Meet Scott Holloway: 2nd Place Winner at Startup Weekend Chicago

So many of us have ideas stuffed in our brains, sock drawers and wallets. Problem is, most of us don’t have the resources, time or assistance to turn our ideas into businesses. Enter: Startup weekend. Last month, Scott Holloway walked into Startup weekend alone, armed with an idea, looking for possible team members to help him bring his idea to fruition and create a business. 54 hours later he left with a team, business plan and a 2nd place finish.

In our conversation, Scott details his experience at Startup weekend, the challenges he faced and how his idea evolved and pivoted during this brief, titillating 54 hour period of time. Below is a record of our conversation:

1. For starters, for those who don’t know about the event, what is the idea behind Startup weekend? What function does this event serve for those looking to turn ideas into businesses?

Startup weekend is a 54 hour event where a group of passionate businesspeople, developers and designers come together to bring an idea into a reality and make a business in a weekend.

How it works is there is a group of non-technical people, as they’re called, who are business people and marketers, which was my title throughout the weekend and then you have developers and designers. Through a process, teams are formed on the first night and then it’s up to those teams. The rest of the weekend is formed during a pretty relentless and tireless 54 hour weekend to create what Startup weekend refers to as your MVP, a Minimal Viable Product, and present to a panel of judges on Sunday evening.

In terms of bringing ideas into real businesses, it serves an incredible function. The idea that won Startup weekend came from a girl, who worked in the hospital industry. She had this big business plan and she believed in an idea but didn’t have any way to execute on it. She found this medium, Startup weekend that allowed her to bring that to fruition and her team won. Most people didn’t come in with business plans and just kind of came in with an idea. She had this idea, did a bunch of research and this was one of the ways where she thought she could make it a reality.

2. Why did you attend Startup Weekend Chicago and why did you attend the event alone?

I attended Startup weekend, because I think, like a lot of people, I am very, very passionate about business and I feel like I have a lot of great ideas. I have always wanted to do something on my own. Not having that very technical background of being able to write code or build my own mobile application at this point, I wanted to find a medium to be able to do that. I found this event, Startup weekend and I thought it was a fantastic way to see if one of my many ideas had legs, to see if it was viable and more than anything understand the process of how to bring an idea to reality. That’s something that I think is extremely valuable.

The project management skills you learn in a weekend and the ability to focus on the core aspects of a product are unbelievable. The people you meet at Startup weekend…that’s another reason I did it. I wanted to meet people and you ask why I did it alone: I would recommend to anyone going to Startup weekend. Just go it alone.

 I benefitted from that immensely and I would recommend that to anyone. I had a fantastic experience because of that, because I forced myself to network as hard as I possibly could and build a team around me without already having a base of friends around me who are coming to join my idea. I didn’t want that.

3. How did your idea develop during the weekend? How did your idea pivot and change and develop a life of its own during those 48 hours?

That’s something that’s very big at Startup weekend. You will hear the word pivot a bunch along with MVP, Minimum Viable Product. It’s crucial. We pivoted a ton and that’s because it was my idea and they were working on it. You have this grandiose thought in your mind about how this is going to become a company and all the different features of it and how you are going to create value for users and consumers. It’s not feasible to do all that in 54 hours. There are extremely talented businesspeople, designers and developers but there’s only so much you can do in a weekend. What happens is you take an idea and nail down the absolute core features that are necessary.

You have to ask yourself, “What are the judges going to pick at?” They’re going to pick at this and ask how we are going to monetize this aspect of our idea. My idea was a social exercising platform. I realized the best monetization strategy was based around corporations. We had to pivot 30 hours into the weekend and focus more on the corporate side of it because that’s what was going to be able to monetize the app. You will find yourself during the weekend, asking questions, “Is this absolutely necessary to have in the functionality this weekend?” Because you want to be able to present to the judges something that is at least functional. 

4. What is your idea?

The company is called ExerSocial. It is a mobile running application that allows users to create custom running races anywhere in the world with their friends. If I’m in Chicago, and you’re in New York, we could create a race from, for example, Rome to Florence. You run on your own schedule in NY, and I in Chicago. We track our virtual progress in real time and see where we are at amongst our competitors. You can create a custom race by dropping two pins on google maps within the app, or choose one of our races of interest that include the Great Wall of China and the Boston Marathon.

We plan to monetize the app by structuring corporate wellness initiatives and employee races for Fortune 500 companies.

5. What was the most challenging aspect of Startup weekend?

There were two things that were most challenging to me. One: focusing on the core elements and making sure that we had three key features functioning by the end of the weekend. But also, organizing everyone around your vision. At the end of the day, these individuals are excited and they chose to work with you on your idea. You want to make sure that you help orchestrate that vision and don’t stray away from it. You kind of have to do checks every couple of hours, “Look where are we at, are we still focusing on the core elements?”

The idea behind my app was competition and we had to ask ourselves, “Are we getting away from that?” We wanted people to compete with one another to be healthy. That’s something that’s very challenging because your designers are going to be off doing design work and your developers will be banging away coding and your fellow businesspeople will be calling on people for opinions and going out and doing market research in their field. You have to make sure you’re core-knitting well so that one part of your team isn’t working toward a different goal. Everyone is working hard and there is just not enough time, a lot of the time, to make sure everyone is on the same page.

You’re not completely on your own here. There are volunteers. These volunteers are mentors, they are fellow entrepreneurs, they’re people who have been through Startup weekend and they’re CEO’s of startups and they are walking around and basically will spend 5 minutes with you at a time. You get 30 minutes the whole weekend with a combination of these people total and those 30 minutes are invaluable. They are able to dissect what you’re doing, able to help you focus on the right things and provide you direction about what the judges are going to be looking for and what’s important to your Minimum Viable Product.

6. Do you plan to attend a future Startup weekend?

I do. I still am working on what happened from this past Startup weekend. I had such a fantastic experience that I certainly plan to attend another Startup experience. I’m not sure in what capacity yet because you can attend as a volunteer but I am definitely going to attend another one.

7. Now that you have been to one what’s the best single piece of advice you would give to anyone considering attending one of these events?

If you’re considering attending one, I would say absolutely do it and do it alone and go in with an open mind. You’re going to get so much out of it. I was on the fence up until 48 hours before going to this and I said to myself, “I’m just going to do it and I’m going to go 100% and I really benefited from it.” If you’re on the fence, don’t be, it’s an incredible experience. You’re going to learn so much. Go in there and do it alone.

8. What’s one thing you would tweak about the current format of Startup weekend?

There are 7 or 8 teams that will end up getting some sort of prize at the end or get some sort of award. I think this could be a little better structured and communicated because it was a little ambiguous at times. In terms of the actual structure of the event, I think it’s great. What you’re able to do in 54 hours is pretty awesome.

9. How did you do and where do you go from here? What are your next steps for the idea that you hatched at Startup weekend?

I was fortunate enough to get 2nd place. There are fantastic prizes. We were awarded a booth at Tech Week Chicago and awarded a month of office space here in [Chicago]. Our next step is staying focused and basically trying to bring this mobile application to fruition. We still meet on a weekly basis. My team is dedicated to bringing this app to reality. We have a long way to go but we’re really enjoying it.