From Social Media Influencer to Substack Writer: A humbling 90 day journey

Sharing my Substack newsletter journey

I’ve been creating content in a niche category for a little over four years. Nostalgia is my thing. I lived it. I know it. My Instagram account exploded after a couple of years, right around the time Instagram introduced Reels. I was growing prior to that, but Reels boosted discovery like crazy.

In fact, my profile grew so rapidly I was blocked by a few people I thought were my pals on the platform because they had been on there longer and it bothered them that the new guy surpassed them. Very petty stuff, I know. I was first to really embrace Reels and that was the gamechanger. Jealousy reared its ugly head.

Drama…!!

What’s interesting is I connected and supported newer accounts, and I do this even to this day, some of which  have even managed to surpass my half million followers in a shorter time posting content they grab from the web.

Which leads me to this note on online decorum:

Don’t go blocking people because they’ve found success. Don’t assume anything.

Be kind, be supportive.

Additionally, I supported those fake pals by hosting them on my IG live show and reshared their content regularly... I’m building this up to make a point here… That early experience on the platform definitely gave me thicker skin on social media. For them, it took away an ally and collaboration partner.

A short time later I learned a couple of them attempted to copy my “80s Happy Hour” live event concept. They don’t do it anymore and there was even a falling out between them. Shame.

Maybe I’ll share that story in greater detail one day, but here’s my point—

Embrace new platform features right away on your favorite platform(s) because these companies have made an investment and incentivize accounts that use the features first.

For Substack, it’s video and ‘notes.’

»»» I launched this newsletter on May 22nd with the idea to write about the past, my personal experience as a first generation immigrant growing up in 1980s Detroit, and the willingness to add yet another thing to my schedule in order to build my community.

Mainly, I’d just grown tired of social media. Not necessarily the part of social media of talking about shared memories, but the part of social media that was not allowing me to scale. Because, after all, social apps are linear consumption products designed to suck the life out of creatives in exchange for likes and follows, so they can insert their paid ads.

I saw this some time ago, but I continued creating original content on Instagram mixed with inspired content and clips. Instagram was paying out a bonus, so there was a nice incentive.

I’d grown jaded with Instagram however, the platform where I had the largest audience. I was making a few hundred dollars a month from the platform until they yanked their monetization. When they did that, I didn’t see an incentive to share original content regularly. This was mainly because creating original content took the longest.

Then came another algorithm update, and then another. An then another. With each update I began to notice that the audience I had built was not the same one that was liking and engaging with my early content. Much of the new audience was unfamiliar to me. As I began to investigate the changes, I learned that Instagram was using a far different distribution system, one I won’t bore you with in this post, but let me just say that it was no longer showing my posts to my most loyal followers.

It’s also important to note that the audience tendencies had changed since I started in 2020. There was a recent article published that indicated that over 65% of social app users were opening the apps for pure entertainment, and not necessarily to engage with creators. Now, I still have relatively high engagement, but I’ve certainly experienced a drop off over the last couple of years.

I’ve had the opportunity to work with many sponsors thanks to my platform. Sponsorships and collaborations have always trickled in fairly regularly. It was while I was updating my rate sheet that something very concerning stood out to me. My metrics were off. I mean, they were really off compared to the screenshots I’d taken from around June 2020 to June 2022. My posts were seeing nearly 30 million views per month. By late 2023 and early 2024, they were around 5 million views per month. Still, very respectable, but this was really eye opening to me.

Since I periodically update my rate sheet, I was a bit concerned about increasing my rates. I was still getting sponsorships, but if I could show 30 million views, I could double or triple my rate.

That’s two strikes for Instagram.

I have this problem where once I start investigating, I don’t stop.

I checked my Linktree metrics. They were down also. Way down. My click through rate was less than 2% per link. Down from around 30% click through. Were Instagram’s changes suppressing my conversions? You better believe they were. Instagram crawls the information through your link. If you are sending your audience out of Instagram, your account will suffer. My Linktree also requested emails, which is a no-no for Instagram’s algorithm. They don’t want you to “own” your audience. Their interest is to keep Instagram’s audience happy and on their platform.

That was the last straw for me. I decided that it was time for me to explore a way to grow and rescue my audience from the clutches of social media.

