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Re:Questions to Ask Before Joining a Startup by jasode on Monday November 26, 2018 @10:17AM (#18533856)
>It is also important to note that early employees experience more dilution events. An example of a dilution event would be raising another round of funding. This is another reason why joining a company early should offer more equity.

I disagree that it's important to note that early employees experience more dilution events. I know you're trying to educate but this type of advice unintentionally misinforms people and causes people to pay attention to the wrong thing. Ultimately, the more important math is number_of_shares multiplied by share_price. As long as that goes up, dilution is not as important. What employees will care about is whether the total money wealth went up and not whether their 5% ownership turned into 4% because a new investment round bought 20% of the company. I have no idea why dilution attracts so much verbiage that's out of proportion to its mathematical importance.

Re:Questions to Ask Before Joining a Startup by PacifyFish on Monday November 26, 2018 @10:46AM (#18534085)
I disagree. The most common way to predict payout is to compare to other companies' exit valuations.

E.g. "Oh, company X got acquired for $250 million. We do something similar. If I own .025% of the company, I'd make $62,500 if we exited at that valuation. Cool."

It's important to be aware of dilution events so that you realize when you accept the offer that your .025% will be more like .008% if you're lucky enough to have a successful exit.

Re:Questions to Ask Before Joining a Startup by jasode on Monday November 26, 2018 @11:05AM (#18534254)
>It's important to be aware of dilution events so that you realize when you accept the offer that your .025% will be more like .008%

But you're repeating the same error of prioritizing the wrong thing: dilution.

What employees ultimately care about is their wealth calculation: shares_multiplied_by_price.

Example of the type of math people actually care about:

  0.008% (because dilutions) a $1 billion company is $80k
  0.025% (no dilution) of a $100 million company is $25k.
People would rather have $80k than $25k. The dilutions that dropped them from 0.025% to 0.008% is irrelevant trivia.

For most employees that are minority shareholders, dilution is a side-effect calculation in the realm of academic trivia. Dilution is not a purposeful strategy in this situation. Highlighting "dilution" in advice for employees in an attempt to make them more financially more sophisticated has the opposite effect!

The scenarios for dilution to be a calculated strategy would be something like a founder considering 2 different offers from potential investors. One VC offers $20 million for 15% of the company. Another offers $30 million for 25% of the company. Or some founders selling too much of a percentage such that the dilution crosses some boundary such as 51% ownership where they collectively lose control of the company. These deliberate decisions around dilution are very different from employees realistically worrying about dilution dropping them from 0.025% to 0.008%!

Re:Questions to Ask Before Joining a Startup by nlh on Monday November 26, 2018 @11:13AM (#18534327)
You’re entirely (technically) correct. The issue is that side-effect often comes into play because employees like to calculate potential future outcomes, and that’s done based only on overall company value (since that’s one of the only data points that’s available from past acquisitions).

I’m sure you get this and I know the psychology of what an employee might hope for shouldn’t be relevant, but unfortunately it is.

(For those who don’t fully get this - what I mean is that folks often look at a potential outcome and say “other companies like this have been acquired for $1-2B vs $100B, so if I’m being given 1% at $10M my stake could be worth $10M!” When in reality after dilution, that stake might only be worth $2M, which is a very different outcome after 5-10 years of hard work at below market salaries.)

Re:Questions to Ask Before Joining a Startup by spookthesunset on Monday November 26, 2018 @03:59PM (#18536749)
What you are saying, I think, is it is important to figure out what the expected future value of each of your shares are. All you have to go on, in general, is "what do companies like this one generally sell for"? From that, assuming all the preferred stock get converted back to common stock, you can figure out what each unit of stock is worth. The problem is, the cap table you have now won't be the cap table you have when the company gets bought out.

It's not dilution that is the problem. Dilution is just what happens when you bring in new money. It's that it is very hard to predict what a reasonable upper bound is for the future value of your shares.

Quite frankly, it is one of the big reasons I think trading salary for stock options is a horrible idea. Much better to treat those options are lotto tickets--the odds they pay out in any meaningful life changing way are very small.

Startups don't like to hear this because the truth is, when you work for a startup you almost always take a sizable hit to your salary.

