Are You Ready to Start a Company? Ask Yourself These 6 Quest…

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Adapted from Crack the C-Suite Code: How Successful Leaders Make It to the Top, by Cassandra Frangos, copyright 2018. Reprinted by permission of Wharton Digital Press.

Amy Chang, former head of analytics at Google, was just two levels removed from Larry Page and the C-suite when she stepped away from her role at the search giant to co-found Accompany, the venture-funded digital personal assistant startup. This move epitomizes the experience of a unique set of aspiring leaders — when they are ready for a top leadership experience, they create one for themselves.

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Becoming a founder can be seen as an expedited path to the C-suite, whereby leaders sacrifice a large measure of security to create something all their own with a team of like-minded partners. Those who follow the founder path in order to lead an organization stand apart because they actively create their own opportunities, and therefore have greater control over the timing of their career advancement. But, how will you know if (or when) this particular path applies to you? According to the executives I’ve worked with and interviewed, six key questions help determine your fit as a founder.

Am I having the impact I want?

Entrepreneurs are an upbeat bunch. Few of the founders I have met left their executive positions because they were unhappy. In fact, most loved what they were doing and were extremely successful. In some cases, they would have reached the C-suite in their organization eventually. But, in each instance, they wondered: Can I have a greater impact out on my own?

Erik Larson was a senior director at Adobe Systems before he launched Cloverpop, an online business software that uses behavioral economics to guide better and faster decision-making. Larson said the idea of building a business had captivated him for years. “It was always something I knew I’d do,” he said. “But, even more, I found it amazing to think about creating a business that employed people and generated real value in the world.”

Similarly, Christopher Wu left Snapfish to co-found Paper Culture with two goals in mind. “We wanted to build a great business, of course,” he said. “But, just as important, we wanted to make a difference across many different dimensions.” For Wu and his founding partners, that meant having a positive impact on the planet and raising awareness for climate change. As part of that purpose, Paper Culture plants a tree for each order fulfilled.

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What problem will I solve?

The entrepreneurs I spoke with said their ventures sprung from a desire to improve how they and others around them worked and lived, and to solve a particular problem or fill a void. Larson said the idea of using behavioral economics and science to improve decision-making was “an idea he couldn’t let go of.”

Yet, even beyond any specific idea or execution strategy, many of the founders I interviewed said they were motivated to solve a particular problem.

Susan Marshall is a case in point. She was the senior director of product marketing at Salesforce before she became a founder. The entrepreneurial light went on in Marshall’s head one day when she was out on the road talking to customers and hearing about the same unsolved problems over and over.

Marshall surmised that if she could solve their problem and help them be successful, she would also be successful. With that in mind she launched Torchlite, a software and services solution that helps marketers get more done by connecting freelance talent, campaigns and marketing technology into a single campaign management platform.

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Who are my co-founders?

Taking your potential co-founders and their skills into account can get you closer to deciding whether the entrepreneurial path to the C-suite is right for you. Perhaps the most important assets co-founders deliver are experience and contacts that supplement your own.

Chang founded Accompany with several partners, including the former CFO of Ning, Ryan McDonough, who moved over to become Accompany’s CFO. She also brought on a best friend and fellow Googler with considerable technical chops to serve as her chief technology officer (CTO). One of Wu’s co-founders, Anurag Mendhekar, was a former colleague from his earlier stint at Yahoo and a startup CEO at several previous ventures. Mendhekar assumed the CTO role at Paper Culture and is a mentor to Wu, who is the CEO.

Several of the founders I spoke with said their co-founders “served as sounding boards” and offered an “objective reality check” early on about the viability of the business and the likelihood for success.

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Am I staked financially?

For most top executives, choosing the founder path requires a personal fiscal sacrifice associated with leaving a high-paying executive position to go out on their own. Cloverpop’s Larson put it this way: “The financial question is probably the most important. No matter how long you think it’ll take to be a viable business, you need to be ready for it to take five times longer.”

Another founder told me: “I walked away from an annual million-dollar salary to make nothing at first and then pay myself maybe $90,000 annually.” Yet, today, he’s on his sixth startup as CEO.

The founders I interviewed all had some type of financial cushion when they were making their move: personal savings, a spouse who was gainfully employed or financial liquidity following an exit from their previous position, for example.

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Do I have the personal support I need?

The importance of personal support can’t be overstated along any path to the C-suite. Reaching the highest levels of leadership is difficult and stressful no matter how one arrives. That said, the lack of institutional infrastructure — benefits, training, salary — in startup environments means an executive’s personal support network must be especially strong. Personal support comes primarily from co-founders, friends and family, and its uplifting impact is undeniable.

Chang said that without her husband’s moral support she never would have had the courage to leave Google. Larson told me that his wife’s encouragement and her own extremely successful career made it possible for him to take the leap.

What will I do if I fail?

One thing is certain if you choose the founder’s path: You will fail at some point. Maybe not initially, and maybe not ultimately, but there will be a time (and perhaps many times) when you fail in some significant way.

Unlike the other paths to the C-suite, the founder’s path involves frequent failure, which means you need to determine whether failure and reinvention is a realistic option for you. Search yourself and decide how you would fare if you fail. Will you reinvent yourself? Pivot? Recommit and forge ahead? Change paths? Regardless, ask yourself the question and envision what your next move would be.

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