If you had a chance to start over..

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

I would go bigger with networking, cross-promotions and interviews. Whilst they don’t always ‘convert’ subscribers, they build connections that one day turn out to be super valuable.“

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 didn’t do enough proactive outreach to other Sarahs…but plan to be better at this going forward!

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 I’d avoid or wins, I’d want to be even more focused on:

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

Maybe there’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 don’t improve that’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, it’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 doesn’t exist anymore and we could have done much more of it back in 2020.

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

I would have started earlier.

Business in general–like investing, like training, like relationships–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. He’s a great investor, but he’s ‘Warren Buffet’ because of compounding.

- Not compare myself with others.

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

- Accept the fact that your stuff will suck. It’s ok. I would never read my old stuff because I couldn’t stomach the cringe (bad idea). It’s difficult to improve if you aren’t actively making an effort.

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

So, I’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.

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.

I wish we would have met Erika earlier.

The co-founders learned a ton experimenting (for which we’re grateful) but I’ve learned to scale companies truly, you need to hire brilliant people and generally “get out of their way”. 

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 – doing less and diving deeper into the channels that yield significant results.

I think I would’ve started investing more time and attention into organic growth like Instagram early on.

I’d also plow way more money into Twitter ads when they were showing crazy results, but unfortunately, that ship has sailed… haha

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

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 “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.

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