the founder's iceberg
when you talk to me i only see the tip — the pitch, the product, the chart. the real stuff is underwater. my advice is only as good as how much of it you let me see.
When a founder gets on a call with me, I only see the tip. The pitch, the product, the numbers on the deck. That’s maybe the top ten percent. The other ninety — your values, your fears, why you’re really doing this, what’s going on with the team, the money, your life — sits under the waterline, and I can’t see any of it unless you show me.
My advice is only as good as how much of that iceberg you show me. Advice built on the tip is advice for someone else’s startup.
Here’s why the tip fails you. I can convince anyone you’re the next Facebook. If the pitch is all I ever see, that’s exactly what I’ll do — tell you it’s great and send you off. Now you’ve made your best advisor useless, because I’m steering a company that doesn’t exist. Within thirty to sixty minutes I can usually see where a founder is going to fail, but only if the real thing is on the table.
The real thing is almost always underwater. A founder came on a call — great background, security at DocuSign, Coinbase, Uniswap. Somewhere in minute four he mentioned he was retired, living in Japan, and had built this for fun. That was the end of the call for me. The product was fine. He’d just told me what happens when it gets hard. That one line was the whole evaluation, and it was hidden until it slipped out.
The numbers hide things the same way. A founder told me he had 44,000 users. It can never be a round number — did you read that off a dashboard, or did someone tell you? He’d been told. If you bring me the tip and you haven’t looked under it yourself, we’re both advising a company that isn’t there.
So what am I actually fishing for. One question, under all the others: what is the problem you will not leave when it gets hard. Not your idea, not your TAM, I already know those. The chart tells me if the hockey stick is forming. It doesn’t tell me whether you’d still be working on this in 2031 if no one ever funded you. That answer lives below the waterline, next to the chip on your shoulder and the thing you’re still angry about. I got rejected by every Mumbai VC in 2012 for not being from an IIT, and I lost everything in meme coins in 2018. Both were fuel. I can’t point you at yours if you hide it.
What to bring to a call: the real thing. Please don’t try to impress me. I’m in the boat with you — if something’s broken, say so, because I can’t help you steer if I can’t see the water. Bring your real numbers, not the deck’s: who pays, whether it’s recurring, how many came back last week. If you don’t know your valuation yet, just say we’re early. That’s fine. And bring the questions two levels under the one you think you’re asking, because the problem is usually three levels below where you start.
the call where i said it best
A cofounder kept telling me the growth plan was going to work. I said please don’t try to impress us, we already invested, so did your lead, nobody’s going anywhere. Just tell us the real thing. The honest answer to “will we be profitable in two months” was no — and the honest answer is the one that got them the right round. The moment he stopped showing me the tip, I could actually help.
do this this week
Before your next call with anyone whose advice you want, write down the one thing about your company you’re hoping they won’t ask about. Lead with that.
the line to remember
my advice is only as good as how much of the iceberg you show me. advice built on the tip is advice for someone else’s startup.