Questions investors ask in a first meeting, and how to answer

Between 2008 and 2014, 1,942 startups asked Italian Angels for Growth for money. Those that got as far as a meeting gave a brief presentation, then took questions from the members who’d asked to see them. A venture fund isn’t so different. Liz Wessel, a partner at First Round, puts a typical first meeting at 30 to 45 minutes, usually with one partner.

Either way, the questions are more predictable than they feel from the founder’s chair. This guide sorts the questions investors ask by theme, from the team to the cap table, with what a good answer contains and what the investor is really testing. Then the Italian specifics and the questions to ask back. New to fundraising? Start from the beginner’s map, from zero to a first round.

How does a first meeting with an investor work?

Start with the angels. In the IAG study, by Annalisa Croce, Francesca Tenca and Elisa Ughetto, two analysts ran the pre-screening, and nearly 72% of ventures stopped there. You got a meeting only if two or more members raised a hand. Then a screening committee decided who’d pitch again, to the whole assembly, and due diligence waited until €200,000 had been pledged. Twenty-one ventures were funded. That’s 1.1%.

A fund moves differently. Wessel says the first meeting is often with the point partner, sometimes an associate or a principal, and that questions come ‘throughout your entire pitch’. She reads interruptions as a good sign. The partner meeting usually lasts 60 minutes. January Ventures, a two-partner fund, describes a 30-minute first call, a talk at its weekly investment meeting, then an hour with both partners.

So treat the first meeting as a screen. Nobody closes a round in half an hour. The job is to earn the second meeting.

Questions investors ask, theme by theme

Writing on Y Combinator’s blog in 2016, Michael Seibel listed seven things a pitch should answer: what you do, the market, your progress, your unique insight, the business model, the team and what you want. The table adds the cap table and the risks. Treat it as your list of pitch meeting questions to rehearse out loud.

Theme	Questions you’ll hear	A good answer contains
Team	Why you? How did you meet? Who builds the product? Is everyone full-time?	A specific reason you’re the people for this problem, how long you’ve worked together, who writes the code
Problem and market	Who has this problem, and how badly? How big is the market? Why now?	One named customer type, what they do today instead, a bottom-up market size (customers times price)
Product	What does it do today? Can you show me? What comes next?	A demo or screenshots of what customers use now, then one line on the roadmap
Traction	How many paying customers? Monthly growth? Retention?	Three numbers, each with a date and a definition
Business model and unit economics	Who pays, how much, how often? What does a customer cost to acquire? When do you earn it back?	Price, gross margin, CAC and payback in months, and where each figure comes from
Competition	Who else does this? Why will you win? What stops a big player copying you?	Named competitors, including spreadsheets and the status quo, and one advantage you can prove
Go-to-market	How do you find customers? Which channel works? How long is a sale?	The channel behind your last ten customers, the sales cycle, the cost
The round	How much are you raising? For how long? What’s the valuation logic? Use of funds?	Amount, months of runway, the milestone it buys, spending by bucket
Cap table	Who owns what, fully diluted? Any SAFEs, convertibles or option pool?	A current table that includes every instrument that will convert
Risks	What could kill this company? What would make you stop?	Two real risks and what you’re doing about each

Some of these sound like small talk. They aren’t. January Ventures opens with ‘Tell us about you and why you started this company?’ and then asks what in your background makes you ‘the best person to build this company’. Be specific. Say you spent four years selling booking software to dental clinics in Emilia: tell them that, and what it taught you about why clinics cancel. ‘I’m passionate about this space’ tells them nothing.

On traction, the proof that customers want what you sell, precision beats size. Andreessen Horowitz (a16z) warns that ‘letters of intent and verbal agreements are neither revenue nor bookings’. An unpaid pilot with a manufacturer in Brescia is a pilot. Call it one. Our guide to the startup metrics investors want at pre-seed and seed sorts the numbers by stage.

Unit economics, the profit or loss on a single customer, usually comes up as ‘what does a customer cost you?’ Give the full cost: a16z says CAC should be ‘the full cost of acquiring users’. Selling subscriptions? David Skok’s yardstick: in the best SaaS businesses a customer’s lifetime value tops three times CAC, and many recover the CAC in 5 to 7 months. No revenue yet? Admit it, and name the first assumption you’d test. Here’s the arithmetic for CAC, LTV and payback.

The round is where founders improvise most. Fit the amount, the runway and the milestone into one sentence. An invented example: ‘We’re raising €900,000 to last 22 months and reach €60,000 of revenue a month.’ Why about two years? On Carta’s data, US startups raising a Series A in late 2025 had waited a median 1.9 years since their seed. On price, show your reasoning rather than your hopes, and know if the figure is pre-money or post-money before anyone asks.

What are investors really testing?