Re:Questions to Ask Before Joining a Startup by tdumitrescu on Monday November 26, 2018 @01:42PM (#18535725)
Another aspect of this is that if you join an early stage startup and work there 5-10 years without any new equity grants (such as the annual refreshers that many companies give) while the company grows and does new funding rounds, then you're getting screwed badly.
Re:Questions to Ask Before Joining a Startup by jiveturkey on Monday November 26, 2018 @02:26PM (#18536068)
only financially, which isn't one of the reasons you should work for a startup!
Re:Questions to Ask Before Joining a Startup by kakaorka on Monday November 26, 2018 @07:58PM (#18538347)
I think getting paid (preferably well) is always one of the reasons why people work for any company, including startups.
Re:Questions to Ask Before Joining a Startup by robhunter on Monday November 26, 2018 @11:30AM (#18534479)
I also think this downplays the liquidation preferences that come with taking venture money that also brings dilution.

A "billion dollar company" that raised $500M with a 2x liquidation preference will put many fewer dollars into an individual employee's pocket than a $100 million company that only raised $10m.

Re:Questions to Ask Before Joining a Startup by landryraccoon on Monday November 26, 2018 @04:08PM (#18536817)
There’s a gotcha here. The VCs can disproportionally dilute early employees that they think are worth less by issuing new shares/options to founders or new hires.

It’s not true that everyone will always be diluted equally. Someone who isn’t involved in politics or paying attention to investor terms (oh, like an engineer maybe?) is more vulnerable to this.

Re:Questions to Ask Before Joining a Startup by untangle on Tuesday November 27, 2018 @08:00AM (#18541938)
> For most employees that are minority shareholders, dilution is a side-effect calculation in the realm of academic trivia. Dilution is not a purposeful strategy in this situation.

No, your logic would only hold for a public company with shares priced by a liquid market.

For a startup, percent ownership of fully-diluted shares is the key metric. (Other secondary factors, e.g. liquidation preference are also relevant.)

The strike price of the options is derived from the price that the most recent lead investor paid for the last shares purchased. This is not a market price -- the underlying value of the shares is often less.

But the options are effectively worthless until they are vested and a liquidation event, usually an IPO or acquisition, occurs.

Re:Questions to Ask Before Joining a Startup by jasode on Tuesday November 27, 2018 @09:34AM (#18542546)
>, percent ownership of fully-diluted shares is the key metric.

We are talking about different things.

I was talking about "dilution" as a verb/action that describes a _change_ from a starting % of ownership to a lesser % of ownership. The post I responded to was talking about dilution events.

Employees cannot realistically make calculated strategies around dilution _events_ because they are not on the board-of-directors and can't veto the founders to not accept additional round of funding. In any case, whether the employee's shares experience 1, 3, or 4 dilution events is not something people typically care about. What they want to really know is if they get wealthier.

On the other hand, if an employee is offered a # of shares as an incentive to accept a job, then yes, it's good to know if that means 0.10% or 0.05% ownership. It's smart to know if an employee is getting typical equity percentages in the industry that's commensurate with the role and timeline of the startup. (Some examples.[1]) However, that's a metric at a particular point in time and it's not a "dilution event" from the perspective of the employee.

[1] https://www.holloway.com/g/equity-compensation#_there_are_no...

Re:Questions to Ask Before Joining a Startup by JJMcJ on Monday November 26, 2018 @12:03PM (#18534754)
> $80k

Oh, wow! Worked three years of 80 hour weeks and here's 80K.

Re:Questions to Ask Before Joining a Startup by mcv on Tuesday November 27, 2018 @09:20AM (#18542429)
Yeah, considering what I've heard about startup culture, I'd hope such equity payouts are a bit more than this. Anything less than $100k (note, a future expectation, and far from certain) is not worth accepting lower pay or long working hours for.
Re:Questions to Ask Before Joining a Startup by pound on Monday November 26, 2018 @01:55PM (#18535814)
Could you also add two lines: 0.008% of a $100 million company and 0.025% of a $1 billion company?

When you join early stage start-up you know only how much %% of a company is offered to you at the moment, not the future exit value.

