It is physically impossible to choose a startup like a VC because you cannot diversify your portfolio like they can. VCs can sprinkle (relatively) small amounts of money across dozens or hundreds of startups. If one fails then the impact to the portfolio is negligible. In fact, VCs expect that most of their portfolio probably won't pan out.
Good luck diversifying as an employee. Working part time at even 2 startups is obviously laughable.
If you're in it for the money, working at a startup is probably not for you. It really is akin to gambling. There may seem to be more information available than gambling, but there is so much unknown and hidden information it's damn near impossible to make a 'rational' decision.
That's not to say you should never work at a startup. Startups are often great learning opportunities because you usually have both broad and deep scope of responsibility. There's also often better alignment between management and employees because people tend to be working stuff that is materially relatable to the bottom line. It can also be a career accelerator if the company grows headcount rapidly and you suddenly become a 'senior person'™. YMMV.
Stock options: for concentrating your income and your investments when you're excited and biased.
That said, if a startup is doing something that really turns my gears and I like the company, then I'm absolutely willing to work for less pay in order to be a part of that.
In software instead, that's incredibly common: several of my coworkers (late stage private company) are in mostly for the thrill of working on our technology since we operate in some interesting niche, and I know for a fact they are paid much less than me (30%+), even if they have a bigger impact than me on the company (and they are also older, with more experience!).
It's so common that many times employers use it at their advantage, by preferring people that can be sold purely on the tech rather than the tech AND the market rate for the position.
To me, both the financial aspects and the technical challenges must be absolutely satisfied in order to join a company. Maybe I'm too practical because I'm not a trust fund kid and grew up dirt poor, so I know that in my limited ~20y engineering career (assuming ageism) I need to make enough so that I will be able to retire comfortably, while making sure I work on stuff that stimulates me so I can give my very best.
I know multiple photographers whose passion is landscapes/nature and only grudgingly supplement that income with weddings/portraits.
In other words, teachers are not willingly giving up a portion of the compensation that they could otherwise be making doing the same job somewhere else. In software instead, that happens ("Oh, you work on FOO v2.0, I'll happily take 40% less than what I could otherwise be making doing this job in another company").
I don't know about public defenders, you might have a point there.
It's like how artists/writers/game developers/etc. decide to go into their field even though they know that they could be making much more money in any other field.
Most people eventually have to decide whether they want to make 150k writing CRUD apps or 90k writing algorithms.
Basically, startups are a terrible place to work. I wouldn't recommend them to anybody. However, there are some folks, myself included, that love them.
Tech or IT or whatever you call it tends to happen at a glacial pace in structured organizations. Most IT projects fail. Most folks don't care. They want to come to work, do their thing, potentially excel at their thing, go home at the end of the day, and enjoy their life. At a startup, someone that's eager to contribute can really make a difference. One inspired idea has the potential to really move the needle when it comes to the success of the business.
But for public service, not because there is a 0.1% chance they'll get a lot of money.
Source: married to an md phd, meaning ~half the potential salary is both forgone and that time is used to be in public labs solving cancer. Hours still stink tho and every day is life and death, so aggrieved programmer discussions of hours, burnout, compensation, and ability to own equity come off sounding similar to how bankers do. Clearly real for those living it, but odd from the outside.
Something to consider as well, is that while the salaries might be lower, they are often not that far off from what one would make in their respective industry. So someone working at a biotech startup will probably be making a lot less than a FANNG engineer, but would probably be pretty competitive with their peers in 'BigBiotechCo'.
And the other thing to consider is that engineers, and in particular programmers, tend to be pretty bad negotiators. Its possible that your co-workers would gladly take a 30% raise if they knew they were making that much less. I highly doubt they are 'trust fund kids' (those folks tend to found crappy startups, cause if you are set for life, why would you work for someone else?). And if they are older (as you imply) its also possible they were starting to feel the impacts of ageism in tech, and took a low ball offer as a result. Or perhaps they have saved up enough from previous jobs and just don't care that much if they are maximizing their pay, and are more focused on working on cool things and with non-toxic co-workers!
