):
the purest customer data you areever going to get.
This week, I sat down with YuvalAckerman for what turned out to
be a masterclass in ethicalemail marketing.
Yuval is one of the mostthoughtful marketers I've ever
met and she's somebody who'sabsolutely nailing the human
connection in this present ageof terrible AI writing and cold

(01:11):
emails that nobody asked for.
Trust me, you'll want to takenotes for this one.
I think the first question Iwant to ask is why is email so
many years after it came alongand kind of blew everybody away?
You know we're close to 30years in now with email.

(01:31):
Why is email still such avaluable channel?
Why is it worth investing in?

Yuval Ackerman (01:38):
Sure, what a wonderful question.
Let me just correct you tobegin with.
We're talking about 50 years ofemail.
Okay, 50 years 50-ish since thefirst email was sent.
Why is it so powerful?
Why people need to give it morecredit.

(01:58):
First of all, let's go back tothe basics.
Email is an electronical mail.
Now, I don't know about you,Sam.
Back when I used to live in onepermanent place, I used to love
opening my postbox every dayand see if I have letters inside
, regardless of what lettersthose were and we're talking

(02:21):
about bills, right but I wasvery excited to see my name on
letters, because there'ssomething about this feeling of
this direct communication thatno other channel that I've seen
so far can replicate.
So, first of all, it's thisreally direct connection, human

(02:43):
connection.
Second of all, all of theresearch in the world in the
past couple of years has shownthat email is actually the most
profitable marketing channel outthere.
We're talking about, on average, a return on investment of
something between $38 to $44 forevery dollar spent.

(03:08):
So that's powerful.
And, last but not least, let'snot forget that an email list
that you have, that you nurture,that you grow, is yours.
No algorithm, no social mediaplatform, no billionaire can
take it away from you in a blinkof an eye.

(03:30):
It's something that you own.
It's something that peopleopted in, hopefully with their
consent, and this is so powerful, and people who don't
understand that this is unbiased, obviously, but the most
important marketing channel thatthey own, need to start

(03:51):
seriously thinking of how dothey get to the point that they
have one and they have a listthat they can rely on.

Sam Gerdt (04:00):
It's such an interesting point.
I feel like we don't fullyrealize what ownership of data
really of access, ownership ofaccess means.
Maybe we go into that a littlebit more.
Why is ownership so important?
What's happening with otherchannels that would make someone

(04:23):
owning their email channel sucha valuable thing?

Yuval Ackerman (04:28):
That's such a great question.
So let me use an example thathappened to me a few months back
.
I'm using for my own marketing.
I'm using LinkedIn as my mainchannel, aside from my email
list, obviously, and I have acouple of thousands of followers
over there.
I don't have as many people onmy email list, because email

(04:50):
lists are something that notmany people like to be on, and
that's completely fine.
But then one day I went to thisnetworking event and I connected
with a lot of new people andsomething in the back end of
LinkedIn raised an alarm andthey told me basically, you're

(05:14):
using a bot or a third party,something to connect with all of
those people.
Therefore, we're blocking you.
And then, in a split of asecond, I could not access my
network, my connections, mycommunity, and that is something
that, luckily, I have my ownemail list, so if I had to rely

(05:38):
only on my email list, I couldhave, but still, linkedin is not
mine, and who knows what'shappening in the background and
it's not something that you cancontrol.
And who knows?
That was my first strike, so tospeak, but if it was my second
or my third, who knows, maybe Iwould have never gotten it back.

Sam Gerdt (06:00):
Censorship is something that we think a lot
about, as it relates to critiqueof government or even the
spread of false information.
We see this more and more,where censorship has become a
divisive topic, but censorshipis not the only thing that we're
talking about here.
We're talking about simplemistakes.

(06:23):
A simple mistake can cost youaccess to an entire audience.
Obviously, there's degrees, soit's not just simple mistakes.
There's all kinds of things inbetween a simple
misunderstanding and a realreason for censorship.
The point I think that you'remaking, though, is you have
somebody who is not you, whodoesn't know you, who has their

(06:46):
own agenda, who has absolutecontrol, to turn your voice off
with the flip of a switch, and,admittedly, oftentimes they're
not even aware that they'redoing it.
It's completely automated, orit's behind the scene, or even a
third party is handling it forthem.
So there you have another levelof ambiguity who is actually in

(07:07):
control of your channel?

Yuval Ackerman (07:11):
And more so, figure out how to restore
everything, because all of thosebig social media platforms,
they don't really care aboutyour profile, even if you're
paying a lot of money for ads.
Sometimes I mean go fish.

Sam Gerdt (07:28):
That's absolutely right.
It puts email in a stunninglynew light.
If you take a minute just torest and think about it, right
there You're like OK, what do Iactually own when I have this
big following on social media?
What do I own?
People say, well, you own yourchannel, but if your channel can
be turned off for any reason,then do you actually own it?

(07:52):
Let's redefine what ownershipactually is.
How about data privacy?
How does that play into this?
I know that this has become amuch more hot button issue,
especially in Europe, where youare with GDPR, but how does data
privacy make owning yourchannel that much more valuable?

Yuval Ackerman (08:12):
I mean, when you own the data, you can connect
with and to your audiencedirectly, and you don't have to
rely on algorithms, you don'thave to rely on ads.
You own the data that you wishto collect, and that's another
point that is important for meto put out there.

(08:33):
I think that a lot of bigbrands out there miss out on so
many opportunities.
Even those who have huge emaillists and a lot of supposed data
, they're not necessarilycollecting the right data or the
data that would serve both themand their subscribers, and so I

(08:54):
think that, especially withemail marketing, we have an
opportunity here.
It's a huge opportunity tocollect data that is going to
serve, as I said, both the brandwho's sending those emails and
the recipient as well.
So, whichever data you'recollecting, you don't have to
rely on cookies as well, by theway, which is something that, as

(09:18):
we know, in a few months' time,will not be a part of our world
anymore, supposedly.
And, yeah, the more data you'regathering as you go, the more
first party and zero-party datathat you're collecting, the
better you can serve youraudience and the individuals in

(09:39):
your audience, as well as yourbrand.

