The bigger secret is that stock sold in secondary sales by founders and employees is usually common stock, and the purchasers will often get the right to convert this to preferred stock. This means that the company is instantly encumbered with a greater liquidation preference, without the increase in balance sheet to offset it.

How is that legal and not considered self-dealing and unjust enrichment? If I was a minority common stock owner in a business I assume I would have standing to sue for damages if a majority owner or officer made my position materially worse while enriching themselves in such a manner? Are you sure such a right is typically granted? I mean even the gap between 409A valuations and preferred valuations, as well as a huge amount of precedent, give a different material value to preferred and common stock. Giving that right out of thin air in a sale by an insider is effectively theft from common holders and I have trouble believing what you’re saying as I’m not sure how that could be kosher, if perhaps infrequently litigated. But is it really standard like you make it sound? That would be a very dirty secret and I expect would and should lead to litigation.

Flip it around - it becomes a condition of the deal happening imposed by investors, who themselves are motivated to present the best deal to founders, and to have founders less economically stressed. No secondaries - no deal, and that doesn’t help anyone.

IANAL, but if you only have options, and not stock, do you still have standing to sue?

Who has the cause of action? The majority shareholders. Who authorized the stock sale? The majority shareholders. Are they really likely to sue the founder for something that the shareholders authorized?

Only in some states would minority shareholders have a cause of action. So there are some states in which the courts agree with you. As you might imagine, startups do not typically incorporate in those states.

It is very common and usually a condition of closing. Investors know that preferred is way better than common. They are buying highly speculative assets and want strong downside protection.

> How is that legal and not considered self-dealing and unjust enrichment?

because, ultimately, Capital writes the rules, and they chose to allow this

I used Founders Preferred shares to get liquidity at the A (for a now defunct startup).

In our case, we offered all vested employees the option of selling in the same round on the same terms.

I personally don’t recall any disclosure requirements at 10 people; however, we didn’t have that many participate so perhaps it didn’t apply.

In general, Founders Preferred does layer on the preference stack but also hopefully by a relatively trivial amount to the overall funding size.

Yes, as I mentioned it only applies when you have 10 sellers.

Founders never have preferred shares, at least not the same class of preferred (with the same preferences) as investors.

Not never. E.g. all the capital we as founders put in the business before we raised our seed round was converted into Series Seed Preferred shares at the same rights as angels / seed VC. Small portion of total equity but still.

Founder Preferred is a special class of stock that can convert into Preferred when sold. It’s different from Common as it doesn’t affect the 409A. IANAL.

Where would the stress come from? You get a paycheck and there is no personal downside except opportunity cost (and perhaps reputation). You don’t lose any money if your startup fails.

A lot of people (esp people that performed extremely well in school and in corporate environment) find "failing" and "losing reputation" very stressful.

I guess harden the fuck up?

Exactly. Or just don't do it.

I am sure enough that I would crumble under that specific kind of pressure that I don't put myself in situations where I would experience that specific kind of pressure. Works great!

Thank God someone said this. Of course it is stressfull, there is no free lunch. If you can't take the heat just dont enter into a such top-heavy game.

Harden The Fuck Up should have been the YC motto as really that's the whole program in a nutshell. Now take a glance at any thread here that is vaguely political.

In a big way there has never been a better time to start companies. It isn't the economy you need to outrun, just the competition.

And change.

Landlords and supermarkets dgaf. There is no real risk, and if they stress over it, that’s more a founder’s own psychological failing than anything else.

If you care what other people think that much, you probably don’t have sufficient quantities of the oft-cited “grit” that founders supposedly require.

I think if the idea of your company failing doesn’t cause you at least some stress then you probably shouldn’t be running a company?

Maybe risky ventures aren't for them.

Many high performers have perfectionist tendencies

I think for a lot of founders, there is significant financial cost or opportunity cost upfront. Especially if you are bootstrapping.

Starting a company myself, I took 6 months with no salary. After we raised, my salary was massively cut from where it was (30-40% of what I made the year prior). Then you have the fact I gave up guaranteed raises & promotions (to the tune of hundreds of thousands in RSUs).

There’s a pretty large risk to family security. By year two of the startup I have made 15-20% the cash I could have made elsewhere. I have stock that I trust will be worth more in the future (so imo worth it). However, I can see liquidity events being useful if you’re tight on cash after that run

Investors do it so that the founder can better focus on increasing the value of the company. Having financial stress on top of everything else reduces the probability of liquidity events.

cause if you fail you have to let people go

cause if you fail you have to tell your investors you lost money

cause if you fail is a thought that’s always running through your head as you live it

This is not a real risk you're talking about, but small inconveniences. A risk is losing your house for example, or losing the ability to rent.

Inconveniences are part of life anyway. Being the first engineer means you get all these inconveniences (tell your wife and your kids) plus real risks as above (taking a loan to buy the options and losing it)

“Letting people go” is taking on the risk of all of those people being let go losing the ability to rent or pay their mortgages. That seems like more than an inconvenience to me if you take one of the responsibilities of being an employer at all seriously.

No employee should join a startup with the expectation that the company will be around forever.

Compare startups to restaurants- their failure rate is absolutely massive. Working for a new company is simply always a risk for everyone involved, there's no getting around that.

If you are working a tech job and know how to program computers and have no savings slash the loss of a job costs you your house, you have deep and fundamental problems far beyond the loss of one job and it isn’t your former employer’s fault that your life is mismanaged.

far easier for me to layoff people at megacorp then when your the founder

at megacorp, you shrug and look them in the eye and they know you can’t do much

your in the same boat

as a founder every layoff is YOUR failure

My primary motivation as an employee of a startup is fear of personal financial ruin. That the company won't be able to make payroll and I won't be able to pay my rent, that I'll be evicted eventually or that if the company goes under I won't be able to find a new job. There is no mission or any other soft carrot that I care about. I also don't have any faith in stock options.

