A few times, I've talked to an executive manager or early-stage investor, and this happened:

me: Here's the main plan. Now, we think the odds are good, but the most likely failure point is here. If necessary, we have an alternative plan for that part, which goes as follows...

them: (visible disgust)

I was so confused! Aren't contingency plans good to have? Sure, investors want to see confidence, but what they really want is confidence in the overall vision. They expect some things to go wrong along the way, maybe even requiring "pivoting" to a different product.

Well, I've gotten more experience since then, and thought about things more, and I think I understand the thought process now.

Imagine you're watching Star Wars, and the rebels are getting ready to destroy the Death Star. The guy planning the operation says:

OK, the primary plan is a torpedo to this exhaust port. You've all been briefed on it. But there are some key risks: the shielding could've been upgraded, it might be too heavily defended, and torpedo targeting could fail. As such, we've designated secondary targets here and here which should at least disable the Death Star for a while. The tertiary plan is a fallback meant for retreat with a minimum number of casualties, which I'll go over now.

How does that make you feel about the chances of the rebels destroying the Death Star? Do you think that the competent planning being displayed is a good sign? According to movie logic, it's a really bad sign.

Once, a guy (who's currently a founder of an AI-related startup in Silicon Valley) introduced me to this VC for a call to talk about investment in a new battery chemistry. Part of the conversation went like:

me: I want to talk about the technology and issues with alternatives, but it seems like nobody wants to discuss that part.

VC: It's just not that important to investing.

me: I see all these failures that happen that could've been easily avoided with competent technical due diligence. Softbank lost a lot of money on WeWork, wasn't that worth avoiding?

VC: No, Softbank has their approach and it works. People make fun of WeWork but Softbank has actually done really well overall.

Well, a few years later, it seems like maybe the approach used by Softbank's Vision Fund has some problems after all...? Anyway, about investment in that battery chemistry:

VC: So what's your growth story?

me: Uh, raise some money, validate the technology to the satisfaction of investors, raise more money, demonstrate a production line, and then either get enough investment to do large-scale production or sell to, say, a large auto company.

VC: That sucks. Some advice for you: never talk about selling to a big company to a VC, at least not before it's actually an option. And you should avoid saying your plan is to "raise more money" too, investors want to hear about what impressive stuff you can do with just the money they can provide.

me: Well, from my perspective this is...less far from commercial practicality than what QuantumScape has, and they're worth a billion dollars already.

VC: You should look at SaaS startups. As a VC, it's hard to justify investing in physical stuff when the growth stories those normally have are much better.

me: I see. Some of my friends have some other stuff they developed, so maybe you'd like one of their "growth stories" better. Is there something in particular you're interested in?

VC: As I said, it's not really about the specific technology. I tend to invest in SaaS startups, but it's not because they're SaaS per se.

What I eventually realized was that I wasn't taking that word "story" literally enough.

Looking at the web pages of startups, I'd often see these descriptions of the founders that are like...descriptions of a five-man band in a TV show pitch, succinctly establishing backgrounds and personality traits that you might find on TvTropes. Eventually, I saw enough of them that I realized that there was something driving that format. And eventually, I realized that investors were actually making decisions based on that sort of thing.

When a customer at a bazaar haggles with a street vendor, they aren't breaking out statistics and math. That kind of haggling is more of a duel of stories, with each side proposing a story about the item's value, and the stronger story getting its number weighted more heavily.

With investment and hiring, there are people who want to see character archetypes they have in their head like "fresh MIT graduate" or "ex-googler" or "ex-SpaceX" or "Harvard grad MBA" or "former Fortune 500 executive director". But actual people aren't character archetypes, and the more interesting and capable people are, the less they're well-represented by tropes.

Similarly, investors seem to want a concept pitched to them that appeals on a narrative level. It's not "consider this techno-economic analysis that's been done, and then we should adjust for X and Y". It's more like...

"we're going to do AI stuff, but we'll sell tools to the AI startups" to an investor who likes AI and often heard a story about selling shovels to gold rush miners
"we're going to pull CO2 out of the atmosphere and use it to make valuable products" to an investor who feel that the course of technological progress should naturally lead to global warming being solved, so logically something like that must be viable
"we're going to do nuclear power but with a Silicon Valley attitude" to someone frequently exposed to memes about "nuclear power rightfully being super cheap" who also likes Silicon Valley
"we're going to do manufacturing IN SPACE" to an investor who thinks "space is the future"
a concept that follows (some rule about which option to take) that's common advice that coexists with the opposite advice, that the investor believes in really hard because it worked for them in the past and they want to believe they know something other people don't and weren't just lucky

So, if you're working on a pitch to investors or executives, perhaps what's most important is understanding what kind of stories they like - real stories, fictional stories, and fake stories they believe are real. Look at bios of founders of their last few investments (as presented on company websites) and see if they follow a pattern. Look at the main characters of the movies they like. Look at their retweets and see what stupid memes they fall for. And so on.