Sam Gerdt (09:43):
It's interesting with the influx of all of these
things and there's a convergence, I think, on this one issue.
You have regulation, with GDPR.
You have AI and its ability totake data collection and move it
to a completely new and veryscary level.

(10:04):
You have cybersecurity concerns, and all of that has led us to
recognize that maybe collectingfreely all of this third-party
data and having complete accessto it is a bad thing, which then
leads to us saying, no, we'regoing to get rid of all that.

(10:24):
So there's been this walk back,and you see it with Google.
You saw it with GoogleAnalytics earlier in the year
when they forced the new version.
They're doing the same withcookies, like you mentioned.
They're walking back theability for people to collect
this third-party data,especially without consent, and
that's where the regulationcomes in.

(10:44):
I think GDPR was very clear onthat, and so, with all of that,
email then becomes that muchmore valuable because you have
first, like you're saying, firstparty or even zero-party access
to the valuable data thatyou're using then to do
marketing and sales.

Yuval Ackerman (11:04):
Yeah, correct, and it's a huge question here to
ask of which data are youcollecting and how, so it both
complies with the rules that arehere in Europe, for example,
how do we also use those rulesor those limitations, so to
speak, to actually benefit fromthe kind of connection that we

(11:27):
want to nurture with ouraudience?

Sam Gerdt (11:31):
What was the perspective in Europe when GDPR
was coming around, when thisregulation was being developed
and then when it finally passedand then when it was rolled out?
What was the Europeanperspective on that?
Is that something that I thinkwas different here in America?

Yuval Ackerman (11:51):
I could not tell you myself because I wasn't
there in the field when ithappened.
I can only assume that peoplewere delighted that their
privacy is being kept by therules and by laws and that
someone is taking care of themand of their privacy.

Sam Gerdt (12:11):
That's the overwhelming sentiment now, then
, is that GDPR is a good thing.

Yuval Ackerman (12:16):
Generally, yes, I mean don't get me wrong there
are a lot of brands here inEurope that are struggling with
this, A lot of brands in the UKwho are now very confused by
GDPR.
No GDPR, what are we doing?
What are we following?
But, generally speaking, assomeone who has only worked
under GDPR, I think it's amarvelous thing If you know what

(12:41):
to do with it.

Sam Gerdt (12:42):
Yeah, I think it's a mixed bag here, but I think
generally we've seen nothing butgood come out of it, especially
from the consumer perspective.
I think in time, once we seemore of the advanced data
analytics that say AI canprovide, we're going to realize
that having that vast amount ofthird-party data is actually

(13:07):
counterproductive.
I think what I mean by that isthe consumers will rebel against
it.
By using it, you'll only beable to be accused of
manipulation, of spying, of allof these negative things.
I do think and I believe you'llagree wholeheartedly with me on

(13:30):
this, I do think that when abrand takes the time to build a
trust relationship and collectdata firsthand, that data,
number one, it's way moreactionable.
And, number two, it's apositive reaction from the
consumer when it's used, ratherthan a negative reaction.

Yuval Ackerman (13:53):
Absolutely.
It is a win-win situation Again, if you know what you're doing
and if you're taking the timeand the resources to invest in
strategic thinking of datacollection and email marketing
as a whole.

Sam Gerdt (14:08):
It reminds me of when your spouse says they drop
hints over and over again whatthey want for a birthday or for
whatever, and you listen and areattentive and you deliver and
there's that satisfaction there,versus when maybe you go in and
you read their diary or theirjournal and you say I found it,

(14:29):
and then you go by.
Obviously, one's going to get apositive reaction and one's
going to get a very negativereaction.
I feel like that's whatcompanies need to see.
We're scaling up to that degree.
It's like do you want to readtheir diary or do you want them
to drop hints?
And you pick up on it and getthat rewarding experience.
Is email the best way, then, toget that first party and that

(14:53):
zero-party data, or are thereother channels where this works
really well too?

Yuval Ackerman (14:58):
It depends in your overall marketing mix.
I know of a company thatcollects a lot of really useful
first party and zero-party data.
They're collecting that data onsite, so you do need to have
some kind of a very advanced yetsimple quiz slash pop-up.

(15:19):
They collect all of this dataand then they're referring to
segments created in emailmarketing.
Can different brands havesuccess in other channels other
than email marketing?
Absolutely.
However, if you do want to stepinto this room and make the

(15:43):
best use out of it, I believeand also the research has shown
that you can turn it to be themost profitable marketing
channel out there and the mostcommunity and audience nurturing
there is out there, Becauseeverything basically stamps from

(16:04):
email and then goes todifferent or other platforms
like Facebook communities orSlack channels.

Sam Gerdt (16:13):
So then, if email is the most valuable way of getting
this, we have to talk aboutbuilding audiences and how you
accomplish that, Becausebuilding an email audience, in
my opinion I've been inmarketing for 15 years is one of
the biggest challenges comparedto audience building anywhere
else.
If you're attempting to build alist of really engaged and

(16:39):
valuable contacts, how are youconvincing them to opt in?
What's happening before they'rea part of your list?

Yuval Ackerman (16:49):
So you either need to tap into what we call,
in copywriting, pain points,which is not something that I'm
a huge fan of, but it's workingif you know what you're doing
and you're not doing this tooaggressively and you're
basically solving a problem, oryou're promising to solve a
problem.
That's one way.
The second way has to do withsome kind of exclusivity or some

(17:14):
kind of entering a community.
If that's something that yoursubscribers, your ideal
subscribers, are interested in.
Basically, it all boils down towhat interests them right now
and what's in it for them togive you their precious email
address.
Let's face it basically youremail address is basically the

(17:37):
last sacred space or property inthe internet that is ours,
fully ours.
So it needs to be worth it forwhoever is seeing your pop-up or
your signup form to want tojoin.

