[HN Gopher] The side hustle from hell
___________________________________________________________________
The side hustle from hell
Author : jakey_bakey
Score : 246 points
Date : 2025-04-28 17:05 UTC (5 hours ago)
(HTM) web link (blog.jacobstechtavern.com)
(TXT) w3m dump (blog.jacobstechtavern.com)
| cortesoft wrote:
| This just makes me glad I don't work in the startup space anymore
| jakey_bakey wrote:
| Eh, it gets better. I've gone from (this) to my own preseed, to
| a seed, now in a series A. It's always fun and there's always
| lots to learn.
| firesteelrain wrote:
| Sounds like a nightmare. Red flags were visible early on but
| obviously everyone was blind
| jakey_bakey wrote:
| The only person you have to convince is yourself!
| xivzgrev wrote:
| I get it, why a young ambitious 20-something would be sucked into
| this.
|
| Sometimes you just need to make your own mistakes to learn, even
| if you read / hear from others that you shouldn't do that thing.
|
| C'est la vie.
| jakey_bakey wrote:
| I would even say it was a worthwhile experience. I've built my
| career off the startup I landed in, I probably wouldn't have
| got there without being burned here.
| its_down_again wrote:
| Any advice for leveraging a startup role to boost your
| career? I've seen friends turn their positions at early stage
| companies (Pre-Seed/Seed/Series A) into things like raising
| funding for their own ventures, hosting galas at SF museums,
| putting on international fashion shows with their alma mater,
| or even speaking gigs. And honestly, I have no idea how they
| pulled it off.
| dan-robertson wrote:
| Feels like you might get better advice asking your friends
| who've done the thing you can't understand?
| juliansimioni wrote:
| Like many, I also had an experience like this in my younger days:
| obviously unfit product, early prototype made by bottom-of-the-
| barrel contractors, co-founders who can't code, no salary, no
| users.
|
| I got lucky, and spent only a few months while not working that
| hard.
|
| But at the same time, this quote hits home:
|
| >I was doing a startup. I was executing, and for the first time
| in my professional life I wasn't insulated from the results. I
| didn't achieve my destiny of great things, but I'd built
| something.
| jakey_bakey wrote:
| Right? I literally can't even call it a proper warning because
| of how much I took out of it.
|
| My whole career was jumpstarted by my second startup (we only
| got to preseed but it was a great two years) and there's no way
| I'd have been as good a fit without this experience
| bruce511 wrote:
| I think you nailed it here.
|
| >> I hope that by reading this story, I can protect some of
| you from 11 months of pain.
|
| That's not how experience works. What you really did was get
| an 11 month business education. And again, you can tell your
| story, but you can't pass on that education.
|
| I'm glad you moved on to better things. And I think you're
| saying that this experience prepared you for that, and you
| were a better overall entrepreneur because of it.
|
| _Thats_ how experience works.
| skeeter2020 wrote:
| But maybe he can compress someone else's terrible
| experience down to 6 or 3 months, or stop them from sinking
| their own money (or that of family/friends) into an obvious
| faliure. There's another failures to go around; we don't
| all need to life every one of them.
| jakey_bakey wrote:
| Yeah honestly I'm not sure what someone is meant to take
| out of this. The experience is really useful. But if me
| and Gus worked this out after 3 months, we could have
| cofounded our own thing!
| jakey_bakey wrote:
| Absolutely - I mention this at the end. This experience was
| a springboard into my first "real" startup, and I've been
| working my way up fast since then!
| Aurornis wrote:
| This is the classic dead-end startup story from beginning to end.
| It checks all the boxes:
|
| - 3 non-technical cofounders
|
| - Flurry of activity for everything other than acquiring
| customers
|
| - Attempt to outsource development followed by disappointment
|
| - Relentless scope creep
|
| - Zero go to market plan, just an incessant belief that more
| features in the app will solve all problems
|
| There is also one less obvious point that is buried in the
| article:
|
| > Simultaneously, my underpaid mid-level consultancy role passed
| me up for promotion again. I wanted out, double-time.
|
| I did volunteer mentoring for a while. Few people went all-in on
| unpaid startup jobs as their primary role, but many were tempted
| to do it as side projects. They always believe it's less risky.
| The risk they don't see is that it distracts them from their main
| job, either slowing career growth or risking a PIP or layoff.
|
| The common thread I kept coming back to was this: Ignore the side
| projects. Focus on career growth at your day job. Put your
| primary energy into growing your career or finding a job where
| you can.
