Why I canceled our festival—and my event advice for founders

Event marketing is quicksand.

No, event marketing is a pit of quicksand, and just across the sucking sound of death, you can see a party, piles of cash, organic impressions and media coverage.

It’s a trap.

A year ago, I threw the biggest event I’ve ever done. We spent tens of thousands of dollars on a festival for our company in what really was one of the coolest marketing plays I’ve ever done. While I think it had value, I have to admit there was a huge learning curve, adversity, emotions, and a hefty serving of unknown unknowns.

So many startups I talk to want to host events to get the word out about their company. On the one year anniversary at my biggest stab at doing it, I’m going to tell all to help someone be a bit wiser than I was.

We weren’t exactly event newbs

At my last agency, I helped plan three or four major parties. Throughout my time running GoWild, we’ve hosted our own share of events. They’ve always been smaller scale parties, or events we’ve tapped into. These included half a dozen investor parties, industry pre parties, trade shows, GoWild member meetups and sponsoring events. Send It Slam came to life after we were invited to help launch a 3D archery competition at someone else’s venue. After a lot of poor communication with the host, we walked and decided to do our own event.

Send It Slam was born.

Send It Slam was an outdoor festival hosted by GoWild, complete with a 3D archery competition, full lineup of musicians, food trucks & breweries, a vendor village, youth entertainment and more.

While we had chosen venues, organized food and drink, hired musicians, found sponsors, coordinated co-promotions with brands, and even ticketed events in the past, this was new territory. We thought we knew what we were getting into though.

We had no idea.

The challenges with a festival

To start planning, I built out a simple profit and loss for the event itself. Every time we realized we needed something—security, ice, venue, whatever—it went in the P&L. Every time we had a revenue opportunity or a new sponsorship came in, that also went in. With a few hours of work on the model, we thought we had a grasp on this thing.

It was a good reminder that a model is a stupid spreadsheet—it’s not the work. The challenges racked up quickly:

Venue. Location after location turned us down. Two different venues verbally committed before walking back on the agreement due to the archery. Securing the location at a price that’s going to work for the business model and the traffic of the event is one of the most important steps to take.

Food and drink. Food trucks wanted nothing to do with us. They all wanted guarantees, something we were trying to avoid. When we started looking at Indiana for a location, our Kentucky breweries had to pull out due to laws around serving in other states.

Insurance. Venues would not book us until we had a plan for insurance. Securing insurance with an event that had archery was a headache.

Entertainment. Finding artists of the size we wanted was not easy. Most booking agents are slow to respond, do not communicate well, want you to set the price or are vague about what they want, and did I mention they sucked at simple communication? Every artist also has a list of requests that we wanted to accommodate to be good hosts. I will add the artists we ended up booking did not have these problems.

Sponsorships. This part was actually one of the easier checkboxes for us—we covered much of our expenses with sponsorships, hard to do on year one of a festival. But with any kind of marketing sponsorship, you’re selling eyeballs and we had no clue how many people we could get to attend. We were lucky to land some major brands, including Black Rifle Coffee Co. as our title sponsor, and Bear Archery for the archery course.

Ticketing. We tried a new service for tickets, and I regretted it from the get-go. We should have just used something standard like Eventbrite. Instead, my development team was installing a white label ticketing system that was overkill for what we needed.

Staffing. Professional event planners are very expensive. Our team worked the event, which saved us thousands, but it meant we did much of the grunt work leading into the event ourselves, including putting up fencing, managing attendee flow, brand setup, etc. We hired several hourly employees for trash pickup. Despite hiring two people, four showed up (I still have no clue how this happened) and we found ourselves asking some to leave on the day of the event.

Sound like a lot? It is. And we haven’t even hit how hard it is to find the right venue for your event. The setting for your event decides so much of how people feel about the event itself, ranging from parking to attendee traffic flow, aesthetic beauty (it matters so much) to locations for food, toilets, waters, beer and so on.

Making it rain

On the day of the event, it rained.

And I don’t mean it drizzled. It poured at times.

Setup was miserable for our vendors. The rain killed the early attendance. The water shorted out our electric (another thing we learned—have backup generators on hand). I fired our video contractor mere hours into the day for being a drama queen. I have a wheat allergy, and must have had a cross contaminated meal from the food truck—I was sick for the rest of the day after lunch.

