top of page

Parashat Vayishlach

I saw an angel face to face, and my soul was saved

There comes a moment in the life of every entrepreneur when he must make a crucial decision - do I despair or do I rise to meet the challenge and fight to overcome it. It is a fateful moment not just for the company - for that is the moment that determines whether the startup would triumph or go under, but also for the entrepreneur himself - would he continue his journey of growth as a human being or stay in his comfort zone without ever facing the challenges of his life.

It is in such a moment that Jacob finds himself in parashat Vayishlach. After a lifetime of being the youngest child, a dweller in tents that brews schemes and tails behind the heels of others, Jacob finally arrives, now an older man, to the moment of truth where he will meet his brother Esau face to face. On the night before their rendezvous, Jacob finds himself all alone when out of nowhere an unidentified man appears and begins to wrestle with him:

And Jacob was left alone, and a man wrestled with him until the break of dawn.

This is the pinnacle moment in Jacbo’s life, the moment where he must make the decision to fight or to surrender. Will he forever remain the dweller in tents that hides behind his mother’s apron or will he meet the angel face to face and fight for his rightful place as the heir of Abraham and Isaac.

The choice is in his hands. Just as the choice is in the hands of every entrepreneur who has tumbled down the depths of despair, whether because of a failed funding round, financial dire, lagging product sales, or any other challenge that necessarily presents itself throughout the life of a startup.

Jacob decides to fight. He meets the angel, that is to say he meets himself, and thus complete his journey from a dweller in tents, a wannabe who knows only to follow - as his name suggests (from Hebrew יַעֲקֹב, to follow), who runs from conflicts and shies away from challenges, into one of the three forefathers worthy of the title “Israel”. As the bible says:

And he said, ״Your name shall no longer be called Jacob, but Israel, because you have commanding power with [an angel of] God and with men, and you have prevailed.״ [...] for I saw an angel face to face, and my soul was saved.

As an investor, I consider these moments nothing short of a miracle, and there is nothing more gratifying than seeing an entrepreneur I invested in go through the same process.

I greatly enjoyed, for example, seeing Ariel Assaraf, who at first adamantly refused to take on the role of CEO of Coralogix, grow and progress until becoming the undisputed leader of the company, which today is on track to being the next unicorn in the world of data analytics.

Same goes for Gabriel Jacobson. Before being appointed the CEO of Valerann, Gabi was for many years an attorney at S. Horowitz & Co, one of Israel’s premier law firms. Since then, he has been tirelessly working on improving himself and is changing from a first-time CEO into a confident and powerful leader right before our eyes, one who has led the company through a successful pivot and positioned it as a game changer in the world of road infrastructure.

And if there is one entrepreneur who can honestly say she has been to the valley of despair, met with existential anxiety and come out the other side, much like Jabob before his meeting with Esau, it is Adi Wallach, founder of CalmiGo. After dealing with anxiety attacks and inefficient conventional treatments all her life, Adi has come up with a life-changing, non-medication treatment for anxiety, thus turning her lifelong struggle into her life’s purpose. And only recently she has been through a war for survival to complete a funding round under catastrophic market conditions, from which she has come out triumphant thanks to her decision to stick with it and fight to fulfil her purpose.

Rising from Beira Amikta to Igra Rama, as Chazal say, from the deepest cistern to the highest roof, is a journey that necessarily goes through hardship. There is no escaping our meeting with ourselves, with the challenges that life presents us with. As long as we attempt to run away from them, our lives will be as hard as Jacob’s. But the more we manage to meet them bravely, having full faith in our purpose, so can we find within ourselves the strength of God, as did Jacob, for he is Israel. What Jacob, Ariel, Gabi, and Adi all have in common is the choice they made at a relatively older age to come out of their tents and fight the angel, meet themselves, and so overcome, mature and connect with their purpose in a clearer and more conscious way.

Building a startup is a process and a spiritual journey during which we, as entrepreneurs, decide to meet ourselves. As an investor, I am not looking for the perfect entrepreneur because such a thing does not exist. I am looking for an entrepreneur who I believe possesses the integrity and honesty needed to grow, who is not afraid to look fear in the eyes and do whatever is necessary to carry themselves and their startup to the next stage in their lives.

As the years go by, I continue to hone - so I hope - my skill of identifying such entrepreneurs. But I can never know for sure. Personal growth is something that takes place exclusively within ourselves. Leadership is the state of being alone. Not the investor, nor the Chairman, not even the entrepreneur’s mother - though she may be as strong as Rebecca - can make the choice for him, the leader. He alone can make that choice. May it be so that we all find the strength to always choose to mature further and grow without fear or hesitance. For that choice would put us face to face with the divine within us, grant us meaning, and make our lives worth living.

Shabbat shalom

Drawing: The Meet, Shai Azoulay

3 views0 comments

Recent Posts

See All


bottom of page