Having worked in both startups funded by VC's (or wishing to be), and for businesses not part of that, the primary difference is in the attitude towards boring technology. Main Street is not really any better at seeing through hype cycles than anyone else, but they are less up-to-date on what is currently hyped, and they also are more likely to think that they hired the programmer to make technical decisions, rather than wanting to make those technical decisions themselves. They have other (often equally technical) decisions to concentrate on, in different areas, so they are wanting you to just Make It Work.

The downside is they are unimpressed with refactoring, updating to new versions, and the like. The upside is they are ok with you using boring technology that works, even at times when a VC-backed tech company would insist on something new and overcomplicated.

Also, the pay is ok, but honestly it's not going to be as high as in VC-backed employers.

> Also, the pay is ok, but honestly it's not going to be as high as in VC-backed employers.

This, for me, has always been the deal breaker in moving out of VC-funded tech. Leaving corporate tech jobs is already a big enough hit to TC. Getting out of VC-funded tech very often means a dramatic change in life style. The VC world might be insane, but so is the comp.

It's not just the money. The biggest thing I've notice in my career is that, as a general rule, employers value you (or any resource for that matter) in proportion to how much they pay for you. Often people have the illusion that getting paid $80k a year when you used to make $300k will mean that your employer will recognize that you are a tremendous value. They won't. they'll see you and treat you as a low tier worker that can easily be replaced, has timed breaks and 30 minutes for lunch.

What exactly do you mean?

The only people who make “actual” money at the average startups that exit (acquired or scrapped to PE) are founders, maybe the first 5 hires.

I’ve worked at only one startup. We IPO’d. I did pretty good and I joined a unicorn at like series B. Enough to go a decade figuring out what I want to work on next.

Most of my other friends went to work at other startups. Most of them went bust and they made nothing but their base salary (and a couple of them got screwed on that too).

So unless someone’s working at an actual unicorn like I was it’s really no guarantee.

FWIW I made 8x on my latest shares, and multiples on that on earliest. Some people I know who had been there a few years more than me walked away with many more Ms which ain’t bad for 6-8 years of work.

But that is SUPER lucky. It has sort of ruined my outlook too because I have no interest making 250k base + 200k RSUs, and I have zero interest in most of these current startups that I have a good hunch will not work out. And 400k isn’t that meaningful anymore, I’d rather live off interest or work as a barista if my own startup doesn’t work out.

Most bay area startups pay between 250-350k (not including equity) for senior roles. I know because these were offers I was getting a few months ago. A liquidity event is not required to make substantially more than the average “main st.” dev.

The chance at making FU money is what would be worth it.

It doesn't sound too appealing if its 40-50% more total comp and 100% more work/stress and less time for myself plus random things like losing funding or startup goes bust and can't make payroll, etc.

These are mutually exclusive states, actually.

The "chance at making FU money" and "100% more work/stress" and "losing funding or... goes bust and can't make payroll", that's stuff that happens at startups that are paying _below_ the VC-backed market rate.

Once a company gets money to be paying employees in the third hump of the trimodal distribution of SWE pay, those "exciting" parts are long gone. You're no longer in the running to receive a hilarious amount of money should everything 10-100x, and you're no longer worried about going bust and not making payroll.

Even a pre-series A startup I worked at saw the writing on the wall with 5 months of runway left and switched from trying to get funded to finding an M&A deal. At the very least you can get the team acquired by someone in the expansion phase and get the rare chance to interview as a group and compare notes and have an exec try and negotiate your salary _up_ for once.

By the time a startup is paying VC-backed market rate, the level of stress you have just comes from the usual suspects: management, culture toxicity, etc. some of that you can absorb, some might prompt you to find a new job, just like normal.

There's still a level of "hoo-rah, we're a startup" present of course, but I just consider this a bad attempt to keep the magic of when the company and products were small alive. I let it affect me none.

Might be true most places, but I’m paid 80k and essentially report to no one and do next nothing 10 months of the year with no real supervision or expectation. My employer struggles to find people with my exact stack who doesn’t expect over 100k.

If you follow American football it’s often said the best job on the team is the back-up Quarterback. Because they sit on the bench all year and still get to get a sizable check considering. Pretty much the position I find myself in.