I can't imagine caring about reputational damage with rich people unless that reputation is in service of not starving in the streets.

Perhaps you shouldn’t be working in a startup because your lifestyle is unaffordable, or your company is paying you peanuts.

I have worked in startups in Silicon Valley and have had many friends working for them. Most startups pay a base salary of around 200k$ I reckon (for new grads, perhaps 150k). This might come down to 9-10k after taxes per month. A good 2 bedroom house to rent in a location like San Jose would be 3k$ per month, which leaves you 6k for other expenses. Assuming 1k for car, you should still have 5k in savings per month, in a year of working you will have saved up 20 months of rent, maybe 12 months of living without a job. I find it hard to believe anyone in SV startups, is in risk of “personal financial ruin”, or “starving in the streets” just because they lost a few months of paychecks while searching for another job. That may be true in another country, in another market, but all tech workers in the Bay Area are living well above subsistence and acting like they are living paycheck to paycheck is a fantasy. There is a cost to working in startups, and it is an opportunity cost of not working in a big tech company and cashing out your 200k+ RSU over 4 years and instead receiving paper money stock options that can be worth 0.

I don't live in California, the startup I work for is remote. I don't fear financial ruin because I don't have money, I fear it because I catastrophize everything. There's no evidence to suggest I would be homeless if I lost my job, but that's just where my brain goes.

But I'd like to point out that in your math, you calculated the cost of a car and a rent, but no other living expenses. Also in what universe does a car cost $1000/month??

"cause if you fail you have to let people go"

This isn't the founder's risk. It's the employee's risk. And it has the added bonus of, if there is a liquidity event, the employee's don't get the upside.

I was like engineer #3 at a company that eventually was acquired for ~$250MM. My payout was $60,000, after 5 years of employment there. I could have made more by going and contracting at megacorp for a single year. There was never any upside for me.

> There was never any upside for me.

That was because you negotiated and accepted a shitty deal. Unless someone scammed you into believing something that isnt' true, which I doubt. Founders can be overly optimistic, but it isn't same as scamming.

Startups are a difficult game. Everyone gotta watch for themselves. Don't blame on others if you accepted a suckers deal.

laying off people who joined you on your dream is highly unpleasant

financially you are correct, but being a leader is mostly about the human stuff

I tend to have large stress in startups, more than in established companies. I won't get into some of the occasional toxic-element sources that can happen anywhere, but some reasons that happen more in startups:

1. Caring about the mission -- the real-world positive impact -- and potentially able to make or break that. Not just taking a shot at making money, for some opportunity cost that I could evaluate quantitatively on a napkin, and walk away from as soon as an option with a higher expected dollars number came along.

2. Livelihoods and investments of time&effort by colleagues hinge to a large degree on decisions I make, ideas I have, and things I have to pull off, and not wanting to let them down. (A bit similar with money investors, but I care more about personal connections, and involvements where it's not just someone buying lots of lottery tickets.)

3. Low "paychecks" for my HCOLA, at that startup and earlier, so personally needing a big win financial exit, and the startup is what I decided to invest my time&energy into. If that fails, it's starting over, and a lot of wading through various startup ickiness to get another good opportunity (or doing FAANG interview BS, and then their promotion-chasing BS).

Hiring, firing, layoffs, making the wrong decisions with limited information and not finding out they were wrong until years later, huge shifts in the tech market around you undermining your business, competitor actions wrecking your business, pressure from investors, pressure from your family to earn more money, uncertainty about whether the business will ever succeed, and an endless list of other things.

> You don’t lose any money if your startup fails.

Except all the money you lost by not having a proper job along the way. Also it’s not uncommon for founders to float the company at early stage until investment is raised, and they don’t always get a refund for this.

Exactly. I quit Google in 2017 to work on a promising start-up idea (generative AI chatbot for coding, a tad early on that one) and ended up raising barely any money, running up massive CC debt to finance cost of living and GPUs, and taking a huge compounding opportunity cost to not continue growing as a FAANG SWE (not to mention missing out on the stock market run with the extra money I didn't have). I spent the last several years paying off that debt instead of buying a house or investing, etc. I'm massively behind in earnings and net worth compared to my colleagues who talk about their future startup idea but never struck out on their own.

But I'm finally debt free and ready to risk my future yet again on another startup.

I mean if you don't care about the company mission (if it's mission based), you don't compare about your employees, your word, you don't care about your time or care that you sold people that you were going to take their money to build something... then yes there might be no "personal" downside.

Though if you don't care about anything in the first place what are you doing trying to build a company?

I often hear about these SEC rules that explain why individual contributors get fucked, as if that's a good excuse. Either the requirements and disclosures should be fulfilled and more than 10 sellers allowed, or the rules should change, or both.

It sounds like they could’ve fulfilled the requirements and had more than 10 sellers but chose not to.

I didn’t comment on whether it was a good reason or not. My comment was just highlighting some of the complexities in what the blog author was hoping to achieve.

> Please let us all know how that's working out for you in 5-10 years. 4 months in and no stress? Must be easy riding from here!

Honestly VC-funded startups seem like a cake walk compared to actually starting a small business. Your biggest challenge is walking into a room full of rich dudes and schmoozing for your pay cheque. If you fail you get acquired and get golden handcuffs.

If you start a real business you can expect to take on debt, and you'll be personally guaranteeing it because nobody cares about equity in your boutique ice cream parlour. Plus a 5-year lease (which you will also personally guarantee).

The most common endgame for a startup is slowly running into the ground until the money runs out and you eventually shut the doors. Failing your way into a happy acquisition isn’t really something to expect as a contingency, I don’t think.

The contingency isn't golden handcuffs its using one of the hundreds of C-level connections you made as a Founder doing sales and networking (and accelerator programs) to get you a cushy gig as a Product Lead, Operations Lead, or similar title with a strong paycheck and immediate authority.

