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Early-stage startup CEO 2020 learned lessons


While we had a lot of challenges in 2020, our sense of optimism should never fade. Optimism is about believing in the bright future ahead. That bright future is not possible without acknowledging the past challenges so we can see the road ahead of us. Startup companies are the most vulnerable to external shocks, such as COVID-19. Startups are in this everyday survival and growth battle. We are one of the lucky startups that survived 2020 with a combination of optimism, luck, and making the right decisions no matter how hard they are. I thought of sharing some of my learned lessons as a CEO trying to figure it out.



Never underestimate the power of A+ employees in difficult times.

We had ambitious goals in early 2020 to grow our team by 3X, pivot our product, build 100x scalable systems, and radically change our go-to-market strategy. There were crazy goals given COVID-19 changes and our limited resources. Despite all the uncertainties and challenges, our leadership team focused on only one non-negotiable goal in mind: hire A+ employees. It took us longer to find and recruit the best. When we reached the critical mass of A+ employees, the flywheel effect took place. It paid dividends very quickly. We exceeded our goals in Q4. We see the pace of our progress accelerating every week.


Learned Lesson - the value of your startup stems from who you bring on board. Hire the best employees. Be patient. Your startup progress will eventually accelerate beyond what you initially anticipated. eventually


You don’t solve problems. You enable others to solve them.

I used to be the author of many internal documents. I was fanatical about sharing my thoughts and structured plans with everyone. However, I realized that I’m limiting their perspective. Not sharing my thoughts early in the planning process and enabling them to start from a blank piece of paper was difficult. But to my surprise, the team took off with their ideas and sense of ownership in a short period.


Learned Lesson - Inputs and opinions of leadership should come last. Otherwise, it will be too late to help your team take ownership of the problem and the solution. Share how you frame the situation in your mind, and let them do the rest!


Your startup story is much more powerful than you think.

CEOs owe their teams clarity. Clarity comes from simple and easy to understand story. That story helps each function to derive their voice, tone, and goals. As a CEO, it is easy to get into the rattle holes of execution and daily numbers. Although this is necessary, without a story that guides you and everyone else in the company, everyone will eventually be lost.


Learned Lesson - Have a simple and clear story about why your startup exists. Repeat that story to everyone at every possible chance. You need only a SINGLE story that EVERYONE must be able to repeat and understand.


Adjust your company’s velocity to the market

If you come from a product or engineering background, you might want your technology and messaging to always be bleeding edge. While it feels good to be that advanced and ahead of everyone, it also shows a sustainable opportunity. You might take too long for the market to acknowledge this technology before you can monetize and generate enough business momentum. On the other hand, don’t move too slow with your product and end up with a catch-up race. I’m not talking about the easy to compare the direct competition. The danger comes from the alternatives that your potential customers might have figured out already. These alternatives can significantly lower the value of your product. The reality of your target customers may make your product not relevant anymore. The whole company gets into the catchup mode at this point, and it becomes an uphill battle for everyone.


Learned lesson - If you move too fast, your product and company are likely to be misunderstood. If you move too slow, you will lose opportunities.


Acknowledge macro events and be inclusive

When COVID-19 hit, we experienced a significant shift in the adoption of new B2B products and services. It made our original go-to-market model irrelevant very quickly. We knew that we are still fixing a critical problem. But a different persona and different roles would be interested in it. The team came together, and we implemented a new GTM in less than 30 days. Out of control events, such as COVID-19, will often disrupt your reality. Communicate your perspective as a leader and give the team enough space to figure out how they will handle it.


Learned Lesson - Remember, you are not here to provide a solution to every problem. Your team should work together to figure out what’s next. You only help to frame the problem and to see the opportunities.


Don’t be afraid to be in a different category.

Many companies start with a solution and a market category and end up in a completely different space either due to a pivot, such as Slack and Brex, or due to a shift in the market, such as Uber. It is daunting for entrepreneurs to find themselves re-learning the market, technology, and their target users. As a result, they spend a lot of time resisting evolving the company to be in a different category. As a result, they craft a vague and catch-all message about their company. They end up losing a lot of time and momentum.


Learned Lesson - If you see your company naturally gravitating towards a different category, don’t resist it. Embrace that change and accept the challenge. You might be up to something much bigger than what you originally intended.


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