Episode #5: Both Sides of the Table: From Entrepreneur to Investor

Show notes

What does an entrepreneur see that a career investor might miss? And what changes when that entrepreneur crosses the table to become the one writing the cheques?
In this episode, I welcome Shanu Sherwani — a private equity professional with a rather distinctive trajectory. He started as an entrepreneur, moved into fund management, and now serves as Chief Investment Officer of a single family office. That dual perspective — operator and capital allocator — shapes everything: how he assesses opportunities, how he reads people, and how he thinks about risk.
We cover considerable ground:
— The shift from founder to funder: what surprised him, and what stayed exactly the same
— Decisions driven by instinct rather than consensus — and when the numbers alone simply are not enough
— The gap between PE theory and the rather messier reality of deploying capital
— What people consistently get wrong about risk (not the textbook version — the lived one)
And in the spirit of genuine conversation, Shanu turns the questions on me. We discuss managing across multiple disciplines, the European perspective on private equity, and a few things I wish I had known rather earlier.
Whether you are curious about private equity, considering a career shift from operations to investing, or simply enjoy an honest exchange between two professionals who have been on both sides of the deal — this one is for you.
This is Ask Carlo™ | Private Equity, Simplified.
Real deals. Real strategies. Real billions. No jargon, just compelling stories from 30 years inside European private markets.
 
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NEXT EPISODE: next week – growth equity. How DST Global invested €234 million in Revolut at a €2 billion valuation in 2018 and watched it grow to €29 billion. The strategy, the scaling, the returns.
But first, next week: our first Ask Carlo Interview. A family office executive, former fund manager, and entrepreneur shares their personal story in and around private equity.
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ABOUT ASK CARLO™: I have spent 30+ years co-managing billions across European private markets – buyouts, venture capital, growth equity, real estate, infrastructure. Every Tuesday, I share one real deal to help you understand how sophisticated capital actually works.
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DISCLAIMER: This content is for educational and informational purposes only. It does not constitute investment advice, financial advice, or any other type of professional advice. Always consult qualified professionals before making investment decisions. Educational only. Not investment advice.
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