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How to Choose a Startup to Work for by Thinking Like an Investor

302 points by Harj 8y ago

deleted 8y ago
[deleted]
xiphias2 8y ago
,,It's also only by joining a successful startup early that you can get remarkably steep career trajectories, like Jeff Dean'' It's sad that Jeff Dean is the last example the article can give. When evaluating a startup as an investor, I see that while investors get great terms, employees get junk options. So until it changes, I'm just staying with big companies, thank you very much.
lordnacho 8y ago
Probably one of your main considerations should be how you are left if the startup dies. There's plenty of good advice here about how to pick a startup that might succeed. So there's a few considerations: - Have you got some savings, in case it dies suddenly? You need to be able to pay rent until you find another job. Hopefully the startup is located near these other jobs. - Does it allow you to build on existing experience? If you can claim you're in the same industry, you're not losing much (perceived) seniority by trying your luck for a bit. - Does it give you an easy promotion? This is probably one of the main things a startup can offer. Just being able to add "Senior" to your name or "Team Lead" a few years before you would in BigCo might be worth it. - Do you get to work with the tech that you want for your CV? You probably have an idea of what's hot to have on a CV, and a startup is relatively new, so maybe you can direct things that way?
jorblumesea 8y ago
Bad advice. You shouldn't pick a startup solely based off these criteria. You are a very minor investor that is the last to get paid. Investors can accept far more risk and reward, and care very little for things like whether the employees are happy. Does the work look interesting? Will you learn new things? Do you like the problem space the startup operates in? How is the culture? Fit or not? Will you be happy there?
qaq 8y ago
Even top VCs need a portfolio of companies to produce a return. If you asked a VC to bet a whole fund on a single company :) and these are people who's full time job is to pick companies
- microtherion 8y ago
  Yeah, a key strategy for investors is to diversify, and that's exactly what startup employees cannot meaningfully do.
  - jcoffland 8y ago
    Startup employees could pool their risk by creating their own shared investment fund which held all their shares/options in trust and spread out the winnings. The reward would be far less but more predictable. I doubt many would have the foresight to commit to something like this.
    - albertgoeswoof 8y ago
      Neat idea, but how would you choose who qualifies to join?
      - jcoffland 8y ago
        Probably the same way a VC chooses startups.
- ryandrake 8y ago
  Start up employees take on far more risk than startup investors. Investors can diversify over 10s or 100s of companies but an employee has to pick just one and bet their career on it.
sjg007 8y ago
Choosing a YC startup is probably the best bet. If it fails you can use that network to get into another YC company.
techslave 8y ago
> However you will learn significantly more, build a stronger network, and accelerate your career trajectory much faster by joining a successful startup than an average one. smack forehead Yes, what ever could I have been thinking before! Yes, yes, I should only be joining a successful startup, not an average one! > steep career trajectories, like Jeff Dean, Marissa Mayer or Chris Cox. Yes yes! New plan: be Jeff Dean! > Next, you need to evaluate the strength of the team and market Unfortunately, this is not realistically possible for most non name-brand candidates. The company is not going to entertain the amount of inquiry (due diligence) you would need to pursue. > Evaluating the relationship between founders is as important as evaluating the founders themselves. Indeed it is! Good luck getting access to do that ... This article is just more hyperbole from triplebyte. I wonder how their business is doing ... https://triplebyte.com/careers https://triplebyte.com/careers: > We've already achieved profitablity But if I may quote from this article: > one thing we learned at YC was not to be fooled by large absolute numbers. What matters most is the growth rate. triplebyte, put your money where your mouth is and advertise your top line growth rate, not the fact that you are profitable. When your fee is on the order of $30k per hire and your infra and operating costs are low, I expect you to be profitable.
- sulam 8y ago
  Evaluating the strength of the team and the market is something you can do with zero involvement from the company, and you probably shouldn't depend on them to tell you either even if they offered. Getting a sense of founder dynamics can be harder, depending on stage, but it's easy if you're early enough. I interviewed at Dropbox when it was 20 people and it was obvious what roles Drew and Arash played, as an example. At a larger stage this is harder, but you have more public sources of information at that point. Regarding Triplebyte's profits, you should be asking how fast they're growing. Finally, we should all be Jeff Dean. :)
shoo 8y ago
As an "investor" you should consider the range of asset classes available to you when deciding how to invest your time and labour. See Dan Luu's articles about "big company vs startups" and "options versus cash" https://danluu.com/startup-tradeoffs/ https://danluu.com/startup-tradeoffs/ https://danluu.com/startup-options/ https://danluu.com/startup-options/
throwaway190107 8y ago
I think the author should produce some data showing this is a viable strategy before he gives people advice that could lose them hundreds of thousands of dollars. Other people have pointed out the statistical problems with this strategy so I won't restate them. The author may sincerely believe in his own advice, but we should note that he did not, himself, get rich this way. A dropout from elite UK universities, he founded a startup and exited for a small amount of money. Since then he has worked for Y Combinator, invested, and also founded a few companies. Taggar has never, himself, been anything like a startup employee. And great for him; he seems extremely talented and maybe that route isn't for him. But his company (TripleByte) profits from directing talented people into these kinds of companies.
Harj 8y ago
Rather than treating predicting startup success as an intractable problem, I think anyone considering joining a startup should act like a startup investor making a bet on how much the value of equity in that startup will grow over time. Startup investors do this for a living and that's essentially what you are too. You're investing your time and they are investing money.
- wolco 8y ago
  Place multiple bets over the years
- arachnids 8y ago
  Hrm, the parallel feels really forced to me. You can invest money in multiple startups at the same time, to hedge your bets. You can't do that with your time if you plan on working full-time.
  - Harj 8y ago
    Sure, you can't diversify in parallel but you can in series.
    - chrisbennet 8y ago
      Considering how long you would have to stay to get anything from an equity event (4-8 yrs?) you realistically can't work for 10 startups. If you luck out and work for one that does have some success, you will probably find that, unlike a VC, you don't have "2X preferences" or an anti-dilution arrangement so you get nothing or next to nothing. In the meantime you may have traded your youth for magic beans - putting off things like getting a house, a girlfriend, etc because you are working long hours for sub-market pay. That is the real tragedy.
