🚀 How to test co-founder compatibility?

3 tactics to test co-founder compatibility

🧪 Prioritize speed, clarity, ownership, curiosity and openness

• Speed: Do they move fast or get stuck in analysis paralysis?

• Clarity: Can they explain complex ideas simply? If they can't make you understand their thinking, how will they explain it to customers or investors?

• Ownership: Do they take responsibility when things go sideways, or do they play the blame game? (Spoiler alert: things will definitely go sideways)

• Curiosity: Are they asking the right questions and digging deeper, or just nodding along? Curious people find solutions that others miss

• Openness: Do they hear your feedback and seriously consider it? Or do they dismiss anything anyone else suggests?

• Keep in mind, both of you are evaluating each other early on; anyone can walk away whenever with no drama and no hard feelings

🛠️ Collaborate on a trial project

• Choose a project that uses every co-founder’s abilities and has a real impact to the actual business idea:

  • Find something that bugs all of you and try to solve it to see if you approach problems similarly; the goal is to see how you communicate, divide tasks, and handle real challenges

  • Example: 

    • Design and validate a specific feature

    • Research and recommend a go-to-market strategy for one customer segment

    • Build a small tool or process that your team actually needs

• There are 2 main approaches:

  • The Sprint: Work together on a trial project that you can finish in 1-4 weeks max

    • Quick, clean, and you'll know pretty fast if you click

  • The Marathon: Start working together more casually over a few months

    • The upside? You get a real feel for the partnership 

    • The downside? You might invest months only to discover you're not compatible and walk away empty-handed

• Nobody gets paid: You're not hiring each other or paying for each other's time; you're both figuring out if you want to work together 

• Figure out intellectual property (IP) upfront (e.g. your code, designs, ideas, and anything else) by deciding who owns what you build during the trial

  • Option 1: Company owns everything (most common)

    • Any work done during the trial belongs to your company

    • If they join as co-founder: great, they get equity in the company that owns their work

    • If they don't join: you keep the work, they walk away clean

  • Option 2: Everyone keeps their own IP until they join

    • Everyone owns what they create during trial

    • This protects each individual, but creates issues if they don’t join after creating IP that is core to the company

🤝 Discuss equity expectations

• See if you’re directionally aligned early on by discussing it at a high level even if you save exact numbers for later

• There are typically 2 camps of thought on how co-founders should split equity:

  • Equal Partnership: Some prefer it when everyone has equal skin in the game and everyone feels equally valued and motivated

  • One Person as Tiebreak: Others prefer the "someone needs to be the tiebreaker" approach where one person has slightly more equity for decision-making power

• If one co-founder is bringing way more to the table than the other, think about splitting things unequally

2 traps to avoid

🚨 Avoid trial projects that become endless, free labor traps, or overly perfectionist

• The endless project: If scope keeps creeping and timelines keep extending, that's how they'll run your startup too

• The free labor trap: You're evaluating each other, not getting free consulting work; make sure it's mutual

• The perfectionist project: If they can't ship something "good enough" for a trial, they'll struggle with startup speed

🚨 Delaying breaking up

• If you’ve noticed lack of compatibility, it’s time to move on quickly without wasting each other’s time

• If it doesn’t work out for any reason, leverage this template to reach out to your co-founder candidate:

  • "Hey, I learned a ton working together on this. I don't think our working styles are the right fit for a co-founder partnership, but I really appreciate your time and great work."

1 tool to leverage

📖 Best practice on testing co-founder compatibility

• It’s common to take 3 to 6 months to hire an executive; the same amount of care should be taken for a co-founder

• Use these 50 questions to explore with a co-founder as a starting point to knowing your co-founder better

Bonus: 1 trend to spark startup ideas

📈 Alternative capital is reshaping reinsurance and accelerating specialty-insurance innovation

• Alternative reinsurance capital hit a record $121B in 2025 (up 60%+ over the decade) and now accounts for 15% of total industry capital

• Reinsurance can provide attractive, uncorrelated returns (north of 14% last year and higher in 2023)

• More diverse capital reduces pricing volatility after catastrophes and increases Property & Casualty (P&C) coverage and affordability

• Rising climate risk, social inflation, nuclear verdicts, and catastrophe clustering are driving demand for tech-enabled specialty underwriting; AI-first risk modeling, automated portfolio steering, and data-rich program design are becoming core differentiators

• New capacity + rising complexity = fertile ground for opportunities::

  • AI-native specialty managing general agent (MGA): Fast-launch programs using fronts/captives, automated underwriting, and dynamic risk management; U.S. MGA premiums have doubled in 5 years

  • Modern fronts + carriers: Scalable capacity infrastructure supporting multiple programs; more complex and capital-heavy but highly expandable

  • Data + modeling platforms: Real-time risk models, program-profitability tools, and alternative-capital diligence platforms that unlock larger capital flows.

  • Liquidity + capacity marketplaces: Systems matching investors with underwriting opportunities, improving liquidity, transparency, and price discovery.