One year ago, I was here.

Surrounded by sun, sea, and an endless supply of Mai Tais.

Hanging out on the Big Island of Hawai’i, I had all the trappings of your stereotypical tech worker on the beach:

  • Laptop that cost as much as my first car? Check.
  • Dreams of traveling the world? You betcha.
  • Passive income side hustle? My villa won’t pay for itself.

I realize it sounds clichรฉ. But at that moment the only thought going through my mind was, “This is totally going to work”.

It’d been just over a month since I quit my job to become a full-time founder. My partner and I hit our first month of $2K revenue for our software product, landed our biggest customer, and shipped a massive feature users loved.

Then my travel blog had its first $5K month, filling in the financial gaps while I acquired customers for our product.

There we were. On the path to the Promised Land of glory, fame, and monthly recurring revenue.

Yet, in the world’s most obvious plot twist…

None of those things happened.

Chain of Craters Road

Narrator: It went downhill from here.

Let’s start with how we got here

In February 2019, we started building Affilimate.

It’s an analytics Software-as-a-Service (SaaS) tool for people running blogs and websites that are monetized through affiliate marketing.

Basically, our users link from their websites to recommended products and services, and earn a commission for any referred sales.

The problem is, those sales happen in dozens of places and have huges holes in the data that would help people understand what’s actually converting on their site and how to improve it. Our tool solves both those issues.

But as luck would have it in a year like this, our first 70 users on the platform were all running travel blogs. Just like me.

You can probably guess where this is going.

Blog crash

No travel, no traffic, no money.

When the tourism industry collapsed in March, my blog as my main income source – and the blogs of all our customers – collapsed, too.

Suddenly, I was making less than $500 in profit per month.

No surprise, customers of our SaaS product started asking to pause their subscriptions. Which made total sense – an analytics tool is useless when all the numbers are zero.


To combat the shock, we gave all our customers 3 months for free. Meanwhile, our costs of running the platform remained the same.

Affilimate crash

This gave people time to process what was happening psychologically – but also helped us prevent over 90% of our monthly subscribers from churning right away.

We were buying time to figure something out.

No boss to get you out of bed

By the end of March, I could barely get myself out of bed in the morning.

It felt like I’d been pushing a boulder up a hill for a year, only to have it flatten me like a pancake.

But instead of starting back at the bottom of the hill, I’d rolled further. Into a syrup-y swamp of stagnation.

No new signups were coming in. My blog income had evaporated. And to top it off, I didn’t have a “normal job” to fall back on.

So I did what any rational person would do in this situation.

I ordered a Nintendo Switch and played Animal Crossing for like 200 hours.

Animal Crossing vs Motivation

This went on for several weeks.

After playing through the main game in record time (and watching the first and last video game streams of my life), I knew I couldn’t continue this way.

I had to resurrect our SaaS: find customers in new verticals and people we could help with Affilimate. Get out of this rut and rally.

Unfortunately, a lot of things sound smart on paper until you actually do them.

Automation and scraping. Content. Cold email. Paid ads. Sponsorships. I tried a lot of things, and none of them really panned out.

I had no scalable, repeatable way to reach new customers in a short amount of time.

By the end of this exercise, I was even more demoralized than before. At that point, I considered consulting work, freelancing, or even getting a remote job.

But the idea of going back to working for a startup felt worse than looking at my bank account.

I had to figure out how to make progress in a way I could control.

Enter my first pandemic side project.

An article that probably changed my life

In April, I read an article Amy Hoy wrote about content marketing.

The upshot is, the most effective content marketing often isn’t blog posts. It’s standalone, mini products. They’re usually free, valuable on their own, and somehow related to your main offering.

This technique is commonly called side project marketing.

Side project marketing

And it’s weird to say this, but Amy’s article kind of changed my life.

Most business advice says you need to do one thing and make it succeed by willpower, determination, and unrelenting focus.

It felt like permission to try something different.

Admittedly, the project I was about to build was only tangentially related to Affilimate. But I saw it as opportunity to start fresh, and apply what I’d been learning for the last 18 months.

So I took this advice and launched a new side project.

It went better than I ever expected.

What’s different when you try a second time

Unlike with my SaaS, I had a distribution plan from the outset.

About 9,000 developers followed me on Twitter, built up from years of blogging and some speaking at tech conferences.

Honestly, I’d never really wanted to build a product for developers before. But that didn’t matter. The goal was to test and learn as quickly as possible.

