James Deller explains why he evaluates a founding team’s culture, decision-making, and treatment of people long before he looks at a single number — and why the order matters more than most investors admit.
Every founder assumes the first meeting with an investor is about the model — the revenue projections, the unit economics, the total addressable market slide. James Deller lets founders lead with that if they want to, but he’s rarely paying close attention to it yet. By the time he opens the financials, he’s usually already formed most of his view.
“Numbers tell you what already happened,” James Deller says. “I want to know what’s about to happen — and the financials are the last place you’ll find that.”
The Financials Are a Trailing Indicator, Not a Preview
Numbers are useful, but they’re backward-looking by definition — a snapshot of decisions made months ago under conditions that may no longer apply. What James Deller actually wants to understand before he gets there is what’s producing those numbers, and whether it will keep producing good ones under different conditions.
That means looking at the organization, not the output of the organization. This isn’t a philosophical preference for him — it’s a practical one, shaped by building and advising companies where the spreadsheet looked fine right up until the moment it didn’t, because the underlying culture had already started to erode.
“The spreadsheet is always the last thing to know something has gone wrong.”
How the Team Talks About Its Own Failures
One of the fastest signals James Deller looks for is how a founding team discusses their own past mistakes. Teams that minimize, deflect, or blame external factors for failures tend to repeat them. Teams that can describe a specific failure with precision — what went wrong, what they misjudged, what they changed afterward — are demonstrating the exact muscle that scaling requires.
Growth manufactures new failure modes constantly. James Deller wants evidence a team has a functioning process for learning from them, not just a good story about the one time they didn’t fail.
“A good story about the one time you didn’t fail tells me nothing about the ten times you will.”
Whether Decisions Are Actually Traceable
James Deller asks founders how a recent significant decision really got made — not the polished version, the real one. Was there data behind it? Did anyone disagree, and how was that handled? Companies with an emerging data-driven decision culture can usually walk him through this cleanly.
Companies without one tend to give him a story about instinct and momentum — which might have been right this time, but tells him nothing about whether it’ll be right the tenth time, when the stakes are higher and the instinct is under far more pressure.
“Instinct might be right once. Discipline is what makes it right ten times in a row.”
How the Team Treats People Several Levels Down
James Deller pays close attention to how founders talk about the people who report to them — not their peers or their investors, but the employees several levels down who rarely get mentioned in a pitch. Do the founders know specific things about how those people are developing? Or is the org chart a black box below the leadership team?
Organizations that develop their people, rather than simply extracting output from them, are the ones he’s watched compound advantage over years rather than quarters. That’s not a soft metric to him — it’s a leading indicator he weighs as heavily as anything on a balance sheet.
“How you treat the people three levels down tells me more than how you pitch the people at eye level.”
Whether the Team Can Actually Take Being Wrong
James Deller has learned to watch closely for how a founder responds when he pushes back on something they clearly believe. Defensiveness is a bad sign — not because disagreement is comfortable, but because a founder who can’t tolerate being challenged internally will build a team that stops challenging them, and that team will eventually miss something important because nobody felt safe raising it.
The founders he trusts most are the ones who get visibly more engaged, not more defensive, when someone credible disagrees with them.
“A founder who can’t handle being challenged in the room ends up with a team too scared to challenge anything.”
Where the Financials Finally Earn Their Place
Once James Deller has a real read on the team, the culture, and the decision-making discipline, the financials become a confirmation exercise rather than a discovery exercise. Good numbers from a team with weak culture make him more cautious, not more confident — usually it means the numbers are being achieved in a way that won’t hold up under stress.
Modest numbers from a team with strong culture and real discipline often interest him more, because he’s underwriting a trajectory, not a snapshot.
“Good numbers from a weak team don’t reassure me. They just tell me the stress hasn’t arrived yet.”
The Order Matters More Than Most Investors Admit
None of this means financials don’t matter — they absolutely do, eventually, and no amount of strong culture excuses a business model that fundamentally doesn’t work. But the sequence in which you evaluate a company shapes what you actually see.
James Deller’s closing point is simple: look at the numbers first, and you’ll be reacting to the past. Look at the people and the culture first, and you get a much better read on what the numbers are likely to look like next year — which is the only year that actually matters to an investor writing a check today.
“Look at the numbers first and you’re reacting to the past. Look at the people first and you’re pricing the future.”
