Going to an investor conference this month? Here are the 15 questions you should know cold — to nail your conversations and leave a lasting impression.
This article is part two in our three part-series helping startup founders prepare for major startup- and investor conferences. Read part I and part III.
Investor conferences are not pitches. They are conversations. But make no mistake: in the 10 minutes you have with a partner over coffee or an principal at a cocktail table, you are being evaluated. The investors in the room have heard thousands of founders. They can smell preparation — and they can smell the lack of it just as fast.
The good news? The questions are largely predictable. Below are the 15 questions that come up again and again at early-stage investor conferences. Master these, and you walk in with confidence. Wing them, and you are luck to walk out with a polite “send me your deck” hanging in the air.
We’ve split them into three tiers — and then we’ll follow two founders, Jack and Jill, as they each work the room.
The 15 Questions Every Founder Must Know Cold
Part 1: The Easy Ones
These should roll off your tongue without hesitation. If you stumble here, the conversation is already over.
1. What’s your revenue? Know your current ARR or MRR, your growth rate month-over-month, and whether you’re pre-revenue. Be precise. “Around half a million” is not an answer. 50.000 MRR; growing 30% month-over-month is.
2. What does your team look like? Who are the co-founders, what’s their background, and why are they the right people to build this? Investors bet on teams first. Have a crisp, confident answer.
3. How many customers do you have? Total customers, paying customers, and ideally your logo mix. If you’re B2B, name a few if you can. Numbers here signal traction — or the absence of it. Add in conversion rates to spice up the conversation.
4. What’s your business model? How do you make money? Subscription, usage-based, transactional, licensing? Keep it simple. If your business model requires a slide to explain, practice explaining it without one.
5. What stage are you at? Pre-seed, seed, Series A? How much have you raised, from whom, and what did you accomplish with it? Set the context clearly before anything else.
Part 2: Intermediate Level
These separate the prepared founders from the casual ones. Investors use these to gauge how commercially sharp you are.
6. What’s your (funding) timeline? When are you planning to close? Are you actively raising right now, or exploring? Investors need to know if there’s urgency — and whether their timeline can match yours.
7. Do you have a lead? If you’re approaching a seed or Series A, investors want to know who is anchoring the round. If you don’t have a lead yet, have a clear answer about who you’re in conversation with and what your lead criteria look like.
8. What are your key unit economics? CAC, LTV, LTV:CAC ratio, payback period. Know these numbers cold. If you’re early and don’t have statistically significant data yet, say so — but explain what signals you’re seeing and what you expect them to mature into.
9. Walk me through your top metrics. Beyond unit economics: churn, NRR, DAU/MAU, GMV, fill rate — whatever is most relevant to your business. Know your north star metric, and know why it’s the right one to track.
10. What does your cap table look like? Who owns what? Are there any messy early structures, convertible notes piling up, or SAFEs that will create issues at a priced round? Clean cap tables signal clean thinking.
Part 3: Advanced Questions
These are the questions that sort the truly prepared founders from everyone else. Nail these, and you’ll be remembered.
11. How much capital do you need — fully funded? Investors often think in terms of the full journey, not just the current round. How much total capital will it take to build a market-leading company? Walk them through the current raise and the longer-term capital roadmap. Don’t have the number? Go to work
12. Walk me through your economic scenarios — high case, mid case, low case. What probabilities do you put on each? This is where investors test your intellectual honesty. They want to see that you understand the range of outcomes, can articulate what drives each, and aren’t just pitching the dream scenario. Assign real probabilities. If you say 80% chance of the high case, they will push back hard.
13. What are you doing for early investor liquidity? Especially relevant at growth stage: are you thinking about secondaries, structured liquidity programs, or anything that allows early backers to realize some return before a full exit? This signals maturity and respect for your investor relationships.
14. What’s your exit strategy? IPO? Strategic acquisition? Are there natural acquirers in your space? Who has bought comparable companies, at what multiples, and when? You don’t need a fixed answer — but you need a thoughtful one.
15. Who else is in the round, and can we see their papers? Investors do diligence on each other. Who are your co-investors, what are the terms, and is the round structured in a way that works for all parties? Experienced investors will want to know they’re sitting alongside people they respect.
Bonus — The One That Catches Everyone Off Guard: “What’s the probability that you build a globally top-tier company in this space?” This is the hardest question of all. Not because you can’t answer it — but because answering it well requires both conviction and intellectual honesty in the same breath. We’ll see how Jack and Jill handle it below.
The Two Founders: Jack vs. Jill
To bring these questions to life, let’s follow two founders through the same investor conference. Both are raising a seed round. Both have interesting companies. But only one of them has done the work.
Jack — Founder of BuildStack
The Company: BuildStack is a project management platform for construction subcontractors — a sector Jack believes is massively underserved by tools like Procore and monday.com.
The Idea: Strong. The market: real. Jack himself spent four years working for a mid-size electrical contractor, so he knows the pain intimately. On paper, he’s a compelling founder.
At the Conference: Not so much.
Jack arrives with energy and enthusiasm. He works the room well socially. But when a partner from a well-regarded construction-tech fund pulls him aside for a conversation, things unravel fast.
Investor: “So what’s your revenue right now?”
Jack: “We’re still pretty early, so we haven’t fully focused on revenue yet — we’re more in the product-building phase. But we have some pilots going.”
What went wrong: Saying “we haven’t focused on revenue” at a seed-stage company raises immediate flags. Even if revenue is zero, Jack should own it confidently: “We’re pre-revenue. We have four paid pilots at $500/month each that convert to full contracts in Q2.” That’s a story. “We haven’t focused on it” is not.