Re:Questions to Ask Before Joining a Startup by jasode on Monday November 26, 2018 @02:40PM (#18536174)
>you know only how much %% of a company is offered to you at the moment, not the future exit value.

But this "future exit value" is the same unknown for co-founders, angel investors, VCs, etc. Employees share the same unknown as everyone else as to what the eventual IPO or corporate acquisition valuation could be.

E.g. if an angel investor buys 5% of the company, he only knows his % ownership at that moment and not the eventual IPO price in 7 years. The angel also doesn't know what his eventual dilution will be. It really doesn't matter.

The angels and VCs ultimately cares about shares_times_price and that it has grown multiples of their investment. They already know they will get diluted because every owner gets diluted in the normal course of events. Selling equity to help it become a more valuable company means getting diluted.

E.g. When Accel Partners invested $12 million for 15% equity of Facebook in 2005, their investment got diluted when Microsoft later invested $240 million to buy 1.6% equity in 2007. That's how it mathematically works and it's normal. Dilution is a downstream math calculation side-effect of selling equity. The Accel partners didn't complain that they got screwed and owned less than 15% because the Microsoft investment diluted them. Also, neither Accel nor Microsoft knew what the eventual IPO price would be in 2012.

>how much %% of a company is offered to you at the moment

To be more precise, employees are typically offered a number of shares or options to buy shares instead of an explicit % of ownership. The % of ownership is a derived calculation at a point in time that's based on the number of shares. From that moment on, it's the price of the shares that ultimately matters and not the dilution because everybody's % of ownership will decrease as a normal event in growing companies that raise additional funding. Presumably, the startup hired employees that can contribute value so everybody's share price goes up which more than offsets the dilutive effects of accepting extra investment money.

Re:Questions to Ask Before Joining a Startup by hartator on Monday November 26, 2018 @11:28AM (#18534465)
A dilution event is always bad for the current stockholders. Of course getting investor money is a positive, but it can be a bad deal or the money can’t be wasted just leaving you with less overall ownership.

Don’t also forget you can have down rounds that can lower both your ownership and your share price.

Re:Questions to Ask Before Joining a Startup by angersock on Monday November 26, 2018 @04:05PM (#18536792)
Real talk: most companies aren't gonna exit for $1B.
Re:Questions to Ask Before Joining a Startup by doingmyting on Monday November 26, 2018 @10:51AM (#18534134)
I'm glad you said this. Many got burned including myself due to dilution events. When your 2% stake turns into 0.25% over time and you get paid last, there needs to be a very large buyout/IPO for you to get anything substantial. Add in the taxes paid on that and I would have been 10 times better working a corporate job with less headaches.
Re:Questions to Ask Before Joining a Startup by convolvatron on Monday November 26, 2018 @11:21AM (#18534405)
most companies dont ever reach billion dollar evaluations. say they get sold for a reasonable $100M after 4 years. my 1% stake as a founding engineer should gross me $1M (house money). but since there were 3 rounds I generally end up with car money.

I've been through this several times, and ended up with car money or nothing, and I dont think I'm alone. a warning to fresh grads that they may not end up retiring after spending years of putting in time and a half seems in order.

Re:Questions to Ask Before Joining a Startup by wayne_skylar on Monday November 26, 2018 @12:27PM (#18535018)
This is a great point. I think that on average you're unlikely to recoup the difference in wages in the event that the company is sold. I worked for a startup for four years and got nothing.
Re:Questions to Ask Before Joining a Startup by balls187 on Monday November 26, 2018 @07:15PM (#18538079)
This is far more likely scenario.

To counter this perspective, usually founders take FAR less salary if at all.

Re:Questions to Ask Before Joining a Startup by jartelt on Monday November 26, 2018 @06:02PM (#18537652)
But without those 3 rounds, your company likely wouldn't have gotten to the $100M valuation. Sure, if you can get a company to a $1B exit without raising any funding and avoiding any dilution, that is the best case. But, in reality most companies need to raise capital to grow. You accept dilution because the value of your shares should go up assuming the company is executing well and putting the capital to go use (i.e. increasing the company value).

If the value of your stake goes down, you shouldn't just blame dilution. You should blame the company for performing poorly.

