Baring it all for the first time

Risk, progress and the value of honest feedback for startups

Every Saturday morning I spend four consecutive hours in an aging classroom at NYU’s Metrotech campus with about a dozen of my peers. During this time, our professor, an enthusiastic executive coach with about 40 years of experience, challenges us to become engaging and persuasive communicators, both publicly and privately. He often talks of unbelievable “before and afters”, transforming nervous and soft spoken engineers into powerful public speakers who can easily command the attention of the tech world’s most knowledgeable know-it-alls.

Out of all the tips that you might expect to hear in a public speaking class, one in particular stands out to me. The professor will often end the class by reminding students that enormous progress is possible, but only if they take equally large risks. This piece of wisdom seemed quite obvious at first. However, as I’ve gone about applying it to different aspects of my life, I’ve realized that it is in fact very insightful.

Photo: Vincent Po of TigerLaunch

Last Saturday, instead of going to class, I participated in the regional competition for Princeton University’s TigerLaunch contest. TigerLaunch is a nation-wide entrepreneurship competition that pits student-run startups against each other for about 30k in prizes. Last week’s event included about 30 teams from schools all over the East Coast, but most seemed to be from Princeton, Stanford and NYU.

Each team was given five minutes to pitch, with the judges announcing the top three winners that same afternoon. The organizers are due to announce another handful of winners next week. I don’t expect TrueDiggs to be among them.

While startups of all different stages were invited to participate, the event’s organizers (who BTW did an excellent job) made it clear that the judges would be taking into the account not only the quality of the idea itself, but also the quality of the team and its members’ ability to execute the pitch. In practical terms, this means having a diverse team that includes founders with the technical capabilities to create your product.

My startup,, does not meet this criteria. I am a team of one — most of the technical tasks in building my website have been outsourced. This has allowed me to create and release (very soon) a minimum viable product to test the market before giving away equity or spending out the wazoo. My business plan is solid, but it doesn’t necessarily lend itself to the techie-strikes-rich narrative that many people (including VCs) find appealing.

So why even try? For me, it comes down to taking risks. By “baring it all” — communicating a highly condensed version of my overall business strategy to qualified judges and a crowd of bright students— I expose myself to the type of criticism and feedback that only a stranger would provide.

Let’s face it: the people I interact with on a daily basis are unlikely to point out massive holes in my business plan. It’s not that they can’t, they just won’t. Why make things awkward?

A judge, on the other hand, is paid (or volunteers) to do this. Unlike a mentor, who is more likely to tippy toe around hurting your feelings, a judge is almost guaranteed to give it to you straight….yum.

The people who approach you after your pitch can be equally helpful. One nice girl spent almost a half hour asking me question after question — from how I came up with the idea to the specific functioning of the website. It probably wasn’t her intention to help me, but her questions provided valuable insight into how people perceive my project. These types of bright, inquisitive people don’t come across every day.

In this case, taking risks did indeed lead to enormous progress. I’m no closer to getting off food stamps, but I’ve grown in ways that I definitely did not anticipate. This made it more than worth it.