      - drewmol 8y ago
        >Putting off things like getting a house, a girlfriend, etc because you are working long hours for sub-market pay. That is the real tragedy. Just wanted to repeat this for emphasis ;-)
dawhizkid 8y ago
it's funny to think of my own finances...I have a portfolio of stock from 3 startups now that has worked out surprisingly well
sharkweek 8y ago
I worked at three startups before taking the current break I'm on - one I left before my stock was worth anything (would have paid out a small amount in an acquisition), another, the stock is now worth zero, and the third has a shot at being worth about a year's salary if current late-stage valuation is to be representative of a potential buyout/IPO (I'd say odds are alright this will happen). While I try not to think about it, because honestly the experience was worth it, I would have made far more over the last eight years of my career staying put at BigCo. With that being said... All three times, despite considering myself a pretty rational person, I got this strange psychological delusion when joining the startup that it was going to somehow magically make me rich. I think it's probably the "honeymoon" stage of joining any company. Things are awesome! The culture is fast-paced, chaotic, and offers plenty of opportunity! This is a rocket ship! It kind of matches the "what if" feeling of buying a lotto ticket. It's impossible not to imagine what might happen. I think if I jump back into startupville, my cynicism toward the "get-rich-fast with these private options" will outweigh the bright-eyed, bushy-tailed sensation of my 20s.
- dawhizkid 8y ago
  IMO there's only two paths that really makes sense now when considering a private co. Either a) join super early (e.g. penny strike price) with a meaningful % of total company (at least 10 bps) OR b) join late stage growth co that offers RSUs over options (e.g. "Softbank" stage cos). Joining a "middle" stage co where you are offered expensive options is the worst, since you've missed out on the early upside and you take on a ton of risk due to cost of exercising.
  - joshe 8y ago
    Sorry have to delete these, not comfortable with these comments sitting on the internet forever.
    - dawhizkid 8y ago
      That is not true. You keep whatever you vest (i.e. typically stay at a company at least 1 year). That is the same for stock options. Typically companies that offer RSUs have achieved scale (your Ubers and Stripes of the world), so yes the upside is lower, but the "pros" are that it's more obvious to you what the value of the grants are and you don't have any cost to exercise them like with options. These companies know that because they are less liquid vs public cos that candidates are right to discount them, which is why they usually offer more than what you'd otherwise receive from a Google or FB.
acconrad 8y ago
This is how I've approached joining the last two companies I've signed on with. In the hiring process I ask to speak with finance and the founders to see if the company has the legs to be a real rocket ship. Remember that an interview is just as much about them interviewing you as it is for you to interview them.
- davidw 8y ago
  How likely is it that you as a potential employee get to see the books and know what's going on like that these days? Honest question; seems like it's a tougher thing to get access to than for a VC, but maybe I'm wrong.
  - wolco 8y ago
    They (founders),are use to showing investors so it has never been an issue. Don't try the same with a small business. You will probably get kicked out.
    - maxxxxx 8y ago
      I have asked several companies about financials and they never gave any meaningful information. I got the impression that as an employee you aren't supposed to ask any questions. This is acceptable only for investors and upper management.
      - wolco 8y ago
        The companies who were open were the ones who options/shares became worth something from personal experience. The ones who hide those details had worthless options.
  - lifekaizen 8y ago
    The article is mainly about revenue growth, and any startup should be willing to share top line revenue and growth rate. A large reason not to share things is some info is sensitive, for example the share count is a useful number, while the full cap table with each investor’s pricing, terms, and contact info, and other employee grants, would be sensitive and might be more guarded. Same thing about total revenue versus the customer list. More traditional advice is to ask about the fully diluted share count, so you can see what percentage the options would be, and of course the vesting schedule and purchase terms. Also I’d also ask about cash or runway, which is related to the ability to survive a rough patch. I was CEO and founder of a YC funded startup and have some experience hiring at the seed stage. For me personally, I wanted engaged people and asking good questions was a positive sign.
pembrook 8y ago
This kind of advice is similar to the "get rich day trading stocks" narrative. It only sounds realistic if you are ignorant of the statistical probabilities involved (it seems most people are). A vast majority of VC funds produce weak or negative returns. And this is after diversifying their fund investment across 10+ start-ups and assuming that 90% are going to be losers compared to putting that money in public equities. You can't work for 10+ companies at once like a VC can. And even if you could, the odds are still against you. The idea that you'll be able to pick ONE winner at an early stage is, quite frankly hilarious and naive.
- jacquesm 8y ago
  Another major reason that you won't be able to pick the winner is because you only get to pick once, and then you are booked for a long time. If you think a better one comes along you now have a sunk cost, and you'll be starting all over again, with a very good chance that your 'better' one will end up being worse. So the odds are very much against you if you are evaluating start-ups serially. The better way to do it is to evaluate a whole pile of them at once, and then to pick the best one that you can find. And you're going to have to do a lot of work to evaluate those options, about as much as though your future depends on it, because it does. If you're not prepared to put in that kind of work then it really is just a lottery, and you're most likely better off to just take a job that pays you roughly what you are worth on the market, in the longer term that + a good savings regime will be a much surer path to some serious cash than buying lottery tickets at an opportunity cost of 300-500K each.
- echevil 8y ago
  I think the right way to think about this problem is treating picking the winner at an early stage as a probability. Even though the value of the probability is small, you'd still want to maximize it when you're picking a startup to join, and you can do much better than picking randomly. You can continue to evaluate the probability after joining a startup.
artiscode 8y ago
I accepted early on that working for a startup will probably not make me rich. Quite the opposite, I may wake up one day and find out that I no longer have a job or my next salary isn't coming. I'm not the kind of person who believes in gambling. Working and living in Europe doesn't really help with the vision that I might join a European unicorn startup, whose stocks might not be worthless one day. However I do see a lot of benefits that come with working for a startup. You can voice your opinion and be heard. Pushing code to production on your first day. Owning what you do and being able to make decisions. Creating your own environment in which you can learn and become a better developer. And, most importantly, startups are more open to remote than BigCo Inc. Monetary compensation might be less, but freedom has a price. If I'm able to work remotely, I can move to a place that is cheaper to live.
