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founder-prenup skill

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This skill helps co-founders align on values, vision, conflict style, and decision protocols to prevent startup disputes and foster durable partnerships.

npx playbooks add skill coowoolf/insighthunt-skills --skill founder-prenup

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SKILL.md

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---
name: founder-prenup
description: Use before starting a company with co-founders, when bringing on a new co-founder, or annually as a relationship health check to prevent the 65% of startup failures caused by co-founder conflict
---

# The Founder Prenup

## Overview

A set of critical discussion topics for co-founders to align on **before** starting a company (or to revisit periodically). Designed to prevent the **65% of startup failures** caused by co-founder conflict.

**Core principle:** Assume nothing. If you act based on your values and they act based on theirs, you'll think they're acting strangely—but they're just being themselves.

## The Alignment Checklist

```
┌─────────────────────────────────────────────────────────────────┐
│                    FOUNDER PRENUP CHECKLIST                     │
├─────────────────────────────────────────────────────────────────┤
│                                                                  │
│  ☐ VALUES CLARIFICATION                                         │
│    List top 3-5 core values and compare.                        │
│    (Excellence vs. Work-Life Balance?)                          │
│                                                                  │
│  ☐ VISION OF SUCCESS                                            │
│    Define the end game. (IPO? Acquisition? Freedom?)            │
│    One wants massive venture outcome, one wants "small shop"?   │
│                                                                  │
│  ☐ CONFLICT STYLE                                               │
│    How do we argue? (Seething in silence? Exploding?)           │
│    How quickly do we need resolution?                           │
│                                                                  │
│  ☐ DECISION PROTOCOL                                            │
│    When we disagree, who decides?                               │
│    (Vote? CEO final? Domain expert?)                            │
│                                                                  │
│  ☐ CULTURE DEFINITION                                           │
│    Results-driven vs. Family-feel?                              │
│    Speed vs. Consensus?                                         │
│                                                                  │
│  ☐ OPERATING STYLE                                              │
│    Communication preferences and pet peeves.                    │
│    Working hours expectations.                                  │
│                                                                  │
└─────────────────────────────────────────────────────────────────┘
```

## When to Use

| Timing | Purpose |
|--------|---------|
| Before incorporation | Foundational alignment |
| When adding co-founder | Prevent future conflicts |
| Annually | Relationship health check |
| During tension | Structured de-escalation |

## Red Flag Misalignments

| Topic | Co-founder A | Co-founder B | Risk |
|-------|--------------|--------------|------|
| End Goal | IPO | Lifestyle biz | **Critical** |
| Work Style | 80hr weeks | 40hrs max | **High** |
| Decision | Consensus | Dictatorial | **High** |
| Conflict | Avoid | Confront | **Medium** |

## Common Mistakes

- **Assuming alignment** because you're friends
- **Avoiding the conversation** because it feels awkward
- **Not revisiting** as the company evolves

## Real-World Example

Two co-founders realized too late: one wanted a massive venture outcome, the other wanted a small shop where they knew everyone's name. The painful split could have been avoided with this conversation upfront.

---

*Source: Alisa Cohn (Executive Coach, Thinkers50 Top Startup Coach) via Lenny's Podcast*

Overview

This skill packages a founder prenup: a focused checklist and conversation guide founders use to align expectations, values, and operating norms before forming a company or when tensions arise. It targets the most common source of startup failure—co-founder misalignment—by making assumptions explicit and actionable. Use it to surface dealbreakers early and create repeatable resolution protocols.

How this skill works

The skill walks founders through a short alignment checklist: core values, vision of success, conflict style, decision protocol, culture definition, and operating preferences. It provides prompts to compare answers, identify high-risk mismatches, and decide concrete next steps (e.g., decision rules, roles, or a re-evaluation cadence). It’s designed for initial conversations, onboarding new co-founders, or annual health checks.

When to use it

Before incorporation to set foundational alignment
When adding a new co-founder to prevent future conflicts
Annually as a relationship and strategy health check
When tensions escalate and you need a structured de-escalation
Before major strategic pivots (fundraising, sale, or hiring key execs)

Best practices

Document the agreed answers and store them with governance documents
List top 3–5 core values each and discuss real trade-offs
Agree on a decision protocol for unresolved disputes (CEO call, domain expert, vote, mediator)
Set a review cadence (quarterly or annual) and an explicit exit/transition plan
Call out “red‑line” mismatches that require renegotiation before moving forward

Example use cases

Two friends about to incorporate compare vision: IPO vs. lifestyle—discover a dealbreaker before investment
Adding a technical co-founder mid-stage to align on time commitment and ownership
Annual check that reveals shifting priorities after a major fundraising round
Using the checklist as a neutral agenda in a high-conflict meeting to move from emotion to facts
Defining decision rules before hiring a CEO or signing a large customer contract

FAQ

What if we still disagree after following the checklist?

Agree a formal decision protocol in advance (tie to role, domain expertise, or independent mediator). If disagreement persists on a core value, treat it as a potential dealbreaker and negotiate exit or revised roles.

How often should we revisit the prenup?

At least annually and on major milestones (funding, product pivot, scaling hires). Revisit sooner if stress or recurring conflicts appear.