Newsletter Circle is the newsletter for newsletter creators.

👉 Every Sunday, you will read the unique journey of a different newsletter creator and learn more about how to start, grow and monetize your own newsletter.

👉 Every Wednesday, you will read articles and the list of curated resources to level up your newsletter business.

🎙CREATOR INTERVIEW

Welcome to the second part of my interview with Tim Huelskamp about how they build 1440.

For those unfamiliar with 1440, it is a daily newsletter with over 3.3 million subscribers and a monthly influx of 200K+ new subscribers!

It is named as one of the biggest and fastest-growing digital media startups that ranked No. 79 on the Inc. 5000 list.

And it all started with an issue that they sent to 78 people.

Recently, I had the privilege of meeting Tim Huelskamp, the co-founder and CEO of 1440, on a video call. What struck me most, among many other things, was his down-to-earth approach and his commitment to giving back to the newsletter community. He consistently emphasizes that the success of 1440 is a collective effort, attributing it not only to his dedication but also to his co-founder, Andrew Steigerwald, and the entire 1440 team.

Last week, we covered how they hit the road and grew 1440 from 78 to 3.3+ million subscribers.

If you haven't read it yet, I highly recommend you start from there.

Today, you’ll discover:

• How the monetization strategy of 1440 evolved over time

• How 1440 defines and measures “success”

• What it really takes to build a company to sustainability

• Key learnings, challenges and advice to newsletter creators

• Tim’s favorite newsletters that he looks for every week

I feel incredibly honored to share the behind-the-scenes of 1440 with you.

Let’s dive in!

🏷 NEWSLETTER IDENTITY CARD

🛠 Tool Stack

• Internal Communication → Slack

• Meetings → Zoom

• Docs & Storage → Google Suite

• E-commerce → Shopify

💸 MONETIZATION

When and how did you start monetizing 1440? How did your monetization strategy evolve in time?

We started monetizing 1440 when we reached approximately 50k subs. 

Per my comments in the growth section, we wanted to “de-risk” the company before focusing on monetization. 

Once we had evidence we were delighting and retaining users, we then focused to see if we could grow the audience.

Once we de-risked/proved we could delight and retain users, and grow the audience, we then focused on monetization.

We looked to other trailblazing newsletters in the space and mimicked their strategies. One of the benefits of this space is you can see all their customers in the daily emails. We started outreach to forge relationships.

When we were smaller (~50k subs), we had many CPA/CPC deals to prove efficacy to our audience. As we scaled the audience, these disappeared and we moved to purely CPM or fixed-price deals. 

As an example, if you have 50k subs at $50CPM on opens, the placement is ~$1k.  This often isn’t worth the time of the larger brands who are seeking to deploy tens of millions of dollars per quarter. So as we increased in size, we became more appealing to larger brands.

We’ve become much more sophisticated as we’ve grown up, but at the end of the day we’re always working to delight our customers, by providing them with strong and consistent returns. It’s incredibly easy for a brand to just push the spend to Zuckerberg, so we have to delight them with strong returns and terrific customer service.

What is key to building successful partnerships based on your experience so far?

Are they seeking awareness, clicks, conversions? 

What is the goal of the partnership and how can we overdeliver to the partner, so they retain them as customers?

We also try to delight them with our customer service and be an asset to them in any way we can - including helping with landing pages, ad copy, etc. 

📈 PERFORMANCE MEASUREMENT

How do you define success for a newsletter business?

First, are our employees happy, healthy, and engaged? Nothing else matters if we don’t have a world-class, happy team. 

Second, are we delighting our readers? Without readers who love our product, the business model breaks down. 

Third, are we delivering for our partners?

I could list dozens of supporting data here, but it really boils down to those 3.

To build on the above, what are the most critical metrics that you track?

I’d summarize this in 3 buckets.

People
We run employee happiness surveys where everyone scores a handful of key questions on how they’re feeling about life and growth at work. We also track employee retention, we haven’t parted with an employee in 3 years.

Delighting users/growth

• Open, Click and Retention rates = Are we delighting and retaining the user? Is our list growing each week?

• CPA (including CPM, CTR, CVR) = Are we attracting new users efficiently?

• LPO = Is our CVR improving?

Delighting our partners/revenue 
Partner rebookings/retention rate, are we growing revenues each month, are we growing CPMs, is our pipeline of new clients growing?

We have a host of other metrics: social growth, finance, etc but we like to keep things simple and it really boils down to the buckets above: build a world-class team, write the best product in the space, and monetize and grow our audience effectively.

🎢 NEWSLETTER EXPERIENCE

How did building the 1440 newsletter contribute to your life professionally and personally?

How much time do we have here, Ciler? :)

I consider myself a lifelong learner.

