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The side hustle from hell

blog.jacobstechtavern.com

11–20 of 146 posts

Re: The side hustle from hell

#12
post #6

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…

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).

Re: The side hustle from hell

#13
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.

Re: The side hustle from hell

#14
post #6

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…

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.

Re: The side hustle from hell

#15
post #6

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…

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…

Just over 10 years in space stuff, I have noticed exactly the same thing.

Re: The side hustle from hell

#16
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.

Re: The side hustle from hell

#17
post #6

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…

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…

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)

Re: The side hustle from hell

#18

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 f…

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

Re: The side hustle from hell

#19
post #6

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…

> 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?

Re: The side hustle from hell

#20

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 ca…

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
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