If you are raising in 2026, you donāt need more pitch deck tips. You need to understand what the investor across the table is actually judging while you talk.
Chris Tottman has watched thousands of pitches. Heās founding GP at Notion.vc, has backed hundreds of founders, and spends his time close to the reality of early-stage B2B.
I asked him to explain how he really judges founders. What came back was a much clearer picture of what investors like him are actually listening for.
Hereās how he thinks: šš»
1ļøā£ Start with pain
āIt always starts with the pain,ā he told me. When a founder can say āmy buyer is losing sleep becauseā¦ā and back that up with detail, he leans in.
He wants to know what keeps going wrong for the buyer and why they are still putting up with it. The pitch gets much stronger when a founder can walk him through the mess rather than just naming the market.
One founder talked him through the legal spend chaos inside a CFOās inbox. Chris could see the delays, the handoffs, and how quickly more people got pulled into the problem. It sounded first-hand.
That is usually the difference between a real problem and a nice-to-have. If you cannot paint that picture, he assumes you have not been close enough to the buyerās world.
Go into a fundraise able to walk an investor through a day in your buyerās life. Show them where the friction actually sits.
2ļøā£ The āpainful kernelā
Chris uses the phrase āpainful kernelā a lot. It is the part that really hurts underneath all the talk about efficiency, automation, or AI.
He is listening for whether you have isolated that pain properly or just wrapped a broad market story around it. To stand out, you need to get specific about what keeps breaking and why the buyer still puts up with it.
He pays close attention to how that understanding was built. Have you interviewed buyers, shadowed teams, or sat with support logs for weeks? Or are you repeating second-hand opinions?
This is where a lot of pitches start to wobble. Big claims about the market, not much understanding of one real user.
Make that painful kernel concrete enough that an investor can see exactly where the pain sits and why it matters.
3ļøā£ Better is not enough
Chris comes back to this a lot: the best founders solve unique problems. It connects to another line he uses often: āDonāt be better, be different.ā
A bit faster or a bit cheaper is rarely enough now. He is looking for a different workflow, a different way to package or sell, or a corner of the market incumbents keep missing.
That difference might sit in pricing, in distribution, or simply in how the whole thing is framed.
You need to be able to explain that difference in a sentence. Which belief are you pushing against, and why does it matter for the buyer?
If Chris has heard the same angle three times that month, the bar moves.
Write down, in one line, what makes your approach different. If it sounds like everyone else in the market, you are not there yet.
4ļøā£ Solo is not the problem
Chris does back solo founders. He just wants proof they are not building everything in their own head.
He asks simple questions. Who challenges you? Where do you get feedback? Then he listens for how real the answer sounds.
The strongest solo founders can point to real people around them: early hires they have already pulled in, operators they message for blunt feedback, and customers who push back like partners. The weak answers sound vague: lots of people, no names.
He is also open about his own dyslexia and pays attention to founders who have had to build around something.
What matters is whether they understand their own limits and have done something about them. āHere is what I am not good at, and here is how I have built around itā is a green flag.
Bring your circle into the story. Show who keeps you honest and how you have built around the parts of the job that do not come naturally.
5ļøā£ Obsession sounds specific
Chris is blunt about founder-led sales. If you canāt talk about your customer in depth, the rest of the pitch doesnāt matter.
He starts with one question: when did you last speak to a customer? Then he keeps going. Can you quote what they said? Do you know how they buy, who signs off, where deals stall, and what actually creates urgency?
The founders who impress him can walk through 30 conversations without notes. They can explain where deals begin to slip inside the buyerās company, which objections are real, and which ones are just smoke.
He is testing whether you have really been doing the selling. The detail tells him that faster than any claim about customer obsession ever will.
Treat customer conversations as your real fundraising prep. Go in ready to talk through them as if the investor were your next sales hire.
6ļøā£ Clarity beats hype
The last few years have filled venture with hype cycles. AI now, SaaS before that, something else next. Chris sees all of it, but he keeps coming back to one word: clarity.
He likes founders who can operate in what he calls hard mode. That might mean a messy market, a long sales cycle, or a sector nobody is excited about. He still wants to see that they stay close to value and keep moving.
Presentation style matters less than people think. A lot of the founders who stayed with him were not loud in the room. They came back the second time with more evidence and a clearer sense of the customer. That changed his mind.
Do not over-rotate on performance. Sort your thinking out first. Be clear on the problem, the buyer, and why your wedge matters.
If you are raising this year, read this again before you send the next deck.
Go back to the pain, get closer to the customer, and make sure the pitch is backed by work you have actually done.
That is the bar investors like Chris are setting.
If you want more of Chrisās thinking, his newsletter The Foundersā Corner and his GTM Handbook go deeper on this stuff. Treat them like reference manuals rather than content.
Chris Tottman has a new book, The Big Book of Brain Dumps, built from the ideas that shaped his career and the lessons drawn from backing more than 500 founders. Itās for anyone trying to raise, scale, or make better decisions when things get messy.
Two more reads before your next investor pitch
