There are plenty of startups and “startups” that are about a decade old and would benefit from someone who has both an understanding of how real startups work, how to ship things, and also has enough experience to be reliable in what is no longer an early stage company, and maybe isn’t really a startup anymore.
A lot of these companies make reasonable money and pay well enough. Not $100k and “$10MM in stock if it works out”, but probably between 170-300 depending on where they’re at, the structure, etc and it’ll be real cash money. The company will probably do something boring but very necessary. You’ll make great friends and have fun.
Keep an eye out, see what’s out there.
Startups are a terrible way to make money. It is far far easier to make money at a larger company than it is at a startup. It's even worse if you start the company yourself. The chances that you'll ever make money are pretty small, and getting to a regular salary can take 3-7 years. Even the chances of making life-changing quantities of money are much smaller. I've been working in this industry for 40 years and all the people I know who are rich did it at big companies, most recently at Nvidia, earlier at Apple, Sun, Facebook and similar. I know tons of startup founders. Almost none of them made significant money. It's more like authors and artists - start a new company because you are driven by an invisible force and you want to do things that you can't do anywhere else. Maybe you want to run your company differently. Maybe you want to work on something that nobody has figured out how to make profitable. A great reason to take a job at a startup is that you like working with small teams and You think you can learn from your coworkers. Do it because you have no other choice, not because you want to make money.
I worked at two startups before realizing that they weren’t what I wanted out of life. Work is important to me, but so is life. I was duped into this vision of entrepreneurship and making it big in startups. While every startup founder likes to spin the story of wanting to be a unicorn, in practice, few do. I happened to work at ones with an insane workload and a less-than-survivable payout.
I interviewed like crazy and landed a position at one of those well-known companies. Large companies have their fair share of problems, but it suits my lifestyle. I do my work diligently and then clock out. It’s liberating to know that if I don’t respond to a pager, the world isn’t going to end and some third-grade CEO/CTO won’t scream in my face.
Different people want different things out of life, and I made a vow never to join a startup or scale-up with fewer than a thousand employees.
Freelance/contract - if you have mildly above average skills and a network, you should be able to find these contracts and they will pay for a mild lifestyle.
I truly believe you won't be able to find a full time job because your preconception is half-retirement. You want to just be stuck at a level of a new grad salary - no company wants anyone that is stuck, they want people that will grow. Once you've chosen to stop growing, freelance is probably the best bet since companies, big or small, don't care about growth fron their contractors. At least, that's been what I settled on after startup burnout.
> I feel like a freaking loser given my age and my relative career stagnation / my inability to actually turn my mildly above average skills into any real money.
It is okay to feel like that for a bit. But, this story that you are telling yourself is not going to help you if you keep on telling this. Whenever I have felt negatively about myself like that in the past, it has helped to stack some wins -- even if little ones -- to get out of the rut.
So, if you want to try to be an engineer, start building things using tools/tech that you are interested in and put them in the open source. Or better yet, help out some open source projects that you respect and have benefited from in the past, if you can. Hiring managers (and I have been one) look for real evidence of skills mentioned in the resume and a well-rounded Github repo increases the likelihood of a callback in any kind of market. Stack some little wins there.
OR, if you want to be a product person, do the equivalent of stacking some wins in that realm. I have very little experience in that space so maybe someone else here can identify a concrete thing or two that you could do to attract hiring managers in that line of work.
I work in technical diligence, so I look at companies getting bought by PE funds – not VC funds – but PE funds looking for boring, unglamorous, reliable year-over-year investments. There are tons of these companies out there. TONS.
A lot of them pay their seniors very well, most pay them well, and they look like nice places to have a "normal job". But they don't get press attention, they don't get talked about on socials (inluding HN), and they don't advertise the same way as others. A lot of them you wouldn't even think of as "software companies", but they build software that makes them the best in some oddball domain programmers never think of, so they are normal, profitable businesses that don't run out burn and crash in balls of fire laying everyone off.
My advice would be broaden your skill set to encompass a wider range of both the stack and of less hip technology, and then start looking and advertising outside the normal startup-heavy places. They are totally out there.
My suggestion is this: Founders often underwhelm on paper, but knock it out of the park when in person. Network in your city with leadership of companies at any stage.
