Always Be Testing

Guiding you through the world of growth, performance marketing, and partner marketing.
We sit down with growth and marketing leaders to share tests and lessons learned in business and in life.

Host: Tye DeGrange
Guest: Adam Robinson
Hype man & Announcer: John Potito

Adam is the CEO of Retention.com

What is Email-Based Retargeting?
How to spruce up your Email Marketing Game?

Timestamp:
00:00 Introduction and Welcoming Adam Robinson as Guest
01:10 Adam Robinson's Background and Journey in Business
03:22 Challenges of Competing in a Mature Market
04:20 Developing a Differentiating Feature for Email App
06:21 Impact of Changes in Facebook's Tracking System
07:14 Difficulty in Understanding Tag Management Solutions
08:30 Target Market for New Product and Challenges
09:32 Performance of Email List and Major Customers
10:43 Importance of Efficiency and ROI in Business
11:59 Balancing Value and Pricing in Business
12:24 Lessons Learned and Reflections on Growth
15:14 Changes in Sales Department and Hiring Process

What is Always Be Testing?

Your guided tour of the world of growth, performance marketing, customer acquisition, paid media, and affiliate marketing.

We talk with industry experts and discuss experiments and their learnings in growth, marketing, and life.

Time to nerd out, check your biases at the door, and have some fun talking about data-driven growth and lessons learned!

Welcome to another edition of the Always Be Testing podcast with your

host, Ty De Grange. Get a guided tour of the world of growth, performance

marketing, customer acquisition, paid media, and affiliate marketing.

We talk with industry experts and discuss experiments and their learnings in growth,

marketing, and life. Time to nerd out, check your biases at the door, and

have some fun talking about data driven growth and lessons learned.

Hello. Hello. Hello. Welcome to the Always Be Testing podcast. I'm your host, Ty DeGrange,

and I'm thrilled today to have Adam Robinson. What's up, man? Hey,

Ty. How are you? Thanks for having me. I'm good. I'm good. I am excited

to dive in with you and talk about all the things retention and,

business and life. We, we dive into some learnings here, and it's usually a lot of fun. And

let's, let's roll in and do it. Let's do it. Yeah. So so Adam Robinson, for

those of you don't know in the audience, he's the CEO of Retention dot com. He's had some

awesome learnings in various areas in business. He's made some really

great build in public kind of comments and and candor and his experiences in in

building and really excited to dive into it. He's a prominent d

two c e comm, personality and business person in marketing in in the,

Austin area. It's nice to be here in the same area with you. So let's let's let's jump in.

And as we were just talking about, if you were a DDC person in the Austin area and you wanna

get involved in if a listener is and you wanna get involved in my direct

consumer wake surf club, I do it once a month in the evening on Wednesdays,

Email me adam at retention dot com. I would love to invite you. There you go. It's a

good call to action. Right? Let's let's let's get people involved right

away. Yeah. Just right off the bat. Beautiful. So, Adam, tell us about your

background. How did you get into all this stuff? I was a trader. I lived in New

York. I trade I worked at Lehman Brothers and traded credit default swaps for ten years. They made a movie about that

called The Big Short. When I showed up in New York, my roommate started Vimeo, the

video sharing website, in my apartment. I watched that whole thing happen, and it made me think that I

wanted to be like him. And I did. So That's amazing. After

the financial crisis, I quit. And I'm like, I've saved some

money. I could spend it on business school, or I could spend it trying to make myself an

entrepreneur. So I I opted for the latter, and it just started

this five year, like, bare knuckle brawl.

It was horrible trying to get my first company to sustainable.

And it happened to be that it ended up being in the email marketing space. I don't particularly

care about email. I know a lot about it now. But, like, it wasn't like, follow your passion.

Okay. Email marketing. Right? Like, it just, I was working on five different things, and it happened to

work. So ten years later, I end up knowing a shitload about email. And that

company was a really good lifestyle business, but it was in in competition with Mailchimp and Klaviyo,

which is just like a it's a horrible space to be in. Like, into it's like I like to say it's like

selling cola against Coke and Pepsi. It's, like, super mature. The products

are very undifferentiated. Like, it's all brand, and they're spending billions of dollars on

marketing. It's just impossible to compete. So Yep. I was always trying to figure out how to

break out of this ceiling. Like, I was just stuck. And, I was trying to do

stuff Mailchimp wasn't doing because it was just such a hard offer to compete with. Like, how are you gonna

be more free than Mailchimp? You're not? You know?

