Rami Cassis has hired four CEOs. He replaced three of them. In this episode of CEOs Unscripted, the Monaco-based investor and founder of Parabellum Investments sits down with Jane Gentry to share the unfiltered truth about what separates great CEOs from expensive mistakes and why emotional intelligence matters more than any MBA or sector experience ever will.

If you hire CEOs, aspire to be one, or are already in the seat, this conversation will make you rethink everything.

Key Topics Covered:

• Why CEOs who come from sales are dangerously optimistic with forecasts
• The subtle client signals most CEOs completely miss until it’s too late
• The difference between managing UP vs. managing DOWN and why it destroys cultures
• Why “wartime CEOs” and “prosperity CEOs” are completely different animals
• What the first 60-90 days in a new CEO role should actually look like
• The single number every CEO must have an iron grip on
• Why being NICE is not the same as being KIND and why it matters enormously
• How a culture of fear silently kills your best performers

📌 Episode Timestamps:

• 00:00 — Cold open: Why hiring a great CEO is as hard as hiring a great salesperson
• 01:00 — Welcome to CEOs Unscripted
• 02:35 — Meet Rami Cassis, Parabellum Investments, Monaco
• 03:06 — Rami’s backstory: Egypt, France, Australia, oil & gas, and beyond
• 05:41 — What Parabellum Investments actually does
• 07:07 — What Rami looks for when hiring a CEO
• 08:08 — The three painful reasons his CEOs failed
• 08:44 — Mistake #1: Consistently missing forecasts and why sales CEOs are the worst offenders
• 10:44 — Mistake #2: Failing to read the room with clients
• 12:47 — Why EQ is rarely in the top 3 things we interview CEOs for
• 13:41 — Wartime CEOs vs. prosperity CEOs, which one are you?
• 17:18 — Why emotional intelligence is hard to measure but impossible to ignore
• 19:38 — The self-awareness paradox, the higher you climb the blinder you get
• 21:26 — Is EQ innate or learned? Jane and Rami debate
• 22:46 — Delivery matters as much as content, maybe more
• 23:54 — The difference between being NICE and being KIND as a CEO
• 25:31 — Mistake #3: Managing up but not down and the culture of fear it creates
• 27:41 — Signs you have a culture of fear (Jane’s tell-tale meeting test)
• 29:13 — Autonomy vs. accountability, where CEOs get the balance wrong
• 31:17 — When you trust too much, the costly CTO technology mistake
• 33:39 — Why major decisions need an outside voice with no dog in the fight
• 35:26 — What counsel would you give a brand new CEO?
• 36:35 — First 60-90 days, listen, observe, resist the urge to act fast
• 38:34 — It’s okay not to know and why admitting it builds more trust than hiding it
• 39:42 — The unprepared sales leader who won his team over with one apology
• 40:47 — Play to your strengths and outsource your weaknesses
• 41:40 — The numbers every CEO must know cold
• 42:33 — Why a 13-week cash flow forecast is non-negotiable
• 44:25 — How do founders know they’re in a turnaround situation?
• 44:33 — The financial warning signs of a business in trouble
• 46:41 — Cut marketing or double down? Jane and Rami respectfully disagree
• 47:22 — Why a strong CFO is every CEO’s most important co-pilot
• 48:42 — What Jane did differently during COVID and why it worked
• 49:24 — Asking for opinions doesn’t mean you have to take them
• 50:33 — Rami’s final thoughts and what he hopes others take from his mistakes
• 51:08 — Jane’s closing thoughts

🎙️ About CEOs Unscripted:

CEOs Unscripted is a bi-weekly podcast for mid-market CEOs, no fluff, no jargon, just real conversations from leaders who’ve been in the trenches.