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Succeeding in the startup world reminds me of the funfair analogy:

The rich kid will have a go at throwing the dart at the balloon, and miss. But, because they're a rich kid, they just take out their wallet (or parents' wallet), get more stubs, and try again (and again) until they hit the balloon.

The middle class kid will have a go at throwing the dart at the balloon, and also miss. Then they will walk away, saying that was fun, and go hang out with their mates. But maybe the 10th or the 100th middle class kid will hit the balloon.

And the working class kids? They work at the funfair. They never get to throw darts.

Here's the kicker: those kids who hit the balloons? One or two of them might go off and start a blog/podcast, or write a book titled

- Zero To Plushy

- The Dart Thing About Dart Things: Plushy Hunting When There Are No Easy Answers

- Dart Throwers at Work: Stories of Plushy Hunters' Early Days

- You Are a Badass at Hunting Plushies: Master the Mindset of Throwing Darts

- The Lean Plushy Hunter

- &c

Hell, if it's the middle class kid writing the book, they might even throw a couple of anecdotes in there about how they didn't have an easy start (compared to the rich kid), and it might even be true for them.

That book is the catnip that folks like you and me base our life decisions on.

I had a go at 3 startups, only one of them quasi-full-time, as I self-funded with freelancing. (I spent years building a "turn PDFs into data" product, had a few paying customers, and then one day got made totally redundant by Google Vision.)

Needless to say, I got completely burned out on startup number 3.

I shuttered the business just as Covid hit. I spend more time with the family (wife, two daughters, 9 and 6), and we moved to the countryside to be closer to ageing parents and siblings with kids.

It's healing time, baby

I wish you all the best



> The rich kid will have a go at throwing the dart at the balloon, and miss. But, because they're a rich kid, they just take out their wallet (or parents' wallet), get more stubs, and try again (and again) until they hit the balloon

I get contacted for a lot of “rich kid” startups for consulting work. This notion that rich kids are succeeding at startups due to their perseverance and fallback options is almost the opposite of what I see in the real world. A lot of the “rich kid” startup founders I’ve followed or tried to work with have been only half committed to actual working on their startups. They often want to be the idea guy or the money/fundraiser person or the iconic CEO role holder, but when it comes time to do the work they’re not interested in grinding.

Those fallback options also become a liability when things get difficult or stop being fun. A lot of them dip out at the first signs of struggle and fall back to easy jobs in their parents’ network.

In theory they should have more runway to persevere at a startup. In practice, they often have too many easy options to fall back on to actually persevere at the execution required.


This makes intuitive sense to me. Startups are so hard that I know I wouldn’t persevere if I was sufficiently wealthy already. I’ve been failing at this game for twenty years straight. Like the OP, I quit last year and got a full time job again. But it always beckons me back somehow. It’s the failed startup attempts, the failed investments, the fraudsters who conned me out of my money, the career that could have been spectacular, but only ended up so-so because I’m not in the US. Somehow every knockdown from life makes me a little grittier, a little more determined when I get back up. How does a rich kid develop that?


Anon for the obvious reasons... I was involved in such a start-up. Two of the founders were smart, Ivy-educated, surprisingly well-connected for their youth, and lazy. Once there was funding and a professional team around them to grind out all the details and versions of the product and get it marketed and sold, you know, the hard stuff after the investor demos, they didn't want it anymore. One fucked off to party and couch-surf in warm vacation spots, the other meandered in and out before being shown the door by the board. I ran into one of them years later and they're both still kind of bouncing around doing influencer-things, writing, and being hustle advisors.


> I get contacted for a lot of “rich kid” startups for consulting work.

Aren't you proving the OP's point? The point was, precisely, that they have options, not that they "persevere". Contracting consulting work is one such option.

Poor people cannot contract anyone to help them.


I think he’s kind of making a case that the rich kids aren’t always the ones that succeed ultimately in startups because they leave at first sight of trouble.


I was curious what books you were making a play on words for (since it wasn't immediately obvious), so asking ChatGPT:

    What are the real names of the books? For instance, "Zero To Plushy" is play on "Zero To One". List out the names for the other books.


