1 Year of Please Hustle Responsibly

I wrote my first newsletter article on Substack around this time last year, which went live the first week of December. I wanted to give myself a little lead time to write the next article. For some odd reason, I decided a twice-weekly cadence was perfect (because 100+ articles a year doesn’t sound insane at all). And this doesn’t even include my additional articles exclusive to PHR+ subscribers! 🤯 I try not to send emails on major holidays and there have been a few days and weeks that I’ve missed, but with this being my 101st article written, it’s fair to say that I’ve learned quite a bit about building a community through a newsletter. I’ll be sharing

• what worked

• what didn’t work

• what tools I use to run my newsletter writing

• what my strategy and goals will be for year 2

• screenshots from my Substack analytics so you can see my full journey.

What Worked

• not concerning myself with a subscriber goal. I wanted to have a realistic sense of what I could achieve based on the strategy, effort, and consistency I was able to put in and maintain.

• having a regular posting schedule that I could maintain. It’s rare that I miss a newsletter posting day, and while I thought 2x per week would be too much, it works really well for me and no one has ever complained about the cadence. Or if they had a complaint, they probably just unsubscribed. Even with that, I think my churn rate is relatively very low. My churn rate is literally something I don’t really even think about, that’s how inconsequential it is in the grand scheme of things. I attribute that to my next point:

• writing quality content that my audience wanted. Have there been times when I’ve published something and thought, “eh, not my best but good enough.”? Yes. But overall, I place a high priority on the quality of my writing and the ideas I put out into the world. I’ve definitely had to do some research for some of my posts, and I was largely rewarded for my efforts based on the responses, shares, and feedback. Writing things only I can write has been a cornerstone of this newsletter.

• getting featured in newsletters that reached my target audiences (podcasters, creators, etc.). I don’t think there’s any one newsletter that drove the most subscribers, I think it was having a collection of folks mentioning me across multiple newsletters all around the same time (February and March).

• cross promos with other creators who have newsletters. I didn’t necessarily care about the size of their email audience, I just wanted to collaborate with newsletter writers whose work I liked, whose work was consistent, and who I knew well enough to ask. I did these with about 3 folks.

• speaking at creator events and attending creator events. While our online lives are a version of ourselves, it’s always good to meet people in person and let them see the person behind the words. It’s awesome to hear people’s feedback in person and to hear what they’re working on. I can’t necessarily translate the dollars and cents ROI on that, but I can say that it translates to online engagement and greater word of mouth, which is equally important. You want people to see themselves in your writing and community.

• updating the welcome message around the 500 subscriber mark. I wanted the welcome message to actually feel like I was welcoming folks into a space, not make people feel like they just subscribed to another “get rich, grow quick” newsletter that was trying to sell them something. As part of my research for this newsletter, I often read and subscribe to other newsletters, especially on Substack. I can’t tell you how often I get a generic welcome message where the writer hasn’t even bothered to personalize the message to their writing style. Those 2% effort things really pay dividends.

• sharing posts on Linkedin through auto-plugs/first comments and in dms. I automate both of these using Assembly and Octopus CRM. I don’t have an affiliate link for either but highly recommend them both. Those two are what I use to manage my Linkedin in general and they’ve been invaluable. Having around 8500 Linkedin connections at the time I started definitely didn’t hurt. I’m at around 11.7K followers on Linkedin now for reference.

• growing my recommendations network. Recommendations with active newsletter writers on Substack with similar/adjacent have been a huge driver of subscribers. However, there is a caveat: I don’t think these are the highest-quality subscribers. It’s definitely a volume situation and the best organic way to grow once they’re set up. But I do believe 80% of the very little churn I do have is people subscribing by accident based on a recommendation and then unsubscribing almost immediately (so I barely even count those). When people post pictures like the one below, I can tell you that probably only 70-80% of the email addresses in that number remain on their lists. That’s not terrible, but it is something to note. As I said, recommendations are a volume game.

What Didn’t Work

• Twitter auto-plugs. I vastly underestimated how deeply Elon Musk’s purchase of Twitter would affect the platform. It still works the same in many ways, but with key communities no longer on the platform, my reach just isn’t nearly as high or as valuable as it was when I started writing on Twitter daily. I stopped plugging the newsletter there around March, the returns just weren’t worth it, and I started going more deeply into Linkedin.

• Dynamic pre-roll ads on my podcast. While I have a great podcast audience, the people who listen to my show are also the ones who likely already knew about the newsletter since they follow me in other places.

• paid ads in newsletters. I’m not sure if it’s the newsletters I sponsored or what but they didn’t convert at all. I would still try sponsoring a newsletter in the future because now I have a better idea of where my audience hangs out. But in the beginning, I think it’s throwing away money.

• before and after posts. People often tell you to tease your newsletter the day before it goes live and then do a post after it’s live. I’m not the type of person who gets people excited about things based on one text post, so this just didn’t work for me at all. Simply taking sections from my newsletter after it went live and posting them on Linkedin with a link to check out the full post was far more effective.

