The eight questions investors ask about you
Investors rarely tell you why they passed. These are the concerns that actually circulate after your meeting, in roughly the order they kill deals.
- "I can't get conviction on the CEO." The biggest one. A compelling CEO can raise on a mediocre idea. A brilliant idea cannot survive an unconvincing CEO. A fundraise is a job interview as much as an investment.
- "They aren't in this for the right reasons." At Octopus we called it a founder's North Star. Without a deep reason to keep going through the inevitable bad years, investors assume you will quit when it gets hard.
- "The founder is lying to me." More common than founders imagine. We once signed a term sheet, then found in final financial diligence that revenue was a tenth of what the founder had claimed. We rescinded, and the company failed soon after. Investors carry stories like that into every meeting.
- "Something is off in the founding team." Too many co-founders, co-founders who are not in the business day to day, everyone titled co-CEO, visible tension in the meeting. One of these is survivable. Three is a rejection.
- "I don't like this person." An investment is a decade of working together. I watched a defence founder's facade slip in a second meeting: the pitch about helping people gave way to plans for surveillance and sales to authoritarian regimes. We rejected him the same day.
- "This team lacks focus." The most common note at seed: too many features, too many pricing models, too many launches at once. Distraction reads as a predictor of failure.
- "The references came back bad." I never stopped at the references a founder gave me. I found former colleagues and reports myself. Glowing chosen referees could not save a founder when nine of ten independent voices said the opposite.
- "A key person is missing." In my health investing I saw hundreds of health companies without a single health expert on the team, and it showed in every product decision. If the gap sits at the heart of the business, it usually ends the conversation.
The questions they ask you out loud
The spoken ones are more predictable: why now, why you, how big is the market from the bottom up, what are the unit economics, how far does this round get you, and what happens at the next round. Every raise also generates two or three questions specific to your company that come up in almost every meeting. Track them from your first calls, write the answers down, and refine them as the round goes on. By meeting ten you should never be hearing a question for the first time.
The unanswerable question
At least one question in every raise has no clean answer. "What if Google builds this?" "Isn't this market too competitive?" The instinct is to open it up for discussion with the investor. With this category, that instinct is wrong. The investor may believe you can never beat Apple, and they know less about your market than you do, so a discussion just gives the doubt more airtime and makes the risk feel bigger.
Stand your ground instead. Answer as the expert, with a counterargument backed by data that leaves little room to argue: the incumbents' last five launches in your space flopped, the market is enormous, you move faster and you hold an insight they do not. Confidence in that moment, built on real evidence, is what investors describe afterwards as the it factor.
How to prepare
Record your practice calls and your live ones, then watch how you handled the hard moments. Every founder I coach builds a running answer bank through the raise, because the two or three killer questions of your round announce themselves early. The unanswerable one takes rehearsal above all: knowing when to discuss, when to explain, and when to push back only comes from reps. It connects to the deeper mechanics of the decision (how investors actually decide to invest).
Want to know which of the eight is most likely to sink you? The diagnostic scores you across 15 questions and shows where investors would say no before they get the chance. Find out why an investor would say no to you. It is free behind an email.
Common questions
What is the most important question investors ask?
The one they ask each other: can I get conviction on the CEO. Everything else on the list can be argued around. That one cannot, which is why fundraising preparation should spend as much time on you as on the deck.
How should I answer "what if Google builds this?"
As the expert, with data, and without opening a debate. Show that the incumbents have ignored or fumbled your market, name your speed and your insight, and close the door politely. Turning it into a discussion makes the risk feel bigger than it is.
Should I admit weaknesses when investors ask?
Yes, paired with what you are doing about them. Investors expect gaps at your stage. What they are testing is whether you see them clearly. Discovered weaknesses hurt far more than disclosed ones, and discovered lies end deals outright.
How many co-founders is too many?
More than three raises the question in most partner meetings, and interchangeable roles raise it faster. Clean roles matter more than the count: a team of four with sharp lanes reads better than three co-CEOs.
Work with me
I coach founders through the whole raise, from building the investor network to closing the round. 120+ founders so far, with $250M+ raised between them. If you're planning a raise in the next six months, here's what working together looks like.
See how the coaching works →