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October 30, 2025

What I really saw in the dealmaking world

Dealmaking world

I worked with the top bankers, investors, and operators who live inside the deal process every day. From the outside it looks precise. Inside it's held together by instinct, long hours, and more coordination than anyone admits.

Every transaction runs through a maze of spreadsheets, slides, and diligence files that never fully align. The intelligence is there. The effort is there. What's missing is connection.

Behind every deal are two kinds of work. The teams that build the numbers and keep the machine running. And the senior leaders who use judgment, relationships, and narrative to move the deal forward. Both matter deeply, yet they rarely move together.

The real cost of translation

Most teams already know what drives value. They can see the levers and the story behind the numbers. What takes the most time isn't the analysis itself, but the hand-offs.

Models are rebuilt after small changes. Slides are rewritten to match tone. Numbers shift across versions and everyone scrambles to sync. The real cost is translation.

Everyone feels it, but no one owns it. The process keeps moving, while clarity slips away with each revision.

When judgment doesn't travel

The best dealmakers rely on experience. They know which details matter and how to read a room. That judgment drives outcomes, yet it rarely travels cleanly through a team.

A few insights shared on a late call can take days to appear in materials, and by then the moment has passed. Firms that scale well find ways to make that experience visible. They don't just talk about intuition—they embed it in how the work gets done. When experience becomes shareable, everything compounds.

Other corners of finance have evolved

Trading moved from phones to code. Data science left spreadsheets for live pipelines. Even the back office runs faster and more connected than ever.

Dealmaking hasn't caught up. It remains the most judgment-driven, collaborative corner of finance, but it still runs on disconnected tools and manual effort. The issue isn't resistance to technology. It's that nothing has yet respected the human side of the process.

Good judgment can't be automated, but it can be sharpened. When analysis and story align with how senior teams actually think, insight appears faster. The right questions surface early. The story of a company becomes clear in hours instead of weeks.

When that happens, decisions feel different. People move with confidence instead of caution.

What I take forward

After seeing this world up close, I stopped assuming the friction was inevitable. The challenge isn't talent or ambition. It's that the system around great people never evolved to match the pace of their work.

The next step in dealmaking will come from connecting information, analysis, and story into one motion. When those pieces align, judgment gets sharper and teams move faster.

That's the future I want to help build. A world where dealmaking feels focused. Where insight flows easily. Where great people spend their time making decisions instead of chasing versions.

DG

Drake Goodman

CEO, Co-Founder