Sam Gerdt (17:56):
So if the email marketer, then, is taking that
perspective which they should,that their target's email
address is precious, that it isspecial, how are you treating
the person behind the emailaddress in order to communicate
that in all of that pre-optencontent?

Yuval Ackerman (18:16):
Well, you basically treat them as people,
not as walking wallets, and youmarket to them as you would like
to be marketed to with dignity,with respect, and you basically
treat it as if you're datingsomeone.
The last thing you would wantto get when you're dating

(18:38):
someone is to meet someone andall of a sudden they're just
forcing themselves on you withokay, let's jump into bed and
buy my things.
That's not working anymore.
If that's not what yoursubscribers want, when most of
them don't want that, then it'snot going to work.
So you treat them with respectand you build this connection

(19:00):
first and you tend to theirneeds and you show them what
you're capable of with yoursolution and you start from
there.

Sam Gerdt (19:10):
That's an interesting analogy, because my next
question was going to be howdoes that relationship change
once they have opted in, or doesit change?

Yuval Ackerman (19:19):
It does change because, again, there's this
best practice, so to speak,especially with e-commerce,
which is one of the mainaudiences that I'm working with,
or the main brands that I'mworking with that you have to
push your product as soon aspossible and get the product
into your subscribers' hands sothey can make up their minds and

(19:42):
see whether or not theycontinue with you.
Yet again, most people see yourwelcome sequence and all you're
saying there is how we foundedour startup or how our story
began, and here's 10% off andhere's free shipping, when, in

(20:03):
fact, that's not what most ofyour subscribers want from you.
They want to hear what's in itfor them.
Yet again, how can you solvetheir problems and how can they
connect with you as a brand andthe people behind the brand Not
jumping into bed two minutesafter they subscribed?

Sam Gerdt (20:25):
You're promoting, then pushing I shouldn't say
pushing creating an intermediaryspace where you're engaging
with new opt-ins before theselling process.
Most companies don't have a lotof… content there and they

(20:46):
don't have a lot of eyes there.
They're not necessarily lookingat that intermediary space.
So how do you, in your own roleas an email marketer, how do
you encourage clients to investin that space from opt-in in,
between opt-in and selling?

Yuval Ackerman (21:04):
Right.
So I usually talk about thewelcome experience as a whole as
something that every brand onearth needs to take care of, and
that includes the opt-in.
That includes the thank youpage or the success message and
the welcome sequence.
Now, usually, in most cases, Ido see that pretty much and I'm
generalizing pretty much everybrand out there is lacking

(21:29):
something in one of those stagesor more.
So, when it comes to the opt-inprocess, you definitely do want
to collect data first, and zeroparty data from your new
subscribers.
You want to ask them what is itthat they are interested in?
And if you cannot do that, thenI would highly recommend going

(21:53):
and talking with your existingsubscribers, your most and
engaged subscribers, andbasically asking them what would
make you re-subscribe to ourbrand's newsletter?
What would be a good enoughexchange for you to go ahead and
re-subscribe?
So that's one.

(22:14):
The success message needs towrite away or refer to the inbox
.
Now, if we're going back to thetrust issue, a lot of brands out
there are telling you, as a newsubscriber if you've seen or if
my emails have blended in thePromotions tab, go ahead and

(22:36):
drag them into the Primary tab,which is a huge mistake, in my
opinion, for a couple of reasons.
First of all, you haven'tearned their trust to be in the
Primary tab.
Second of all, the Promotionstab is where they expect you to
land.
You are sending promotionalemails, after all.

(22:56):
And then there's the WelcomeExperience, which, as I
mentioned before, is usually avery quick hey, buy my stuff
right now or forever, hold yourpeace and that's all.
The fake.
Scarcity and urgency issomething that I can talk about
forever, but it's very, veryunnecessary in today's age.

Sam Gerdt (23:18):
It sounds like, then, what you're doing on the back
end is a lot of segmentation,paying attention to engagement
on an individual level even, andthen pulling multiple lists,
multiple segments.
Is that something that you'redoing on every email list, or is
it something that you're onlydoing when you reach a certain

(23:40):
point in terms of numbers?

Yuval Ackerman (23:42):
It's something that you need to do as soon as
you possibly can, of course,within reason.
I mean, I wouldn't segment youraudience right from the get-go
into 10 different segments or 20different segments.
That's not something that youcan manage, that, obviously.
But it also depends on yourresources and your manpower, et
cetera.
I like sticking to very basicsegmentations.

(24:07):
Depends on the brand, dependson the audience, and that's
something that I definitelyrecommend anyone who can to
start investing in from prettymuch day zero.

Sam Gerdt (24:19):
Do you like automation for this process, or
do you prefer to do it yourself?

Yuval Ackerman (24:23):
then oh, those are a must.
I don't have the time to sitand segment my clients,
subscribers.
I mean, it's just not possible.

Sam Gerdt (24:33):
I was just curious because you take such a personal
approach to all of it.
I was just curious ifautomation played a part in it.
I think along those same linesyou could ask the same thing
about third-party data.
Do you use third-party datawhen you're making those
decisions, or do you insist ononly first and zero party?

Yuval Ackerman (24:53):
I insist on zero and first party just because of
two reasons.
First of all, consent is huge.
It's a huge part of what I doand it's a huge part of why my
clients work with me.
And, second of all, there's nopoint in investing in let's call
it technology that it is notgoing to be available or isn't
going to be out there in just acouple of months.

