Last Saturday, 15 local startups crowded WeWork’s South Station space for the chance to win a slew of prizes and some serious dough, no strings attached.

And no, it’s not too good to be true: Startup Jackpot held its third-ever pitch event in Boston last weekend, calling upon the Hub’s bootstrapped startups to share both their stories and growing pains without the sugar coating.

The Washington D.C.-spun grassroots organization aims to give young companies a small cash infusion to meet their next milestone in the interim before either folding or going on to raise more capital.

Prizes up for grabs among Boston’s batch of early stage companies were $4,300 in cash, a final round interview to MassChallenge and a spot in startup accelerator Boost.

Before the pitches got underway, five members of the innovation ecosystem – Greg Skloot of Attend.com, Jay Singh of ViralGains, Jared Fine of Goodwin Procter, and Rob Biederman and Pat Pettiti of HourlyNerd – gave the founder-filled crowd a few pieces of advice on scaling, funding and failure.

“Keep your targets so high – and even though they may seem unreachable – you should land close to those targets,” viral video marketing startup ViralGains’ Singh said on Saturday. “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.”

Another pearl of wisdom came from the two HourlyNerd founders present: “If there’s any practical advice, it’s to cold email everyone.” Biederman and Pettiti recounted sending an email to Dallas Mavericks owner and Shark Tank investor Mark Cuban. Impressed with the MBA student consulting startup’s traction, Cuban soon became an investor in the company’s undisclosed Series A.

With advice imparted, the 15 entrepreneurs took their turns pitching the audience on their companies and respective plans for the Jackpot’s bounty. In the end, only three could walk away winners (pictured above).

Taking first place and the Jackpot was DrinkWell, a startup that empowers impoverished communities with water filtration systems, bringing clean water and a better life to 200 million people around the world. According to its calculations, the champ will be able to use the cash to provide 10,000 people with clean drinking water.

With 200 profitable deployments across India, Laos and Cambodia through local partners, Drinkwell Systems’ water filtration tools deliver 60 times more water, is 17 times more energy efficient and reduces waste by seven orders of magnitude compared to reverse osmosis, the current best practice. 

Second and third place were stolen by secure email provider ProtonMail and elderly tablet technology GeriJoy.

Headquartered in Switzerland, ProtonMail offers end-to-end encrypted email. The company, which was a semifinalist in MIT’s $100K Pitch Competition, intends to keep the product forever free and users fully anonymous. Because DrinkWell already conducted a final round interview last week with MassChallenge, ProtonMail received the opportunity to pitch to the Seaport accelerator’s selection committee. 

GeriJoy bills itself as a “compassionate and cost-effective companionship and oversight, 24/7” for the elderly individuals afflicted with dementia. The startup uses tablets – or virtual senior care companions – to give caregivers help and comfort their patients and loved ones.

Congrats to all the companies that competed in Boston’s Startup Jackpot!

Images via Startup Jackpot