Anecdata, but I interviewed for a marketing role at a 10-person startup in 2013. I asked questions #1, 2, 4, 5, 6, 7, 8, 9, 12, 13, 15, 16, 17, 18, 19, and 20 - and the company was more than happy to 1) answer immediately, or 2) say "I don't know, but let me find out." I should have asked the other questions (especially the relo package!), but I was young, naive, and not tactful enough to ask tougher questions in a "cooperative" manner.

IMO it's insane to work for a company if they're evasive about the value of your equity (#4-8). That's tantamount to lying about comp. You can usually find out how much they've raised on Crunchbase, and you can napkin-math their burn by eyeballing the team (#9-13; payroll is the dominant expense for most startups). #14 seems like a weird question to ask, but YMMV.

I would take their answer to the product-market fit question with a heaping pinch of salt (what are they going to say, "no"? and PMF means something different to everyone), and listen closely to the "feedback from customers" answer.

This is such a short sighted perspective that it's laughable.

Good management will see that the candidate is thinking about joining the team as a long-term commitment and isn't just making a job change for a pay increase over their last/current role. It shows that candidate is showing up for the same reason the company exists -- to be fairly compensated for services rendered.

A leadership team that laughs at these questions are going to lose long-term, and should be avoided by potential employees and VC alike.

Edit: grammarz

If during the interview and negotiation process, a hiring manager (probably a large equity holder) at a startup company can't give me details regarding their equity, funding, board makeup, business strategy, work environment, competitors, challenges they're facing, and how I fit in to their strategy... why would I bother working with them? There are plenty of startup companies that will give me that information in order to sell me on joining them.

If they aren't serious enough to consider each hire vital enough to put some cards on the table, then I'm not about to waste my time working for them.

Further, there are plenty of non-startup companies I can go make a big paycheck at with 9-5 hours.

I'm on the management side (was CEO CircleCI, now CTO darklang) and we would absolutely answer all these questions. It's a complete red flag for any company that would recruit an employee without telling them what they're actually getting.

It's reasonable to keep the answers to Qs 4, 5, 8, 10, 11, 14 and 15 until later in the hiring process when you're close to an offer, so long as you give directionally-correct answers first.

Personally, I would answer everything except 5 in a first interview (and that's only cause I'd have to look up the exact numbers).

I've worked at two startups in the past. The first startup tanked. When interviewing for the next role, I did ask these questions, but had no luck. Ended up taking an offer with 15% increase over my last role. Two years of work, and I find out that this startup too, is on its way down. Eventually ended up moving to a big company.

I've noticed candidates who have had a bad experience at a previous startup often try to find a circumspect way to ask if we're profitable and if we're going to run out of money. Those are good and fair questions that I'm happy to answer.

I'm sure some companies would demure on some of these if the answers are uncomfortable. I hope not many would laugh!

For an engineering position I suggest candidates also ask if they can review some of the code they'd be working on like a recent pull request.

If you are worried about making rent, then perhaps your evaluation criteria would be different, such as "will this pay the bills, and will I be okay working here for the next 2 years."

It’s true that if you’re not in a role where you have the ability to massively swing revenue for a business, you’re not going to receive the same offers. However, there are tons of opportunities out there beyond tech, people just need to want to go after them.

All that being said, situations are way different for traditional blue collar jobs and I get that. I wish my mom, who does not have a college degree, had the same negotiating power that I do, but she doesn’t. So, I help her out as best I can (she’ll probably live off and on with me for the rest of her life- 20 to 30 years).

Life across the globe comes with spectrums of challenges. While not comparable to lack of potable water, knowing the right questions to ask in a startup interview is still a challenge none the less.

A large company with a senior level hire will have amazing relocation benefits.

Friend had one at director level, everything was taken care of.

At worker bee level, you're right, you might get two nights at a motel if you're lucky.

Companies looking to recruit and retain specific talent got creative with compensation packages in attempt to keep wages close to market.

