Who is crazy enough to take a business idea from concept to launch in a weekend? Lots of us, it turns out. And we have a lot to learn from them. Fancy Pants Logo

Startup Weekend recruits a highly motivated group of developers, business managers, startup enthusiasts, marketing gurus, graphic artists and more to a 54 hour event that builds communities, companies and projects. It’s about  networking, team building, learning, and life changes for its attendees and their communities.

As the Indianapolis Startup Weekend website says, “There is a reason that most attendees come back for every event – it’s just plain fun and provides amazing opportunities you can’t get anywhere else. Sometimes a company emerges, sometimes one doesn’t, but every time people leave with more experience, insight, knowledge, friends, and resources than they came with.”

Winning Startup Weekend Strategies for Entrepreneurs that Work, Week in and Week Out

I sat down with this year’s winning team, Fancy Pants, to discuss what they learned this past weekend that they’ll take back to work with them. I also caught up with Denver Hutt, who organizes and facilitates Indianapolis Startup Weekends when she’s not working with other entrepreneurs as Executive Director at Speak Easy, to talk about what she learned this year.

If we learn most when we’re challenged, then I’m sure you’ll agree that Startup Weekend offers a unique kind of learning. Unlock some of that knowledge for yourself below.

How Fancy Pants Won Indy Startup Weekend

Fancy Pants wants you to find jeans that fit, and they know how hard that can be (they have the market research to prove it).

Check it out>> the Fancy Pants product and pitch, as well as the others from Indy Startup Weekend.

In such a short timeline, it’s easy to identify a few things the team did right that really contributed to their success over Indy Startup Weekend:

  • Identified a relatable, wide-reaching pain point
  • Validated their value proposition with consumers and industry experts, then pivoted their focus when they realized that opportunities existed in how they chose to differentiate
  • Spent a lot of time on market research
  • Turned the relatively large size of their team from a potential stumbling block into their most valuable resource

Insights Winning Startup Weekend Teams Bring to Work

We can learn a lot from focusing our attention and energy on just one thing for a short amount of time. When it’s compressed, time can act like a magnifying glass, bringing our challenges and strengths into clear focus.

I asked the whole Fancy Pants team what they learned through their weekend of concentrated effort that they’ll bring back to their regular work with them.

Startup Weekend Work Tip#1: Don’t be Afraid to Throw it All Away

Take the idea on a road show. If you’re getting a lot of overwhelmingly negative feedback, listen to it. We had to pivot in the middle of the second day, and that was when we really started to get it.

Blake Baron, Orr Fellow at Fifth Gear

Startup Weekend Work Tip#2: Everything Has Been Done Before

Just because there aren’t many truly novel, unique ideas out there, that doesn’t mean you can’t be successful and that doesn’t mean you should just give up now. It means you need to differentiate. Understanding what differentiates a value prop is more important than the business model.

To differentiate, the biggest thing we did was look at who our competitors serve. The two main groups they serve that we do not are:

  • People willing to spend more than $100 on a pair of jeans, who can essentially buy their way out of the bad fit problem.
  • Brands, because their solutions tend to limit by company or retailer and are not designed for the end consumer.

Our solution is designed for the end user and we put it in the palm of their hand. Nobody else is doing that right now.

Josh Klaben-Finegold, Orr Fellow at Tinderbox 

Startup Weekend Work Tip#3: Sleep

It’s important to be healthy. Even though you’re running 100 miles an hour, and even though you want so desperately to get everything done, take a few minutes. Get up and remove yourself from the action, because sometimes the best ideas came when we weren’t in the middle of the action.

Amanda Lester, Orr Fellow at Tinderbox

Startup Weekend Work Tip#4: Participate in the Community, Even During a Sprint

  • Practice your pitch. I came into the weekend with an idea to present and it was obvious I didn’t practice building it into a 60-second pitch at all. Others had.

