I'm exploring moving away from work with VC-backed B2B SaaS startups and towards working with B2C businesses on Main Street.
For anyone else who's felt inclined to make a similar pivot - any advice? Particularly when it comes to remaining challenged, informed, and translating valuable hype-cycle concepts to people who don't care about hype.
While it's interesting to play with shiny toys, helping investors make money by creating products related to the hype-cycle de jour that get used by other B2B SaaS companies just feels soulless.
(My background is in GTM systems and data analytics mostly, but I think the question applies to anyone)
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.
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.
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.
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.
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 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.
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.
Any advice on taking the best parts of working at VC-backed startups (outside of comp) and applying them to roles on Main Street?
Some or all of those will come as a surprise to the people you are working for.
PTSD flashback of nobody having heard of Redis.
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.
I would love to know how to locate more businesses like that though; I haven't had much luck.
https://www.icare-world.com/us/
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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.)
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.
Going direct to customers without any kind of intermediary is where I start to get really nervous.
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.
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.
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.
I could see that getting pretty frustrating