It was rough for a bit.

Around 3 or 4 pm, the rain started letting up. We had about 500 people in attendance. The music was amazing, most of the brands had a great experience, and our guests loved it. I found myself meeting people from states far and wide—16 states in total. I had GoWild members asking for photos with me and they wanted me to sign their Send It Slam posters. It was surreal.

Why we canceled this year

We had planned to do Send It Slam again this year. In fact, I had an agreement with a venue that was going to allow us to double capacity, and add shooting clays and fishing into the mix. We were going to have a podcast barn, and we had some major podcasters committed. It was going to be an epic event that would have been taking place 30 days from now.

Canceling it was the right thing to do, but it was a huge blow to my ego. Despite all of the challenges, I loved Send It Slam. We had effectively pulled off creating what the GoWild community is all about. We took a virtual community and gave it life. I was embarrassed to have to tell our team we couldn’t do it.

What happened? It was two things.

These events take time, and we didn’t have it. Our team is launching Holler Commerce, and I’ve bet the future of our company on it. We don’t have time for a distraction.

Secondly, it was the cash flow of events of this size. You should know, you’re going to front load a lot of expenses. Many of your vendors need at least 50% up front, and that’s cash you won’t recoup for months. Beyond that, you’ll have signage, media for awareness, and other hard costs that rack up quickly. You can plan to expense more than half the costs up front and not make that cash up until the month of the event.

It’s hard.

We couldn’t take the risk this year, despite being on pace for profitability with the event. As you’re aware, the economy is hard on startups right now. I had to do the right thing and protect the company’s cash instead of throwing another party for our members.

My advice for your first major event

It’s possible to host a great event on your first go. You don’t need an event planner, huge budget or a big team. Here are some tips to help you get started.

Start small

If you’re planning an event for your company, don’t try to create the next Bonnaroo. Our approach in the early years was the right one. Sync up your event with existing trade shows, when you already have an audience in town. Throw a pre-party to the event, when people are just getting to town. We filled a bar with 200 people with this approach one night in 2018. I spent way less to pull that party off, and never had to deal with security, insurance, marketing, or a dozen other line items.

Find sponsors

No matter how small, you’ll be able to find brands who want to be involved. When we’ve thrown parties in rented spaces or bars, my approach is to usually try and cover my expenses for the venue, food and drink. This is often just a few grand, and very doable if you’re leaning into trade show traffic.

Build a model

No matter how small your event, create a profit and loss. For a marketing event, you should be trying to lose as little money as possible, not make money. I’ve become friends with festival legend, J.K. McKnight, the founder of Forecastle. J.K. taught me that most festivals lose money for years before turning a profit, so don’t expect to beat the average by three years with your event. Remember—this is for marketing and awareness. It is an expense, it’s OK to lose some. The goal is to lose as little as possible. We were fortunate with Send It Slam to get to a wash on year one, which was an incredible accomplishment. I couldn’t have done that though without having started small on other events.

Go light on entertainment

The bigger the name you book, the more expectations there are from the artist and the crowd. Bigger names come with expectations for a grander stage, green rooms, contract riders, and so forth. For most people and events, you can get away with a good sound system and a great playlist. If you need live entertainment, find up and coming talent that will work with your budget and may have holes in their calendar that they’d like to fill.

Take time to tour venues

This is critical. Prices vary wildly and you can’t judge a venue by photos. We toured and considered a lot of locations for Send It Slam’s second year before landing on the location (you know, the one we canceled). There is someone out there who will be as excited about your event as you are, and they’ll be proud to work with you. Don’t settle for someone who doesn’t believe in it. You need a partner. You might even get lucky enough to find someone who will negotiate their rates down just to get to partner with your brand.

I still fully believe in the power of in-person events. It’s flipping a switch that is at the core of what makes humans tick—social experience. I think there is a good chance I’m not done with live events. Part of me deep down even loved doing this so much that I would love to one day start a festival of my own. But it’s expensive, and it takes years to build a following. Be realistic in your expectations, and remember—this is about connecting with your customers, not your ego.

Who I’m listening to: Send It Slam playlist

What I’m reading: “Play Bigger” by the Category Pirates

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