Newsletter Business Spotlight:

The Newsletter Conference 2024

The Newsletter Conference hosted its inaugural event on May 3, 2024. Hosted by Who Sponsors Stuff, this event brought together over 400 newsletter operators and service providers to focus on the current and future state of the newsletter industry, which was explored in detail by 8 panels of newsletter industry experts.

Newsletter Business is a proud promotional partner and participant in the event, and has invested many hours to curate this exclusive spotlight on the conference, curating 5 or more key insights from each session to share with our subscribers based on what we think is most valuable to your newsletter-driven business.

Dan Oshinsky (Inbox Collective)

25 Rules For Running A Newsletter In 2024: Dan Oshinsky of Inbox Collective shared 25 rules for running a newsletter in 2024;

  1. Email is an owned channel, but ownership belongs to the audience.

  2. Have a clear audience for your newsletter.

  3. Understand the job of your newsletter.

  4. Use AI for productivity, not creativity.

  5. Be willing to go where others aren’t.

  6. Some topics are at “peak newsletter”…we don’t need more newsletters on these topics UNLESS you can conceive of a B2B use case for these topics, as these topics usually appear in a B2C context:

    • How to use AI

    • Crypto investing

    • News in 5 minutes

    • 5 things I read this week

  7. Identify 1 new way to make money every year.

  8. Make your choice: Hyper-scale or Hyper-niche ie. go big and broad or deep and narrow.

  9. Only ask for a reply if offering something in return.

  10. Win back inactive subscribers or let them go.

  11. Operate in all 4 growth quadrants:

    • Owned: Email, SMS, website, landing page, etc.

    • Earned: Attention based on relationships or content

    • Algorithmic (or Rented): Social or search platforms

    • Paid: PPC ads, Sparkloop, beehiiv boosts, etc.

  12. Start collecting more subscriber data than just an email address.

  13. Look outside newsletter industry for inspiration.

  14. Launch fast, then make things better.

  15. Be willing to sunset what’s not working.

  16. If you see an idea work elsewhere, test it yourself.

  17. Find an accountability partner.

  18. If you act like a spammer, you are a spammer.

  19. No one knows your audience better than you do.

  20. Accessibility is not optional.

  21. Your “perfect” sits at the intersection of 3 things:

    • What you believe

    • What your audience says they want

    • What your audience actually does

  22. Direction is more important than speed.

  23. Don’t rely on silver bullet metrics.

  24. Focus on content and relationships.

  25. There is no path but yours.

From left: Elana Zak (Washington Post), Brad Wolverton (Hubspot), Nicole Casperson (Fintech is Femme), Neal Freyman (Morning Brew)

Steal This Newsletter - Lessons on Great Content: A panel of seasoned operators from the Washington Post, Hubspot, Fintech is Femme and Morning Brew shared their views on what makes for compelling newsletter content, including the importance of clear newsletter value proposition, having a unique perspective, and sharing habit forming content:

  1. The battle for the limited attention of your readers is key; your competition is Taylor Swift and any other distraction, not just another newsletter. The consensus was to keep content short and scannable. 1200 words or less was mentioned a few times, with guidance that you could have a single 300 word article and then a few short ones. Readers value brevity but don’t care how many articles overall, so experiment and pivot until you find what works.

  2. Your newsletter’s value proposition is a function of the distinctive perspective it shares with your audience. For example, that might include a specific gender’s take on an industry or distilling the meaning of broad news or trends to the niche you serve.

  3. Your newsletter’s perspective will be informed by the talent that produces your content, as well as how well you know your audience. You should regularly survey your audience seeking to learn the 1 thing they really want (not 5); use forcing functions to restrict answers, but also allow a few open ended questions. Zoom focus group calls with readers to see how they really consume your newsletter will help (and be humbling too). Make your reader feel like your newsletter content will make them look good to the key stakeholders in their lives (bosses, etc.)

