The Bootstrapped Founder

Reading Time: 6 minutes Building in public once helped me sell my company.

Reading Time: 10 minutes A couple things happened these last weeks that brought into sharp focus just how naively we interact with agentic systems — to the point where we get surprised by the consequences of using them.

Reading Time: 7 minutes Here’s a question I’ve been sitting with lately: if building software keeps getting easier — and it clearly is — then what exactly are we building our businesses on?

Reading Time: 6 minutes There’s something deeply satisfying about watching seeds you planted a year ago finally break through the soil.

Reading Time: 7 minutes I’ve been using Claude Code for over half a year now, pretty much exclusively, to build my platform.

Reading Time: 6 minutes A while ago, I asked my Twitter friends to tell me what the most annoying and most infuriating piece of entrepreneurial advice is that they ever received.

Reading Time: 4 minutes Let’s add another one to the series of entrepreneurial advice that just really irritates me.

Reading Time: 5 minutes Let’s dive into a piece of entrepreneurial advice that’s highly irritating and very dangerous.

Reading Time: 8 minutes We often joke in entrepreneurship about founders having to wear many hats.

Reading Time: 7 minutes Sometimes software founders are a weird bunch.

I saw something on LinkedIn the other day that stopped me mid-scroll.

Many of the technical founders I know really don’t like marketing.

I really want to clean up a little bit when it comes to vibe coding and software as a service businesses, because I think there’s a lot of confusion, a lot of hype, and a lot of complaints about the imminent demise of software as a service solutions.

My dear friend Jack Ellis is an unending source of founder inspiration.

I recently realized something while building Podscan, my podcast database system that does a lot of background data extraction and analysis for my users.

If you had asked me a couple of years ago if I loved coding and software development, I would have given you a resounding yes.

One of Podscan’s main customer profiles that I’ve recognized over the last couple years building this business is marketers – people who think in marketing terms, who have marketing jobs and marketing goals.

When you build a software business as a founder, you have a dream.

Here’s the thing: I’m about to share all the reasons why you should never, ever start a software business.

I know you’re out there.

Today, we’ll dive into the kinds of alternative solutions most founders miss when they attempt to validate their ideas.

We’re living through a fascinating moment in software development.

A couple of years ago, I tweeted that “the best tech stack is the one you already know.”

As I’m building yet another software service business after having built and sold one back in 2019, I keep wrestling with a fundamental question that might sound simple but has profound implications: What do I actually own in this business?

Let’s talk about handling multiple ICPs as a solo founder.

I was recently reading an article about The Great British Baking Show – or Bake Off, as we fans of this fun TV competition call it.

You know that moment when you realize the ground has shifted beneath your feet?

This week, I want to be as pragmatic as possible.

I was reading Brandon Sanderson’s latest novel, Wind and Truth, when I came across a sentence that stopped me cold: “A stronger current makes for stronger fish.”

I think we’re at the precipice of a pretty significant change in how we build software products.