Yes. My willingness to work for less pay if the work is interesting enough only applies to those sorts of companies. The stereotypical SV-style business has no appeal to me regardless of what sort of work is involved. Been there, done that, learned my lesson!
This applies equally to me.
Here's the thing -- a job that isn't fun and interesting is a job I can't tolerate regardless of how much it pays. Life is too short to suffer on a daily basis.
But I do have a minimum amount of income that I can tolerate as well. I have to earn enough money to live, after all. How much the minimum is depends on the cost of living in my area.
Hence, what I really strive to make now is actually 3-5X my cost of living expenses every year, so I can ensure a decent retirement down the road.
Based on that math, I really can't afford the luxury of taking a job that will just cover my yearly expenses. In my case, I really have to go for jobs where swes make $300-400k/yr, and I live pretty frugally myself (I spend 60k/y post tax in the Bay Area). I don’t think it’s safe to assume software engineering is a career that you can keep up until your 60s, unlike teachers for example, so you have to plan for it.
I’ve seen several people actually employ this logic and justify to themselves a 120k software job at a cool Bay Area startup, because it fully covers their living expenses in the Bay, despite not letting them save even one single dollar for retirement. I think that’s very irresponsible though, and they’re in for a sad surprise when they’ll discover in their late 40s that employers don’t consider them as hireable as they once were, and now they have to drive Uber to not become destitute (not that there’s anything wrong with that, but it’s hardly a great outcome).
I've covered that through savings over the decades. But, honestly, I don't expect that I'll ever retire anyway.
> I plan for a scenario in which I’ll be “forced into obsolescence” in my late 40s due to ageism
That's not inevitable. I'm in my 50s and am in as much demand as I ever have been. The key (at any age) is that you have to keep your skillset up to date.
Not all companies want experienced people, but companies who strongly prefer younger employees do so because they know they can take advantage of them, and so aren't the sorts of companies I'd be willing to work for anyway.
> In my case, I really have to go for jobs where swes make $300-400k/yr.
Yow! You must live in an area with an insane cost of living! If that were me, I'd move to somewhere more reasonable. Software engineering jobs are everywhere.
For startups whose stock has 0 actual value in a market, then yeah stock options are worth nothing.
Restricted Stock Units are cash. They are new shares issued to you with restrictions on exercising them. Once they vest, there is no value in not selling them immediately. The tax consequences are the same if you hold them, and you gain the value of diversification by selling.
The above should tell you something about the calculation you are espousing. Yes, the very risky asset called stock options is much less likely to hold any future value. The risk implied should also tell you that for a rare good pick with lots of well managed influence to the outcome, you can succeed with fantastic gains where you cannot simply by holding public shares.
YMMV. The only way to win the startup lottery is to work very hard to influence the outcome. I can't think of any other lottery like that.
The gains that occur after vest-and-release are capital gains. Capital gains for assets held over a year are much lower than ordinary income rates for most people receiving RSUs. (It's still reasonable advice to diversify in the typical case.)
When RSUs are issued, they typically appreciate in value due to either an increase in share price or a discount or both.
When the RSUs vest, one of 2 things happens: either the number of shares is reduced by a sum equivalent to pay income taxes, or (more rarely) income taxes are paid by the recipient later at tax time. In either case, the shares didn't exist in the recipient's account before that vesting date.
If the shares are sold, those funds can be used to buy other shares if desired. If they are held, they are just normal shares in that company. In either case, they appreciate as capital gains instead of income, starting with the point in time when they were either purchased or vested whichever the case may be.
Your initial comment suggested that you didn't distinguish between the ordinary income and capital gains taxation for the pre and post time periods. It turns out you did understand that distinction, but I didn't glean that from your prior text.