- fyfy18 8y ago
  Most of the startups I've come across in Europe usually pay at or near to market rates. Maybe it's just my experience (I've mostly been working as a contractor), but I find this somewhat surprising, given that the social structures here mean that taking a risk by working unpaid/lower pay for a startup isn't such a big issue.
kbutler 8y ago
By working at twenty of them, expecting 15 to fail, 4 to not completely fail, and one to go big?
- kelp 8y ago
  This is about my career. 8 startups, earlish employee at 6. 1 mediocre IPO, and 1 very successful IPO. The rest basically failures or zombies that made me no extra money. Probably a little more lucky than most.
  - dabockster 8y ago
    Tons more lucky than most. My last startup job misclassified me when funds got tight. A friend of mine who joined later never got paid (good luck filing a wage claim in WA state if L&I’s system still thinks you’re a contractor).
    - kelp 8y ago
      Perhaps also luck, but I’ve managed to have a spidy sense for when things are going the wrong way, and got out / moved on before it got that bad.
      - freedomben 8y ago
        What are some of the signs/symptoms that trigger your spidy sense?
        dabockster 8y ago
        The big one for me was realizing that my boss had lied about knowing how to code. Other red flags include code and documentation quality, how the business sells itself to potential customers (does it greatly oversell it’s abilities), the expiration date of the coffee/tea in the break room (I got food poisoning when I drank the startup’s three year expired tea - the founders were still wondering why they felt like crap all the time when I left), etc. It’s really a bunch of little things that, when seen as off all at once, will trip your spidey sense to jump ship.
mrnobody_67 8y ago
Best risk-reward is VP or SVP level at Series C or D company which gets you options for 1-2% of the company... switch every 18 months to diversify and build a portfolio but negotiate 10 year exercise window on your options when you leave rather than the standard 90 days. Thousands of execs doing that around Silicon Valley working through Daversa and other executive recruiters (who themselves get $85K-$100K per executive hire).
- BadassFractal 8y ago
  That's what I hear too these days. The risk/reward sweet spot in the Valley apparently is either VC (collect management fee for a few years, don't have to show results for a while) or what you said, which is being an executive at a 50+ person company that's shown a very strong trajectory of revenue growth.
- kkotak 8y ago
  I can't upvote this comment enough. The bottomline for risk keen candidates is to get in with founder's equity and risk averse (and experienced, of course) to work with a headhunter to maximize your chances of building wealth.
- naveen99 8y ago
  Or you could just take a non startup job for higher pay and buy 0.1% of a bunch of late stage startups on EquityZen or Equidate. No need to wait 10 years...
  - deanmoriarty 8y ago
    I would advise against that, I tried to dabble with both platforms, but the markup at which those shares are sold is often incredibly high: common shares of most companies on those platforms are actually sold at prices higher than the preferred (crazy), even if such company just went through a very recent round of funding, meaning that the preferred price is pretty much the very top investors valued the company at. I honestly don't know who would buy that, the idea I got by doing some basic due diligence on those deals is that who puts them online thinks "let's see if we can attract some dumb money to give us some liquidity at an insane premium". If you sell things at a fair price (e.g. selling common shares at the preferred price * 0.8, depending on the current stage of the company), investors will want to give you liquidity way before your offer on equityzen gets accepted and pollutes the cap table (I speak from direct experience), so what's left on those crowdsourced platforms is many times overpriced garbage.
dabockster 8y ago
TripleByte is a hiring agency with a financial interest in placing people with startups of all sizes and financial states. This information should be taken with a grain of salt.
- kkotak 8y ago
  And in my experience they focus solely on tech IC candidates, which is not for everyone.
  - dabockster 8y ago
    I’m out of the loop. What do you mean by tech IC candidate?
sampo 8y ago
The author writes from the point of view of an investor. How likely it is that as a candidate for a job, they would give you all that service and access to all that information? A meeting with all the founders? Unless you're a valued, seasoned industry veteran, joining a very early stage startup founded by 20-somethings, would you really be able to access all that the author suggests?
BadassFractal 8y ago
Naive question: why not work for a FAANG, try to make close to half a million after enough time, promotions and jumping ship between the different firms, then just invest whatever you're not spending into the stock market or whatever other assets you choose? Take the 400k you're not spending and dump into Tesla and friends, or whatever other sexy stock du jour? Seems like a much healthier risk profile unless you ONLY want a huge Google-like unicorn outcome as an early employee.
- sciencewolf 8y ago
  It is much easier to get a job at a growing VC-backed startup than a FAANG.
  - BadassFractal 8y ago
    I suppose so. That could be one's foot in the door for a FAANG role later down the line?
- owyn 8y ago
  If you can, you probably should! I've come to believe that the best chances of getting a financial benefit (as opposed to just an experience benefit) from working at a startup is to be a founder. If you're "just" an engineer, it's unlikely to be worth it.
takanori 8y ago
I found these questions to be pretty interesting https://medium.com/@therealpankaj/interview-questions-to-ask-a-startup-ceo-cf04d71752e8 https://medium.com/@therealpankaj/interview-questions-to-ask...
ken 8y ago
> It's also only by joining a successful startup early that you can get remarkably steep career trajectories, like Jeff Dean, Marissa Mayer or Chris Cox. The number of people with these sort of "career trajectories" is vanishingly small. This reminds me of what Phil Greenspan wrote (2006?), mocking the college student's career evaluation process: "I can't decide if I want to be a scientist like James Watson, a musician like Britney Spears, or an actor like Harrison Ford."
lpolovets 8y ago
An aside to this article: along with thinking like an investor, you can also reach out to investors who will often be willing to help with your job search. For example, as a seed VC there are now about 80 companies at various stages that my fund works with. If someone emails me and says, "I'm a good engineer who wants to join a Series A startup in SF or Oakland that has characteristics X, Y, and Z," there's a good chance I can make a few useful recs. There's nice incentive alignment here: the VC doesn't get any compensation, they just want their companies and the prospective employee to do well. That means 1) we won't recommend a bad fit to an employee because we want the employee to join and be happy and get their friends to ask us for company recs; 2) we won't recommend a bad fit to a company because we want founders to like us and not feel distracted by us. We're going for quality, not quantity -- and you're welcome to ignore our suggestions. So if you're good at what you do and are looking to join a startup, consider soliciting recs from a few investors with large portfolios. I wrote a short post about this a few years ago: https://www.codingvc.com/using-investors-to-find-the-ideal-startup-job/ https://www.codingvc.com/using-investors-to-find-the-ideal-s... I might regret posting this invite on HN, but if you want to join a startup and want recs, my email is in my blog's header.
