In every generation, four entrepreneurs sit across from me.
Not in one order. Not in the same meeting. But over the years, I learned to identify them within a few minutes. Even before they open the presentation, even before they explain to me about the “deal of a lifetime” - I know who is sitting across from me.
The Haggadah (the text read at the Passover Seder) knew them thousands of years ago. It called them the wise one, the wicked one, the simple one, and the one who does not know how to ask. I call them by other names.
The wise one - the one who arrives too prepared
Yoni walked into the office with a 47-page spreadsheet.
Market analysis. Rental forecasts by quarter. A comparative analysis of six neighborhoods in Detroit. Leveraged financing in three stages. An exit strategy. A backup strategy for the exit. And a backup strategy for the backup strategy.
He asked me excellent questions. About the structure of the LLC, about legal protection between properties, about the tax implications for Israeli citizens holding real estate in the US. About the protocol in case of a dispute with a tenant.
At the end of the meeting I said to him: “Yoni, everything is perfect. When do you close on the property?”
He looked at me: “I still need to finish the research on Florida. Maybe Texas too.”
That was three years ago. Yoni is still researching.
The wise one hides behind his knowledge. He believes that one more data point, one more analysis, one more conversation with one more expert - will guarantee he doesn't err. But in real estate, as in life, there is no risk-free decision. There is only an informed decision made on time.
What do I say to the wise one? Put the learning (Torah) you've acquired to work. The knowledge you accumulated wasn't meant to keep you on the fence, it was meant to get you off it.
The wicked one - the one who thinks he doesn't need anyone
Mark didn't really ask for advice. He came to confirm what he had already decided.
An experienced developer. A few successful deals in Israel. Self-confidence that fills a room. He explained to me with great patience, as if I were the one who had learned from him and not the other way around, that he “already understands this,” that the legal structure is “just bureaucracy,” and that lawyers “only complicate things that are simple.”
He bought real estate in Florida. Directly in his own name. No LLC. No protection. Without understanding the local tax laws.
Two years later he came to me with a problem. A tenant sued him. A personal suit. Because there was no legal entity separating the property from Mark the man.
He paid far more than it would have cost him to do it right in the first place.
The wicked one is not evil. He only cut himself off from the system. “What is this service to you?” - he disconnects himself from the collective experience, from the lessons of others, from the structures built precisely to protect him. And the foreign market does not forgive ignorance with a confident smile.
What do you say to the wicked one? You blunt his teeth - not to punish, but to let him face the consequences of his choices. And then, when he is ready to hear, you explain to him that real strength is knowing when to ask for help.
The simple one - the one who knows he doesn't know, and is willing to learn
Ronit came with one simple question: “How do you do this?”
Not a spreadsheet. Not false confidence. Just open eyes and a real desire to understand. An accountant by profession. Heard from a friend about an investment in Chicago. Came to me before taking any step.
We worked together for two months. I explained legal structures to her. She asked questions. She learned. Together we examined three properties before we found the right one. She didn't try to prove anything. Only to build something right.
Today, four years later, she holds two properties, with a stable yield and a property manager who works like clockwork.
For the simple one, the Haggadah says - open for him. Detail the road for him. Because he is not lacking ability - he is lacking a map. And whoever is willing to take a map and walk with it will go further than all the wise ones still standing at the intersection calculating.
The one who does not know how to ask - the one who is afraid of the question itself
Gili I have known for years. A friend of a friend. A smart man, owner of a successful business, free money waiting to do something.
Every time I meet him he says: “We have to sit down.” And we never sit down.
He is not afraid of failure. He is afraid of the question. Because to ask is to admit there is a possibility. And a possibility requires a decision. And a decision creates a new reality from which you cannot go back.
To the one who does not know how to ask, the Haggadah says: you open for him. You don't wait for him to ask. You open a gate for him.
To Gili I say every time we meet: “Shall we set something for next week?” He laughs. I don't give up.
The four sons sit across from me every year.
Sometimes in the same person, in different meetings, at different stages of life. I too was each of them in my turn.
The Haggadah ends, the Seder ends, but the question remains:
Which son are you this year?
Happy Passover. May it be a festival of opening gates - each of the gates you closed upon yourself.
Stories are based on real situations, with identifying details changed. Not legal advice.
Translated from the Hebrew original. עברית