1. What have you found most challenging as a CEO or executive of a large enterprise?

The most challenging part in any organization, large or small, is to find and coordinate a group of talented people towards a common goal. I have made all the mistakes in the book when it comes to working with others and will always consider myself a lifelong student in the art of inspiring and coordinating people.

2. How did you become a CEO or executive of a large enterprise? Can you please briefly tell the story?

I became a CEO through the entrepreneurship route. After a few failed ventures I realized the importance of a centralized point of power in an organization and started increasingly taking responsibility for processes all across the organization, along with influencing the structuring of the companies, which naturally led me to the CEO role.

3. How do you structure your work days from waking up to going to sleep?

I generally start each day with meditation, a headstand, and breakfast, after which I assess the tasks and goals to be done that day. Generally, I like to spend as much time as possible on the front lines, doing things that have a material output, and less time on activities like having meetings, strategizing, and researching. This is because while strategy and big picture work do play a huge part in building a great organization, it does not move the needle from day to day, and is almost always better constructed on the fly, collaboratively throughout the organization, with live input from the day-to-day operations. Beyond that, I believe that the best CEOs motivate their teams by doing the hard work required alongside them, and not by standing behind them, trying to steer work that they don't fully understand themselves.
When it comes to actually structuring day-to-day work, I like to distinguish between divergent and convergent tasks and adapt the working style of me and my team according to that. When it comes to doing divergent tasks, such as designing a new interface or a new marketing campaign, it is important to realize that it will be harder to micromanage such progress, as it is more non-linear, and depends on finding the right inspiration, which is why these tasks generally require a much more open and inclusive approach where all ideas are welcomed, explored and extrapolated. When it comes to doing convergent tasks, such as developing new functions or doing accounting, it works better to have a more rigid schedule, splitting up larger projects into smaller tasks and working linearly to get things done, dismissing any ideas that don't help the project get done quicker. Whatever goals I've set for myself on a certain day, I will not go to bed before those are done. While this at times has forced me to stay up for far too long and sacrifice hours of sleep, it also helps me feel a purpose every day and satisfaction from contributing to the team and developing the ability to formulate reasonable goals for myself and my team over time.

4. What's the most recent significant leadership lesson you've learned?

The most important strategy that I've learned to increase my efficiency in this area is to develop skills to do tasks myself across the whole organization, including technology, legal, operations, sales and marketing. Once I stopped thinking that I had to find someone who could do what I couldn't do and started looking for someone who was better than me at doing something I could do, it was much easier to vet and hire high-quality team members, as well as gain their respect and empathize with and influence their work.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

How to win friends and influence people by Dale Carnegie. This book is a very powerful reminder for me of the power of kindness and the importance of leading with a carrot and not with a stick.

6. How do you build leadership capacity in a large enterprise?

By taking personal responsibility and initiative for the whole organization, and working diligently to see that responsibility and initiative materialize as value for the broader organization.

7. What is one meaningful story that comes to mind from your time as a CEO or executive of a large enterprise so far?

The most meaningful experiences I've had as a CEO so far relate to betrayal by people I believed to have my and the organization's best interests at heart. Without going into details I've unraveled several situations where people were trying to freeride on the organization and take more than they were contributing, and it is a very valuable lesson in re-evaluating how you judge and include others and an important reminder of the power of hiring slow and firing quick. It is so important to strike the right balance between trust and cynicism - being too trusting and naive can easily destroy a company, simply because most people are not able to see beyond their own needs and desires, but being too cynical can be equally damaging as it tends to create one-person teams.