A resource list created for Episode 5: Vetting Cofounders.
Step 1: Take Off the Rose-Colored Glasses
Before committing to a partnership, clear your head of excitement about the person or project. First, privately ask yourself hard questions about this person. Then, ask them a set of direct questions and analyze their answers.
Step 2: Questions to Ask Yourself
Answer these privately before speaking with your potential cofounder.
Relationship History & Reputation
- Where did I meet them, and how long have I known them?
- Have I worked with them before? If so, how did it go?
- Who else have they worked with, and what do I know about those people?
- Do they maintain long-term friendships and professional relationships?
- Do they have a reputation for integrity? How do I know?
- Have I spoken to mutual contacts about their work ethic and character?
✅ Look for: A history of stable, positive relationships and work experiences. Frequent falling-outs or burned bridges are red flags.
Skills & Fit for the Business
- Have I seen proof of their work (portfolio, references, testimonials, real-world impact)?
- What level of experience do they have (entry-level, mid-career, expert)? For which skills?
- What type of skills will the business need in the future?
- Do their strengths complement my weaknesses?
- Will we need additional team members to fill gaps? How does this factor into our working relationship?
✅ Look for: Clear evidence of competence, a track record of delivering results, and an ability to scale with the business.
Values & Working Style Compatibility
- What is their motivation for joining this business?
- What are their values and worldview? How do they approach the world and other people? Are they trusting or cynical? Empathetic or demeaning?
- What is their vision for the business? Does it match mine?
- What are their long-term goals? • How do they handle boundaries, pressure, and setbacks?
- How do they deal with drama? Do they create it?
✅ Look for: Genuine commitment, shared values, and the ability to handle stress in a productive way. If they thrive in chaos and you need stability, that’s a mismatch.
Availability & Commitment
- What is their availability, and does it match mine?
- Does their stage of life allow them to commit the necessary time and energy?
- What are my expectations for the skills they bring to the table?
- What are my expectations for their financial contributions?
- What am I willing to give in equity, and what are they asking for?
✅ Look for: Realistic availability and a financial/emotional commitment that matches their equity ask. If they want 50% but can only contribute 10% of the effort, that’s a problem.
Conflict & Crisis Management
- How do they deal with conflict? How do I?
- How will we handle a falling out?
- What constitutes an emergency?
- How do they respond to boundaries?
- How do they manage people?
✅ Look for: A history of handling conflict professionally, a clear sense of urgency, and a leadership style that aligns with your company culture.
Step 3: Questions to Ask Your Potential Cofounder
Go through these directly with them. Take notes on their responses.
Background & Experience
- What’s your professional background?
- Have you worked on similar projects before?
- Can you share examples of your work or success stories?
- Do you have references I can speak with? Both colleagues and clients?
✅ Watch for: Confidence in discussing past work, clear examples, and a track record of impact. If they dodge the question or can’t point to real results, be cautious.
Vision & Motivation
- Why do you want to be part of this business?
- What’s your long-term goal—where do you see yourself in 5-10 years?
- What is your vision for the business?
- How do you define success in a business partnership?
✅ Watch for: Alignment between their goals and yours. If they’re looking for a quick cash grab and you want long-term growth, that’s a mismatch.
Commitment & Availability
- How much time can you commit to this business weekly?
- Do you have other obligations that might conflict?
- Are you prepared to invest financially?
- What financial contributions are you expecting to make?
- What do you expect in terms of equity?
✅ Watch for: A clear, honest answer. If they’re vague or overpromise, they might underdeliver when it matters.
Decision-Making & Conflict Resolution
- How do you handle disagreements in a business setting?
- Have you ever had a business conflict before? How was it resolved?
- How do you react when things don’t go as planned?
- What do you consider an emergency?
- How do you handle boundaries in professional relationships?
✅ Watch for: Evidence that they handle conflict maturely and constructively. Avoid people who are defensive, aggressive, or blame others.
Working Style & Leadership
- How do you like to work? Do you prefer structured plans or a more flexible approach?
- How do you handle stressful situations?
- Have you managed teams before? How do you approach leadership?
- How do you deal with workplace drama? Do you create it?
✅ Watch for: A working style that complements yours and a leadership philosophy that aligns with the company’s needs.
Step 4: Compare Answers & Reflect
After this conversation, step back. Do their answers align with what you already knew? Did they provide clear, honest responses? Are there any contradictions or red flags?
Before moving forward, make sure you can confidently say:
✔️ You trust them.
✔️ Their skills and goals align with yours.
✔️ They are fully committed.
✔️ You can work through conflict together.
If any of these feel shaky, think twice before signing on the dotted line.
Moving Forward
If you feel confident enough to move forward, consider starting with a low-risk, “practice” project to test your working dynamic. Issues will inevitably arise, and the best way to prepare for the challenges ahead is to observe how your potential cofounder handles real-world decision-making and conflict.
Vetting Opportunities
Use these exercises to assess problem-solving, collaboration, and leadership skills before making a long-term commitment:
- Negotiate equity together – Discuss financial contributions, sweat equity, and long-term expectations.
- Hire and manage a vendor – Work through the selection process, negotiations, and ongoing communication.
- Collaborate on a consulting project – Partner on a short-term engagement to test compatibility under real deadlines.
- Define role expectations – Clearly document responsibilities, identify gaps, and determine who will cover them until hiring is possible.
- Plan for operational emergencies – Decide who will be on call for weekend, evening, and holiday issues.
- Build a financial forecast – Align on revenue projections, cost structures, and funding strategies.
- Develop and pitch an investor deck – Work together to craft a compelling pitch and present it to potential investors.
Final Thought: Test Before You Commit
Cofounder relationships are like marriages—easy to get into, legally and emotionally exhausting to get out of, and almost guaranteed to involve at least one argument about money. Be intentional. Ask the hard questions early. Stress-test your partnership before making it official.
If you realize you’re about to co-parent a business with someone who dodges tough conversations, thrives on chaos, or thinks “we’ll figure it out later” is a financial strategy—run. Fast.
But if they handle challenges with clarity, integrity, and a sense of humor, you just might have found your ride-or-die in the startup trenches.