Most (not all) of these jobs don't last -- I have had two, and while they were fun we eventually got bought and everything changed.

Well I’m celebrating my 10th anniversary in April, but it it’s how you play your cards. I just go to meetings keep up with the stack and agree with everything. The developers love me because I will always endorse any decision they make. Product loves me because I’m bailing out projects the seniors won’t touch. If I succeed, Product hero, if i fail well we should have listened to the engineers in the first place.

Congratulations, at 10 years you probably have beaten the odds and will continue making some money off of this for as long as you both shall live.

> Often people have the illusion that getting paid $80k a year when you used to make $300k will mean that your employer will recognize that you are a tremendous value. They won't.

Sounds like the folk wisdom that, by default, employers/clients tend to only value you how much they're paying you.

If they had to pay a lot extra for you, the wisdom goes, they will imagine that you must have been worth it, and will take you more seriously.

If they paid bargain basement price for you, well, I suppose the same psychology applies.

(I was reminded of this folk wisdom last week, by a couple hints in an interview. It's a bit tricky to filter out startup employers who only want midrange commodity skillsets, when you're willing to take a lower salary in exchange for meaningful equity. While many of them are thinking of workers as generic commodities (and necessary evils, to the real stars who are the founders), and valuing these hires based on salary they are willing to entertain.)

If you are solving their problems and they see you are solving their problems it's pretty easy to get a seat at the table IF you are also put together like you used to make $300k (dress upper level, don't be out of shape, be attractive/well groomed, have upper level hobbies, decent car, picture on your desk from vacation in an exotic place, have a tag or higher watch). You might also need to play a little business politics and build up whoever is your champion/boss.

If you are good at figuring out how to solve problems, your issue will be they will want to raise you up back to higher level stress positions, and it can be hard to resist being 'superman' and getting kudos again. Every $80k job I took after burning out I ended up leading a department or being a Director and pilling myself with stress again.

If you are just an $80k worker bee you will be treated like a worker bee. But you don't have to be that.

This was my experience, until a bunch of startups tried to come after the boring business I work for. They’ve since brought in a bunch of new people who brought hype cycles with them, and have pushed out the boring and stable solutions, in favor of more complicated trends that need to be migrated or re-written every couple years.

My job satisfaction has dropped dramatically. I found meaning in the boring stuff. The hyped solutions that will be thrown out in a year feel so meaningless.

This is all to say that not all Main Street businesses will appreciate the boring solutions. And if they do right now, things can and will likely shift at some point.

That's mostly what I've come to expect. One thing I think you added, though, is that there's a greater expectation to be the expert in the room.

Any advice on taking the best parts of working at VC-backed startups (outside of comp) and applying them to roles on Main Street?

Version control! Testing! Deployment with a user-acceptance stage! A commitment to tracking bugs and solving them prior to new features! Talking to end-users after the first roll-out!

Some or all of those will come as a surprise to the people you are working for.

This is all true. It is also my experience that Main Street is willing to let you institute a low-cost solution to any of these, as long as it doesn't require them to do much (which, often, it does not).

> the attitude towards boring technology

PTSD flashback of nobody having heard of Redis.

companies outside the venture ecosystem need a lot more help. This is because they’re a lot harder to help. So, expect a Serenity Prayer situation. There is much less you can change. In return, you’re allowed to be older than 35. I would not say the work life balance is that different. bigger companies have deadlines and crises too. The crises are often worse because the management is looser.

> translating valuable hype-cycle concepts to people who don't care about hype

Consider that people who don't care about hype may already know/understand the hype-cycle concepts and just disagree that they are valuable.

Part of leaving the hype-cycle (particularly because you clocked that it was soulless) is realising that challenge and being informed are not the sole preserve of hype.

My inclination is to look not at 'main street' but more niche things where people do care about the tech involved and care about it being an edge for the product or service, but it's all kind of not a big enough market for the stampeding VC herds to bother with.

I would love to know how to locate more businesses like that though; I haven't had much luck.

Agreed, let me know when you find them.

