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.

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.

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.

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.

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.

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.

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?

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.

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.