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.
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.
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.
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.
You see this with internal projects at larger companies too, just with fewer constraints. At big companies, the same impulse leads to empire building and vanity projects. Far too few people ask, “how does this deliver value for the company? How does this serve the mission? How does it benefit the customer?”
> 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.
> 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.
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.
> 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.
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).
I'm in tears reading this, I've never seen it worded so perfectly. Have we all experienced that founder who has zero vision for what they're building and is so brutally relentless with ancillary asks?
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.
> 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.
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?
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.
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.
(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)
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
- 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.