  • The Indianapolis startup community is a family. No SWindy teams shut themselves off to the rest of the community for the weekend.  There was a ton of idea sharing and collaboration all weekend. It was a great atmosphere of helping one another succeed. If you freely share your ideas, others will be glad to repay the favor.

  • You can accomplish a lot when you put your mind to it. It’s easy to view a project at work as a daunting task, but the reality is you just need to put your head down and carve out one late night to make it happen. So much easier than letting the project linger over you for days and/or weeks at a time.

  • Take breaks, socialize and have fun! While there are times to put your head down for one late night to finish a project, don’t force yourself into that over multiple days. About 9:00 or so Saturday night, SWindy folks were getting a bit restless after working nearly 24 hours. One large group split off into a Cards Against Humanity break while others took naps or simply hung out around the Speak Easy. This break not only helped build relationships, but it also kept our minds away from the work long enough to make the late Saturday night working hours that followed more effective.

Jason Williams, Communications Director & Board Member at Centric Indy and US Marketing Director at Keter North America

Startup Weekend Work Tip#5: Take the Time to Reevaluate How to Best Approach your Goals

Returning to work today at the Indy based non-profit Nine13sports, where I am Director of Business Development, gave me a chance to reflect on exactly what skills and knowledge I gained from participating in Startup Weekend.  Given a good chunk of my 9-5 is dealing with grants, donors, marketing and social media it was great to get outside my comfort zone during Startup Weekend Indy and focus on engaging other aspects of a conceptual startup such as market research, demand needed and the pitch concept related to launching such an organization.  This morning I reevaluated several angles of our business efforts to reconsider what and where our efforts should be best used and what information should be updated and utilized to better appeal to our donors and community partners.  It’s easy to forget that constant reevaluation of ongoing materials and services is a key part to staying fresh and relevant in the startup community.  At the end of the day, all the pieces of the puzzle have to work together for a successful result, regardless if that is the physical team and skill set each member brings or the basic concept and product that results from that blend of knowledge.

Tom Hanley, Co-Founder & Director of Business Development at Nine13sports

Startup Weekend Work Tip#6: Don’t Plan for “Later”

The lesson I learned is that we never know what could happen later. At Startup Weekend, teams had to deal the weather and were moved to another place. Luckily, we got 5 more hours. Looks good, but it interfered the tempo. Was it a good thing or bad thing? Maybe we’ll never know.

Yachung Cheng, Graduate Student at IUPUI

Startup Weekend Work Tip#7: Learn from Others with Different Expertise

Startup Weekend Winning TeamStartup Weekend was a great chance to work alongside entrepreneurs with a variety of backgrounds including developers, graphic designers, and marketers. The Kelley School of Business Entrepreneurship program offers a lot of opportunities to work with other business majors, but this event was a perfect addition by allowing people with different expertise to learn from each other.

Max Brickman, Student at the Kelley School of Business, Indiana University

Startup Weekend Work Tip#8: Remember How Team Members Want to Be Communicated With–Especially Under Pressure

One of the most valuable lessons I took from SWIndy that I can immediately apply to the work I do at my day job, as well as the volunteer work I do in the theatre community, is to be aware of others’ communication and work styles when working under pressure. Nothing kills productivity like a frustrated and/or disengaged team member, so it’s important to recognize and delegate based on the value that every team member brings to the project. Our team had a very diverse range of skills and backgrounds, and I think this is something we did very well.

Kayla Hulen, Communications Manager at Diverse Tech Services & Diverse Staffing

Unless you have a compelling reason to change your mind, don’t.

As Hutt explains, teams at sustainable businesses can learn a lot from how Startup Weekend teams must function.

“Unless you have a compelling reason to change your mind, don’t,” She says. Better to simply trust your team’s decision and move forward.

Is Every Weekend Startup Weekend?

A lot can be said for limiting yourself and your team to just a few days to pull something off. We’ve seen great examples of this principle outside of Startup Weekend, too (i.e., Small Box Factory Week).

What have you learned from giving yourself a short runway to take off from? Let us know in the comments!