Came across this identity stuff, and it was so intriguing to me. You know, the idea that you could

get an email address out of a person who didn't fill out who didn't give it to you. Right? Like,

somebody could hit your site, and you could just know who this person is. Captivating,

right, to somebody who's never heard of it before. It's like sounds like magic. So Mailchimp definitely wasn't doing

that, and they never would. So I set off on this, like, year and a half journey of

trying to figure out how to do it. Finally figured it out. My idea was that it would be what

differentiated my email app from the rest. Launched the feature.

Everybody used the feature. Nobody wanted to use the rest of the platform. So it became clear to me that it

was a bad product if it was inside of my bad ESP. It was a

great product, probably. You know, every indication is that would be if I spun it out,

connected it to everything, and then launch it on its own. And that was, like, twenty twenty,

basically, November twenty nineteen. About a year and a half ago, it became clear to us that big

Shopify stores were, like, our power users. Like, never churned, paid

us way more than nobody else, bought faster than nobody else, never submitted a single support ticket and referred

all of their friends. And we're like, okay. That's the audience we should focus on. We

built some more features for them, like product cart, checkout abandonment, audience

expansion. And here we are today, and we're

about to so, like, kinda one of the problems now is we can really only sell to

stores. Like, our products amplify whatever throughput is going

through a Shopify store. So if there is a lot going through, there's a lot we can amplify, and the product

looks really good. The lower that revenue number gets and the lower those abandonment Yeah.

Emails flow revenue gets, the harder it is for us to actually show return on what we're getting paid.

Because, like, below a certain point, it doesn't even make sense for us to, like, onboard people.

I'm really excited that we're about to launch a sixty dollar a month product

for everybody. And the problem that it is solving is

massive. So I call it the signal gap problem. There's all of this

stuff happening on your Shopify site. Apple is ratcheting down every day

on the events that can actually make it to Meta and Klaviyo. On

April twenty third this year, they ratcheted Meta and Klaviyo back to

seven days for tracking people, which is a massive fucking problem. Like, if

somebody clicks through an ad Yeah. That it used to track them for a year. Right? Six

months, whatever. Now if they click through and they come back eight days later, Facebook has no idea who they are,

which you're like, okay. Who cares? Well, the reason Facebook works so well is because

they knew who that person was looking at a product, and they showed them an ad. Now

all Facebook sees is an anonymous user. So our sixty dollar product we'll track

that person for six months to twelve months or something like that, depending on whatever. Pretty compelling

case. And for the Klaviyo flows, it's the same problem. Right? If somebody puts something in the

cart and leaves eight days later after they bought something, no nobody. Like, it's

nobody to Klaviyo. So I'm really excited. There's some other vendors

who solve this problem through a different solution. One's called Elevar. One is

called BlotOut. One is called BlackRock AI. They're doing tag management. It's like a much

it's like a super heavy install installation, and it's very difficult to understand from what's written on

their website what it actually is and why you would need it. I'm doing a

done for you. Literally, you just, like, sign up on a type form, give us Shopify and Clavier

permissions, and we'll just start emailing you the money we make you for fifty nine dollars a month.

This is, like, I've never been so excited about a product. That's awesome, man. It's normally,

like, you kinda go the other way. You, like, start at a really low dollar price in SaaS, and you go up. Like,

we started at this twenty k ACV, and now it's, like, very clear to me that

there's such a like, this is as big of a problem for a

smaller guy. It's just Yeah. If If you have to support your business with the Salesforce, like, you can't you know, these

these other Yeah. Solutions are too complicated to sell

to someone at at that price. Right? Like Yeah. You're basically going to, hey. We're our

customers are Shopify ecom consumer fifty million minimum

a year, right, revenue to almost everybody. Is that is that kind of the

Well, right now, it's three million and up. But still, that's only,

like, six to ten thousand stores depending on what dataset you look at. Yep. It's

