Working with early-stage startups simply isn't for everyone. Throughout my career, I have worked, consulted, advised, and even invested in a multitude of budding companies. Some saw success, while others fell flat on their faces.
Despite the fact that startup job recs bear a close resemblance to roles at larger organizations, startup life is rife with many business abnormalities that aren't ever outlined in a manual or discussed in entrepreneurship workshops and classes. Tech startups, in particular, are commonly misclassified as operationalized offices with boundless perks and lucrative opportunities for equity.
Oftentimes, I interview people from larger organizations or straight out of college who have been deceived by notions of startups life classifying it like some get-rich-quick scheme. Many of those individuals fail to truly understand what is involved in building a business. They fail to comprehend the difficulty associated with transforming a great idea into a functioning business.
My previous CEO and serial entrepreneur, Bill Lee, once said, "running a startup is like eating glass and staring into the abyss. If you are wired to do it, then only do it, not otherwise." Bill's good friend, Elon Musk, later concurred with his brutal reality of entrepreneurship.
Jet Skis and Cruise Ships
Whenever I interview someone who is taking their first swing at startup life, I like to share the following analogy:
Working at a big company is like riding aboard a cruise ship. You have every amenity and every tool you need to get your job done at your disposal. The ship may even be set to run on autopilot. The ride is often relatively steady. You don't feel the rough waters unless you fall overboard of hit a metaphoric iceberg.
Startup life is different. Working at an early-stage startup is like riding a Jet Ski. It is exhilarating. You will feel every wave, every bump. You must move fast in order to keep up, but you can, in many ways, forge your own path. Your tools are very limited. You need to constantly be aware of what you have and what you do not. Contingency plans are built around these limitations and, more often than not, strategies rely on creativity instead of following pre-structured best practices.
Managing the Pack
For management, startup life is even more complex. If hiring is done right, these offices are filled with highly ambitious, creative, hard-working individuals who thrive when coloring outside the lines. But keeping everyone moving in the same direction is no small feat. In the early years, your team on Jet Skis can easily wander, veering too far left or right. Keeping everyone moving in the right direction and focused on the same goal is often the biggest challenge.
The rate of scaling is also commonly overlooked and underappreciated. A company can double, triple, or even quadruple in size in a year. This adds a lot of stress to the business, and to the people. As Bob Sutton, a professor at Stanford University, states, "as an organization grows, whether you like it or not, it will require more hierarchical layers, managers, rules, and (often) annoying administrative processes. It will also become increasingly difficult to maintain personal relationships with all your colleagues."
Scaling represents an incredibly complex problem that management rarely recognizes or appreciates in the early years. Scaling, as Sutton put it, is always associated with growing and getting bigger. It is one of the success indicators that attracts people to the startup world. But scaling a business at the rate that is required in the early stages in order to be competitive leaves a business with potentially crippling culture problems.
As scaling occurs, the strengths of relationships between management and employees changes. Just when you achieve alignment, new members are dropped into the team. Again, refer back to the metaphor of riding in a pack of Jet Skis. It is so much easier to keep five or ten people headed in the right direction without crashing as compared to 30, 50, or 75. Soon enough, you need to upgrade to motor boats. The freedoms, liberties, and fun of surfing the waves in autonomy are replaced with speedboat captains who are in charge of the plans and path ahead.
Culture also often shifts quickly as you grow. Many startups focus on a short list of values and key terms in order to ground the company during rapid expansion. But culture isn't really an about words or phrase. It's about how people feel when they walk in the door and how they feel when they walk out. Exhaustion is common and ok if it is coupled with a sense of accomplishment and empowerment. Companies that lose sight of this or re-prioritize are left with heavy churn and a sour reputation as a toxic culture.
Not For "You"
Conquering these challenges is how the best startup executive thrive. One of the most important things to remember is that startup life is not just "for you". You have to have a "team" mindset. It's about putting egos aside and focusing on collaboration and compromise. This is easier said than done. Execution is a major challenge, especially given the degree of difficulty involved in hiring experts in things like collaboration. Resume bullets can't sniff these traits out easily and anyone who bluntly claims they are collaborative on their resume might as well also state they are also proficient in Microsoft Word.
So why is the ride so attractive? Why do so many of us endure the long hours, bouts of anxiety and the perpetual glass mastication? For those who put in the time and commitment, startup life can be utterly rewarding. Working alongside brilliant individuals and solving problems that don't have a Google-able answer is half the fun. Never does your brain go numb, unless you end up having to do a task that an intern would do if you could afford one.
For me, it is all about the people, the pace, and the creative process involved in constant problem-solving. Limitations can foster the best ideas, but you must get comfortable with the uncomfortable. For those that get seasick at the thought, early-stage startup life might not be for you. For those that love the adrenaline rush, climb on board.