By Chelsea Rustrum (Entrepreneur, Free Mania)
HoodPerks Team at Startup Weekend6:27pm on Friday night – I arrive at AOL headquarters and I’m greeted by the organizer, Ahmed, who I’d met before. I quickly fill out a “Hello my name is” badge and slap it against my thigh.

The building is open, airy and I can hear the entrepreneurial roar.

There appear to be 100 men milling around, talking in clusters, but I’m so stoked to be there I barely notice the vast gender imbalance.

I simply smile while greeting familiar faces and pushing through the crowd to get to the only other girl I can see, who also happens to be my good friend Breanna from undergrad.

Everyone is eating pizza and drinking Coke. So I grab a slice and a cup, quickly forgetting my promise to ditch soda and eat more greens.

When in Rome, right?

I’d been to several Startup Weekends before, including one in Copenhagen, so I was feeling pretty confident on what to expect.

7:25pm on Friday night – To mix things up and get people talking we do a little improv on business naming and pitching. Some of the most memorable names were ZombieSex and RubyPorn – these weekends tend to be tongue and cheek, so I roll with it.

Next we’re being told to line up for the 60-second pitches. I’m excited to pitch an idea I have had for a while for car sharing using the @airbnb model.

Zipcar works for quick trips, but it doesn’t work for overnight excursions or regular transportation needs. My car sits in a San Francisco parking garage way too much! Shouldn’t it be easier to share my car with someone in my neighborhood that needs to commute regularly?

I’m excited to pitch and yet feel a bit weary. I flip open my MacBook and do a quick search only to find that GetAround has captured a few test markets and now has a calendar function.

Bummer! Good thing I checked.

Time is running out and I want to pitch something original.

I jot down another idea on Bre’s sheet of paper. She looks at me quizzically, but I decide to give it a whirl anyway. I’d already talked to a VC earlier in the week who’d loved the idea.

With nearly 50 people pitching, and only three of them women, it was good news that most of the women pitched their ideas.

In 47 seconds I pitch an idea that targets potential new customers who have recently moved. Why? New residents spend up to 20 times more than established residents and they have a unique set of needs. With this model, new customers would receive rewards before they are even a customer and have the ability to socialize offline with other people in their neighborhood.

After the pitches concluded, everyone gets three post-it votes and to stick on the ideas they like. A web developer from France with some experience in the deals space approaches me. He thinks the idea is strong and I immediately want to work with him.

Breanna flashes me a disheartened look – she doesn’t love the idea, but I’m relieved when she decides to join because I really want to work with her. Now we have two – almost a team!

After selling the idea to everyone who will listen, we get 16 votes – more than enough to be one of the chosen ideas.

As teams formed, we had a total of four strong players join. Our team consisted of two developers, a project manager, a web marketing and analytics guru and myself. Since our team formed so quickly, I was able to snag us a pretty sweet office.

8:26pm on Friday night – I’m alerted that two of my team members are leaving at 9pm to catch CalTrain back to San Francisco. Dang.

We start brainstorming and at first we can’t decide who our customer is: Do we care about consumers or merchants? Can we serve both? If so, who do we target? Just as important, is it technologically possible? Can we get the data we need? Will purchasing the data be cost-effective? And most importantly, do people actually want what we are building? Are we solving an actual problem?

At first I felt like Augusto, a serial entrepreneur from Brazil kept taking us ‘off-track.’ The reality is I didn’t have answers for his questions, which made me uncomfortable. Several hours later, we were still unclear and not in agreement about what we’re doing.

11:15pm – After much deliberation we call it a night. Breanna and I drive to her home in San Mateo and I crash on her couch.

8:21am on Saturday morning – I woke up feeling hectic and anxious. I thought my new iPhone alarm would sound, but it never did so I wake Bre up and we literally rush out the door.

9:17am on Saturday morning – We arrived to bagels and huge croissants. I guess dense calories are cheap. I grab a bagel and head to our temporary office.

A lot of what happens in the next twelve hours can be summed up as market research, brainstorming, team building and dynamic shifting.

As Augusto put it, we storm and then form. He’s a great leader, so he taught us all methodologies of organization, SCRUM and rapid development.

By the end of the day, we decide on what technology to use and how to build the site. JB doesn’t want to use Facebook Connect as he doesn’t see a good reason for it. I do, so I push him a little. With a little mentoring from Augusto, they later get Facebook Connect working and user profile data mapped to our new website. In the end, JB seemed happy to learn how to do this in Python.

2:30pm on Saturday afternoon – Breanna and I decide we really must leave the building and get feedback from potential customers. What we gleaned in the next several hours led us to a dozens of additional questions. The main takeaways were that small businesses are focused on day-to-day operations. Restaurants are willing to try new programs to reach customers, but they don’t want to be bogged down by yet another responsibility or program. Does the customer spend enough in a single sitting to make the discount worthwhile? We also learned that University Avenue is definitely not representative of the typical neighborhood HoodPerks would target. Retailers pay upward of $7.00 per square foot for guaranteed foot traffic, most of which are students and tourists.

