How Eli Weiss Got a Sponsor & 1,000 Subscribers Before His First Send

All Things CX & Retention is a newsletter all about optimizing a brand’s customer experience to foster better retention.

Its creator is Eli Weiss, the Senior Director of CX & Retention at Jones Road Beauty.

We recently sat down with Eli to discuss his approach to building a successful newsletter in the highly saturated marketing space. Eli was happy to share how he essentially created a space for himself in the market, how he approaches newsletter content creation, and how he secured a sponsorship deal of $1,000 before he sent a single issue of his newsletter.

Key takeaways:

• The story of how Eli got started and learned everything on the fly.

• How he got his first 1,000 subscribers & paid sponsor before sending his first email.

• Several pointers on content strategy (topic selection, originality, etc).

• What he does to secure highly engaged, quality subscribers.

• The approach he takes to maximize his newsletter revenue.

It’s an incredible interview, and if you’re curious to learn more, you can signup for Eli’s newsletter here:

How a Trip Across the World Landed Him in CX

Eli’s story starts with an adventure around the globe. After he finished high school, he travelled the world by leveraging over a million miles in credit card points. After his travels, he naturally found himself working in the travel space for a Kickstarter startup that was selling luggage.

But Eli didn’t have a prior passion for customer experience. He shares how he stumbled into the role by chance.

“I started my career in customer experience in 2016. I got into CX [customer experience] because it was the easiest startup job to get. And I thought I had a leg up on others when it came to reading between the lines.”

Eli didn’t realize he was walking into a storm. He shared, “[The Kickstarter] was two years delayed in production. 95% of the customers were angry and wanted a refund.”

Despite the bumpy start in the CX world, Eli continued to grow, learning everything he could about customer experience, e-commerce, and retention.

“I started in a CX role, was there for four years, and did everything from operations, logistics (shipping to 64 countries), running Facebook ads, launching in multiple markets, going to trade shows, etc. I did it all and learned a ton.”

“Then, I jumped into “Nuggs,” which is now called Simulate—a vegan Chicken Nugget Alternative. I jumped there in 2020. Then I was at OLIPOP, which is in the food and beverage universe. I was there for almost two years. I'm now at Jones Road Beauty, one of the fastest-growing beauty brands founded by Bobbi Brown (formerly of Bobbi Brown Cosmetics), and I lead all things customer experience and retention.”

Learning to Fly on Twitter

Eli shares how, while many people on Twitter start their accounts with the goal of monetizing, he didn’t. He just loved CX and wanted to share his take on it with the world.

“I was sharing CX for a couple of years now, based on a conversation I had with a guy named Ben Levy, who started the Milk Road newsletter. Before Milk Road, I was chatting with Ben in 2020. We met on an Andreesen Horowitz-backed networking app called Lunchclub.”

“[Ben asked] ‘What do you love to do?’ And I'm like, ‘Sitting and talking about CX nonstop.’ He says, ‘Why don't you talk about it? Your Twitter has zero about it.’”

Eli was hesitant about sharing about CX because he thought nobody was interested in the topic.

“I said, ‘Nobody gives a s— about any of this stuff. CX is not a thing. People love talking about growth on Twitter.’ He was like, ‘Just try it.’”

Those three words would put Eli on a trajectory that placed him at the mountaintop of the CX space—surprising him both in terms of the demand for the subject and the result of him putting himself out there.

“I started tweeting about [CX], and I went from 200 followers to 1,000, to 2000, to 5,000.”

$1,000 & 1,000 Subscribers Before the First Newsletter Send

“I’m talking to exactly the people I want to talk to with a 55% open rate—a very niche audience about a very niche topic. On a practical level, building niche was actually much smarter for me than going broad because everyone's broad.”

Eli’s Twitter was taking off. One thing led to another, and people started asking him to share about CX in-depth—particularly, more than Twitter’s 280-character limit would allow.

“I just continued growing [on Twitter], and I got to have a bunch of conversations where people were like, ‘You have this different view on what customer experience is versus what it could be—what it should be. Why don't you share more long-form?’”

But, like many introverts, Eli was quite reluctant to put himself on a public pedestal—even a digital platform like a newsletter.

“I spent most of my career just hiding in a corner like most introverts do. I'm not an influencer or a newsletter writer. But, I was having a moment where I was like, ‘This would be fun. I love writing. I never write long form’. I tweeted, ‘Hey, would anyone be interested if I launch a newsletter?”

To Eli’s surprise, he had “a ton of responses.”

Here’s where Eli took things to the next level. He didn’t just ask his followers if they’d read a potential newsletter on CX and retention. He asked them if anyone would be willing to pay for a sponsored ad in his newsletter from the get-go.

“I wrote under that [tweet], ‘Would anyone be interested in sponsoring it?’”

