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The side hustle from hell

blog.jacobstechtavern.com

31–40 of 146 posts

Re: The side hustle from hell

#33

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 t…

Many such cases!

Re: The side hustle from hell

#34

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

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.

Re: The side hustle from hell

#35

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…

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.

Re: The side hustle from hell

#36
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…

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.

Re: The side hustle from hell

#37
post #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…

[deleted]

Re: The side hustle from hell

#38

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

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.

Re: The side hustle from hell

#39
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.

Re: The side hustle from hell

#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 machines arrived. Four years later we sold it and I went back to corporate life. It was worth 100x an MBA.
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