
How to Choose a Startup to Work for by Thinking Like an Investor - Harj
https://triplebyte.com/blog/how-to-choose-a-startup-to-work-for
======
tschwimmer
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.

~~~
econner
The best part is stock options. Not only are you not diversified, now you get
to concentrate your portfolio by buying stock in the company that provides
your income.

Stock options: for concentrating your income and your investments when you're
excited and biased.

~~~
JohnFen
Decades of experience has taught me that stock options are essentially
wallpaper. Sure, if a company wants to give me options, I'll take them -- but
they are in no way a substitute for real compensation, and I won't accept them
in lieu of something real.

That said, if a startup is doing something that really turns my gears and I
like the company, then I'm absolutely willing to work for less pay in order to
be a part of that.

~~~
deanmoriarty
Something I never understood about this attitude ("... then I'm absolutely
willing to work for less pay ...") is: why there are almost no examples of
such behavior in other highly paid professions, such as physicians or lawyers?
Very rarely you'll find physicians saying "I really want to become a brain
surgeon, I'll happily take 40% less than my market rate". You'll certainly
find physicians doing volunteering, but that's another thing.

In software instead, that's incredibly common: several of my coworkers (late
stage private company) are in mostly for the thrill of working on our
technology since we operate in some interesting niche, and I know for a fact
they are paid much less than me (30%+), even if they have a bigger impact than
me on the company (and they are also older, with more experience!).

It's so common that many times employers use it at their advantage, by
preferring people that can be sold purely on the tech rather than the tech AND
the market rate for the position.

To me, both the financial aspects and the technical challenges must be
absolutely satisfied in order to join a company. Maybe I'm too practical
because I'm not a trust fund kid and grew up dirt poor, so I know that in my
limited ~20y engineering career (assuming ageism) I need to make enough so
that I will be able to retire comfortably, while making sure I work on stuff
that stimulates me so I can give my very best.

~~~
the_jeremy
I think there are. Teachers (pretty much as a whole) and public defenders seem
to fit here.

I know multiple photographers whose passion is landscapes/nature and only
grudgingly supplement that income with weddings/portraits.

~~~
deanmoriarty
With regards to teachers or photographers, that's not a fair comparison in my
opinion: in those cases, low wages are mostly dictated by high supply vs low
demand, so from an economic point of view it "makes sense". That's much
different than software engineering or medicine, where there is a scarcity of
supply (and the only reason why software salaries are in the 6 figures).

In other words, teachers are not willingly giving up a portion of the
compensation that they could otherwise be making doing the same job somewhere
else. In software instead, that happens ("Oh, you work on FOO v2.0, I'll
happily take 40% less than what I could otherwise be making doing this job in
another company").

I don't know about public defenders, you might have a point there.

~~~
apersona
From my perspective it looks like a good amount of teachers decided to give up
a portion of the compensation _earlier_ (i.e. they gave up good pay not when
they're looking for another job in an industry they're already in, but they
decided to give up good pay upon joining the industry).

It's like how artists/writers/game developers/etc. decide to go into their
field even though they know that they could be making much more money in any
other field.

------
sharkweek
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
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.

~~~
icedchai
I wouldn't consider 10 bps (0.1%) meaningful. Early stage is very, very risky.

~~~
nostrademons
Depends if it's pre- or post-product/market fit.

Joining a startup that's overwhelmed with demand for its product -
particularly if you can see the usefulness of this product yourself - is
usually a good move even at 0.1%. Joining a startup that's still iterating on
the product (and maybe has a couple customers but just lost a big one and they
have to work really hard to sign the next one) may be a bad move even at 10%,
because there's a good chance that equity will be worthless.

The article doesn't really mention it, but a great question to ask any
potential employer is "What are your biggest problems right now?" Scaling is a
_great_ problem to have, because it indicates lots of demand and has solutions
that are relatively well-known in the industry. Customer service is a pretty
good one - it shows that the company has customers who care enough to want
service, and if the CEO is willing to admit this is a problem it'll probably
get fixed. Hiring, code quality, internationalization, testing, service
outages, brain-dead tech stack, anything that's specific to the problem domain
itself - these are also pretty decent problems to have as long as the CEO is
attentive to them. Unhappy customers or staff turnover is a caution - you
should dig into this further to see _why_ they're leaving, and if it looks
like the problem is solvable. Same with financing - many hot companies run low
on cash at various points, and you only need to make sure the company isn't
going to die, but if the company loses more money than it makes on each
transaction that's a huge red flag. The biggest problems (particularly for an
engineer) are anything to do with sales, marketing, partnerships, or "growing
the business", because the root cause of this is often that customers don't
really want what you're making, and nothing short of a major pivot fixes that.

