November 2025
What Operators See That Investors Miss
The gap between pitch deck and production reality.
Most investors evaluate infrastructure companies through pitch decks, financial models, and reference calls. They spend 20-40 hours on due diligence, then write a check.
Operators see different things. We look at the code. We model the unit economics. We understand what breaks at scale. We know the difference between a system that works in a demo and one that works in production.
The gap between what investors see and what operators see is where most infrastructure investments fail.
The Architecture Blind Spot
Investors ask: "What's your tech stack?"
Operators ask: "Show me your architecture diagram."
The difference matters. A tech stack is a list of technologies. An architecture is how those technologies work together under load, under failure, under scale.
I've seen pitch decks that list impressive technologies - Kubernetes, PostgreSQL, Redis, Kafka - but the architecture is fundamentally broken. Single points of failure. No redundancy. Database queries that will collapse at 10x load. These problems aren't visible in a pitch deck. They're only visible when you look at the actual system.
Real Example:
A payment API founder pitched impressive growth: 10,000 transactions per day, doubling monthly.
I asked to see the database schema. Every transaction wrote to a single table with no partitioning. At 100,000 transactions per day, the database would lock. At 1 million, it would crash. The architecture couldn't support the growth they were pitching.
Investors saw growth. Operators saw a time bomb.
The Unit Economics Illusion
Investors ask: "What's your gross margin?"
Operators ask: "What's your fully-loaded cost per transaction?"
Most founders calculate gross margin by subtracting direct costs from revenue. Infrastructure costs, payment processing fees, maybe some support costs. They report 60-70% gross margins and investors are satisfied.
But they're missing half the costs. Fraud prevention. Compliance monitoring. Customer success. Technical support. Incident response. These costs scale with volume but aren't counted as direct costs. When you include them, that 70% gross margin becomes 40%. Or 20%. Or negative.
Operators know that infrastructure costs compound in ways that aren't obvious from a P&L.
We've seen this pattern repeatedly. A fintech company reports 65% gross margins. We model the fully-loaded costs including fraud, compliance, and support. Actual margins: 35%. Still viable, but very different from what was pitched. The company needs to be twice as efficient to hit profitability targets.
The Scalability Assumption
Investors ask: "Can this scale?"
Operators ask: "What breaks first when you 10x?"
Everything scales until it doesn't. The question isn't whether your system can scale in theory. It's what breaks first in practice, and how much it costs to fix.
Most infrastructure companies hit their first scaling wall between 10x and 100x growth. The database that handled 1,000 requests per second starts timing out at 10,000. The API that responded in 100ms starts taking 2 seconds. The monitoring system that tracked 100 servers crashes at 1,000.
These aren't hypothetical problems. They're predictable based on architecture. Operators can see them coming. We know which patterns scale and which don't. We know what needs to be rebuilt and when. We know the cost of fixing these problems before they become emergencies.
Common Scaling Bottlenecks:
• Database queries without proper indexing
• Synchronous operations that should be async
• No caching strategy
• Single points of failure
• Insufficient monitoring and alerting
• Manual operations that need automation
Investors assume these problems will be solved when they arise. Operators know they need to be solved before they arise, and that costs time and money.
The Technical Debt Reality
Investors ask: "How fast can you ship features?"
Operators ask: "How much technical debt are you accumulating?"
Technical debt is invisible to investors. It doesn't show up in metrics. It doesn't appear in demos. But it compounds like financial debt, with interest that grows over time.
Every shortcut taken to ship faster creates debt. Every "we'll fix it later" decision adds to the balance. Every feature built on top of shaky foundations multiplies the problem. Eventually, the debt becomes so large that the team spends more time servicing it than building new features.
Operators can see this in the code. We see the quick fixes that became permanent. We see the workarounds that became dependencies. We see the architecture that was meant to be temporary but became load-bearing. We know how much it will cost to pay down this debt, and we know that cost grows exponentially if left unaddressed.
The Operational Complexity Gap
Investors ask: "What's your customer acquisition cost?"
Operators ask: "What's your operational cost per customer?"