|
| Something about the side hustle continues to lure people into
| thinking it's a way out, until they burn themselves out and
| sabotage their day job while doing it.
| jakey_bakey wrote:
| Amazing analysis. To be fair, I think there were a lot of
| reasons I was passed for promotion at Deloitte. I can grind
| like a mofo but am a terrible fit for client-facing roles
| (AuDHD).
| joshdavham wrote:
| TIL AuDHD = "Autistm + ADHD".
| jakey_bakey wrote:
| Same, I saw it on Twitter and just wanted to use it :D
| zelda420 wrote:
| Throughout my long career in the tech industry, from
| established giants like Oracle to a hyper-growth pre-IPO
| Airbnb, I've observed a consistent pattern: engineers rarely
| advance more than one level above their initial hiring
| position, regardless of their performance or tenure.
|
| The only exception were juniors who could rise to a senior. But
| senior to staff, or whatever you want to call it is almost
| unheard of unless you jump ship.
| WWLink wrote:
| Just over 10 years in space stuff, I have noticed exactly the
| same thing.
| jakey_bakey wrote:
| Lol I have had one promotion in my life and it was mid-Junior
|
| That said, I have only moved jobs 2x in 9 years (my second
| startup failing doesn't count)
| Aurornis wrote:
| > The only exception were juniors
|
| The article mentions being an early career junior in the
| first few sentences.
| greatpostman wrote:
| Yup. You get Bucketed and there is no growth
| bathtub365 wrote:
| Over about 10 years I moved from mid level developer to
| director (through senior, team lead, engineering manager, sr
| engineering manager) at the same company. It was a small
| company that grew and the founders/high level engineers
| actually saw the value in retaining and growing people and
| had interesting enough work to keep people from getting
| bored, so we had high retention.
|
| Many of these promotions were out of cycle (because there was
| no cycle) and now that I'm at a bigger company I see how this
| would be much more difficult. There seems to be little
| interest in really retaining and growing engineering talent
| and all promotions are at the mercy of an entrenched HR org
| that doesn't understand the work that anyone is doing. On top
| of that budgets are generally much tighter now than I've ever
| seen during my career.
|
| It may still be possible to do this at smaller companies,
| with the obvious caveat that there's always the danger of
| title inflation, though now that I'm at a bigger company I
| feel like I see more title inflation around me than I ever
| did at the smaller company. There are also entrenched
| structures of power that are obviously working against the
| success of the company and are causing good people to leave.
|
| I do wonder if more companies embraced promotions it would
| lead to a healthier organizational culture in general since
| you'd have more people around who were involved in creating
| it.
| jimbokun wrote:
| It seems like the simplest reason for the discrepancy in
| behaviors is that in the small company, the higher level
| roles came into being organically as the company grew.
| Where as at the already established large company, to get a
| higher level role you almost have to take it from someone
| else. Or wait for a vacancy.
| mattgreenrocks wrote:
| It's a professional version of "a prophet is not without
| honor, except in his hometown and among his relatives."
|
| Familiarity begets being taken for granted, and
| undervaluation, which hurts one's promotion case.
| toast0 wrote:
| > unpaid startup jobs
|
| Unpaid job is an oxymoron. If they can't or won't pay you, it's
| either volunteer work, or a hobby. Why do charity work for a
| business that thinks it's going to be big; there's plenty of
| funding out there, let them find it and then they can pay you,
| and you can do work for them.
|
| If you want to do an hour or a day or maybe even a week of work
| for free, ok. Maybe that's fun and interesting and you get
| something out of that, but after that if you're not getting
| anything, why would you keep doing it?
| jakey_bakey wrote:
| It's easy to be naive as a dev in your mid 20s. It's easy to
| sell a vision of billionaire startup success to a naive
| person. Often we sell it to ourselves.
| toomuchtodo wrote:
| Feels like there should be the equivalent of Matt Levine's
| "Certificate of Dumb Investment" for this scenario. ~90% of
| startups fail. Your equity is statistically likely to be
| worth $0. You will likely grind for years with nothing to
| show for it except the experience, your network, and
| whatever cash comp you collected. Proceed accordingly.
|
| https://news.ycombinator.com/item?id=24285305
|
| (edit: totally fine to still jump into a startup role if
| you're not optimizing for quality of life and economics; I
| did because I enjoyed the work and the team)
| jakey_bakey wrote:
| Yeah, the only real regret is I could have got this
| experience more quickly with less pain and time not spent
| with my wife
|
| Edit: just realised that made it sound like she died.