As a side bonus, asking this question is often a big positive signal for the
hiring manager, because it shows you're serious about solving problems rather
than just collecting a paycheck.

~~~
icedchai
Yes, I agree. I was assuming "pre-market fit" "few or no customers." In this
case, 0.1% is hardly worth the risk.

------
mrnobody_67
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).

~~~
naveen99
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
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.

~~~
naveen99
well, getting shares as an employee is even worse. You still get common
shares, usually with some trade restrictions / lock up period on top of it...
The price / premium on the secondary markets is a market price, and in a
market that is more efficient than it used to be. Also, the person selling
those shares may be an early employee who has many other reasons to sell than
screwing the buyer...

------
lpolovets
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-s...](https://www.codingvc.com/using-investors-to-find-the-ideal-
startup-job/)

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.

------
techslave
> 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
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. :)

------
lordnacho
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?

------
ken
> 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."

------
qaq
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
Yeah, a key strategy for investors is to diversify, and that's exactly what
startup employees cannot meaningfully do.

~~~
jcoffland
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
Neat idea, but how would you choose who qualifies to join?

~~~
jcoffland
Probably the same way a VC chooses startups.

------
dabockster
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
And in my experience they focus solely on tech IC candidates, which is not for
everyone.

~~~
dabockster
I’m out of the loop. What do you mean by tech IC candidate?

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

~~~
kelp
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
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
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
What are some of the signs/symptoms that trigger your spidy sense?

~~~
dabockster
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.

------
BadassFractal
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
It is much easier to get a job at a growing VC-backed startup than a FAANG.

~~~
BadassFractal
I suppose so. That could be one's foot in the door for a FAANG role later down
the line?

------
artiscode
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
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.

------
throwaway190107
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.

------
acconrad
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
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.

~~~
jacquesm
That depends on what the company is looking for in you. If you're going to do
mission critical stuff or they want you for an important role they might even
enjoy showing you their internals. And if they don't want to show you then
that's a pretty good indication that you are probably better off elsewhere.
Transparency in an early stage start-up is good for everybody, including the
founders. If founders are not willing to share their position they are
effectively asking you to buy a cat in a bag.

~~~
ryandrake
No private company I have ever worked for as an employee has agreed to let me
look at their balance sheet or income statement. Most would not even discuss
valuation in terms other than # of shares in my offer, which is meaningless.

One CEO I recall even laughed when I asked at the interview (that should have
been a red flag in retrospect). I later learned he gossiped about how
inappropriate it was for a candidate to ask about company financials.

~~~
maxxxxx
Same here. This information is only for investors and other "important"
people. Most of us are not part of that group.

------
xiphias2
,,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.

------
jorblumesea
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?

------
tinyhouse
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.

------
sampo
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?

------
sjg007
Choosing a YC startup is probably the best bet. If it fails you can use that
network to get into another YC company.

------
JohnFen
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.

------
halfjoking
“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.

------
shoo
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/)

------
Harj
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.

~~~
arachnids
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.

~~~
OiNG
Its not even about hedging but about diversification. If you are in a position
where you can't diversify fully, you should require a higher return on
investment in order to take on the risk.

For example. If you could bet on a coin flip 100k times at $1 a bet, you might
be willing to accept getting paid $1.01 per win. But if you had to bet $100k
on a single coin flip, you would likely need the payout to be much greater
before you were willing to take the bet.

~~~
arachnids
Both are viable strategies. You diversify when you spend time working for
startups across different sectors in the hope that some might succeed in their
own area. You hedge when you work for several competitors in the same area in
the hope that one of them will win in the end.

------
nadim
“I think startup employees should re-evaluate the growth trajectory of their
startup every year.”

At a bare minimum. Probably more often.

------
raygelogic
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.

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

------
takanori
I found these questions to be pretty interesting

[https://medium.com/@therealpankaj/interview-questions-to-
ask...](https://medium.com/@therealpankaj/interview-questions-to-ask-a-
startup-ceo-cf04d71752e8)

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

------
known
And why startups condense in America?
[http://paulgraham.com/america.html](http://paulgraham.com/america.html)

------
throaway9999
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?

------
pembrook
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
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_.

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

------
dawhizkid
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

------
general8bitso
Which scratch-off ticket should I buy at the gas station?

