Startup Jackpot Boston Leaves Startups with Valuable Advice and a Shot at Mass Challenge

May 14, 2014

10:42 am

Last Saturday, the grassroots startup competition Startup Jackpot held an event at Boston’s WeWork South Station. Fifteen startups got the opportunity to pitch their businesses for a chance at a $4,300 cash prize, a final round interview with Mass Challenge, and a spot at accelerator Boost. The winner at Startup Jackpot Boston was Drinkwell, which provides impoverished communities with water infiltration systems, bringing clean water and improved lives to people around the world.


The 15 companies that competed in Startup Jackpot Boston.

“My advice to early-stage startups is to keep your targets so high even though they may seem unreachable and you should land close to those targets,” said Jay Singh, CEO of Viral Gains and past winner of Mass Challenge. “You don’t always have to know the exact steps to get to the targets from the beginning. By keeping the target high, you will find the steps if you focus on getting there.”

Prior to the actual pitch portion of the competition, Startup Jackpot invites seasoned entrepreneurs to share personal stories that highlight advice on things such as hiring, scaling, funding, and failure. At Startup Jackpot Boston, speakers included Singh; as well as Greg Skloot, CEO of; Rob Biederman and Pat Petitti, cofounders of HourlyNerd; and Jared Fine, associate at Goodwin Procter.

“If you put a cool tool out there, the market will find uses for it you never considered,” said the founders of HourlyNerd.

Some of the best stories came from Biederman and Petitti. Reflecting back on how they got Marc Cuban to invest in HourlyNerd, they proclaimed: “If there’s any practical advice, it’s to cold-email everyone you can.” Cuban invested in the company as a result of their cold-emailing him about the traction the company was making. With regards to hiring the right tech person, they recalled the story of the lengths they went to to recruit their current CTO, including calling his hotel while he was on vacation in order to decorate his room and deliver a massive gift package. They also offered some advice on VCs:

“Be careful – a VC’s job is to get coffee all day; your job is to get customers.”

“Something to watch for when raising [funding]: most ‘yes’s come quick. If a VC keeps asking for lots of meetings or more and more data, [then] they’re probably not serious.”

The Boston competition is the just the third Startup Jackpot event, with two previous successes in Washington, D.C. and New York City. Cofounded by D.C. native Mack Kolarich, the competition is a way to work with sponsors from the local startup ecosystem to support the efforts of early-stage startups with a no-strings cash prize. With every Startup Jackpot competition, they’ve played around with the model, as – Kolarich admits – they themselves are a startup, interminably iterating and testing. “Right now, every event is different as we’re looking for the best way to scale this model to hundreds of startup ecosystems.”

The next Startup Jackpot event is scheduled for Las Vegas this summer. To find out more about the event or about Startup Jackpot, visit their website.

Tech Cocktail is a media partner of Startup Jackpot.

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Ronald Barba was the previous managing editor of Tech.Co. His primary story interests include industry trends, consumer-facing apps/products, the startup lifestyle, business ethics, diversity in tech, and what-is-this-bullsh*t things. Aside from writing about startups and entrepreneurship, Ronald is interested in 'Doctor Who', Murakami, 'The Mindy Project', and fried chicken. He is currently based in New York because he mistakenly studied philosophy in college and is now a "writer". Tweet @RonaldPBarba.

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