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wdewind

5,454 karma · joined August 11, 2009

Will DeWind

Engineering Manager at Gemini, formerly at Sana, Justworks, Etsy

will . dewind at gmail.com

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wdewind··on What to say when recruiters ask you to name the first number
Kind of depends on your definition of "getting screwed." The venn overlap of companies that are very successful and also screw early employees out of stock options is very small, but sometimes expectations aren't properly set about how options work.

It is difficult to make money as an engineer via early stock options, but it is not impossible and the problems of a. understanding what you're being offered and b. making sure you don't get screwed are fairly tractable imo. The hard part is building a company that makes these things matter. Survivorship bias, n of 1 etc. of course, though.

The main problem with startups is joining as employee 10-500ish/public. That's where you aren't getting good stock offers, no one has heard of your company yet and your salary sucks. The upside is this is a great place to learn as a junior both about engineering and about stock options.

You are right that you need to have a lot of business experience to really understand this stuff too. Dabbling in startups is a good way to spin your tires and get screwed, but if you commit to the industry and go through enough deals you can learn enough to protect yourself.

If anyone is currently considering an offer that includes equity and wants some help thinking about how to value it my contact info is in profile, feel free to reach out.

wdewind··on What to say when recruiters ask you to name the first number
I agree with nearly everything you said except this:

> If the company becomes some run-away success there will be opportunity to get more equity but getting a cash raise in 6 months is infinitely harder I’ve found.

The size of grants you get after a company is deemed a "run away" success (or even just "not going to die in the next year") are literally 3-4 orders of magnitude smaller than the grants you get before then (ie pre 10 employee number).

Based on this I tend to optimize more for equity (I'm young and not super risk averse), and another thing I've done is agree to take a pay cut until after another round is raised, with a pre-negotiated salary adjustment in order to min-max more towards equity.

But I think you've touched on something super important which is that using the ambiguity of the value of the options is a great way to put the ball back in their court.

wdewind··on The Ugly Truth of Ugly Produce
I've been reading you on here for a while and I respect your experience and deep thoughtfulness on these issues so I'm really interested in your opinion on this: what about the other half of the problem? How can we navigate the balance of providing mental health services vs. forced incarceration? I want this to be government funded, but our government has a track record on mental health that literally includes long periods in which "put them on an island" was the official policy for "treating" wide varieties of mentally ill people. What things could we do that would actually make a difference here? Is there any meaningful way to make progress without reducing the freedom of the mentally ill?
wdewind··on HoweyCoins – An educational tool to alert investors to possible fraud
Late reply and IANAL but I don't believe you can actually do a token model where the people buying tokens early on pay less for them than they will be priced at later. Pretty sure that doesn't pass the Howey Test[1] because there is an expectation of profit. And if there isn't an expectation of profit there is little to no incentive to have a token, kickstarter would work.

1. https://consumer.findlaw.com/securities-law/what-is-the-howe...

wdewind··on HoweyCoins – An educational tool to alert investors to possible fraud
What are some examples of ICOs that are not illegal securities offerings?
wdewind··on Everyone Wants to Go Home During Extra Innings, Maybe Even the Umps
I'm very into combat sports and I've seen this argument a lot. It makes no sense to me. Watch some bareknuckle boxing, people are not holding back and just break their hands all the time and knockouts happen much earlier. The newest science on CTE makes it seem like accumulated small damage might actually be worse than periodic large damage, so the only argument in favor of bare knuckle boxing is that you get knocked out so quickly that you don't get a chance to accumulate damage.

8oz gloves seems to be a very reasonable middle ground to me.

wdewind··on How North Korea’s Hackers Became Dangerously Good
> why did the handwriting look like the landlord's and not their own?

TLDR: carbon monoxide is a helluva drug

wdewind··on Want airline food? Take Amtrak
My experiences with ANA have been pretty fantastic. One time I was flying to Japan and the plane were going to get on was hit by lightning as it landed. Apparently the FAA then requires a mandatory rebooting and testing process that takes 6 hours. ANA did three things here that really separated them from other airlines:

1. During the 6 hour wait, despite there being no news, I could walk up to the counter and say "Hey just checking again to see if there's any update?" and every single time, without fail, they were friendly, polite and apologetic for the situation.

2. When we got on board the captain got on the loud speaker and immediately apologized profusely "for our incompetence." The plane was struck by lightning, a literal "act of god" and the captain still apologized to us.

3. When we landed in Tokyo they handed us about $200 in cash to deal with taking a cab since it was much later than expected arrival.

