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We recently published a deep dive on the newsletter industry. The feedback was very positive, so we decided to highlight more practical tips for growing a newsletter business.
In this interview, we talk to Harry Dry, who grew Marketing Examples to 20k+ subscribers in one year with zero funding.
His weekly newsletter is a 2-minute read that highlights case studies and actionable tips from real startups.
In this Q&A, you’ll learn:
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In June, 2020, we wrote about an emerging opportunity in custom decorative skins for video game consoles. In that article, we mentioned one major player in the space, Skinit.
We were quickly surprised to learn that the original founder of Skinit, Mike Stemple, was actually a member of the Trends community.
Stemple, who has had 5 successful exits, and is Director-Emeritus at The Founder Institute and a mentor at Techstars, met with us to talk about his time starting and running Skinit, and offered up the following advice to founders looking to get into any industry:
At the very least, brands should have awareness videos, promotional videos, and retargeting videos.
These videos should appeal to your largest buyer persona.
Awareness video
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Bob Pittman — the creator of MTV, former CEO of Six Flags, Time Warner, AOL, and Century 21 Real Estate and now current CEO of iHeartMedia — has had a hell of a career.
With an incredible background in the media business, Pittman turned heads in 2003 when he launched Pilot Group. The new venture was an incubator and investment fund for a business that many people wouldn’t have expected a media tycoon to get involved in: newsletters.
Trends readers have long expressed an interest in the nuts and bolts behind the newsletter business. This report will give you a behind-the-scenes look at how it works.
By doing so, we’ll answer why Pittman (along with thousands of other entrepreneurs) have flocked to this simple — but surprisingly profitable — business model.
In 1996, Microsoft released Internet Mail and News 1.0, a feature for its Internet Explorer browser. This was later renamed Outlook. That same year, other companies like Hotmail started offering free email services that could be used anywhere. And email was born.
Since then, email has become embedded in our culture (75%+ of US adults have an account).
In those early years, companies primarily used email as a way to send marketing material.
However, when Pittman entered the industry, he changed the perception of email. Specifically, he showed that email newsletters can be a standalone business.
Pittman & The Pilot Group
In December of 2003, Bob Pittman acquired DailyCandy, a trendy daily email for young women that featured tips on everything from restaurants and nightclubs to sample sales and beauty finds.
Pittman paid $3.5m for the business. At the time, DailyCandy consisted of 200k subscribers and a brilliant editor/founder named Danielle Levy.
The plan behind Pittman’s investment, say sources familiar with his strategy, was to help transform DailyCandy from a newsletter into a multimedia player that could extend its brand into magazines and books, stand-alone television shows, and perhaps even shopping or restaurant guides.
Over the next 5 years, DailyCandy went all-in on email. By 2009 the company grew to 2.5m subscribers and, according to Pittman, $25m in revenue with EBITDA of over $10m. That same year, Comcast acquired DailyCandy for $125m.
Following the acquisition, Pittman launched The Pilot Group, an incubator dedicated to launching DailyCandy for other verticals.
Pilot’s companies included Thrillist (now a $500m media company), PureWow ($25m in revenue before it was acquired for $40m), Business Insider (sold for $500m), and dozens more.
Most recently, individuals such as Ben Thompson (Stratechery) and Bill Bishop (Sinocism) have proven that single-person newsletter operations can generate 7-figures in annual revenue.
Furthermore, new media companies built through newsletters are generating healthy 8 figures in revenue:
A salient example of the growing trend in newsletters is the rise of Substack. The startup provides tools for writers to write, distribute, build community and monetize newsletters. It raised $18m from leading venture firm Andreessen Horowitz and, since the start of the coronavirus pandemic, has doubled its readership and the number of newsletters.
Warren Buffet loved newspapers. They were predictable and profitable. But now they suck. In their place, newsletters have stepped in, with all the upside (low-cost, direct-to-consumer benefits, with an opportunity to exploit many profitable niches) and little of the downside.
There are two primary business models in the newsletter business: ad-supported and subscription-based (see sample spreadsheet models here).
1. Ad-Supported (Examples: The Hustle, The Skimm, Axios)
For ad-supported newsletters, the key metrics include:
And key ad types include:
The sample ad-based model below looks at the monthly revenue for a newsletter sent 5 days a week with the following assumptions:
Based on these assumptions, the monthly ad revenue for this newsletter is $50k / day and ~$1m / month (5 days per week x 4 week = 20 days).
2. Subscription-Based (Examples: Stratechery, The Athletic, Trapital, 2PM, Trends, The Information)
A DIY subscription-based newsletter typically works in the following manner:
Stratechery, written by Ben Thompson, is a tech and business strategy newsletter launched in 2013. The content business provides one free weekly report and three additional pay-walled reports a week.
While he has not confirmed his subscriber count in a number of years, internet sleuths pin Thompson’s paying subscribers at a minimum of 25k, each shelling out $100-120 a year.