The result? He had not one, not two, but three people reach out to say they were interested in sponsoring his newsletter. One of the three brands was Wonderment: a post-purchase tool that Eli uses at Jones Road Beauty that automatically reaches out to customers if their order is delayed.

Eli shared how enthusiastic Wonderment was to sponsor his newsletter. “Whatever it is, we’re in. We want [to sponsor] the first six newsletters. They didn’t know if I had anyone [subscribed]. This was before I got a thousand people. That was on a Wednesday. By Thursday afternoon, I had a thousand people signed up from a tweet and this LinkedIn post I shared with the audience I built.”

“I was seeing beehiiv pop up everywhere. This is almost a year ago—right when you guys launched, and I said, ‘Let me take a look.’ I launched it [on beehiiv] and had 1,000 subscribers before I sent my first newsletter and had a sponsor secured. It's been 45 weeks since then, and every single newsletter is sponsored.”

If you want to launch, grow, or monetize your newsletter on a platform built for growth, sign up for beehiiv today.

He Gave His Followers The “Right Hook” With His Newsletter

Eli shared how he decided to take a different approach to sharing marketing wisdom by being vulnerable and transparent by sharing his personality through his tweets.

“My following is really, really strong, because I'm myself as much as I possibly can be. I think that's what gave me a leg up. If I had done things differently, if I was not me on Twitter, I don't think I would've gotten a thousand people signed up before I launched.”

Providing value to his audience, rather than getting too salesy with them, was important for Eli.

“So the newsletter was the first thing I ever asked from my audience, right? I'm not the guy that's like, ‘Buy my course! Buy my course! Buy my course—now! Sign up for my newsletter!’”

But there’s a better way.

“It was so much give, give, give—like the Gary V “Jab, Jab, Jab, Right Hook.” This was my first right hook. This was the first thing I ever asked people for. I said, ‘If you enjoy my content, if you enjoy me nonstop complaining about the current [CX] situation, and how I think we can make it better, sign up for this newsletter.’”

The 9 to 5 Lie

While many people are hesitant to start a newsletter because they’re still in a 9 to 5, Eli shares how it’s actually an advantage for his newsletter to keep his day job.

“[The newsletter] works because I have a nine-to-five job [in CX]. If somebody's sitting across the world writing about CX, but they don't work CX, That’s not interesting. The reason why it's fascinating for people is because I'm doing it all day.”

“This is my job. This is my life for the last eight years, and I'm writing about the things I'm seeing in real-time, which actually makes writing a newsletter easier because you have consistently new things to talk about based on what's working and what's not working.”

High-Quality Subscribers = High Engagement

Eli shared how his newsletter has grown early on primarily because of word of mouth, and more recently, beehiiv’s Recommendations feature. But, for him, it’s not so much about how big he grows, but about focusing on the right audience.

“Prior to beehiiv recommendations, growth has been 90% word of mouth from people in my ecosystem. It’s marketing direct consumer (DTC) people and people that found me on LinkedIn. I did two or three newsletter swaps. But it's predominantly word of mouth. In the last couple of months, I've had beehiiv Recommendations, which has been crushing it.”

“When it comes to every single quality person that joined my newsletter, not just people that signed up and signed out—they're all word of mouth. My open rate is consistently 55% plus because these are all people that are genuinely interested. I'm going for quality.”

Enjoying this Creator Spotlight? Learn how The Neuron newsletter grew to 10,000 subscribers in the first month!

The Weiss Advice on Newsletter Content Creation

Eli Weiss has plenty of golden nuggets to share with other creators about running a successful newsletter. His tactics involve valuable advice about coming up with content your readers love and focusing on the right subscribers.

Coming Up With Sticky Content: It’s All About the Topic

Eli shared that the majority of his content creation effort is placed in the ideation phase rather than writing on its own.

“95% of the work is a topic. I tell this to my wife all the time, ‘If I can come up with a topic, everything else is easy.’ I could spend an hour and a half formulating a topic and the writing can take the same amount of time. The topic is by far the hardest part.”

“I'll start writing it on Monday, finish it on Tuesday, have somebody look it over on Wednesday, send it to the sponsors and have them look it over. It goes live Thursday. By Thursday afternoon, I come up with a bunch of ideas, knock them because I'm very ridiculous, and then I'll finally come up with an idea that feels somewhat sustainable.”

“Now, where does [the topic] come from? A lot of it comes from content that I'm consuming and from this place of feeling the way we're talking about a certain issue is not the correct way (in my opinion) of how I would tackle it. I'll consistently talk about how the way we're viewing retention is silly.”

“We're just continuing to send emails, send SMS, but we're not fixing the core issue at hand. That was something I was frustrated about by everyone talking about retention as if it's just email and SMS. I was thinking about how at Jones we're building this nine-figure brand by focusing on education.”

