If you are raising in 2026, you donāt need more pitch-deck tips. You need to understand what the person across the table is actually weighing up while you talk.
Chris Tottman has watched thousands of pitches. He is founding GP at Notion.vc, has backed more than 500 founders, and still spends his time in the weeds of early-stage B2B. He also writes The Foundersā Corner newsletter, which many SaaS operators treat as a manual rather than content.
I sent him a simple brief: explain how you really judge founders. What came back was a field guide for anyone trying to raise money in a harder market.
Here is how he thinks:šš»
1ļøā£ Start with pain, not theory
Chris listens for pain before anything else.
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 a clear picture of the broken process. Who is stressed, where time leaks away. Which spreadsheets, emails and manual steps create the mess.
A founder once walked him through the legal spend chaos inside a CFOās inbox. Every stakeholder, handoff, and delay. It felt lived, not guessed.
That level of description separates a real problem from a nice-to-have. If you canāt paint that picture, he assumes you havenāt been close enough to the buyerās world.
Takeaway for 2026: go into a fundraise with a āpain mapā. Walk an investor through the day in the life of your buyer. Show the friction, not just the category.
2ļøā£ Show your homework on the āpainful kernelā
A phrase Chris uses a lot is the āpainful kernelā. The thing that actually hurts, under all the surface talk about efficiency or AI.
Founders who have it talk in stories from customer calls, support chats and long days sitting next to users. They have done what he calls a āPain Visualisationā: mapped every step, every decision, every place where the process fails.
He pays attention to how they gathered that knowledge. Have they interviewed buyers, shadowed teams, or sat with support logs for weeks. Or are they repeating second-hand opinions.
This is where most pitches fall apart. Big claims about total addressable markets, thin insight into one real user.
Takeaway for 2026: turn vague pain into a concrete sequence. Bring that into the room. It shows work ethic, empathy and focus, all in one go.
3ļøā£ Stop chasing ābetterā; build different
Youāve probably seen Chris quote this line: āthe best founders solve unique problems.ā
It links to another phrase he uses a lot: āDonāt be better, be different.ā
Being slightly faster or slightly cheaper is rarely enough now. He looks for a different workflow, a fresh way to package or sell, or a corner of the market incumbents ignore. Sometimes it is pricing, sometimes it is channel. Sometimes it is how the whole product is framed.
Founders who stand out can explain that angle in a sentence. They know which belief they are challenging, and why that matters for the buyer.
If he has heard the same angle three times that month, the bar moves higher.
Takeaway for 2026: write down, in one clear line, what makes your approach different. If it sounds like everyone else, you still have work to do.
4ļøā£ Solo is fine. Isolation is not.
Chris does back solo founders. He just wants proof they are not building alone in their heads.
He asks simple questions. āWho challenges you? Where do you get your feedback?ā Then he watches how specific the answers are.
Strong solo founders talk about early hires they have already attracted, operators they WhatsApp for blunt feedback, and customers who act like partners. Weak answers sound like āI talk to lots of peopleā with no names, no real tension.
He is also open about his own dyslexia and is drawn to people who have had to work around something. That might be background, education, or a previous failure. What matters is the self-awareness that comes with it. āHereās what Iām not good at and hereās how Iāve built around thatā is a green flag.
Takeaway for 2026: bring your circle into the story. Show who keeps you honest, and how you have designed around your gaps.
5ļøā£ Obsession shows up in customer detail
On founder-led sales, Chris is blunt. If you canāt talk about your customer in depth, the rest of the pitch doesnāt matter.
He starts with āWhen did you last speak to a customer?ā Then he digs. Can you quote what they said. Do you know how they buy, who signs off, where deals stall, and which emotion drives urgency.
The best founders can walk through 30 conversations without notes. They know where deals fall apart inside the buyerās company. They know the awkward objections and the objections that are just smoke.
This is how he tests ācustomer obsession,ā with detail that only comes from long hours on calls.
Takeaway for 2026: treat customer conversations as your main preparation for fundraising. Go in ready to talk through them as if the investor was your new sales hire.
6ļøā£ Clarity beats hype in this market
The last few years filled VC with hype cycles. AI, SaaS before that, something else next. Chris isnāt blind to that, but he keeps coming back to one word. āClarity.ā
He likes founders who can operate in what he calls āhard modeā: messy markets, long sales cycles, or unfashionable sectors. They stay close to value, move quickly, and avoid chasing every new trend.
Presentation style matters less than people think. Many of the founders who stuck with him did not walk in with a loud presence. They came back a second time with more evidence, tighter thinking and better customer stories. That persistence changed his mind.
Takeaway for 2026: donāt over-rotate on performance. Sort your thinking instead. Be precise about the problem, the buyer, the workflow and the wedge youāve found.
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 also recently released 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 a practical manual for anyone trying to raise, scale, or regain clarity during chaotic phases of a company.
For now, if you are raising this year, read this back before you send the next deck. Map the pain. Do the homework. Show your circle. Bring your customer with you into the room.
That is the level investors like Chris are working at.