tinyhouse 8y ago
Some good points there. A couple of things to add from my experience. The asking hard questions is very important. I once interviewed with a startup that just raised $3MM. You pay them a small fee and if your flight gets cancelled they find you a new one for free. I pressed the founder hard on why someone like me would buy that insurance and his answer eventually was for the same reason you buy insurance for your car or house. Once he gave me that answer I knew I'm not going to work there. And this was actually a nice startup with some good people. There are much worse startups with founders who have no clue and god knows how they managed to raise money. One founder once told me he is well connected and one phone call and people write him checks (red flag). Then there are the ones who are really shady and will lie about everything. Be very careful and don't ignore the red flags! Another important point is that you need to make sure the startup really needs you. In the past I talked with two startups that built their pitch around AI but they had very little knowledge of AI so what they had in mind wasn't really possible and even if it was, the product had millions of other things to succeed before AI was even needed. The problem is that founders sometimes focus too much about their pitch and how to impress investors rather than on their product.
tschwimmer 8y ago
The metaphor of early startup employee as investor seems really smart at first but is ludicrous in reality. It is physically impossible to choose a startup like a VC because you cannot diversify your portfolio like they can. VCs can sprinkle (relatively) small amounts of money across dozens or hundreds of startups. If one fails then the impact to the portfolio is negligible. In fact, VCs expect that most of their portfolio probably won't pan out. Good luck diversifying as an employee. Working part time at even 2 startups is obviously laughable. If you're in it for the money, working at a startup is probably not for you. It really is akin to gambling. There may seem to be more information available than gambling, but there is so much unknown and hidden information it's damn near impossible to make a 'rational' decision. That's not to say you should never work at a startup. Startups are often great learning opportunities because you usually have both broad and deep scope of responsibility. There's also often better alignment between management and employees because people tend to be working stuff that is materially relatable to the bottom line. It can also be a career accelerator if the company grows headcount rapidly and you suddenly become a 'senior person'™. YMMV.
- fhbdukfrh 8y ago
  I agree with you, and this was my initial response when i started reading the post. VCs also get far more information about the company and can demand way more control. How many employees of a startup get a board seat, even if you're non-founder employee #1? Even those diversified portfolios aren't going to have huge returns in most cases. I think the lesson is that if your value proposition is exchanging your skills and time for money (ie, an employee) you can't parlay that into startup style returns without essentially winning the lottery. If you can pick the next unicorn for employment purposes don't waste your talents on actually being an employee
  - danenania 8y ago
    On the other side, as an early employee you can have a much bigger impact on the odds of success than an investor. If you think a company has huge potential, but it's missing X/Y/Z, and you're an expert in X/Y/Z, then you have both a unique insight and unique leverage to make a success out of something that might not have been without you. Looking for situations where you make the difference is perhaps one way to have the whole thing feel like less of a lottery.
JohnFen 8y ago
I love working for startups, but not working for startups that have VC money -- the involvement of VCs changes the nature of everything. But then, my goal is primarily to do meaningful work on interesting projects. I have little interest in getting rich.
rohithb 8y ago
Just read the conclusions, the writer is not sure what really works.
nikanj 8y ago
Being an early-stage employee gets you all the downsides of being a founder, with only a fraction of the benefits.
seretogis 8y ago
What about the Groucho Marx strategy of not investing in any company which would have someone like yourself as an employee?
nadim 8y ago
“I think startup employees should re-evaluate the growth trajectory of their startup every year.” At a bare minimum. Probably more often.
raygelogic 8y ago
the best advice I can offer is to join a team that has deep pockets. the biggest reason my company succeeded is that they had cash to burn. sure, they were smart. they moved quickly, they dropped failing products instead of holding on to them. they made consistently good decisions. but they also were able to sink millions into the company's products and promotion thereof without going under for years, long enough to stumble upon a hugely profitable model. no idea how to assess the size of a company's pockets. maybe one that has a founder who has already had a successful exit. every other attribute of a company is basically fortune telling.
general8bitso 8y ago
Which scratch-off ticket should I buy at the gas station?
throaway9999 8y ago
What's considered a good bps for an very senior engineer joining as 20th employee, at a series A company with a couple of million dollars revenue?
known 8y ago
And why startups condense in America? http://paulgraham.com/america.html http://paulgraham.com/america.html
halfjoking 8y ago
“If you're happy working where you are, and you don't have any ambition to do anything else, you're probably going to get paid less and work more if you leave for a startup. If getting paid less and working more is unappealing to you, then I would recommend staying where you are!” There's another option. You can pick a job that isn't a startup, that makes you hate your life, and phone it in every day just to get by. You save your energy and grind away at night on your own company. I say "company" instead of startup because I don't think venture capital is the right thing to pursue for a single founder doing this. Just have a goal to build a product that has at least 1000 customers paying $10/mon so you can quit your dayjob. The hatred of your dayjob will fuel your motivation to work at night. A startup is much riskier than taking this approach. You put in 60 hours a week at a startup and even in the very unlikely scenario it pays off and the startup becomes huge - at most you have a 1% stake and become a millionaire. You become a millionaire way easier working on your own project. So my philosophy is to get a job you hate - work to build the future you want yourself - never let anyone else exploit you to the point where the only way you become a millionaire is if they become a billionaire.

