Jack Flintoft

All truth passes through three stages. First, it is ridiculed. Second, it is violently opposed. Third, it is accepted as self-evident — Arthur Schopenhauer

Every founder walks into a pitch certain of something the rest of the world mostly doubts.

Few thought Superhuman (the snazzy new email software) could displace incumbents like Gmail and Outlook. Few believed Musk when he said reusable rockets would radically lower the cost of space travel. Fewer still thought Airbnb could convince people to sleep in strangers’ homes.

In each case, the founder carried a set of premises about how the world works — and how it could change. The investor’s job isn’t to be prescriptive (“this is wrong because X,Y,Z”), but to unpack those premises, assign weight, and see if the conclusion holds. It’s why I find it frustrating when the early-stage startup space gets dismissed as “fluffy” or “non-quantifiable.”

Although I study philosophy now, my hardest — and most formative — philosophy teacher was in high school. She drilled logic into us, building elaborate logic trees to show why philosophers saw the world as they did and held the beliefs they held. Strangely, in early-stage venture, I find myself using that same scaffolding more than ever.

Because in the business of billion dollar moonshots, the biggest outcomes come from being both contrarian and right (the hardest kind of beliefs to hold). If investors just gave money to people tackling consensus ideas we’d probably be missing out on a lot of consumer surplus… It’s about meeting founders whose core beliefs you didn’t think could be true, and then working through whether those beliefs can hold.

Let me show you what that actually looks like in practice.

A founder walks in with a (sometimes implicit, or explicit) logic chain of premises:

Premise 1
Premise 2
Premise X …
Therefore, conclusion

Each premise is an assumption (a belief about the world / people / technology). The job of the Venture Capitalist is to sit in the jumpseat next to the founder, pinpoint the assumptions that matter most, and judge whether the conclusion (that the startup will be wildly successful) can truly stand. It’s an art of understanding.

Take Airbnb in 2009 — running directly against how most people saw the world (this was back when the idea of staying in a stranger’s home felt unsafe and niche. People assumed something like Couchsurfing was fine for a small community, but not something that could scale globally. Boy were they wrong …).

So we can lay out that premise as such (premise 1 below).

Premises / assumptions for AirBnB (obviously a simplified list).

1. People will stay in strangers’ homes if trust can be built.
2. Another important assumption
3. Another important assumption
   Conclusion: Therefore, this can be a generationally successful company
   

Before the meeting, the founder and VC may not see eye-to-eye on the premises — holding the same statements on the table, but assigning very different weights to each one:

Before the meeting:

Premise	Founder weighting	VC weighting
People will stay in strangers’ homes if trust can be built	95%	10%
Premise 2	95%	20%
Premise 3	95%	15%
Conclusion	Yes	No

But after the meeting, the founder may have shifted the VC’s “weighting” of premises / beliefs — or better yet, introduced a new belief the VC hadn’t considered at all (something Eric Vishria at Benchmark describes perfectly here).

After the meeting:

Premise	Founder weighting	VC weighting
People will stay in strangers’ homes if trust can be built	95%	70%
Premise 2	95%	75%
Premise 3	95%	65%
Premise 4 (New!)	70%	70%
Conclusion	Yes	Yes

And this is how I found myself explaining VC to my grandma — who doesn’t use LLMs or even know what they are. The founder’s task is to surface the right premises; the investors task is to test them. If the weights shift far enough, the conclusion changes.

The same pattern plays out outside fundraising — hiring the first engineer, closing the first enterprise deal. The conversation is always the same: here are the premises, here’s why they matter, her’s why you should weight them like I do.

I’d encourage those building to think about your assumptions and how you’d explain them — ideally so that, in hindsight, your radical premises read as self‑evident.

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Note: I’ve obviously neglected in this post to mention much about the founders themselves — which is, of course, a huge part of a company’s success at the early stage — but that’s a separate discussion entirely. Implicit in all this though is that great founders hold strong assumptions about how the world should work and where what they’re building fits within it.