“Education is not a topic enough people are talking about. If you want to keep people coming back, make sure they're getting value from the product before upselling the next product. That was a topic I was ranting about in my own head. How do I turn that into a newsletter? How do I bring examples? A lot of [newsletter topic ideation] comes from the work I do.”

Streamline Content Creation With a Solid Format

If Eli was going to continue to come up with an original weekly newsletter on top of his already jam-packed 9 to 5 and family life, it had to be streamlined. He found that by creating a templated newsletter format, he was able to keep people engaged while keeping his content creation process efficient.

“Writing original content every week is really difficult. So what people do is regurgitate things they've written in other places: read this article and rewrite it a different way. I've tried really hard to keep a certain format, so it's always a little bit personal, like, ‘Here's what's going on in my life,’ which is a trend that I'm seeing more within my circles since I started doing it.”

“It’s fun, it’s not a newsletter, it's me writing a newsletter. It's, ‘Here's what I've been up to this week.’ It can be a dinner I'm hosting next week, the store we open. Then it's three bullets about here's what we're talking about, the sponsored piece. Then I jump into it and split it into a bunch of easy-to-read paragraphs.”

“I'm really focused on people having an easy time grasping what I'm talking about and getting through it. So the format is something I'm crazy, crazy, crazy about.”

How Weiss Integrates Ads into His Newsletter

“My personal goal was to align with sponsors that made sense to me. It doesn't have to mean that I use the tool. But there are certain tools that I would tell other people to avoid or have nothing to do with me, period. If somebody reaches out, ‘Hey, we have this AI tool that helps with x, y, and z.’ It sounds cool, but I don't think my audience will want it. I'm a CX guy, and I really want people to have a successful experience running an ad. If somebody's like, ‘Oh, I have a gardening tool, can you put it in your newsletter? I'll pay you six grand.’ I'm like, ‘Absolutely not.’”

“I can cater the newsletter based on the product. For example, Tapcart advertised with me. They build mobile apps. They were talking about retention and they said, ‘Can you talk about multiple ways to make retention better?’ I thought, ‘Oh, that's an easy thing. I'll write about it.’ I was wanting to write about it anyway, it goes very well with Tapcart.”

“I did a sponsored ad for Nik Sharma’s Hoox landing page agency. I was talking about education and landing pages are great for educating customers pre-purchase, so it fits in so natively. When you're doing like 2, 3, 4, 5 sponsors, either it feels funny, or it's mental gymnastics. And there are people that do that well, can have two sponsors and fit them both in, but then it just ends up being very difficult for me. So I prefer having one sponsor (something I'm aligned with) and then building it that way.”

Pulling the Strings of Supply & Demand to Maximize Revenue

One way Eli’s newsletter is different from the typical newsletter is how successful he is with a smaller list. He says he doesn’t focus on the size of his list but, instead, on the quality of subscribers, sponsors, and content. This unique newsletter approach has resulted in an extremely valuable email list.

“I have like 6,000 [subscribers] on beehiiv, and another 2,000 on LinkedIn. It’s not always about the [list size]. I talk to people that have newsletters 10 times my size, and they don't make a fraction of what I make.”

“When I was really small, my first sponsored post was $1,000, which was very expensive for having 1,200 subscribers. My current rate is closer to $3,000 now. [The CPM] is about 30-40 cents.”

“If you look at some of the large newsletters that have 120,000-150,000 subscribers, they're asking for like $2,000, but they'll have 15 classified ads. I'm so obsessed with experience, which is the reason why I want exclusivity. Instead of taking $1,000 from five sponsors, I'd rather take $2,000, $3,000, or $4,000 from one.”

“Some people say, ‘Wow, this is so overpriced. I just paid someone who has 35,000 subscribers and I paid him the same amount.’ And I'm like, ‘He's your guy. He's giving you a great price. I can’t always compete on pricing, but there’s no other CX and Retention newsletter.’ It’s kind of like a supply and demand question.”

Eli shared that while the majority of newsletters are focused on increasing their subscriber counts and email sends, he’s doing the opposite.

“People think about it the other way. ‘Let me do four newsletters a week. I'll hire VAs, I'll repurpose the content.’ Some of these big newsletter companies will be like, ‘If you want to make money with a newsletter, you must send it at least twice a week.”

“You can make the same amount of money sending half the time and doubling the price—if you have inbound interest. If I did a newsletter twice a week with two sponsors per subscriber, I'd net the same amount of money, because I would have to charge less. I think the supply and demand thing is working for me because I'm very niche. As you go wider, it's probably a very different story.”