302 points by Harj 8y ago

deleted 8y ago

[deleted]

,,It's also only by joining a successful startup early that you can get remarkably steep career trajectories, like Jeff Dean'' It's sad that Jeff Dean is the last example the article can give. When evaluating a startup as an investor, I see that while investors get great terms, employees get junk options. So until it changes, I'm just staying with big companies, thank you very much.

lordnacho 8y ago

Probably one of your main considerations should be how you are left if the startup dies. There's plenty of good advice here about how to pick a startup that might succeed. So there's a few considerations: - Have you got some savings, in case it dies suddenly? You need to be able to pay rent until you find another job. Hopefully the startup is located near these other jobs. - Does it allow you to build on existing experience? If you can claim you're in the same industry, you're not losing much (perceived) seniority by trying your luck for a bit. - Does it give you an easy promotion? This is probably one of the main things a startup can offer. Just being able to add "Senior" to your name or "Team Lead" a few years before you would in BigCo might be worth it. - Do you get to work with the tech that you want for your CV? You probably have an idea of what's hot to have on a CV, and a startup is relatively new, so maybe you can direct things that way?

jorblumesea 8y ago

Bad advice. You shouldn't pick a startup solely based off these criteria. You are a very minor investor that is the last to get paid. Investors can accept far more risk and reward, and care very little for things like whether the employees are happy. Does the work look interesting? Will you learn new things? Do you like the problem space the startup operates in? How is the culture? Fit or not? Will you be happy there?

qaq 8y ago

Even top VCs need a portfolio of companies to produce a return. If you asked a VC to bet a whole fund on a single company :) and these are people who's full time job is to pick companies

microtherion 8y ago
Yeah, a key strategy for investors is to diversify, and that's exactly what startup employees cannot meaningfully do.
- jcoffland 8y ago
  Startup employees could pool their risk by creating their own shared investment fund which held all their shares/options in trust and spread out the winnings. The reward would be far less but more predictable. I doubt many would have the foresight to commit to something like this.
  - albertgoeswoof 8y ago
    Neat idea, but how would you choose who qualifies to join?
    - jcoffland 8y ago
      Probably the same way a VC chooses startups.
ryandrake 8y ago
Start up employees take on far more risk than startup investors. Investors can diversify over 10s or 100s of companies but an employee has to pick just one and bet their career on it.

sjg007 8y ago

Choosing a YC startup is probably the best bet. If it fails you can use that network to get into another YC company.

techslave 8y ago

> However you will learn significantly more, build a stronger network, and accelerate your career trajectory much faster by joining a successful startup than an average one. smack forehead Yes, what ever could I have been thinking before! Yes, yes, I should only be joining a successful startup, not an average one! > steep career trajectories, like Jeff Dean, Marissa Mayer or Chris Cox. Yes yes! New plan: be Jeff Dean! > Next, you need to evaluate the strength of the team and market Unfortunately, this is not realistically possible for most non name-brand candidates. The company is not going to entertain the amount of inquiry (due diligence) you would need to pursue. > Evaluating the relationship between founders is as important as evaluating the founders themselves. Indeed it is! Good luck getting access to do that ... This article is just more hyperbole from triplebyte. I wonder how their business is doing ... https://triplebyte.com/careers https://triplebyte.com/careers: > We've already achieved profitablity But if I may quote from this article: > one thing we learned at YC was not to be fooled by large absolute numbers. What matters most is the growth rate. triplebyte, put your money where your mouth is and advertise your top line growth rate, not the fact that you are profitable. When your fee is on the order of $30k per hire and your infra and operating costs are low, I expect you to be profitable.

sulam 8y ago
Evaluating the strength of the team and the market is something you can do with zero involvement from the company, and you probably shouldn't depend on them to tell you either even if they offered. Getting a sense of founder dynamics can be harder, depending on stage, but it's easy if you're early enough. I interviewed at Dropbox when it was 20 people and it was obvious what roles Drew and Arash played, as an example. At a larger stage this is harder, but you have more public sources of information at that point. Regarding Triplebyte's profits, you should be asking how fast they're growing. Finally, we should all be Jeff Dean. :)

shoo 8y ago

As an "investor" you should consider the range of asset classes available to you when deciding how to invest your time and labour. See Dan Luu's articles about "big company vs startups" and "options versus cash" https://danluu.com/startup-tradeoffs/ https://danluu.com/startup-tradeoffs/ https://danluu.com/startup-options/ https://danluu.com/startup-options/

throwaway190107 8y ago

I think the author should produce some data showing this is a viable strategy before he gives people advice that could lose them hundreds of thousands of dollars. Other people have pointed out the statistical problems with this strategy so I won't restate them. The author may sincerely believe in his own advice, but we should note that he did not, himself, get rich this way. A dropout from elite UK universities, he founded a startup and exited for a small amount of money. Since then he has worked for Y Combinator, invested, and also founded a few companies. Taggar has never, himself, been anything like a startup employee. And great for him; he seems extremely talented and maybe that route isn't for him. But his company (TripleByte) profits from directing talented people into these kinds of companies.

