So after running the numbers to see how financially interesting a Bootstrap Conference might be…I’m still not sure if the conference business is something I’d want to commit to. I think the revenues can start getting interesting above 400 attendees, or if there was some big sponsor with deep pockets that stepped in to help with an altruistic intent. Otherwise, it seems like it could be a lot of work, with mediocre gain.

Still, I can’t seem to totally shake the idea. Perhaps it’s some personal mission to spread the gospel of bootstrapping…something about this idea still seems worth pursuing.

Anyways, it’s still enough of an itch for me to continue creating a website, flesh out the conference more, and get outside feedback. There’ve been times when I’ve created a marketing site for an idea and quickly realized how dumb the idea is…and times where I’ve created the site and became more excited about an idea as more thoughts took shape.

Without further ado, I spent a weekend hashing out some of the conference details, and created a marketing site for it.

The Bootstrap Conference

In a nutshell, the vision is to create an event geared towards bootstrap founders of tech startups. I define “tech startup” as any business where the principle form of distribution of the product is online. For example, a new neighborhood donut shop wouldn’t qualify as a tech startup. A new donut shop where the primary way to order and distribute donuts is through an app would qualify.

There’s obviously no speakers yet, but the idea is to get leaders from the bootstrap community to share their personal journey and wisdom on one of the agenda topics listed. The way this conference differs from others is we’d really aim for a curated topical agenda. I feel at a lot of conferences, speakers share for the purpose of pitching their personal agendas, or worse, their products…resulting in very little cohesive takeaways for the event. With The Bootstrap Conference, we want to cover the gamut of things every bootstrapper must know. Also, to mitigate speakers selling their own wares, we’d encourage speakers to speak outside their immediate known domain. For example, if we had David Heinemeier Hansson speak, we think it’d be much more interesting for him to do the “revenue” talk versus the “engineering” talk.

As for the location, we really wanted to stay away from the large VC hubs (SF, NY, LA, and Boston). Instead, we really liked the idea of choosing a city we can potentially see bootstrap businesses congregating in the future…like Portland, Austin, Boulder, etc, where there’s an emerging mix of technology, creativity, and culture. For this first one, I’m choosing one of my personal favorite cities, Portland.

I’m pretty torn about the date. My inclination is to either have it sometime in the spring, March/April…or in the summer, July/August…or in the fall, September/October. Winter is just too cold, and we’d be competing with the holidays. Spring is also basically out, because the other major bootstrap conference is in the spring…and we’d want to be respectful.

I’ve no idea how long it takes to put together an event such as this…but I’ve been noticing that even larger conference sites start filling in more of the conference details around 6 months prior to the event. This tells me that conference planning probably starts around 9 months prior to the event, and details start really taking shape around 6 months prior. Then 3 to 6 months out begins the ticket pre-sales, and the final 3 months are dedicated to a major push to sell out the rest of the tickets. Working backwards, the earliest I could realistically have this Bootstrap Conference is sometime in September/October…so summer is basically out. The entire timeline seems a bit arbitrary at this point, so I’m tempted to just leave out any references to actual dates.

Anyways, these are my preliminary Bootstrap Conference thoughts.

Next Steps

Since I’m still very unsure about pursuing this…I first want to put the idea out into the world, and see what the feedback is. Using this site, I’ll do some light marketing experiments to understand if there’s an appetite for this at all.

On a personal level, I’ll also start a local Meetup bootstrapper group to see if this is a community I’d even enjoy building. There’s a chance that running a local Meetup group may completely satisfy my curiosity in fostering a bootstrap community.

Stay tuned!