not a lot. There's two two point five million active Shopify stores. So I

think this new product is probably for, like, a hundred grand to three million

of GMV, and I think there's, like, two hundred thousand stores in that

band rather than, like, ten thousand. Right? And they they should all be able to to

see value off of it, but, like, this is the the remaining question is, like,

how small is small to where either they don't see value or they just are like, I don't even

care. This is a hobby. Yeah. Do they know it's a problem or they want to address

it? Yeah. Do they even it's like, yo. I can make you a hundred and eighty bucks on a

sixty buck investment. It's like, I don't care. But I have other stuff that's way more pressing than

that. Mhmm. That's amazing. So we'll see. Wow. That's really cool.

For the brands that are already engaged in the retention product and we I wanna dive into the new product too. But,

like, what are some of the big, like, outcomes you've seen with

retention, with with some of the chain the core product? So the core product,

like I said before, it's like True Classic and Doctor.

Squash are two of our biggest customers. They both make over five

hundred thousand dollars every month, and they pay us, like, ten to twenty grand. That is not

indicative of a normal store. So, like, the dynamic with our

product, like I said, is, like, the more volume that's going through, the more we can

capture and amplify, And our pricing doesn't increase like that. Like, we just couldn't

charge doctor Squatch two million dollars a year to, like, use our product. It just doesn't pricing

doesn't work like that. Yeah. So it's a little unrepresentative

of what a normal outcome would be for somebody who has, like, a five million dollar store or, like, a three million dollar

store. We do like to beat other channels on a twelve month basis very comfortably.

So if, like, people are looking for two to three x, it's, like, I think four to five x over the course of twelve

months. Like, given the the holiday, it will kick up, and then it will calm down afterwards for for a lot of d to

c. At the smaller end, which is like a three million, like, that's what we're trying to do, be

at least five x over twelve months. You know? Yeah. And that efficiency is awesome to

be able to say, hey. You're gonna add something that's significantly more efficient

than a lot of other levers you can pull is is huge. Yeah. That's amazing.

It's a high bar. You know, I've questioned whether that's even the right sales strategy because

kind of a problem we have, we have we have a right now, this is our deal structured. I don't know if it's gonna be like this

forever, but we have a sixty day opt out. And, basically, it's like a twelve month deal

with sixty day opt out. And, basically, the performance

kind of accumulates over the course of the year because, like, one of the products is we're just selling the the

the people list of emails. And these emails, they come back and they repeat purchase. And kind

of the only way to look at how that list performed over the course of the year is look at how many

purchases there were over the course of the year. I think the only way to test it is do a holdout test.

You hold out five percent, don't mail them. You mail the other ones, and then you see what the incremental would

be that way. But, like, when you're talking about ROI of a list, it's just gonna

go up over the course of a year as these emails buy, and we give you more emails.

But then we're, like, holding this gun to our head saying, if you don't see what you want in sixty

days, just quit. It's it's confusing to me whether we're doing the right thing or not

with pricing. Yeah. I think a lot of businesses in in our world struggle with

that a little bit to determine, like, how do we offer a ton of value but don't

undercut ourselves or go too far. You know? Yeah. Yeah. Or just set expectations in the wrong

way Mhmm. Which I think is a large a large part of it. Absolutely.

It's like you wanna move fast, but if you move too fast, then you're not explaining

it well enough. It might be a good, segue in a little bit.

You've talked a little bit about, like, lessons learned. What are what are some of those big lessons you've learned

this year? Oh, god. For background

on this year, in October of last year, and it's currently

July twenty seventh. In October of last year, we had six employees, and

we were at thirteen million ARR. We hired like fifty

in sixty days because we identified the Shopify audience

as our perfect candidate. And then

I didn't really we didn't know a lot about the universe. So, like, we sort of overestimated

the size of the market. And then we were also being a bit

we were overselling people, like, just because of how it all played out. You know? It

was like Mhmm. So the overselling people and

overestimating the size of the market made us think that the TAM was actually much I thought there was fifty thousand