  4. The inclusion of habit forming content elements is incredibly important. This is often the content that gets people to open your newsletter on a regular basis. These can be memes, productivity tips, playlists, animal videos, or profiles of successful people the reader aspires to be…anything that repeatedly captures the attention and interest of your reader that doesn’t necessarily have to be related to your newsletter’s theme. Certain formats and verticals give more latitude to be quirky or different; B2B for example moves slower and allows you to take time to analyze news in a value-added way vs. break it.

  5. Newsletter voice and format can be somewhat dynamic elements. Style guides are helpful but it is important to let writing staff be themselves. Voice can change as a newsletter evolves, and the audience can grow up with the newsletter operator which strengthens their bond. Visually rich formats for newsletters can work well; Brad modeled his newsletter Newsletter Examples after Marketing Examples. It’s also possible to vary format by day if sending daily or several times per week. Gamification is highly desirable for engagement if you can work out a relevant and entertaining mechanic.

From left: Dan Oshinsky (Inbox Collective), Stephanie Talmadge (Boardroom), Louis Nicholls (Sparkloop), Chenell Basilio (Growth In Reverse)

How To Grow Your Newsletter: A panel of experts from Inbox Collective, Sparkloop, Boardroom and Growth in Reverse shared their experiences growing their newsletters using a variety of methods such as contests, paid ads and referrals and emphasized the importance of knowing your payback period:

  1. Channels of growth vary widely in effectiveness. Contests, giveaways and sweepstakes can be a method of instant gratification for a quick hit of subscriber growth, however subscribers acquired this way rapidly become disengaged to the point where only 20% may ultimately convert as you wish. Large percentages (30+%) of subscribers acquired from paid Facebook ads may also not engage, but the economics of that channel often still make it worth it. Great content and relationships are cornerstones of growth. Recommendations from other newsletters (paid or organic) are often the highest quality. 

  2. Growth can be influenced by whether your newsletter would be classified as habit forming or value delivery. Habit forming newsletters tend to be daily and reinforce behavior through frequent delivery of addictive or immediacy-based content. Value delivery newsletters have lower frequency such as weekly or twice per week, but compensate for that lower frequency at the outset of the relationship with the use of a welcome email sequence.

  3. Referral programs have evolved and merch-based incentive rewards are not as attractive these days as they were at the height of Morning Brew’s growth. If you ask your subscribers to share your newsletter without an incentive, introducing a referral program will just amplify the non-incentivized referral rate, not transform it wildly. You must figure out the incentives that will motivate your subscriber base, such as:

    • A community section that features the subscriber’s newsletter if they generate a certain number of referrals.

    • If you open and click on every newsletter issue in a month, you get entered into a giveaway (more loyalty than growth tactic).

    • First person to click on a newsletter issue gets a prize, as does the 50th, etc.

  4. The things you do for a subscriber before they even read one issue are important. Establish your identity as the author in the welcome email series and invite replies, which will often come. Tease each issue of the newsletter to your social media audience the day before an issue is published.

  5. A rapid payback period is key to growth, and ideally you want to be able to monetize or payback the acquisition of a subscriber within 14 days for rapid growth. Understanding your subscriber lifetime value (SLV) is also key. Paid recommendations of other newsletters via platforms such as Sparkloop or beehiiv can help you accelerate payback; B2B audience recommendations typically pay $1.50 - $3 per subscriber whereas broad or international audience recommendations could be $.50 - $1. Your rate of growth is dependent upon your goals; sometimes ad rate thresholds will motivate you to hit certain subscriber volumes, but be mindful that fast growth also comes hand in hand with churn.

From left: Jacob Donnelly (A Media Operator) & Adam Ryan (Workweek)

The Opportunity In B2B: Jacob Donnelly of A Media Operator & Adam Ryan of Workweek addressed the many opportunities that abound within the B2B newsletter arena and the strategies needed to unlock them:

  1. As in all sectors, not all B2B audiences are created equal. Doximity serves the one million doctors in the US and represents a $4 billion business opportunity; Workweek’s focus on healthcare strategists might mean there are only 5,000 ideal customers to serve and therefore the opportunity might be $10 million. Who do you want to serve, and for how much?

