Newsletter Circle is the newsletter all about newsletters for indie 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.

Hello everyone! After a short break, I’m back!

The new year has started and I know that each of you has different objectives for your newsletters in 2024.

No matter what your goal is —whether it's starting a new one, skyrocketing growth, boosting monetization, or simply maintaining it as a side project. 

I have some fantastic interviews, articles, and projects in the pipeline that both aspiring and seasoned newsletter creators can benefit from.

I've already hinted at some of the interviews scheduled for January and February in the post below. Check it out here and stay tuned for the actual names!

Is there anyone that you want me to interview? Reply and let me know.

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🎙CREATOR INTERVIEW

Have you ever come across a newsletter that is sold and reacquired by its founder after two years?

I know one.

The Water Coolest is a daily investing and markets newsletter that is started, sold and reacquired by Tyler Morin.

Currently, it reaches 130K subscribers.

The Water Coolest is more than just a business for Tyler. It turned into his exit ticket from the corporate world that he didn’t find any fulfillment and helped him get through one of the darkest times of his life.

In our interview today, he shared:

• How everything started with a blog and turned into a full-fledged newsletter-led business

• The evolution of growth strategies he utilized along the whole journey

• His key learnings from building, selling and reacquiring The Water Coolest

Tyler also mentioned that he rejected the job offer from Morning Brew just before starting The Water Coolest.

Life is shaped not only by our YESs but also by our NOs. And Tyler’s story shows us that saying no to the opportunities that seem great doesn’t prevent other great things from happening in life.

Let’s dive in!

🏷 NEWSLETTER IDENTITY CARD

🛠 Tool Stack

• ESP → Beehiiv

• Writing → Google Docs

• Planning & Task Management → Todoist

👋 MEET THE CREATOR

Welcome Tyler. Let’s start with getting to know you.

I grew up in Connecticut and went to UConn. I lived in NYC for a few years working in financial services consulting… and absolutely hated it. That was one of the reasons I started a blog, which end up becoming The Water Coolest. 

The Water Coolest is a daily investing and markets newsletter written in a super irreverent voice that’s certainly not for everyone. I sold it to Barstool Sports in 2021 and was able to reacquire it late last year.

Now, I am running The Water Coolest and helping other people build awesome newsletters with leverage letter (a newsletter consultancy and agency).

🥁 START

You have a unique story where you saw almost every aspect of running a newsletter business. You built, sold and reacquired it.

Let’s go back to 2017. How did you decide to start The Water Coolest in the first place?

It was a bunch of things that came together at the right time…

Well, I was working in financial services consulting, and I absolutely hated it. I read a lot of financial news sources (Bloomberg, CNBC etc.) to keep up with my clients. I always thought there should be finance and business news content that was written the same way I talked to my friends at the bar (unfiltered, irreverent). 

And in 2014, I started a blog called Entry Revel. I was writing about everything a 25-year-old corporate American cared about: Sports, dating, stupid stuff I saw on LinkedIn, etc.

And NOBODY was reading it.

Then, I started sending links to the blogs out via email just to friends and family. And more people started to read. I realized it was a whole lot easier to send emails than figure out SEO, social media etc. 

At the same time, I heard about the Morning Brew and the Skimm was blowing up. 

All these things came together and I came up with the idea for The Water Coolest.

Interestingly, right before I started The Water Coolest, I actually applied to Morning Brew and got a job offer from them to be employee 3 or 4 or something like that. They were still in an NYU incubator. Unfortunately, the money at the time wasn’t right and I was interested in making more irreverent content whereas they had a vision for more of an educational newsletter at the time…

Anyway, I launched TWC on September 12, 2017 (we didn’t launch on Monday, September 11th, because it felt weird to start on 9/11). 

🚀 GROWTH

You have a huge list with over 130,000 subscribers. How did your growth strategy evolve in time?

We did some work with @GSElevator, which was a hugely popular account on Twitter at the time.

And then, we worked with some of the Instagram Finance Meme accounts before they got massive, like Liquidity and High Yield Harry. 

From there, we tried pretty much everything because, as everyone who has grown a newsletter knows, scale is not easy when you’re fighting attrition.

We ran Facebook and IG ads, did giveaways with other brands, cut co-reg, dealt with a few different players in the space like Dealbreaker and Wall Street Oasis, started a college ambassador program, launched a referral program, etc.