Then use those five years to enjoy the fanciest office equipment VC money can buy. Don't cry because it's over; smile because it happened.

Not that people with VC need defending, but:

Sure, if you magic up a startup with VC funds you suddenly have it easier than a small, bootstrapped business.

Startups almost never start with a round of VC though. There are almost always months or years of the same experience as a bootstrapped business (ie: extreme uncertainty, no money to pay yourself, etc).

Most startups don't manage to raise VC, and most startups that raise VC fail with no acquihire.

Running with VC funds? Oh god, that would be cakewalk compared to even just figuring out how to ensure there's food if you spend money on some necessities for prototype...

> Honestly VC-funded startups seem like a cake walk compared to actually starting a small business.

Make this about any brick/mortar businesses and the stresses multiply by another factor. If they're in a federally regulated biz (compliance) or an insurance dominated state (rates, inspections), then multiply again.

This is a comment about brick and mortar businesses, I literally talked about having to personally guarantee a multi-year lease in the post.

And yes, some businesses are even harder due to regulatory requirements

I don't know why you are trying to make this a me vs them situation. Both situations are difficult in different ways and they are all real businesses.

"Your biggest challenge is walking into a room full of rich dudes and schmoozing for your pay cheque." - Sounds like you are trolling or alternatively incredibly naive.

"If you start a real business you can expect to take on debt". ... Real business? Come on.

No one in this thread is saying starting a business is easy - ice cream business is debt funded because you have a very definitive range of outcomes. Venture funding is completely different animal - failing to see that limits the value of your comment significantly.

> I don't know why you are trying to make this a me vs them situation.

In terms of economic disparity it _is_ very much an us vs them situation.

Consider the optics over the last 20+ years. The middle class and their small businesses have been decimated while former VC funded companies hoover up their futures on Wall Street.

The level of risk involved starting an average small business is much closer to home compared with a startup seeking VC funding. The former can literally lose his shirt, the latter has to settle for a high six figure salary somewhere else.

Failing to see that limits the value of your comment significantly.

This isn't a me vs them. Who is hoovering up the ice cream futures? Different business model, different businesses. Both are difficult. Being a founder of a VC based company is difficult and being a builder of a retail brick and mortar is difficult. It isn't zero sum and both can exist in the same economy trying to make this a Me Vs Them narrative is totally BS.

Making a wedge where there isn't one is disingenuous.

I one time tried to do a normal startup with 20-30 owners all financially liable. There are other challenges tho.

Especially 5 years down the road when you own ~30% of a $100M company - but you know there's a decent chance you'll walk away with very little, if not nothing - while your peers are all making ~$1M per year working 6 hour days at FAANG with a life partner, maybe kids, and a sizable net worth that isn't going away.

Sure, you've got a decent chance to rocket past them in wealth. But they've got everything they really want. You might have foregone your shot at a partner to build a company to mostly profit someone else who did nothing but write you a check. If you do have kids, you'll be old as hell raising them. All you'll have is extra stuff hardly anyone cares about - except maybe you - if you're the type of person chasing down a decimillion net worth.

I hope these people truly enjoy their boats and their third homes in Aspen! It sure is a lot of work to get them.

You’re obviously overstating the FAANG SWE lifestyle.

But beyond that, it’s interesting you picked FAANG SWE and not startup SWE as the basis of your comparison.

The whole premise of the article is that startup employees are often sold a bag of goods about equity and upside that’s simply a terrible deal. Not terrible in the sense that it’s highly risky, but that it doesn’t even come close to compensating for that risk premium. Its sold as FAANG is low risk medium upside but startup SWE is high risks high upside but really its extreme risk and almost no upside because VCs find dozens of ways to carve it out. And people will say startups pay “market” compensation but they almost always mean base salary only, and the equity is such a horrible deal, it’s borderline fraudulent scam on the part of founders to sell startup employees on the equity as a fair deal.

As an aside, when people think SWEs don’t need unions/ professional associations, they think of teachers unions or autoworker unions where pay is standardized on seniority. Instead, we could have something where our lawyers in our camp could review equity terms and we could collectively advocate for things like liquidity deals. That will never ever happen if you only trust the deals the VCs and founders offer.

Let's not forget that FAANG companies were all startups at one point. Early employees at those companies experienced significant upside. Startups can be very high risk, and in rare cases, extreme upside.

This is the “startup myth” that lets the scam perpetuate.

The world has changed. Google IPOed just a few years after it founded. Now Stripe, objectively one of the most successful startups ever, still hasn’t IPOed after 15 years.

Liquidity preference Dilution

Even the F in FAANG had a major movie made about early employees getting shafted by dilution!

FAANG is 5 companies founded a long time ago. Since then VCs have completely rewritten the rules of the game. But they’ll still point to extreme outliers in the old rules. The fairy tale of the Google masseuse has probably cost tens of thousands of engineers millions in compensation.

You need to get things in writing and do the math and startups make it as difficult as possible to do that and then the math never adds up. So they resort to fairy tales.

Many huge private companies, like Stripe, have found ways to provide liquidity to their employees without going public, e.g., through tender offers. Some more recent examples of companies where early employees did very well would be AirBnB, Coinbase and DoorDash.

Early executives at those companies did very well. Early employees did well, but risk-adjusted , not really. I know people who were fairly early at those companies and they own nice SFH in the Bay Area but they're still working as Directors or whatever.

Consider that if you could make 400k (including liquid stock) in compensation at FAANG but you take 180k at the startup, you're basically betting 220k a year on the company. Except unlike any other company you bet 220k on, you won't get a board seat, you won't get access to key metrics, your influence will be dominated by "real" investor's influence.