Years ago I worked for this company - at their office in Padova, Italy - and it was a great experience in terms of the people and tech.

https://www.icare-world.com/us/

Boston is less frothy than SF or NY and there’s a ton of experienced professional grad students at a pivot point in their careers looking for a way to start a business, not just hook a VC with tech and try to growth hack from there. Loads of education, politics, healthcare and biotech folks. You could try hanging out there?

Not a bad idea

And how did you know where I lived? (Interestingly, since 2020 almost all my colleagues have not been in those cities. But they’ve acted like they are still. Particularly the leaders of the companies.)

Ha, no way! I just threw it out since it seems Like it’s what you’re looking for.

I’m sorry, to be more clear, I live in NY. Although have family just outside of Boston.

Good luck getting funded by most Boston VCs. They are 10x more difficult and write 10x smaller checks than California based VCs.

Not every business needs VC.

Ignore hype cycles. Let the hype die down, and use tech when it has proven itself. Your run-of-the-mill business doesn't try to stay on the leading edge. When not working in the "startup" world, it becomes a good guideline that if you need to be challenged and informed and parse the hype in order to use a new tech... then you probably should not use it. Boring tech is stable tech.

"just use postgres" should be tattood on every junior engineer right out of college

I don't really get why Postgres is touted as "boring" technology. It's literally the "exciting" SQL server.

Surely you mean MySQL / MariaDB.

With Postgres I literally have to re-read docs every time there is a major version upgrade because I need to remind myself how to dump the database and re-import it into the new version because it's 2025 and Postgres still hasn't come up with a way to not have you do this.

Run your cluster on Debian. Make a backup. Run pg_upgradecluster. In a week, throw away the backup.

(You should be checking for regressions and behavior changes in your app, too, but you always need to do that. Have a QA database.)

I am talking from an end user of an application point of view.

I have _one_ database, not a cluster. I back it up every day anyway.

You're telling me I have to specifically use Debian, and have a cluster, to get a good experience out of Postgres?

Doesn't sound very boring to me.

First, important point: every Postgres DB is in a cluster.

Second, important point: yes, you should use Debian because Debian has consistently provided the upgrade-in-place experience that PG has lacked until.... just now, actually.

Third point that you didn't ask about: you should learn a little about PG tuning, because on day 1, the config is tuned appropriately for your Sun Ultra 5 workstation.

https://en.wikipedia.org/wiki/Ultra_5/10

(I am slightly exaggerating, but you should investigate anyway.)

Okay, I was not familiar with the Postgres specific terminology.

Just for context, I run Postgres on an OpenBSD host (will probably be FreeBSD in the near future) to back an instance of davical which is a caldav server used by a total of two people.

I will keep tuning in mind if I ever actually use Postgres for anything significant but for now it seems like it would probably be wasted effort.

While I'd agree that Debian is boring, it still seems to me that Postgres isn't, even with this in place upgrade tooling. I still have to remember a specific upgrade command special to Postgres.

Try reading what postgres calls a "cluster" (of databases, not of servers): https://www.postgresql.org/docs/current/creating-cluster.htm...

Running and using MySQL is so much more trouble and limitations, it's not even funny any longer. I for myself have concluded, if I have the choice, I will never again choose MySQL.

pg_upgrade has worked fine for years now, no need for manual dump/restore

https://www.postgresql.org/docs/current/pgupgrade.html

You are right, but it's still a manual step I have to remind myself how to perform every time I upgrade. Thankfully the OpenBSD docs remind me, otherwise I wouldn't remember:

https://www.openbsd.org/faq/upgrade77.html

https://github.com/openbsd/ports/blob/master/databases/postg...

I made a halfway step away from B2B SaaS by getting involved with launching a game on Steam. This is still B2B in many ways, but also exposes you to the advantages of a B2C arrangement.

Going direct to customers without any kind of intermediary is where I start to get really nervous.

How are you defining “B2C businesses on Main Street.”

The reason I’m wondering is because it’s striking how much more financially challenged my Main Street is compared to Vc texh.

I see so much opportunity for a small medium business consultation in the analytics and process space but these companies are like really strapped for money and largely set in their ways in my experience.

In my experience, people are open to solving their problems. It’s just the money is hard making it financially viable so it’s just the big money is just like an order of magnitude smaller.