Here’s a snapshot of my social media following as a point of reference:

• Instagram: 480k+ (owned by Meta)

• Threads: 75k+ (owned by Meta)

• Facebook: 18k+ (owned by Meta)

• TikTok: 17k+

• X ‘Twitter’ (This platform is absolute sh*t and unless you were on this platform since the early days, or paying for ‘premium,’ it will take a tremendous amount of effort to grow your profile)

• YouTube: 2500+

I think I was scrolling through YouTube and remember watching a video about growing an audience through a newsletter when I learned about Substack. I know I was looking at relaunching a website but remember being appalled by the prices from the big dogs, so I searched for a low cost newsletter option.

I remember coming across Beehiiv, and while I liked it’s features, I was turned off by the sliding scale pricing. Look, here’s the thing, it irritates the heck out of me why these companies tier up their pricing based on the number of subscribers you have. I’m in sales, I understand tiers, but the way email marketing companies do their tiers is ridiculous. There’s a much fairer way (fairer to the consumer) to do tiers. Beehiiv was also out.

Thank God there was Substack!

Let’s see, Substack offers a full suite of pro-level features for free, maybe not every bell and whistle (it’s missing automations, but I think that will come in a few iterations based on how Substack is scaling), and they make money when I make money? WOW!! It’s like the best thing since sliced bread! Can you even find anything like this anywhere online that doesn’t come with selling your soul to Meta?! ….

—///—

I have been learning a lot about newsletter writing. I consider myself a fast learner, and I believe I’ve become fairly astute at the way Substack works in a short time. I’ve been posting 1-3 times a week on the platform. Writing and publishing a newsletter consistently is the hardest part for me. Having been in social media for the last few years, I’d grown accustomed to short form content.

Having been on Substack for the last three months I have only one regret, and that is not having started sooner. My metrics are not great, to be honest. I’ll share them below. I’m actually ashamed of them because I came on thinking I was going to convert a big portion of my audience, but that has been much more difficult to do than I thought. More on that below also.

Tangent »

After a few weeks of writing on Substack, something really strange happened.

I started reading articles from really good writers that were writing about personal development, business, social media, and side-hustles. These writers inspired me to consider writing about these topics and how I’ve experienced them in my career as a corporate exec, and through life experience.

What do I do now? Am I going to really write outside my niche?

My idea garden for lifestyle, personal development, entrepreneurial endeavors and side-hustles was growing rapidly. These were not topics I was going to publish here on Nostalgia Nation, obviously. My readers would be confused.

At the same time, I’ve reached a stage in life where my life experience, career, and maturity have come together in such a way that I believe I’ve earned the right to offer advice and guidance.

I say this humbly, but I’ve lived an interesting life, and I’ve always had a passion and desire to help others be successful.

There was no way I was going to just let these ideas sit in a vault and not write about them. I’m still young enough to relate with and impact a younger audience and not too old to not care about giving back and rest in my accomplishments. I’m still hungry.

So I launched

Coffee with John

. But…. I already know about the challenges of spreading oneself thin, so, I wrote seven articles that I scheduled in advance to publish daily for seven days in order to share a small body of work and see what my audience thought.

My audience: 6 friends and relatives. I was starting from scratch. It’s 11 now, my open rate is around 74%

I made up my mind that I would post a new article once a week on Coffee with John so not to get overwhelmed and give up on it. I post between two to three times here on Nostalgia Nation.

The last piece of self negotiation was that I would post once a week for six months, iterate, see what resonates, iterate some more, and make a decision in six months time for future goals for the publication.

I’ll let you know how Coffee With John is coming along over the course of the next six months.

As for this publication, Nostalgia Nation, it’s growing, but I’ve come across a huge hurdle in thinking I could convince even a quarter of my audience to subscribe to my newsletter right away.

As published earlier, I have 500,000+ followers on social apps— So let’s just say that I have just 10,000 followers out of those 500,000 followers on social media that are my most engaged. Note: I’m assuming a certain amount of ghost followers, accounts that follow too many accounts and will likely never see your announcements, and who the algorithm decides to show your announcements to. But assuming all of that; When I post that I’ve got a new Substack newsletter, one would think I’d get 1000-2500 of those followers to subscribe (at least for free) to my newsletter. After all, I’ve spent four years growing those communities.

That’s not the case though, and the reality is far less encouraging. Here are the main reasons why counting on your social media followers to come running to your newsletter like a pack of thirsty hyenas is unrealistic:

1. Instagram, the platform I have the largest following, throttles any post with a link outside of its platform. It also penalizes your account by suppressing all of your posts for at least fourteen days. This has been confirmed by internal sources.

btw… since Meta owns Instagram, Threads, and Facebook, all profiles are impacted.

Below is a screenshot of a post I shared on Threads from my most recent newsletter. Notice I have over 75,000+ followers, but only one like after 3 days! It’s barely been seen by 300 of my 75K+ followers! Meta will not show your link-outs to the great majority of your followers.

