December 14, 2025

10 min read How to Diligence a Deal Beyond the Deck A practical framework for investors to go deeper than the pitch—focusing on risk domains, capital discipline, and founder transparency. Pitch decks are designed to persuade, not to fully inform. They highlight upside, compress complexity, and often gloss over risk. For investors, relying on the deck alone is one of the fastest ways to misprice risk and overestimate execution. Whether you’re an angel investor, family office, strategic, or venture fund, diligence on a deal beyond the deck requires a structured, skeptical, and evidence-driven approach. The goal isn’t to kill deals to build conviction by understanding where things can break and whether the team has the discipline to navigate those risks. Below is a practical framework to go deeper than the pitch and evaluate a company across its true risk domains. 1. Business Model Clarity & Unit Economics   a. How the Company Actually Makes Money Start by stress-testing the revenue model—not the TAM slide. Ask: Is revenue transactional, recurring, usage-based, or contract-driven? Who is the buyer vs. the end user? What triggers revenue recognition? Break down cost drivers: COGS or service delivery costs Sales commissions and customer success Infrastructure, tooling, or third-party dependencies Look for: Clear margin expansion logic Evidence that costs decline with scale, not just assumptions If unit economics don’t work at a small scale, they rarely work later. b. LTV, CAC, and Payback Reality Founders often present optimistic LTV/CAC ratios. Your job is to pressure-test them. Validate: CAC by channel (not blended averages) Sales cycle length by customer segment Retention, expansion, and churn assumptions Ask: How long does it take to recover CAC on a cash basis? What happens to CAC as the company scales? Are early customers representative—or exceptions? c. Pricing Power & Market Sensitivity Understand whether pricing is: Cost-plus Value-based Competitive or commoditized Test: What happens if prices drop 20%? Can customers easily switch? Is pricing driven by ROI, urgency, or convenience? Real businesses survive pricing pressure. Fragile ones don’t. 2. Risk Domains: Where the Business Can Break Great diligence maps risk before upside. Key risk domains to assess: Market risk (is the problem real and urgent?) Product risk (does it work as claimed?) Execution risk (can the team deliver?) Financial risk (capital sufficiency and burn discipline) Regulatory or compliance risk (if applicable) Dependency risk (customers, vendors, platforms) Ask founders directly: “What are the top three things that could kill this company?” How they answer matters as much as what they say. 3. Product Reality vs. Product Narrative   a. Product-Market Fit Evidence Look for proof—not promises. Validate through: Customer usage data Retention and engagement metrics Pilot-to-paid conversion rates Reference calls with real users Red flags: Heavy roadmap focus with light customer evidence Features driving excitement but not retention “Design partners” that never convert b. Roadmap Discipline A strong roadmap is prioritized, resourced, and sequenced. Ask: What gets built next—and why? What’s customer-driven vs. founder-driven? What milestones unlock revenue or margin? Avoid teams chasing breadth before depth. 4. Go-to-Market Execution   a. Sales Motion Fit Evaluate whether the GTM motion aligns with the product and the buyer. Assess: Self-serve vs. sales-led vs. enterprise Founder-led sales dependency Channel vs. direct strategy Red flags: Long enterprise cycles without a capital runway Complex sales motions with junior teams No clear ICP definition b. Pipeline Quality Inspect pipeline health—not just top-line numbers. Look for: Stage conversion rates Deal slippage patterns Customer concentration risk One “logo” does not equal traction. 5. Founder Transparency & Integrity This is where diligence moves from analytical to judgment-based. Strong founders: Share bad news early Acknowledge weaknesses Provide clean, consistent data Don’t over-defend assumptions Watch for: Shifting answers across meetings Overly polished responses to hard questions Resistance to data requests Trust is built through consistency under pressure. 6. Team & Execution Capacity   a. Role Coverage Evaluate whether critical functions are owned: Product Sales Operations Finance Early-stage teams don’t need depth everywhere—but they need awareness of gaps. b. Execution Track Record Ask: What milestones were hit late—and why? Where has the team over- or under-estimated? How do they course-correct? Past execution is the best predictor of future execution. 7. Financial Discipline & Capital Strategy   a. Burn vs. Learning Healthy burn drives learning and de-risking—not just growth optics. Assess: Monthly burn vs. milestone progress Headcount growth vs. productivity Spend aligned to key risks   b. Capital Plan Reality Understand: How long does the current capital last What milestones justify the next raise Downside survival scenarios Ask: “If fundraising takes 6 months longer than expected, what happens?” 8. Cap Table & Incentive Alignment Review: Ownership distribution SAFEs, notes, and preference stacks Employee option pool health Red flags: Overcrowded early cap tables Misaligned investor rights Founder dilution that kills motivation 9. Market Context & Competitive Positioning Map: Direct competitors Indirect substitutes Incumbent responses Assess: Switching costs Differentiation durability Speed of competitive response Winning often depends on timing, not just product quality. 10. Exit Logic & Investor Fit   a. Plausible Exit Paths Ask: Who buys companies like this? At what scale? On what metrics? Hope is not a strategy, exits follow patterns. b. Alignment Check Finally, assess: Time horizon fit Risk tolerance alignment Strategic vs. financial expectations A good deal for someone else can be a bad deal for you. Final Thoughts Diligencing a deal beyond the deck is about discipline, curiosity, and humility. It means resisting the story long enough to examine the structure underneath—and deciding whether the risks are known, manageable, and worth taking. By applying a structured framework, grounded in unit economics, risk domains, founder transparency, and capital discipline, you move from guessing to conviction. The best investors don’t avoid risk. They understand it better than anyone else in the room.   Hall T. Martin is the founder and CEO of the TEN Capital Network. TEN Capital has been connecting startups with investors for over ten years. You can connect with Hall about fundraising, business growth, and emerging technologies via LinkedIn or email: hallmartin@tencapital.group