Example: Last month, I was just messing around with an idea, told my vision for it in 5 years to someone that works at a company that should do $400M revenue this year, $800M in 2 years. He had never met his CEO.... his CEO heard my thoughts and offered to FLY cross country out to meet me... someone who doesn't even work there.
Work at a non-tech company. Every company has computers. I’ve worked in small business loans, ticket sales, music publishing and others.
First of all, don't see yourself as a loser! Having worked in startups for so many years, the experience you've accumulated is a huge asset. The previous startup experiences might have affected your interviews because you didn't highlight the transferable skills you gained from those experiences, such as rapid learning, complex problem - solving, and adaptability. You might as well focus on these general skills in your resume and interviews and downplay the label of startup failure. As for the job - hunting direction, apart from traditional tech companies, some emerging industries, such as green technology and medical technology, also have growing demand for people with technical and product experience, and the competition is relatively less intense. Have you considered them? Also, you mentioned the salary level of new graduates. In fact, with your experience, you can definitely strive for a higher salary. Have you studied how to highlight your experience advantages in job - hunting to match positions that meet your expected salary better?
You've worked at and founded startups and so you must have done sales and marketing. This is no different, you're just pitching yourself. Understand who your audience is and what they're looking for and don't forget, presentation is everything.
Positioning yourself correctly, too low and you'll never get past the sea of grads.
Distill your history down so it appears you've had a more stable career history. A random HR bod is going to review your CV and they do not care how many startups you've founded or accelerators you got accepted into. If you've got loads of entries in your career history they're going to stick you on the no pile.
Regardless of how it is internally, corporations don't like lone wolves or individual contributors. They have 'company values' and want someone who works well in a team, has done some mentoring, works well with others, understands the processes, etc etc etc (that is until you start then it's all about delivery). I'd try positioning your CV to appeal to those values with the technical skills to back it up.
In summary - lose the fluff from cv/applications - present a more stable career history - emphasis on teamwork, working with other departments, mentoring
And, I wouldn't worry about AI, offshoring - yes, AI - no. I'm still waiting to be shown an AI-generated SaaS app with real users, or even a functioning tool that's not just a clone of Flappy Bird.
Frankly, few mature companies need a "engineer/product guy" and your split experience will work against you unless you make it clear that you're earnestly committed to one of those roles in particular (are you?), or you specifically look for work close to sales at B2B or contract development firms, where the combination of those skills is an asset when selling and sometimes prototyping custom work.
You're selling a product right now (yourself) and you need a clear understanding of what the product is. It's not a typical engineer and it's not a typical product person. It's not even an practiced corporate drone. So don't expect to sell it as one of those things and don't distract yourself applying for work that needs them (your resume will be ignored in this market). Instead, figure out what niche value your background brings and focus directly on selling that to the customers (employers) that would need it.
I'd just describe this job market as competitive and every company appears to be looking for some specific persona now. Believe it or not you could thrive in this job market. For you, I'd say you'll have figure out what you love to do, figure out how to speak positively/enthusiastically about your previous experience, and find companies that value what you bring to the table. AI is not taking all the jobs yet (seems clear that it produces garbage code that's untenable at scale), and neither is off-shoring (it's very out of trend).
Question - what can you actually control about companies you're applying to? The answer is not a whole lot, so why stress about it? What you can control is a funnel:
1. How many jobs you've applied to
2. What quality those companies are
3. How much they're aligned with your skill set
Other than that, you're stressing about stuff you can't change. Let it go, gain inner peace. There's a lot to unpack in your post, step back examine the stories you're telling yourself. Are they actually real? Is there something more nuanced going on?
If you want a job, start interviewing and prepare yourself or interviews. If you didn't get the job, reflect on your gaps. Maybe you are unhireable (I doubt it), but you need to get data. Some places will dismiss having a ton of 1 year stints, but if you make it to the interview stage your resume matters less.
Plenty of Gov programming jobs in the lower CoL areas.
City of Fresno is hiring a few in the $90-110k range, which goes a heck of a lot further there than in the Bay, while being close enough to hybrid work if you decide to (I have friends there who work at Google, Nvidia, etc. hybrid).
Gov work can be boring, but it's rarely stressful.
First of all congrats:
You actually got "some" success in a startup ... In your twenties... Thereby seeing most of it and getting the regrets out of your system.
These are amazing combinations. Which means you know how to call out the BS when you get approached by Hussle pornos.