VCs also get far more information about the company and can demand way more control. How many employees of a startup get a board seat, even if you're non-founder employee #1?
Even those diversified portfolios aren't going to have huge returns in most cases.
I think the lesson is that if your value proposition is exchanging your skills and time for money (ie, an employee) you can't parlay that into startup style returns without essentially winning the lottery. If you can pick the next unicorn for employment purposes don't waste your talents on actually being an employee
As an employee though you can contribute your sweat equity on a daily basis, rather than needing to make your contribution upfront. So if you figure out the startup is a scam after day 3 of working there full time, you're free to quit immediately with basically no sunk cost. If investors could drip out their cash on a daily basis then most probably wouldn't put in the work to be fully diversified. So yeah, it's a difference, but I think it's a little overstated if you're just comparing the raw numbers of startups each group has equity in.
What I think is a bigger difference is that employees don't have to worry about IRR. If as an employee it takes you an extra two years to get to liquidity, that makes basically zero material difference in your quality of life. Whereas as a professional investor that can destroy your business. On that basis I think this piece may overstate the value in looking for signal. As an investor, placing your bet on someone who is going to be successful but not for another couple years is basically the same as a loss. But that's not really true as an employee.
RE: your point about IRR, I also don’t fully agree. Yes it’s bad when when you don’t show return for many years as an investor but as someone who was personally waiting for a prior employer to go public I can assure that a difference of a year or two is not ‘zero material difference’ in my quality of life.
I’ll even go further and claim that in tech and especially in start-ups, hiring is deliberately deceptive. As a candidate you are at a severe information asymmetry disadvantage when you have to decide to join, and companies very often manipulate that situation to bait and switch on overqualified candidates, lie about or hide financial details, emphasize the wrong things to create halo bias in your decision making, etc.
Given just how egregiously bad companies are, just in general behavior, I don’t see why it’s surprising or controversial or “a sign” of anything to see a job history with a lot of short stints.
In fact, if a hiring manager or HR staff looks at a resume with short stints as a bad thing, that actually seems more like an indicator that the company is bad. They are thinking, “this person doesn’t patiently swallow company bullshit for keeping up appearances on the resume... they’ll never stick it out in our horribly toxic culture...” and it’s very telling that companies think this way instead of fixing their bullshit and being realistic about candidates needing to hop between jobs when company culture is bad.
As a potential employee, you can see a company wildly succeeding (twitter in 2009, uber in 2012-13, slack, github, etc) and yet they will have <200 employees and their stock options will be granted at a 409a valuation around ~100million. Its a pretty reasonable bet at that point.
You will hit some underperformers/duds (coinbase? bird?), but you will have worthwhile stock options a good chunk of the time.
I think you’ll find that consistently picking unicorns is essentially impossible across a long time frame.
It's arbitrage, not clairvoyance.
Engineers spend a grueling month or two getting onsite offers from maybe 8 companies at the most and one or two offers.
Agree 100%, a very misleading metaphor.
No one can predict with certainty which startups will fail and which won’t. If someone did there would be just one VC firm that grossly outperformed everyone else. The truth is you get the smartest people out there, make the most careful bets you can, and you still lose or break even 9 out of 10 times.
Anyone who is joining an early stage startup primarily to get rich has got their eye on the wrong prize. Join because you like the early stage craziness. Join because you care about the mission. Join to learn. If you want to get rich, work at Fang for 10 years. That’s a lot more certain.
Between my wife and I (both software engineers), we have played this VC startup game 5 times. Never again.
This isn’t really true. The experience you can only get at a startup is learning to work with VCs, the board, early strategic partners and so on. This will be dangled in front of you like a carrot but as a mere employee you will never get meaningful exposure here. Unfortunately, like “dilution”, this is something that founders hope you don’t know so they can exploit you.
With that being said...
