One fizzled out, the other was acquired in a way I sort of made money.
Recently the market has been a bit of a mess and although I took a break to avoid burnout I'm realizing startups (at least with my level of ability and intelligence) are likely just not a great way to make money.
I'm newly 30 and starting to realize I kind of just want a life and a reasonable tech salary. Nothing insane, just something that could support me in a b-tier city with my own place where I have enough time to actually have a girlfriend and well... a normal life.
I'm freaking out because the market is beyond fucked and it seems like my only real choice if I want to "grow" as an engineer / product guy is founding another company. Fortunately I got into some solid accelerators in the valley with a friend from a few years back. It feels good, but at the same time, I feel old and just want a normal job. Even shooting around what new college grads are getting would be fine ($120-140k). 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.
Last time I interviewed, my litany of previous startups seemed to totally kneecap my chances of getting return callbacks led alone offers. Any advice where I should look next - I feel like between AI and offshoring I might just need to do something else all-together.
Any advice here is appreciated :)
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.
They don't feel like a loser for their entrepreneurship career even if it never netted the retirement money before the age of 30.
https://dqydj.com/income-percentile-calculator/
I’m sure they could find any Enterprise developer job in any major city in the US to do that.
It's always easy to say "I'm doing well compared to a guy sweeping streets for a living" - nothing against sweeping streets for a living.
I don’t earn money to appease my ego.
I barely go out, I don't spend any money on fun things and I do personal upkeep on my nearly 14 year old car.
This advice seems to come significantly from boomers.
I’m not the one struggling trying to find a job…
I’ve done my stint at BigTech.
To be blunt. If you can’t make more than $140K, the market is telling you something. You only “deserve” what the market is willing to pay you.
Because it is your ego. A “modest” life is living at the income level of the 50th percentile - not the 80th percentile.
The minute I brought up $140K you said you felt bad because you wanted to do better than someone else.
I’m not saying be so cynical as to never listen to advice, but carefully consider how the goals of the one giving it align with your own.
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.
Having said that, I've seen teams of fresh grads and bootcamp trained devs, where some 30 year old adult supervision might have saved projects or companies from expensive or existential disasters. "No, we are NOT going to build this critical project's frontend on the JavaScript framework you and two of your bootcamp buddies spent the last 4 weekends writing."
More than anything I think the OP just needs a change of atmosphere and even as an IC with technical management or a middle people manager somewhere stable he’ll have an interesting time with a very different environment.
Any suggestions where I could start to ween my way into this space?
One of the things we do is provide 3rd party opinions on what they might want to hire upon acquisition. Definitely one of the big ones is "senior test engineer". Not tester, but person who builds all the test infrastructure and trains other devs on how to do it properly.
However, times have changed - I want different things in life now. The point of a job is to make money consistently and provide some level of calm. Optimizing for that now since I'm tired of making blind startup bets.
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.
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.
The people who need to be told about the existence of these roles aren't likely to know how to implement your advice, where to go, what to search for, etc.
My only reservation with going this route is technical / programming folks always seem to be second class to anyone else at finance orgs / hedge funds.
The vast majority of software acquisitions are now PE, and the funds we deal with want to see year over year growth (~20%) before selling in about 5 years.
https://www.asimplemodel.com/insights/private-equity-roll-up
I’ve been the technical lead in integrating/consolidating backends while a PE company was doing it.
I literally and purposefully “put myself out of a job”. They had no business trying to hire software developers and I moved them toward using consulting companies and using COTS.
Not independent consultants, signing SOWs where one off customizations were done and managed by consulting companies.
Left there to work for a startup for 3 years. Left the startup to do a stint in in the cloud consulting department at AWS and then was offered a job at the company that acquired the startup that I had worked for previously. I found out that it was also a PE roll up play. They were going to make ne responsible for integrating all of their acquisitions (“staff software architect”). The pay? Only $25K more than I was making as a senior developer before I left the startup and $30K less than I had been making as an L5 (mid level) consultant at AWS.
And after all that, I still ended up at a shitty AWS consulting firm (full time) that was also a PE roll up play and didn’t realize it. I left less than a year later.
My point was not meant to be "you should go work for a PE owned company", but rather that, as someone who sees the companies PEs own, there exists a whole, huge world of software jobs between startups and big public companies, many of which pay very well and are nice jobs. However, these mid-stage private companies aren't making a lot of noise in the tech media and socials, so people don't realize how many they are or even know they exist. They just chug along, making money, growing sustainably, and getting sold every five years from owner to owner. There are many, many of these, and they are concerned with growth – but not crazy ponzi scheme VC bubble growth.
I've seen lots where I was like "when I was an IC dev, I would have worked here in a heartbeat".
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.
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.
My intended direction is somewhere in technical product, but I've really only done it for around a year and frankly I'd need to build a bit of a narrative to be competitive with other product hires.
Ideally I'd like to stay somewhere relatively tech centric because I don't want to go back to uni - but curious where you think I should look?
LinkedIn / some recruiters have yielded a few leads - but again, the market is beyond cooked at the moment.
Understand that just about _everybody_ is doing that.