stores that we could sell to. And it turns out there's, like, six to ten. Right? And I thought we were doing a thirty

thousand dollar deal, and it turns out we're doing a sixteen or eighteen thousand dollar deal. So, like, this opportunity

set's just, like, way different than I thought. Mhmm. So, like, we hired too many people. You

know? I, like, I had this vision of in the beginning, like,

let's have a lot of people creating demand out there with these partner channels and agencies and events and everything else, and then

we'll have just, like, a few AEs who are just flooded with all this demand. And I thought, culturally, that's,

like, a great thing for an org. Mhmm. Like, a salesperson's on the phone, and they're like, if you don't buy this right now,

yep. I have, like, four other calls today. Like, it's just a good mindset to be in.

Yep. Creates scarcity and demand. It's like overestimating the TAM and

overselling people. It's like, I've made this crazy goal to get to fifty million ARR by

the end of the year. And we were at fifteen at the end of last year. And

it just we hired too many people. Then all of a sudden, it's like, well, we like these

people. And and by the way, like, in April first, like, everything stopped for for people selling

into these stores that we sell into. Like, for whatever reason, it was just this weird slowdown.

So we kinda pivoted the org to be like hunters.

And then last week, which, like, it's just a different feel.

Right? Like, everyone's calendar's twenty percent full rather than, like, a few people's calendars a hundred and

twenty percent full. Mhmm. And then our VP sales, he has his reasons.

You just had a kid. He resigned last week, and then we decided, do we

replace this guy, or should we just take our sales team from fifteen to four and go

back to, you know, what we had intended originally before all this happened? So that was like

something happened in sales work. Wow. We're hiring for five roles right now. It's not like we're

Yeah. Sort of, oh my god. Like, the walls are on fire. Like, I think we're gonna generate,

like, three hundred and fifty grand of free cash this month. Like, it's not a, oh my god. We're,

like, we need to get smaller. We need to get smaller for Yeah. So, like,

things that I learned, I felt like there was this land grab that that needed to

happen, and I was, like, very desperate. It was like a FOMO feeling, almost like

buying crypto at the highs. You know? Very similar. Like, and

it's just not who our, like, our team is as a company. It's

not there's this saying, what got you here won't get you there. But, like, I don't

think that the fundamental elements of what I deem an excellent business or

what I would look at and be like, that is the best business, which is, like, in many

ways what I had before we did this. Like, to me, it's like, I love in SaaS super high

revenue per employee, super high capital efficiency. I like profitable

companies with strong growth. I like kind of this paradigm. It's not necessarily

an inbound sales model, but this paradigm where Mhmm. It kinda always feels like it's

busting at the seams as it's growing. Mhmm. And that's because, like, product's getting pulled out of

you. You're at the you're at the right size to where it feels like the market's pulling product out of

you. And any company, you can fuck that dynamic up by just, like, having three times as many

people in the department as there should be. Right? So Yeah. There's just a lot of lessons in

there. I also felt very desperate to get our brand out there, and I just sponsored anything and everything,

newsletters, podcasts, this, that, the other. And, like, the other lesson is when you're doing that and

you're living that way and you're hiring people and they're spending money too, it just sets a horrible,

cancerous sort of literally like a death.

Like, we would have never been profitable no matter how much money we made if I

kept living like that. Yeah. So, like, another great lesson was just, like, if you don't

run and by the way, we were running we were paying dividends before. Right? So, like, when you're, like

our executive team's all getting these huge checks. It's like, you're really thinking about, like, okay. Do I

wanna spend fifty grand sponsoring this event, or do I wanna, like, pay myself

thirty grand and my two cofounders twenty grand? Right? Like, thirty grand's pretty nice.

Extra. Right? Yeah. It'll add some. So it's not it's not that you don't do that stuff. It you you just have

to really want it when it's, like, cash in your pocket or

but when it turns into this thing where it's like, we need to be everywhere. You know? It it felt like a venture backed product, and and

there's no accountability for, like, budget or, like, the value of money or anything. It just it goes

off the rails so fast. So that was another massive lesson that I learned. Just like if you

don't run a tight ship, especially when you have a lot of people spending money, like, you

will never be profitable ever. The only reason we weren't unprofitable is because I didn't have

any money in the bank account when we started hiring people. Like, we had six hundred grand of

free cash flow, but we were distributing it out. There was only a couple hundred grand in the bank account. So, like, we

couldn't burn. It just got to the point where it's like, alright. Now we have to stop spending money. And by the way, this is

terrifying. Like, we have to, like, fix this problem somehow.