Harj 8y ago

Rather than treating predicting startup success as an intractable problem, I think anyone considering joining a startup should act like a startup investor making a bet on how much the value of equity in that startup will grow over time. Startup investors do this for a living and that's essentially what you are too. You're investing your time and they are investing money.

wolco 8y ago
Place multiple bets over the years
arachnids 8y ago
Hrm, the parallel feels really forced to me. You can invest money in multiple startups at the same time, to hedge your bets. You can't do that with your time if you plan on working full-time.
- Harj 8y ago
  Sure, you can't diversify in parallel but you can in series.
  - chrisbennet 8y ago
    Considering how long you would have to stay to get anything from an equity event (4-8 yrs?) you realistically can't work for 10 startups. If you luck out and work for one that does have some success, you will probably find that, unlike a VC, you don't have "2X preferences" or an anti-dilution arrangement so you get nothing or next to nothing. In the meantime you may have traded your youth for magic beans - putting off things like getting a house, a girlfriend, etc because you are working long hours for sub-market pay. That is the real tragedy.
    - drewmol 8y ago
      >Putting off things like getting a house, a girlfriend, etc because you are working long hours for sub-market pay. That is the real tragedy. Just wanted to repeat this for emphasis ;-)

dawhizkid 8y ago

it's funny to think of my own finances...I have a portfolio of stock from 3 startups now that has worked out surprisingly well

sharkweek 8y ago

I worked at three startups before taking the current break I'm on - one I left before my stock was worth anything (would have paid out a small amount in an acquisition), another, the stock is now worth zero, and the third has a shot at being worth about a year's salary if current late-stage valuation is to be representative of a potential buyout/IPO (I'd say odds are alright this will happen). While I try not to think about it, because honestly the experience was worth it, I would have made far more over the last eight years of my career staying put at BigCo. With that being said... All three times, despite considering myself a pretty rational person, I got this strange psychological delusion when joining the startup that it was going to somehow magically make me rich. I think it's probably the "honeymoon" stage of joining any company. Things are awesome! The culture is fast-paced, chaotic, and offers plenty of opportunity! This is a rocket ship! It kind of matches the "what if" feeling of buying a lotto ticket. It's impossible not to imagine what might happen. I think if I jump back into startupville, my cynicism toward the "get-rich-fast with these private options" will outweigh the bright-eyed, bushy-tailed sensation of my 20s.

dawhizkid 8y ago
IMO there's only two paths that really makes sense now when considering a private co. Either a) join super early (e.g. penny strike price) with a meaningful % of total company (at least 10 bps) OR b) join late stage growth co that offers RSUs over options (e.g. "Softbank" stage cos). Joining a "middle" stage co where you are offered expensive options is the worst, since you've missed out on the early upside and you take on a ton of risk due to cost of exercising.
- joshe 8y ago
  Sorry have to delete these, not comfortable with these comments sitting on the internet forever.
  - dawhizkid 8y ago
    That is not true. You keep whatever you vest (i.e. typically stay at a company at least 1 year). That is the same for stock options. Typically companies that offer RSUs have achieved scale (your Ubers and Stripes of the world), so yes the upside is lower, but the "pros" are that it's more obvious to you what the value of the grants are and you don't have any cost to exercise them like with options. These companies know that because they are less liquid vs public cos that candidates are right to discount them, which is why they usually offer more than what you'd otherwise receive from a Google or FB.

acconrad 8y ago

This is how I've approached joining the last two companies I've signed on with. In the hiring process I ask to speak with finance and the founders to see if the company has the legs to be a real rocket ship. Remember that an interview is just as much about them interviewing you as it is for you to interview them.

davidw 8y ago
How likely is it that you as a potential employee get to see the books and know what's going on like that these days? Honest question; seems like it's a tougher thing to get access to than for a VC, but maybe I'm wrong.
- wolco 8y ago
  They (founders),are use to showing investors so it has never been an issue. Don't try the same with a small business. You will probably get kicked out.
  - maxxxxx 8y ago
    I have asked several companies about financials and they never gave any meaningful information. I got the impression that as an employee you aren't supposed to ask any questions. This is acceptable only for investors and upper management.
    - wolco 8y ago
      The companies who were open were the ones who options/shares became worth something from personal experience. The ones who hide those details had worthless options.
- lifekaizen 8y ago
  The article is mainly about revenue growth, and any startup should be willing to share top line revenue and growth rate. A large reason not to share things is some info is sensitive, for example the share count is a useful number, while the full cap table with each investor’s pricing, terms, and contact info, and other employee grants, would be sensitive and might be more guarded. Same thing about total revenue versus the customer list. More traditional advice is to ask about the fully diluted share count, so you can see what percentage the options would be, and of course the vesting schedule and purchase terms. Also I’d also ask about cash or runway, which is related to the ability to survive a rough patch. I was CEO and founder of a YC funded startup and have some experience hiring at the seed stage. For me personally, I wanted engaged people and asking good questions was a positive sign.

pembrook 8y ago

This kind of advice is similar to the "get rich day trading stocks" narrative. It only sounds realistic if you are ignorant of the statistical probabilities involved (it seems most people are). A vast majority of VC funds produce weak or negative returns. And this is after diversifying their fund investment across 10+ start-ups and assuming that 90% are going to be losers compared to putting that money in public equities. You can't work for 10+ companies at once like a VC can. And even if you could, the odds are still against you. The idea that you'll be able to pick ONE winner at an early stage is, quite frankly hilarious and naive.

jacquesm 8y ago
Another major reason that you won't be able to pick the winner is because you only get to pick once, and then you are booked for a long time. If you think a better one comes along you now have a sunk cost, and you'll be starting all over again, with a very good chance that your 'better' one will end up being worse. So the odds are very much against you if you are evaluating start-ups serially. The better way to do it is to evaluate a whole pile of them at once, and then to pick the best one that you can find. And you're going to have to do a lot of work to evaluate those options, about as much as though your future depends on it, because it does. If you're not prepared to put in that kind of work then it really is just a lottery, and you're most likely better off to just take a job that pays you roughly what you are worth on the market, in the longer term that + a good savings regime will be a much surer path to some serious cash than buying lottery tickets at an opportunity cost of 300-500K each.
echevil 8y ago
I think the right way to think about this problem is treating picking the winner at an early stage as a probability. Even though the value of the probability is small, you'd still want to maximize it when you're picking a startup to join, and you can do much better than picking randomly. You can continue to evaluate the probability after joining a startup.

artiscode 8y ago

I accepted early on that working for a startup will probably not make me rich. Quite the opposite, I may wake up one day and find out that I no longer have a job or my next salary isn't coming. I'm not the kind of person who believes in gambling. Working and living in Europe doesn't really help with the vision that I might join a European unicorn startup, whose stocks might not be worthless one day. However I do see a lot of benefits that come with working for a startup. You can voice your opinion and be heard. Pushing code to production on your first day. Owning what you do and being able to make decisions. Creating your own environment in which you can learn and become a better developer. And, most importantly, startups are more open to remote than BigCo Inc. Monetary compensation might be less, but freedom has a price. If I'm able to work remotely, I can move to a place that is cheaper to live.