Tools I use for my newsletter

• Assembly: Linkedin scheduling and auto-plug/first comment. Also has an AI feature that allows me to input a link to a previous article and generate a Linkedin post. Super great for repurposing old posts that performed well or are currently timely to generate new eyes and subscribers.

• Octopus CRM: Linkined automation tool that I use for growing my connections and sending DMs to current connections. I’m able to send messages along with my connection requests to bypass LinkedIn’s dumb 5 “send note” limit for connection requests.

• Obsidian: This notetaking app has my heart, and I often jot down notes, snippets, and other things on the go related to this newsletter. I also have a whole folder dedicated to PHR with: a roadmap, an outline for my revamped pitch deck, my marketing strategy, my running list of upcoming article ideas with title and subtitle packaging, and a lot more.

• Notion: my posting calendar is in a Notion doc, and I have subpages for potential articles I’m fleshing out. The calendar feature in Notion is awesome. When I add a post to a day, I can click on that post and write within it, keeping everything nice and tidy. I would say that the majority of my article ideas that don’t require a lot of photos, links, or formatting (with block quotes, embeds, etc.) are written in Notion first and then transferred to Substack. I’ve occasionally used Notion AI to help me outline an article if I have an idea but am not sure how to frame it. I also will use the calendar for keeping notes on things I want to include in planned articles that aren’t necessarily article-related (like curated news, a community spotlight post, a cultural event or holiday I want to be sure to mention, an upcoming creator event I’m attending, an affiliate link, or even a campaign I’m promoting).

• Riverside, Descript, and Adobe Premiere: I use these to record, edit, and audio mix my private audio podcast episodes, respectively. Riverside works really well with my USB mic, I like how my voice sounds and Riverside allows for uncompressed audio downloads. I could probably record and edit in Descript but I don’t think Descript allows for uncompressed audio downloads. Not a huge deal for 90% of people, but now that my ear is trained, I can’t go back. Descript is great for editing by text, which I can also do in Premiere. So in reality I should probably only be using Riverside and Premiere, as Premiere lets me edit audio by text and have more control over my audio quality (mastering the audio, making sure the levels are right, etc). It took me writing this to realize that but whatever. I’m sure there are easier setups out there, this is just my overly complicated workflow. I think the best bang for your buck is Adobe Audition which does all of this, or Descript which does all of this with less audio-enhancing options, but you live and you learn.

• beehiiv: Yes, you read that right. I switched this newsletter to beehiiv like 3 days ago, and I’m hoping on everything I love that I migrated my paid subscribers properly (so let me know if you can read this!). Substack was great for my first year of newsletter writing. I met some incredible writers and learned a lot about growing a newsletter without the pressure of investing in a paid newsletter platform without knowing how fast my audience would grow, or what features I actually needed and would benefit from. I’ll be making a longer post about why I decided on beehiiv and made the switch (their Black Friday sale didn’t hurt), but for now, here’s an affiliate link to check out beehiiv for yourself. By clicking the link you’ll receive a 30-day trial + 20% OFF for 3 months.

What I’ll be focusing on for Year 2

• Getting creative with podcast ads, especially mid-roll and post-roll ads. I think instead of plugging the newsletter directly at the beginning, I can create custom ads that are relevant to each future episode and link people to things that would get them on the email newsletter. For example, I could lead people to the creator database or a freebie that requires them to become a subscriber to access. I could also probably persuade free subscribers to become paid subscribers through the podcast (sometimes people just need multiple touchpoints).

• Getting consistent on YouTube. I think YouTube can be a way higher driver of discovery and new subscribers on both platforms if I am able to stay consistent there. Consistency on YouTube has been the hardest thing ever as I don’t like editing, but I think I can build a life and system that allows me to edit and ship videos faster.

• Do more cross-promotions. I post roughly 8 newsletters per month, there are plenty of opportunities for me to use the Community Spotlight section I created. I think it’s a fun way to feature others in my community who are creating awesome work and share our audiences with each other.

• Grow my recommendations network on beehiiv. I think now that my newsletter is bigger (i.e. over 500 subscribers) and that’s not seen as a bad thing like it was on Substack (because small creators want to help other small creators), I should be able to get back to 34 folks recommending me, if not higher.

• Monetizing my newsletter in more ways than one. Having PHR+ is awesome, and I’ll be adding courses, masterclasses, and brand partnerships to my revenue streams to meet people where they are.

• Building out the community perks. I want to grow the creator database and start making connections for people looking for mentorship. Mentorship is something that’s been pivotal to me and something that is largely unique to this community. I want to lean into that value proposition and see how best to do so sustainably. I’ll also be running seasonal creative sprints on PHR+ so I’m excited for this new feature to hit your inbox and get you engaged in some public homework.

• Staying consistent and emphasizing quality. I definitely believe this will be imperative for the growth of this newsletter. This feels sustainable, and I’m always asking myself what more I could do while still keeping the quality high.

I hope this gives you some perspective into what 1 year of consistent writing could look like. I’ll be sharing more about my wins on Monday but with 640+ subscribers and a clear idea of where I’m headed, I’m very satisfied with my first-year efforts. Happy to answer any questions you may have about writing a newsletter!