33 Comments

Just want to say thank you for the Hard Work™ you put into your writing. Your style is hilarious and makes me laugh every time.

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Thanks! I appreciate that. I do it all so that, one day, this blog can also be worth one trillion dollars.

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I'll try to articulate this as best I can. There's a sense of honor and prestige for doing things the hard way. If someone internalized this advice of "startups are hard, don't make a startup", then they simply don't do it. Yet, there is a subconscious measuring stick that tells us the ones who do make a company are somehow better humans. But if you are the ones that see and understand the immensely hard work before ever attempting it, doesn't that make you the smart ones?

So if it's not about realistically predicting the level of work, then it's about prestige or money or whatever. And by that (very shoddy) logic, smart in some ways != money and prestige.

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I'm not sure I entirely follow? Is the idea that the "smart" decision is to not start a company (because it's hard, etc), but the "prestigious" decision (either because it demonstrates your fortitude or because it might make you rich) is to start a company? And if that's true, they might not actually be *surprised* by the work; they're actually just choosing it because they want the prestige?

If that's the point, I think I sorta agree? I definitely think a lot of people choose to start companies because they're chasing the prestige. But I also think a lot of those people are genuinely surprised by the work. Though I think it might be for the reason you're saying - when you're in it for the prestige, you're in it for the brand and the outcome, not the actual job. And that makes the job feel like all the more intense.

Someone made a kinda similar point about athletes, that athletes choose to play a sport first, and then realize they could be rich and famous from that sport after playing it for a long time. A lot of founders do it in reverse. They choose they want to be rich and famous, and then go looking for a sport to play.

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Yes, I struggled to make that coherent. But you're right. If you chase prestige, it doesn't make you smart enough to realize "holy sh*t this is a lot of work (and it might not be worth it)". But maybe the people who can realistically assess a workload before they even start, and determine it don't be worth it, are onto something more than they are given credit for.

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I do think there's a bit of an in between there, where you can still do it but not go full VC where you raise tons of money, try to go straight to the moon, etc. But I've never done that, so I might think that it's the best of both worlds but is actually the worst of both worlds.

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You had me at "dealing with Trinet, helping employees deal with Trinet"

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What is Trinet?

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It's a company that administers things like benefits and payroll that a lot of early stage startups use. It's generally pretty useful because that stuff is tough for a ten-person company to manage, but nobody's ever not frustrated with their health insurance provider in some way.

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You pose excellent follow up question to Jensen! I wonder if it is a Jensen nod to survivorship bias. A more complete picture would include some discussion from the Acquired podcast guys on who failed and why.

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Yeah, someone on Twitter made a similar-ish point, about how successful people either struggle to see or don't want to brag about the things they're *good* at to be successful. https://twitter.com/ChristianNolan/status/1720484984295760275

I do wish they pushed him a little more on this on the podcast though. It seems like there's a lot of interesting things to dig into there (which, maybe he wouldn't have much to say about), and they didn't really push on it much.

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Benn, Guess what? Andrew Ross Sorkin just asked Jensen this specific question from this exact podcast AND, Jensen answers it. Start from like 22.40 min mark. Cheers, my friend!

https://youtu.be/Pkj-BLHs6dE?si=-oK8XSdsskHQKr_A

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1. Oh amazing, nice find, and thank you for sharing!

2. But also, what a weird and kind of incoherent hedge? "I'm not saying it's not worth it; I'm saying that if I knew how much work it was going to be, I wouldn't have done it." Isn't that same thing as saying you're saying it's not worth it? Is he saying his *former* self would've had said it was worth it, which means his former self would've misjudged how much he values the success? Or is he saying he wouldn't have done it if he knew how much work it was, *without* knowing it how big of success it was going to be? In which case, like, obviously?

I STILL HAVE FOLLOW-UPS JENSEN.

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Yeah, I totally follow you Benn. And if we put our tinfoil hats on, is Jensen trying to discourage competition in his areas of mastery. "Gosh it is just sooo hard. Don't do it. It is just wayy easier and simpler for YOU to just buy from me/Jensen."

Seriously, I think the comment is an unforced error from Jensen. Either give us a salesy positive answer, or don't answer it at all. But, what he says doesn't marry with American Optimism/Tech Innovation that he built his life on.

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Yeah, there is a little bit of that. I don't know if it's explicitly trying to pull the ladder up from behind him, but it's kind of strange to say, "Of course I'm happy with my choices, but you should make different choices." It seems like trying to walk to tight of a line, both acknowledging how hard it is, but still being an optimistic and grateful and all of that.

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Loved this article - especially relevant as tech startups are exiting a period of “free money” and facing a much harder path to an exit or additional funding round. Time to do the work!

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Thanks!

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Read this first on Every.to. So well thought out, Benn., I had to come read it again here and follow your work, of course. I like the idea of working hard to square up to who you will eventually square up to. Because eventually, buyers won't make decisions based only on the gimmicks or slight difference a new startup offers.

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Thanks! I really appreciate that, and am glad you liked it.