You should avoid telling lies in applications and interviews, but you should 100% be "spinning" your experience to make it look best for there job you're applying for. You haven't "only done technical product work" for a year, you "spent several years dedicating personal learning time and took advantage of internal company professional development and mentorship, and eventually were promoted to technical product lead".
You'll need references who'll back you up on that, and it needs to be at least "true enough" that if they go and find co workers you didn't put down as references they won't outright contradict it. But most people can push the truth a long way in the direction they want it to lean without it being deceptive or outright lying.
Don't be stressed. You'll eventually find something. You are not a loser. Situation now is now simply not good anywhere.
Grind leetcode and look at examples of the system design interview bengala done to figure out the keywords to hit. It's just a game unfortunately.
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.
I've always sort of struggled putting myself in the shoes of someone who would read my resume and then pick me over another candidate.
Cover letters used to help with this - but I don't think even HR folks read these anymore...
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.
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?
Ideally at least series-B
all in all, within the month prior to joining my friend probably applied to about 50 roles.
Most job markets are “competitive” most of the time.
The tech market is fucked right now. Have you poked around?
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.
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.
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
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).
Last time I lined up 5-6 interviews (after easily 4x applications) only two turned into interviews, one final round that ultimately became a rejection.
I couldn't tell if it wasn't a fit or if I just sucked.
Start sending out an application per day. Eventually you'll find you can do 2 per day, 3 per day, etc.
One day you'll have sent out 100s of applications and get proportionally more interviews (assuming the base rate holds).
For the market, your hit rate sounds good. You don't suck, it's just like that out there at the moment. The fact that you made it to a final round means someone clearly thought you were capable of doing the job.
My best advice is if you have any niche skills try to capitalize on those. Your average Java/.NET/JavaScript developer role is seeing literally thousands of applicants. The more you can get off the beaten path the better. If you know some less common programming language or technology you may well find you have better luck searching for jobs looking for that even if it's not your core competency.
It's just an abnormally bad market right now and companies are passing on good candidates left and right. I highly doubt it's all you.
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?
I don't want to make a million dollars a year - I'd just like a normal 9-5 even 9-7 job that provides enough to live a somewhat normal below average life.
It's insane that in 2025 this is seen as an entitlement or something that shouldn't be relatively common.
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.
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 ?
Also, with inflation $120k is a joke relative to even my adjusted starting salary out of college.
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.
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?
I've had mixed experience with HN who's hiring. Frankly I'd be uninterested in working for anything earlier than a series C startup. I'd frankly rather work for a company with steady and strong revenue and a culture that's sustainable.
Not looking forward to the leetcode nonsense, but it would probably take a few months to get up to speed where I could pass interviews.
Given my resume is sort of all over the place (many 1yr stints) curious of your thoughts on where I should look? I'm tempted to primarily aim for product roles since pure IC roles just make me dread working at this point.
I took a 4 year time out there and now I'm back at a startup. I think what I'm learning now is if I can survive a couple of years and pack my brain with a bunch of new shit I'll be able to get a very nice and chill consulting gig until I retire, if I want that. People want your beautiful and experienced brain and a lot of the shit you potentially have worked on or thought about is more relevant in the current and the future than in your past. A lot of the world is slow AF, you might be ahead.
You can find similar types of roles that those folks I listed above are hiring for within other large companies, sometimes. Some of those large orgs have a small army of consultants and managed services to keep relationships intact when a client decides to try out a different vendor for part of their stack. I spent my time helping clients figure out how to be successful with a competitor to help us keep the existing business we had. It gets weird, but it's out there and I admit I kind of fell into it, but it was because I blindly applied and they were very excited about my past experiences.
Thanks for info, is this part of your challenge? You stated you want a normal job and tech salary, but is it that you really don't want or enjoy coding?
In either case, I'd recommend prioritizing your wants, e.g. location, technologies, role to help you narrow a list of potential places.
The market does suck but there are jobs and with CS degree and some experience I honestly think you'll be just fine. Don't worry about the short stints and just have a reasonable explanation about this if asked.
Not wanting a pure IC role definitely doesn't mean you don't enjoy coding. It usually means you don't want to be stuck building things that are unimportant. When you're working at a company that's making mistakes and you've the experience to know better, it's painful just sitting idly by. I know a lot of people can switch off their care factor, but some of us can't.
For example, I love coding, in the past 3 months I built an unofficial companion app for The Bazaar, an upcoming game. I built a back-end (Next.js, Vercel, Cloudflare, Supabase, PSQL), front-end (React), insight platform, packaged Windows and macOS desktop apps (Electron), reverse engineered the game (C#/Unity) and its networking layer. I was processing 300,000 player events a day.
https://bizarre.gg/runs/00493ccf-5b96-523c-beb4-06e8154cc158 (view on desktop, click on the right)
I was recently forced to shut down this project by the game company (as were other 3rd party devs working on stuff for the game). I was offered a role at the game company, which they reneged on at the last moment.
Perhaps because in my role acceptance email, I wrote about how I am keen to take ownership (in the accountability sense) and get involved with developer advocacy, tech blogs etc. I suspect this spooked them because they "don't hire beyond Senior", which is obviously an absurd practice that's typically put in place by inexperienced/insecure leadership. Typically companies justify this with "we promote within", which is a massive disservice to your staff, because it just means your staff never have access to mentors to help them grow.