I first heard of this during the dot-com boom in the 90's. Companies were paying "huge" signing bonuses.

Sadly I graduated after the burst, but after 9/11, and went into the defense industry. No signing bonuses, but did have a good relocation package.

I'm from EU, and worked for NA companies, and got most of that covered.

Being quite senior now, I'd feel comfortable asking:

1 - To see their CI dashboard

2 - To see a sample of their production systems stdout & stderr

3 - Asking to review a recent non-trivial commit (with the person/people who wrote it)

4 - If you're interviewing remotely for an on-site position, finding out if they have an open office

5 - Finding out how they do deploys / devops

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.

I want to emphasize one point. A company may offer you options, or restricted stock units, or any sort of equity in the company.

When they do this, they are asking you to invest in the company. They are asking you to buy your shares with your scarcest resource: time.

Do NOT be the slightest bit embarrassed to ask any question you want about the company's capital situation, funding prospects, premoney valuation at the last funding round, amount of "runway" left before they need revenue or another round of funding, names of major shareholders, preferred shares outstanding, etc.

Warren Buffett would ask lots of questions if they asked him to invest; so should you. Mr. Buffett probably would ask better questions, but that's OK. The company should encourage questions from YOU: they're asking YOU to invest.

If they bristle at your questions, it's a red flag. They may say, "look, that's confidential, can't answer specifically," and that's OK. But they shouldn't get annoyed.

And, remember, you can't pay your rent or buy groceries with unvested options. You need cash money for that.

You own 1% of options and company is bought for $10m.

Your payoff?

Likely $0.

He forgot to mention preferred shares given to VC’s with liquidation preferences that likely never disclosed to new engineers.

This is what makes new engineer to sacrifice his salary for a possible liquidation even that likely either never happens or there is no money left for him after VCs took their xN ratios off the payoff.

You are a founder.

They are working with a technology or in an industry that you specifically want to work with and it is very hard to work on it professionally, and doing side projects are infeasible.

You need experience and you have no other option to get experience.

You are getting a significant title bump that moves your career forwards.

Invalid reasons for working at a startup:

Equity (getting rich off stock options) - this is very likely to be worthless unless you are a co-founder.

Salary - you would make (much) more at a big company.

Work life balance - you will work harder than you ever have.

Stability - does not exist.

Benefits - very bad.

Learning - they will not have any formal training nor time to train you, so be prepared to self-learn.

---

All that said, I enjoyed my time as an employee at multiple startups. Just go in for the right reasons and your eyes wide open.

There are tons of resources online for questions to ask, and I think the company/viability questions from the post are good, but I would add to them some of these types of questions:

How you will be managed/evaluated and the mission of the company: https://www.themuse.com/advice/8-questions-most-people-dont-...

How your founder/manager will navigate conflict, which is inevitable: https://www.thebalancecareers.com/interview-questions-to-ass...

More specifically: Is there a demand for the product? Are there competitors? If not, why not -- are you sure the product is actually something that somebody wants? If there are competitors -- how will your startup compete with them? Do you trust the people running the company to guide it to success, either directly, or because they have plans to hire people who can? Is the technology feasible, or are the founders embarking on an R&D project?

There are no guarantees of course, and you can learn a lot and have fun at a startup that fails, but do your best to join with your eyes wide open.

The few success stories, such as Airbnb and Facebook, are the extreme exception.

Ask yourself-

Do I trust the founders?

Can I have healthy debate with the founders?

Will my feedback be considered by the founders?

Am I compatible with the founders?

Are the founders compatible with each other and are they able to work together constructively?

I will say this much. People have bad memories. That includes you. You think you remember that conversation perfectly? You probably don't.

Get. It. In. Writing. And don't trust anyone who won't commit to writing.

