For a few years now I’ve worked with startups in a way not everyone likes: I don’t charge a fee or a retainer, I take a stake in the company. I’ve explained at length why I work for equity, but the practical consequence is simple: every “yes” I say costs me time, and time is the one thing I can’t get back. So I’ve learned to make the most of a first meeting.
A first meeting usually lasts about 30 minutes. That’s not enough to decide whether I get involved in a company. It is enough to decide whether it’s worth another hour, and then another ten. Below is my checklist, split roughly by the clock. It isn’t science, it’s simply how I look at things.
Minutes 0–8: the founders
I always start with the people, because at this stage the product will change three times and the market may get redefined, but the team stays. I look at four things.
- Commitment. Are they full-time on this, or is it “something we do in the evenings, after work”? Have they put in their own money? The amount doesn’t matter; what matters is that they have something to lose.
- Coachability. I ask an awkward question or raise an objection. Some defend themselves as if they were in court; others say “we hadn’t thought of that, interesting.” I can help the second kind.
- Complementary skills. Two developers with nobody who can sell, or two salespeople with nobody who can build, is a problem. I wrote a while back about how to choose a co-founder, and I end up in the same place: I want to see who does what.
- Honesty about numbers. I ask how many active users they have. If the answer comes nicely rounded up and then gets “corrected” at the second question, I’ve learned something important, and it isn’t about the product.
Minutes 8–13: the problem and who pays
Here I want a single sentence: what pain do you solve, and for whom. If a founder needs five minutes to explain it, the customers probably don’t get it either.
Then I ask something that sounds trivial: who actually pays? The user and the buyer aren’t always the same person. Say, hypothetically, you have an app for school students. The student uses it, the parent pays, maybe the school recommends it. Each has different reasons. A “real” problem is one someone specific already pays for today, in money or in wasted time, not one people politely describe as “nice to have.”
Minutes 13–18: the market and the timing
I’m not impressed by the slide that says “the global market is worth 300 billion.” Any market is huge if you define it broadly enough. I prefer the qualitative argument: who are your first hundred customers, where do you find them, how often do they have the problem, and what does the road from them to the next ten thousand look like.
The second question is about timing: why now? What has changed in technology, regulation or people’s behaviour that makes the idea work today when it didn’t five years ago? Plenty of good ideas died because they came too early. A founder with a clear answer to “why now” has thought about the market, not just the product.
Minutes 18–23: traction and unit economics, in plain words
I don’t need a five-year financial model in a first meeting. I need three numbers, even rough ones, and I want to hear how the founder talks about them.
- What it costs to acquire a customer (CAC). What you spent on marketing and sales last month, divided by the number of new customers. “We don’t know, it came organically” is fine early on, but you should know where from.
- How long customers stay (retention). Of the people who started three months ago, how many still use the product? I think retention is the most honest metric: you can buy users, you can’t buy their loyalty.
- What you make per customer (margin). After direct costs, is anything left? A customer who brings in less than they cost isn’t growth, it’s a hole that gets deeper faster.
The simple rule: over time, a customer has to bring in clearly more than it cost to acquire them. If that’s not true yet, I want to hear why the founder believes it will be, and what test they’re running to find out.
Minutes 23–26: business model and competition
How do you make money: subscription, commission, direct sales, advertising? I’ve built online stores, an online flower shop and a SaaS platform, so I know each model has its own cash rhythm and its own traps. I want to see that the founder chose deliberately, not “we’ll figure out monetisation later.”
Then I ask about competition. If the answer is “we have no competition,” a little red light goes on. Either the founder hasn’t looked, or there’s no market. You always have competition, even if it’s a spreadsheet or the customer’s habit of doing nothing. I much prefer someone who tells me: “these are the three players, they’re good at this, we’re better at that, and here’s why it matters.”
Minutes 26–30: what they’re asking for, and why
The last minutes are about what they want from me or from an investor. How much money, for how long, and what they’ll prove with it. “We need money for marketing” isn’t a plan. “With this amount we’ll know within 12 months whether an acquisition channel is profitable” is.
I also look at how realistic the ask is. An inflated valuation doesn’t necessarily scare me, but it tells me how well the founder knows the market. And if they want an advisor, I want to know specifically for what: sales, international expansion, product, fundraising.
Red flags and green flags
To make it easy to remember, here’s the short list:
- Red: “we have no competition”; numbers that change from one question to the next; founders who interrupt and contradict each other in front of you; one person does everything and won’t delegate; a “weekend project”; defensive answers to every objection.
- Green: they say “I don’t know, but we’ll find out by next week”; they talked to dozens of customers before writing code; they know their numbers by heart, including the bad ones; they have a clear answer to “why now”; they own their past mistakes; they ask me awkward questions too.
Thirty minutes is not an investment decision
Let me be clear: in 30 minutes I don’t decide to invest. I decide whether it’s worth digging deeper. Due diligence comes after that: the real numbers from the accounts, the contracts, the cap table, intellectual property, conversations with customers, checking what I was told. Like everyone, I’ve seen Romanian startups with huge potential that looked excellent on slides and much less so on paper. The first meeting filters; it doesn’t confirm.
Advice for founders: how to prepare
- State the problem in one sentence and practise it until it comes naturally.
- Bring the three numbers (CAC, retention, margin), even if they’re rough. Be honest about how solid they are.
- Do your homework on the competition and show that you respect it.
- Say clearly what you’re asking for, how much, and what for. Don’t make the investor guess.
- Don’t fill 25 minutes with your pitch. Leave room for questions: that’s where the decision actually gets made.
- Bring your co-founders. I want to see how you work together, not just hear one of you talk about the others.
The best founder isn’t the one with an answer to everything, but the one who knows exactly what they don’t know yet and has a plan to find out.
What’s the first question you ask a startup? Or, if you’re a founder, what was the hardest question you’ve had to answer in a first meeting?