All three times, despite considering myself a pretty rational person, I got this strange psychological delusion when joining the startup that it was going to somehow magically make me rich. I think it's probably the "honeymoon" stage of joining any company. Things are awesome! The culture is fast-paced, chaotic, and offers plenty of opportunity! This is a rocket ship! It kind of matches the "what if" feeling of buying a lotto ticket. It's impossible not to imagine what might happen.
I think if I jump back into startupville, my cynicism toward the "get-rich-fast with these private options" will outweigh the bright-eyed, bushy-tailed sensation of my 20s.
Joining a "middle" stage co where you are offered expensive options is the worst, since you've missed out on the early upside and you take on a ton of risk due to cost of exercising.
If there’s one thing I’ve learned after two decades in the industry it’s if you care about earning good money, you can either 1) gamble on the 0.01% chance that you picked the right startup or 2) get on to the Senior Executive track as early as possible. Then it doesn’t matter what company you join because they all pay their executives f-you money.
(I, in my infinite wisdom, traded it down to 25 bps for 15 k$/yr more in salary. Whoops)
Can you narrow 1000 companies down to 20 that have a better than average chance of success? Sure you can! And you should, and you shouldn’t treat the options as worthless.
All it would take i think is for companies to start offering larger stakes to employees, with the other two factors remaining the same, and the math might make it worthwhile. But they won’t do it.
Joining a startup that's overwhelmed with demand for its product - particularly if you can see the usefulness of this product yourself - is usually a good move even at 0.1%. Joining a startup that's still iterating on the product (and maybe has a couple customers but just lost a big one and they have to work really hard to sign the next one) may be a bad move even at 10%, because there's a good chance that equity will be worthless.
The article doesn't really mention it, but a great question to ask any potential employer is "What are your biggest problems right now?" Scaling is a great problem to have, because it indicates lots of demand and has solutions that are relatively well-known in the industry. Customer service is a pretty good one - it shows that the company has customers who care enough to want service, and if the CEO is willing to admit this is a problem it'll probably get fixed. Hiring, code quality, internationalization, testing, service outages, brain-dead tech stack, anything that's specific to the problem domain itself - these are also pretty decent problems to have as long as the CEO is attentive to them. Unhappy customers or staff turnover is a caution - you should dig into this further to see why they're leaving, and if it looks like the problem is solvable. Same with financing - many hot companies run low on cash at various points, and you only need to make sure the company isn't going to die, but if the company loses more money than it makes on each transaction that's a huge red flag. The biggest problems (particularly for an engineer) are anything to do with sales, marketing, partnerships, or "growing the business", because the root cause of this is often that customers don't really want what you're making, and nothing short of a major pivot fixes that.
As a side bonus, asking this question is often a big positive signal for the hiring manager, because it shows you're serious about solving problems rather than just collecting a paycheck.
Joining a BigCo can give $1 million (above startup salary) in 5 years with a very high probability.
The original grant plus all the refreshers would have originally amounted to ~$8M (I was within the first 3 employees), but joining early means that at each and every single round you'll be massively diluted (20%+, and there are many of those from a seed round up to a series D/E), and this is without counting the liquidation preference (which in my case was a good 1X non-participating) and other stuff (e.g. emitting new shares for the newly hired fancy CEO that will help us sell the company, refreshers will have a higher cost basis, ...).
If you join early, expect your relative slice of the pie to shrink by roughly an order of magnitude. In the best case.
nothing is "very very risky" unless you are taking your entire salary in equity. if you are making a competitive base I think you'll survive any misstep choosing the wrong early stage co in the long run.
Another startup offered me 0.1% and a mediocre salary. I had to put the phone on mute while I laughed.
(The startup that offered me the 0.1% didn't have either of these qualities.)
> RSUs [...] evaporate if you leave or are fired from the company. You can not purchase them like stock options.
RSUs do not evaporate. Vested RSUs are yours outright. You cannot purchase them because they are already "purchased".