Mostly you. In the IAG study, compared with the first desk review, ventures turned down at the screening stage (the one with the meeting) were rejected more often for reasons tied to the entrepreneur and the team, and less often for a lack of innovation. Venture capitalists say much the same. Paul Gompers, Will Gornall, Steven Kaplan and Ilya Strebulaev surveyed almost 900 of them: 95% of firms called the team an important factor, and 47% put it first. Picky, too. The average firm looked at roughly 200 companies a year and backed about four.

You’re marked twice on every question: once for the answer, once for the way you give it. Do you know your numbers without opening a laptop? Can you say ‘I don’t know’ when you don’t? What happens to your face when someone doubts your market size? Seibel’s version is blunter, and worth stealing: ‘You don’t need to sound cool. You need to be clear.’

Long answers bury the point. Say your sentence or two, then stop and let the silence sit for a second longer than is comfortable. Whatever they ask next is what’s really worrying them. Missing a figure? Promise it by Friday and send it on Thursday. For the signals behind all this, read what investors look for in a founder with no track record.

The Italian questions: tax incentive, Smart&Start, SRL quotas

Are you a startup innovativa? Can I get the 65%?

An Italian angel will ask early, because it changes their maths. People who invest in a startup innovativa, the special status for young tech companies, can take 65% of the amount off their personal income tax (IRPEF), on up to €100,000 a tax year, if they hold the stake for at least three years. It counts as de minimis aid, the small state aid capped per company, so the startup can’t receive more than €300,000 of it over three years. Its legal representative must also file a request on the government platform before the money arrives.

Someone may bring up the old 30% deduction, which the ministry’s startup page still lists. According to SRL Online, it hasn’t been usable since 1 January 2026: its EU authorisation expired on 31 December 2025 and wasn’t renewed in time. Our comparison of tax breaks for startup investors in Italy and the US covers both.

Is there a Smart&Start loan on the balance sheet?

If you’ve used Smart&Start Italia, expect a question on it. It’s an interest-free loan for 80% of eligible costs (90% in some cases), on plans between €100,000 and €1.5 million, repaid over at most ten years. In eight southern regions you pay back only 70%. An investor reads it as debt with a calendar, so bring the calendar.

Then mention what founders often forget. When third-party investors or individual shareholders put in risk capital, the startup can ask to turn part of the loan into a grant: up to 50% of what they contributed, and never more than half of the total aid. Details are in our Smart&Start guide.

How will my rights work in your SRL?

An SRL has quotas, not shares. Article 2468 of the Civil Code says partners’ stakes can’t be represented by shares, and rights follow the size of the stake unless the deed of incorporation says otherwise. A startup innovativa SRL can create categories of quotas with different rights, non-proportional voting included. That’s usually where investor protections end up, next to a shareholders’ agreement. Asked how a term sheet’s clauses would land in your bylaws? ‘The notary will handle it’ is a weak answer.

What to ask the investor back

A first meeting runs both ways. With an angel group, ask what happens next and how much must be pledged before due diligence starts (€200,000, in the years the IAG study covers). With a fund, start from the 12 VC first meeting questions suggested by Micah Rosenbloom of Founder Collective. These five come first at seed.

• Do you lead? A lead investor sets the terms and usually writes the biggest cheque. Most funds, Rosenbloom notes, ‘will want someone else to lead first’.
• What share of the fund would we be? A small cheque from a large fund is an option for them, not a commitment.
• Reserves, the money kept back for your later rounds. A 4:1 ratio means four euros earmarked for every euro invested now, in theory. Rosenbloom’s warning: don’t assume they’ll use it, ‘especially if you have a rocky start’.
• How far into the fund is this investment? His reason: ‘It’s helpful to know if your potential VC will be around in a few years’ time.’
• What is the diligence process like? And who takes the final call: one partner, or the whole partnership?

Write the answers down the same day, next to the investor’s name in your investor pipeline. By the fifth meeting, they start to blur.

Investor meeting preparation: the checklist for the day before

Rehearse out loud at least once, with someone who’ll interrupt you. That’s what the two mock meetings in our Fundraising Sprint are for. In 14 days it also gets the deck, the numbers, an investor-fit list and the data room ready.

1. Read the investor’s last five deals and one thing a partner has said in public.
2. Seibel’s email test, tonight: send a friend two sentences on what the company does. Questions back, instead of a paraphrase, mean the sentences need another go.
3. Six numbers you should know cold: revenue, growth, burn, runway, CAC, payback. On one sheet, note how you calculate each and which month it’s from. Someone will ask.
4. The ask, rehearsed until it takes ten seconds. Then the fully diluted cap table, with every SAFE, convertible and option on it.
5. The Italian file: startup innovativa registration, de minimis aid already received, the Smart&Start repayment plan and the bylaws, in one folder you can share during the call.
6. Three questions of yours on a sticky note, ‘Do you lead?’ at the top, and tomorrow’s thank-you email already written, with a blank line for whatever you promise.

This article is general information, not legal, tax or investment advice. Tax incentives and public loan rules change: check the official pages or ask a professional before you rely on them.