14 Hard-Earned Lessons After 14 Years as A Content Creator and Entrepreneur
14 Hard-Earned Lessons After 14 Years as A Content Creator and Entrepreneur
AKA: I hope to spare you from my mistakes!
🤩 Hey! I’m Alberto. With my newsletter I want to help you reach your full potential and live your ideal life with a content-based business. I’ve been doing this since 2010.
I talk about productivity, automation, strategy and mindset.
I published my first post on October 10th, 2010. It was a photography tutorial in Italian, which launched my first blog.
The blog turned out to be a hit, both in terms of popularity and earnings. In its second year, I already reached the maximum revenue for my tax bracket.
I never wrote a retrospective article in the 14 years since. Now that I'm sharing my experiences as a creator on this platform, it seems like the perfect time to do so.
I spent quite some time reflecting. Here are my top 14 lessons learned in 14 years as a blogger and solopreneur. I hope they help.
The channel makes the success
My first blog thrived because it was in a broad niche, the competition was weak, and my audience appreciated the clarity and usefulness of my tutorials.
But more importantly, it succeeded because it was 2010 and SEO was the most powerful tool for driving traffic.
If I were to start the same blog today, even with my improved communication skills, it would undoubtedly grow more slowly. SEO has become more challenging, and in the photography niche, visual platforms like Instagram and YouTube provide fierce competition.
Over these 14 years, I've launched other projects. They've been successful only when I chose the right channels - the ones that provided organic growth, like I'm doing here on Substack.
So, how can you tell if you're on the right channel?
Before joining Substack I was publishing on Medium. Changes on the platform killed my growth. I knew some writers were succeeding on Substack. But I was hesitant to jump. I didn’t have the time to curate two platforms.
I took the plunge when I started seeing more and more creators with small audiences quickly succeeding on Substack. So, try a new platform when you see creators starting from scratch there, no pre-existing audience, and growing fast.
Always be collecting email addresses
From day one, my blog featured several widgets inviting people to subscribe to my newsletter for updates. It was an ugly widget with a mediocre call-to-action, I improved significantly over the years. But, as my traffic grew, it kept bringing in more and more email subscribers.
So, more and more people turned from lurkers into recurring readers. And most of my revenue came from the list. No one can trust readers to remember their blog and come back to it just thanks to the mind-blowing of the quality of the content.
The key lesson here is that it doesn't matter if you have a clear offer for your email subscribers, such as an engaging newsletter or a useful lead magnet. Always invite them to subscribe in every page.
Reciprocity works!
Early in my career, I read Influence: The Psychology of Persuasion, by Robert Cialdini. Every blogger and podcaster was recommending it. And they were right.
It’s an evergreen book, with fundamental psychological lessons that apply to every kind of communication.
One of the pillars of persuasion, according to Cialdini, is reciprocity. For creators, this means that if you are generous with your content, your audience will feel obliged to reciprocate by doing something for you. For example, buying what you offer.
At one point, I offered a video course about Lightroom, a popular photo editing software, with a pay-what-you-wish model. While it wasn't a financial success, it proved to be a fascinating social experiment.
I remember a guy buying the course for just a few euros, apologizing because he was unemployed at the time. This wasn’t an isolated case. People were so grateful for my free tutorials that they gave back by purchasing my products.
This makes content businesses so fulfilling. You just give with total generosity. Then, you launch products or services that further help your audience and reap the rewards of your efforts.
Beware market size!
Before starting my first blog, I didn't conduct a thorough market analysis. I was familiar with the niche as an amateur photographer. I knew photography was a broad interest not limited to any specific gender or income level, for example.
The market was clearly vast, and my results proved it - the blog reached 300,000 page views per month. An exciting result when only 60 million people speak your language (and that included kids and old folks, who probably weren’t reading my blog).
Later, with my second project, we tried to help people scale their practice or build their online business through online courses. This is a large and profitable niche in English-speaking markets. But it turned out to be too small in our language. It felt like pushing a boulder uphill... On Jupiter. (2.5x times the Earth’s gravity)
To prevent banging your head against a low ceiling, consider only markets with at least one million potential followers. You don't need sophisticated tools to estimate market size. Just look for creators with hundreds of thousands of followers and discussion spaces, like subreddits, with hundreds of thousands of subscribers.
Beware purchasing power too!
The limited market size wasn't the only issue with my second project. Even in a small market, you can make a good living if your audience can afford high-ticket products or services.
But this wasn't the case for us. Our audience mainly consisted of freelancers and employees who wanted to create a business. They weren't poor, but they weren't willing to spend four figures on our programs either.
If you're in the US or other affluent countries, this might surprise you. But Italy’s GDP has been declining for 16 years, public debt suffocates every initiatives, and the socialist mentality (both left and right) doesn’t help progress. So, both freelancers and employees have limited disposable income.
It's challenging to estimate how much your audience can spend, but you can get an idea by looking at competitors in your niche selling similar products and services.
Every tactic works, but not for everybody
Over the years, I've seen many marketing tactics succeed and fail. Dozen “guaranteed” techniques left me empty-handed.
My answer to this problem is ABE: Always Be Experimenting.
There's no one-size-fits-all solution. But some solutions fit you and your business.
I keep learning from reputable sources (mainly books, newsletters, and interviews). Then, I test what resonates.
In the beginning, this meant throwing spaghetti at the wall. I was ignorant. Now, I developed a better sensitivity. I know which things just can’t work for me.
“Blueprints” and “recipes” fail 99% of the time
There’s a difference between tactics and blueprints, recipes or any other similar term. The latter promise a complete plan that will take you by the hand and lead you to guaranteed success.