| She's fine! We just had baby #2! But we could have spent
| lockdown making bread and playing RuneScape instead of me
| grinding
| StefanBatory wrote:
| Because you need experience. At least in my country, unpaid
| internships are the norm; and you won't be taught anything,
| or held to a lower standard. You just do the job that you'd
| be normally paid for, just for free.
|
| And even then, I had a few friends that had to go for another
| few months of unpaid job (not internship) later on. Because
| nobody would hire them without experience, and some companies
| don't consider internship to be one.
| codingwagie wrote:
| I think its completely possible to start a side business,
| people just dont 100% validate business ideas before building
| cynicalsecurity wrote:
| PIPs and layoffs happen to anyone, often randomly. A manager
| doesn't like you? Here, have a PIP. Good luck trying to seek
| justice in this situation. You could be working perfectly fine,
| but the company is complete trash with with hideous ethics.
|
| Side projects help finding a better job, or at the very least
| work on getting certifications or self-development to find a
| better job.
| miek wrote:
| Side hustles can be very fruitful! While not tech related, I
| side hustled with a friend into starting a specialty wet wipe
| manufacturing business that we ran for 4 years and sold. The
| side hustle phase was done on PTO and weekends. We worked with
| the machine maker to get samples that we took to
| restaurant/hospitality expos to gauge demand. We made a deal
| with the machine supplier to send finished goods until the
| machines arrived. Four years later we sold it and I went back
| to corporate life. It was worth 100x an MBA.
| Aurornis wrote:
| > The side hustle phase was done on PTO and weekends.
|
| Having a physical business and operating it on PTO and
| weekends is the cleanest way to keep it separate from work.
|
| The tech side hustle mistake is to get a tech job, then think
| you'll do some more tech work as a side hustle. Some people
| can keep a clean separation, but more commonly people slide
| into blurring the lines between day job and side job. Trying
| to build a startup MVP while working a consulting job is
| basically doing two tech jobs at the same time, with
| predictable outcomes for both.
| aresant wrote:
| "Flurry of activity for everything other than acquiring
| customers"
|
| In 16 years on HN this is one of the best pieces of startup
| advice I've seen.
|
| Default should be 10% of time on MVP and landing page, 90% on
| distribution until you smell PMF.
|
| Fight violently against any suggestion you invest more heavily
| in product until somebody is in tears about keeping up with
| demand for your MVP.
| jakey_bakey wrote:
| Bingo. Tbh I have done personal projects where I am guilty of
| this.
| RowanH wrote:
| > Something about the side hustle continues to lure people into
| thinking it's a way out, until they burn themselves out and
| sabotage their day job while doing it.
|
| Sample size of 1
|
| - Side hustle #1 funded my toy habit for a long time and gave
| me the confidence "I can build & support something from start
| to finish".
|
| - Got to C Level working for 'the man' (aka the board). But
| regardless of level you're never in control of your destiny,
| especially with the eventuality of PE. For some that's okay,
| for others that's not...
|
| - Which lead to Side Hustle #2. Left my day job 3 years ago....
|
| Now have some of the best in our wee niche using our product, a
| number of team members, gradually growing it in bootstrapped
| fashion.
|
| No investors, no funding rounds, no chasing growth targets. As
| "pure" as it can get - adding features, capturing more market,
| getting positive word of mouth, picking up new countries,
| finding new edge cases, adding new package upgrades. I think
| we're around 40% of new clients are referrals/word of
| mouth.....
|
| In the first 6 months of turning billing on you're going "what
| the heck am I doing...." now I'm "oh I wouldn't give this
| up..." immensely rewarding bringing other new people into the
| business, and seeing that flow through to the finished product
| for our clients.
|
| At least in NZ, side hustles are the genesis of a lot of tech
| companies.
| nipponese wrote:
| You can stop at - 3 non-technical cofounders
| mattgreenrocks wrote:
| Excellent analysis.
|
| > Something about the side hustle continues to lure people into
| thinking it's a way out, until they burn themselves out and
| sabotage their day job while doing it.
|
| Side projects are a way to assert control. The siren song is
| that you can build your own way out of corporate hell and have
| a shot at growth (be that financial/personal/etc) without
| needing 10 randos and 3 committee meetings from your company to
| sign off on a promotion. In that light, I think it is a very
| reasonable response.
|
| I think it's a symptom of how crappy and ambiguous leveling
| feels over the long-term. You're told that nothing's definite,
| just work hard and deliver results, and you'll make it.