So that's another huge lesson lesson that I hope no one has to learn because it's it's

just brutal. I feel you, and I I've been through similar kind of evolutions as an

entrepreneur and a business leader, and you learn. You have to sometimes go through those lessons.

And I think in the last couple years, not it's not like a lot of entrepreneurs

didn't have a good financial rigor internally or a good finance

person or I just think people have sometimes you do have to legitimately

learn those hard hard lessons, and then you kind of recalibrate and apply. And

and and it's not always that you're chasing for the wrong reasons. You're an entrepreneur because you are trying to take

a swing for the fence and make something happen and take care of your people and your customers.

And so it's, it's understandable stuff, and it's not easy black and white or else

everyone would do it. Like like you said earlier, you you don't just go to business school and plug in and expect to make

a make a unicorn. You there's a lot of things that have to go right, a lot of decisions that you've you've had to

have made along the way just to get to where you are. It's impressive. Yeah.

Many more wrongs than rights. But, like, the idea is that you get,

like, eight wrongs in, like, two rights. One of them's okay, and one of them's great. That's

what I've observed. I love it. You've talked a bit about bringing in the

right people as a company. We've felt it and learned it and lived it and bringing

making sure that right person's in the right seat. When you think about talent and and

those concepts, how how do you approach it, and how do you kinda get it right more than get

it wrong? Oh, man. Well, it's so hard. So, like, I have a

lot to say about I mean, we just had a VP sales that quit. Like, he fucking we didn't fire him. He

just quit. He just was like, I'm not I can't take it. Yeah. Strangely,

we added two people to our executive team last October,

and it literally felt like a family. You know, like, it

cultural it felt like they had both been there for ten years. Amazing. We have, like,

identical values. And think about business in the same way and, like, are, you know,

principled in the same way and, like, whatever. On February first, we hired,

like, seven directors and VPs. One remains.

Wow. Like, it's that level it it's like, and, look,

part of it was there were just a lot of things that happened since February in this market

that we're in. And, like, this guy this VP sales leaving. Like, we weren't gonna downsize the

sales team if he's was managing them and stay he just decided he wasn't the guy. And

it's like, well, I'm not gonna go find another VP sales right now when, like, Diana

can just go from the CRO role, do it, manage four people, figure out a b to b product for you know,

it's like Mhmm. The answer is I don't know how to hire peep this

attempt, I would consider that a fail. I I would hope that the

next time we do that like, maybe we hire VP marketing at some point. Like

Mhmm. Man, it's just so hard. Like, we hired this incredible VP partnerships

who was the right guy at the right time. I thought the agency thing was gonna be everything

for us. And when it played out, the agency

motion that worked for us looked a lot like an affiliate or influencer motion. It was

like not the agency owner being the gatekeeper of our technology because our

technology is perceived as somewhat risky, and it's just not in the incentive of an

agency to direct attention of their employees to deploy this. Almost in any

circumstance, there's a certain type of agency that will. But, like, the thousand dollar, five hundred dollar a month commission

is just, like, not even to jeopardize a twenty k customer for that, it doesn't make sense.

Right? And, yeah, I mean, we combined our teams,

our partnership teams, because they were basically doing the same thing. And there was, like, territory conflict and all this. And then

this guy, we all voted that the guy on the other side was the right

one to run the whole team. And then you're in a situation where it's like, okay. This guy's making, like, you know,

three times as much as the guy that's gonna be his boss, and he's VP partners from the other guy's director of affiliate.

Like, it doesn't work. Right? So, like, I don't know how I would have ever

foreseen that, but this guy is incredible. Yeah. It it's almost

like it's like a butterfly effect in a weird way where, yeah, you could

have gone out and reinvented the wheel and hired a new VP of sales, but you weren't going

to. And not to say that if folks coming in are leaving

dictate your moves as an organization, but it does make a material impact.