I just can't imagine this kind of treatment from an American airline, even on international flights.

wdewind··on How North Korea’s Hackers Became Dangerously Good
https://np.reddit.com/r/legaladvice/comments/34l7vo/ma_posti...
wdewind··on Why Silicon Valley Shouldn’t Work with the Pentagon
A lot of it, yeah. Look at the physics and funding that came out of the bomb.
wdewind··on Why Silicon Valley Shouldn’t Work with the Pentagon
There's a lot in here I agree with. I am not discounting the private sector's value in bringing state sponsored tech to market. This is huge. But what I am saying is that the state leads. Innovation has not traditionally been led by the private market, and again, the narrative that tech has flown from private markets to the military is just not correct, except maybe I guess when you consider the PAAS market bounded in the last 10 years? It really depends on where you draw your boundaries though: PAAS ultimately sits on 65 years of private sector innovation built on top of...a network created to monitor nuclear silos originally deployed by the military.

> The days where the govt seeded tech in the US are long gone. This is not to say there’s no contribution, but when was the last time someone cared about govt or defense contractor involvement?

The entire self-driving car industry is build on top of DARPA experiments from the 90s.

This is the second time I've recommended this book on HN in as many weeks, but it's really quite good in going into the structure and history of the private market/govt dichotomy: https://www.amazon.com/Doing-Capitalism-Innovation-Economy-S...

wdewind··on Why Silicon Valley Shouldn’t Work with the Pentagon
> But at what cost? How many wars? How many lives lost due to our infatuation with the MIC?

I'm not implying the military industrial complex is good (or bad). I'm simply saying the narrative that silicon valley gave the military smart phones and not vice versa severely misunderstands the way things in that sector happen. To the extent that Silicon Valley works with the military it is because SV effectively is a branch of the military.

> The Pentagon does not have to be the only road to basic research, R&D, etc. What if there were other agencies with the budget (to burn) clout of the DoD?

Is there really a huge difference between Pentagon and DoD when talking about the MID?

wdewind··on Why Silicon Valley Shouldn’t Work with the Pentagon
> Yet we shouldn’t forget that civil-military antagonism and the deep American tradition of distrusting the state have been crucial to the United States’ ability to innovate. There are good reasons why defense-tech giants of the 1960s, ’70s and ’80s like Raytheon and Grumman missed out on such major tech advances as Web protocols, the smartphone, personal computers and various types of encryption — all of which would eventually have great military significance. The biggest reason was that none of these advances were directed at waging war; indeed, many aimed at transcending the power of the state.

This is a fairly cherry picked story to match a narrative that frankly does not really exist. Silicon valley is not a partner of the defense world, it's derivative of it. The vast majority of technological disruption has come from technologies emerging from the state, that are then popularized by Silicon Valley. Most of these came from the space race, and in many ways Silicon Valley is still "behind" the Pentagon.

Web protocols, smartphones, personal computers, encryption etc., all of this came from the military into Silicon Valley, not the other way around.

The Pentagon doesn't need Silicon Valley, it's quite the opposite.

wdewind··on Coinbase acquires Earn.com
> How about the thousands of people who have already sent millions of dollars back home to developing nations where they previously had to rely on western union and their exorbitant commission fees.

Sorry to be that guy but do you have a citation for this? I hear it all the time but it makes no sense to me. Can you explain what happens when people receive the bitcoin? For one thing there are frequently 20% spreads in countries that do not have good ways to export their fiat currency, like India, so bitcoin actually doesn't usually end up being cheaper when you consider conversion costs.

> On the opposite side of the spectrum, for the ultra-wealthy, cryptocurrencies offer the ability to place a portion of one's capital in accounts which are not seizable by any means. This is a significant feature of the technology, and coupled with the level of encryption, already represents a small, yet sizable place in the world banking system.

I don't have a dog in the fight of whether or not this is a Good ThingTM, but a lot of people would call this a bug not a feature.

wdewind··on Coinbase acquires Earn.com
What's the dApp equivalent of the space shuttle?
wdewind··on Coinbase acquires Earn.com
> It's precisely the application of market economics to fields of technology, communication and society that previously were mostly voluntaristic that is one of the main opportunities for blockchains

We don't actually let markets make decisions for the big stuff. Take banking: in fact by a lot of measures it's the most highly regulated industry, and most of the fundamentals (like the interest rates) are not set via markets, but via elected (or sometimes not) officials. We don't actually want market economics to run the vast majority of our systems, which is why we've never built frameworks for it before, not because it's particularly complicated.

> Because until now, you'd have to do it for free.

