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The Lorem Ipsum Newsletter

#19: How I lost $100K in 1 year (and how to avoid my 5 big mistakes)

Vahur Singa


To me, 2022 was a year of failure. I lost $100K and nearly killed my personal brand.

After getting nothing to work and almost giving up, I managed to turn things around in the most unexpected way.


Here’s the story…

In Spring 2021, my life was bliss.

I had gained 20k+ followers in just 45 days. People saw me as an expert, and opportunities flooded my inbox. Clients were willing to pay me a lot of money for sharing my knowledge about Instagram.

Given how smoothly everything had gone, it felt like I had the magic touch.

“I will create a high-ticket course and make $50k in a week.”

I was feeling so fancy I didn’t even bother to serve 1-on-1 clients while preparing for the big check. So I lived off savings for a while.

That’s where the troubles began.

What followed was a cascade of mistakes that’s painful to look back at. But I figured that sharing my journey may save someone’s career.

And more important than the mistakes are the lessons that changed my vision forever—more on them later.

Here we go.

Mistake #1 – I stopped posting

I knew progress would be slower if I spent hours preparing regular posts daily. So I put all my effort towards other, more important tasks temporarily. I already had a following, and it wasn’t going anywhere.

But this led me to lose touch with my audience.

My reach and engagement went down. I tried HARD to get them back up and shot myself in the foot. I pivoted my content strategy every other week, which alienated my audience even more.

If you ever gain momentum on Instagram, please do me a favor: don’t stop posting to focus on monetization. You will lose something that you may never get back.

Mistake #2 – Selling a high-ticket cohort-based course as my first product

Here’s what you should do:

1. Work with 1-on-1 customers until you notice patterns in their problems.

2. Offer a specific solution to a specific problem as a low-ticket digital product.

3. Build a community of happy customers.

4. Use customer input to create new, more premium services.

But the temptation was so powerful. To sell high-ticket and start living the dream IMMEDIATELY.

Spoiler alert: I sold none.

Mistake #3 – I created a course before selling it

It wasn’t because I didn’t know any better.

Every mentor had told me to sell first and then create.

It makes sense. You may think you know what your audience wants, but the only real proof of demand is money in your account.

Still, I spent half a year crafting an in-depth course and packing a ton of info into the curriculum. Of course, I based everything on what I THOUGHT my audience would want.

Sure enough, it was overwhelming, and nobody bought it.

Mistake #4 – I started copying others

Reverse engineering other creators is not a bad idea.

But don’t forget that what works for others may not work for you. Their audience wants different things and resonates with different messages.

I developed a shiny object syndrome where I tried to copy everything I saw work for others.

That’s how I ended up selling a course about escaping a 9-5 job to an audience who wanted to grow on Instagram.


Mistake #5 – Poor management of time and money

I planned a roadmap of tasks, expenses, and timings for all preparations to sell the course. I HAD A PLAN. Or so I thought.
But I was off with almost every estimation.

  • How long it takes to write a good email sequence and sales page?
  • How to create and promote a webinar?
  • How easy is it to find a copywriter and other freelancers?

Same with course materials. And ads. And video shoots.
The list goes on.

I was willing to pay more than I had estimated. But because of all the mistakes I had already made, it didn’t even matter. After all, I was rambling about escaping a 9-5 job at this point.

I went from having the magic touch to being unable to do anything right.

I don’t even want to describe how much stress I was feeling LONG time.

Fast forward to January 2023.

I’ve taken time off, reflected, went back to the drawing board and returned with a fresh perspective.

First of all, I don’t regret anything. I’m actually quite grateful.


Because by definition, an expert is someone who has made all the mistakes in a narrow field. If all I knew was smooth sailing, I would never become an expert. Therefore, I would build any kingdom on a shallow foundation.

These experiences forced me to grow. To read, seek advice, and practice.

My writing ability had the biggest breakthrough. More importantly – my content writing system.

Many businesses never bother to think about this. They learn tips, tricks, and hacks, but those will never fix a faulty writing system.

I have been improving my system for years. But because I was forced to dig deep last year, I finally nailed it.

Because of this, my reach and engagement are back up. After years, my content is again going viral and I’m making my customers happy. But, this time, it isn’t luck.

A solid content production system set the foundation for the turn-around. I’ve also taught others my system and helped them drive incredible results. So today…

I’m happy to announce my Content Production Masterclass for agencies, companies, and marketing teams. Feel free to check it out.

You’re also reading the first installment of my new newsletter – The Lorem Ipsum.

What’s it about?

While Creator’s Tuesday (my previous newsletter) was about serving insightful ideas and resources from the internet.

Then with The Lorem Ipsum, I want to share my own discoveries and lessons. And “lucky” for me, I’ve had many of the latter.

Every Saturday, you will get a no-bullshit breakdown for growing on social media and making more income in 4 minutes or less.

With this first issue, I wanted to reflect and catch up with you.

However, next week we’ll get into the fun stuff and I will break down exactly how I got 15 000 organic saves on my recent post.

Stay tuned and let’s celebrate new beginnings!

Your old friend Vahur “failed enough” Singa


See you again next week.


Whenever you’re ready, there are 2 ways I can help you:

  1. If your agency, company, or marketing team struggles with creating your weekly content and finding new clients on social media, I’d recommend considering my course:
    Content Production Masterclass: A 7-step system to attract a steady stream of clients online by writing a high-impact newsletter and outstanding daily content in less than 8 hours a week.
  2. If you’d like me to coach or consult you in private, I offer a 1-on-1 coaching program and a 1-hour consultation call. Learn more about my services here.
Sven Nuum
Sven Nuum
I don't know anybody who has deep-dived into content marketing and social media like Vahur. The way he writes using copywriting persuasion principles and communicates with his audience is outstanding.
Mihkel Vetemaa
Mihkel Vetemaa
Only some people understand the social media game and how to tap into human psychology to stop the scroll. Vahur is really passionate about content writing and systemizing it. It's surprising how his content always gets attention.
Mardo Männimägi
Mardo Männimägi
He is a charming person who knows how to listen. Vahur has given me great advice on growing my businesses and podcast. To grow on social media through content, you need to think strategically, which he knows how to do.