These estimates provide Thompson’s revenue figures and we can back out his expenses (tools he pays for) from the Stratechery Privacy Policy page.
Based on this fairly rough guesstimate, Thompson brings in revenue of $3m with a stellar 90% pre-tax profit margin ($2.7m net profit).
(You can change Stratechery subscriber assumptions here)
3. Substack Subscription-Based (Examples: Sinocism, Petition, TrueHoop)
Another subscription-based newsletter option for creators is Substack. As seen in the Stratechery example, a newsletter entrepreneur needs to be familiar with a number of tools (membership, forums, payments, content delivery networks, hosting, etc.) to successfully operate a newsletter business.
Substack has created a platform that offers a turnkey solution for these back-end services for creators (thus, allowing them to focus on content creation):
For those wondering “when is it a good time to monetize“, Substack has a great article based on the platform’s data (You’re Guide To Going Paid); the article is well worth reading and here are some notable bullet points:
Additionally, to make the subscription more appealing, here are some functionalities that Substackers offer:
In addition to Substack, there is an alternative “newsletter-as-a-service” platform called Ghost. The firm charges $29/month for its services and takes no transaction fee.
And, of course, there are more traditional mass email sending platforms (Mailchimp, Revue and Convert Kit) which have increasingly more “newsletter-as-a-service” functionality.
Additional Considerations For DIY Subscription vs. Substack:
While Substack provides a turnkey solution, the platform has a number of notable limitations for those looking to rev up paid subscription businesses:
Mass Adoption of Email
There are 3.9B active email users in the world, as compared to 3.5B social media users. Annual growth in email users is projected at a steady 2-3% over the next three years, bringing more end users into the email universe.
Better Engagement Than Social Media
In addition to the wide (and still growing) adoption of email, the channel has better engagement than the largest social networks:
Own Your Distribution and Relationship With Readers…
Late last year, the entrepreneur and investor Naval Ravikant tweeted that “building a following on Twitter is building a castle out of sand.” Large tech platforms such as Facebook, Twitter, Linkedin, and Google are famous for “changing algorithms” that can overturn the fortune of a media business overnight (e.g., Buzzfeed).
Because email is an open standard, when you build an audience via email newsletters, you directly own the relationship with the reader and are not at the whim of an algorithm change.
…Which Helps To Control Customer Acquisition Costs
Further, there is less of a reliance on paying Facebook (to get “boosted” on the news feed) or Google (to rank high in searches). While these ad prices have fallen during the pandemic, Facebook and Google ads regularly outpace inflation. Relying on them in the long-term is an expensive game.
Build A Community
The direct relationship with the end reader is also the perfect jumping point for building a broader community of like-minded people.
As 2PM’s Web Smith puts it:
Upsell and Cross-sell Opportunities
When you own a direct relationship with readers, you can sell additional products through the distribution channel:
Stable Medium
Related to the previous point, email is a well-established standard. It has not changed very much since its initial rise in the 90s. Moving forward, there will continue to be innovations in email clients (e.g., Superhuman, Hey), but the underlying standard is stable.
Lean Operating Costs…
As demonstrated by Ben Thompson’s Stratechery example in the previous section, newsletters can be an extremely lean business. A single individual writing expertly on a valuable subject can secure a high standard of living.
…With Opportunity To Ad On A Sales Team
While this may seem counterintuitive to the notion of lean operating costs, certain ad-supported newsletters can leverage sales teams effectively. Currently, there are no effective newsletter ad networks. A sales team with a good understanding of its audience and advertising can offer highly valuable contextual advertising that performs better than other ad options.
Ad-Supported
Subscription-Based
Subscription-Based (Substack)
Spam laws
The rise of increasingly stringent digital privacy laws (GDPR in Europe, CCPA in California, CAN-SPAM in Canada) has forced companies to closely follow anti-spam rules including: 1) user permissions; 2) honest headlines; 3) clear identification for ads; 4) opt-out options and more.
Very Crowded Space
Every major publication has a number of newsletter offerings (e.g., New York Times, Washington Post, WSJ). Further, with the rise of turnkey services like Substack, countless newsletters are being launched every day. The newsletter opportunity is as big as ever, but it’s very important to find the content gaps (more on that below).
Subscription Fatigue
As more written content goes behind a paywall (not to mention paid audio and video streaming services), there is concern that readers will develop subscription fatigue. In recognition of this issue, some Substack publications are bundling together their offerings so readers only have to make one purchase decision.
Limited Search Visibility
For subscription-based newsletters, the existence of paywalls means that the content is often hidden from search engine bots crawling the web. As a result, the content doesn’t show up in searches for relevant queries.
Difficult To Go Viral
Another related challenge is that gated content has a harder time going viral, as people are less likely to share items that hit paywalls.
Marie Dollé — a French-American digital strategist — put together a fantastic market map of newsletter-related products. We will touch on some of these categories below, but here is the graphic for inspiration:
Content Gaps (Particularly B2B)
There are countless content niches that could use a dedicated newsletter.
