LivingSocial’s Tim O’Shaughnessy: We’re still a giant startup. We don’t have everything figured out yet.

Not only is Tim O’Shaughnessy anti-breakfast, he’s against the traditional take on whether a startup is, or will be, successful. Metrics like capital raised and number of employees hired shouldn’t be the only focus, the LivingSocial CEO and co-founder explained at our Tech Cocktail Sessions event in DC. According to LivingSocial‘s O’Shaughnessy, it’s all about the infrastructure.

“A lot of times people glamorize the number of employees you have and the amount of capital that gets raised, and actually I think it is the inverse,” O’Shaughnessy says. “The perfect business is the one that doesn’t raise capital because you’re not diluting yourself of the your most precious asset as a business, which is your ownership stake. [It’s also] one that doesn’t hire employees before it’s operationally ready to because the tax and the cost on that is really expensive.”

Of course, as we all know, LivingSocial has raised plenty of money. However, “Raising money is a means to an end and not a success, in and of itself,” according to Tim. Instead, it is the operational work, from building out HR and securing office space to time zone challenges and communication hurdles. This is the unsexy part of startup life, yet it is the core of any successful business, no matter what stage it is in.

O’Shaughnessy went on to describe how scaling as quickly as LivingSocial has can challenge even the most well-planned companies. Even though the company was founded in 2007, O’Shaughnessy says, “We’re still a giant startup. We don’t have everything figured out yet.”

Watch Tim O’Shaughnessy discuss the iterations that led to LivingSocial with Tech Cocktail’s CEO and Co-founder, Frank Gruber, in the video below.


Subscribe to Tech Cocktail Sessions on iTunes and never miss a Session – badge_itunes-sm

Did you find this article helpful? Click on one of the following buttons
We're so happy you liked! Get more delivered to your inbox just like it.

We're sorry this article didn't help you today – we welcome feedback, so if there's any way you feel we could improve our content, please email us at

Written by:
Meg Rayford is a communications consultant based in Northern Virginia. She previously spent two years as the Director of Public Relations for a nonprofit startup, where she learned a lot about providing clean water for impoverished countries, even within the confines of a bootstrapped startup. She is the editor of Tech Cocktail, and she develops media strategies for companies in Washington, DC and Virginia. You can read her most recent work in the marketing chapter of the upcoming book, "Social Innovation and Impact in Nonprofit Leadership," which will be published in Spring 2014 by Springer Publishing. Follow her @megkrayford.
Explore More See all news
Back to top
close Building a Website? We've tested and rated Wix as the best website builder you can choose – try it yourself for free Try Wix today