8 Things I Learned From Planning The Worst Event of My Life

Events suck. Or at least that’s how I felt after planning a baby “Fyre Festival”. After 8 years of producing events, my first festival flopped and I lost everything.

First, let’s set the scene: I was a 25 year-old event producer with my own production company that I launched straight out of college. (another risky move, but we’ll save that for another day) By now, I had quite a few successful events & concerts under my belt. I’m all about challenging myself so it only made sense (in my mind) to raise the bar and do a festival.

I had become obsessed with Woodstock. Watched all the documentaries, lost footage, interviews…I just knew I was the chosen one to create a modern day woodstock. So I set out to change the game: I had the perfect theme, perfect venue, perfect price and perfect line up so by default, it should have been the perfect event right? Right…..

But that didn’t happen at all. It was more like this:


Well not as bad but still…not as great either from an event planner’s perspective. The Event Gods probably would have graded this an E for embarrassing.

After 2 years of recovering, I can finally come out of hibernation and share 8 lessons I learned:

Start small.

The dreams of recreating woodstock could have been traded in for a small mock event. Don’t get me wrong, we pulled over 2,000 people but in a venue that could hold over 10,000, it looked like ants on a farm. Smaller events are easier to manage, have a higher success rate, less expenses & less headache! Whether it’s your first event or first festival, start on the small scale so you can easily validate the idea and grow from there. Afterall, Coachella was once a small concept in someone’s mind that grew over the years.

Get more than enough sponsorship.

Cash rules everything around….us. (Don’t worry, I know the real lyrics) While I wish charm could pay some bills, it definitely doesn’t. Its cool to get a few supporters but the key to successful event planning is to spend other people’s money wisely. If you were only able to bag one sponsor, clap for yourself and postpone the event until you finish fundraising. Sure ticket sales can cover the rest of your expenses but it’s always best to walk into your event with all expenses paid so ticket sales are all profit. We were lucky to get a few supporters but quickly turned to investors when we saw we didn’t have enough money. Wrong move. Event sponsors exist for a reason. Find them & use them. No matter how long it takes, hustle for sponsorship. Lesson: Get more than enough sponsors and if you fall short, stop while you’re not ahead.

Find vendors that work with you and not for you.

There’s a very fine line between vendors and partners. Vendors are the key to any event so it’s extremely important you find quality vendors that understand the bigger picture. You don’t want to just hire a DJ, you want to work with them. What do they need to make this the greatest performance ever and in turn will thrill your audience? Don’t just sell vendor booths, identify and target vendors that your audience will love; work with them to make their stations interactive to boost sales and keep your audience talking long after the event. Don’t just focus on your event, focus on vendors too. I wish vendorspace were around during this time, to help identify quality vendors.

Align with those that believe in your mission.

This is a team effort…don’t let anyone tell you otherwise. From sponsors to venue to vendors, we are all in this together because everyone’s reputation is on the line. Have a meeting, or 7, and really layout your goals. Everyone plays a role in the success of your event, don’t let one person’s greed ruin it. We found ourselves partnering with people to add more “hype” to the event but not enough “value.” Wrong move #2. Our company was dedicated to creating cool events for social change (which will soon be resurrected), but people were more drawn to the ‘cool event’ than the ‘social change.’ Stick to your mission and find those [sponsors, entertainment, vendors, etc.] to ride with you.

Trust your gut.

It’s your vision. No one else really understands it like you do. If you’re not comfortable with something change it & always go with your intuition first. Good intentions bad decisions can easily be avoided by trusting your gut. There were plenty of signs that told me to throw in the towel but decisions were clouded by the momentum and success of our marketing. We had the streets buzzing only to regret ever opening those doors. We put way too much pressure on ourselves to make sure the event still happened.

Have a team….and trust them.

You will eliminate half the stress (well maybe not half but at least a quarter) if you simply get a team! We needed permits, staging, police, security, port-a-potties, lighting and the list goes on and on and on… and on. Your list may not be half as long but get people to help. People who know what they’re doingnot recruiting your friends (huge difference!) and allow them to do their jobs. It will alleviate a lot of unwanted chaos.

Don’t force it.

I know — “It must happen now.” But then again, it actually doesn’t have to. Sometimes it’s best to pivot even in mid motion. Never be afraid of change even if it means cancelling the day of. It may not be the most popular decision but you know best. If things are not flowing organically and there are too many roadblocks, maybe you should pull back and re-strategize but never feel that it has to happen. The world isn’t stopping today, you can host your event another day.

Get over it.

The unfortunate truth is shit happens. Just as with any business, sometimes you lose. The quicker you embrace failure, the better. Don’t sulk around counting your losses. You may be wasting time neglecting another great idea. Admit it, address it, accept it and move on. This failure led me to my new venture so I sincerely hope you fail faster than you soar.

This was the best, worst thing that ever happened to me. It was a game changer in my life and career. But as I look back, I wouldn’t change a thing. At least I had the opportunity to share 8 things I learned to stop you from going down the same path.

What are some things you learned from an embarrassing mistake or failure in your life?