10 Questions to Ask Before Pitching an Investor

May 14

I’ve raised capital across film, real estate, and startups—and if there’s one thing I’ve learned, it’s that not every investor is worth your time.

Too many founders fire off pitch decks to anyone with “VC” in their LinkedIn title. That’s not strategy—that’s desperation.

Before you pitch an investor, here are 10 essential questions to ask to avoid dead ends, protect your cap table, and actually close a deal.

1. Do They Invest at My Stage?

If you’re pre-revenue and they’re Series B only—you’re wasting time.

Use USInvestorData.com filters like:

“Check size”
“Funding stage”
“Last deal activity”

Ask yourself: *Do they write checks for companies like mine—now?

2. Have They Invested in My Sector Before?

Investors who “kind of” understand your space are dangerous.

You want someone who knows the terrain and brings real insight (not just capital).

Example: If you’re in FinTech, avoid generalist angels.

At FilmMoney, we only lend to film projects with pre-sales—not speculative scripts.

3. How Many Deals Do They Actually Close?

Some investors take 500 meetings a year… and fund 3.

Don’t chase ghost money.

Pro Tip: Use our database to see past deals and timelines.

4. Do They Lead Rounds or Only Follow?

A lead investor sets terms, negotiates valuation, and brings confidence to the round.

Followers only come in once someone else takes the risk.

Ask: Are you typically a lead investor?

5. What Is Their Average Check Size?

Don’t pitch a $3M round to someone who writes $100K checks.

Conversely, don’t seek $500K from a growth equity firm with a $20M minimum.

Match your raise to their write-size sweet spot.

6. Do They Provide Strategic Value Beyond Capital?

Money is easy. Strategy, network, and trust aren’t.

Ask:

“What role do you usually take post-investment?”
“Can you share examples of how you’ve helped founders grow?”

7. How Long Is Their Due Diligence Process?

Speed matters. Some investors close in 3 weeks. Others take 3 months and ghost you.

Ask upfront: What does your process look like from pitch to close?

8. Who Else Needs to Sign Off?

Decision-maker ≠ person you’re meeting with.

If they’re an associate, you’re not pitching the real power.

Ask: Who makes final decisions on new investments?

9. What’s Their Exit Philosophy?

You want aligned incentives.

Some funds push early exits. Others want to ride it long-term.

You need to know what you’re signing up for.

Ask: How do you define a successful exit?

10. Are They a Cultural Fit?

This is a relationship, not a transaction.

If they don’t believe in your mission, your values, or your leadership—walk away.

My rule: If I wouldn’t want to build with them for 5 years, I don’t take their money.

Final Thoughts: Fundraising Is a Two-Way Vetting Process

Investors are not doing you a favor by meeting with you. This is a mutual evaluation.

At USInvestorData.com, we give founders access to real, verified investor data:

Stage focus
Sector interest
Check size
Recent deal activity
Location and founder preferences

Don’t pitch blind. Do your homework—then pitch with purpose.

David Brown