If your NW is less than 10M, which presumably it is, anyone who's heard even heard of the words "Kelly Criterion" would tell you your nuts for betting 220k a year on one startup. And yet, you get treated like "an employee" and not like "an investor" for taking that insane risk.

So YC has invested in 5000 companies, and you can name 3 that had top-notch outcomes, thats 0.06% success - and you had to work like a dog to realize it! And that money was locked up. Those same early employees could have taken that $220k/ year, put it on Bitcoin or Apple stock, and retired off that. And Bitcoin and Apple were much easier "picks" than an given startup.

The math simply does not add up and the whole system runs off mystique and naivety. And I've worked at startups that gave me a hard time about asking about outstanding shares, about asking about the cap table, about asking about liquidation preference. This is _critical_ information before you invest a significant portion of your life and net worth on a company and that they're guarded about and it should raise the ultimate alarm bells that they don't fall over themselves to explain every part of it.

There's a bunch of propaganda out there "Explaining ISOs, written by a16z" that's a smoke screen of the truth. The math does not add up.

The dream startup employee is really really good at Transformer architectures and really really bad at personal finance. Fortunately for startups, a shocking amount of these people exist. But it doesn't change that if sharp financiers looked at employee equity packages at startups objectively, every single one would agree it's a scam deal.

First of all, we're on the same page about the risk profile of working for larger companies being better for employees. But the reality is there aren't enough of those jobs for every single startup employee out there to get one. Some people also like the startup environment - move fast and break things, etc.

Your denominator (5000) is _all_ investments that YC has made. You need to look at investments of a certain vintage, e.g., 10 years or more. You also need to include all the other companies of that vintage where employees did well (way more companies in that cohort have sold or gone public). The result is 0.06% is a gross understimation of the success rate (where success is defined as successful enough for early employees to make a lot of money).

If you can get that 400k FAANG job, take it, for ducks sake. Not everyone can, and for some of them the startup deal can be quite OK.

People who can get 400k job at FAANG should be smart enough to avoid shitty startups. Looks like they aren't, based on these comments.

Ex ante it's hard to tell what's shitty and what isn't. Remember some VCs also got fooled by it!

> if you could make 400k at FAANG but you take 180k at the startup, you're basically betting 220k a year on the company.

Even worse, your bet is on common shares. Far better to work at FAANG and Angel invest so you get preferential shares.

The biggest scam of VC is that the dollar value of your time is hugely undervalued compared to a $ from VC that gets preferential shares.

> Consider that if you could make 400k (including liquid stock) in compensation at FAANG

I'm very skeptical of the idea that this is common for new hires at FAANGs today. Certainly some people can command that level of comp, but I find it hard to believe the median employee can.

The median employee also isn't the guy who's going to make a killing by being an instrumental early employee at startup. It's apples and oranges. I'd argue that the person who is versatile and productive enough to help build a startup from zero is also in the upper tier of those FAANG employees, and commanding 400k+ per year isn't out of reach.

I personally have taken both paths, and made what I considered a ridiculous amount of money at a startup (after I'd been gone for a while, having bought my stock). When I got my cash out, I didn't quit my not-technically-FAANG-but-pretty-close job and that comp continues to grow. I never expected this, but my comp has grown to the point where the cumulative amount I've made here has actually surpassed the startup money. 7 years at each place, and the steady paycheck eventually outpaced the big windfall. The difference is I can keep the steady paycheck indefinitely, so it's definitely the win if I stick it out. Of course, now I'm itching to do a startup again. :)

I don't agree it's a myth. Is it an extreme risk? Yes, of course. Do people view the risks to be way too low? Yes. But I worked at Cloudflare pre-IPO, got shares at 1.73, and at one point CF was at 200 a share. That was more or less what I was "promised" from the equity.

Stripe is one example of a successful startup not going public, but there are tons of startups that are going public. And there are many startups that wish they could go public, but they simply don't have the finances or business to do so.

I don't think VCs changed much from when Google went public until COVID. We were seeing massive overvaluations of tech companies for years. Once through 2020, VCs got scared and now the landscape is a bit different. But the AI craze has started to get VCs back out of their shells taking bets on risky projects.

So, yeah, idk what I agree with this assessment. At least it's not been my experience in tech over the last 8+ years.

> I don't think VCs changed much from when Google went public until COVID.

VCs changed a ton over that time. In 2004 VCs were still smarting from the dot-com bust. And VCs were hardly spewing cash during and in the aftermath of the GFC of 2007/08. The days of easy VC money were mainly in the early-mid to late '10s.

And as you point out with your end date of COVID, VCs have now backed off again, as they did around 2000 and 2008 during those bust/bear cycles. I would credit interest rate increases with the current backoff, though, not COVID. During early COVID, funding was still fairly well available, assuming your business wasn't something that required in-person contact; even better if your business facilitated home-office work.

> At least it's not been my experience in tech over the last 8+ years.

That's only ~4 years pre-COVID; either seems like too short a horizon to make this sort of assessment. (Source: been in tech for 20-odd years.)

Can you please explain in what way VCs have completely rewritten the rules? Asking genuinely.

The argument that a startup could be the next FAANG is anchored in lottery-like odds.

The expected value of startup equity is far, far, far below a casino. The ON bet at a craps table is 50% odds. Less than 1% of startups survive.

You might as well go to the casino. You will save years of sweat, heartache, and stress-induced mental decline.

Instead at a casino you get to blow your money quickly, enjoy fun, free drinks, and still have the upside potential to become super rich if you are in the 0.000001 luck percentile.

At an early startup, your execution has a meaningful impact on the outcome. This isn’t true for craps. It may be for poker, though.

I think a better analogy would be a poker room than a craps table. You don't get to influence the outcome at a craps table, but your performance at a startup will influence its probability of success. Also your choice of which craps table to play at doesn't change your odds, but you can certainly change your odds of success at a startup by choosing which one to join. Obviously there are no sure things, but after a while you can at least weed out most of the dumb startup ideas and/or the incompetent founders.

