I made my first internet dollar! 3 lessons I’ve learnt


I’ve been listening to Indie Hackers and My First Million podcast for the past year. I’ve previously started my own high school math enrichment classes as a business, but that was in the physical world.

So I set a simple goal this year- earn my first internet dollar. This may sound like a stupidly simple and easy goal, but I believe in achieving simple things to that you condition your mind to believe that you can do it. It’s very similar to getting your first pull-up: once you get it, the next few reps come way easier.

Early this year, I chanced upon an opportunity after listening to Courtland Allen talk about @Janel’s Newsletter OS. I thought to myself- ‘Wow that’s incredible, I’ll love to learn the exact steps that Janel took for Newsletter OS to be a success.’

Enter Their Timeline

After I curated Janel’s tweets that showed how she launched Newsletter OS, there was positive response from Twitter. I quickly launched a Substack and posted the link on IH. @rosiesherry spotted the post, notified Janel and it quickly gained momentum. After the post got featured on IH, I realised that there was real demand, and quickly pivoted to Ghost as I heard that Ghost provides better SEO.

So what’s Their Timeline? Their Timeline is a newsletter that captures the exact dates when an individual hit some milestones or took some specific actions. Most business newsletters/podcasts tends to focus on the big picture, but I feel that many people who are currently grinding away will love to have a glimpse of the specifics.

Lesson 1: Curation is valuable

To be honest, there was a period whereby I stopped sending out new issues on Their Timeline as I was worried that curation is not valuable. Like many other people, my ideal newsletter is Ben Thompson’s Stratechery, which provides in-depth analysis. But after listening to Courtland’s episode with @yaroslawbagriy (Newsletter Crew) and consulting @BrucePinchbeck via Twitter, I realised that mindful curation is valuable. I spend hours putting together each issue so that my audience can get their entrepreneurial espresso in 5 minutes. That’s a factor of 36 time saved.

Lesson 2: Dare to validate your idea by asking for 💰

Whether it is because of the social conditioning that money is bad, or the fear of rejection, many of us do not dare to ask to be paid for our products and services. But it is super important to note that money is nothing more than a store of value, and if you see that you’re actually providing value to others, you should ask ‘to be paid’.

If we can change our mindset around money as a zero-sum exchange and move to a positive sum game, then we can see that consumer surplus actually means that our customers gained more than they gave. Likewise, leverage in the form of media/code allows us to gain more than we give as a product can be delivered to many individuals even though we put in the hours to deliver one issue.

Lesson 3: Adopt the barbell portfolio in your life

Survival taught us to be risk adverse, society conditions us to know what to expect round the corner (this is why career progression is so attractive). But being an entrepreneur means that you won’t know what is next for you. You have to learn to be comfortable with uncertainties, and think in terms of probabilities.

That being said, having only uncertainties can make it hard for us to function. If you are only worried about your next meal, you can’t make sound long-term decisions.

An idea that I have been tinkering around with- adopting a barbell portfolio. While this idea originated from Nassim Taleb and is used to describe financial investments, I think it can be applied to our sources of income as well. Take a few bets on projects that have low probability of success but extremely high upside, and invest at least 60% of your time in making dependable money, even if that means lower potential for financial growth in that area.

I think this is a very reasonable approach for budding entrepreneurs- only when we have taken care of our most basic needs, then can we have a clear mind to think of the big picture.

What’s next?

Obviously, much more work needs to be put in to make Their Timeline a better product for the audience. I also want to increase my customer base.

Paying it forward

The IH community has been very welcoming and supportive. I strongly believe in helping people whom I am ‘one step ahead of’, so if you are someone who still has not made your first internet dollar, I’ll be more than happy to offer any advice that I can give! Just leave your questions below. :)

I am also available on Twitter where I tweet about entrepreneurship and deep work, and my other Substack P2PAAP where I write detailed thoughts and actions that I take while being a minimalist entrepreneur. I strongly believe in details over high level ideas, so feel free to subscribe if that sounds like something you’re interested in!

  1. 1

    @pohjie great write up! Keep it up and keep hustling. You're onto something amazing :) And yes the internet needs way more curators! There's so much content out there.

    1. 1

      Thank you! Hopefully Their Timeline will grow big enough to be featured on Newsletter Crew in the future! 😄

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