    "The Dart Thing About Dart Things: Plushy Hunting When There Are No Easy Answers" is a play on "The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers"
    "Dart Throwers at Work: Stories of Plushy Hunters' Early Days" is a play on "Grit: The Power of Passion and Perseverance"
    "You Are a Badass at Hunting Plushies: Master the Mindset of Throwing Darts" is a play on "You Are a Badass: How to Stop Doubting Your Greatness and Start Living an Awesome Life"
    "The Lean Plushy Hunter" is a play on "The Lean Startup: How Constant Innovation Creates Radically Successful Businesses"


> "Dart Throwers at Work: Stories of Plushy Hunters' Early Days" is a play on "Grit: The Power of Passion and Perseverance"

It missed this one, it's likely Founders at Work.

> "The Lean Plushy Hunter" is a play on "The Lean Startup: How Constant Innovation Creates Radically Successful Businesses"

Might be The Lean CEO instead.

I had to Google to get the right answers, I wasn't familiar with either book.


This seems objectively false given that the majority of extremely successful startups are founded by first or second generation immigrants, who are often not well off.

https://nfap.com/wp-content/uploads/2022/07/2022-BILLION-DOL...


It's always hard to figure out what exactly to look at...

I find both things plausible, both that the most successful startups are not started by the "rich kids" and that the "rich kids" start most successful startups.

The paper you linked is talking only about the first thing, by limiting its analysis to startups that surpass a $1B valuation. But you could choose some much more modest definition of "successful startup", like "all startups that reach series C or have an exit that returns at least 1.5x", and see totally different results.


Public charge rules mean immigration to the US takes privilege.


Yes, money maters.

Rich kids can conjure tens to hundreds of thousands of dollars from "friends and family" in a mater of days. Hours even, if they're really connected.

They can then pump all that money straight into advertisement, barely even need a working demo - just something that looks like a product. They can do this many times over.

If you're gonna bootstrap something with $0, then you need to win the algorithmic lottery, simple as that. And even if you have some life savings laying around, you only have one go at burning those - though most working class folks in their early 20s rarely have the substantial funds needed to promote a product.


The pyramid of loserdom goes all the way down, unless you're Elon Musk there is someone richer, and there's always someone poorer. Winners figure out how to make it with what they have. Losers always blame lack of resources, look at people who win the lottery, most return to the same standard of living within a few years.

Almost anyone can afford $5 a day in ads to test market.


This is the "temporarily embarrassed millionaire" myth that the whole illusion is based on. Thanks for nothing for propagating it one more time.


would you be able to get meaningful tests for $5 though? i think most ad providers need more as a minimum


I fully agree with your message but some of the joke examples are misguided in my opinion :) Some of those you're making puns with (like Coders at Work) are not about startups or recipes for success, but interviews with early practitioners, and have historical value, much like interviewing scientists.

I also think that software engineering and methodology/best practices book fall in another category. What you want to mock is the startup success stories, "X successful habits of Y people", "How I built X in my kitchen and you can do it too" sort of stuff.


There is also a Founders at work. The funny at work title may have been a riff on that.


So…you’re a rich kid?


Heh, it's been a tumultuous ride for my family.

Paternal grandad was a civil servant, and they were comfortable, but grandad died when dad was 6. Granny married a drunk and lost everything. Step-grandad beat them. My dad grew up a rebel. His saving grace was a teacher who said: I don't care if you don't come back to school, but promise me one thing: you'll read a book a week.

Mum and dad meet quite young, and have me when mum was still a teen. We're dirt poor, and they borrow a lot of money from maternal grandad, who is a gold miner with 7 kids. He gets my dad a job at the mine. The 80s in South Africa were boom years for gold, and everyone does well. My dad pays maternal grandad back all their debts, and I distinctly remember how our lives changed as a young chap. Not rich by any stretch, but we're not hungry or shoddily dressed. My dad is smart enough to spend money on important things, like getting us a home PC, and paying for skills, like my Karate and scuba diving.

However, in my late teens, things start changing again. Jobs dry up for dad, mum leaves him, he falls into depression. Finances rise and fall as dad gets back into work, and makes a bit of money day trading. I drop out of uni, as we can't pay for it anymore.

He meets a nice new lady, who inherited a piece of land, and they scrape just about enough money and know-how together to start developing the first phase of a four-phase development. But, he gets fucked by the bank.

https://en.wikipedia.org/wiki/Absa_Group_Limited#Mortgage_lo...

