The Questions You Should Ask Investors
Most founders show up to investor meetings ready to be grilled.
They expect the questions to go one way only, traction, team, market, product, valuation. But here’s the truth: the best founders ask great questions too. Not to impress, but to qualify who’s sitting across from them.
You don’t just need money. You need a partner. And not all money comes with the same energy, expectations, or alignment.
So let’s flip the script.
Here are the questions you, as a founder, should ask investors, segmented by Business Angels and VC Funds.
Questions to Ask a Business Angel
Business angels come in all shapes: the exited founder, the corporate exec, the curious first-timer. Some are incredibly helpful. Some write the check and vanish. You need to know which one you’re dealing with.
Start with the person:
– What attracted you to angel investing?
– What kind of startups do you like to invest in?
– How many companies are in your current portfolio?
– Do you invest solo or with others?
Understand their value beyond the money:
– What’s your background and how do you think you can help us?
– Do you typically help with intros (hires, clients, other investors)?
– Can I speak to a founder you’ve backed? Maybe one where things didn’t go as planned?
Get clarity on the money side:
– What’s your typical check size?
– Do you usually follow on in future rounds?
– Do you expect a board seat or specific rights?
– What’s your ideal investment outcome, how much and when?
Pro tip: the best angels are emotionally intelligent. If they try to dominate the conversation or are overly focused on “what’s my upside,” that’s a red flag.
Questions to Ask a VC Fund
When you meet with a VC fund, you’re talking to an institution. That means structure, multiple partners, internal politics, and usually a bigger check, but also more expectations.
Start with the fund dynamics:
– What’s your fund size and average check at our stage?
– What ownership do you typically target?
– How many new investments do you do per year?
– Do you reserve capital for follow-ons?
Understand how they work:
– Who from your team would work directly with us?
– What does your investment process look like, and how long does it take?
– What are the typical deal breakers at your stage?
Dig into their support system:
– How do you help companies post-investment, operationally, commercially, strategically?
– Do you have a platform team or support services (PR, hiring, fundraising)?
– Can you introduce us to potential customers or later-stage investors?
Check alignment and founder-friendliness:
– What does success look like for you on this deal?
– How do you handle down rounds or rough patches?
– How do you approach secondary sales or founder liquidity?
– Can we speak with a few founders in your portfolio, including one that struggled?
Pro tip: You’re not pitching a deck. You’re choosing a co-pilot. Ask what happens when things go wrong, not just when they go up and to the right.
Good investors expect you to ask these questions. The smart ones want you to.
Because if you’re building something big, the relationship could last 7–10 years. That’s longer than most marriages. So ask boldly.
You’re not just raising money, you’re selecting your future partners.
Want a second pair of eyes on your pitch deck, or need help talking to investors?
