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The side hustle from hell

blog.jacobstechtavern.com

41–50 of 146 posts

Re: The side hustle from hell

#41
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…

Yup. You get Bucketed and there is no growth

Re: The side hustle from hell

#42
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).

TIL AuDHD = "Autistm + ADHD".

Re: The side hustle from hell

#43
post #19

Earlier quoted context omitted.

> 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…

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.

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)

Re: The side hustle from hell

#44

Earlier quoted context omitted.

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

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.

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

Re: The side hustle from hell

#45
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…

"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.

Re: The side hustle from hell

#46
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…

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.

Re: The side hustle from hell

#47
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…

> 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.

Re: The side hustle from hell

#48
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…

You can stop at - 3 non-technical cofounders

Re: The side hustle from hell

#49
post #40
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…

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 mach…

> 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.

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