This 100%. Really the only reason to work at a startup as an engineer is if you really want to, because everyone pays low and the tiny bit of equity is essentially worthless in 99% of cases, which gives it a very low value.

And, if you exit the company -- either voluntarily or involuntarily -- you often only have 90 days to exercise your options. If you've gotten laid off, eating into your savings while searching for a job is a pretty risky proposition. If you have an appreciable amount of equity, that bill can be rather high. Then there's AMT. Many end up letting the options expire. So, taking that pay cut for equity really didn't work out -- you had less money to exercise the options and because you couldn't, the option portion of your compensation was effectively clawed back.

I very much appreciate the startups pushing to extend the exercise window out to 5 - 10 years, but that's far from the norm. I've debated this with a couple of investors and their stance is if you leave the company then you're not committed enough and shouldn't receive anything. I think that's quite debatable, but that's certainly not the case when folks are laid off. And we commonly discuss people thriving in one particular phase of a company. If you're not in that phase, it's no good for either the company or the employee to continue the relationship just to defer having to exercise options.

The 90 day exercise window is the most obviously broken thing about startup equity in my opinion. We changed this to 5 years at Shogun.

> And, if you exit the company -- either voluntarily or involuntarily -- you often only have 90 days to exercise your options.

This is why I advise everyone that you must early exercise (exercise your option as soon as you start with the company) if you're going to join a startup.

Some startups don't let you early excercise. Run far, far away. Find a different startup. Never join a startup that does not let you early exercise.

> This is why I advise everyone that you must early exercise (exercise your option as soon as you start with the company) if you're going to join a startup.

That's terrible advice, if you present it in an absolutist, blanket way like that. I do wish I early-exercised at my last startup, since I had a nasty AMT bill when I finally did exercise, and I could have had better tax treatment under the small business qualified stock rules when I finally sold. But: a) early exercising my initial grants would have cost me $40k, which would have eaten into my savings to a degree I wasn't comfortable with at the time, and b) I early exercised at two previous startups, which failed, and that ended up being money flushed down the drain to the tune of around $9k.

Sometimes people want to wait a bit to get a better idea of the company's prospects before investing their own money into it. Maybe they want to hold off until the company has revenue, or hits/maintains a particular revenue or growth metric. Sure, if you're a super early employee and have 5-cent options, maybe you'll feel comfortable gambling that money away (but maybe you won't be!). Yes, there will likely be a tax penalty for waiting, but that can be a reasonable and sound financial decision.

I was (fortunately) a few years too young to get mired in the original '00s dot-com bust, but I know several people who were encouraged/pressured to take out loans in order to (early) exercise their startup stock options, and ended up with worthless or underwater stock, but still had to repay those loans. It would have to be a pretty exceptional situation for me to recommend anyone take that route.

(I do agree that a startup not allowing you to early exercise is a red flag, though.)

> Maybe they want to hold off until the company has revenue, or hits/maintains a particular revenue or growth metric.

It is far too late then.

One of the many benefits of doing early exercise is that you exercise the option when the grant price is the same as the current valuation so there is zero profit (and you file an 83(b)).

If you wait too long, your grant might've been at $0.01 but now the valuation is $5.00 (making up numbers but both of these are in the ballpark of my past startup experiences). It is way too late to exercise those options, you'll be paying tax on $4.99 of profit on a stock that you can't sell and might go down! If you waited that long, now you need to keep waiting until there is liquidity so you can do a same day sale.

> take out loans

That would be a terrible idea. Like I said in parallel comments, if the price is too high for your comfort level, don't join that startup.

> I've debated this with a couple of investors and their stance is if you leave the company then you're not committed enough and shouldn't receive anything. I think that's quite debatable

I don't think that's debatable at all; I think it's bullshit. Once your options vest, they are yours. They are compensation for the work you have already done, not the work you will do in the future.

Once/if your company switches to RSU grants from option grants, then at vest day your stock is yours, and can't be taken away when you leave the company (well, I imagine they could write up a contract that says that, but that would be quite non-standard, and I would never work for a company that did something like that). The vested RSUs are, again, compensation for the work you have already done, not the work you will do in the future. I don't see why options and RSUs should be considered differently here.

(I might even stretch that into the idea that it's bullshit that startup options expire at all, even if you stay with the company forever, but I do think that's debatable.)

100%

If equity is going to be a material component of compensation, then the argument "you're not committed enough, you deserve nothing if you leave..." is utter nonsense.

Imho, many/most of these draconian equity / option terms are nothing more than attempts at 'golden handcuffs' to make it more challenging for employees to leave these startups.

Sadly, they work: I know many who couldn't leave roles til they'd saved up for years, or could finally ink second mortgage on their home, etc in order to purchase all their equity in their 90 day post-exit windows....

> high risks high upside but really its extreme risk and almost no upside

Extreme risk? Some startups pay fair salaries.

I don't think startups are that risky (unless you start putting money into them, that is a suckers deal). Or if you work for free, what you naturally should not do. Not everyone can get a FAANG job so it is not very clear alternative.

If you get paid a slightly below market rate and get some worthless equity, what's the big deal? You can always quit any time and change to a corporate career. It is not an end of the world.

that's the thing though. you're not getting paid "slightly below market," you're taking a ~50% paycut to work at a startup vs FAANG

> If you get paid a slightly below market rate and get some worthless equity, what's the big deal?

If you really do, agree that it's ok and a fun ride.

But where are you going to find a startup that pays market rate? Never seen one.

Base salary can be very close! But at an established company you are also making money on RSUs, often more than your salary. And usually have a bonus, which can be quite significant.

So your base salary might be 250K in an established company and 200K at the startup. Not a huge difference. But total comp at the established company is more like 500K-600K vs. at the startup just 200K. Huge difference.

