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.
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.
> 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.)
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.
> the attitude towards boring technology
PTSD flashback of nobody having heard of Redis.
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.
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.
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.
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.)
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.
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 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
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.