001 | The One Thing Most Entrepreneurs Don’t Ask About (But Should)

Over the past 10 years, I’ve seen many entrepreneurs say “Yes” to investors without asking any questions. This often leads to:

• Fights

• Misaligned vision

• Extreme frustration

Many startups think they should take any funding available, assuming the investor has all the power.

But the wrong investor can slow progress, dilute your mission, or create internal conflicts.

Investors aren't just bringing money—they're becoming partners. So why do only investors do due diligence? As an entrepreneur, you need to ensure this partnership will help your business grow.

Here are 10 things to check when doing due diligence on investors:

1. Track record: Have they helped startups grow through similar stages?

2. Investment style: Are they hands-on or hands-off? Which do you prefer?

3. Portfolio: Any conflicts of interest with their other investments?

4. Exit strategy: Do their return expectations and timeline align with yours?

5. Reputation: Speak with founders they’ve backed—are they supportive or controlling?

6. Value-add: Do they bring expertise, connections, or other resources beyond money?

7. Follow-on investment: Will they support future funding rounds?

8. Personal values: Do their ethics align with yours?

9. Decision-making: How involved will they be in major business decisions?

10. Cultural fit: Will they fit with your team and company culture?

Do your research just like they do. Ask direct questions and don’t hesitate to walk away if the fit isn’t right.

Takeaway: Doing due diligence on investors can lead to better relationships, which are just as important as the funding itself.