> So you have to stick around until the company becomes public.
In both cases, the RSU or the stock underlying an option, it is equally worthless until there is a liquidity event.
> Oh they also expire in five years
Companies don't even offer RSUs until they are close to being public. Once you reach a certain threshold of stockholders, you have to report financials. Since this is typically undesirable for private companies, they don't want to jump the gun on issuing RSUs instead of options. If the 5 years does pass without IPO, companies re-issue new grants. (Please: name one company that has actually expired RSUs and what happened)
OTOH most stock option grants expire in 90 days upon termination. This is a real expiry, and actual money out of your pocket (and tax liability) to exercies them, and usually a difficult decision. There are some places doing 10-year expiry but those are still the exception.
> The odds of stock options working out is low, but for RSU's they are much, much lower.
It's the opposite. For a private company, RSUs are much much closer to money in the bank than are options.
Typically companies that offer RSUs have achieved scale (your Ubers and Stripes of the world), so yes the upside is lower, but the "pros" are that it's more obvious to you what the value of the grants are and you don't have any cost to exercise them like with options. These companies know that because they are less liquid vs public cos that candidates are right to discount them, which is why they usually offer more than what you'd otherwise receive from a Google or FB.
When they vest, you either get (1) actual shares, (2) the cash equivalent (I think that option may only be available for publicly traded stock), or (3) at your option, retain the RSU for conversion at a later date.
Unconverted deferred vested RSUs might expire (and vested stock options definitely expire), but—unlike options—there’s almost never a reason not to convert an RSU (deferring for later conversion may make sense, but it's essentially always better to convert before expiration.)
At any rate, it is fairly common to get RSUs in a late-stage private company. Uber was giving out RSUs 4 years ago, I believe, and has reportedly filed for a confidential IPO as of last month.
Thousands of execs doing that around Silicon Valley working through Daversa and other executive recruiters (who themselves get $85K-$100K per executive hire).
I honestly don't know who would buy that, the idea I got by doing some basic due diligence on those deals is that who puts them online thinks "let's see if we can attract some dumb money to give us some liquidity at an insane premium". If you sell things at a fair price (e.g. selling common shares at the preferred price * 0.8, depending on the current stage of the company), investors will want to give you liquidity way before your offer on equityzen gets accepted and pollutes the cap table (I speak from direct experience), so what's left on those crowdsourced platforms is many times overpriced garbage.
For example, as a seed VC there are now about 80 companies at various stages that my fund works with. If someone emails me and says, "I'm a good engineer who wants to join a Series A startup in SF or Oakland that has characteristics X, Y, and Z," there's a good chance I can make a few useful recs.
There's nice incentive alignment here: the VC doesn't get any compensation, they just want their companies and the prospective employee to do well. That means 1) we won't recommend a bad fit to an employee because we want the employee to join and be happy and get their friends to ask us for company recs; 2) we won't recommend a bad fit to a company because we want founders to like us and not feel distracted by us. We're going for quality, not quantity -- and you're welcome to ignore our suggestions. So if you're good at what you do and are looking to join a startup, consider soliciting recs from a few investors with large portfolios.
I wrote a short post about this a few years ago: https://www.codingvc.com/using-investors-to-find-the-ideal-s...
I might regret posting this invite on HN, but if you want to join a startup and want recs, my email is in my blog's header.
smack forehead Yes, what ever could I have been thinking before! Yes, yes, I should only be joining a successful startup, not an average one!
> steep career trajectories, like Jeff Dean, Marissa Mayer or Chris Cox.
Yes yes! New plan: be Jeff Dean!
> Next, you need to evaluate the strength of the team and market
Unfortunately, this is not realistically possible for most non name-brand candidates. The company is not going to entertain the amount of inquiry (due diligence) you would need to pursue.
> Evaluating the relationship between founders is as important as evaluating the founders themselves.
Indeed it is! Good luck getting access to do that ...