| Juliate wrote:
| > This is the classic dead-end startup story from beginning to
| end. It checks all the boxes:
|
| Oh my... I concur. I've been in the very exact same stupid play
| about 10 years ago. 3 cofounders, not one to understand tech, 1
| hired me as a consultant, then invited me with a few shares and
| a salaried CTO role to build the solution, and it's been the
| exact same scenario.
|
| Do not, ever, associate (figuratively or contractually)
| yourself with people you wouldn't go hiking with in the wild
| for one full week, and coming back from it craving for the next
| time.
|
| Even if you can't stand being in the same car for one hour,
| don't work with them at all.
| TrackerFF wrote:
| Yeah, sounds like the product was DOA. All that time _not_ spent
| on acquiring customers - but chasing the "perfect product".
| jakey_bakey wrote:
| So much time could be saved by listening to 10 hours of YC
| podcasts ...
| photochemsyn wrote:
| Very surprising that well-designed contracts (with well-designed
| exit clauses among other issues) aren't at the top of the 'ten
| red flags' list. This isn't just a problem with tech startups -
| business partners down the ages have been burning each other with
| flimsy contractual agreements and 'trust me buddy' rationales
| when questioned about the contracts.
|
| This is one of the best use cases for LLMs by the way - they can
| often explain contracts to you, or find flaws in contracts. Try
| pasting one of those long-winded click-through contracts from
| Apple etc. into any LLM and see if they can help you decipher the
| terms - then do this with your startup's hiring contract. Also,
| watch 'The Social Network' and pay attention to things like
| stock-split clauses and so on.
|
| Some claim the world is split between those who understand
| compound interest and those who don't but I think it's
| understanding contract law that matters more.
| codingwagie wrote:
| any extremely long contract with obtuse terms is designed to
| screw you in some way. you just wont know until you get there,
| unless you are willing to spend 10-20k on lawyers to argue the
| terms
| skrebbel wrote:
| This is not true. There's plenty super friendly contracts
| that just happened to be written by lawyers who are into
| legalese maximizing. I can imagine that someone trying to
| screw you over might use obtuse terms to hide that, but the
| reverse isn't always true. Sometimes things are just obtuse
| for stupid reasons.
| codingwagie wrote:
| in my experience it is 100% true, every contract i have
| seen with over legalese is created by people who expect to
| be acting on those terms
| VWWHFSfQ wrote:
| > watch 'The Social Network' and pay attention to things like
| stock-split clauses
|
| > but I think it's understanding contract law that matters more
|
| It's best to just pay a real attorney instead of trying to
| learn something from a TV show or fact-check the hallucinations
| of an LLM.
| jakey_bakey wrote:
| Bingo. It's why using SeedLegals (boilerplate contracts with
| simple customisation) was such a breath of fresh air.
|
| I've even worked at bigger places with very scummy equity
| contracts, like a lawyer drafted it specifically to obfuscate
| how badly it was screwing you over. Not there anymore lol.
| lurk2 wrote:
| > This is one of the best use cases for LLMs by the way - they
| can often explain contracts to you, or find flaws in contracts.
|
| I respectfully disagree. Just hire a lawyer. You don't want
| your understanding of your contract colored by the opinions of
| an LLM. The lawyer carries liability insurance if he gives you
| bad advice. If you don't have a few hundred dollars to spend on
| independent legal advice, you might want to reconsider if you
| are in a position to be starting a business in the first place.
| The amount of money you could potentially save is nothing
| compared to what it could cost you in the future if something
| goes wrong.
| photochemsyn wrote:
| Interestingly Ben Mezrich (author of The Social Network) said
| the Facebook partner who got hit by the stock-split clause
| terms had hired a team of lawyers - but he claimed they were
| really working for the Zuckerberg side, possibly in-house
| lawyers.
|
| There might be great value in LLMs fine-tuned to deal with
| contractual law, regulatory law, and legislative
| interpretative dance. At present I'd be sure to run the legal
| contract through multiple different LLMS at the very least,
| and analyzing it paragraph by paragraph in debate club manner
| (LLM A: tell me why this is a good contract, LLM B: tell me
| why this is a bad contract, LLM C: analyze the flaws in the
| arguments of LLM A and LLM B, etc.) Doesn't replace a good
| contract law specialist human, certainly, but at least you
| can then talk to your lawyer in a semi-informed manner.
|
| LLMs are like compilers in that unqualified faith in their
| initial output is never a good idea.