Which growth channels do you mainly use currently?

I have a really awesome core audience who loves to spread the word to anyone who will listen.

I have plans to ramp up paid social spending in the coming weeks.

🤝 THE EXIT AND REACQUISITION

SELLING IT TO BARSTOOL SPORTS (2021)

In 2021, you sold The Water Coolest to Barstool Sports and took a role as  Head of Newsletter Ops.

Why and how did you decide to sell it?

I actually didn’t really have any intention of selling it at the start of 2021. I got to know Large from Barstool (who I’d end up co-hosting a podcast with) because he was a reader of the newsletter.

During COVID (summer of 2020), he was doing a podcast called Mind Your Business. He was talking to people who had shifted their business model to survive during COVID (think: pizza parlors selling pizza-making kits).

I reached out and told him that I was launching a paid newsletter since ad dollars had dried up. He immediately reached out and asked me to come on. I think he just wanted to talk finance since he was a former trader. Then he asked me to come on again to talk about GameStop and crypto (fun fact: SBF was on that podcast, too) in early 2021.

To promote both of those podcasts, he posted a blog with the pod and a link to the newsletter. Both times, I got a few thousand new subscribers. And it made me realize I needed to shift ad dollars away from Zuck and to Barstool.

So, I reached out to [email protected]. Within a few hours, I was on the phone with the COO, who would end up being my boss. I think he monitored the ad inbox.

It just so happened that Barstool was looking to get into the newsletter game and Dave was doing Davey Day Trader at the time, so finance was a big initiative internally.

How did you make the valuation?

It was simple, really. We based it on a multiple of revenue.

BARSTOOL SPORTS DAYS (2021-2023)

How was your experience at Barstool for ~2 years? How was it different from running it as a solopreneur before the exit?

It was awesome. Barstool was the only company I wanted to sell to. It was a dream job. 

Going from being an entrepreneur to an employee was pretty easy because Barstool was so entrepreneurial. Nobody ever edited a word of my newsletter. I had full control over content and growth. And I had a world-class sales team supporting me. Plus, all of the behind-the-scenes stuff I hated doing was taken care of (finance, accounting, etc.).

REACQUISITON (Oct’23)

Then, you reacquired The Water Coolest after running it as Head of Newsletter Ops at Barstool for ~2 years.

What are your biggest priorities currently? 

What do you plan to do differently this time compared to the period you ran The Water Coolest before it was acquired?

I plan to optimize for metrics that matter.

Before Barstool, I had no “real” media experience. I was just kind of figuring it out on the fly. But at Barstool, I got to peek behind the curtain and see how a real media giant runs.

Based on your experiences during 3 phases in your newsletter journey (before selling it, during Barstool Sports and after the reacquiring TWC), what advice would you give to newsletter operators who aim for their newsletter to be acquired?

My biggest piece of advice to anyone looking to sell any business that they run and have built is to make sure you’re prepared personally.

🧩 SYSTEM & PRODUCTIVITY

You have a lot on your plate for a one-person business. You curate news and create content for each weekday, you write a deep dive for paid subscribers and you manage all the operational stuff, like selling ads. You also recently launched a content agency & newsletter consultancy service.

How do you make it work? 

There isn’t a lot of sleeping going on (which, luckily, I’m used to because I have a 1 and 3-year-old). Lots and lots of caffeine currently. At this point, my writing is the easy part since I’ve been doing it daily for almost 7 years.

🎢 NEWSLETTER EXPERIENCE

How did building The Water Coolest contribute to your life professionally and personally?

The Water Coolest (well, technically, what came before it) helped me get through one of the darkest times of my life. My dad killed himself in 2013, which was certainly pretty brutal to live through. Starting the blog that preceded The Water Coolest (Entry Revel) in 2014 was an escape from everything going on. Plus, the whole situation gave me a not-so-friendly reminder that life is short, and you need just start doing that thing you’ve been putting off.

Thank you so much, Tyler. Can’t wait to see what’s next in The Water Coolest's journey!

🔗 Where to find Tyler Morin and his work

• e-mail

• X → Tyler Morin / The Water Coolest

• LinkedIn

• Instagram

• Youtube

• Tiktok

👉 Do you want to reach 1,800 newsletter creators & enthusiasts?

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