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Questions to Ask Before Joining a Startup

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Re: Questions to Ask Before Joining a Startup

#241

the answer to every question on this list: "We are a private company and don't share this information." Outside of the room, the Engineering team laughs at your questions, Operations and the CEO give each other quizzical looks before laughing too, and they go on to the next candidate. You get smug satisfaction for not going with "THAT Company who cant answer simple questions", until a reminder about the rent payment…

I think these are all reasonable questions to ask a startup with no established reputation. If all you want is a 30% increase, these startups are probably not the fit for you to begin with.

Re: Questions to Ask Before Joining a Startup

#242
There are no engineering questions on this list, and the more I think about it, the more correct I think that is. Unless you're stretching the definition of a startup, most of what passes for current engineering is volatile and subject to lots of change. Better to ask questions about the team and their experience so you know what you'll need to build.

Re: Questions to Ask Before Joining a Startup

#243
post #4

I've been thinking about low-friction options for getting a sense of the engineering quality. I don't think I'm alone in thinking that technical debt and bad software development practices are a top concern. 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…

I think if a company has good answers to these questions, then they aren't really a startup. More often than not, if they're hiring you (being quite senior) it's because they need you to do all those things.

But I do get where you're coming from. In my experience, it's better to ask about the team and its CTO to understand how decisions get made, and if the team is capable of recognizing quality. I don't care if CI isn't in place when I join as long as the team recognizes its importance and knows they need to get to it.

Re: Questions to Ask Before Joining a Startup

#244

Having worked at several start-ups, I'd say the employment risks are not worth the cost. In most of my cases, when the start-up hasn't raised enough money, you end up with a poor work environment - pissed off/stressed bosses, weird work hours, "do anything" to save the business mentality... Generally layoffs/firings occur pretty abruptly and you're left filing for unemployment without a "thank you". My advice would b…

3-5 years old with $100M revenue is deep into unicorn territory already. I'm sure you can count companies that currently fit those criteria on one hand.

Re: Questions to Ask Before Joining a Startup

#245
post #179
post #58

Earlier quoted context omitted.

If you have preferred shares, you often have a "2X liquidation preference"[1] or other multiple. This means that you are guaranteed to get at least two times your initial investment in a liquidation event, even if the value of your shares at the time is less than that amount. This can (and often does) eat into the common stockholders' (e.g. employees) liquidation amounts. 1. https://www.businessinsider.com/how-liquid…

In my experience (~ 20 years at institutional VC funds), 2x preference (or anything above 1x) is extremely rare. It comes up only when there is a distressed situation, and the investors do not believe that they will receive any money beyond their liquidation preference (i.e. other junior liquidation preferences will consume the rest of the proceeds from the sale of the company).

I saw it around the dot-com days along with a lot of other extremely dubious terms for extremely desperate founders - at least in NYC.

Agreed that more than a 1x liquidation preference these days would generally be surprising, but in a low end scenario or with a few big rounds, all it takes is a 1x to wipe out any upside for founders and employees, but if you're deemed worth it, the acquiring company can offer you a worthwhile incentive to stick around.

Re: Questions to Ask Before Joining a Startup

#246

Earlier quoted context omitted.

Some startups are reluctant to tell you how many shares are outstanding in the company (happened to my wife). They say you get 100,000 options, but will not tell you the info needed to properly estimate the potential value of those options. In my wife's case, they just said to trust them that it was a valuable offer.

Not sure how this works elsewhere, but in the UK you can find public documents submitted by companies (including private ones) on the Companies House website and find out how many shares are outstanding (as well as some basic information about current shareholders).

Not a thing in the US for private companies.

Re: Questions to Ask Before Joining a Startup

#247
post #72

Earlier quoted context omitted.

In the context of a startup, I would expect almost all of those to be disappointing. But maybe that's what you're hoping to see. In my opinion, if you're a start-up and you've got all those boxes checked, you're possibly doing the right things in the wrong order, and that's a red flag for me. What I hope to hear are responses like, "so this is how we're doing CI. It's awful, almost non-existent. But that's because at…

I would expect most to be disappointing too, and it's a good idea to avoid those. Proper logging doesn't take more time, it just takes more discipline / giving a damn. People and companies that say: we don't have time to do it right Almost always mean: we don't know how to do it right Talent, not time, is the enemy of quality. (at some point that stops being true, but most companies (startups or not) are soooo far fr…

For the first year or so, the only way to get builds of our software was for me to click "build" in Visual Studio, on my laptop.

I definitely knew how to set up a build server, CI pipeline, etc. It just would have meant that every time I (not we!) changed the build, I would have to fix my own machine and the pipeline. I'd much rather spend that time fixing one more issue, or adding one more feature.

There are numerous things that increase velocity for a large team, but decrease it when the product is just getting started. Joel Spolsky wrote about something similar almost a decade ago, https://www.joelonsoftware.com/2009/09/23/the-duct-tape-prog...

Re: Questions to Ask Before Joining a Startup

#248
post #66

Earlier quoted context omitted.

This. As I always say, "If you are building a startup, over-engineering is a far bigger sin than creating technical debt."

Setting up CI is basically as simple as adding a small .yml config file to your git repo (if you are using a service like Travis or Circle CI) and clicking a couple of buttons to give the tool access to your github repo.

If you are writing a web app maybe, if you’re writing a VR app, it’s definitely not that easy.

Re: Questions to Ask Before Joining a Startup

#249

Earlier quoted context omitted.

If you want your startup to run for more than a year (= roughly the time the effects of technical debt start to kick in significantly in my experience), you need to find a good way how to handle technical debt, and keep it in check. I have seen my share of startups where a platform plagued with technical debt was the main limitation for growth, which is a very avoidable situation.

> If you want your startup to run for more than a year I've never seen a start-up fail on account of technical debt. Re-engineering is expensive, but it means you have something worth re-engineering. I've seen lots of start-ups fail because money that should have been spent attracting and retaining users got burned on an elaborate engineering process.

Ok but like middle ground exists here. There is a huge difference between thinking carefully about what you need to do right and planning what bits are going to end up as technical debt, and how you can fix it later - and what actually ends up happening in my experience where everything is shit because we're too busy being a s t a r t u p to practice engineering.

Re: Questions to Ask Before Joining a Startup

#250

the answer to every question on this list: "We are a private company and don't share this information." Outside of the room, the Engineering team laughs at your questions, Operations and the CEO give each other quizzical looks before laughing too, and they go on to the next candidate. You get smug satisfaction for not going with "THAT Company who cant answer simple questions", until a reminder about the rent payment…

I understand the cynicism behind this comment, but hopefully if you have one offer you are considering, you have a few more offers as well.

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."

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