| wibbily wrote:
| Currently at a startup that did the same thing wrt having their
| app built overseas. Protip: don't. Endless bullshit, excruciating
| trying to get _anything_ out of them. We ended up with an app
| just like this guy 's, locked aspect ratio and all.
|
| If I find another startup whose product is an app, and they can't
| find a local developer to write that app, I'm running. Why
| outsource your core product!?
| jakey_bakey wrote:
| It's the classic case of believing that ideas at 90% of the
| value and execution is something you can delegate. Think
| Kendall from Succession.
| constantcrying wrote:
| Because there are legions of people out there who want to be
| "entrepreneurs", so they come up with "business ideas". They
| can't make these ideas into reality by themselves, as they lack
| all technical skill. This lack of skill also means that they
| can not manage a project, as they lack a basic understanding of
| how software project works.
| icedchai wrote:
| This is very common. Lofty idea folks often see developers as a
| commodity, so why not just outsource to the cheapest bidder?
| You might luck out and get a smart person who doesn't know what
| they're worth yet... but, 9 out of 10 times, you get what you
| pay for.
| VWWHFSfQ wrote:
| I've worked with many startups and many VCs. The best VCs are
| investing in _the team_ , not the product idea. The idea itself
| is basically nothing. It can get blown up in an instant and
| require a pivot. But the investor wants to know that the money
| they're giving out is going to people actually recognizing that
| and capable of successfully switching gears.
|
| They're investing in people, not some singular half-baked idea
| that very likely goes nowhere.
|
| In this case it sounds like both the idea was bad, and the team
| was bad.
| jakey_bakey wrote:
| Many such cases!
| aorloff wrote:
| Everyone wants someone else to do the hard part, but wants to
| "own" something
|
| Bitches, owning something is doing the hard part !
| jakey_bakey wrote:
| I'm an entrepreneur, bitch. Ideas + delegation!
| icedchai wrote:
| This attitude is also very common. When I see a small company
| with lots of "leaders" and far fewer doers, it's a huge red
| flag.
| vessenes wrote:
| Oof. Sorry. Missed in this story because Jacob is in Europe/UK is
| that this level of absolute incompetence in a launch team is, in
| my experience, extra common on that side of the pond.
|
| There are of course some fantastic startups launched out of the
| UK and Europe. Spotify, Deepmind and Raspberry Pi come to mind.
| But, as a rule on the investment side, I'm always super
| skeptical. Inevitably cap tables are worse, investors have a very
| different view of their roles than they do in US or Asia, and
| there's so much less startup infrastructure than in SV or say
| Singapore or Shanghai that it's a very different world.
| Ironically, it's self-feeding -- investors think startups are
| shitty business, they charge more, high quality founders head for
| greener pastures -- rinse and repeat.
| jakey_bakey wrote:
| Haha to be fair I have been adjacent to lots of startups like
| this. I also spent a few months attending weekly zoom calls for
| a side hustle that was effectively some mid level bored
| corporate people blowing off steam. They were a few steps
| behind getting a bankloan.
| ChuckMcM wrote:
| I love this story. Why? Because it is the story of so many
| startups. I was so perplexed in the mid-90's when the dot com
| "boom" had started by people who wanted to do a "startup" but had
| no idea what that meant. Like the author, people with a feeling
| of Destiny that they would be some leader of something that
| everyone talked about. I had the same beliefs when I left Sun
| where clearly I would never be "famous" but by starting a company
| that became big? Sure anyone could do that. And in fact, a peer
| at Sun for whom I felt was not particularly qualified at
| anything, had gone on to a startup which had then gone public and
| made millions! And if he could do it, well it was guaranteed for
| me, right? Yeah, no.
|
| At the other end of my career and looking back it becomes
| possible to see things that you missed on the journey, the role
| of luck, the difference between talking hard and working hard,
| and the critical importance of the people involved. A million
| monkeys with a million typewriters won't eventually create
| Shakespeare's works, they will waste a lot of resources and
| create a bunch trash. I also discovered that there are people
| who, when they speak, you really _want_ to believe what they are
| saying. Being able to step back and say "what's the foundation
| here? Why should I believe this?" can be very difficult.
| jakey_bakey wrote:
| Do you think a million monkeys with a million typewriters could
| come up with Oracle Database 11?
| jimbokun wrote:
| Is an existence proof allowed?