Side note: my website goes right to my Substack newsletter.

TikTok has the best “For You” algorithm, Instagram has the best “For Them” algorithm.

2. A lot of the followers on your favorite social media platform don’t care about leaving that platform no matter how much they like you. In fact, a good majority of them don’t want to add an additional app on their phone (I.e., Substack).

3. People don’t want more emails. Have you heard of Inbox Bankruptcy? People are overloaded with emails. I’m still unsubscribing to things I subscribed to ten years ago!

I think this is hilarious….

When I think about why I go on social media, I’m on there for short bits of entertainment or highly synthesized information. In fact, social media has trained us to be this way. So why would I expect everyone to be like me; desiring to make time to “read” longer form content?

Side note: When I joined Substack I followed a lot of writing accounts that wrote about, guess what… Substack. Other accounts that Substack was spoon feeding me were about how to write, or “mindset” of writing stuff. My inbox is full of posts about writing. I think Substack pushes these accounts right away because it wants people to succeed and not give up on writing, but honestly, I’m getting overwhelmed with all the “how to be a better writer” content, so I am going to have to clear some stuff out and be far more selective on which writers I follow now that I’ve been on Substack for a few months. I believe the ideal number of writers to follow needs to be under 50 in order to really appreciate and read everyone’s writing. This is hard to do obviously, since there are a lot of fantastic writers on Substack!

Ok, so there are hacks to overcome the challenges above, but it requires playing the long game.

Instagram’s Algorithm:

Instagram’s IG live is a feature that allows you to connect with your audience live. The catch, before you go live the program is checking off boxes; your Live title, your room’s background, and your background music, as well as any image you’ve got displayed as your image in case you are sharing a slide. All of these things are happening at the speed of AI. And if that isn’t enough, IG allows a small percentage of your audience into the narrow walkway to your live session. If you don’t think IG knows when you mention a product, service, or link out to something, you might be drinking their kool-aid.

So something I’m experimenting with right now is letting the initial audience that jumps on about my newsletter right off the bat… going into my topic and mentioning it upfront, returning to my main idea, and plugging my newsletter again. I’ve noticed a few new subscriptions right after these live sessions using this technique. I have only done two so far, but I intend on going live once a week.

Convincing them to leave the platform:

I’ve been experimenting with a couple of things: The first, which was a giveaway, worked ok. The next one that I’m trying is incentivizing them with a digital product.

Having my own digital product has been the weakest link in my platform ecosystem. But I’ve got something in the works. My goal is to have a sneak-peak/highly abridged version of my digital product to give away to curious subscribers in the coming weeks. I’ll let you know how that goes once I have good data to share.

Quick note: Your topic/niche, powerful writing and unique voice will resonate with your audience. But let’s face it, you can be an amazing writer and thinker, but your reader still has to come to the well to drink. So let’s assume you are writing interesting and powerful pieces.

Ok, last part— People don’t want more emails:

The main solution to this challenge goes back to your ability to produce interesting, well thought out, and well written pieces that your reader looks forward to.

The main thing is making your subscribers want YOUR emails. That’s huge. Easier said than done. You might be thinking, well, I write awesome stuff, that should be enough.

Do you know how many people I’ve subscribed to on Substack? Most of them are brilliant. I can’t open all of their emails. There’s just no way.

So which emails do I open? I open the ones from the people that engage with my content. They have invested time in me, so I invest time in them.

Next, I open the ones with the titles that hit topics I’m interested in.

What gets me excited to open any email from a specific writer consistently? That’s the real question. This one impacts an important metric for the platform, for you, and for anyone that may want to sponsor something in your newsletter.

Well, I believe it’s a combination of the two things I mention, reciprocity and topic. The anomalous thing I believe is your perspective voice. If somehow a writer’s voice and perspective has transcended what’s topical, I will likely open every email they send!

Something I’m considering implementing in the future once I’ve implemented my paywall strategy (prob after 3-6 months of consistent posting) is to “comp all access subscription” giveaway on my social posts a couple of times a month (this will be a one week or two week comped subscription to build some excitement and get some folks moved over from social apps to Substack. I’m still working out the best way to do this, so I’ll let you know in 90 days.

Look; I know this was a lot, so if you made it this far, hey, I really appreciate it! I hope you got something out of it, maybe even enough to leave a like and a comment? I’d love to know your publication and if you also came from years of grunt work in social media. Drop me a note. I read all of them and I’ll make sure to write something back.

See you in the next post!