Guest post: 5 ways to plan a successful conference (even when it’s about failure…)


FailCon is a unique conference that focuses on common startup mistakes and failures. It brings founders and investors to the stage to discuss what they learned and how they recovered. Cass Phillipps is the event’s Executive Producer, and a prominent member of the startup community. She was kind enough to share her key strategies for conference success.

The events landscape is growing more competitive, especially this fall. How do you create an event that stands out among the pack? In its second year, FailCon is sticking with what it shares best—practical insights from the leading minds in technology, entrepreneurism, and venture capital—plus adding new workshops that will allow for more hands-on learning. Here are 5 pointers that shaped our approach for FailCon, and hopefully will help other event producers, too.

1) Be Specific

Create a conference that fills a need not currently being met, and covers that need specifically. A new conference focused on startup web design, like Warm Gun, or one discussing only music startups and technolog, like SF MusicTech Summit, is likely to do better than a new event on just “Technology” or “Startups.” Intimate and targeted one-day conferences often yield more interesting discourse than the old days of massive expos offering “something for everyone.”

2) Be Practical

Attendees are looking for practical, actionable information. FailCon’s mantra is that it’s not by emulating another’s success that you will succeed, but by avoiding their failures. Unlike most events, FailCon recruits leading founders, investors, and service providers like Etsy, Foursquare, and Silicon Valley Bank to share their mistakes and the solutions that did—and did NOT—work. This gives attendees a clear list of action items and lessons to take back to their companies, rather than some memorable tweets and directionless catch-phrases.

3) Be Realistic

Before starting the show, get quotes from venues, caterers, printing companies, and A/V to get an informed sense of what it will cost. Now figure out how many people recognize your name in your industry and how many you could personally reach within one degree of separation (not blog posts or mailing lists, but personal invites); take that number and cut it in half and you’ll have an attendee estimate. You very well may get some great help promoting and see a better turn-out than that, but aim lower and you’re more likely to succeed.

4) Know Your Audience

Understand who will want to attend your event, and what they want to gain. Reach out to some ahead of time and ask who they want to meet and what they want to learn. Study similar events and see who spoke on what topics. We know that FailCon will attended by more than 400 of the brightest minds in entrepreneurship, so we ask the influencers who have RSVP’d, like Dan Martell, Caterina Fake, and Edith Yeung and incorporate their suggestions. But don’t ask too many people or you’ll get dozens of disconnected replies—cherry-pick those you trust.

5) Know When To Call It Quits

We’ve seen too many events this season cancel due to low attendance and lack of funds; and many of those within days of the show. This is completely unacceptable, and bad for business: attendees will not only be angry, but will not trust your future events. Look at your attendee count about 2-3 weeks out and double that for a surprisingly accurate idea of your final count. If it is significantly too low, consider postponing the show right away to work harder, get advice, and improve it in the future.

You can read more about Cass Phillipps’s work at

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