fyfy18 8y ago
Most of the startups I've come across in Europe usually pay at or near to market rates. Maybe it's just my experience (I've mostly been working as a contractor), but I find this somewhat surprising, given that the social structures here mean that taking a risk by working unpaid/lower pay for a startup isn't such a big issue.

kbutler 8y ago

By working at twenty of them, expecting 15 to fail, 4 to not completely fail, and one to go big?

kelp 8y ago
This is about my career. 8 startups, earlish employee at 6. 1 mediocre IPO, and 1 very successful IPO. The rest basically failures or zombies that made me no extra money. Probably a little more lucky than most.
- dabockster 8y ago
  Tons more lucky than most. My last startup job misclassified me when funds got tight. A friend of mine who joined later never got paid (good luck filing a wage claim in WA state if L&I’s system still thinks you’re a contractor).
  - kelp 8y ago
    Perhaps also luck, but I’ve managed to have a spidy sense for when things are going the wrong way, and got out / moved on before it got that bad.
    - freedomben 8y ago
      What are some of the signs/symptoms that trigger your spidy sense?
      - dabockster 8y ago
        The big one for me was realizing that my boss had lied about knowing how to code. Other red flags include code and documentation quality, how the business sells itself to potential customers (does it greatly oversell it’s abilities), the expiration date of the coffee/tea in the break room (I got food poisoning when I drank the startup’s three year expired tea - the founders were still wondering why they felt like crap all the time when I left), etc. It’s really a bunch of little things that, when seen as off all at once, will trip your spidey sense to jump ship.

mrnobody_67 8y ago

Best risk-reward is VP or SVP level at Series C or D company which gets you options for 1-2% of the company... switch every 18 months to diversify and build a portfolio but negotiate 10 year exercise window on your options when you leave rather than the standard 90 days. Thousands of execs doing that around Silicon Valley working through Daversa and other executive recruiters (who themselves get $85K-$100K per executive hire).

BadassFractal 8y ago
That's what I hear too these days. The risk/reward sweet spot in the Valley apparently is either VC (collect management fee for a few years, don't have to show results for a while) or what you said, which is being an executive at a 50+ person company that's shown a very strong trajectory of revenue growth.
kkotak 8y ago
I can't upvote this comment enough. The bottomline for risk keen candidates is to get in with founder's equity and risk averse (and experienced, of course) to work with a headhunter to maximize your chances of building wealth.
naveen99 8y ago
Or you could just take a non startup job for higher pay and buy 0.1% of a bunch of late stage startups on EquityZen or Equidate. No need to wait 10 years...
- deanmoriarty 8y ago
  I would advise against that, I tried to dabble with both platforms, but the markup at which those shares are sold is often incredibly high: common shares of most companies on those platforms are actually sold at prices higher than the preferred (crazy), even if such company just went through a very recent round of funding, meaning that the preferred price is pretty much the very top investors valued the company at. I honestly don't know who would buy that, the idea I got by doing some basic due diligence on those deals is that who puts them online thinks "let's see if we can attract some dumb money to give us some liquidity at an insane premium". If you sell things at a fair price (e.g. selling common shares at the preferred price * 0.8, depending on the current stage of the company), investors will want to give you liquidity way before your offer on equityzen gets accepted and pollutes the cap table (I speak from direct experience), so what's left on those crowdsourced platforms is many times overpriced garbage.

dabockster 8y ago

TripleByte is a hiring agency with a financial interest in placing people with startups of all sizes and financial states. This information should be taken with a grain of salt.

kkotak 8y ago
And in my experience they focus solely on tech IC candidates, which is not for everyone.
- dabockster 8y ago
  I’m out of the loop. What do you mean by tech IC candidate?

sampo 8y ago

The author writes from the point of view of an investor. How likely it is that as a candidate for a job, they would give you all that service and access to all that information? A meeting with all the founders? Unless you're a valued, seasoned industry veteran, joining a very early stage startup founded by 20-somethings, would you really be able to access all that the author suggests?

BadassFractal 8y ago

Naive question: why not work for a FAANG, try to make close to half a million after enough time, promotions and jumping ship between the different firms, then just invest whatever you're not spending into the stock market or whatever other assets you choose? Take the 400k you're not spending and dump into Tesla and friends, or whatever other sexy stock du jour? Seems like a much healthier risk profile unless you ONLY want a huge Google-like unicorn outcome as an early employee.

sciencewolf 8y ago
It is much easier to get a job at a growing VC-backed startup than a FAANG.
- BadassFractal 8y ago
  I suppose so. That could be one's foot in the door for a FAANG role later down the line?
owyn 8y ago
If you can, you probably should! I've come to believe that the best chances of getting a financial benefit (as opposed to just an experience benefit) from working at a startup is to be a founder. If you're "just" an engineer, it's unlikely to be worth it.

takanori 8y ago

I found these questions to be pretty interesting https://medium.com/@therealpankaj/interview-questions-to-ask-a-startup-ceo-cf04d71752e8 https://medium.com/@therealpankaj/interview-questions-to-ask...

ken 8y ago

> It's also only by joining a successful startup early that you can get remarkably steep career trajectories, like Jeff Dean, Marissa Mayer or Chris Cox. The number of people with these sort of "career trajectories" is vanishingly small. This reminds me of what Phil Greenspan wrote (2006?), mocking the college student's career evaluation process: "I can't decide if I want to be a scientist like James Watson, a musician like Britney Spears, or an actor like Harrison Ford."

