If you had a chance to start over..

what would you do differently while building your newsletter?

Learn how to level up your newsletter from successful creators.

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I added this question to my interviews a while ago and asked ten successful newsletter creators so far.

Why?

Because, I believe it's crucial to reflect on what worked and what didnā€™t, the actions that we should have taken earlier and face our mistakes so that we can shape our next steps wisely.

Regardless of your list size or when you started your newsletter, you probably have a list of "I wish I could do this/that differently" items.

Sometimes, these turn into regrets.

But, our aim here today is to turn regrets into learnings.

What we've learned from the past will help shape today, the time that we have control over.

So, letā€™s take a quick look at what ten successful creators, who are at different stages of their newsletter journey, would change about the way they build a newsletter business.

ā

If you had a chance to start over, what would you do differently while building your newsletter?

  • Newsletter / Creator: The Ask by Ellen Donnelly

  • Launch date: Marā€™20

  • Subscribers at the time of our interview: 3,400

I would go bigger with networking, cross-promotions and interviews. Whilst they donā€™t always ā€˜convertā€™ subscribers, they build connections that one day turn out to be super valuable.ā€œ

A good example for me was Femstreet, the Substack newsletter/community run by Sarah Noeckel which I did some collaborations with in my first 6 months or so, and created a really strong pipeline of clients for me down the line. I didnā€™t do enough proactive outreach to other Sarahsā€¦but plan to be better at this going forward!

Ellen Donnelly - The Ask
  • Newsletter / Creator: Stacked Marketer by Emanuel Cinca

  • Launch date: Aprā€™18

  • Subscribers at the time of our interview: 60,000+ (Over 100,000 with two other newsletters acquired)

I would avoid mistakes and would have spent even more effort and resources on things that paid off, haha.

But to make a more concrete list of mistakes Iā€™d avoid or wins, Iā€™d want to be even more focused on:

- I would not sponsor any conference if the goal is to get newsletter readers. 

Maybe thereā€™s some format of conference that makes sense but what we tried was by far the worst cost per reader you can imagine.

- I would fire faster.

One thorough review and warning, and if things donā€™t improve thatā€™s it. No reason to drag it along, one bad team member drags down everyone significantly.

- Hire not just for skills but also for culture. 

Building on my previous point, work culture is way more important than I thought for a great team, itā€™s not just the hard skills for the role.

- Buy more ads in high-quality newsletters when you can get active subs for under $3. 

That opportunity doesnā€™t exist anymore and we could have done much more of it back in 2020.

Emanuel Cinca - Stacked Marketer
  • Newsletter / Creator: Email Magic by Greg Johnson

  • Launch date: Sepā€™23

  • Subscribers at the time of our interview: 1,600

I would do a better job of collecting more subscriber data on the front end so I would know how to best help them.

Greg Johnson -Email Magic
  • Newsletter / Creator: Open Source CEO by Bill Kerr

  • Launch date: Marā€™23

  • Subscribers at the time of our interview: 25,000

I would have started earlier.

Business in generalā€“like investing, like training, like relationshipsā€“compounds over time. I think of business as finding a way to add value to a market and then just not dying. If you are adding value, you will grow, and if you are growing, even if slowly, it will compound over time.

An example of that is Warren Buffet. He accumulated 99% of his wealth today after his 61st birthday. Heā€™s a great investor, but heā€™s ā€˜Warren Buffetā€™ because of compounding.

Bill Kerr - Open Source CEO
  • Newsletter / Creator: Hidden Levers by Mike Cardona

  • Launch date: Junā€™23

  • Subscribers at the time of our interview: 2,800

- Not compare myself with others.

- Get absolutely clear on who my readers are and not make assumptions about them or try to force them. Iā€™ve pivoted about 3x which led to a plateau.

- Accept the fact that your stuff will suck. Itā€™s ok. I would never read my old stuff because I couldnā€™t stomach the cringe (bad idea). Itā€™s difficult to improve if you arenā€™t actively making an effort.

Mike Cardona - Hidden Levers
  • Newsletter / Creator: Turkey Recap by Diego Cupolo

  • Launch date: Octā€™19

  • Subscribers at the time of our interview: 7,100

Honestly, Iā€™m wondering how to start anything news or politics-related without the pre-Musk social media traffic. Weā€™d have to use an entirely different marketing strategy, and possibly talk to people, sometimes in public. The horror.

So, Iā€™d probably make a podcast with a YouTube channel first and reverse-engineer it into a newsletter if it gains traction. Or the opposite of what we did.

Diego Cupolo - Turkey Recap
  • Newsletter / Creator: A Better Lemonade Stand by Richard Lazazzera

  • Launch date: 2012 (to inform about blog posts / 2023 (as a dedicated channel)

  • Subscribers at the time of our interview: 22,000

In essence, I am in the process of starting A Better Lemonade Stand anew.

This time, my approach is more personal, with a stronger focus on engaging and connecting with my audience.

Looking back, A Better Lemonade Stand was mainly a resource site.

If I had the chance to do things differently from the beginning, I would emphasize building a community right from the start. 

Community engagement is crucial, and establishing a deep connection with the audience early on would have greatly enhanced the platform's growth and influence.

My current goal is to evolve it into a vibrant, inclusive community where digital entrepreneurs can come together to connect, build, and collaborate.

Richard Lazazzera - A Better Lemonade Stand
  • Newsletter / Creator: 1440 by Tim Huelskamp & Andrew Steigerwald

  • Launch date: 2018

  • Subscribers at the time of our interview: 3.3+ million

I wish we would have met Erika earlier.

The co-founders learned a ton experimenting (for which weā€™re grateful) but Iā€™ve learned to scale companies truly, you need to hire brilliant people and generally ā€œget out of their wayā€

Second, early on, we explored various channels - Pinterest, Quora, Reddit, etc.
Looking back, I believe consolidating those efforts into mastery of the scaled channels - Facebook and Google - would have been a more strategic move.

It boils down to the importance of focus ā€“ doing less and diving deeper into the channels that yield significant results.

Tim Huelskamp - 1440
  • Newsletter / Creator: The Follow Up by Nic Conley

  • Launch date: Aprā€™23

  • Subscribers at the time of our interview: 12,000+

I think I wouldā€™ve started investing more time and attention into organic growth like Instagram early on.

Iā€™d also plow way more money into Twitter ads when they were showing crazy results, but unfortunately, that ship has sailedā€¦ haha

Itā€™s still super early, so Iā€™m sure that Iā€™m making mistakes right now that Iā€™ā€™ll look back on in a year, but for now, Iā€™m just heading down doing what I can.

Nic Conley - The Follow Up
  • Newsletter / Creator: The Water Coolest by Tyler Morin

  • Launch date: Sepā€™17

  • Subscribers at the time of our interview: 130,000+

I plan to optimize for metrics that matter.

That means really focusing on click-through rate and other forms of engagement, like replies. These are the metrics that help drive revenue.

Total subscribers is a vanity metric at this point, especially since the Apple privacy changes.

Before Barstool, I had no ā€œrealā€ 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.

Probably my biggest takeaway was that a lot of people have great content, but not a lot of people can run a great business.

Tyler Morin - The Water Coolest

Thatā€™s all for today. See you on Sunday with another exciting interview!

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