Investor: “How many customers do you have?”
Jack: “We have about 15 companies that are using the product in some form.”
What went wrong: “In some form” is a killer phrase. It tells the investor that Jack doesn’t distinguish between paying customers, free users, and tire-kickers. The answer should be: “We have 4 paying customers, 8 in active pilots, and 3 who’ve signed LOIs.”
Investor: “Walk me through your unit economics.”
Jack: “Yeah, totally — so we’re working on getting that data together. It’s still early, so the numbers aren’t fully baked yet. But we think LTV is going to be really strong because construction contracts are multi-year.”
What went wrong: Completely. Even with limited data, Jack should have a model. “Our current CAC is approximately $1,200 based on our last three closed deals. At $500/month and an expected 24-month contract length, we’re looking at an LTV of $12,000 — a 10x ratio. We expect CAC to drop as we build outbound, but we’re being conservative.” That’s a founder who knows his business.
Investor: “What probabilities do you put on building a top global company in this space?”
Jack: “I mean — I think we can definitely get there. The market is huge and nobody’s really nailed it for subcontractors specifically. I’m very confident.”
What went wrong: Confidence without structure reads as naivety. Investors don’t want cheerleading. They want calibrated thinking.
Jack leaves the conversation with a “send me your deck.” The investor is polite but moves on within minutes.
Jill — Founder of ClearClose
The Company: ClearClose is a B2B SaaS platform that automates compliance documentation for independent mortgage brokers — a segment Jill identified while working as a compliance officer at a regional bank for six years.
The Idea: Niche. Precise. Exactly what early-stage investors tend to love: a founder with deep domain expertise, attacking a specific, painful problem in a large market.
At the Conference: Jill has prepared for this like she’s running a marathon. She knows her numbers, her narrative, and her answers — but she delivers them like a human, not a robot reading from a spreadsheet.
Investor: “What’s your revenue?”
Jill: “We’re at $28K MRR, growing about 18% month-over-month for the last four months. All from inbound — we haven’t touched paid acquisition yet.”
Why it works: Precise, contextual, and ends with a hook. The investor immediately wants to ask a follow-up.
Investor: “How many customers do you have?”
Jill: “32 paying customers. Average contract is $875/month. Our largest is a broker network with 14 offices — they came in at $3,200/month. We’ve had one churn — a one-person shop who closed down their business.”
Why it works: She distinguishes volume from value, gives a flagship customer example, and proactively addresses churn before she’s asked. That last part builds enormous trust.
Investor: “Walk me through your unit economics.”
Jill: “CAC right now is around $900, almost entirely organic — referrals and content. LTV at current churn of 2.5% monthly is around $35,000, which gives us a roughly 38:1 LTV:CAC ratio. We know that’s unusually strong for this stage, and we think it’s partly because we’re solving a compliance problem — customers don’t leave compliance tools lightly. Our payback period is under two months.”
Why it works: She knows the numbers cold, contextualizes them honestly (“unusually strong”), and explains the structural reason — which also doubles as a competitive moat narrative.
Investor: “Walk me through your economic scenarios. What probabilities do you put on each?”
Jill: “Sure. In our base case — which I’d put at around 55% probability — we close this $1.8M seed round, hire two engineers and one sales rep, and exit next year at $500K ARR heading into a Series A. In our high case — maybe 25% — the broker network deal becomes a full channel partnership, which accelerates us to $1.2M ARR in the same timeframe. In the low case — I’d say 20% — sales cycles stretch and we hit $280K ARR. In that scenario, we extend the runway by staying lean and push the Series A 12 months. We don’t see a scenario where the core problem goes away — compliance burden on independent brokers is only increasing.”
Why it works: Specific numbers. Real probabilities that add up to 100%. An honest low case. And the framing of the low case as a delay, not a death — which is almost always true in strong businesses.
Investor: “What’s the probability you build a globally leading company in this space?”
Jill: “Honestly? I think there’s a 30 to 35% chance we become the dominant compliance platform for independent mortgage brokers in the US — and I think that alone is a very valuable business. The international angle is real but it’s a 5-year story, not a 2-year story, and I don’t want to oversell it. What I can tell you is that in my base case, we build something worth building and worth backing regardless of whether we go global. The optionality is real. The dependency on it is not. You can also see our outcome analysis in our Investor Presentation and our Memo if you want all the details.”
Why it works: She doesn’t inflate the probability to seem visionary, and she doesn’t deflate it to seem humble. She reframes the question around the base case value — and shows the investor that she’s protecting their money, not just pitching her dream. Big bonus, she’s pointing to the materials, without bringing a full data room into the conversation.
Jill ends the conversation with three business cards, two follow-up meetings booked for the following week, and one investor who pulls his partner over mid-conversation to introduce them.
The Takeaway
Jack and Jill didn’t have dramatically different companies. In some ways, Jack’s market is larger. But Jill walked in having done the work — not to perform preparedness, but because she genuinely knew her business inside and out.
That’s what investors are actually testing. Not whether you can recite your LTV:CAC ratio. Whether you’ve thought hard enough about your company that the numbers are just something you know — the way you know your phone number.
The questions above are predictable. The preparation is entirely in your hands.
Walk in like Jill.
Good luck.
(Want to dig deeper? Check out Pawel’s list of 300 questions investors will want to ask).
This article is the second in a three piece series to help founders prepare for key conferences. Part I: The Founder’s Web Summit Checklist: 10 Things You Need to Prepare. Read it here. Part III: Going to Web Summit? Here Are the 15 Questions You Need to Prepare For the Investors You Meet. Read it here.
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