(25:14):
What's the point in that?
Let alone the fact that it'snot accurate in some of the
cases.

Sam Gerdt (25:21):
Let's say that you have a list of 100 subscribers
in a particular segment.
You're not looking at yourengagements with those people
outside of email to determinewhat you do with them inside of
email, or are you?

Yuval Ackerman (25:37):
Well, everything is connected.
So ideally, even those 100subscribers need to be I'm going
to use a word that I'm notreally liking but they need to
be tracked, and obviouslyeverything is connected,
especially with e-commerce, bythe way.
I mean, you cannot have astandalone subscriber who

(26:00):
clicked on a bunch of links inyour email and then stayed on
your website and then you're notsending them an abandoned card
or browse email.
I mean, that's just ridiculous,right?
So obviously within reason, butpeople and subscribers need to.
We need to see what they'redoing across different channels,

(26:22):
because everything is connected.

Sam Gerdt (26:24):
It sounds like the basis of what you're saying is,
when you start treating peoplelike people and respecting their
privacy, their boundaries,there's still an expectation
that you're going to use thetools that we have, like
tracking, like automation, tomake our ability to reach so

(26:45):
many people that much easier andmore effective.
But what we're not doing iscrossing that line into using
the tools in a way that theconsumer maybe doesn't
understand or in a way thatthey're not aware of.

Yuval Ackerman (26:59):
Or in a way that they don't consent to.
Definitely I cannot tell youhow many times I've seen my
email address being spreadacross different lists even
though I never opted in, or Iopted into lists where I was in

(27:19):
one location and then, becauseit was third party cookies,
whoever is managing this listjust determined that this is my
location.
So then you're also getting avery, very not accurate
personalized experience whichmakes you, as the recipient,
think what happened there?

(27:40):
What happened there?
I mean, I don't live in Lisbon.
Why do you have it in yoursystem?
So it creates a very genericexperience, which is the last
thing that we want to let oursubscribers feel.

Sam Gerdt (28:00):
I think this is an area where marketers who deal
less with GDPR are probablydeficient, and that is the
granular level at which opt-inis expected or necessary in
order to be above board, butalso in order to be effective.
We tend to think that, for aparticular business, if we get

(28:27):
an email from somebody, then,within the purview of that
business, we can use that emailhowever we see fit.
And not only is that not true,at least by this GDPR standard,
which is a European standard,not necessarily an American
standard not only is that nottrue, but it's also not helpful,
because what you're doing isyou're risking frustrating the

(28:52):
end user, the consumer, ratherthan actually meeting their need
, which, presumably, if you'vebuilt trust up to the point that
they gave you their email,you're really betraying trust.

Yuval Ackerman (29:04):
Oh yeah, absolutely, and it's not
something that I'm only seeinghappening in Europe.
I'm already seeing more andmore people all over the world
just posting things you know allacross social media just saying
you know, you really, reallymessed up this first impression
because all I wanted to do is tohave, let's say, we're talking

(29:25):
about small businesses here, butall I wanted to do is to have a
demo with you or a coffee chatwith you, and I never consented
that you would add me to yourlist.
You never asked me for myconsent, and so it's very, very
hard to correct such a bad firstimpression, and that's what I
want each and every one of ourlisteners to remember.

Sam Gerdt (29:48):
So a very common workflow that we see often is
someone will create a piece ofcontent that's valuable, and
then they'll put up ads for thatpiece of content.
They'll list it in email inorder to get that piece of
content.
All fine and good.
What happens next, though, isthey take that email or that
phone number, or whatever it was, and they immediately reach out

(30:09):
for a sales call for theirplatform or their product.
That's not necessarily superrelated to the piece of content,
and what this does is itcreates a little bit of
confusion and a little bit offrustration, because, first of
all, it should be apparent If Igave you my email address to get
this piece of content, I wantedthat piece of content.

(30:31):
I didn't necessarily wantsomething else, and secondly,
like you're saying, you didn'task for permission to give me
the sales spiel.
You asked for permission forthis other offer, and I think
that's the granular part that wemiss out on here, and I think

(30:54):
it is uniquely something thatbelongs to marketers that aren't
necessarily paying closeattention to things like GDPR.
That actually happened to me theother day.
I saw an e-book that I reallywanted to read, and it had to do
with agency operations, andnext thing.
I knew I was getting a coldcall on a platform that wasn't

(31:16):
related to agency operations andI was confused how that
happened.
But it was, because of thatfirst interaction, Something to
be aware of absolutely Once youhave that audience.
There's so much email goingback and forth.
It's like you talked about atthe beginning that mailbox and
you want something with yourname on it.

(31:38):
Is there ever a point where youwalk out to the mailbox and
it's absolutely stuffed likeit's overflowing, and you open
it up and it's a disappointmentbecause it's all junk, it's all
nonsense.
Does that ruin the experience?
Is there a sense in whichyou're just never going to cut

(31:59):
through the noise of someonewhose inbox is essentially
ruined by that?

Yuval Ackerman (32:05):
Yeah, absolutely , and I'm hearing about so many
people who have thousands ofunread emails or inboxes that
they just opened for suchpromotions because they knew
that they're going to bebombarded with such emails.
And that's one of the mainchallenges that I think

(32:25):
e-commerce brands and sometimesother B2B brands just don't
realize what's happening on theother side, or how is it the
emails are being perceived, orthe cadence.
There are no quick fixes tothat, I do have to admit, but I
would definitely invest in agood welcome experience.