  2. Monetization choices seem fairly common for newsletters across B2C and B2B markets, however B2B markets often have deeper pockets:

    • Ads / sponsorship

    • Membership / subscription

    • Events

    • Lead generation (affiliate or pay per lead)

  3. B2B markets where trade associations are dominant players are great opportunities because they help to quantify the opportunity and are also usually stuck in an analog world that cannot compete easily with a digital-first strategy. However, B2B customers also move at a slower pace, and often will want information less frequently and sometimes (gasp) in magazine format. Sales to B2B customers can also take longer.

  4. Events work well in the B2B arena but are subject to industry cycles and require a balanced approach; use an array of smaller events to funnel interest into fewer large events. Smaller events are a great vehicle for creators.

  5. The hot take in this session was to be very careful with and possibly altogether ignore using paid newsletter recommendations, otherwise known to those of us OG newsletter and email marketers as co-registration or co-reg. The argument is that if you write the best newsletter in your space, why should you feed your competition subscribers for a few dollars a head? There is also a consideration with respect to the fact that subscribers often choose multiple newsletters at once when presented with recommendations, and therefore don’t really care that much about any of them which means churn is likely. Platforms in the space obviously love paid recommendations because their revenue models are built on charging for the number of subscribers a newsletter has, and therefore they have an inherent conflict of interest.

From left: Boye Akolade (The Future Party), Jenny Rothenberg (Smooth Media), Jesse Watkins (Who Sponsors Stuff), Greg Van Horn (FinanceBuzz by Launch Potato)

The Future of Newsletter Advertising: A panel of advertising gurus from The Future Party, Smooth Media, Who Sponsors Stuff, and FinanceBuzz broke out their crystal balls and made bold predictions that addressed the performance nature of advertising, what audiences want, and how to differentiate in a crowded market:

  1. Advertising will continue to be increasingly performance-driven with an emphasis on CPC deals. The opportunity to negotiate stronger ad deals will largely depend on whether you serve an audience that can’t otherwise be reached easily, and how creatively you craft your strategy to align with the brand’s goals.

  2. Advertising will get more niche-specific; this is a necessity as newsletters themselves get more niche-specific in their content and audience focus.

  3. The audiences that newsletters advertise to want to be passionate about something; they already do and will continue to care a great deal more about individual creators than faceless brands.

  4. Differentiating your newsletter’s offering to advertisers will require operators to have a more intimate understanding of advertisers such as where their metrics need to be and what their copy and landing pages look like. This knowledge, coupled with creatively integrating ads into the newsletter’s content, will be essential for success. For example, working with a brand to develop 101-level content for your audience is a strategy.

  5. The onboarding experience of The Assist was cited as a superior example for how to achieve monetization and brand marketing.

From left: Dan Oshinsky (Inbox Collective), Ashley Hoffman (The Philadelphia Inquirer), Ryan Heafy (6AM City), S. Mitra Kalita (URL Media)

The Newsletter Saves Local News: A panel of experts from Inbox Collective, The Philadelphia Inquirer, 6AM City, and URL Media provided insights into the local newsletter landscape and some of the unique challenges and opportunities it affords:

  1. Membership models can prove challenging if scaling the local news model across multiple geographies. The need to customize each membership to fit the community being served becomes resource-intensive and is hard to offset with the finite number of paying subscribers in each locale.

  2. Government/community contracts and grants for local newsletters represents a real monetization strategy as many local governments have set budgets for community outreach.

  3. Educating ad buyers in local markets is a time-consuming obstacle, as these are the same buyers who often had deep personal relationships with their other legacy media channels.

  4. Legacy media had a habit of giving away newsletter ad inventory as an afterthought in larger advertising bundles, and as such it makes it hard to charge for something that was previously offered for free.

  5. Reporters are finding that the inbox relationship with the communities they serve is helping them with their reporting.