Newbies often look for blueprints. They want to cut out risk and decision-making. "Just tell me what to do" they say. But here's the thing: these blueprints often flop.
Why? Single tactics already fail often, because too many factors are involved. Blueprints involve many steps, many tactics. Every single one has to work. And they have to work together.
Such complexity increases the chance of failure. It’s the difference between cooking a hamburger and putting together an entire thanksgiving dinner.
You can still learn from blueprints and recipes. Use them for inspiration. Cherry-pick the parts that click with you. But again, ABE.
Be yourself, but tread carefully
I published hundreds of blog posts and YouTube videos that were totally impersonal: no stories, no jokes, no emotions. But they still did the job. People wanted to learn how to do things and I fulfilled that need.
But things are changing. Instructional content fills the web. And AI is reliably answering “how to” questions.
Online audiences are increasingly looking for help with connection. They're looking for an expert friend, not just an expert.
When I let my personality shine through my tutorials, casual viewers become fans. For example, clients choose me because of the tone of my YouTube tutorials.
But there’s a caveat. It’s true — you'll always find an audience that clicks with you. But remember about market size. Your resonating audience is a subset of the entire market. Be sure that subset is large enough, and affluent enough, to make your business thrive.
Quantity is the foundation
Quantity vs quality is an endless debate among creators. It's a pointless argument, like most black-and-white questions.
We need both.
Prioritizing quality has some problems. First, it’s relative, so, what are you actually prioritizing? Then, it often becomes an excuse to procrastinate, to avoid audience feedback.
So my philosophy is to squeeze out the best quality possible while sticking to tight deadlines.
That said, quantity is the foundation of everything. That’s the reason for the “tight deadlines”.
It’s almost impossible to find creators who don’t publish a lot. They are usually established creators, who know what quality means for their audience and can bet on a few pieces of content every year. Or they are actually extremely prolific on “invisible” channels, like communities, collaborations, and offline events.
You need frequent publishing because:
you need audience feedback to refine your ideas,
you need to put in the reps to keep improving your craft,
you need to stay fresh in your audience minds.
Superhuman patience is mandatory
I’m the most patient person I know. It’s not just me saying it.
But, on several occasions in my content creator journey, it wasn’t enough.
The first product we launched in my second online project was a course on how to build an online business. Our audience was small, and we only made $3,000. We called it a flop and moved on to another product.
A few years later, I heard an interview with a successful online entrepreneur. He revealed that his first launch made only $3,000. But he kept iterating on the same product and turned it into a six-figure moneymaker… I seriously considered literally beating myself up.
We may have done the same, building on the feedback of the few initial customers and iterating to improve our product and launch. We needed to adjust our expectations and be extremely patient.
This is true for products, services, and content. Too often I see creators asking for advice on their disappointing growth. And when I look at their profile, they've only been active for a few weeks. You need months, sometimes years, to make things work.
Business growth requires self-growth
Imagine you're a bottle of water. The success of your business can expand only to the size of the bottle. If it’s too small, your results will be constrained. The only way to expand the bottle, and create space for more success, is to improve yourself.
I studied every marketing tactic. I tested dozens of them. But too often my results have been disappointing. Something keeps blocking me. And I’m confident it’s me.
For example, in my second online project I’ve talked about earlier, I have a co-founder. For years, I never opposed his ideas. I was too afraid of conflict.
This way, we lost the biggest benefit of being a duo, which is building on each other's ideas. Instead, we sometimes both invested time and effort in ideas I didn't believe in, just because I was afraid to speak up.
After I stopped holding back, things improved. The same is true for every personal limitation, like low self-esteem or perfectionism. If you don't work on them, they'll keep steering you in the wrong direction, leading to bad decisions.
The right network changes everything
This is my weakest point. I’m extremely introverted, so I wasn't able to build a network of creator friends recommending each other or collaborating on projects.
I often found other creators whose content wasn't better than mine. They were using the same marketing tactics I used. Why were their results so much better?
As I dug deeper, I learned that most of them had a few creator friends who collaborated, recommended each other, or just bounced ideas back and forth.
So, try to find a few like-minded online friends. No need to optimize for the best business outcome. Just find people who resonate with you and who are invested in their projects. Something will always come up.
Your native language is not a limitation
I spent most of my years as a creator publishing content in Italian. I'm still creating tutorials in Italian on my YouTube channel.
But when I started building in English, many more doors opened:
access to platforms that Italians totally neglect,
far more like-minded people,
access to more affluent audiences.
So, if your native language isn't English, learning it and using it for your content will improve your chances of success 99% of the time. (Here’s an article on how I overcame my insecurity and started publishing in English: How I Learned to Write Fearlessly in English (as an Italian) and Attracted Thousands of Views
There Are No Shortcuts
After 12 years of creating content in Italian, I decided to start publishing in English. I was in a hurry to grow my audience quickly and hoped to skip a few steps.
I invested in a couple of courses from platform experts. I learned something useful, but none of them handed me the “secret formula”.
Because it doesn’t exist.
Sure, there are tactics that can speed things up or make the process smoother. But every creator still has to put in the hard work to:
improve themselves,
understand their audience,
study the platform(s),
learn the tools,
dive into marketing,
develop products and services.
Shortcuts fail for the same reason recipes do: there are too many variables. And your unique traits change the entire equation.
A Familiar Truth
This list feels disappointing to me. There’s nothing groundbreaking or revolutionary here. I’ve come across these same lessons countless times over the years.
But maybe that’s what makes them meaningful.
If, after 14 years, the core lessons remain unchanged, perhaps it’s because they are the fundamental truths every creator and entrepreneur must face.
Do you agree?
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