1) A startup with marginal success and showing growing signs can simply ignore you and your questions and move to the next candidate. Startups where all these ducks are in a row has a strong candidate pipeline and they simply move on. You run the risk of standing out not as a diligent person, but as someone who is meddling in issues beyond his/her means.

2) A startup willing to divulge all this and walk the extra distance for you is probably too raw and desperately short of talent. When you get hold of all of this information, you might feel this startup is not worth it, given you now know where the skeletons are buried.

In the end, you really kind of have to wing it. Just like the VCs, the founders and everyone else is at an early stage of an endeavor. It is a high risk game, period.

My 2c is often towards ignoring all this math and doing your best to learn more about the founders, their motivation and if they will take care of you. Good founders always find a way to compensate you for your hard work whether by financial means or by paying it forward in other ways.

One of my friends works in a startup in Berlin where he was offered equity as one of the founders (10th engender or sth like that). Chances that he will be able to liquidate them in foreseeable future is non existing.

Nobody else that I know was offered an equity, even though quite a lot of my friends work for well funded startups. I worked in some and nobody offered me anything else but a salary.

If I relocated near SF? Sure, there would be a possibility. If I was a rockstar and one of first 5 cofounders? Also yes, but I am not famous.

I am really skeptical about any such post, as I saw myself that some strategies that works in Silicon Valley do not work anywhere else and I am not into moving to the most spoiled IT region in the world.

Some of the specific questions are not great depending on cultural context. For example if someone joining my dev team asked me to pay to ship their car somewhere I'd ask them why they needed a car to code. But I'm in London, where having a car has marginal/negative utility versus being essential in other places.

On the equity side, if someone asked these questions I'd know they don't understand equity. What would really help is to see the cap table so you get liquidation preferences etc but you're not going to get to see the cap table most places if you're just going for a dev job. As it is, he says you might not get told the strike price on your options, which in many/most countries your employer would be legally obliged to tell you as it's part of the valuation of your comp for tax purposes.

Equity in a startup is often used as a way to entice people to work without having to pay them market rates. If you suspect this is the case, definitely keep in mind that this equity could very well never be worth more than $0.

If you are interested in the value of the equity, then you have to be interested in the value of the business. You must understand whether you think the business value can grow. And this requires much more research and business strategy evaluation than most jobs offers.

It's worse than when negotiating with a bigger company actually, cause there you're just negotiating with HR department employees who would follow the law more closely. At a large corp, you largely get what you expect.

Be very wary of what you're promised and told. I, unfortunately, was burnt by this. I largely trusted everything that I was promised/told about the company performance. But it was all hoax.

So an additional tip: Cross-check with your friends how they feel about the company. Make this effort even if you are a bit introverted and don't like discussing job offers etc with other people. Match what your research about the startup tells you with what the founders told you about the company performance. Look out for red flags.

On the fundraising side, I’d add, “What is your fundraising steategy” when talking to the founders. This massively changes potential value calculations in terms of equity. I know some founders who are focused on not raising funds and pure profitability, others who are focused on growth by any means. Part of the calculus here is that by not shooting for more fundraising rounds, the founders may be signaling that they won’t be selling anytime soon. In that case, you should look to understand what your exercise rights are for your options. Do you have to exercise within 90 days, or is there a grace period?

But I don't see a growth opportunity in a big company, the work is boring as hell and there are engineers, who joined 5 years earlier than I did, are still on same level as mine.

And the key engineering work is hold tightly by early members, unless they retire, I don't see a chance.

And I want to do robotics. Although my current company is investing in the area, they only need people with the right background, i.e. PhDs in robotics. And I have talk with google recruiters, they let me choose a position before the interview, but all my selections are as boring as my current position.

Doing a startup seems to be only way?

My most important preliminary questions are all trying to get to root of one issue: Does this company follow a theory x vs theory y leadership model. So many companies out there claiming to be team oriented but in actuality are top down, my way or the highway operations.