Another thing I’ve noticed is that I think the general level of sort of like process thinking and data driven decision making in tech is at just like a higher baseline than on Main Street

A lot of my discussions are challenging how to sort of like present the problem in a way that somebody that doesn’t have decades of experience and operations understands.

Another challenge that I face regularly with Main Street companies is just people seem to be happy like they’re not trying to continuously optimize like I’m used to doing coming for a big tech. Even when it’s easy to present like positive ROI opportunities there’s just like a comfort with the way things are done and a lot of people seem just happy governed by their scaling factors in exchange for that that comfort.

TLDR; challenges are financial and mentality.

I define B2C businesses on main street as everything from a regional chain of plumbers to a medical practice with 10 or 15 doctors in one area, to a realtor.

It sounds like you are very much motivated by optimizing processes and profitability, and/or the income that doing so provides you. What I've realized is that in many ways I'm not sufficiently motivated by that. What motivates me is the gratification I get from seeing every day people impacted by my work.

Nothing wrong with that, just different things for different people. In fact, you may be a more "enlightened" being because you can focus on the longer term rewards.

I think you’re right. For many businesses the tech is a background enabler rather than the focus. But if you find the right business and culture and leverage the tech, that’s the sweet spot. Tough to find though…

100% right. Any tips on finding it?

One thing I'm hearing over and over is "focus on impact, not process." Which is something I think is something you're seeing become a growing need in tech as well.

Tough to say without knowing you, but I’d say figure out what you’re good at, what motivates you and look for people you enjoy working with. Maybe that takes you to a certain industry but maybe not.

> Even when it’s easy to present like positive ROI opportunities there’s just like a comfort with the way things are done

I could see that getting pretty frustrating

I quit my job. Its forced me out of the cycle of 'just a bit more' and made change the only option. Is it the smartest move, likely not, but so far I stand by it.

I’m in the process of doing the same. From a dollars and cents perspective not the smartest move, but from a finding value in life seems like quite the right direction.

Any advice on staying informed and challenged? Some of the recent changes and new products in tech are actually quite interesting. When you are on the hype-cycle hamster wheel you’re forced to stay informed about both the hype and the interesting stuff. I feel like it’s quite easy to tune it all out otherwise though.

I've somewhat found the opposite. The cycle I've been in is has had a tight grip on my time and attention that's its been hard to keep up with anything not mission critical. Now I'm backing off, I've got time to get more up to speed.

For keeping challenged long term, I've got a few products I finally have the time to do prototypes for and some chances to work in new areas.

I quit a while ago, now I have issues finding an employer that doesn't have idiotic hiring practices or even anyone who will take a look at my portfolio of projects. I haven't had a single interview in which the interviewer would ask me anything about my projects, let alone seemed to know about them, or even read my website. Hiring is utterly stupid these days.

So maybe one recommendation is to make sure you interview well, if you can, or prepare for some unemployed time.

For me quitting was also the only healthy thing I could do, and I am still glad I did leave that lost place.

Don't become dependent on it in the first place.

You are usually forced to come to this conclusion, if you hadn't already, after your experience with a rug-pull or two.

Forget all of the tech hype cycles and notions of what is outdated, cutting edge frameworks, new exciting languages, what will be replaced by AI, etc.

All that matters now is 1) if your software is straightforward enough to understand and 2) helps drive value for your potential business customers. That’s it. Everything else is just functionally irrelevant.

I once worked for VC backed start-up, I've not been VC backed myself, but I worked for Australia's science and technology research agency, so let's somewhat consider what I worked on was funded, cutting-edge development. Normally too early for VC, and often very shiny thing, or polishing things expected to be shiny in the future.

I've only once worked on main street when I was managing the app for a pizza chain.

One day, sitting in a quarterly planning meeting for the pizza company, they were discussing changes they could make to the app and the comment that stood out in my head was "we forecast this change could help us sell x% more garlic bread".

In my head I thought, "I don't care how much garlic bread we sell...this is not why I'm on the planet".

I know not every mains st. business is selling pizza, and lots of B2B companies, VC backed or not, would not excite me.

