🧠 170 Questions Every Founder Should Ask to Reduce Risk

Startups don’t fail because the founders didn’t work hard. They fail because founders made assumptions they didn’t test.Startups don’t fail because the founders didn’t work hard.

They fail because founders made assumptions they didn’t test.

Startups don’t fail because the founders didn’t work hard.

That’s why I put together a tool I wish I had years ago:

📋 A curated list of 170+ questions across 17 categories designed to help founders reduce risk, validate decisions, and build smarter.

This isn’t a theory. It’s a practical, boots-on-the-ground resource to help you pressure-test your business before spending months (or millions) building something that doesn’t work.

💡 Why This Matters

Most founders are optimists by default, which is why we build in the first place. But unchecked optimism leads to blind spots.

If you’re not actively testing your assumptions about:

• The problem you’re solving

• The customer’s behavior

• Your pricing, channels, team, tech, and market

…then you’re not reducing risk — you’re compounding it.

This question list is designed to help you surface and prioritize assumptions early on while you still have time to adjust.

🧩 What’s Inside the 170-Question List

The questions are organized into 19 strategic categories, including:

• ✅ Technology Feasibility — Can we actually build this, and should we?

• ✅ Problem Validation — Is this truly painful enough for someone to care?

• ✅ Customer Demand & Behavior — Will they change their behaviour to use this?

• ✅ Pricing & Viability — Will they pay? How much? How often?

• ✅ Market & Competition — Are we in a space worth winning?

• ✅ Regulation — Are there legal or compliance blockers we’re ignoring?

• ✅ Team & Talent — Do we have the right people to execute?

• ✅ Distribution Channels — How will we reach people at scale?

• ✅ Capital Requirements — Do we really know how much we need?

• ✅ User Retention & Engagement — Can we keep users coming back?

…and more

Each question is paired with:

• 📌 Why the question matters

• 🛠 Suggested ways to test or answer it

• 🔄 Whether it’s best asked in an interview, survey, or internal session

👀 A Few Sample Questions

Here’s a taste of what’s inside:

• Is this a top 3 problem for the customer — or just a nice-to-have?

• What happens if the customer doesn’t solve this problem at all?

• How long does it take for a new user to see real value?

• Can our onboarding process scale 10x without breaking?

• What’s our CAC, and how does it vary by channel?

• Do we have a clear backup plan if we can’t raise capital?

• Are there legal or regulatory shifts that could impact our space in 12 months?

These questions help founders move from guesswork to grounded decision-making — and give you a massive head start on building something that works.

🚀 Who This Is For

This list is for:

• 🧱 First-time founders building from scratch

• 🏗 Seed-stage teams preparing to raise

• 💡 Product leaders launching something new

• 🎯 Anyone who wants to pressure-test an idea before going all-in

Whether at the idea stage or preparing for Series A, this is your chance to slow down, zoom out, and test what you assume is true.

📥 Want the Full List?

I’ve bundled the full 170+ risk-reduction questions into a spreadsheet and Notion dashboard, ready for use with your team, advisors, or internal planning.