I’ve read quite a few of these guides and they mostly focus on equity/benefits but I think product/market fit and feedback loops are a treasure trove for job seekers because they can show you the future as well as how focused the founder(s) are.

As a founder I’ve never been asked about feedback loops and rarely get asked about product market fit. We’re not technically a startup anymore, so that could be why. But I think those are useful questions for any company that isn’t a household name like Facebook or Apple.

What you should be looking for in an answer is whether it sounds like the company knows who it’s serving and is actively working to understand that audience even better.

Regardless of valuation, rounds of VC, or the flavor of popsicles you can find in the fridge, fit is what will ultimately get success. In my opinion/experience.

P.S. - understanding everything else is also super important for _you_, but this is important to understand to tell if there’s a future in which those would be worth anything.

This is an interesting, and perhaps telling, assertion. 40% can be done if you minimize costs, not only in the Bay Area, but anywhere else. Thus, the implicit point here is apparently that the opportunity set in the Bay Area is so great that it's justifiable to allocate an additional 15% of pretax income just to live there, relative to anywhere else on the planet.

I'm not sure if I buy that, especially within the context of taking a job that you've already been offered that has a defined comp package vs. moving somewhere to find a new job.

There is no clear answer for the correct time other than to not assume it's simply ok to state everything upfront (vs. time wasted on the part of the applicant).

90% of startups fail.

If you have two options, one being getting payed your preferred rate, and another being taking a huge pay cut for equity.. experience tells me to take the money every time and you’ll have made the right choice 90% of the time.

For most people money on hand today is way more important than future money that may never even materialize. And if you’re not most people, there will be future opportunities to buy into the company one way or another if you want to be an investor. You don’t even need to invest in the company you work for, there might be better investments that your real money that you get from the job can afford.

I've also asked about early exercise (83(b)) and term sheets, if there are bad terms i.e. liquidation pref, anti-dilution etc but not all companies are willing to share this info.

Also, I am curious about why companies don't just have a black box formula output generator, with your equity offer value, saying this is our projection and based on our current termsheet if the company exits at this value your options are worth X, with the option of dilution built in.

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.

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.

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.

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.

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.

https://angel.co/blog/liquidation-preference-your-equity-cou...

If you can't get those, then unless the equity is just butter to you, walk .. as you don't really know what the comp looks like.

valid: you want a sense of ownership and responsibility. if you don’t perform, there is a noticeable effect on the company.

valid: you want to be in an environment where others are just as committed as you to the success of the company. you want to treat your work as an endeavor, not as a means to a paycheck.

I don't know how else to get the kind of experience you get at a startup. A big company will give you depth, but a startup will give you breadth.

Also, if you ever plan to be a founder yourself, working at a big company might not give you any useful experience at all.

To add to this. The title of "early member of <insert famous startup company>" holds a lot of weight in SV circles. Whether or not you legitimately helped those companies in the early days, it's a strong signal that you are valuable. And those <insert famous startup company> doesn't have to be a company that necessarily had a huge exit or has a strong economic reputation. For example - early engineer of Yahoo? Ya, people probably think you're worth one's salt.

IMHO - I think this is the main driver people join startups. It's taboo, but vanity feels much more tangible than equity.

Benefits - very bad.

Both of these are valid reasons to work at a startup, if you have a family to feed and care for.

Sometimes any job is a good job, even if it's only temporary while you try to find the perfect gig.

Edit to add:

I've been in exactly this position. I took a dev job with a startup I knew was a complete loser, run by scam artists. But I had to put food on the table. Fortunately, I was only there about eight months before I landed a real job with a real company.

The dodgy company imploded, exactly as I expected it to.

You see guys working late at their little startup and maybe thing you should tell them it’s not going to happen. Because honestly for most of them it’s not.

But... I want to make the case that it's OK.

Even if it’s never happening they may be happy. If one stops viewing startups as $$$ opportunities and starts viewing them as rehab from the soulless corporate jobs full of soul-wilting mediocrity, politics, legacy, same old shit over and over, and backstabbing, then it might make a kind of sense to work at a startup instead. Take a pay cut and "try some different shit out" with a tightly-knit team.