| _DeadFred_ wrote:
| Pitch: It's a replacement for Blockbuster. But instead of going
| and getting instant gratification and getting to watch the
| movie you want to watch tonight, you create a wishlist and we
| send you 3 titles off that list (normally the 3 least popular),
| which may or may not be what you want to watch right now, and
| add the convenience of injecting the United States Post Office
| into the process.
| ChuckMcM wrote:
| https://xkcd.com/2618 right?
| praptak wrote:
| A million monkeys with a million typewrites will statistically
| have one lucky monkey who creates an extremely successful
| product which also looks very dumb and very unconvincing
| ("Srsly? You want to make money from random people hosting
| strangers in their own rooms?" Bang, AirBnB)
|
| The problem is selection bias. A startup is 3 monkeys tops, so
| the chances of that are appropriately low and if the product
| looks dumb and unconvincing, it probably is ("...but they also
| laughed at Bozo the Clown.")
| ChuckMcM wrote:
| There should probably be an entire chapter written on "Okay,
| but what if the product was desirable but not 'technically'
| legal, hmmm?" :-)
| praptak wrote:
| It would say "we all know how it went" :)
| ChuckMcM wrote:
| Had an interesting discussion this past weekend on
| whether or not Silkroad was a criminal enterprise or a
| very successful startup. It was an interesting look at
| the question of 'business first' versus 'lawful first'
| societies and their relative success through history.
| jimbokun wrote:
| I would say good luck finding enough very successful
| companies NOT matching that description to fill a chapter.
| joshdavham wrote:
| Really cathartic read! Thanks so much for writing this. I really
| related to parts of this and the red flags you point out are very
| much the red flags I've also noticed with other startups. I
| almost feel like this could be "required reading" for some.
| jakey_bakey wrote:
| I hope @paulg asks me to give this talk at demo day
|
| I can make it funnier!
| ugh123 wrote:
| > In one Monster-and-Elvanse-fuelled night of passion, I was
| light years ahead of a build that had taken 3 years. They were
| sold.
|
| MY MAN!
| jakey_bakey wrote:
| AuDHD represent :ok:
| Havoc wrote:
| Well at least he took learnings from it
| jakey_bakey wrote:
| Hahah it was probably just about worth it. Wouldn't if I had
| kids or it wasn't mostly in COVID time
| OtherShrezzing wrote:
| An additional red flag - if your company lists "being SEIS
| registered" as a point of traction, run a mile. Literally every
| newly registered UK company can get this by spending 60 minutes
| filling out a form that says "my company is risky, I intend to
| raise money from VCs".
| jakey_bakey wrote:
| "This will be a great differentiator when looking for funding!"
| constantcrying wrote:
| Having non-technical founders who failed to even outsource their
| project is an enormous red flag. Nobody there knew how to make
| the product a reality and if it is you who is doing 100% of the
| work, then you obviously deserve 100% of the equity. "Having an
| idea" is not worth equity.
|
| If you thought the idea was great, there was an obvious golden
| opportunity for you, none of the people there are going to make
| this into a product, but you can. If the idea was bad, getting
| paid in equity means getting paid in something worthless.
|
| The only situation where it is reasonable to deal with such a
| totally defunct organization is if they pay you _a lot_ of money.
| And if there is a single missed payment you stop any work until
| you are paid.
| jakey_bakey wrote:
| I certainly should have spotted this as soon as they offered me
| a contract that was a clumsily-reworded version of the contract
| for the awful overseas contractors
| hinkley wrote:
| Too many fantasy tales of overnight successes out there. It
| takes an enormous amount of work to make things look easy - in
| a commercial setting. Some people just pick things up and are
| relatively good at them but they cannot productive it. To do so
| you have to be able explain it and they don't understand it,
| they just do it. So they can't make a business out of it and
| they cannot become top of their field because they lack the
| fundamentals and the work ethic.
|
| I could talk anybody to death with all of my ideas. I only get
| to work on very few of them. I can't imagine how sad a life it
| would be to only have one. It's great for mentoring though
| because there's always something shiny on the shelf and I can
| let them window shop for one they like.
| superconduct123 wrote:
| I'm thankful I got to experience working at very early startup as
| a summer intern rather than full time
|
| That gave me enough info to know I'd prefer working for a big
| company
| eqmvii wrote:
| Lovely article. The payoff of "I loved every minute of it" after
| all the agony and missed red flags really hit home.
| jakey_bakey wrote:
| Thank you for reading :)
| generationP wrote:
| So an app that would probably serve a real need fails because the
| team is unable to bootstrap the two-sided market. The best dev
| moves to a bullshit "green habits" app that doesn't suffer from
| such problems because... it doesn't really do much in the first
| place. Not the greatest outcome for the world.
