The metaphor of early startup employee as investor seems really smart at first but is ludicrous in reality.<p>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.<p>Good luck diversifying as an employee. Working part time at even 2 startups is obviously laughable.<p>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.<p>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.
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.<p>With that being said...<p>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 <i>might</i> happen.<p>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.
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.<p>Thousands of execs doing that around Silicon Valley working through Daversa and other executive recruiters (who themselves get $85K-$100K per executive hire).
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.<p>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.<p>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.<p>I wrote a short post about this a few years ago: <a href="https://www.codingvc.com/using-investors-to-find-the-ideal-startup-job/" rel="nofollow">https://www.codingvc.com/using-investors-to-find-the-ideal-s...</a><p>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.
> 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.<p><i>smack forehead</i> Yes, what ever could I have been thinking before! Yes, yes, I should only be joining a <i>successful</i> startup, not an average one!<p>> steep career trajectories, like Jeff Dean, Marissa Mayer or Chris Cox.<p>Yes yes! New plan: be Jeff Dean!<p>> Next, you need to evaluate the strength of the team and market<p>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.<p>> Evaluating the relationship between founders is as important as evaluating the founders themselves.<p>Indeed it is! Good luck getting access to do that ...<p>This article is just more hyperbole from triplebyte. I wonder how their business is doing ...<p><a href="https://triplebyte.com/careers" rel="nofollow">https://triplebyte.com/careers</a>:<p>> We've already achieved profitablity<p>But if I may quote from this article:<p>> one thing we learned at YC was not to be fooled by large absolute numbers. What matters most is the growth rate.<p>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.
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.<p>So there's a few considerations:<p>- 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.<p>- 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.<p>- 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.<p>- 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?
> 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.<p>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:<p>"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."
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
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.
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?<p>Seems like a much healthier risk profile unless you ONLY want a huge Google-like unicorn outcome as an early employee.
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.<p>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.<p>And, most importantly, startups are more open to remote than BigCo Inc.<p>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.
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.<p>The author may sincerely believe in his own advice, but we should note that he did not, himself, get rich this way.<p>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.<p>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.
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 <i>them</i>.
,,It's also only by joining a successful startup early that you can get remarkably steep career trajectories, like Jeff Dean''<p>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.
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.<p>Does the work look interesting? Will you learn new things?<p>Do you like the problem space the startup operates in?<p>How is the culture? Fit or not?<p>Will you be happy there?
Some good points there. A couple of things to add from my experience.<p>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!<p>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.
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?<p>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?
I love working for startups, but not working for startups that have VC money -- the involvement of VCs changes the nature of everything.<p>But then, my goal is primarily to do meaningful work on interesting projects. I have little interest in getting rich.
“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!”<p>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.<p>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.<p>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.<p>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.
As an "investor" you should consider the range of asset classes available to you when deciding how to invest your time and labour.<p>See Dan Luu's articles about "big company vs startups" and "options versus cash"<p><a href="https://danluu.com/startup-tradeoffs/" rel="nofollow">https://danluu.com/startup-tradeoffs/</a><p><a href="https://danluu.com/startup-options/" rel="nofollow">https://danluu.com/startup-options/</a>
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.
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.<p>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.
I found these questions to be pretty interesting<p><a href="https://medium.com/@therealpankaj/interview-questions-to-ask-a-startup-ceo-cf04d71752e8" rel="nofollow">https://medium.com/@therealpankaj/interview-questions-to-ask...</a>
And why startups condense in America? <a href="http://paulgraham.com/america.html" rel="nofollow">http://paulgraham.com/america.html</a>
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?
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).<p>A vast majority of VC funds produce weak or <i>negative</i> 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.<p>You can't work for 10+ companies at once like a VC can. And even if you could, the odds are <i>still</i> against you. The idea that you'll be able to pick ONE winner at an early stage is, quite frankly hilarious and naive.