(32:48):
A good welcome experience meansthat your subscriber is going
to remember your name, yoursender's name, and they are
going to automatically link yourvalue with your sender's name.
So then it doesn't matter whichsubject line you're sending
your email with.
They're always going to open,or they're mostly going to open

(33:11):
most of your emails.
So that's one thing, but anotherthing which I really love
talking about is giving yoursubscribers the autonomy and the
power of choice to decide howmany emails they want to receive
, and for that you do have tohave a little workaround.
But I definitely recommend anybrand out there to have a more

(33:35):
than basic preferences centerwhere your subscriber can just
go and say listen, I just wantto get one email from you every
month.
I want to receive two emailsfrom you a week, but given
people really the power tochoose their own experience and
to play around with it.
Because, at the end of the day,if we're playing around with

(33:57):
that experience and if we'regiven that power of choice,
we're going to remember thatbrand that allowed us to do so
much, much better.

Sam Gerdt (34:09):
There's so much bad email out there and it just
keeps coming there.
Just doesn't seem to be an endto it.
It doesn't sound like manypeople are believing what you're
talking about.
It sounds like that email isjust something that they do.
Is that your perception?
Or people just believingsomething differently than what

(34:32):
you believe?
Why is there so much bad email?

Yuval Ackerman (34:36):
There's so much bad email because a lot of
marketers have abused thischannel for way, for far too
long, and I think that peoplewho believe that email is just
not the way to go were onlyexposed to that kind of bad
marketing and bad marketers whohave forgotten what it is like

(34:57):
to build and nurture arelationship with another human
being through a screen.
And so I mean it was also hardfor me initially to reconcile
this oh, I want to do emailmarketing, but email marketing
is also so sleazy and so icky.
So how do I find a healthymiddle?
And there is a way to do emailmarketing in a positive, helpful

(35:23):
, useful way.
It's just a matter of how, andI find that a lot of companies
and brands that just choose tostick to the best practices
without actually asking theiraudiences is that what you want?
Those are the brands who abuseemail marketing and really use

(35:44):
it as a channel.
I mean, they might as well juststop emailing all together,
even though it works for someaudiences.
Right, all of those so-calledbest practices.
But I do believe that there isa way to do email marketing in a
way that is useful, in a waythat is human.
It's just a matter of wantingto go one step beyond and

(36:06):
choosing the hard work, becauseit is hard work to really get to
know your audience and cater totheir needs and desires.
It is hard work.
You cannot choose shortcutsjust because your competitor has
chosen the 10% off your firstpurchase and it worked for them,

(36:27):
so it might as well just workfor us.
It doesn't work this way.

Sam Gerdt (36:30):
Can you give me some examples of some of the best
practices that you avoid?

Yuval Ackerman (36:35):
Best practices that I would avoid are any kinds
of best practices that havebeen used again by your
competitors with similaraudience to yours and you're
just copying and pasting it.
So that's one.
Any kind of fake scarcity andfake urgency is a big no-no,

(36:55):
because people can see rightthrough it very, very instantly.
Anything that has to do withlying just straight out, lying
to your subscribers or notappreciating their humanness and
their being a part of yourprocess and your journey,

(37:16):
because, honestly, without yoursubscribers, who are your
customers, you don't have anyjustification to keep your doors
open as a brand.
So those are the best practices, in a nutshell, that I would
avoid at all costs.

Sam Gerdt (37:36):
We have more and more , I see this companies,
especially email serviceproviders, offering tools, ai
tools, often to help craftthings like the subject line, to
modify or edit the copy, eventemplating.
Generally, is this somethingthat you're wary of or is it

(37:59):
something that you're hopefulfor?

Yuval Ackerman (38:01):
Both, actually, because I think that AI is
really going to help us a lotwith plenty of things.
Would I rely on it as is andjust send something that AI
generated without doublechecking it?
Absolutely not, not at thispoint in time when we're
recording this.
I've seen a lot of bad copywritten by AI, and I mean lots

(38:26):
of it, not only in emailmarketing, but just spread
around and across the net, andif people think that it's not
apparent, then they're lying tothemselves mostly.

Sam Gerdt (38:42):
So what do you think then AI is gonna be able to do
well?

Yuval Ackerman (38:45):
AI, at least in email marketing, is going to
really help with building reallywell-crafted automations that
cater to different needs ofdifferent segments or different
subscribers.
That is something that I'm veryhopeful for, because I would
love to get to the point whereI'm just going into whichever

(39:09):
email service provider and justtype create the segment, does
this and that and this and thatpoint and create that segment,
then tag anyone who clicks onthose links, ta-da-da, and then
it just happens and I don't haveto drag and drop.
Now some of the ESPs out thereare working on similar things

(39:30):
with various levels and rangesof success.
It's not something that Ipersonally have seen executed
perfectly, but it's gettingthere.

Sam Gerdt (39:44):
Would you consider then using let's say, you've got
AI doing pattern recognition inyour interactions with
subscribers and in the processof pattern recognition it
generates insights into youraudience.
Would you consider using thoseinsights third party or would

(40:08):
you be willing to use them andconsider them first party, if
it's not necessarily a humanthat's picking up on a pattern?

Yuval Ackerman (40:16):
Well, I see those as first party, because
people have interacted with ouremails or with our website and
then AI that is just embeddedonto our emails or backhand or
whatever gathers the conclusions.
I don't see it as third partywhatsoever and I'm actually very

(40:39):
thrilled to see such toolsbeing used more and more in the
future if they serve theaudience in the right way.

Sam Gerdt (40:49):
And that goes back to to maintaining good trust
relationship with the people onyour list, because I think one
of the things that we saw wherethere was this backlash was
pattern recognition was used inhuman behavior before.
The difference was well, Iwasn't interacting with you, you
were just watching me.
So in this case, because youhave a trust relationship with a

(41:13):
specific audience, because youhave ownership of that list, the
sense of ability to dosomething and the ability to say
, use those tools to study andlearn about your audience, it
becomes appropriate.

