Mar 27, 2024 · 6 Min read

A Portfolio of Small Internet Businesses

For the last 6+ years, I have wanted to make this jump. Today, I finally did. Here’s my plan to make a full-time income as a solopreneur/indie hacker.


For most of my childhood, I dreamed of being a professional golfer. I practiced every day, thought about it all day, and was lucky enough to land a full scholarship to play for The University of Akron’s mens golf team.

Turns out, my dreams as a kid weren't the most "calculated". College golf (and pro golf) requires you to be on the road nearly every week. The golf was tough, but the travel was exhausting (especially while keeping up with school work). Not just that, but the odds of making a significant income are one in a million. I loved the idea of who I could become, but had no interest in living the lifestyle it demanded.

By the end of my sophomore year, I had come to a shocking and disappointing reality–professional golf was not for me. Something I had fixated on for years was no longer my future. Furthermore, I was two years into a Finance degree, which I didn’t enjoy all that much. I felt cornered, nearly quit golf altogether (luckily, I decided against it), and knew I needed to scramble to figure out what I actually wanted to do with my life.

I couldn’t change majors. I couldn’t quit golf (scholarship). What I could do was start a side project. Out of this, The DIY Golfer was born. There is nothing particularly special about this site. It wasn’t a wild success.

But it was my “gateway drug” to web development and entrepreneurship. This led to:

  • Teaching myself to code (my story)
  • Working at a bank for 3 years to pay the bills (while I was learning to code)
  • Working at several startups as a software engineer, growing my skills
  • Trying a bunch of other side businesses that didn't really work

Eight years after starting that first side project (The DIY Golfer), I finally decided it was time to make the full jump.

Side projects for life?

While I've had a few semi-successful side projects, I've always felt guilty for working on them. It's either the guilt of working on "company time" (weekdays) or the guilt of working on "family time" (weekends).

I always felt like I was letting somebody down.

So a large part of my motivation for taking this leap is to give myself the chance to go all-in on something, have some tunnel vision, and execute on things I've wanted to for years.

Worst case, I fail publicly, face some humiliation, and have to enter the job market again. At least then, I'll have tried. But failure is not in my plans.

The Goal

My goal is financial freedom. Given monthly expenses of ~$5,500 and a tax estimate of 25%, that means I conservatively need to make $8,000 of topline revenue each month.

At the outset, I’m 1/8th of the way there, and this goal feels daunting every time I look at it.


Over the years, I have saved up enough cash to last me ~12 months. This assumes that I generate no incremental income over the next 12 months, which is obviously not the plan! Ideally, I’d like steady MRR growth over the next 12 months to effectively make my runway infinite (financial freedom).

Portfolio of Small Internet Businesses

So… How does one grow MRR by $7,000 in the span of 12-18 months? If I could definitively answer that question, I wouldn’t be writing this.

After a few weeks of brainstorming, I've decided to lean into what has worked for me in the past. Through past experiences, I know that I can make money by creating high-quality educational blog posts and YouTube videos. I've brought in several hundred dollars per month for over 5 years now doing this, but have never had the time to really dig in and scale it.

I’m good at writing and teaching, it’s a validated revenue model for me, and if executed well, is a low-risk way to scale my revenue.

While I would love to lock myself away in a room for 6 months, not talk to anyone, and build a beautiful-looking SaaS product, it is simply too risky for me at this stage. I need a simple, proven business that I can put sweat equity into and watch grow.

In light of this, my strategy to reach my goal of $8k MRR is through building a portfolio of content businesses. I already have 2 with traction, so my goal is to leverage this existing momentum and grow what I've already got.

Starting point

I've got 3 assets on the web that have at least some existing traction.

Asset 1: The DIY Golfer

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This golf site is established with the following metrics (as of March 2023):

  • 28k pageviews / month (Ubersuggest is wrong in screenshot above—I'm sharing my internal analytics)
  • 6,000 email subscribers

Asset 2: YouTube Channel

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My YouTube channel is largely focused on programming / websites related content.

Asset 3: Personal blog

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While I haven't focused on growing this one, over the many years of writing, it has started to gain some authority:

  • 10k pageviews / month (again, Ubersuggest is off here due to my private analytics)

Leveraging these assets for growth

I expanded upon this a bit in this Twitter thread, but as I explore new business opportunities, I'm going to largely focus on _related_ topics that I can post directly to one of these three assets I already have working for me.

While I would love to make _distinct brands_ for each new project, I unfortunately do not have the luxury of time right now and need to be a bit scrappy about this.