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Spend time around any new startup and there’s one phrase you’re sure to hear again and again: “if only.”  If only we had more money, if only we had legal advice, if only we had a well-established mentor, if only we had another developer, if only, if only…

No one will argue against the fact that bootstrapping startups face numerous obstacles, particularly at the earliest stages.  Instead of viewing these constraints as hurdles to success, Adam O’Neill, COO of Rentabilities, urges young startups to view these hurdles as opportunities.  O’Neill believes that “…constraints save start-ups.  They force creative problem-solving and thrift.  They enable more meaningful development of relationships,and preclude costly mismanagement of resources.”

Under the leadership of CEO/Founder Alex Cook and Chief Tech Geek Andy Cook, Rentabilities has turned constraints into opportunities for creativity and out-of-the-box thinking since 2006.  The company is an online marketplace and software solutions provider for the rental industry.  Rentabilities moves beyond a purely online presence by allowing brick-and-mortar retailers a POS cloud-supported website-integrated software system.  The true value in Rentabilities’ offering is that it allows retailers to synch their POS system with an online platform customers can see in real time.

The power of the team’s positive thinking is persuasive.  Rentabilities recently received one of the top prizes at MassChallenge, a program supported by Startup Weekend. Selected from a pool of 450 teams representing 26 countries and 24 states, the team pitched to a panel of judges and was among the 110 teams given three months office space in downtown Boston.  During that time teams were paired with mentors and given access to resources within the Boston ecosystem and beyond.  Even in this environment, O’Neill says he learned something about attitude and constraints; “Mentors who view constraints as beneficial tend to relate better with startup founders and offer advice that is more timely and actionable.”

In the end, Rentabilities won $50,000 at MassChallenge.  The team plans to use the prize money to focus on a six-month push to get Rentabilities into the hands of the retailers who can most benefit from it.  The Cooks and O’Neill know that the win at MassChallenge crossed a few of the most pressing “if onlys” off the list, but that sustainable success lies in nimble problem solving when faced with new constraints down the road.

Startup Weekend was a 2010 partner organization for the 2010 MassChallenge.  MassChallenge is a global startup competition and accelerator.  The competition is open to any entrepreneur, anywhere in the world, with great ideas and a passion to transform their vision into reality.  For more information about MassChallenge and to register for the 2011 event, follow the links.

Rentabilities team (L-R): Adam O’Neill, Alex Cook, and Andy Cook (and their giant check!)

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