Dear Wholegrain Wisdom Community,

You're pitching your idea for the 100th time and getting rejected again. Meanwhile, someone "less smart" with a corporate job is earning more money, working less, and sleeping better. You start thinking maybe you're not as intelligent as you believed. Sound familiar?

This was Francesco Cracolici's reality before becoming a successful venture partner. Today, he's invested in 30+ startups and manages funds across emerging markets. His transformation didn't come from working harder or finding better ideas. It came from understanding a fundamental psychological trap that destroys most entrepreneurs before they even begin.

Francesco reveals why starting a business for money creates a vicious cycle of failure, how your mind prefers "bad known" over unknown success, and the ancient wisdom that transformed his approach to confidence and entrepreneurship. His story offers a completely different framework for building sustainable success.

Key Highlights from Our Conversation:

The Money Trap That Destroys Smart Founders

Most entrepreneurs start with a simple belief: creating a company is the best way to get rich. Francesco fell into this exact trap. "I wanted to be successful and I wanted to be rich and the only way I could perceive I could have done it would have been by creating a company," he explains. But here's the brutal reality he discovered: if you want to make money, don't start a company. The people making the most money with the least effort? Those who join fast-growing companies and learn high-demand skills. Francesco now tells aspiring entrepreneurs: "Find a company growing like crazy, learn to code in AI, and you'll become super rich in five years without working more than eight hours a day."

The Vicious Cycle of Rejection and Self-Doubt

When you start a business for money rather than passion, you make a critical mistake: you build what you think is nice, not what people actually want. Francesco describes this perfectly: "You go and shove in the amount of food that they don't like and they spit it on you." After 100 rejections, you start comparing yourself to others who seem less capable but are earning more. The transformation is brutal: "Before you were a smart guy with a dream, now you're a stupid guy with a dream and it gets worse." This creates a negative feedback loop where each rejection reinforces your growing self-doubt.

Why Your Mind Prefers "Bad Known" Over Success

Francesco learned a game-changing concept from psychologist Alfred Adler: "Your mind has the goal to protect you from dying. To do so, he prefers a bad known than any unknown." This explains why entrepreneurs often sabotage themselves when approaching success. If you've always struggled with jealous partners, you'll unconsciously choose another jealous partner because the alternative is unknown territory. Your mind creates elaborate justifications (often called traumas) to maintain familiar patterns, even when they're destructive. Understanding this pattern is the first step to breaking free.

Ancient Wisdom Meets Modern Entrepreneurship

At his lowest point, Francesco discovered the Bhagavad Gita, an ancient text that changed everything. The core message: "Do whatever you feel is right, do it at the best of your abilities, completely forgetting the outcome." Francesco realized he was doing his best work but obsessing over outcomes while ignoring what he genuinely wanted to do. This shift led him to organize an event in Sicily that seemed impossible. People thought he was crazy for promising to bring 30 investors and 10 billion in capital to Palermo, but following his genuine passion created extraordinary results.

The Sicily Breakthrough: Saying No to $50 Million

Francesco's transformation culminated when he successfully executed his "impossible" Sicily event, leading to an offer to manage a $30-50 million fund in Singapore. The old Francesco would have taken it immediately for the status and LinkedIn likes. Instead, he said no because it didn't align with what he truly wanted: helping startups in emerging markets and supporting governments in Africa. This decision, which seemed illogical financially, opened doors to work he genuinely loved. "I finally understand what I really want and life is much better," he reflects.

The Confidence Revolution: Changing Your Glass

Francesco's most powerful insight involves how confidence actually works. Most people think confidence is like filling a glass with a percentage of belief. The reality is different: "You always have 100% but of different glasses." You might have 100% confidence in failure rather than 100% confidence in success. The key isn't building more confidence but changing which glass you're filling. When Francesco realized he had unlimited confidence in the wrong outcomes, he could redirect that same energy toward success. This isn't positive thinking; it's understanding how your psychological patterns actually function.

My Personal Reflections:

I met Francesco a few months back and we immediately became good friends. Somehow, we feel like we’ve known each other for years, even though we actually never met in person (in this lifetime) yet! I admire his charisma deeply and fully share his journey to learn about the “secrets of the mind”.

For this reason, we are actually working together on a new mastermind program for founders, fully dedicated to shifting mindset and rewiring it to align with your deepest and most craved goals. It’s a fully online program, and we are looking for 5 entrepreneurs willing to test our beta before it goes live in a few months. Are you interested? DM me back and I’ll share the form to apply 😉

Reply

or to participate