Infrastructure businesses have operational costs that don't scale linearly. Every new customer adds complexity. Different integration requirements. Different compliance needs. Different support expectations. Different failure modes.
This operational complexity is hidden in early stages. When you have 10 customers, you can handle everything manually. At 100 customers, you need some automation. At 1,000 customers, you need robust systems. At 10,000 customers, you need operational excellence or you drown.
Investors see customer growth. Operators see operational burden.
We've seen companies that looked great on paper - strong growth, good retention, reasonable CAC - but were operationally unsustainable. Every new customer required manual setup. Every integration was custom. Every support ticket required engineering time. The business was growing, but it wasn't scaling.
The Security Posture Blind Spot
Investors ask: "Are you SOC 2 compliant?"
Operators ask: "Show me your security architecture."
SOC 2 compliance is a checkbox. Security architecture is a system. You can be SOC 2 compliant and still have fundamental security problems. Unencrypted data at rest. Weak access controls. No audit logging. Insufficient monitoring. These problems aren't visible in a compliance report. They're visible in the code and infrastructure.
For infrastructure companies, security isn't just about preventing breaches. It's about trust. One security incident can destroy years of reputation. Customers don't switch infrastructure lightly, but they'll switch immediately if they lose trust in your security.
Operators evaluate security at the architecture level. We look at how data flows through the system. We check encryption at rest and in transit. We review access controls and audit logs. We test incident response procedures. We know that security is a system, not a feature, and we can see when it's been bolted on rather than built in.
The Team Capability Assessment
Investors ask: "What's your team's background?"
Operators ask: "Has your team scaled systems before?"
Résumés don't tell you if someone can scale infrastructure. You need to know: Have they handled production incidents at 3am? Have they debugged performance problems under load? Have they made architectural decisions that held up at scale? Have they built systems that other engineers could maintain?
These questions reveal operational maturity. A team that's never scaled infrastructure will make predictable mistakes. They'll optimize prematurely. They'll build for scale they don't have yet. They'll miss the problems that only emerge in production. They'll learn these lessons eventually, but learning them with customer money is expensive.
Green Flags in Team Assessment:
• War stories from production incidents
• Specific examples of scaling challenges overcome
• Understanding of trade-offs, not just best practices
• Operational discipline (monitoring, alerting, runbooks)
• Ability to explain technical decisions to non-technical stakeholders
The Reliability Tax
Investors ask: "What's your uptime?"
Operators ask: "What does it cost you to maintain that uptime?"
99.9% uptime sounds impressive. But achieving it requires investment. Redundant systems. Automated failover. 24/7 monitoring. On-call rotations. Incident response procedures. Disaster recovery testing. This infrastructure isn't free. It's a tax on every dollar of revenue.
The reliability tax increases with scale. At 100 customers, you can get away with manual processes. At 1,000 customers, you need automation. At 10,000 customers, you need operational excellence. Each level requires more investment in reliability infrastructure.
Operators know this cost. We've paid it. We know that moving from 99% to 99.9% uptime might cost 2x in infrastructure. Moving from 99.9% to 99.99% might cost 5x. These aren't linear costs. They're exponential. And they're necessary for infrastructure businesses where downtime is existential.
Why This Matters
The gap between what investors see and what operators see explains why so many infrastructure investments fail. The pitch looks great. The metrics look strong. The team looks capable. But the underlying system can't support the growth being projected.
Infrastructure investing requires operational expertise, not just financial analysis.
This is why we evaluate infrastructure companies differently. We look at the code. We model the costs. We understand the architecture. We know what breaks at scale. We've been operators ourselves. We know the difference between a system that works in a demo and one that works in production.
When we invest, we're not guessing. We're backing systems we've already evaluated at the operational level. We know the technical risks. We know the cost structure. We know what needs to be fixed and when. We know because we've built these systems before.
This operational depth is our advantage. It's why we can move quickly when we have conviction. It's why our hit rate is higher. It's why we can support portfolio companies with more than just capital. We're operators with capital, not investors trying to understand operations.
If you're building infrastructure and want investors who actually understand what you're building, let's talk.
Jarred Taylor
Capital at the inflection.