Yuval Ackerman (41:31):
And I also want to mention that you know we're
talking about trust as if it's adestination that we're just
getting to.
Trust is never a destination.
It's a journey.
Even if you got someone's trustalong the way, it doesn't mean
that they will necessarily trustyou in a weeks time or in a
months time.
It's something that you have tokeep on nurturing and building

(41:54):
and reiterating.
It's not a one and done thing.

Sam Gerdt (41:58):
Yeah, I agree.
I think we've seen this.
I think anybody who works in anagency setting or ongoing
relationship with a client knowsthis firsthand.
Even when we are dealing withour client, not necessarily
marketing to their audiences theimportance of maintaining and
building trust, we like to, wecan be guilty of putting the

(42:25):
majority of the value in theserelationships on the front end
and then being surprised when, afew years down the road, things
start to go poorly and it'sbecause, well, you haven't been
maintaining, you haven't beenbuilding and adding to that
trust relationship.

Yuval Ackerman (42:42):
Yeah, I think that a lot of marketers out
there, regardless of emailmarketing, they forget that
we're marketing to people andhuman psychology.
As complex as it is, it's alsopretty simple as soon as you
know what it is that you'redealing with and how people form

(43:03):
relationships in the real world.
That's exactly what you need toreplicate in the online space
and I get that a lot of peopleand a lot of marketers, myself
included it's very human.
We want to have shortcuts, wewant to have quick wins, but
eventually we cannot reach thosequick wins with everyone

(43:25):
straight off the bat.
It doesn't work like this.
There are humans on the otherside and, as you mentioned the
cold calling a few minutes ago,it's just basically going from
first base to third base in twoseconds.
It doesn't work like this.

Sam Gerdt (43:43):
Before we leave it, I want to go back to the AI
augmented email marketing andjust ask what about testing?
Is AI for A-B testing somethingthat can be incredibly valuable
, or is it still kind of inprogress?

Yuval Ackerman (44:00):
It's always in progress and it is going to be
very, very valuable.
Any kind of testing that youcan allow yourself to do, with
or without AI, is going to beincredibly valuable for your
brand and for your audience.
So, as long as that kind oftesting is something that's even
worth testing and noteverything is worth testing all

(44:22):
the time, but if it is worthtesting at that particular point
in time, do it absolutely.

Sam Gerdt (44:29):
What do you find yourself testing most often?

Yuval Ackerman (44:33):
I test mostly subject lines, sender names, all
kinds of conditional contentdepending on who's receiving the
email, yeah, and all kinds ofdifferent parts of the emails
that could be personalized.

Sam Gerdt (44:53):
Is personalization something that you've seen get
more and more valuable over time, or was it always just
absolutely valuable?

Yuval Ackerman (45:01):
It's always absolutely valuable.
Yet again, it depends howyou're doing that, because
saying or mentioning someone'sfirst name seven times in 300
word email definitely soundslike you're stepping into a car
dealership.
With all due respect to cardealership people, it just

(45:25):
doesn't sound right.
So personalization, again, whendone right, it's extremely
valuable.

Sam Gerdt (45:33):
Can you give me some examples of personalization done
right?
That might be a little bit moreadvanced than, say, just
opening with the person's firstname.

Yuval Ackerman (45:42):
Sure, I have seen emails that contain my name
in photos.
So basically they use thepersonalization in photos.
But personalization doesn'thave to be necessarily with the
first name, as you mentioned.
It can also definitely be inthe type of sequence that you're

(46:03):
entering or the kind of cadencethat you're getting your emails
through.
Personalization really is awhole world of possibilities.
It's really a matter ofsometimes it sounds a little
silly, but just sitting downwith a bunch of your subscribers

(46:23):
and asking them okay, so youpurchased this thing for me.
What do you want to get from menext, aside from their seat for
buying whatever it is, whatwould be useful for you to get
from me?
Is it how to use it, or is itsomething?
Or do you want to get it maybejust a little bit further down

(46:45):
the line?
When would you actually like torecommend me to someone else?
It could be personalization,also in terms of segmentation.
So let's say you have asubscriber that bought something
and they want to return it, andthere's a ticket open in the

(47:05):
customer service department, andwhat that same subscriber would
continue getting is get yoursecond purchase, get your second
purchase, get your secondpurchase, which makes absolutely
no sense.
And this is exactly for goingback to when we said that
everything is connected.
Everything needs to beconnected, because if you have a

(47:27):
subscriber that wants to returnsomething and you keep sending
them emails that are irrelevantto where they are in their
customer journey, you've lostthe battle right there.
And then.

Sam Gerdt (47:38):
And this is truly an opportunity, because I feel like
most people have given up onthe idea that somebody's gonna
do email this.
Well, so for me, in yourexample, if I had made a
purchase and was dissatisfiedand going through other channels
to have that corrected, and Icontinued to get email from the

(48:00):
company encouraging a secondpurchase, I would not be
surprised.
I would not feel like, oh, Ican't believe they're doing this
.
It would just be par for thecourse for email.
I would say, oh, of coursethey're gonna do this.
You know they're just sendingme these emails blindly.
The opportunity, then, whatyou're saying, is if you can

(48:20):
come in and disrupt thatexpectation and actually show a
level of personalization that'saware, and not even in a creepy
way, but just in a common senseway, where you're saying, hey, I
know you had this problem,let's hold off on future
promotions and let's talk abouthow do we build trust back.
And it shifts you into thisother workflow where the email

(48:43):
tone is completely different.
People don't realize how doablethat is, but nobody does it.

Yuval Ackerman (48:49):
Yeah, very few actually do yeah.

Sam Gerdt (48:53):
Yeah, that's such a good example.
So, apart from personalization,then, and this kind of
segmentation, automation thatwe've been talking about, let's
look at the email itself, and Iwanna ask what are the elements
on the page that you find to bemost effective when you're

(49:13):
reaching people like this?

Yuval Ackerman (49:15):
Hmm, that's interesting because that really
depends on the brand and thetiming and so many different
factors.