And it's it's a bit of a butterfly effect, three d chess where it's like, okay. This person

leaves. Someone, you know, your CRO can absorb Yeah. To manage those four people.

And we're off to the races in a similar approach, but it it kind of had puts a little bit

of a fingerprint on the organization and changes how you, address it.

I had wanted an excuse to get way more lean anyway, and that was just like the catalyst.

Like, I've been something I'd felt wrong about how that team was operating

relative to, like, how I had dreamed that it would operate. Then, yeah, it was just the perfect

catalyst. Yeah. Are there not to give the whole financial model to people,

but is there some, you know, get lean things that you think about? I mean, I

think there's some, you know, good best practice out there in SaaS and in sales and marketing, and we can

talk about those. But is there anything that kind of hit you recently in the last couple years where you're

like, man, I really need to be hitting this? I I have I certainly been much more

cognizant of that in the last few years myself and, focused on it.

I had just always loved running businesses that generated cash. Especially in SaaS,

you have to operate a it's crazy. No one does that. Like, if your breakeven are a little

profitable, it's, like, amazing. But, like, I was running this business. It was, like,

fifty percent total margin or something like that. So, like, there's just a way you behave

when that's the case. And I don't know. I should think about, like, how to articulate it, but

it's kind of like Mhmm. You just are, like, really scrappy.

And, like, what Yeah. Everyone else pays fifty grand for, you try to figure out a way to pay two point

five grand for. Yeah. And it can be done. You can create

incredible experiences for people and be very impactful for, like, very

small amounts of cash if you're just willing to be creative. That's such a great reminder. Yeah.

You you touched on values a little bit, and it's kinda like the core of the leadership team, and

you guys were really clicking. Can you elaborate on on those values a bit

and, like, what what kind of you hold dear and what kind of seem to having you guys sing the same

song? Yeah. So I think we're all this, like, bootstrapping scrappy

mentality, like, first and foremost. Really kind of old school in the way that we

think about the value of a dollar and how precious it is as the lifeblood of your

business. Mhmm. You know, people are very straightforward. We're

excellent at communicating with each other. I don't know that sometimes people outside of our

circle would probably say that we're not good at communicating with them, but

it's very fluid in this executive team. Yep. And look, they're all just super high

integrity individuals that have very similar motivation. Yeah. It's it's a

lot of the it's just a really good business partnership. I love

it. What's something that's kind of like a life hack or a thing that you're

you're doing personally that's kind of helped you get through all this stuff and and succeed

in as much as you have? I try to just do the basic stuff. Exercise

at least five days a week. Eat well. I quit drinking a few years ago.

Major life hack. Get good sleep. All of that. Look at the

sun. Like, go outside during the middle of the day and just, like Yeah. Look at the

blue sky and, like, let the sun hit my skin. Like, all of the stuff that you

can't really measure, but I just think it's, like, the core, like,

community, spend a lot of time with family. I have a ten month old daughter. So, like,

just really Nice. There's not really much else. But, like, when I'm not here,

I'm trying to do stuff that is very basic human needs, time tested happiness

stuff. Yeah. That's amazing. Couldn't have said it better. What do

leaders need to do more of? What do they need to do less of? So I'll tell you what I'm

trying to do. I am trying to do more focusing on

like, list that's, like, two things or three things maybe. And until

those are done, I'm not going to my sub list that I am constantly adding stuff

to. That's what I think I should be doing more of. I love

it. This is awesome, man. I could go on for hours. I know you

got your your surfing. I wanna be respectful of your time because I think

this has been a good thirty minutes of juicy bits, and,

we can all you know, we can always pick up more in the future and excited to venture

out into the surf world with you and hopefully see it at a little gathering tonight. But, yeah, I

just just wanna thank you for coming on. It's been awesome to chat with you, Adam. Well, thanks,

Ty. I know we can go deep on a lot of things and and nerd out on other stuff

too, I'm sure, and, hopefully, get together in person soon. So Rock and

roll. We'll take care. Appreciate you, Adam. Thanks for coming on.