My weekend as an entrepreneur

We asked Upstart NY writer Allan Mendoza to participate in Startup Weekend and share his three-day experience as an up-and-coming entrepreneur.

Day one

Going in, I know this weekend is going to be more Iron Chef than Shark Tank or The Apprentice, because each team will have to scramble to get their idea ready to pitch by Sunday. While it’s possible that viable companies could come out of this weekend—and according to organizer Matt Hostetler, they have—that’s not the point of Startup Weekend. It’s an educational and networking opportunity; but for me, the main draw, and the reason for my participation, is the frantic, creative energy, the all-hands-on-deck mentality that makes working at a startup worth all the stress and aggravation.

I was recruited to the team working on ThirdStor3y, a commercial real estate marketing platform that focused on connecting buyers with sellers on a deeper level than other real estate sites and caters to a growing, but underserved tertiary commercial real estate market with a back-to-basics approach. Maggie, who pitched the idea, was a commercial real estate agent and knew what her target market wanted, as well as what weaknesses the competition had. She clearly did much of the groundwork that would give us a major head start in the days ahead.

Although only about 10 % of the participants were coders, our team fortunately had two: Maggie’s friend Lizzie and Kai, talented developers who were responsible for some late-night coding magic that often seemed impossible due to the time constraints.

On the non-technical side, our team had Aidan, a student working on a master’s degree in organizational leadership, and Michael, a veteran business development consultant. I offered my services as a digital marketer with some basic graphic design, product development, and UX/UI experience. It became clear, as we worked together, that if we had to form a company with the team we had, additional hiring would be minimal.

We settled in the middle “birdcage” in the Dig co-working space on Buffalo’s East Side, and broke into two groups--one technical/creative, one business--and started brainstorming. I sketched out a rough wireframe of what the app could look like, anticipating that we would work on an interactive demo that would simulate a mobile app. But Kai had bigger plans. He wanted to make an actual, functioning webpage, using a for-purchase template. Lizzie, who specializes in graphic information systems, geeked out over the prospect of customizing the mapping system, and Kai listed endless ways to customize the page.

Whether by inertia or quiet consent, I found myself acting as a go-between, making sure the business aspects aligned with what the technical/creative team did, and suggesting that certain ideas be dropped due to time constraints. I’ve seen what feature creep can do to a product over the course of a year, much less three days. Looking back, I might have been a little too restrictive because I didn't want to let my vision of the product go, and I didn’t know what everyone was capable of.

As 10 p.m. rolled around, we all decided to call it a day. I felt a bit guilty—we left relatively early, as most of the other groups stayed until 11 p.m. But I brushed any worries aside; it seemed clear that we had a solid plan to move forward.

Day two

The second day was surprisingly quiet, and that’s because many of the participants never came back. Kai explained that this happened last year, too, because some participants want to work only on their own ideas. It’s hard to fault them—many were looking forward to this weekend to work on projects they’ve thought about for months or longer.

My first task of the day was branding. After a vote on color scheme—several shades of green--I began work on a logo. A $50,000, focus group-tested, branding project this is not, so I threw together a Word document with a few very similar looking variations, using fonts that suggest “business,” “forward thinking,” “slick.”

This was probably my single most important contribution to the project. With the exception of my content and social media marketing chops, which were used minimally this weekend—I was pretty much a jack-of-all-trades, helping out where I could: writing copy, market research, guiding design for the site, etc. I was far from useless, but I didn’t have Maggie’s and Mike’s business experience, nor the coding skills to contribute substantially on the technical end.   

Throughout the day, coaches, including a lawyer and local entrepreneurs, visited us. Our business model held up to scrutiny, and the biggest error we made was forgetting to include a revenue stream in our calculations. But it was a welcome mistake--instead of one or two years in the red, our model predicted ThirdStor3y being in the black from the beginning. Also welcome was the valuation of $80 million. Although it was a hypothetical number, we couldn’t help but get goosebumps thinking about it.

After a late-afternoon break, we returned to our space in Dig and started work on adapting ThirdStor3y to a data-centric model in response to coach feedback. It was the exact model we tried to avoid in the first place, but it made sense: We need a reason for customers to come to the site and subscribe. We’d still maintain the desire for better, more transparent data, as well as a focus on more personal, on-the-ground relationships, however. This pivot made ThirdStor3y less disruptive, but sometimes it’s easy to forget, in the passion of wanting to change things, why certain business models persist.

Day three

The day began like the previous night ended--Kai and Lizzie worked on finishing the demo, which now had real listings for Buffalo, Rochester, and Syracuse, thanks to their late-night, early-morning efforts to gather, process, and implement the tens of thousands of data points for properties. Mike and I cranked out a search engine optimization and social media marketing plan, more of my forte.

After a couple of hours, we began to focus on the presentation and test the website. The judges would consider each idea from the perspective of a potential investor, so minor holes in the business plan or even a lack of confidence during the presentation could be viewed as damning weaknesses. Along with anticipating tough questions, Maggie had to be prepared to avoid triggering certain questions--no one can answer everything, and there’s also the risk that a line of questioning will inadvertently derail the narrative’s focus from our strengths to our weaknesses.

At 4 p.m., we took our seats for the pitch, and Maggie reviewed her talking points on her phone. When it was our turn to present, we stood in front of the crowd as a group. Maggie gave a solid, impassioned performance that was more TEDTalk than sales pitch. Our fully functional demo, one of only two, had the desired effect to shock and awe the audience. I was convinced that we had a winning idea.

During the Q&A, one of the judges remarked how well this product could scale. But another asked an unexpected and very specific question about market demand, which caused Maggie to stumble for the first time during what otherwise seemed like a perfect pitch. Despite a less-than-confident delivery, she managed to draw from her experience as real estate broker to provide, in my opinion, a decent, educated response. Putting things into perspective, this little trip-up didn’t seem to be a big problem, as most of the other teams struggled with judges’ questions and often, were not able to answer them at all. When the judges left to make their decisions, we still thought we were a shoe-in for the top two spots.

The announcement of who won was anti-climactic for us. We placed third, and most of us were disappointed –our hopes were dashed.

But we couldn’t be too hard on ourselves, or discount how much luck factored into the competition. What if Maggie’s idea didn’t make it past the first round? What if we had no coders at all? Might we have won if the judges had more of a real estate background and could better understand the potential value of Third Stor3y? Would a different panel of judges have given us a top spot? We’ll never know for sure.

But what we did know now, after 54 hours of intense planning and hard work, was what Startup Weekend promises: “..the highs, lows, and pressure that make up life at a startup.”

Read more articles by Allan Mendoza.

Allan is a writer, editor, and digital marketer. Prior to moving to Buffalo, he worked for various marketing agencies, nonprofits, and tech startups in the New York City. He also currently serves as managing editor for Karibu News, a free biweekly that covers immigrant and refugee issues in the region. An avid outdoorsman, he spends his weekends either hiking or cycling and, in 2013, hiked the entirety of the 2000-mile Appalachian Trail.
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