> But where are you going to find a startup that pays market rate? Never seen one.

I guess you're looking in the wrong places. Over the past 13 years, I've worked for five startups (both full-time and contract) that paid market rate (two paid a fair bit above, even). In my professional and social circles, this has been pretty common. Certainly some have worked below market rate for some companies, but that seems to be the exception, not the rule.

> But at an established company you are also making money on RSUs, often more than your salary

That's definitely not been my experience. At established companies, the RSUs are usually a nice quarterly bonus, in the wide range of 10-50% of base (annualized). Certainly there are some where the RSUs can end up being several multiples of base (I've worked at one like that), but I don't think it's that common. A lot of people seem to assert that you can easily get that at a FAANG, but that doesn't seem to be true. Some people can, but not the median employee.

Also consider that a lot of the stories of high equity comp come from people talking about the FAANGs. Consider that those companies were founded 20-25+ years ago, and the "rules" have changed quite a bit over time since then.

> I guess you're looking in the wrong places.

It's possible! I live in the silicon valley bubble.

I've worked for 5 startups (and had offers from about ~5 more to know what they would've paid). None have been close to total comp at a public company.

All of them have been very competitive (or even higher!) on base salary.

But there's no recurring RSUs in a startup (since there is no stock to trade), and rarely bonuses. So total comp is about 30-40% of my total comp when working at public companies.

Extreme risk is driving truck in Iraq or smuggling drugs to Singapore. Working in air conditioned office for double median US salary is not extreme risk by any means.

With that I agree with you that upside is often lower than people expect.

I think we're talking about the risk level when compared to various ways to work at a tech company, not risk level when compared against all possible occupations.

Or, based on examples I've witnessed, 5 years down the road you own 20% of a $1M company because your forecasts were off by an order of magnitude. You've gone through a couple down rounds, where investors took at least 20% each time. You feel obligated to your investors and employees, while there is almost zero chance of walking away with anything.

One thing that is underappreciated in the startup mythos is just closing up shop and trying again.

do investors allow that

They don't control it.

That very much depends on the stage of the company and how much control has been given up at different points. Do you think the management team of a public company could just decide to shut it down? As you raise consecutive rounds, your control is eroded.

One of the greatest quotes I've ever heard from a founder buddy was when his startup was going through a particularly dark moment and struggling: One of the investors said to him "Maybe you should seriously think about shutting down and giving us our money back", to which he replied:

"It's not your money anymore."

Yeah, then the investors call a board meeting and bring in a new CEO to provide adult supervision after a 2/3rds vote. The give that guy more equity than you to keep the ship afloat. "It's not your company anymore."

Your daily reminder of the importance of maintaining board control.

Not realistic to maintain control past A unless you built a real rocketship. The board doesn’t usually want to run your company - they have enough other companies, some evidently better than yours as they don’t require this intervention.

> some evidently better than yours as they don’t require this intervention.

I’m not sure where that’s coming from.

Also plenty of companies out there have control past the A.

Most have voting control, subject to certain investor veto powers, after the A. Very few have it after the B.

Isn’t each round 10-20% to investors? Even in the worst case of Seed, A, and B at 20% each, founders still have 80% -> 64% -> 51% ?

And in the best case it’s just one series A taking ~15%, thus founders still have 85%

It can get much worse. Companies can have multiple “seed” rounds. It may not be doing well enough for a real “A” round. The naming of the rounds doesn’t matter. Valuation at each round does. If your valuation goes lower from one round to the next (“down round”) you’ll give up more equity, diluting everyone else faster.

Each round carves out 10+% for employee options, on top of 10-30+% to investors (Seed can be anywhere from 10-30%, Series A is typically 20% to just the lead, Series B 10%+).

Equity ownership and voting control are also different things. After the B you commonly have 2 investors and an independent director on the board, alongside 1-2 founders.

Can never happen, the guy who says that this ain't ur money no more has made sure that investors know their place on board, they r afterall just passive investors who r spreading risks around, even wework a company that has fucked up financials had to give their founder close to a billion dollars just for stepping down, as long as the founder is a majority stakeholder, he will always remain in control

I'm skeptical. It is rare for founders to maintain majority control past series A. Unless you are very successful, it doesn't happen.

Not VCs then.

Reputation is a thing. You might need investors in your next startup.

If you, the founder, only own 20% of the company, the investors absolutely do control it (absent super-voting shares, anyway). You can propose shutting down the company, but the investors can fire you and bring in a CEO who will keep it going.

Not necessarily true. Most control is exerted at the board level through board director seats. You can have a low % and a majority of board director seats, depending on the leverage you had in each round raised.

>5 years down the road you own 20% of a $1M

What a horrible fate. They only got five years of salary plus 200k extra. I'll include them in my prayers (just kidding, I don't pray).

They also probably worked many 100 hour weeks while they could've earned more and worked a lot less with less stress

That's how risk works. The FAANG employee friends have exactly a 0% chance at a 9-figure outcome. They'll easily be at top decile if they pull a nominal $10M+ post-tax in 20 years.

Except the "$200K" is purely paper, and has an expected value of closer to zero. Remember, common shareholders are the last ones to get paid. Investors have preferences and get paid back first (often with interest.)

Also realize you were probably forced to take a pay cut and have a below average salary due to cost-cutting measures from the board. We'll ignore the non-financial problems, like tons of stress, complaining employees demanding more equity because you couldn't give them raises...

No, it's not a good situation.

>while your peers are all making ~$1M per year working 6 hour days at FAANG

I highly doubt ALL your peers are making that much. And I think the people making $1M per year at FAANG tend to work much more than 6 hour days. You have to be very productive to get $1M per year.

The "Four Yorkeshiremen" sketch by Monty Python always lightens my mood when this kind of bragging comes up.

"Sure, you've got a decent chance to rocket past them in wealth."