lpolovets 8y ago

An aside to this article: along with thinking like an investor, you can also reach out to investors who will often be willing to help with your job search. For example, as a seed VC there are now about 80 companies at various stages that my fund works with. If someone emails me and says, "I'm a good engineer who wants to join a Series A startup in SF or Oakland that has characteristics X, Y, and Z," there's a good chance I can make a few useful recs. There's nice incentive alignment here: the VC doesn't get any compensation, they just want their companies and the prospective employee to do well. That means 1) we won't recommend a bad fit to an employee because we want the employee to join and be happy and get their friends to ask us for company recs; 2) we won't recommend a bad fit to a company because we want founders to like us and not feel distracted by us. We're going for quality, not quantity -- and you're welcome to ignore our suggestions. So if you're good at what you do and are looking to join a startup, consider soliciting recs from a few investors with large portfolios. I wrote a short post about this a few years ago: https://www.codingvc.com/using-investors-to-find-the-ideal-startup-job/ https://www.codingvc.com/using-investors-to-find-the-ideal-s... I might regret posting this invite on HN, but if you want to join a startup and want recs, my email is in my blog's header.

tinyhouse 8y ago

Some good points there. A couple of things to add from my experience. The asking hard questions is very important. I once interviewed with a startup that just raised $3MM. You pay them a small fee and if your flight gets cancelled they find you a new one for free. I pressed the founder hard on why someone like me would buy that insurance and his answer eventually was for the same reason you buy insurance for your car or house. Once he gave me that answer I knew I'm not going to work there. And this was actually a nice startup with some good people. There are much worse startups with founders who have no clue and god knows how they managed to raise money. One founder once told me he is well connected and one phone call and people write him checks (red flag). Then there are the ones who are really shady and will lie about everything. Be very careful and don't ignore the red flags! Another important point is that you need to make sure the startup really needs you. In the past I talked with two startups that built their pitch around AI but they had very little knowledge of AI so what they had in mind wasn't really possible and even if it was, the product had millions of other things to succeed before AI was even needed. The problem is that founders sometimes focus too much about their pitch and how to impress investors rather than on their product.

tschwimmer 8y ago

The metaphor of early startup employee as investor seems really smart at first but is ludicrous in reality. It is physically impossible to choose a startup like a VC because you cannot diversify your portfolio like they can. VCs can sprinkle (relatively) small amounts of money across dozens or hundreds of startups. If one fails then the impact to the portfolio is negligible. In fact, VCs expect that most of their portfolio probably won't pan out. Good luck diversifying as an employee. Working part time at even 2 startups is obviously laughable. If you're in it for the money, working at a startup is probably not for you. It really is akin to gambling. There may seem to be more information available than gambling, but there is so much unknown and hidden information it's damn near impossible to make a 'rational' decision. That's not to say you should never work at a startup. Startups are often great learning opportunities because you usually have both broad and deep scope of responsibility. There's also often better alignment between management and employees because people tend to be working stuff that is materially relatable to the bottom line. It can also be a career accelerator if the company grows headcount rapidly and you suddenly become a 'senior person'™. YMMV.

fhbdukfrh 8y ago
I agree with you, and this was my initial response when i started reading the post. VCs also get far more information about the company and can demand way more control. How many employees of a startup get a board seat, even if you're non-founder employee #1? Even those diversified portfolios aren't going to have huge returns in most cases. I think the lesson is that if your value proposition is exchanging your skills and time for money (ie, an employee) you can't parlay that into startup style returns without essentially winning the lottery. If you can pick the next unicorn for employment purposes don't waste your talents on actually being an employee
- danenania 8y ago
  On the other side, as an early employee you can have a much bigger impact on the odds of success than an investor. If you think a company has huge potential, but it's missing X/Y/Z, and you're an expert in X/Y/Z, then you have both a unique insight and unique leverage to make a success out of something that might not have been without you. Looking for situations where you make the difference is perhaps one way to have the whole thing feel like less of a lottery.

JohnFen 8y ago

I love working for startups, but not working for startups that have VC money -- the involvement of VCs changes the nature of everything. But then, my goal is primarily to do meaningful work on interesting projects. I have little interest in getting rich.

rohithb 8y ago

Just read the conclusions, the writer is not sure what really works.

nikanj 8y ago

Being an early-stage employee gets you all the downsides of being a founder, with only a fraction of the benefits.

seretogis 8y ago

What about the Groucho Marx strategy of not investing in any company which would have someone like yourself as an employee?

nadim 8y ago

“I think startup employees should re-evaluate the growth trajectory of their startup every year.” At a bare minimum. Probably more often.

raygelogic 8y ago

the best advice I can offer is to join a team that has deep pockets. the biggest reason my company succeeded is that they had cash to burn. sure, they were smart. they moved quickly, they dropped failing products instead of holding on to them. they made consistently good decisions. but they also were able to sink millions into the company's products and promotion thereof without going under for years, long enough to stumble upon a hugely profitable model. no idea how to assess the size of a company's pockets. maybe one that has a founder who has already had a successful exit. every other attribute of a company is basically fortune telling.

general8bitso 8y ago

Which scratch-off ticket should I buy at the gas station?

throaway9999 8y ago

What's considered a good bps for an very senior engineer joining as 20th employee, at a series A company with a couple of million dollars revenue?

known 8y ago

And why startups condense in America? http://paulgraham.com/america.html http://paulgraham.com/america.html

halfjoking 8y ago

“If you're happy working where you are, and you don't have any ambition to do anything else, you're probably going to get paid less and work more if you leave for a startup. If getting paid less and working more is unappealing to you, then I would recommend staying where you are!” There's another option. You can pick a job that isn't a startup, that makes you hate your life, and phone it in every day just to get by. You save your energy and grind away at night on your own company. I say "company" instead of startup because I don't think venture capital is the right thing to pursue for a single founder doing this. Just have a goal to build a product that has at least 1000 customers paying $10/mon so you can quit your dayjob. The hatred of your dayjob will fuel your motivation to work at night. A startup is much riskier than taking this approach. You put in 60 hours a week at a startup and even in the very unlikely scenario it pays off and the startup becomes huge - at most you have a 1% stake and become a millionaire. You become a millionaire way easier working on your own project. So my philosophy is to get a job you hate - work to build the future you want yourself - never let anyone else exploit you to the point where the only way you become a millionaire is if they become a billionaire.