Second as a newly 30 year old for perspective if you were to join a faang (or a pre IPO startup) even as a junior, and are willing to stay put, learn corporate speak/politics etc (assuming you want) you actually have a shot at 3-4 promotions in 10 years. Which is really good by the time you get to 40. For context 4 promos gets you to senior staff at Goog/Meta. Again that is really good and 10 years is neither a Hussle or slack.
Do you have a good story that will resonate with hiring managers on why you are making the switch from small to big? Most won’t be excited to hire the guy that pushed hard for years and now “wants to coast”. I’m not saying that’s you, but it can easily come across like that.
May I suggest something else: a lifestyle business? I'm in a similar position but absolutely can't see myself slaving away with bullshit business stuff. I want to be productive but have enough freedom and time to enjoy the (very quick) passing of time. So I'm trying to build a business that supports my life but nothing more. No moonshot, no grand gestures, just something simple worth doing.
There's no way you are a loser. 1 successful exit, flaunt it man. No one cares about the exit value. The fact that you had a successful exit is a huge win. I would say that you can certainly strive for a 250-300K salary in the bay area at least.
You should try Walmart for an IC role. Glacial pace of working and a shit ton of bureaucracy, but looks like it might just be the right environment for you now.
Other companies that I can think of along similar lines - JPM, Cisco, Arista or any of the traditional companies.
Your best bet is to network with the hiring managers. I think if you just meet them and speak about your experiences in an event or something you might be able to articulate your experiences better than just in a resume.
Also I have found that drafting your resume and asking ChatGPT or another LLM to refine the wording really works. These LLMs know the ATS or resume scanning keywords and will tailor your resume accordingly.
Good luck
Spend a few years in big corp, and you will miss working in startups - the grass is always greener on the other side !
What is preventing you from finding such normal job?
I went through a similar phase, and after my previous company was acquired, i very much enjoyed working at a corporation. But the 'startup bug' is a thing and that lasted two years, now I am back at doing a startup and so far still enjoying it (5 years into my startup 2.0 life).
Can you share more about your experience? What type of tech are you experienced with, what industries, etc
140k? What job is that?
> I feel like a freaking loser given my age and my relative career stagnation / my inability to actually turn my mildly above average skills into any real money
I would concentrate on this. Why are you feeling this way? Is it possibly because you compare yourself to others? Or you compare yourself to the "ideal world" that lives in your head based on the things that you read on the internet and experience of others?
I'm sure you have lots of positives in your life right now. Are you starving? Do you have roof over your head? Do you struggle from any health problems or mental diseases? Are you addicted to anything? Do you have friends? Do you spend enough time with them? Can you exercise? Can you pay your bills? Do you have savings to whether turbulent times?
I bet if you switch focus to something that you already have and where you already at it will help you. Switching mindset where you think not from backtracking from Ideal situation back to your life, but to switch that to start thinking from where are you now, and what are the next smallest step that you can take?
Did you make any friends at any previous job? Where are they all now? Referrals and nepotism are the keys to hiring in most places.
I think a good fit for you would be a PE backed software company. More specifically “growth PE,” these are firms that are typically coming in to bootstrapped or founder owned companies and are essentially a wallet for the company to leverage for inorganic and organic growth. I think this fits your background and provides a more stable outlook, specially if you focus on PEs that only invest in profitable companies or low burn companies. They will also be able to provide reasonable compensation
>I'm freaking out because the market is beyond fucked
I’ve noticed that many company execs are turning to AI in order to solve one of their most pressing problems: how to eliminate wages without eliminating production.
Things are going to get _a lot worse_ before they get any better. And that’s assuming that we don’t end up in a neo-feudalistic society where the 0.01% live like kings in unimaginable wealth while the 99.99% live in abject poverty and shackled to jobs like slaves, because if you aren’t profitable to someone you are fit only to die.
"Even shooting around what new college grads are getting would be fine ($120-140k)"
Wait, what ? Other than may be Silicon Valley or NYC (and thats a stretch), where would a new college grad get $120-140K in America ? Where ?
OP, these startups can't offer you a job because they don't have the money to pay you. Plain and simple. Its not related to your skills in any way.
> I feel like between AI and offshoring I might just need to do something else all-together.
