When we think of the Silicon Valley dream, the household names of founders immediately come to mind: Zuckerberg, Page and Brinn, Jobs. Apart from managing huge companies, however, one of the more novel career paths for entrepreneurs moving up in the tech world is venture capitalism: stepping back from direct management to back other entrepreneurs and help them navigate to the same success. Illinois alumni Marc Andreessen and Bill Tai (BSEE ’84) are a few examples.
It isn’t often, however, that once someone has reached this stage in their career, they jump back in the deep end of the pool and start a business. Shawn Carolan (BSEE ’96, MS ’97) took that plunge.
Carolan (find him on Twitter at @shawnvc) is a managing director at venture capital firm Menlo Ventures, leading its investments in Uber, Roku, and Apple’s Siri, among others. Menlo is a multi-stage venture fund investing in seed to growth stage opportunities across enterprise and consumer tech and just raised its 12th fund at $400 million. While helping manage Menlo, Carolan has also devoted himself increasingly to his role as CEO of Handle, a startup he founded while at Menlo after a five-year search for a solution to a very personal pain he had.
Handle, available now on the iPhone and Apple Watch, is a response to the chaos of email overload: it gives customers a tool to obtain and organize what they need without drowning in a sea of information. The result is a user interface that combines a calendar, continually updated to-do list, and emails into one streamlined app to help people stay focused on what matters.
“The way we approached it was realizing the problem was one of attention management,” Carolan said. “At work you’ll get emails that are essentially tasks: do this, get that paper to me, have this done by 4 p.m. Then you’ll get personal emails, like, ‘Let’s get coffee here; haven’t heard from you in a while.’ The question was, how do we prioritize the tasks you need to do and the people you care about?”
Carolan has always been motivated by practicality, specifically in channeling finite resources, time, and effort into creating products that genuinely improve the human condition.
“Something they don’t teach engineers enough is that beyond the skills to build amazing products, you need to think about how the thing you are making will actually change peoples’ days. If the day after they found your product isn’t different, you don’t have a customer.” Carolan said. “Hundreds of millions of dollars can be wasted building complicated products that nobody ends up using. The goal of entrepreneurship is to direct the capital to the people, resources and processes that build something the world really needs.”
From the beginning of his career, however, Carolan has always excelled at balancing the skills he was trained for with expertise he picked up independently. Carolan’s formal hardware-based proficiency is remarkable, as he graduated from ECE ILLINOIS with highest honors in electrical engineering and stayed on with a full scholarship to specialize in computational electromagnetics. However, on the job, he was always drawn to the coding side of computing. While interning at Motorola, though he was hired for hardware know-how, the skills at coding he’d independently developed kept getting him pulled into software side projects that became his main duties.
Carolan’s skill-balancing trend continued when he went into entrepreneurship. Entering business school at Stanford, Carolan had his sights set on the polished desk of a corporate CTO. But upon earning his MBA, he immediately started work as a venture capitalist after an internship at Booz & Co.
Now, he’s shifted gears again: this time, to the much more intimate level of running his own business.
“As a venture capitalist, my first instinct was to solve the problem of email overload by finding a company that was working on it and invest in it,” Carolan said. “That’s the way we work, we seek out promising startups and fund their work.”
However, Carolan couldn’t find a company that embodied the ideal he was looking for, or solved the information overload crisis in as elegant a way. So he pitched his partners at Menlo the idea of him getting the company started and working on it part-time. He has stayed on while continuing to manage investments in Roku, Uber, and IMVU. The majority of his time is spent as the CEO of Handle.
Through every investment managed, project worked on, and milestone of life from writing software at Motorola to finding the love of his life and building a family, he’s grown to appreciate the importance of balancing hard skills with an understanding of the human element. Carolan noted that you can’t be effective in the tech workplace without understanding yourself and the people around you.
“The advice I’d give to any aspiring engineer is to build strong technical skills, of course, but to also invest in your emotional intelligence,” Carolan said. “In working on any team situation, whether you’re leading a newly formed startup or working on a project, you have to understand your own emotions, other peoples’ motivations, and how to listen to what’s on others’ minds so both you as a manager and the company can benefit from everyone’s insights while not wringing each others’ necks. Read books like Primal Leadership with the same ferocity you do problem sets, and learn how to actively seek out and gracefully accept candid feedback.
"In these complicated environments, success or failure hinges on your ability to connect with people and let everyone be their best. Amazing colleagues, which you need to build anything of significance, will not want to work with you if they can't contribute with all they are capable of."