You're right, helping investors make money isn't very compelling, and I think B2B, has that kind of focus, but many ventures aren't B2B SaaS.

There is lots going on in health, energy, space, etc. right now. I do expect many of these bubbles will pop, but is there something there that interests you?

I didn't see a contact in your profile, but I'm the founder off https://affectablesleep.com, we're not hiring a GTM person, but I'm currently reaching out to a few people for advice. Drop me a line if you're interested in chatting, and maybe I can help you find your next thing too.

> In my head I thought, "I don't care how much garlic bread we sell...this is not why I'm on the planet".

This is a great analogy, because I feel like "I don't care how we optimized the conversion rate for the ads directing traffic to the website for your new data enrichment tool...this is not why I'm on the planet"

You are right, in many ways its related to the products impact more than it is the source of funding. I have found that oftentimes VC-backed products of all sorts, regardless of their mission, get backed into a corner where founders are focused on an exit over real impact. That the model inherently discourages really caring about your customers.

I had forgotten that when I was raising money for my previous company, there was a great meeting I had with a VC. I thought we were going to raise. At the end he said.

"This was fun. All day long, I have founders pitch me these SaaS companies that have found this tiny arbitrage of a few bucks a month. It's so BORING. But at the end of the meeting, even though I don't care what the product is, I can look at a spreadsheet, and say, the market is X, they're making Y, can grow to Z, and I can make a decision to invest without thinking.

When you're creating a new market, I have to think, and I risk losing money. I like what you're doing, but from an investment perspective, I wouldn't touch you with a 10 foot pole, but it was fun to think about what the future might look like."

The thing is, I really appreciated his reasoning and honesty.

That’s interesting.

While I’ve met tech investors who invest for reasons other than profit, all the ones I can think of do so to empower certain demographics. Never thought about ones who might do so because they are interested in a particular space.

But what are success metrics and OKRs for an investor like that?

Assume every investor is interested in profit, but then secondary, what else are they interested in.

I have a friend who is an African founder, and has really struggled to raise. From their experience, they say the VCs that focus on under-represented founders are often predatory in nature. As a white guy, I can't comment on that.

There are definitely investors who have themes around health, media, environment, etc.

The success metrics are still "how much money can I make from this", but it's also "how many lives can I positively impact".

So I wouldn't put these investors on the opposite end of the spectrum. It's a balance of "if we can help x number of people with Y problem, that's worth Z". VS "If X number will pay us Y, how much money can we make?"

It's a very subtle difference. You're not going to find an investor who says "I want to see Y happen, I don't care about the investment". That's philanthropy.

Main Street sells pizza but VCs sell Ponzi schemes

This!

Ask around on Hackernews. Post on the "Who wants to be hired?" thread at the top of each month. See what the local job scene is like in a city whose major industries are not "tech". Use Craigslist, Indeed, etc. as guides.You will find that they need software and automation in all sorts of industries and many would love to hire someone who'd proven themself in the SV world.

Oh, and uh, get used to boredom. Java and .NET, maybe some Python if you're lucky. If you love Rust, get comfortable loving it on your own time. Most of the world out there runs on time-honored technology that's been proven to work, and what you'll find is... that's not really a bad thing. Knowing you have a stable foundation on which to build lets you focus on the things that matter to your business.

Why not try and work at a actual unicorn startup? One that will probably IPO instead of get acquired where you get jack shit.

90% of startups are shit, but there are some actually good companies out there. I worked at such a company, made a lot of money too when we IPO'd.

Find some that are at series B or so, doing something interesting or new to you, with a good track record beyond just unicorn valuation. Bonus points if the CEO is actually passionate and comes from whatever field they're solving for. AKA not some 23 year old fuck boi.

If they're successful, and the company IPOs at like 10-30x you'll make a good amount of money even if you're employee 500. Enough money to not work for a decade, and you'll be making a lot off interest by then so hopefully you can live a upper-middle class to lower-upper class lifestyle if you do nothing else.

Working outside VC tech is like boomer central critical mass of mediocrity. It is a whole new set of issues (mostly dealing with mid-low tier workers who just cannot work independently or without drama, who will drive you insane if you're an Exceeds Expectations type of person), with little financial upside.