It’s a chance to work with things that are greenfield and/or new/different/experiment. Maybe it works. It’s a chance to not be bored. You aren’t wedded to it and don’t need to do it forever. Stay up late and code for awhile. Have pizza. Debug. Try. Care.

The gotcha is if people focus on the IMGONNARICH including the management (where it translates to UNDERMARKETYOURCOMP, though maybe one doesn’t care). That’s poisonous but I think there are lots of options where this isn’t true.

The more people I talk to outside the Bay Area, the more I encounter who I think are doing it right. A lot of them are not crazy, they don’t really think IMGONNARICH. They don’t end up in the FEELINGSWILLBECRUSHED state after it doesn't work (because, honestly, it doesn't).

I like people and being around them. I love the feeling of a team pulling together and exploring the dark corners of a problem. So when a break is in order, the answer might be startup rehab. It's cheaper and better for your career than a full-on year off.

The title bump rarely moves your career forwards.

These questions have always guided me well.

1. I never graduated from university (life came up, and I couldn't afford to keep going); but, also,

2. I don't live in the US (I'm Canadian.)

Any of the US bigcorps that want to hire programmers, expect them to get a visa and move to the US.

You know what you need, to get a work visa as a programmer coming to the US?

A college degree!

So, my employer pool was instantly limited to non-US companies. Mostly local Canadian companies. Most of those are very conservative and also expect a college degree. The only ones that aren't, are startups. So that's what I had to do.

The really annoying thing is, I ended up doing work for these Canadian startups that would netted me a $300k USD salary if I had been doing it for a US bigcorp. But, because Canadian salaries are lower, and startup salaries are lower, I was only getting ~$60k.

After years of doing that, I'm a Canadian startup founder... and still only making (i.e. paying myself) $60k.

I guess I'm an object lesson in the value of a college degree!

Disagree with this one - yes you will need to self-learn, but learning to self-learn is an invaluable tool in itself. You will learn to be extremely non-reliant on other people, and you will probably need to learn about parts of the stack you did not know about before, and fast. You might learn about project management or giving sales pitches. If you are thinking about starting your own company, you will learn a huge amount about how this happens, and what that means (I learned that I didn't want to do it for example!)

I have learned a huge deal from my startup experience, probably double the rate I was learning at the bigger company I was working at before.

Because I would add "chaos" to the list of negatives. The odds are likely you're going to get a C-suite or board that has ADHD-like tendencies, especially when chasing large customers and/or funding rounds.

You will continually be dropping or delaying long-term work for short-term projects to help the company achieve other goals.

This was me and I paid for it. Right now I'm on week 8 of 30 hour weeks. It sucks.

I've never been an employee of a German company, but I'm in the process of founding a startup here in Berlin. I totally get how saving early employees from having to deal with that headache would be a blessing.

(In general, the advice in the article tracks with my experience working not just with SF-based startups but companies in other top-tier tech cities like London and NYC. If you get a job at a startup in SF, you'll absolutely get equity as meaningful part of your job offer, even if you actively don't want it. A large part of startups' ability to hire depends on them being able to convince you it's okay you're being paid literally less than half of what Facebook pays because someday your 0.01-0.1% equity stake might be worth something)

And I would not call it spoiled its just that in the US "engineers" (using the term widely) have managed to get a fairer share of the pie.

But setting up CI is a day's worth of work, and pays off almost immediately.

Having reasonable logging in an app of any serious size is a cultural thing; it takes exactly as much time to write as bad logging, and saves oodles of time every day when you have to discover and fix issues.

Compare it to building a motorbike. Yes, you want a prototype fast. But if you have all your tools stored as one big pile, or have oil and fuel spilled next to your welding machine, it does not speed you up; it sets you for an accident after accident.