🧱 Building Open Source Projects with Friends - Do and Donts?

#webdev #programming #opensource #ai

There’s something undeniably rewarding about building with people you admire — not just as coworkers, but as friends.

We recently launched Enthusiast, an open-source AI agent designed to help teams access their internal knowledge in plain language — think product info, support docs, or internal processes, all searchable and actionable.

But instead of telling you about the tech (we’ll link that below), I want to talk about something you don’t often hear in dev blogs: what it’s like to build open source with friends — and why that turned out to be our biggest strength.

What It’s Like to Build with Friends

There’s a classic warning in tech: “Don’t work with friends.”

And after having three friends as technical co-founders in the past… I can confirm: the fear is valid.

Yes, personal dynamics can blur feedback.
Yes, tough conversations might get avoided.
And yes, your project can strain... or worse, even breaking the friendship. (At least for a while.)

So why did I start to work with my friends on Enthusiast again? And how did it proved the opposite?

We were mindful of the risks.

I'm always a believer that past failures contribute to future success. Thanks to the past 3 "failed" friendship turned co-founders, I became much more aware how to navigate the situations. And here’s how I approached it this time:

📐 Evaluation phase
Before committing, I asked myself two questions:

Do we share the same values?
How do I feel after spending time with them?

My friend Kasia often says her life principle is "Love, Health, and Wealth". That made me thought of mine. Turned out to be Faith, Love, Health, Wealth, and Joy (yeah, I'm greedy). But what matters is that we have overlaps.

What's as important is that after every hangout, I felt recharged. Calmer. Softer. That was a green flag, for both emotionally and energetically.

🚩 Decision Phase
Once we agreed to start building together, I did the basics:

Clear expectations around roles, time, and compensation
A roadmap and even a strategy workshop

(🛼 Spoiler: the roadmap became irrelevant pretty fast. Priorities shifted. But the alignment exercise still built trust.)

🏃‍♀️ Working Together: A Daily Practice
Friendship doesn’t replace structure. If anything, it demands more of conscious planning. (Now I think of it. Any relationship should follow this rule.)

So I created a living “Do & Don’t” list for working with each friend. On top of that, the simple but foundational things are done even more intentionally:

Be prepared for meetings
Say lots of “yes, and…”
Follow through on what we promise
Stay transparent and give updates (over-communication is okay!)
Be playful, without crossing boundaries

(I like to plug fun quizzes into our weekly updates 😄)

*Did we hit conflict? *

Yes, of course.

But we operate on the shared belief that good work comes from iteration, not perfection, so we don't always have to be the one that is right.

So we compromise, experiment, and move forward forward together. Because progress is not done by one decision.

As long as we’re learning and acting, momentum builds. And with enough of that, speed follows.

Are we still the same friends outside of work?

I was really worried about this in the beginning, which was great. Because that kept me alert (while looking chill) enough to put more understanding and careful action into our relationship. (No, it's not exhausting. Because I love them.)

At the end of the day, relationships are built through time intentionally spent. Working together gave us that.

How about outside work? We don't really talk about work (that much). Instead, we continue to talk about life, faith, family, and the future. And we also plan fun activities to celebrate life together.

(One of those golden summer evenings by the lake, hanging out with Kasia and my dog)