Just yesterday, the seemingly promising Programming Languages Festival failed to raise enough funds on Kickstarter: its organizer, a YouTuber who goes by Context Free (I see what you did there) asked for $50,000 and raised $8,709. Given that he is a popular content creator and the speaker list was impressive (boasting prominent language designers and experts) I feel compelled to break down why this conference wasn’t viable in its current form. I also love offering programmers a glimpse into the messy business of running tech conferences, and this is a timely opportunity.

As a full-time indie organizer—who is currently doing okay for himself—I hesitated to write this essay because it could seem like I’m punching down. That said, I believe there are significant lessons to mine from this Kickstarter initiative: enough of them to be worth coming off as ruthless.

Indeed the tone I bring you today is bossy if not altogether shameless: forgive me, but you’re reading this from my personal blog! My hope is none of this puts you off too much and you come away feeling it was a worthy read.

A note to Context Free: there is biting commentary here; I trust you’re able to take it on the chin and I commend you for taking risks. Hit me up if you want to talk shop.

Story Beats

Each lesson tends to carry personal anecdotes so it feels right to call them story beats. We have four in total:

• The need for a track record
• Conference operations: a black box
• The optics of seeking $50,000 upfront
• Ship vision first, polished product later

The Need for a Track Record

TL;DR: Unless you’re John Carmack or Nintendo you can’t launch a (profitable) conference without a track record.

When you’re still relatively unknown selling conference tickets becomes a formidable challenge.

I decided my first conference (2019) would have to be framed as a trial run: I dipped into my personal savings to cover the venue deposit, travel stipends for contributors journeying from afar, and so on. To attract attendees I went for heavily discounted access, with tickets priced at $50. I kept costs down and cut corners. I needed to accept that my first year would operate at a loss (fortunately, we managed to break even.)

Long story short: it took until early last year (2022) for me to establish myself sufficiently as an organizer and transition to full-time status with Handmade Cities. These days I can pay for my rent in Seattle, groceries, and the occasional night out. At the time of writing, however, I can’t put any money away towards retirement.

It is my view that you need a strong spirit of risk-taking and a willingness to endure the long haul: doubly so if you’re indie. It’s actually unclear whether Context Free is looking to be independent or not? More on this later.

Conference Operations: A Black Box

TL;DR: Much like build systems, programmers may underestimate conference organizing because they only interact with the results.

In the programming world it is difficult to prove to software engineers that build systems are actually hard to write from scratch. (Took me a while to get it!) Unfortunately, this exact phenomenon plagues the idea of running conferences too. For example, I personally unde