The B2B space is particularly ripe for disruption and offers high revenue potential as industry insiders will pay top dollar for analytics and insights (aka the “corporate credit card effect”).
As Petition — the Substack bankruptcy newsletter — shows, there is great appetite to give traditionally dry, industry-specific trade publications a more approachable voice.
A Google search of popular trade publications shows dozens of opportunities, including:
Curation, Bundling & Discovery Tools
As noted by Ben Thompson, whenever an industry goes from scarcity to abundance, there is great value in services that facilitate discovery and curation. Newsletter Stack is a recently launched platform that allows individuals to curate their favorite newsletter. Similarly, Substack’s internal discovery tool ranks the top paid and free publications.
Other discovery tools include:
We touched on the idea of bundling earlier and, in many ways, it falls under the “curation” umbrella. Packaging together complementary newsletters or writers into one package is an act of curation.
Here is more from tech and innovation consultant, Ari Lewis:
Paywall Services
One of the key decisions for any subscription business is to decide how much free content is made available.
Because of these varying strategies, there is an appetite for digital solutions that can register and subscribe readers as well as predict churn (or other related analytics) for paywalled content.
Piano is one such firm. But, based on the Trends team’s experience with the service, there is clearly an opportunity for a superior offering. (Message us if you have ideas!)
Newsletter Management
Management tools are needed to handle the abundance of newsletter. There are a number of solutions that curate newsletter feeds (Feedly, Newsletry, Feedbin) and newsletter reading apps (Stoop, Slick).
The Signal: One of our fellow community members recently pulled the data on 2.4k+ Kickstarter campaigns, and we dug through the numbers to see what projects are running successful campaigns during quarantine.
To identify these projects, we filtered the table for:
We also focused the list on physical products and filtered out tabletop games, which is traditionally a popular category in Kickstarter Land but less applicable for the Trends audience.
The COVID-19 pandemic has rocked each sector of the economy, but few realms have felt the effects more than education. With campuses closed across the US, preschoolers and PhD candidates alike are cooped up at home, trying to keep learning in the midst of the crisis.
Most students, teachers, and institutions are new to or relatively inexperienced with remote education. Before the pandemic, according to the latest available data, only 15% of US college students enrolled exclusively in online courses and fewer than 1% of K-12 students enrolled full-time in online schools — but suddenly, almost all students are taking classes entirely online.
Some lack the devices and internet connections they need to learn from home, while many teachers are struggling with digital systems they don’t fully understand. Plenty of schools and colleges scrambled to set up distance learning tools, only to be embarrassed when naked strangers Zoombombed classes.
The Signal: The quarantine period turbocharged e-commerce spend over the past few months.
To get a view on which e-commerce product categories are currently looking attractive, the Trends team asked ThoughtLeaders — a marketing intelligence tool — to provide us with data they’ve collected that will help you identify market opportunities.
ThoughLeaders tracks brand mentions across thousands of influencers on non-Facebook/Google ad channels, including YouTube, podcasts, newsletters, and blogs.
To identify which DTC brands have been expanding their ad footprint, we looked at direct-response ad tests across the aforementioned channels in Q2 2020 vs. Q2 2019.
Just over 3 months ago, Julia Cheek, the CEO and co-founder of Everlywell, appeared as a guest on our My First Million podcast. At the time, the coronavirus had just begun to spread to the United States, and her company — a 5-year-old startup that provides at-home medical testing kits and lab results — had no plans to produce an at-home test to detect COVID-19. She even laughed the idea off as a little crazy: “If we did, I don’t think I would be here right now,” she joked.
But within days of that conversation, Cheek and her Austin-based team were busy attempting to create a test. By mid-May — following a furious stretch of testing, initial government approval, and an unexpected turnabout — they became the first digital health company to receive FDA emergency use authorization for an at-home COVID-19 test.
The thought that a small startup would play such an integral role in responding to a global pandemic seemed incredible: “If there was ever a situation where a 90-person company had to be part of the national response to a pandemic, then there’s something wrong,” Christina Song, a senior Everlywell official, told us in a recent interview.
Each week, the Trends team curates the most actionable articles we can find into the Leads section of our weekly email. Below is a list, organized by topic, of all the best Leads from our first year (updated June, 2020). Let this be a resource you refer back to whenever you’re facing a new challenge in your business.
What companies are freezing hiring; what companies have laid off workers; what companies are still hiring; and who wants to be hired during the pandemic. Coronavirus job listings by company. 5 tips for reducing coronavirus business risk. How to Zoom like a pro. How startups should grow in 2020. A designer’s guide to pivoting in the pandemic. 10 ways to ensure your restaurant (or small business) survives the pandemic.
What companies will be hardest hit by the pandemic? How to apply for a small business coronavirus relief loan. How to stock up without getting ripped off. How to raise VC during the coronavirus. And how to work during a pandemic. How to respond to a disrupted supply chain. 8 creative coronavirus pivots.