Re:Questions to Ask Before Joining a Startup by zacharycohn on Monday November 26, 2018 @10:18PM (#18539041)
Right, but consider if OP's other option was a Google/Amazon/Apple with total compensation at $250k a year.

They could have worked in a stable environment with guaranteed $1M in compensation after 4 years, vs unstable and very demanding job with a low likelyhood of $1M total compensation over the same time horizon.

Re:Questions to Ask Before Joining a Startup by jartelt on Tuesday November 27, 2018 @10:22AM (#18542943)
Sure, but that is a separate argument. I agree that working at Google/Amazon/Apple probably gives most people the best income over time. The point is that if you work at startups dilution is not your enemy.

Early Uber employees got diluted like crazy, but they will probably do well when they cash out (or already did in secondary offers).

Re:Questions to Ask Before Joining a Startup by ryanmercer on Monday November 26, 2018 @12:20PM (#18534957)
> should gross me $1M (house money).

That's more than my FIRE number haha, real estate in the Bay Area is so silly.

Re:Questions to Ask Before Joining a Startup by nirvdrum on Monday November 26, 2018 @11:07AM (#18534275)
I think your overall point is fair -- you own less, but of a more valuable asset now, so you should come out ahead. However, in my experience the ones that say dilution doesn't matter are often the ones that are likely to be "made whole" at dilution events or have anti-dilution protections. If you're not experiencing dilution the same way that rank-and-file employees are, I think it's a bit disingenuous to tell them that it doesn't matter.

As for its overall importance, most companies simply aren't going to be homeruns. I was at one company that passed on an acquisition offer of $X and opted to take an additional round of funding. A year later, the company sold for the same $X that it passed on. For sure, it was hoping to go much bigger than it ultimately did. But in addition to having to wait for all liquidation preferences to be settled, the employees all got to experience additional dilution for no additional gain.

It's great to shoot for the stars and everyone joining a startup hope that's the outcome. But I don't think it's out of place to also think about the median case. An early stage employee takes a lot of risk with few protections.

Re:Questions to Ask Before Joining a Startup by ummonk on Monday November 26, 2018 @01:49PM (#18535771)
It's important to note dilution events because startups typically pitch their equity based on hypothetical future exit scenarios, without accounting for dilution.
Re:Questions to Ask Before Joining a Startup by habitue on Monday November 26, 2018 @10:54AM (#18534161)
It's not quite as straightforward as you're implying either. If you graph the total value of an employee's shares over time, dilution drops the value of that graph. You can say after the fact "look, after six months your total share value was higher than it started" but it doesn't change the fact that that graph has a big drop somewhere in it. If share price is constantly growing, dilution is always a bad thing for an employee. The pretense that they care about what percentage of the company is owned is specious.

The real reason employees should put up with dilution is because the share price doesn't always grow. Sometimes, the company runs out of steam and it drops to zero. They should put up with dilution because it gives the company a better chance to end up profitable and for their shares to be worth anything at a liquidity event.

Re:Questions to Ask Before Joining a Startup by RcouF1uZ4gsC on Monday November 26, 2018 @11:37AM (#18534537)
You are correct in theory. However, as the shares are not publicly traded share_price is very likely a bs number.
Re:Questions to Ask Before Joining a Startup by SkyPuncher on Monday November 26, 2018 @11:08AM (#18534284)
> I have no idea why dilution attracts so much verbiage that's out of proportion to its mathematical importance.

Emotions.

It's the same reason why many SMB owners get caught up in the 50/50 vs 49/51 split (when there are other, better ways of resolving the voting right aspect) or squabbling over a couple of percent in an investment deal.

Logically, the differences are trivial, are likely to be diluted out anyways, and ultimately matter little compared to other factors.

Emotionally, it feels huge. It "feels" like you're giving something up. On a pizza, "50%" is better than "10%" because it's clearly more of the pizza. Same with many tangible things in life.

Re:Questions to Ask Before Joining a Startup by notfromhere on Monday November 26, 2018 @05:09PM (#18537276)
Because that split is the difference between control
Re:Questions to Ask Before Joining a Startup by foobiekr on Monday November 26, 2018 @05:49PM (#18537577)
preference is, on the other hand, extremely important.