What the Entrepreneurial Roller Coaster Feels Like; a Conversation on Success, Anxiety, Self-Worth, Trade-offs, Luck, & Writing

Shaul Olmert,
Co-founder & CEO of Piggy, Co-founder & former CEO of Playbuzz, Author

Shaul is an experienced co-founder & CEO of several startups. In an honest and vulnerable way, he shares with us how the entrepreneurial roller coaster accompanied him throughout the last decade, in ways such as being preoccupied with the question "What is success?" And how he measures it.

Many entrepreneurs start on the entrepreneurial path excited and out of wanting to change the world. For Shaul, it started from a depressed and doubt-ridden place. When he founded Playbuzz at the age of 36, he was caught up in the rat race after tasting big-time success for the first time. He thought about how one can become rich & famous and get on the cover of the Wall St. Journal.

When he got the idea that would later become Playbuzz (which he officially founded at 36), he finally wanted to succeed out of a belief in the idea & not the sanctification of the very success itself. Shaul's 10 Years at Playbuzz were a crazy roller coaster, with many ups & downs, but mostly, a lack of control. When there is a lack of control - anxiety arises. One of the main problems is when entrepreneurs confuse the startup with themselves. They feel like they are one. Then, when the two can't be separated - there is confusion between our self-worth and the result of our actions, which exerts an immense pressure that sits on your shoulders, which is destructive to hold for long. Simon Biles, the Olympic gymnast, recently withdrew from many events at the Tokyo 2020/2021 Olympics because she felt her mental health wouldn't allow her to perform safely. She knew how to stop in time not to hurt herself - that is, she created this separation between who she is as an individual and her professional role.

Dealing with anxiety:

  1. Empathy - a supportive environment that will strengthen and lighten the burden. Talk openly about what is happening, share and reflect what you feel. Don't try to be superheroes. Shaul describes how he thought he had to keep everything contained, not show the cracks, and now he knows he paid a heavy price for it. He brought negative energy into situations, which hurt many people along the way. Over time, he learned to surround himself with authentic people who want his best and the best for him, not only those who would stroke his ego.
  2. Shaul describes a difficult moment when the rug was pulled out from underneath the company since regulatory changes caused its revenues to be cut 30% overnight. They had to put everything on hold and stop the bleeding, which led to firing 50 people (primarily recent hires). This caused Shaul severe anxiety.
  3. One of the most effective tools for dealing with anxiety is breaking it down into factors. Instead of feeling like we are dealing with a million things and it closes in on us, ask yourself, "what am I afraid of," and make a list. The list of factors sets them out clearly, which may alleviate stress and help formulate solutions. 

An entrepreneur's desperation for success is rarely more evident than at the beginning of their journey. They adopt narratives for themselves and determine their self-love based on external achievements. But success - it's dizzying and isn't freeing. With success comes a whole new and completely new stage - one that's even more stressful.

Many times they try to analyze how their startup succeeded. There are many factors that one can try to pinpoint and measure in a company's growth - but there are quite a few things that are not easy to put the finger on, and they fall under an umbrella called "luck." It is tough to predict what will lead a company to meteoric success and what will be a cause for its demise. This highlights how many elements in the entrepreneurial journey are beyond our control (it's more than the idea, technology, staff, good investors, customers, etc.).

After 2 years, Playbuzz suddenly became successful overnight. On February 27, 2014, they had 1,000 users, but they had more than a million the next day. A user from England created content that went viral. With success, expectations grow. Until then, they had nothing to lose, but suddenly - they were afraid of losing everything. Concerns of how to maintain this success began. It is important to enjoy success, but one should stay with their feet planted on the ground. Shaul did not act like that. In his own words, he describes the 'magnification craze' he felt - wanting more millions, competing with friends, and being in more headlines. He admits he felt haunted by this sensation; it ruled him for many years.

How does one balance?

Shaul shares how, for 5-years, he lived far from his family, on the New York-London-Israel line. Today he knows he should have chosen a much more balanced route. He grew up with a workaholic father, one who had limited time. Instead of changing the pattern - he did the same thing. Today he knows to say that he was so haunted by the need to succeed big-time - that he acted out of impulses and sometimes lost his way. For Shaul - the writing was liberating. He took a step back, left Playbuzz, and started writing. He has been writing for several years and recently published a book; "The Sellers of Dreams." Although it isn't autobiographical, there is a remarkable resemblance to his experiences.

Shaul also began psychological treatment; it took him a long time to make room for it emotionally and physically and to be able to ask for help. It put him through a fantastic process that gave him a lot of power and perspective. Shaul emphasizes how important it is for entrepreneurs to receive this mental support from the beginning since the pressure is significant. He thinks any venture capital fund should have a professional who knows how to support entrepreneurs mentally. Today he is leading his next venture - and this time trying to do so in a much more balanced and conscious way.

Contact Me

Thank you! Your submission has been received!

Oops! Something went wrong while submitting the form.