Why wont specialization of labor take over again, and make it so crypto just turns into a different set of centralized players running the infrastructure with a ton of consumers? What happens when it turns out the vast majority of people don't actually want to be involved in running their own banking infrastructure?

> (whether that's a good thing or not is an interesting discussion that I wish were had more often).

Totally agree, upvoted :)

wdewind··on Coinbase acquires Earn.com
I'm saying the technology is derivative of the economics and politics of our culture, and it is unlikely that this relationship will invert itself. Tons of political science and economic thought has gone into designing systems where behaviors that are beneficial to the network are also economically rewarding, you're basically describing market economics. Nothing about cryptocurrency is novel from a political or economic theory standpoint.
wdewind··on Coinbase acquires Earn.com
The "blockchain is just a database" critique is an application of Conway's Law (https://en.wikipedia.org/wiki/Conway%27s_law). The basic critique is: the problem being solved with the overwhelming majority of blockchain tech seems to be a political, not a technical problem. It's a critique that says the issue with this thing you are fixing isn't actually that the data layer doesn't match the existing political structure, it's that the political structure doesn't actually seem to support a demand for this kind of data layer.

The reason this critique is so prevalent on HN is because a lot of us just watched the last 10 years of the internet go from "that thing that is going to democratize technology and knowledge" to "a centralized management system for privacy invasion." The reason for this seems to be, loosely stated: "no one wants to run their own mail server." Because no one wants to put the effort in to dealing with running an email service, we allow Google, Facebook etc. to run them for us. The reason for this is because our economy is based on specialization of labor: it's by design. I can choose to spend my time running a server, but allowing someone to do it for me is orders of magnitude cheaper due to economies of scale, so unless I have a really strong demand it's probably not going to happen.

The blockchain allows for us the same effect as "running our own email servers," and most of us really don't think it's likely that people are going to want to host their own nodes in the blockchain, because, referring back to Conway's law, there are fundamental political aspects to our culture that do not support this architecture.

wdewind··on Goldman Sachs questions whether curing patients is a sustainable business model
In fact, this is a really common thing we see in the market/government dichotomy: the market doesn't, and shouldn't, have a stomach for long term, high risk plays that could possibly benefit all of society. That's not the point. The government handles those levels of investments on a much longer time scale, allowing the market to exploit the technological platforms made by our government. We see this pattern with the space race, the internet etc.: government does the big heavy lifting in the 20-40 year time frame, then VC and the market comes along and "digests" those changes for the marketplace.

Here is an excellent book that describes this relationship in far greater detail: https://www.amazon.com/Doing-Capitalism-Innovation-Economy-S...

wdewind··on Goodbye ICOs, hello ILPs?
Sure, that's true if you are raising from a few, relatively speaking, large investors, and also only if you care about fundraising as a one time event, instead of funds management as an ongoing process. The entire point of ICOs seems to be to raise from many small investors at once, perhaps skirting, among other things, accredited investor laws.

Even for large companies: say we want to do my crazy invest at the team level idea: I don't really agree it would be simple to operationalize all of that money flow, and I do actually think having a blockchain could help if that is your goal, which is a big if.

I'm not here to hard sell anyone on crypto, but I also am not comfortable with the wholesale dismissal of it either, so I'm definitely hoping a lot of people disagree with me and we can tease some of this stuff out.

wdewind··on Goodbye ICOs, hello ILPs?
> Whatever the structure, it isn't new.

But now maybe it's order of magnitude or two cheaper and so you can do a whole bunch of them where you used to be able to only do a few. Does that change anything? I really don't know, maybe, maybe not. Maybe it makes it practical to break a company up into many many smaller pieces and allow investors to provide more specific investments, or many smaller companies in general, due to greatly reduced legal/operational fees? And maybe that let's you do something cool? Imagine if facebook (or more likely whatever is post facebook) had hundreds of smaller investment vehicles that mapped to teams and projects, and we could all choose not to invest in the privacy invading ones? Or at least had to more explicitly do it?

Sure, it's not philosophically completely novel: structural changes like this fractalize throughout technology and ultimately boil down to "that's just this, but one level of abstraction up," which makes it easy to understand, but doesn't necessarily make it useless. Sure, there's nothing new under the sun, the internet is, after all, just a really fast xerox machine, and we already have libraries.

I don't look at crypto currency and think, "Oh this is obviously the future, fiat currency and banks are bullshit" and I don't even fully buy the argument I made above myself. But when I look at all the criticism to crypto, it looks a helluva a lot like 1993 and "The internet is a fad" all over again. "It's slow, it's shitty, it wont scale, it doesn't solve any real problems for real people, it's better having publishers/banks intermediate this stuff anyway" etc. etc.