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Read your post on Every and wanted to come comment on the original -- thanks for writing it. :)

I totally agree that building a great business isn't a gimmick and that it's a surprisingly enormous amount of work, but I don't agree with the end conclusion. I think the idea that you should "go through the front door" and compete by building the best version of the product is wrong. What does the "best" even mean if you're not specifying "for whom"? And if the answer is "everyone", isn't it just going to be an all out war? As Michael Porter would say, "Competing to be the best leads to convergence on the same commodified offerings; eroded profits due to continuous one-upmanship; reduced choice for customers; and stifled innovation."

Ultimately, I think you have to run the playbook you describe: "we’ll start with a freemium product in some vertical they’re missing, build a community of enthusiasts..." and take it all the way to "win a slice of the market and expand from there."

I think the examples you cite did exactly that. Figma had to choose a target user and champion their needs. They were not tackling Illustrator's market head on. Even though they just aimed at taking a slice of a growing market, it required that they 1) build a LOT of really complex, boring, core feature stuff that doesn't seem differentiated and 2) also build stuff that product designers really want that is new and cool (e.g. multiplayer). And instead of expanding to Illustrator's exact market, it seems apparent to me that Figma's strategy is to go after devs, PMs, and other parts of the "development triad" instead of trying to go after, say, illustrators.

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Thanks, glad you liked it.

And eeeh, I think I'd interpret that story differently. I agree you can't build the huge product on day 1, and agree that the examples didn't try to do that. But where I interpret it differently is that they all appeared to recognize that they would need to do that eventually. Figma knew that for Figma to become what Figma became, it would take on Illustrator directly. They didn't see themselves as creating some new category, or claim that they would beat Adobe by cleverly dodging them.

My view is that a lot of startups do that dance, and tell themselves they can become a huge company without ever really taking on the huge company directly because it lets you hide the work that you have to do. You can imagine yourself reaching the mountaintop by outsmarting the mountain, rather than climbing it. And I think that's what separates the companies that do this right versus those that don't. It's not necessarily that they plan on taking the exact same route up the mountain as the people who are already at the top; it's that they understand exactly what mountain they have to climb.

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Yep

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I’m curious about the experience of founders based on their previous role prior to founding. If you are managing yourself (no boss) leading and managing others, raising money, building a product, doing sales and marketing, all at once all for the first time of course that’s insanely hard. I’m picturing a straight out of college founder. However if you have trained for founding by doing various diverse roles and have atleast some experience leading / managing seems like that would make it a little easier for most people. Of course it also matters a lot who you are around. Are you around other founders that complain all the time about how hard things are? Founding will be harder for you too. Same with hiring the wrong people, etc.

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I say this but I’m reading that Jensen Huang did pretty much exactly what I said above with the diverse roles and management experience at LSI Logic prior to founding Nvidia. So.. ya... 🤷

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For me (and I can only speak to my experience which is basically a founder right out of college; I'd been working for ~4 years, but was a cog with no real responsibility), the most surprising thing was that you'll feel like every problem is your problem. If there's a bug in the product; if the lead pipeline is slow; if two employees didn't get along; if you're not shipping fast enough; if people are confused about product direction; etc etc etc - you can't fix those things yourself, but the buck ultimately stops with you if they're not fixed.

I could see that being something you're used to if you've run a big org before, though even that feels like it might be a little different. If you join a company as an exec, the buck also stops with you for a lot of things. So that's similar. But the difference is that you're an outsider of sorts, and that you can separate yourself from existing problems to some degree - "it was like that when I got here." If you're there from the beginning, and have been in charge from the beginning, you don't just own fixing all the problems, you also kinda are responsible for all of them? That's not literally true, but it was part of the mental dynamic that I always found particularly heavy.

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Ya - I have observed that pattern with the outsider executive vs founder executive. Along a similar line of thinking part of the key to success from my observations appears to be 1) taking responsibility while acknowledging your lack of control 2) a genuine faith that things are going to work out - even when you truly don’t know how.

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I have mixed feelings about the second one. I think that's true, but that's also, like, SBF? It's like this indiana jones clip - you have to blindly believe to make it. But also, a lot of time there's just no bridge and doesn't go so hot.

https://www.youtube.com/watch?v=sBBbq2g7yf8&t=5s

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Classic Indy clip!

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Ya maybe a genuine faith tethered to reality where you have at least some evidence it’s going to workout long term but not all the details in the moment.

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my favorite thing about BeReal was when LinkedIn news started handwringing about how it would never make money. I hope they never try to make money. I hope it's a fun little side project for them that's always this shitty little app that takes forever to take pics and posts them in a really lackluster feed. it's so fun. i also wish for rainbows and unicorns and no one to have to work for a living :angel_face_emoji:

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This is probably a very late-capitalism GenZer thing to say, but that's one of the big bummers about Silicon Valley to me. There are so many good things that could be really good small businesses that make good and steady money. But that's never enough; they all gotta be huge.

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it gets kinda MLM'y huh. Everything has infinite growth potential! And if your idea isn't gonna be huge it's not worth doing!! It is a bummer and it's giving Herbalife Huns telling you your income has uncapped potential a bit.

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If you can't go infinite (https://www.amazon.com/Going-Infinite-Rise-Fall-Tycoon/dp/1324074337) (or go to jail forever trying), why bother?

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