I’m entering year two of my second startup, this time as CEO, and I’ve been thinking a lot about best practices for starting and building a company. I spent nearly a decade working at Google and more than three years at Alphabet’s X, the moonshot factory. There I cofounded X’s first cybersecurity startup, Chronicle, before venturing out and founding Stairwell. Along the way, I learned some important management lessons and philosophies that continue to help me. 


Every CEO talks about having a strong culture and values; but to be impactful, they should be your guiding principles. A light that shows the direction when one isn’t clear. When I joined X, it reminded me of what Google was like when I joined in 2006. X had a sense of empowerment, a sense that it’s possible to actually change the world. When I launched Stairwell, it was with that same sense of purpose and optimism. We did so by defining our core values on day one, before we wrote a single line of code. 

These values became the guardrails of our best selves. One of the most important values we have is “diversity of perspectives.” You need to make sure you have diversity of voice, opinions, and talents to foster innovation and growth. This is an important lesson I learned at X and Chronicle, where we hired a bunch of people from Google. For some of them, there wasn’t a clear enough distinction about what was different from their previous job and culture and the new one we were building. The identity and cultural development that comes from being part of something new needs to be made real. Values need to be reflected in all aspects of your company.


I learned about the power of being bold while working at X and launching Chronicle into orbit. From drone deliveries and internet balloons to wearable devices and self-driving cars, the DNA of X projects is to go bold. The philosophy behind X was refined by Astro Teller, the “Captain of Moonshots,” who came up with a quirky metaphor dubbed #MonkeyFirst to explain why you should tackle the hard aspects of a project before investing resources on the easiest stuff. Specifically, if your goal is to teach a monkey to read Shakespeare on a pedestal, teach the monkey to read first before building the pedestal. This keeps you from wasting time if it turns out you can’t pull off the biggest part of the challenge. 

I applied that mindset here at Stairwell, to how we tackle the problem of cyber attacks for customers. We’ve built a product that has two components— it integrates both external malware feeds and internal security data. It would have been easiest to focus first on one, but the magic is in both components, so we dove in and built them simultaneously. And we’ll continue to apply the principle of MonkeyFirst to every new component. 


During my time at Google, I never met a salesperson because functions were so siloed. This changed when I launched Chronicle, which started inside the strong experimental and collaborative culture at X. It was common for product and sales teams to meet, and this created a more direct feature feedback loop between customers and engineers. At Stairwell, we make that collaboration even stronger. My executive team and engineers are in frequent contact with sales, who are in close contact with customers. They pass requests directly to engineers without going through internal workflow systems. Engineers also interact with customers. We have dedicated Slack channels for each customer where engineers and sales team discuss product features and share threat information. We even integrate user feedback management directly into our platform in a way that is transparent to all users and allows them to upvote other users’ feature requests. 

This helps our product team better understand the target market and customer expectations. For example, the platform was initially built to alert customers to advanced persistent threats (APTs) that had evaded antivirus; but after getting customer feedback through these channels, we decided to expand the capabilities. Beyond detecting evasive APT threats, we now provide customers with context about the alerts they’re triaging from other products, so customers can easily determine whether a file is malicious or not and catch false negatives. 


I advise business leaders to focus on problems over solutions. It’s easy to get passionate about cool technology, but there’s got to be something to fix first. Falling in love with a problem brings opportunity, while falling in love with a solution brings burden. The key is to keep a fresh mindset and look at different ways for solving problems. It’s common for engineers who have spent many months coding a feature/function—maybe engineering a particularly tidy and cool design—to get territorial over the code when someone else tries to change it. They are focused on their part of the solution at the expense of alternative ways that may help the larger team thrive even more. At Stairwell, we aim to keep our sights set on how we can best solve our customers’ problems.  


If you’re relying on positional or hierarchical authority to get things done, you’re not building a team or a culture in which people feel empowered to try new things. For me, one of the most important things for any culture is that childlike sense of wonder. At Google there was a 20% Rule, which allowed employees to spend time on self-initiated projects that weren’t expected to see a near-term financial impact for the company. While it may not be feasible for startup employees to tinker on their own projects during work hours, I try to bring that spirit of innovation to Stairwell. We encourage employees to try new things, even if they aren’t detailed in the product plan. For example, our lead designer recently surprised me with a new UI layout that was an exploratory side project. He had received support from a solutions engineer and a product manager, and when they showed it to me, it blew my mind. It took courage and a level of psychological safety to tinker like that and not feel beholden to what was established. Allowing employees to try something different can improve both the product and company morale.

My experience working at Google, X, and Chronicle was rich with leadership lessons, both ideas that I want to mirror and those that help me choose a different path. Regardless of where I work, I’ve found that having an open mind and being flexible help projects and products succeed.

Mike Wiacek is the founder of security company Stairwell. He honed his threat-hunting skills at the NSA and the Department of Defense, created an intelligence team at Google, and cofounded Chronicle, which was spun out of Alphabet’s X, the moonshot factory.

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