5:45pm on Saturday evening – Breanne and I return to the team, very eager to hear what we’d learned. I breeze through the details because I feel like there are more questions than answers at this point.

8:30pm on Saturday evening– JB and Hyacinthe must catch the train again while the rest of us stay and continue to work. JB gets online hours later to Skype with Augusto to collaborate in order to get Facebook to work. JB shows real commitment to the team at this point, which gives me an extra boost of energy.

1am on Sunday morning – We’re still working, but sleep beckons and we’ve stopped being as productive. We agree to reconvene the early the next morning.

1:49am on Sunday morning – As I lay in bed and reflect, I feel defeated. In my mind, we should have built more, done more and started working on something concrete rather than just talking. Even though we did customers surveys, we could have done more. We definitely could have done them in a real neighborhood.

The energy of the group was sinking and I felt responsible. There were too many questions, not enough answers and time was running thin. We hadn’t even agreed on a name.

8:11am on Sunday morning – I woke up with a plan and my subconscious buzzing. I knew what we needed to do and how to lead the team there. Firm decisions needed to be made and stuck to. I was in a different head space which allowed me to be calmer, listen better and help guide us there.

With the consent of the team, I named us ‘HoodPerks’ since we’re offering rewards to consumers based on what’s available in their neighborhood. In short, new residents get free stuff based on who they are and the fact that they’re new to town. In return, restaurants, gyms, bars and salons get a guaranteed new customer who is likely in discovery mode, looking for new local favorites to return to.

By being clear and better communicating our vision, we start working like an A-Team – even lunch breaks were spent hustling.

Augusto and JB were able to sort out the development and design and Hyacinthe created us a compelling logo, while Breanna and I discussed the presentation.

Working with Breanna was interesting because we’re such longstanding friends; I think I shut her down and didn’t listen as well as I could have. I’d later recognize that and apologize.

Toward the end, Breanna loops Rebecca in to help us. Rebecca is awesome because she’s worked with a bunch of startups in accelerator programs in Copenhagen get funding and sort out their strategy. She comes through as a beacon at the eleventh hour.

5:01pm on Sunday afternoon – Ahmed alerts us that it was time to start the pitch ceremony. We are clearly not ready for prime time. I was told we had until 5:30 pm and it was only 5 pm. Definitely a “yikes” moment. The slides weren’t ready. I hadn’t practiced. I didn’t even really know what I was going to say. My team fled and I stayed in our office to finish and practice our pitch.

I was relieved when Breanna came back and acted as a sounding board. On the first run, the presentation alone was 9 minutes before even getting to the demo.

6:15pm on Sunday afternoon – JB came in and said we were about to be up. I cringe and delete a few more slides per Breanna’s recommendation. We practiced once more before we headed to the main hall.

Ahhh, they were passing out beer. I down a Stella and head for the stage.

7:20pm on Sunday afternoon – As I approach the front of the room,.. I feel a strong sense of pride in what our team has accomplished and the responsibility to be bold, confident, passionate and articulate. I finally knew what we were doing and why, so I spoke with conviction.

The presentation was 4 minutes and 52 seconds out of the allotted time of 5 minutes. The judges asked a few good questions, which I had excellent answers for thanks to all of the brainstorming and customer research we’d done.

Getting off the stage was even better than pitching. We had a moment of hugging and smiles followed by a lot of praise and feedback from others in the room. People kept saying “good job,” “I liked your pitch” or my personal favorite: “that’s a good idea.”

The final judging came and went without fanfare. I think we had one of the strongest business models, but other teams had built some interesting whiz-bang software that blew everyone away. I like winning, but even more than that… I love the process. Ultimately, our idea didn’t win the day.

Breanna asked “aren’t you disappointed we didn’t win? Doesn’t that say something? “Maybe it’s the rebel in me, but I don’t think it means squat. The real test is actually doing business. We’ll try a pilot market and see what the feedback is. In some ways, the only way to know is to actually test an idea.

Join me at Startup Weekend this September

Ladies: there were only five women out of 130 people at Startup Weekend, which represents 3% of the total participants.

Let’s represent at Startup Weekend this September!

The weekend gives you a birds-eye-view into the mechanics and reality of building a startup. Plus, you’ll get exposure to mentors and potential investors just by being there. There’s no better education than actually going through the process and working with a team.

If you’re even thinking about attending, this is a huge opportunity for you to stand up and stand out.

Will you join me this September 9-11 in Mountain View? I’ll be there helping with the event as well as participating.

I’m told Microsoft is footing the bill, so the venue will be nice and gourmet options are on the menu. Plus, this is going to be the biggest Startup Weekend ever.

Editor’s note: Got a question for our guest blogger? Leave a message in the comments below.
About the guest blogger: Chelsea Rustrum was born into entrepreneurship and grew up in family business. She started Free Mania a free stuff site when she was 14. Among the many hats many hats she wear, strategic marketer and community builder seem to stick. Chelsea has enjoyed the freedom of coworking and working remotely for the past several years in places like Thailand, Australia, Indonesia and Italy. Now, she’s looking to combine the power of travel, collaboration and team building, thus Startup Abroad. Follow her on Twitter at @mktgchelsea and read her rants on NoTopRamen.