John is joined by Maurice Harbison, Partner at Carlsquare, who brings 25 years of experience in global tech M&A and more than $40 billion in transactions.
In this episode, he takes us inside the deals that taught him the biggest lessons. From a German software business that drew 20+ offers despite a 60% client concentration, to a billion-dollar opportunity that collapsed at the signing table due to a last-minute demand.
He also reveals why so many cross-border deals break down, and what he makes of the AI-driven “SaaS apocalypse.”
Listen to Maurice’s take on:
- How boutique advisory differs from a global bank
- Why culture decides more deals than valuation
- How AI is changing what software companies are worth
- What sets a great leader apart from a great banker
- Why it’s not the mistake that matters, but when you make it