| jakey_bakey wrote:
| Hey man, don't knock 2020/2021 ZIRP era projects
|
| Don't you remember before inflation when we were able to focus
| on climate change!
|
| But you totally got us there, the startup failed because we
| were a vitamin (and because our on-the-fence seed round was
| scuppered by Putin cooling some feet)
| gavmor wrote:
| > The cofounders didn't have access to the code repo
|
| Get the fuck outta here. I couldn't read past that. I'm done.
| Thanks for the writeup. Godspeed.
| jakey_bakey wrote:
| "This is just object code for my idea why would I want to read
| it"
| dabinat wrote:
| This article reminded me of the time a guy wanted to pitch his
| startup idea for me to develop. He wanted me to sign an NDA
| before telling me, as the idea was so great that I would
| obviously steal it, which I refused.
|
| So all he would tell me is that it was "the next Twitter", and
| from what I could gather, he would retain the majority of the
| equity and I would do all of the work, while he lobbed ideas at
| me from on high.
|
| I passed on it, but only because the red flags were extremely
| obvious. I could certainly see a situation where I might have
| been sucked into something more subtly exploitative.
| kjs3 wrote:
| I can't even count the number of times I've heard this pitch,
| complete with NDA demand. The only answer is "Thanks, but no
| thanks". I have never had to regret it.
| bityard wrote:
| This needs to be highlighted: Everyone who does anything at all
| in the realm of business or tech should basically never sign an
| NDA unless it is already positively guaranteed they are getting
| something out of it. You might be required to sign an NDA once
| you have been hired at a W-2 job if the company handles
| sensitive data. Or if you have already been offered a contract.
| Event then, make sure it is actually necessary, and run it by
| your lawyer.
|
| But if someone wants you to sign an NDA just to hear about
| their idea or business, or as a condition of being interviewed
| for a job, ALWAYS say no. VCs don't sign NDAs and neither
| should you. It's plain and simple uncompensated risk.
|
| https://blog.jpl-consulting.com/2012/04/why-i-wont-sign-your...
|
| https://www.markwelchblog.com/2009/08/26/why-i-dont-sign-nda...
|
| https://blog.hartleybrody.com/wont-sign-nda/
| pizzathyme wrote:
| Rather than being a cautionary tale, I actually think this is the
| kind of misadventure that everybody should have. You learn so
| much about the real world from a failed startup where nothing is
| done right (at least I did). Your early 20s are the perfect time
| to do it with little risk. Lots of painful memories I laugh at
| later. Highly recommended.
| jakey_bakey wrote:
| Yep this is exactly my summary at the end! I'm glad I sat on
| this story a few years to let it develop and let the positive
| career consequences play out.
| bitbasher wrote:
| The first red flag is a startup that is contingent on a two sided
| marketplace... damn that's a tough place to be!
| mandevil wrote:
| The only times I've ever heard of this working are when you
| have a huge war-chest to subsidize both sides of the
| marketplace to come out and play on your app. If you can offer
| better prices than normal to both sides (with the gap made up
| from your raises) it can work. Otherwise? I'm not sure it can.
| paulorlando wrote:
| Liked this: "Startup pitch competitions are mostly a waste of
| time--validation comes from talking to users and iterating, not
| from impressing a judge."
| htrp wrote:
| Advisory roles only advise. Once you start doing work, you're
| basically an employee.
| buzzerbetrayed wrote:
| That was such a great read. And way too relatable at parts. Loved
| it. Makes me want to write down my startup stories one day, even
| if it's just for friends and family.
| andrewstuart wrote:
| I do all that by myself and play all those roles at the same
| time.
| kikimora wrote:
| I've been running an outsourcing business for a while and can
| confirm - 99% of people paying for development have no idea what
| they are doing and how to sell it. They are destined for failure
| unless the outsourcing team builds a product that is 3x better
| than a competitor with 100x funding.
|
| Success stories I've seen always involved extremely active
| customer. They become part of the team, helping devs to build
| good product. Also it always took much more time and money. If
| you think you can build marketable product with fix-cost-scope
| contract - think twice.
| jkaptur wrote:
| > If you aren't sure what your cofounders are doing, trust your
| git instinct.
|
| That's good advice to not lose your HEAD.
| readthenotes1 wrote:
| "Look at the specification. It does not specify anywhere we were
| asked to support screen dimensions larger than iPhone 4s sized."
