Pivoting Your Own Life - From An Investor To An Entrepreneur, Paving Your Own Path

Ohad Shaked,
Co-Founder & CEO at ThinkUp, Co-Founder at Thinkz

Ohad is the third generation to a family of entrepreneurs. His father was originally a dentist, and in mid-life his brother pulled him into the Tech world, and from there they founded 888, a success that changed the face of the entire family. At first Ohad joined as a bystander, absorbing everything that was going on, the atmosphere, the business conversations, learning this unique world, but what started as a slow process changed completely when his father passed away and all the cards were shuffled. Ohad thought he could get a grace period, but reality had a different plan, and within a day all the responsibility of the family business fell on his shoulders.

The delicate fabric of a family business

"As long as it was my dad running the business these were his problems - every morning with my uncle was different - on Sunday they were fighting, on Monday they drank coffee, Tuesday they fought, Wednesday drank coffee again. There are always matters with partners, but when the flow is strong and everyone’s proud - then

"It's less difficult. After he died, things changed, relationships changed, needs changed."

The roller coaster continued, but this time around Ohad. At 30, he was given a crazy responsibility in many aspects - legal, business, financial, lots of balls to juggle in the air, but Ohad was still enveloped in the same innocence of a young guy who thinks he knows everything -

"I saw my dad sitting in the living room sometimes and watching all sorts of silly comedies, and I thought to myself - if he succeeded, I can too, it's not a problem, it's not difficult. You don’t understand the size of the responsibility and the size of the complexity. Part of the reason I joined is because I saw he was getting a little tired. I don’t know where I got my impudence, but I told people - give it a year or two and I'm stepping in to take his place. I was rude and stupid."

Shortly before his father died, he made his second investment of 50 million NIS before the age of 30, and he shares that he did it as if he were ordering coffee at a restaurant, it didn’t mean much to him.

"Then over the years you realize how much you don’t understand. How difficult things are, how complex they are - you make plans and life plans differently."

He took over 12-13 companies - all with problems of being or ceasing to exist, and the stock that fell by 70%, with no experience and knowledge of how to rehabilitate everything, but with an inner fire knowing he couldn’t let it fall on his watch.

He also notes that he understands that such things are "troubles of the rich", and that he could also sit on the sidelines and still have something to eat, but it was his personality that pushed him in and brought a lot of stress into his life as well. He has the rational side that knows what is right and does things in a calculated and logical way even though it’s scary, but on the other hand - the body responds. Abdominal pain, lack of sleep, everything floats to the surface and is reflected in some way in the body. At first he didn’t understand the connection between the two, how you can understand something rational and yet the body speaks the price of the emotions - he had to experience it in his flesh to internalize how intertwined they are.

Selling the giant company

After his father died, the stock was down, but Ohad didn’t want to just sell it and run away - although from the age of 18 he knew that this was his ultimate goal, and that it was not the place that matched his DNA, he first wanted to reach the company's potential. They waited a little longer, and were helped by the late Shay Ben-Yitzhak, their partner, and in the end sold the holdings.

Ohad recounts the relief he felt then, when he realized that for eight years he had put his life on hold and concentrated entirely on rescuing and selling the company. He had no room for anything else, and suddenly he had time for himself, to figure out what he wants to be and what imprint he really wants to leave. He can breathe again.

I asked Ohad what he thinks on the Ohad of more than a decade ago, and the place from which he operated, and he shares that in retrospect, there are many nodes in his career that he would like to change, that there’s regret around them, but in the same breath, he knows he also grew out of suffering. There was something very deceptive in his path - in an instant and without preparation he jumped from the bottom of the pyramid straight to the top of the top, to the board and above it as a shareholder, and this shortcut was not necessarily healthy.

Many times we all dream of shortcuts to be at the end of the pyramid - to sit at the top of our dreams, comfortably, with the impact and power to do and create what we want, but we must not forget how important the way itself is. It inevitably embodies the lessons, experience, hardening and resilience we need in order to stand on top and look at the landscape. Whoever we become while climbing is the person whose place is at the top.

And Ohad felt it in his bones, that same need, to go back and rebuild himself on his own  as an entrepreneur. Ohad recounts how a year ago when he was sitting with his partners in Kiryat Ono, he told them:

"Here with you in this situation, I feel stronger than I felt ten or fifteen years ago as an investor, the foundations are more stable, it feels more right."

There’s a misconception when looking at Ohad from the outside, that things seem simple for him - but on each side there’s complexity and struggle. Our self-worth depends greatly on and connects to our doing, there’s no way to escape it, and the experience of failure, even against the background of past success, is difficult and challenging to digest. Ohad shares that this connection exists within successful people as well. Even great success brings with it a mental price, the size of the responsibility intensifies and there’s anxiety to maintain the same pick from the understanding that from here it can only deteriorate.

No matter where we are, our sense of self-worth is something that needs to be constantly maintained - because the high-tech world brings with it a great many upheavals, and if we don’t have this stable foundation, we are lost.

It took Ohad a long time to bring calm back into his life and internalize it.

Turning from an investor to an entrepreneur

As someone who has the unique perspective of both parties - as an entrepreneur and as an investor, Ohad has learned which entrepreneur he wants to be. A common mistake he talks about is centralism in entrepreneurs - everything has to go through them, and there’s a lack of awareness of when they are suitable and when it’s better for them to move aside even though it hurts. This conduct is a recipe for many clashes between entrepreneurs and investors, with each thinking that the other doesn’t understand. Today he does the opposite of what he saw - he makes sure to delegate authority and responsibility, be transparent, make sure all the information passes between everyone, and know when to take a step back.

After the sale of 888, Ohad sat down for coffee with Prof. David Passig, whom he greatly appreciated, and in an unplanned spark told him - "Let's do something together." David was silent for a moment, leaned back and then said - "Let's do something big". During the creation process of his first startup, Thinkz, and abrasive iterations, Ohad thought - why is there no digital platform that helps startups build themselves? The machine of the machine. This thought was the birth of the second startup ThinkUp.

There are two known and clear facts about the world of startups - one, it’s difficult to build a startup - entrepreneurs need mentoring, guidance, co-founders, validation, customers, and everything together is very complex. The second thing is, everyone is trying to help startups. Still, there is an unmet need here - there are very few digital platforms that give value and know how to connect all the dots. Ohad wanted to make it easier for entrepreneurs, allow them to run the startup and receive guidance and help on one platform. The passion for the idea motivated him, and today he is a full-time parent of ThinkUp. Together with the amazing founding team at ThinkUp, Ron, Hila and Moti, they are building an innovative platform that is destined to be the place where every entrepreneur begins his startup journey, while significantly streamlining his exact schedules and connections for product development, connection to investment and company growth.

Despite his caution embedded in his personality, when I asked Ohad if he enjoys this current time, he replies -

"I enjoy every time we have a breakthrough, solve something, it's fun. When I tell the story of our startups, my eyes spark."

And as someone who sat in front of him for a fascinating conversation and heard the story of his entrepreneurship journey, I can testify firsthand that you can definitely see the spark.

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