Leveraging the audience I already had was the fastest way to make it happen.

So I created Blogging for Devs as an email course. It teaches developers about blogging and SEO by helping them create an optimized blog post in 7 days.

Keeping it lean, I launched with a single-page site: a couple paragraphs, a screenshot from my Google Analytics, an opt-in form, and a few words about myself. It was a Friday in the middle of May.


The email list grew to 1,200 subscribers before the end of the month. I kept it going as a newsletter, and from there it grew mostly by word of mouth. It’s just hit 5,000 active subscribers.

The newsletter went on to become #1 Product of the Day when I launched on Product Hunt in August, thanks to kind comments and support from people who liked the email course.

Finally, I created a paid community for subscribers. It’s made over $10K in 6 weeks since the public launch in November.

We just reached $1K in monthly recurring revenue (MRR).

Blogging for Devs

Note: It still took me 6 months to go from newsletter launch to meaningful revenue.

Twice the MRR, twice the revenue, half the time of my SaaS.

Even though I never planned a crossover between these two products, I do plan to take my learnings and apply them to Affilimate in 2021.

Sounds pretty good, right?

From the borderline broke to a successful launch and meaningful revenue, just in time for my 2020 retrospective!

Hold that thought.

A reality check for aspiring bootstrappers

Since launching my community this year (in particular since my accidental Hacker News launch), I’ve received a lot of tweets and emails from people who aspire to “do what I’m doing.”

But I’m afraid people get the wrong idea of both my personal situation, and the financial reality for many bootstrappers.

$10K in 6 weeks sounds pretty good.

But it’s the only “real money” I’ve made all year.

Bootstrapping income summary

Imagine you turn 30 and only make $538 for the entire month. You start to question a hell of a lot of things.

You also can’t forget how much someone with a background like mine could make at an established company.

Before having the bright idea to build my own products, I was the frontend engineering lead and manager at a unicorn fintech company in Berlin. Which brings me to my next point:

The only reason I can afford to do any of this is because I have savings.

It also helps that my blog was still profitable. The 4 years of work I invested in growing my travel blog ended up covering a lot of my business expenses, even during a pandemic.

Bootstrapping income summary

But then there’s rent, food, health insurance, and shit you’ve just got to buy.

That means the entire year will be a financial net negative for me, even if my businesses technically made money. As it turns out, things don’t magically pay for themselves once you’re bootstrapping. Who knew?

The point I want to make is this:

Launching new projects, sharing how it went, and making any kind of money looks great on Twitter. It feels great, too.

Just don’t forget to zoom out for the full story.

$5,000 in revenue from “people on the internet” might seem totally different than $5,000 from “a normal job”.

But both of those buy exactly the same amount of ramen.

There’s no prize for doing it the hard way

If I had to sum up my biggest lesson from 2020, it’s this:

Distribution is everything.

You can have an amazing product that solves a ton of problems. But if you can’t find a scalable, repeatable way to help people find it, you’re toast.

It gets harder when you enter a totally new industry with no network, no reputation, and no unfair advantages. Which is basically what I was doing with Affilimate.

I don’t have an audience for that product: bloggers and affiliate marketers.

My audience is developers. This time, I made something for them.

An existing audience is just one of many potential distribution channels. But I’ve seen what a huge advantage it can be to start with one, as long as that audience is also your target customer.

There will be people who think any sort of success doesn’t count unless you begin as a “nobody”, with no audience or career capital to speak of.

Fuck that.

There’s no prize for doing it the hard way.

You either have a business that makes enough money for you to live from, or you don’t. And as I wrote when I said I was going to launch one startup per month, I don’t need to prove you can build a business in a vacuum.

Leveraging an existing audience – or any other kind of unfair advantage – can make it easier. But it doesn’t make it easy.

Building a self-funded business is hard, lonely, and expensive.

There’s still nothing else I’d rather be doing right now.

To you, the reader

I hope it wasn’t too boring to read 2,000 words of me talking about myself.

There’s an extremely high chance your 2020 was awful. Maybe the pandemic, your business, or your job were the least of what went wrong.

And maybe the upswing is yet to come.

I can’t pretend to know what you’ve been through, or are going through right now. I hope whoever and wherever you are, that things are looking up.

Take care. I’ll see you in 2021 ๐Ÿ‘‹

Project status 2019

If you found this post interesting or want to follow my haphazard attempts at building a successful business, you can find me on Twitter.

Huge thanks to Michael, Princiya, and Benedicte for your feedback on this article.