|
| I wonder how many outsourcing firms are going to be replaced by
| vibe coding. This response is pretty on par with many of the
| horror stories responses I've seen over the decades...
| harshaw wrote:
| This isn't so much about the Author's story but the space. He is
| correct that marketplaces are hell, and especially auto repair
| market places. I was one of the several devs that went through
| trying to make Openbay work (a US based market place for auto
| repair). We actually did have service providers signed up and we
| did have a way to acquire customers who wanted auto repair. So
| you had the illusion of product market fit - but the problem is
| that it's really really hard to get people to actually click "buy
| this brake job" and then, more importantly, they have no reason
| to come back to your app because 1) you don't need brake jobs all
| that often and 2) they can just go back to the service provider.
| And many shops are happy to still take phone calls as their
| default way of booking work.
|
| The reason the company existed is the rich founder was upset that
| a shop wanted to charge him a fortune to get his BMW M5 repaired.
| He wanted better quotes. So we built a marketplace to get better
| quotes. But that's not what real customers want (because most
| people have Toyotas not M5s). And also we didn't do the customer
| development / research to understand how repair shops work. You
| want to know how my repair shop manages their repair schedule?
| They have a paper calendar and write down your phone number and
| the job. sure there are better ways to manage the work - but this
| paper mechanism has worked for them for years and why change it?
| And you know what - I go back to the shop all the time because I
| trust them. Ultimately people tend to have a fairly personal
| relationship with their local mechanic. You can build a leadgen
| product but the ultimate relationship is between the customer and
| the repair provider.
|
| TLDR - everyone should understand the lean startup. /working
| backwards model and relentlessly focus on the customer.
| bityard wrote:
| > Ultimately people tend to have a fairly personal relationship
| with their local mechanic.
|
| This is the money line. And it goes for all skilled trade work.
| Mechanics, plumbers, building contractors, roofers. Most of the
| people doing this work are just surprisingly bad at it,
| especially for how much they charge for it. It takes a LOT of
| time and effort to find someone good. I'd even lump doctors and
| dentists into this.
|
| I don't want a marketplace to tell me who's the cheapest, I
| want a marketplace to tell me who's the best. And unfortunately
| there's no way to build that. (Why is a long story, but the
| short version is: because there's no way to build the correct
| incentives into it.)
| nyarlathotep_ wrote:
| I've always been surprised at the sheer amount of work that's
| outsourced in software/IT.
|
| Even companies that had staff of developers would often outsource
| work that should be part of their core competency. Without fail,
| every time, they ended up with a bill ~an order of magnitude
| higher than they'd pay if they were just hiring competent staff
| to deliver the project.
|
| In many of these cases, these same firms would then hire another
| (lower quality) company to maintain it for them. This typically
| went as expected.
|
| I could never understand the rationale for a lot of these cases.
|
| "The existing staff is busy"--but they could have two hours of
| meetings with us daily?
|
| "They don't have competence in those areas"--they're already
| using $CLOUD and $THAT_STUFF? It often was working with existing
| systems?
|
| "Costs"--again, see above.
|
| I really could not understand the motivation. I get it for
| clients that had no experience in what we were sent to do or got
| sold on something they didn't need, but a majority surely had or
| could get the resources to do the projects that were done, but
| opted not to, for whatever reason.
|
| I've seen this kind of thing fail on many occasions.
|
| If it's critical for your business, (ya know, not some LLM demo
| or something), you need ownership, otherwise you end up with a
| far larger cost of ownership and piles of logistical and quality
| problems.
|
| I genuinely can't imagine a start-up doing this. Everything I've
| seen is private sector companies, most ~competent companies.
|
| I'll say this, the cases where I have seen success in consulting
| (from the perspective of the 'buyer' is those that were
| intimately involved with the process from the start, providing
| feedback and pushing back when needed and taking initiative
| deliberately to "on board" so they could maintain and use
| whatever it was they got, and typically working alongside
| consultants)
|
| You also have to basically avoid most consulting companies. I
| won't name them, but it's not hard to guess.
| indoorcat wrote:
| Extremely relatable. I was the first technical hire for a startup
| that ultimately failed last year. I did at least have a (below
| market) salary, and there were no outsourcing headaches, but I
| really did spend an inordinate amount of my time trying to
| perfect a product that the founders had no idea how to market. I
| certainly learned a lot, though it made me a little cynical about
| startups and the tech industry in general. Maybe in a couple more
| years I'll feel more positively about the whole experience.
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