How I Executed 4 Ideas Within 36 Hours, Failed Brilliantly but Loved it: 5 Lessons Learned

How Much Money Can You Make in 36 Hours?

That was the premise of the Entrepreneurship Group at McIntire’s (EGM) first annual “EGM Hustle” competition. Three to five people per team, $50 of starting capital and 36 hours to make money. For some, it was an exercise in how many Cookout burgers and Christians’ pizzas they could flip and sell to drunk students on the corner. But I wanted a challenge. I wanted to be pushed out of my comfort zone. I wanted originality. My team consisted of my brother Tom, a first-year and myself. We executed on four ideas within 36 hours, failed brilliantly and loved it. Here are 5 entrepreneurial lessons learned.

Lesson 1: If You’re Playing with Other People’s Money, You Play by Their Rules

I was both anxious and excited about this competition because I finally had a 36 hour deadline that disciplined me into executing on an idea. The tough part was coming up with that idea. I knew that whatever the idea was, it had to involve a mix of three elements: (1) Sales, (2) Scale and (3) Simplicity. Therefore, I began planning ideas 24 hours in advance so I could execute them during the 36 hour timeframe.

Where others saw the 36 hour time limit as a constraint, I saw an opportunity. The post-competition awards were planned to be held a few days later and each group had an opportunity to share their results. To make money you have to sell. Most people tend to think of selling products or services. I wanted to sell time. I wanted to sell my five to ten minute presentation slot to any company willing to pay to advertise in front of 20 ambitious, entrepreneurial students. I had narrowed a list of companies from restaurants that want greater college exposure to local tech companies looking for interns.

Unfortunately, I was shut down. I shared my plan with an EGM judge to make sure it was within the rules but I was told that the company presentation would fall under “execution” and that it must be done within the 36 hours.

Track record: 0-1.

Lesson 2: Don’t Get Stuck with One Idea – You have to Learn how to Pivot

Still stuck in “advertising mode,” I wanted to sell companies advertising opportunities via stamps or wristbands at bars on the corner. For example, I would broker a deal between Trinity and Redbull to have custom Redbull-branded wristbands put on students’ wrists. Redbull would pay me a brokering fee and I would pay Trinity. The difference would be my profit. I thought this was the greatest idea in the world and that everybody would applaud my creative genius.

However, things didn’t work as planned. First, the student Redbull brand representative was out of town. Second, I called five local Charlottesville vendors but no one could make custom stamps or wristbands within a 12 hour turn-around period. Although the idea was good, I could not afford to chase the rabbit down the hole. As Dale Carnegie once said, “The successful man will profit from his mistakes and try again in a different way.” I had to pivot.

Track record: 0-2.

Lesson 3: If You Talk the Talk, You have to Walk the Walk

The morning of the competition, every competitor met up for lunch to kick off the competition. A first-year whose team fell apart asked to join us. He shared a few ideas with us and we brought him on board. His idea was to sell a bike that fell into his possession. We decided to sell it but we wanted to do it fast, so we came up with a crazy idea: Project36Hours (see below) – “Are people willing to buy a bike if 100% of the proceeds went towards charity and there was a time limit?”


My brother and I spent the entire day building the site, planning the marketing and doing the copywriting. However, we relied too much on our third group mate and we ran into trouble:

1)    The first-year was difficult to reach by phone throughout the day

2)    We were unable to procure more pictures of the bicycle at different angles

3)    Right as we were about to launch the site, the first-year tells us his resident advisor objected to him selling the bike because it belonged to a Brazilian student who left the country but left his bicycle behind.

Not to rip on the first-year but if you talk the talk, you have to walk the walk. He has great ideas and is ambitious but he didn’t prove himself when the time came. Needless to say, we pursued our last idea without him.

Track record 0-3.

Lesson 4: Resources and Timing Will Never be Perfect but You Still Have to Execute

The smart don’t succeed. Those with grit do. We only had 24 hours left to execute and I was about to give up after failing three times. At the 11th hour, I had a revelation. Call it luck but I believe it was a mix of panicking and a bunch of loose ideas pointing to one lead.

Operation “Socialize Cville Restaurants” was born. My brother and I noticed a lot of downtown Charlottesville (Cville) Restaurants  did not leverage social marketing and were missing out on engaging current consumers and tapping into the college demographic. We thus decided to sell restaurants on a Facebook Pages marketing campaign. Our value proposition was: “We’ll build it for you right now in less than 30 minutes. Satisfaction guaranteed or your money back.” Were we Facebook marketing experts? Hell no. We didn’t have all day to figure out how to become experts but we felt we knew enough. Our product wasn’t perfect, we didn’t have the necessary resources and we were running on limited time. But that was the best time to execute because we needed to first seek customer validation.

Lesson 5: Fail Often, Fail Fast and Fail Smart

My hands were sweating when we walked into Zinc because I had never done door-to-door sales before. We made our pitch to the manager but he didn’t bite. We learned that he wanted key metrics such as how much revenue comes from one “like”? He also felt that any tech-savvy individual could do this in his or her spare time. He wanted to keep in touch. Not a win but not a total rejection either.

We next tackled Bijou and learned a crucial lesson. Charlottesville downtown had such strong gravity because it was the town center. Everyone knew about it and would go there regardless and therefore there was no need to engage customers further. Our idea didn’t validate. We soon realized that we were targeting the wrong demographic.

Track record 0-4

On paper, I had failed. I was unable to make any profit. But in my mind, I had succeeded beyond my expectations. I was able to brainstorm, create and execute on four ideas within 36 hours. Although I failed, I failed smart. I learned 5 crucial lessons. I may have made $0 but I can’t ascribe any monetary value to my experience.

This article also appears on timtomblog.com and is published here with the permission of the author
Photo credit: flickr