We'll see.

wdewind··on Why we still can't stop plagiarism in undergraduate computer science
The same way it's done in kindergartens around the world? They say "write me a story about your family" or "draw your family tree." So ok: "write me a program that is somehow relevant to your life."

Imagine you are teaching someone basic web development. The assignment is "make a webpage that displays some facts about your favorite tv show." Easy.

I can buy that it makes the grading more complicated, but coming up with assignments is not difficult.

wdewind··on Why we still can't stop plagiarism in undergraduate computer science
To build on my snarkniess: it's almost as if the incentives behind research and education aren't nearly as aligned as we think.
wdewind··on Why we still can't stop plagiarism in undergraduate computer science
Totally! I definitely didn't mean to imply this is the Prof/TA's fault. It is the fault of many institutions and systems above them. I meant that TA's shouldn't be responsible for grading 4 sections of 60 students each. The only natural outcome of that is poor education, one facet of which is easily cheatable assignments.

It just seems ridiculous that the thing we are focusing on is that kids are cheating and not that we've made this massive, unscalable, expensive, ineffective education system. We are acting like its the kids who aren't holding up their end of the bargain when they try and cheat it.

wdewind··on Why we still can't stop plagiarism in undergraduate computer science
Here's an idea: why not make the assignments personal enough that you cannot cheat on them?

"But wait, that would require huge amounts of time investment from the professors/TAs"

Yes, it's almost as if paying $65k a year for someone to teach you something should result in that person teaching you that thing instead of just checking in to see if you've learned it on your own.

wdewind··on Ask HN: Who is hiring? (March 2018)
Margin | Mid / Senior full stack / backend software engineer | New York NYC NY | ONSITE http://www.margin.co

Margin is an early stage startup looking for a mid to senior backend or full stack engineer. AWS/ops experience is a major plus, and someone who has worked in DevOps before and wants to make a transition into doing a bit more on the dev side while owning infrastructure would be a great fit. More info here but the position reports to me so feel free to contact me about any questions you may have (info in profile) if you'd like:

https://drive.google.com/file/d/1BcdCb9yJloaEAYuxge__-rG-V68...

wdewind··on Confidential metrics for Snapchat features
Thanks for posting this. I am not bullish on SNAP but I highly encourage people to look at that data here. It is a much less dramatic story than the article, a lot of the data actually looks pretty good and at this point the data is fairly out of date anyway (a full quarter has passed since it was gathered). The one graph that is included in the story, showing that Maps is not being used much, is the only truly negative graph I could find.
wdewind··on So Close
> A strategy could have been "start with a $700 offering at the top of the market and work down," but that's not something they tell you on the way in

This is absolutely the kind of thing you should be asking about and they should be telling you on the way in. As an early stage startup employee you are basically an investor. You should deeply understand how the businesses you are joining are going to work, and if they wont tell you you should consider it a red flag.

wdewind··on WHO to recognize gaming disorder as mental health condition
Hi, FWIW I did not downvote you and don't agree whoever did.

> I looked at those studies. They do not at all address issues like PTSD, personality disorders, trauma and other mental health issues which, for example, would certainly characterize huge numbers of people in the interwar and post-war period. Yet, where as these numbers?

Exactly, we don't have them. But I don't see any measures of any kind of mental health improving, with the exception of teen suicide rates in the early 90s. I do see quite a bit of data going back that shows depression, for instance, getting worse, and specifically comparing post WW2 generations to millenials: https://www.ncbi.nlm.nih.gov/pubmed/2648043

So I repeat my question, how are you so sure things are getting better when there is very little or no data saying that, and a fair amount saying the opposite? Wouldn't you expect depression to also be a symptom of experiencing intense trauma and thus a fairly good proxy for PTSD?

> For several decades economic securiyt has been decreasing in the west causing people to feel less "happy" (ie., to be more often worrying). This has an impact on their mental health, but I'm sceptical it comes close to the impact of the vietnam war. The 20th C. was horrific and a horror for everyone. Any "psychologist" nostalgic for the 20th C. either knows nothing of psychology, nothing of history or both.

So this is exactly why it's important to consider this with data instead of logical models. By all means the events of the early 20th century were so horrific that there should be some fairly obvious measurement of mental health that upticks by the end of the 20th century. But we don't see that anywhere, afaict. So that's what I'm hoping you can provide.

wdewind··on WHO to recognize gaming disorder as mental health condition
Off hand I have no idea, but it's also the severity aspect here that is different. Color blind people do not have problems with executive function, maintaining social relationships, depression etc.
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