This article is just more hyperbole from triplebyte. I wonder how their business is doing ...
> We've already achieved profitablity
But if I may quote from this article:
> one thing we learned at YC was not to be fooled by large absolute numbers. What matters most is the growth rate.
triplebyte, put your money where your mouth is and advertise your top line growth rate, not the fact that you are profitable. When your fee is on the order of $30k per hire and your infra and operating costs are low, I expect you to be profitable.
Getting a sense of founder dynamics can be harder, depending on stage, but it's easy if you're early enough. I interviewed at Dropbox when it was 20 people and it was obvious what roles Drew and Arash played, as an example. At a larger stage this is harder, but you have more public sources of information at that point.
Regarding Triplebyte's profits, you should be asking how fast they're growing.
Finally, we should all be Jeff Dean. :)
So there's a few considerations:
- Have you got some savings, in case it dies suddenly? You need to be able to pay rent until you find another job. Hopefully the startup is located near these other jobs.
- Does it allow you to build on existing experience? If you can claim you're in the same industry, you're not losing much (perceived) seniority by trying your luck for a bit.
- Does it give you an easy promotion? This is probably one of the main things a startup can offer. Just being able to add "Senior" to your name or "Team Lead" a few years before you would in BigCo might be worth it.
- Do you get to work with the tech that you want for your CV? You probably have an idea of what's hot to have on a CV, and a startup is relatively new, so maybe you can direct things that way?
The number of people with these sort of "career trajectories" is vanishingly small. This reminds me of what Phil Greenspan wrote (2006?), mocking the college student's career evaluation process:
"I can't decide if I want to be a scientist like James Watson, a musician like Britney Spears, or an actor like Harrison Ford."
The rest basically failures or zombies that made me no extra money.
Probably a little more lucky than most.
It’s really a bunch of little things that, when seen as off all at once, will trip your spidey sense to jump ship.
If you don't have visibility into that, there are other warnings signs, like various spending cuts. No straight answers to questions about that stuff.
Not providing visibility into the business is also a warning sign, in my opinion.
I've also left companies when they started making pretty weird business bets that I dind't think would pan out.
Seems like a much healthier risk profile unless you ONLY want a huge Google-like unicorn outcome as an early employee.
However I do see a lot of benefits that come with working for a startup. You can voice your opinion and be heard. Pushing code to production on your first day. Owning what you do and being able to make decisions. Creating your own environment in which you can learn and become a better developer.
And, most importantly, startups are more open to remote than BigCo Inc.
Monetary compensation might be less, but freedom has a price. If I'm able to work remotely, I can move to a place that is cheaper to live.
The author may sincerely believe in his own advice, but we should note that he did not, himself, get rich this way.
A dropout from elite UK universities, he founded a startup and exited for a small amount of money. Since then he has worked for Y Combinator, invested, and also founded a few companies.
Taggar has never, himself, been anything like a startup employee. And great for him; he seems extremely talented and maybe that route isn't for him. But his company (TripleByte) profits from directing talented people into these kinds of companies.
Honest question; seems like it's a tougher thing to get access to than for a VC, but maybe I'm wrong.
A large reason not to share things is some info is sensitive, for example the share count is a useful number, while the full cap table with each investor’s pricing, terms, and contact info, and other employee grants, would be sensitive and might be more guarded. Same thing about total revenue versus the customer list.
More traditional advice is to ask about the fully diluted share count, so you can see what percentage the options would be, and of course the vesting schedule and purchase terms. Also I’d also ask about cash or runway, which is related to the ability to survive a rough patch.
I was CEO and founder of a YC funded startup and have some experience hiring at the seed stage. For me personally, I wanted engaged people and asking good questions was a positive sign.
One CEO I recall even laughed when I asked at the interview (that should have been a red flag in retrospect). I later learned he gossiped about how inappropriate it was for a candidate to ask about company financials.