Three weeks after my wedding in 2014, he commits suicide. Either severely depressed, or so that the bank can't come after him. He leaves whatever they have left in a secure estate to the grandchildren, and stepmum can live in the house until she dies. The kids (me and sis, and 3 step sisters) inherit nothing.

Me? I was privileged enough to learn programming in school. The gold mines funded the schools well, and in 1990 already (when I was 11/12), our classroom had 20 Commodores in it. That was my saving grace: coding. I could earn good money, and self-fund most of my bad decisions.

(My first startup: we won Startup weekend, then got a £50K grant from Telefonica - all pure luck, and a little bit of tapping into the zeitgeist at the time: polling apps)


> That book is the catnip that folks like you and me base our life decisions on.

For sure, this was me in college and grad school. Little in the way of real-life experience, so I borrowed liberally from these business books, the details of which are often simplified or omitted for the sake of the narrative. Unfortunately in life, it is those omitted details that make up the pain of taking risks.


That’s a great analogy. It feels to me like we’re consuming so much “zero to plushy” content these days, and in very parasocial ways. Podcasts, talk shows, documentaries, YouTubers. We’re told over and over implicitly or explicitly that we can be successful like them.

The reality is, statistically most people will die in obscurity, and at some point we need to come to terms with that.

I know I’m just describing survivorship bias and we all know this already, but it feels especially prevalent in the last few years.


How about I'm Go - You're Go. Has any startup founder ever written a book about the mental health aspects of a startup?


While it is true that entrepreneurship is indeed an upper middle class game, you tell only half the story. I've met guys who went from poor to cushy big tech jobs and even then they are deathly afraid of risk. Probably some form of PTSD from their poor days makes them never want to risk going back


I don't think this way of looking at it is helpful either.

Sometimes the rich kid was abused by his dad and it ate him up inside and he turned to drugs and died of an overdose at 25 years old.

Sometimes the middle class kid came from a father that survived as a child in WW2 with undiagnosed metal scars to prove it.

Sometimes the poor kid learns plumbing from his dad then starts and scales a business up to millions in sales.

We don't live in North Korea. A great deal of your future in a country in the west is based on how hard you try and, yes, some intangibles that are beyond your control, but it's no where close to "the rich kid kept buying darts until he won while one in fifty middle class kids actually made it."

Furthermore, entrepreneurship is just one of many hard games. And yes, the rich have an advantage at this specific game and less so because of their access to money and more so their access to their parents that are often successful at navigating society for capital formation. But the rewards of being a successful founder are pretty limited. Slightly better tasting wine. Larger hotel rooms. Softer sheets.

When you actually add up all the real benefits of winning at forming a company, you'll find that they pale in comparison to other games, many of which are easier, but some of which are harder or MUCH harder.

People today barely remember who Rockefeller is. He's the name a fancy building near the middle of the city to most people. That will be Bill Gates. That will be Steve Jobs. That will be so many of our supposed HN heros. If humanity makes it a couple hundred years, more people will remember Putin and Biden. Their games are harder. They ultimately matter more. And if legacy is more important than threadcounts then their rewards are much larger.

I think it is more important to find out what is true and what is false and to embrace the truth and help others than it is to win at business. And if it matters at all to you, I've founded a couple of failed companies and one that was acquired and I still think tech entrepreneurship can be a good thing, but only to a point.


Judging by your website, you're very much the rich kid who simply resents the label.


“Sometimes the rich kid was abused by his dad and it ate him up inside and he turned to drugs and died of an overdose at 25 years old. Sometimes the middle class kid came from a father that survived as a child in WW2 with undiagnosed metal scars to prove it. Sometimes the poor kid learns plumbing from his dad then starts and scales a business up to millions in sales.“

That is adorable, and plumbers aren’t poor.


Nobody said plumbers are poor.


"the poor kid learns plumbing from his dad." ..........


That doesn't mean his dad's a plumber, it means his dad showed him some basic plumbing and he took an interest in it that later turned into a career. That's fairly basic reading comprehension so the "........." like I'm an idiot isn't necessary when you're the one adding a bunch of additional context that isn't there.

And let's not forget it's a made up example.


Yeah if we want to speculate on what was left unsaid the only limit is our imagination. Maybe the dad is a wizard or a ninja or something.

It is not just a made up example, it is an outlier, which is why it is so adorable.


undiagnosed metal scars

What are undiagnosed metal scars ?




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