I might rephrase that as you have a non-zero chance. Odds are not that high and certainly not decent.

It’s a shame you were forced to take on this burden and not allowed to be a regular engineer like your peers.

Nobody is forced to become a founder. A lot of people are naive to the sheer level of stress involved, and think it’s going to be easier than it actually is. You don’t find out just how stressful it is until you’re already super committed, have raised money, have employees, and there’s no easy way out without screwing a whole bunch of people over.

Founders tend to only talk about the good things happening at their companies, and tech press tends to focus on the successes. These things contribute to more people starting companies.

If you can't stomach screwing people over you shouldn't be a CEO.

This long-running narrative that you have to be a sociopath to be a CEO is false.

> tech press tends to focus on the successes.

On the flip side, though, any regular HN reader has likely seen dozens of accounts written by startup founders whose companies have failed. And there's quite a bit of overlap between the set of HN readers and the set of past, current, and likely-future startup founders.

Yes and optimism bias leads people to believe they won’t experience those negative events. Everyone must believe they are going to do better than the median outcome when they start a company.

> while your peers are all making ~$1M per year working 6 hour days at FAANG

Unless you are a manager, in which case you are working more like 12 hour a day.

I know a red badge director (10-15 years) at Amazon who dipped well below 500k due to the last 4 years of stock prices. Though this recent climb has been great for their morale.

Yeah I feel like successful founders natural ambition and optimism is sort of weaponized against them by the VC industry here. From a VC perspective it's worth playing the odds for moonshots. As a founder though, if you can create a $100M company that you own 30% of, you can probably create a $20M company you own 70% of with a much more realistic and sustainable growth targets.

I can't help but feel this would be better for the founders, the employees and the customers of the company. It just doesn't make as much sense for the investors.

> if you're the type of person chasing down a decimillion net worth.

I will hold the world ransom for.... One Hundred THOUSAND Dollars! <holds pinky to mouth>

> making ~$1M per year working 6 hour days at FAANG

Can you say more on this? I didn't realize FAANG TCO was quite that high. Maybe it's time to swallow some pride and take the adtech money after all...

The average SUCCESSFUL founder is in their earlier 30s. At that point - you should be at least L4 (probably L5) at FAANG. Salaries are about ~$450k at that level and age.

In 5 years, if you work even a fraction of as hard as you need to be a successful founder, you should be L7 - salaries are usually >$800k at that point.

No, it is not like any average slacker straight out of college in 5 years can get to a $1M salary at FAANG. But if you're the type of person that could successfully grow a company to a multi hundred million valuation in 5 years - you can make $1M at FAANG.

>you should be L7

The distribution of the ladder is logarithmic. Most never make L6. L5 is often terminal level IC without any “up or out” obligations. Lots of people spend a long time at L5 and retire.

Those aren't entirely overlapping skills. There are plenty of founders whose attitudes and generalist skill sets make them unhireable in the management ranks of FAANG.

levels.fyi says Google L4 in the Bay Area is 306k total comp on average.

https://www.levels.fyi/companies/google/salaries/software-en...

Yes, people are mixing salaries and total comp in this discussion which is unfortunately both common and misleading. It also depends very heavily on the total economic outlook, if you happened to join Google in the fall 2021 cohort your equity was basically going down for the next 3 years and only recovered just now. To claim the average SWE is getting to $1M with that kind of deal is either engagement farming or pure delusion; it has absolutely nothing to do with the reality of most people.

Big caveats on these numbers:

1. You’ll have to be located in SF or Seattle.

2. Going from L5-L7 is _not_ trivial. It requires a somewhat miraculous combination of being on a productive team with a good boss, a lot of opportunities for showy work and your own gamesmanship around corporate politics.

Is it possible? Sure. But in my short stint at Amazon, I met a lot of people who should have been higher level and were simply not due to missing one of these factors.

> Going from L5-L7 is _not_ trivial

It is trivial compared to growing a company successfully from $10M valuation to $100M valuation + an exit.

[citation needed]

Frankly, many more aspects of trying to grow your career from l5-l7 are out of your hands than they are when you're at a startup.

The vast majority of startup success is luck...

There are literally thousands of people going from L5-L7 at the major tech companies per founder successfully exiting a >$100M company.

Thousands, you say? [source missing]

There are only ~2300 Series C companies.

You're going to need to be this size to have a ~$100M+ exit.

There's about ~5 years between funding Series C and Series D [1].

Only ~55 Series C companies got funding in Q1 [2].

Only ~39 Series D companies got funding in Q1 [1].

You're going to have a MAX of about ~.7 * ~2300 * 1/5 = ~322 successful > $100M VC exits per year.

Ultimately, you really need to IPO to have a successful exit - and there's only ~257 per year total, only ~65% of which are VC = ~167.

~5% of FAANG is L7+ - if you're including Microsoft, Nvidia, AirBNB and all the other companies with FAANG-like pay - you're at >2M employees.

That's ~100k If the average tenure is ~10 years before retirement - you're looking at ~10k per year.

Okay - it's about ~100 per successful exit.

[1] https://carta.com/blog/state-of-private-markets-q3-2023/

[2] https://www.mosaic.tech/saas-startup-funding/series-c

Not saying I disagree with your conclusion, but if the question is about which is more likely from the perspective of an individual considering going either route, there’s also an implicit “given that an attempt was made”. You’re only comparing the absolute occurrence of each type of event rather than the occurrence relative to the number of attempts made.

> 2. Going from L5-L7 ... a lot of opportunities for showy work and your own gamesmanship around corporate politics.

Can you say more about that?

A lot of the FAANG companies (all?) have promotion processes that are basically a combination of both peers and managers strongly pulling for your promotion. It often takes a few years just to end up on people’s radars, and that’s a few years of delivering lots of high visibility work and doing lots of tech talks and other sort of corpo-social tasks to get your name out. In a lot of ways, it’s like you’re constantly applying for a new job.

