From CEO to VC: My Trip to the Not-So-Dark Side

After a 25-year career as a CEO, entrepreneur and senior executive, I recently made the jump to the “other side” to become a venture capitalist.

What I’ve discovered in my two and a half years as a partner at Maveron is that being a VC and a CEO are more similar than most people think. Sure, there are major differences—as a CEO you’re in the trenches; as a VC you’re flying at 30,000 feet. But there are also keen similarities. Most importantly, no matter if you’re on the operational side or the investing side, you must love entrepreneurship. No entrepreneur or VC would be successful without a passion for the spark of genius and unbridled energy that every successful start-up has at its core. That’s what separates venture capital from Wall Street and entrepreneurship from big business leadership; both are about making money, but also about fostering innovation.

Let’s talk about the differences between being a CEO and a VC for a minute. The first thing I noticed about being a VC is the longer-term time outlook. When I was CEO of lifestyle media company Olivia, I was focused 100 percent on executing our goals and responding to consumer needs every day. Now, as a VC, I think in timeframes of five to seven years. As a CEO, five to seven years was an eternity! As a VC, I see clearly that that’s how long it usually takes to build a successful, profitable company.

Conversely, if you believe as a VC that a great company will be created in fewer than five years, you will most likely get a bucket of cold water dropped on your head. This is very much a business where you need to realize that sustainable business growth happens “in the fullness of time,” rather than overnight. However, that’s not to say VCs can’t—and shouldn’t—be focused on strategic, short-term execution. I have been trying aggressively to increase the “urgency factor” at several portfolio companies, and I don’t mind rolling up my sleeves, working alongside CEOs and accomplishing operational tasks to speed up progress.

The next big difference between a VC and a CEO comes down to responsibility. As an investor, my role is to influence and mentor—not to run things. That has been a huge adjustment for me, because I love getting things done. I’m starting to see how the active investor role is crucial to the success of a company. But sometimes my entrepreneur DNA kicks in and I have to resist the urge to grab the wheel.

Last but not least, the biggest difference in being a VC is that I now have to be polychromatic—meaning I need to see everything and keep abreast of industry-wide trends. As a CEO, you need to be more monochromatic, focusing on your industry, competitors and vision. As a VC it is critical to spot future trends before they happen—such an example would be Maveron’s investment in Livemocha, an online language learning site that connects learners through the Internet. Livemocha rode the wave of a perfect storm—that of a huge market in need of language instruction, the virtualization of immersion and the social phenomenon that has caught fire online.

I feel privileged to have been a CEO and now a VC. In both roles, I get to think big, spur innovation, launch great companies and generate success for entrepreneurs and their teams. And mostly, I feel that having been a CEO, I understand the challenges entrepreneurs face every day. I strive to leverage my past experience as CEO of two companies in my new role as a VC—helping entrepreneurs see both the wide-angle and focused picture as they build their companies into global leaders.

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