Sam Gerdt (49:21):
Yeah, of course yeah.

Yuval Ackerman (49:24):
There's something that more and more
brands do success moresuccessfully or not but a lot
more brands are going back toplain text with one call to
action.
No fancy buttons or fancyimages, just a very
straightforward kind of an emailof hey, we're having a sale,

(49:46):
thought you might be interestedin checking it out, click here
to also get 20% off from us, forexample.
And those are very, verypowerful when done right,
because those feel very personal.
It almost feels like a friendwrote that email to you.
Obviously, most e-commercebrands don't really collect the

(50:11):
first name, because why bother,right?
So you don't necessarily getthat type of or that level of
personalization, but you know,so it really depends it could be
plain text.
One thing that is really reallypowerful, as always, is the
rule of one of one topic, onereader, one call to action.

(50:34):
Keeping it simple, really.
Yeah what else could be reallyreally powerful in email formats
?
That's an interesting question,because it's something that you
can also Inside one brand.
You can change it all the timeand it would still be successful
, because you are growingAlongside your audience and your

(50:56):
community and maybe somethingthat you're thinking about Is
something that your audiencedoesn't want, or vice versa.
I can give the example ofHubSpot.
They used to have a verysuccessful Newsletters for a
newsletter Format for four yearsand recently they changed it to
something a little bitdifferent.

(51:16):
Obviously, I don't know theirsuccess rate with this one, but
I'm really enjoying the new andimproved Format and I think it's
it's a part of growing a brandand developing as a brand.

Sam Gerdt (51:31):
It's interesting that you say that.
I've had a discussion recentlyactually in house here and the
question that I was working on adesign theory.
I like to do this.
The question, though, was let'slet's say that you have three
different emails.
You have one email that isspectacularly designed, really,

(51:51):
really beautiful graphic design,beautiful template, it displays
properly in the email client,it's it's rich with media, it's
it's it's just very welldesigned.
And then you have another emailwith the exact same copy, exact
same content, but the thetemplate is is mediocre, it's

(52:13):
average, it's justrun-of-the-mill.
And Then you have a third email.
So again, same content, the,the design is bad.
And Then into that, into thatgrouping, which obviously we
know that, we know that howthose would be grouped in terms
of quality, into that grouping.
Where would you place a plaintext email?

(52:34):
Would you place it in betweenthe, the perfect and the average
, or would you place it belowaverage?
Where would you place that?
And it's funny, you asked thisto a few people and it's not
unanimous, but I would say 90%will say it's above the average.
It's not gonna replace theperfectly designed, beautiful

(52:55):
email, but I would put it abovethe average designed templated
email.
And what that tells me is thatthere are an awful lot of email
marketers out there, a lot ofbrands out there, who could
actually cut their expense indeveloping email campaigns and

(53:15):
increase their their efficacy atthe exact same time, simply by
simplifying how they think aboutdesigned emails.

Yuval Ackerman (53:26):
Yeah, absolutely , and I think that a good mix of
the two, if not if all of them,could be a really interesting
thing to look at.
I'm also thinking specificallyof all kinds of Email lists
where I know for a fact I meanand that's a good thing that
they did in the expectationmanagement Part of the, the

(53:49):
welcome experience I expectthey're designed to be below par
.
I expect they're designed tolook like it was.
You know, you just dragged itout of a 90s computer.
But again, that has to do withexpectation management.
So would any of those exampleswork for Brands out there?

(54:12):
Again, it depends, they allcould work definitely.

Sam Gerdt (54:16):
It's just an interesting exercise, especially
when you relate the channelemail with the idea of what a
successful brand Looks like.
I think there's a trap outthere for many marketers that a
successful brand is going to bea more advanced design and more
advanced Presentation, whereasthe brand.

(54:37):
There is a disconnect betweenthe brand and the design that
the brand employs, the, and thatthose need to be kept Separate
but working together.

Yuval Ackerman (54:49):
I think For sure , if anything, I think that the
brands that are cutting throughthe noise know how to balance
novelty and safety for their,for their subscribers.
And those brands cut throughthe noise not, you know, by
overly designed, perfectlydesigned emails, but through,
you know, very Human to humanconnection.

(55:12):
I can tell you that one of thebrands that I read Religiously I
read their emails religiouslyis an e-commerce brand for salt
from Alaska and the owner isbasically right writing her
diary.
It's it's as if I'm reading herdiary and it's long form, full

(55:33):
of gifts, kind of emails, and Iread every single one of those
and I'm not the only one.
So she has a lot of subscribers.
So it's really those brandsthat can surprise their
Subscribers but still keep thatsafe space of we're in this
together.

Sam Gerdt (55:54):
I wanted to ask how do you feel about video in email
?

Yuval Ackerman (55:58):
Dangerous.
I mean I love linking to video.
I think that's an incrediblepractice if that fits your brand
and your audience.
I would never embed in video inemail because that's a huge
Deliverability trap that could.
That you could regret for avery long time.

Sam Gerdt (56:17):
That's, that's true.
I I do know.
I mean, I've developed enoughemail to know that it's one of
the hardest.
It's one of the hardestchannels to develop for because
there's there's not a lot ofconsistency between email
clients and you know, for thelongest time you're just using
10 year old code Because youknow you have to be able to

(56:38):
deliver to an older version ofoutlook.
I'm hopeful that that will bestandardized in the future, but
at the same time, I think if youstandardized it, you might you
might trap a lot of marketersinto thinking they can think
less about email Rather thanthinking more about it.
Is deliverability somethingthat is just constantly like?
Does it?
Does it cause a lot of anxiety?

