Scott Gelbard's Blogger

Early in my career, I watched a deal fall apart that had no business falling apart. The numbers worked. The strategic rationale was sound. Both parties genuinely wanted to reach an agreement. The legal teams had done their work. And yet, in a single meeting — a dinner, of all things — something broke. Not the terms. Not the economics. Something subtler and more permanent: trust. One party walked away feeling disrespected. The other was baffled about why. Neither could fully articulate what had happened. The deal died not because of strategy or finance, but because two highly capable groups of people were operating on different cultural operating systems — and nobody in the room was fluent in both. I've thought about that dinner many times over 25 years of cross-border work across North America, Europe, and Asia. It's the moment that convinced me that the most underrated skill in international business is not language. It's not technical expertise. It's cultural trans...

There is a moment in nearly every engagement I take on when I sit across from a founder or owner-operator and ask a simple question: "What would have to be true for your business model to stop working?" The pause that follows tells me everything. Not because they don't have an answer — most experienced operators have at least a partial one. The pause reveals something more important: how recently they've actually thought about it. In more cases than I'd like to admit, the honest answer is that the question hasn't been asked seriously in years. The business has been running. Revenue has been growing. The model that worked in 2018 or 2021 is still the model today. And that assumption — that what worked before will continue to work — is precisely where the vulnerability lives. After 25 years of advising businesses across North America, Europe, and Asia, I've come to believe that deliberate, periodic stress-testing of your own business model is one of the h...

Early in my career, I was preparing for a significant negotiation on behalf of a client — a cross-border acquisition that would be transformative for his business if structured correctly. We had done all the standard preparation. Financial models, valuation ranges, deal structure scenarios, walk-away thresholds. I thought we were ready. We were not. What I did not know — and what became apparent within the first twenty minutes of the opening session — was that the lead negotiator on the other side had recently come under pressure from his own board to close a deal quickly. He was not negotiating from strength. He was negotiating from urgency. Had I known that beforehand, everything about our approach would have been different. That experience taught me a lesson I have never forgotten: the most important preparation you can do before any significant business engagement is not about your own position. It is about understanding the person across the table. I call this counterparty int...

I have sat across from some of the most capable business builders I have ever met and watched them make decisions that did not make sense on paper. They turned down capital they needed. They micromanaged teams that did not need managing. They stalled strategic moves that should have been obvious. And when I probed carefully — the way a long-term advisor learns to probe — I often found the same thing underneath. The business had outgrown them. Not in capability. Not in intelligence. In identity. There is a version of the scaling challenge that gets talked about constantly in business circles — the operational version. You have to build processes, hire leaders, put systems in place, stop being the one who does everything. That conversation is real and important. But there is another version that almost nobody discusses, and in my experience, it is the more dangerous one: the moment when a founder's sense of self becomes an obstacle to the growth of the company they built. The Iden...

I’ve sat on both sides of cross-border capital conversations more times than I can count. I’ve helped business owners prepare for them. I’ve advised investors evaluating deals across jurisdictions. And I’ve watched otherwise strong deals collapse — not because the numbers were wrong, not because the business wasn’t sound — but because the business owner walked into an international capital context with a domestic playbook. Cross-border capital raising is a different discipline. It has its own logic, its own relationship protocols, its own timeline expectations, and its own set of unspoken rules about what makes a business owner credible in a room full of foreign institutional investors or private capital providers. Treating it like a domestic raise with a longer flight is one of the most expensive mistakes a business owner can make. This piece is for the founder or business owner preparing to raise capital internationally — whether you’re seeking strategic equity from a European fami...