Lessons for a Startup CEO

Startup CEO

03 Jun Lessons for a Startup CEO

Being a startup CEO isn’t easy. As the old saying goes, if it was easy, everyone would do it. Despite how it sounds, it’s not a glamorous position and in fact most of the time it is the exact opposite. Rather than travelling by private jets, we drive or fly coach to save money for payroll.

Here are a few lessons that I’ve taken away from my experience leading startups:

  • remain humble throughout
  • embrace uncertainty as normal, adversity as an opportunity, and failure as progress
  • develop a thick skin



Startup CEOs must remain humble throughout the rollercoaster ride, aka building a business. For starters, it can keep you sane in the face of the enormous pressures and demands on their time and mindspace. But perhaps more importantly, it is necessary as you build a learning organization that can evolve over time.

For example, many leaders are so focused on convincing and persuading their teams to follow a certain path that they miss the opportunity to learn from others. Instead, you must recognize the value of different points of view, and engage with those who stand on the other side an issue. By doing this you not only learn yourself but you also validate others perspectives.

Learn to share your mistakes as opportunities to teach and admit your own imperfections so that it is acceptable for others to be fallible. Research finds that employees who perceive altruistic or humble behavior from their leaders are more innovative.

Uncertainty = Normality

Uncertainty is simply par for the course for startup CEOs. Embrace it!

In the long-term, it is important that you develop discipline both individually and as an organization, so that in the face of uncertainty you remain aggressive and focused, and not frazzled and distracted. A friend of mine (who deals with Treps EVERY day) uses this Ulysses S. Grant quote at the end of all of his emails, “In every battle there comes a time when both sides consider themselves beaten. Those who continue to attack win.”

In those uncertain moments, it is also critical that you differentiate what is within your control what is beyond your control, and focus your efforts. You must also admit that you don’t have all the answers when you truly don’t, which will create opportunities for others on your team to step up and offer solutions.

Crave Adversity

Dealing with adversity is synonymous with the title of CEO. The easy problems with simple solutions don’t land on the CEO’s desk, and accountability for a CEO more often means taking fault for the losses than taking credit for the wins.

Rather than cowering from adversity, startup CEOs can use those situations to re-affirm the culture and mission of the organization. Remaining steadfast and committed, by example and in messaging, in the hardest times can bond a team and refine a culture.

Understanding Failure

Failing is simply part of the life of an entrepreneur. Being a startup CEO is similar to being a baseball player: even the best still fail 7 outs every 10 times. If you are not failing as an entrepreneur, you simply aren’t setting your goals high enough or deploying your resources to their full extent.

It is extremely important to see failure as a lesson learned. As clinically and dispassionately as possible, document your actions and reactions, assess and analyze the causes, and develop key-takeaways for the future . More times than not it is those that can follow this advice that never repeat the situation again. View failure as experimentation that leads to discovery and innovation.

 Have A Thick Skin

Startup CEOs must be thick skinned. You have chosen to take on the role of leader in a family of unrelated people, they are going to talk. Be prepared to hear whispers, deal with them and dismiss them graciously.

Whether it comes from the market, your employees, your spouse or the world at large, eventually others are going to question your intelligence, competency, leadership skills and just about everything under the sun. If this isn’t happen, guess what…no one really cares about your company. Never let the whispers of other detour your vision.

Eric Rice