Niching Down: An Introvert Getting Loud in a Quiet Place

As mentioned in the previous section, Eli can charge a high fee for his relatively small newsletter through the power of supply and demand. He pulls the lever of supply by limiting his newsletter to one send per week and one sponsor per newsletter.

However, there’s another lever that Eli pulled before he even started his newsletter: demand.

He did this by playing 3D chess in his pre-launch strategy. You see, Eli could have started a general newsletter on e-commerce, or even niched down into growth. But, he could see that those markets were oversaturated. Instead, he chose to lay claim to some free real estate: customer experience and retention.

“What gave me any success that I have in the industry was choosing a niche that's not heavily oversaturated. So many people are focused on a broad topic like growth. It'll be hard to get sponsors because you're competing with 57 other growth newsletters. You need to be somewhat niche in order to create a space. If somebody has a tool that's related to retention or customer experience, which other newsletters are they sponsoring?”

“If you want to talk to CX leaders and managers and retention-minded people, the niche way is so important. People are terrified of niche, but the sponsors are probably paying me a lot better based on my [subscriber] count versus somebody that has a 100,000 broad audience [subscribers].”

“I get that pushback all the time, where I'll talk to a sponsor and they're like, ‘That's very overpriced. You have 7,000 subscribers. We paid that to somebody with 30,000 subscribers.’”

But, Eli isn’t phased by sponsors who are concerned about the price he charges for a placement in his newsletter. “I’m not struggling because I'm talking to retention brands that want to advertise a retention app. I have a list of people that I've said ‘No’ to because I was fully booked. I book a quarter in advance, and it's always fully booked on the sponsor side because it’s a very niche audience.”

“I’m talking to exactly the people I want to talk to with a 55% open rate—a very niche audience about a very niche topic. On a practical level, building niche was actually much smarter for me than going broad because everyone's broad.”

Eli shared his advice for anyone in the ecommerce space thinking about starting their own newsletter: niching down is best. And even within a micro niche, you can still differentiate yourself.

“People worried about competition—if you're talking about ecommerce, there are a thousand ecommerce newsletters. When you're going niche, you have less to worry about, because even if somebody writes about customer experience (and now there are other customer experience newsletters), most of them are geared towards how to outsource or how to use a BPO. I'll never talk about that because I don't do that.”

“Even within the niche, there are niches. The best move I've ever done is to go niche.”

“When I started talking about CX, 95% of people in CX weren’t talking about it on the internet. They're quiet, they're introverted. They're doing it… in the corner. There are not a lot of voices in CX. It’s really easy to get attention when there's nobody making noise in a space. The voices in CX are 75 years old. There are no young voices here.”

“I think that as I’ve started talking a lot, we're seeing other people that are becoming CX influencers, which is so amazing. I'm consistently looking to elevate other people in CX because we need more voices. It's not a competition.”

Using CX Principles to Sustain Growth

When it comes to growth, it’s one area where Eli intentionally hasn’t set a goal. While most newsletter creators have specific subscriber targets to hit, that’s something he’s intentionally chosen not to do. Instead, he’s looking to keep focusing on the value he’s providing his audience by creating quality content.

“I think I'm one of the very rare people in the beehiiv ecosystem that's not insanely focused on growth. I’m really focused on sustainable growth, which is a CX thing. I'm not a growth guy. I'm a retention guy by trade. I’m entirely focused on ‘How can I keep this insane level of quality, not outsource anything, and do everything myself?’ Everything I talk about in CX is how I've been building this newsletter.”

“Obviously it’s another stream of income. Yes, it helps me put my wife through school and cover childcare for my son. But, what's exciting for me is that this is my actual passion. I'm not ripping Wikipedia articles and turning them into newsletters. I'm obsessed with this process, and I think I'm probably the only newsletter operator that doesn't have a growth goal.”

“I don't want to have a hundred thousand subscribers. By the end of 2023, I want to make sure I sustain the quality. I just want to make sure that people are continuing to be interested in it and my quality doesn't dwindle.”

Eli’s main goal is simple: to stick to it. Success, to him, is continuing to hit publish consistently.

“I've never been consistent [with anything]. It’s always been so hard for me to do anything every single day outside my job. Writing for 40-something weeks straight, I haven't missed a week. It’s the most consistent I've ever been in my life about anything.”

“If I can do a year straight on a newsletter, that'll be my biggest win of 2023. I have a 9 to 5 job. I have a wife that's in med school. I have a kid that's almost two years old—so it's a hustle. My goal is like, ‘Can I make it to year one and then year two?’”

If you’re interested in learning from one of the leading CX and retention voices, Eli Weiss, you can sign up for All Things CX & Retention, or check out some recent newsletters, like The One Thing 95% of Retention Folks Miss, or The Hot Dog Moment That'll Change The Way You Think About CX.