Yuval Ackerman (57:00):
It is because most of it is unknown to the
people that I work with, anddeliverability is definitely
something that needs to be apart of the email strategy as a
whole, as in both preventativecare and also, you know, if we
need to take care of somethingright away, we need to know that
we have the people to take usout of the block list, or we

(57:24):
need to make sure that are thatyou know why, all of a sudden,
our emails are bouncing off thewalls like crazy.
How do we collect our data?
What is happening in the backend?
So, definitely something to beaware of, definitely something
to incorporate in your emailstrategy as a whole when I asked
the video question, youimmediately went to that's a

(57:46):
deliverability flag.

Sam Gerdt (57:48):
So now I'm curious what are some of those other
deliverability flags that you'rejust conscious of always when
you're writing emails?

Yuval Ackerman (57:55):
That's a good one.
Links from suspicious websiteswould be a big flag.
I want to bust a myth here.
A lot of people think thatthere are certain Spammy words
that would get you blocked.
Not the case anymore.
I really recommend you to diginto this much, much deeper,

(58:17):
because it's not.
It's not necessarily the caseanymore, but you do want to keep
your emails rather light interms of their size, and so
don't Include a lot of or toomany emails, or make sure that
you're rendering properly noemails included in the email
itself, but linked to somewhereelse.

(58:37):
Those are the sorts of thingsthat I'm looking at, to begin
with, when it comes todeliverability.

Sam Gerdt (58:45):
It's something that everybody fears.
I don't.
I mean.
I get it.
I understand why, especially ifyou rely on email for a major
part of your business, butEverybody that I know who deals
in email marketingDeliverability is something that
keeps them up at night and I'dyeah, such, it's such and it's.

(59:05):
It can be so confusing at timestoo, because it's it's a highly
technical issue for one, butthen for another we don't
necessarily have Insight intowhy there's a problem.

Yuval Ackerman (59:19):
When we see a problem happening, yeah, and
luckily there are a lot ofdeliverability experts and a lot
of Great companies that couldgive you that kind of insight.
If anyone is listening andneeds that kind of insight, I
can connect you to really goodpeople, so let me know.

Sam Gerdt (59:37):
What can we take from email marketing and apply to
other channels to get morefirst-party, zero-party data in
other areas of our marketing?

Yuval Ackerman (59:49):
We need to take it a step back and we need to
ask ourselves okay, this is ourgoal.
How do we reverse engineer ourway to getting to that goal?
Reverse engineering those stepswill give you the idea of what
is it that you want to collect.
What kind of data do you wantto collect?
When, where and how?

Sam Gerdt (01:00:13):
I'm sorry, I'm just peppering you with questions.
I find this all very, veryinteresting.
Last rapid-fire question, andthen I want to talk a little bit
more about what you're doingspecifically, because I think
it's really neat.
What do you want for the futureof email?
What's your dream if you couldhave your way?

Yuval Ackerman (01:00:33):
I really wish more brands and email marketers
will understand that we'redealing with humans and, as such
, we need to treat them as such.

Sam Gerdt (01:00:42):
I think we agree.
That sounds like a really,really great future.
Yeah, Yuval, tell me more aboutwhat you're doing with the
cohorts.
You're taking your expertiseand you're using it to train
more email marketers likeyourself.
That's my understanding.
Can you tell me more about it?

Yuval Ackerman (01:01:04):
When I got into email marketing a few years back
, I realized that change has tohappen from both sides of the
spectrum.
I'm working with bigger brandsthat have more budgets.
That's the high end, or the onepart of the spectrum.
But then there are also all thepersonal brand owners, the

(01:01:25):
coaches, the consultants thatneed guidance with how do we
market to our communities, toour audiences, in a way that
feels right and sustainable.
That's the other end of thespectrum.
When we will manage to finallymeet halfway, that's when I know

(01:01:46):
that my work is done.
Luckily, I know that my workwill probably never be over.
That's that.
What I'm doing in my cohorts isthat I gather really
magnificent people with amazingcontribution to the world who
want to write consistently andthey want to do it strategically

(01:02:06):
.
We sit down for strategy calls.
I help them with the tech aswell.
We make sure that they have aplan that they follow or not,
because life happens.
They have a plan that allowsthem to connect with their
audiences consistently in a waythat their audience wants.

(01:02:28):
I'm now running the thirdcohort for this year and I'm
extremely excited to see theprogress and the impact that
each and every one of thoseemail muscleers are making in
the world.

Sam Gerdt (01:02:44):
That must be really satisfying to be able to
influence and then see theresult.
It's like you said, when it'sdone right.
Email is such a warm andinviting channel I can think of
the lists that I belong to thatI look forward to, I think, for

(01:03:09):
any company to have a channellike that, where you say your
customer is actually anxious tohear from you.
It can't be ignored.
It's such a valuable goal, it'sthat holy grail of what we're
going after as marketers to justbe 100% aligned in that way.
If anybody's interested infollowing up with you, what's

(01:03:30):
the best way for them to do that?

Yuval Ackerman (01:03:32):
My email list, first and foremost, which you
can join at ackermancopywriting.
com/subscribe r just connectwith me on LinkedIn.
Tell me that you listen to thispodcast so I can approve you
right away, unless I'm not onInstagram, linkedin anymore and

(01:03:53):
I'm blocked, and then I'm onlyrelying on my email list.
So join my email list.

Sam Gerdt (01:03:58):
We'll put a link to that somewhere, too, so that
people can get it.
Yuval, thank you so much fortalking with me Again.
This was a little bit differentthan some of my other
interviews.
I felt like I was justhammering you with question
after question, but it's such abroad topic and I feel like you
do it very well and I'm with you.

(01:04:19):
This is something that I wantto see change for the better in
the coming years, so I reallyappreciate you taking the time
to answer all of those questionsand to give so much insight
into what you're doing.
We will surely follow up withyou soon to see how things are
going.

Yuval Ackerman (01:04:37):
Thank you so much for having me.
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