One of the most rewarding aspects of being a CEO is the dynamic nature of each day. Every quarter, me and my team are working on new challenges. In the beginning, it was MVP product, initial scale and monetization. Now it’s more team-building, strategy, partnerships, product R&D, scale to tens of millions, etc.   

Everyone on our team seeks to grow and wants to be challenged. Our collective journey is an ongoing learning experience, contributing valuable insights to our personal and collective knowledge banks.

We also love we’re able to build a brand that shares knowledge and helps the world be a smarter, more interesting, more fascinating place.  

I’m so grateful for the relationships I’ve forged, specifically with my colleagues - we all learn from each other every day. 

It's mind-blowing to build such a successful media business from scratch. During our previous chat, you mentioned that many people, especially in the beginning, helped you, and now you want to give back. We've been observing that some founders lose their way after achieving significant success. 

How do you manage to maintain your humble approach and a “giver” mentality, as Adam Grant named it?

I’ve been amazed throughout my life, by how many people have gone above and beyond to help me grow as a colleague and human. It reminds of of a quote from my favorite book, The Alchemist:

“And, when you want something, all the universe conspires in helping you to achieve it”.

Our newsletter space is incredibly, incredibly collaborative - everyone works to help each other grow personally and professionally.

I try to return the favors I received, by helping others however I can. 

I end every episode of podcasts with an offer for others to reach out to me directly with any questions (same here: [email protected] - I’ll respond).

If you reply to 1440’s daily email, I read every message and respond to nearly every email.

I’ve learned quite a bit from the folks on the other end of the outreach and built incredible relationships.  

What is the most challenging part of running a newsletter-led media business and how do you handle it?

The most challenging part of running a newsletter-led media business is hiring the smartest people in the world on your team and keeping them happy.

We hire brilliant employees to work on projects they’re incredibly passionate about. We've implemented various measures, including minimizing meetings, establishing clear work/life boundaries, conducting happiness and wellness check-ins, and providing above-market compensation and equity upside.

📌 ADVICE TO ASPIRING CREATORS

What would it be if you had the right to give one piece of advice to aspiring newsletter creators who want to build a successful newsletter business?

Focus on understanding and delighting the user and nothing else. 

I meet quite a few founders in the space who ask for monetization and growth strategy guidance but have engagement/open rates which will lead to long-term business failure. 

And then once that happens, see the above guidance on building a world-class team.

💜 FAVORITE NEWSLETTERS

What are your favorite newsletters that you can’t wait for the next issue? 

• Newsletter Circle - to keep me apprised of the inspiring builders in the newsletter space

• Newsletter Operator by Matt McGarry - the best round-up of what’s happening in the newsletter world

• Lenny’s Newsletter by Lenny Rachitsky - incredible product/growth advice, ex-Airbnb product/growth 

• Founders by David Senra - it’s a podcast at heart, but there’s also a newsletter - he summarizes biographies of history’s greatest founders, fascinating content; highly recommend

👋 FINAL WORDS

First, thank you so much for the opportunity to share our team’s story. We’ve worked incredibly hard to get here, and we appreciate this opportunity to pass on what we’ve learned - in hopes of helping others on their journey.

I came from the private equity world, and had so many advantages in starting off, and there were numerous times when we almost didn’t make it. In fact, we may still not make it if our team doesn’t deliver every day to our readers and partners.

Building a company to sustainability demands far more grit, and time/effort than most anticipate, probably by an order of magnitude if not more.

My brilliant co-founder Drew woke up at 4 am every day before his full-time job for ~2 years (while raising an infant!) to ship our product every day when we had 5,000 subscribers. Do you believe in your vision/product as much as Drew did?

If I can help in any way, I’m at [email protected]

🔗 Where to find 1440

• Facebook w 508K followers

• Instagram w 398K followers

• Twitter w 137K followers

• Reach out to Tim Huelskamp → [email protected]

👉 Do you want to reach 1,900 newsletter creators & enthusiasts?

ICYMI - The Latest Newsletter Circle Issues

• 1440 by Tim Huelskamp & Andrew Steigerwald - Part 1

  “We started by sending a minimum viable product (MVP) to 78 friends and family. We ourselves had the pain point, but we wanted to confirm others also craved the service."

• 7 Biggest Challenges Newsletter Operators Face

  34 newsletter creators shared what they struggle with the most

• The Follow Up by Nic Conley

  “If I were starting over and trying to grow strictly through organic social, I’d go with Instagram.

  Reels are super shareable, and people tend to check out your profile page more than any other platform.“

That’s all for today. Thanks for reading and don’t be shy to hit reply if you want to reach out to me.

See you next week.

Ciler