I meant say more about the gaming the politics part, not so much the showmanship and self-promotion part. Say there are several people who meet the criteria to get promoted, which ones tend to get it and which not, based on which political behavior?

Tends to be the one with more friends. That’s pretty much it. That’s the politicking.

Allies, not friends. In that sort of environment, what sort of things get you allies? other than what you mentioned. For example when you say gaming the process, how to approach reviews?

Allies/friends -- doesn't really matter what you call it. It's people in your corner. There's no gaming that I'm aware of. You just have to hope that you are able to get on peoples' good sides. Usually that works alright in the normal course of being a friendly and contributive coworker, but god forbid you have someone who has a chip on their shoulder about you.

> But if you're the type of person that could successfully grow a company to a multi hundred million valuation in 5 years - you can make $1M at FAANG.

Disagree. Totally different skill sets. Not saying there is no correlation at all, but probably less than one might think.

The average L5 SWE salary at Google in the SF Bay Area is $215,000 [1].

1. https://www.levels.fyi/companies/google/salaries/software-en...

That's base pay. Equity is typically another $100k at least.

You don't start there, but you can get there as you level up. A lot of that would be because the stock on your RSU grants goes up while you work there though. I don't think many SWE have 7 figure targeted comp (highest levels, yes). But plenty get there with refreshers and stock appreciation.

Explain the math on leveling up. Each year, Meta hires more Jrs than there exist L7+'s at the entire company.

Many people top out at a lower level because they don't play corporate politics games or because the L7s aren't moving on, so there's no real room for promotion among the L5s and 6s.

Microsoft in the Ballmer years (early/mid 2000s) had this problem. Promising L65/L66/L67 (probably equiv to L5/6 at AMZN) would leave because the next step was full. All the "partners" were hanging around and not making room for the next gen of leaders.

See levels.fyi. The pay levels for FAANG companies are fairly accurate. But you'd have to be something like L7/E7 level at a Meta/Google to break $1M.

Also note that some comp numbers get heavily inflated by people incorporating stock value increasing between the equity was first issued and the stock actually vested.

> Also note that some comp numbers get heavily inflated by people incorporating stock value increasing between the equity was first issued and the stock actually vested.

Yeah ever since COVID this has really muddied the water, partially both up and down. Depending on the year combined with the type of company (large cap vs growth SaaS vs finance) you can massively swing the same exact "offer comp" into many communicated effective comps.

While the median is much much lower, there are a couple of thousand individual contributor SWEs (non-managers) between Google, Meta and a few other big-ish tech companies who make >$1 million/year (steady state, does not depend upon recent run ups in stock prices), with a couple of hundred of those above $4 million/year even. The risk/reward for joining a startup is very skewed in terms of risk in these cases.

s/deci/deka/

Ok, please argue in good faith here. Maybe 1 or 2 people who aren’t executives are pulling in that kind of money from FAANGs.

If you're CEO at a $100MM company, your peers ARE executives at FAANG

Incorrect. See: https://www.levels.fyi/companies/facebook/salaries/software-...

I was under the impression we were talking about ICs here -- your link shows that an upper-middle IC that you'd expect to be choosing between early startup or FAANG will see something around 450 a year, which tracks much closer to what I'd expect.

You said 1 or 2 people who aren't executives. There's way more than 1-2 E7s at Meta, as an example.

Sir if you live in USA and do not take a dip into the VC money swimming pool, you need you are stupid, because crazy people with stupid ideas routinely get to $100 Million valuations, like no other place on earth.

Its like going to Disney Land and saying "Oh i'll just sit at the coffee shop". Some people are here for the ride. Some people like the 9 to 5. Like you, obviously. Why dont you go start corporate_drone_news.org, this board is for hackers and founders.

I don't mind the shit take, but please don't use underscores in your domains.

Good catch, fixed.

You are completely detached from the real world. Even in super rich countries like the US there are a lot of people without savings, living paycheck to paycheck. Most/all software engineers outside the US can only dream of ever earning that much money. And yet here you are, worrying that you'll end up only slightly richer than people earning ~$1M per year.

>And yet here you are, worrying that you'll end up only slightly richer than people earning ~$1M per year.

onlyrealcuzzo is comparing 2 things:

* Being a founder and working mega hours and having no life (e.g. no spouse or kids) and having a decent chance of losing most of your money as the company fails.

* Working at FAANG and making a lot of money while not having to work too much.

onlyrealcuzzo is saying the second option is better.

I don't think you fully understand the context in which this was written, but you probably should before passing so much judgement.

You're saying joining a startup is going to result in success?

Talk about detached from reality.

A 30k job at a local dev shop in Poland is going to reward you more than most startups in the US.

> there's a decent chance you'll walk away with very little

Well, some founders care about their employees and their idea, and the idea of the start up failing is much more than just money.

Your comment suggests people making 1M in FAANG and somehow a stable job. Did you hear about the thousands of layoffs in recent years?

Yes but that's still better than early employees who share a lot of the stress and responsibility of company building, with at best 10% of the upside, but more likely around 0.1% - 1% of the upside that the founder has.

Yep, don't think it pays to go the middle ground in this case.

There isn't much point sweating for another person's dream, go big with your own startup or rest and vest at FAANG and live life.

> our peers are all making ~$1M per year working 6 hour days at FAANG

I think you overestimate median pay at the FAANGs by quite a lot.

"mostly profit someone else who did nothing but write you a check"

There is quite a bit of work involved in reaching the point where you write a check for a Series A round. Also, the better VCs spend significant time with their portfolio companies.

Correct me if I’m wrong, but my perception of most startups at series A is that they’re not usually more than ten-ish employees, and even then, you’d expect more balanced comp packages for employee number 11+, no?