Jack Appleby (Future Social), Erika Burghardt (1440), Lucy Keller (Bloomberg Media), Aine Stapleton (International Intrigue) and Matt McGarry (GrowLetter)

Top Tactics To Grow Your Newsletter: Growth is clearly a concern for newsletter operators, and to meet that need a second panel of growth rock stars from Future Social, 1440, Bloomberg Media, International Intrigue and GrowLetter shared their tips, tricks and strategies regarding which growth channels to focus on:

  1. Meta is the platform that is the recipient of the majority of recommended ad spend, accounting for 65-80%. Modest growth campaigns can be supported for $50/day on the platform. The remainder of the ad spend was focused on Twitter, LinkedIn and sponsoring other newsletters. Newsletter sponsorship can yield 2-2.5x more engagement than other paid ads, but was much harder to scale.

  2. Look at the long-running ad creatives being used by other newsletters to gain insight and inspiration for your ads. UGC ads/video tend to work best for authenticity, as do motion graphics (text on screen, video in background). The Facebook ad library is a great source of reference material.

  3. Most newsletters are not doing enough testing of different channels or ad creative, particularly based on knowledge of their audience. Meet your audience where they are at, and reduce friction for them to engage.

  4. Twitter and LinkedIn both represent great growth opportunities. Take one of your issues and use the individual articles to feed 5 or more social posts on these platforms; the goal is to tease users on these platforms to get interested without revealing all of your content to non-subscribers. Be sure to post in advance of your next issue as well to build interest. LinkedIn has its own version of on-platform newsletters, and the first one you publish will get a lot of attention as all of your followers and contacts are notified. Use these LinkedIn newsletters to also tease your content but drive to your email newsletter.

  5. Memes represent very cost-effective growth channels as they are not valued the same as other formats and so deals are available. Target meme channels that are downstream of your topics (ie. international politics audience is also interested in history usually) and work with the meme creator to shout out your newsletter on their stories. Ideally try to create the content for the channel if you are able as the creator may not get your brand, and control the budget carefully.

From left: Ryan Sager (Who Sponsors Stuff), Jacob Donnelly (A Media Operator), Rachel Schindler (Punchbowl News) & Ari Lewis (Payload & Ignition). This group was so dynamic I could only capture them in motion. :)

Put Your Business Model At The Center of Your Strategy: This panel of newsletter business strategists from Who Sponsors Stuff, A Media Operator, Punchbowl News and Payload & Ignition shared their perspectives on different revenue model options, the need for diversification, and whether we are experiencing a “bad newsletter” bubble:

  1. The trinity of monetization models used by all of the panelists were ads, subscriptions and events. Events in particular were heavily emphasized; Punchbowl ran 45 events in 2023 and Payload planned 14 this year.. Monetization of channels beyond newsletters, such as podcasts, is also a consideration and helps to reach a broader audience.

  2. This panel reinforced a key insight from the earlier B2B Opportunity panel, which is that the presence of prosperous trade associations are a good signal for a market and provide opportunities for newsletter operators.

  3. Diversification of revenue channels offers potentially greater growth and stability but also introduces a different class of operational risks and expense. Scale necessitates diversification, but also requires investment in specific talent and platforms to embrace new channels and product delivery requirements. This poses challenges to smaller, resource-constrained newsletter operators in particular.

  4. An opinion was shared by Jacob Donnelly of A Media Operator that if we are in a newsletter bubble, it is a “bad newsletter bubble”. His perspective was that the market has become crowded with newsletters focused on growth tactics rather than authentically serving a great audience with great content. These “bad newsletters” are poised to shake out of the industry eventually.

  5. Newsletters are among the easiest ways to communicate and serve content to an audience, and therefore represent a great top of funnel mechanism. For the channel to unlock its full potential, it is necessary for newsletter operators to engage their subscribers through polls and surveys to develop a deep first party data repository as the market shifts away from third party data models. It is particularly important to understand what company your subscriber represents and what role and function they perform.