Don't try the same with a small business. You will probably get kicked out.
It's sad that Jeff Dean is the last example the article can give. When evaluating a startup as an investor, I see that while investors get great terms, employees get junk options. So until it changes, I'm just staying with big companies, thank you very much.
Does the work look interesting? Will you learn new things?
Do you like the problem space the startup operates in?
How is the culture? Fit or not?
Will you be happy there?
The asking hard questions is very important. I once interviewed with a startup that just raised $3MM. You pay them a small fee and if your flight gets cancelled they find you a new one for free. I pressed the founder hard on why someone like me would buy that insurance and his answer eventually was for the same reason you buy insurance for your car or house. Once he gave me that answer I knew I'm not going to work there. And this was actually a nice startup with some good people. There are much worse startups with founders who have no clue and god knows how they managed to raise money. One founder once told me he is well connected and one phone call and people write him checks (red flag). Then there are the ones who are really shady and will lie about everything. Be very careful and don't ignore the red flags!
Another important point is that you need to make sure the startup really needs you. In the past I talked with two startups that built their pitch around AI but they had very little knowledge of AI so what they had in mind wasn't really possible and even if it was, the product had millions of other things to succeed before AI was even needed. The problem is that founders sometimes focus too much about their pitch and how to impress investors rather than on their product.
Unless you're a valued, seasoned industry veteran, joining a very early stage startup founded by 20-somethings, would you really be able to access all that the author suggests?
But then, my goal is primarily to do meaningful work on interesting projects. I have little interest in getting rich.
There's another option. You can pick a job that isn't a startup, that makes you hate your life, and phone it in every day just to get by. You save your energy and grind away at night on your own company. I say "company" instead of startup because I don't think venture capital is the right thing to pursue for a single founder doing this.
Just have a goal to build a product that has at least 1000 customers paying $10/mon so you can quit your dayjob. The hatred of your dayjob will fuel your motivation to work at night.
A startup is much riskier than taking this approach. You put in 60 hours a week at a startup and even in the very unlikely scenario it pays off and the startup becomes huge - at most you have a 1% stake and become a millionaire. You become a millionaire way easier working on your own project.
So my philosophy is to get a job you hate - work to build the future you want yourself - never let anyone else exploit you to the point where the only way you become a millionaire is if they become a billionaire.
See Dan Luu's articles about "big company vs startups" and "options versus cash"
For example. If you could bet on a coin flip 100k times at $1 a bet, you might be willing to accept getting paid $1.01 per win. But if you had to bet $100k on a single coin flip, you would likely need the payout to be much greater before you were willing to take the bet.
In the meantime you may have traded your youth for magic beans - putting off things like getting a house, a girlfriend, etc because you are working long hours for sub-market pay. That is the real tragedy.
Just wanted to repeat this for emphasis ;-)
Do you believe prospective employees, often with little experience in the startup world, can do a better job of picking winners than VCs can?
At a bare minimum. Probably more often.
no idea how to assess the size of a company's pockets. maybe one that has a founder who has already had a successful exit. every other attribute of a company is basically fortune telling.
A vast majority of VC funds produce weak or negative returns. And this is after diversifying their fund investment across 10+ start-ups and assuming that 90% are going to be losers compared to putting that money in public equities.
You can't work for 10+ companies at once like a VC can. And even if you could, the odds are still against you. The idea that you'll be able to pick ONE winner at an early stage is, quite frankly hilarious and naive.
The better way to do it is to evaluate a whole pile of them at once, and then to pick the best one that you can find. And you're going to have to do a lot of work to evaluate those options, about as much as though your future depends on it, because it does. If you're not prepared to put in that kind of work then it really is just a lottery, and you're most likely better off to just take a job that pays you roughly what you are worth on the market, in the longer term that + a good savings regime will be a much surer path to some serious cash than buying lottery tickets at an opportunity cost of 300-500K each.