What Not To Do When Starting Up: Lessons From Launching (And Failing At) An Entrepreneurial Pursuit

A look at what entrepreneurs can learn from the Fyre Festival fiasco.

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As soon as Netflix documentary of the Fyre Festival fiasco dropped, I rushed to watch it. Brimming with the sordid details of one of the most disastrous music events in history, the feature exceeded my expectations, leading me to watch it again, and again, and again- after all, who doesn’t enjoy witnessing a train wreck in slow motion?


Aside from fueling hundreds of memes and providing thousands of viewers with much-needed humor, the documentary was a cautionary tale detailing what not to do when starting up a new venture. It still is a valuable lesson in business that should forever be immortalized in a business school syllabus. In the span of a week, I had watched the Netflix feature every single day, replaying parts of it over and over. My interest in it bordered on compulsion. It wasn’t long before this obsession signaled a much deeper root cause- I was seeing the same mistakes that I made during my stint as an entrepreneur.

It suddenly made sense; I was witnessing someone else make rash business moves similar to the ones I had taken a year earlier. It was easier for me to watch Fyre Festival co-founder Billy McFarland fail, than to confront the path that led me to give up on a lifelong dream.

As soon as I began my career in advertising, I set my eyes on launching my own superior agency by the age of 25. I used my time in the industry to hone my skills, diversify my experience, and gain a deep understanding of the ins and outs of advertising.

By late 2017, I was ready to put all that I’ve learned to the test, and just in time to become the 25-year-old entrepreneur I envisioned myself to be by launching INTEGR8. I began by tackling the essentials: a solid business plan, a cohesive brand strategy, and an innovative, albeit idealistic, vision.

The thrill of running my own creative powerhouse nearly blinded me. I was overtaken by fantasies of pitching for the region’s biggest accounts, launching award-winning campaigns that would put Donald Draper to shame, and posing for my portrait in Forbes’ 30 under 30 list.

While being able to envision a clear career path for yourself is admirable, failing to acknowledge your own capabilities and limitations will always be your undoing. After 18 months of self-reflection and 40+ Fyre Festival reruns, I’m finally able to jot down a list detailing the causes of INTEGR8’s untimely demise. While McFarland’s endeavor was much larger in scale, I saw parallels within my own experience that can be applied to a business of any size.

1. Yes, marketing is important, but it’s not the most important aspect

Fyre Festival’s failure can be attributed to multiple causes: an unrealistic vision, a conman for a CEO, and an unorthodox method of retrieving water containers. However, the most glaring mishap is the extravagant marketing plan and budget that overshadowed the operational side of the business. With US$250,000 being spent on a single Instagram post by an influencer, one can see why guests ended up with doggie bags, in lieu of the gourmet meals they signed up for.

As someone who has spent his entire career focusing on the communication aspect of a business, I knew that spending money on building awareness for the agency was the right call. From the get-go, I invested what little I had into the creation of ridiculously extravagant business cards that would portray to any prospective client that INTEGR8 breathes creativity. The cards were meant to showcase our capabilities and innovative spirit.

My next ill-advised move was to place INTEGR8 at the center of the creative world by sponsoring an industry event. For a company that hadn’t seen the sliver of a profit since its conception, spending money on logo placements plastered around a hotel lobby was probably not the right call to make. While I still believe that investing in a solid marketing strategy is vital to the success of a business, prioritizing it over the more important aspects, such as hiring the right people, and leasing out an office, isn’t advisable.

2. Know your limits, and set a plan

I can’t help but admit that McFarland had a good idea- an app that allows every Tom, Dick, and Harry to book a celebrity for an event. It’s definitely a revolutionary concept. However, instead of focusing all of his time, money, and effort into perfecting the technology, he chose to spread himself thin, and plan an over-the-top music festival in parallel. In order to launch the app, he would have been better off hosting a smaller event where he’d invite the celebrities he can manage to book as well as influencers, and showcase the concept on a smaller scale. Once popularity for the app starts to increase, and the buzz around it intensifies, a larger festival would be the next move.

As with McFarland, I chose to start big. Instead of focusing on my key area of expertise (digital), I decided to create a one-stop-shop that would offer every service conceivable to man. INTEGR8’s services included brand identity development, public relations, 3D production, social media management, website development, etc.

With only five employees working across all of these verticals, our nights were endless. It was nearly impossible to grow our skills as an agency in any one area; there was just too much going on. What made matters worse was my lack of experience in some of these specializations. It made it extremely difficult for me to manage a team when I knew nothing about running a large-scale production project, which in turn resulted in somewhat lackluster activations. Our inability to excel in every area of our service offering became obvious to our clients. It wasn’t long before they moved their businesses to other agencies.

3. Manage expectations

McFarland’s ability to exaggerate his own potential is extraordinary. He was able to convince visitors and his own employees that they would be a part of a historical event. From the fake content on Fyre’s website, to McFarland’s constant lies, the entire communication approach bordered on fantasy. There was no way the festival could have ever lived up to the dream that was sold to thousands of people.

INTEGR8 had a similar issue with spewing off idealistic promises. It’s a trap that I always tend to find myself caught in; I just can’t help but share my vision with those around me, without setting realistic expectations.

As an employee, I always lived by the golden rule of a media planner: underpromise, and over-deliver. However, as a business owner, I threw that mantra out the window, and convinced my employees as well as clients that INTEGR8 would soon rival the largest network agencies.

Those promises soon turned sour when I was unable to match the image that had I painted with the messy realities of running a business. The result? My employees found themselves searching for a fresh start while I accepted that I may never succeed as an entrepreneur.

Would I ever attempt being an entrepreneur again? Yes, I would. However, I’d take every bitter lesson that I learned- and do it better. I’d focus on my skills, make smarter investments, and set realistic expectations for myself, and those around me.

Related: Seven Lessons (From Firsthand Experience) To Prepare You For Your Entrepreneurial Journey

Ayman Jaber

Written By

Ayman Jaber is a digital and social media strategist with experience working across a multitude of industries spanning automotive, entertainment, and construction. As a finance graduate, Ayman combines his knowledge of data analysis with a passion for creativity to develop innovative and holistic communications solutions.