Let me address this one upfront, both for you and for the other job seekers out there fretting over the same thing. AI won't replace a competent Engineer anytime soon, and offshoring/outsourcing is a continuous part of any business cycle. While tech companies are very much in the early days of outsourcing and offshoring, non-technical companies are actually at the opposite end - looking to bring talent back in house after years of outsourcing with decreasing satisfaction or results.
It's just a part of the cycle, really, if you're looking to transition into "stable" work. Companies will always be chasing fads that claim to make everything better while also lowering costs, be it AI, some hot new tech hub in a cheaper economy, leveraging MSPs, or just flatly trimming headcount and "increasing velocity". You're gonna have to learn to roll with those rhythms and punches if you want to thrive.
> I feel like a freaking loser given my age and my relative career stagnation / my inability to actually turn my mildly above average skills into any real money.
Imposter syndrome sucks. From my perspective as one of these technical "normies", I'd consider you more successful by simple fact you actually sold a company - not an easy feat! Think of it as just switching to a different "lane", with different expectations; you're not a failure, you're just growing in a different way with different challenges than you're used to.
With all that being said, and without really understanding your specific skills/fields, here's some generalized advice about the "normal" tech world:
First, figure out where you want to work in terms of "vertical", as tech is often divided into "enterprise" or "business" technology (as in, the folks supporting how business gets done), and "product" technology (the folks making and supporting the way the business makes money). Some companies may try to combine the two, but they're often like oil and water in that they don't mix well.
* BizTech is often a slower pace because you generally want people to do work, not figure out how to do work, and so there's a stronger emphasis on stability, reliability, and repeatability.
* Product tech is more fast-paced and focused on solving new problems, building new things, and delivering on roadmaps. This sounds like it might be more directly transferable skills-wise since you're coming from Startup World, but that market is a hot mess right now thanks to Big Tech layoffs and AI hype.
Next, identify where your existing skills fit within that vertical, and rewrite your resume to highlight those capabilities.
* Focus on the specific technical achievements with all the buzzwords you used along the way. Don't pitch stuff like "delivered an app with 10k concurrent users and five-nines uptime on a budget of $X", because most companies don't care about your company. They want relatable achievements, like "Built ArgoCD Pipeline to orchestrate production Kubernetes clusters using GitHub Actions."
* For developers, focus on languages known and share your GitHub. For Infrastructure/Network/Storage/Systems folks, focus on vendor suites and how you stitched products together with automations.
* Two big topics in companies right now are cost discipline and flexibility in hires. Play up both, since you have them from your startup days. Highlight cross-domain shoestring budget deliverables in particular, companies will eat that up as it shows you're both multi-disciplined and cost-conscious.
* Consider some certifications to shore up your bone fides, especially if you're going into BizTech/IT. Those almost always get preferential treatment by employers, at least for interviews.
When you get interviewed, make sure you're asking questions about the company's operations (within reason). This shows you're aware of the requirements of the business world. Stuff like:
* Is there an on-call rotation?
* What's the organization's roadmap over the next two years?
* What challenges are they having? (Which you can hopefully then explain how your skills help them address that challenge)
* For multi-national firms, how do they support their global workforce or customer base? Is it a follow-the-sun model, shift rotations, or something else?
The most important thing to remember is that you're no longer selling a company, you're effectively selling yourself. You need to identify what problems they're facing, and then position yourself as the product to address their ills.
One more thing: leverage your existing network to find some good recruiters, as they can help you get your foot in the door and your resume at the top of the pile. Some recruiters focus on specific industries, while others focus on specific roles.
You can do this! The "normie" technology job market is still forecast for substantial growth globally and domestically over the next decade, especially in Engineering and Architecture. Keep at it, and you'll find your way in due time.
You would be fine with some looking assuming you have common tech stack experience, also do you have a technical degree?
In either case the leet code nonsense is probably unavoidable so worth some time as well.
Have you tried who's hiring and who wants to be hired posts here?
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> I feel like a freaking loser given my age and my relative career stagnation / my inability to actually turn my mildly above average skills into any real money.
There's a lot of noise out there that tells us we're supposed to get rich off of entrepreneurship or VC money, and not enough telling of the truth that those success stories are pretty rare. No one who is doing something they at least minimally enjoy and not breaking their body doing it, and getting paid in the top 20% of income earners, is a loser.