
Three Paths in the Tech Industry: Founder, Executive, or Employee - craigcannon
https://blog.ycombinator.com/three-paths-in-the-tech-industry-founder-executive-or-employee/
======
nichochar
This is rather true in practice, but I find it tremendously depressing.

I have found that the executive path is actually the one that most of the
scumbags take, it is the one that attracts the most people, and those people
are usually not likable, they're salespeople that sell themselves all day.

The third group, the one that actually creates value, is accurately
represented as not as successful both in terms of money and prestige. I think
this is a damn shame, and we should be striving to stop that. This is a good
painting of how bad things are today, but instead of "tricks to game the
system" i wish it layed out a path of how to build an industry that doesn't
attract all those ambitious selfish (executives) people.

~~~
sidlls
I have a different (admittedly controversial) take, having been on the "tech
ladder" for some time now (as a Senior SWE and Lead Engineer): most individual
contributors overestimate how much value they actually provide, especially in
the Bay Area. That isn't to say we're not under-appreciated and under-
compensated (we are both). But realistically much of the time work we do is
easily done by literally thousands of other people just as well. The same just
isn't true of product development, sales and marketing. Any one of those three
teams, staffed well, will account for well more than the value of the entire
engineering organization.

Mostly this is a self-inflicted problem. Especially in the Bay Area, where
developers tend to value CS ability signaling rather than the ability to work
well with product teams and the ability to engage in practical engineering.

There's too much focus by developers on shallow things, like fad-following the
latest frameworks, on pseudo-intellectualism or technology-purism (e.g.
"coding is doing math", code "elegance", whether/how FP is just so much better
than anything else, etc.), and trivia like programming language choice.

~~~
kartan
> The same just isn't true of product development, sales and marketing. Any
> one of those three teams, staffed well, will account for well more than the
> value of the entire engineering organization.

Why is it not true for them? Sales are not magic, it is a profession that can
be learned. I have seen a lot of companies stating how important is sales, and
how unique they are. It can't be true for all companies. It is like everyone
thinking that they are above average, it is just not possible.

If your product is software, literally it is impossible that sales add more
value than the engineering organization that builds the product. Without
engineering organization, you don't have anything to sell. Without sales and
marketing, you will also have a hard time. It is collaboration what brings
success.

> There's too much focus by developers on shallow things, like fad-following
> the latest frameworks, on pseudo-intellectualism or technology-purism

This is usually a problem with recruiting. You get what you pay for. If your
interviews are about technical expertise and you ignore basic persona-values
evaluation and fit to build valuable features, you get that. And it
jeopardizes the viability of a company. You need some really good experts, but
you don't need everyone to be one.

~~~
slg
>If your product is software, literally it is impossible that sales add more
value than the engineering organization that builds the product. Without
engineering organization, you don't have anything to sell. Without sales and
marketing, you will also have a hard time. It is collaboration what brings
success.

The distinction is that product development, sales and marketing can act as
multipliers in a way that engineering seldom does. A tech company's growth is
rarely due to the technical excellence of their product. There are obvious
exceptions at the extremes, but very few of us are working for a Pied Piper
with some truly amazing competitive advantage in technology.

For example, what would happen if magically Twitter's tech became 50% better
overnight? That would certainly reduce costs, but would it lead to any growth?
Would the average person use the service more if the tech was better? Would
companies buy more ads? Would revenue increase?

Now imagine their product development, sales and marketing teams became 50%
better. They could have actual product improvements beyond doubling Tweet
length. They could instantly sell more ads. They could increase external
partnerships to bring more attention to the platform. They would have all
sorts of opportunities for added revenue and growth.

~~~
mehrdada
> _sales and marketing can act as multipliers in a way that engineering seldom
> does_

(I cannot distinguish product development from engineering as cleanly as you
do, but on sales and marketing...)

Can't disagree more. At least with the definitions I have in my head, this
sentence is logically inconsistent with such definitions. Engineering is _the_
way you get non-linear leverages. Sales and marketing, almost always give
linear multiples at best.

I feel once you have the "golden goose" leverage delivered by engineering in
hand, you start calling it sales because that's the final step in conversion
to $$$. Also, that's when the linear multiple provided by sales and marketing
is the biggest in absolute numbers.

[But yes, if you call everything you see as "marginal contribution"
engineering, and everything valuable "product development", then you
tautologically "prove" your conclusion.]

~~~
kamakazizuru
interestingly, a lot of enterprise Saas software is "sold before its built",
by which i dont mean its complete vaporware, but its a very common practice to
build a shitty first product, sell sell sell, and only after the first 10-20
customers are on board, do these companies start to spend more on engineering
etc. Even after that, in order to sustain the machinery of building product,
you need to keep selling. I think both are important, but in the technical
world we tend to seriously underestimate how important sales it. At the end of
the day, you can have the best alogrithms, the most elegant code and the
sexiest UI, but if you dont have someone taking it to customers, and bringing
their feedback back, all you have is a beautiful product without a business.

~~~
subway
This is exceedingly common. It also makes a helluva lot of people miserable.

------
reuven
How about freelancing? I've been doing that since 1995 -- and my income and
happiness have never been higher.

Pros: \- Work on what you like, with the people you like \- Potentially very
high salary, definitely more than you would get as an employee \- Want to work
on side projects (e.g., software, books, and courses)? Go for it, and benefit
from multiple income streams.

Cons: \- You're running a business. That requires time, as well as
skills/knowledge (often learned the hard way) that are completely separate
from programming. \- You have to market yourself (until you're good enough
that people contact you). No marketing, no work. No work, no salary. \- It's
harder to do when you're married and have children. (I started when I was
single.)

In many ways, freelancing is like the "founder" described in the article.
However, the article also talks about teammates and a financial plan
(including funding). Plenty of successful freelancers make good money just by
themselves (or maybe 1-2 junior people). And I definitely never intend to take
investment money.

Not everyone is cut out to be a freelancer. But it's a very viable option,
beyond being a founder, executive, or employee. And I can tell you that many
of the founders, executives, and employees I meet as I travel the world
teaching Python are quite jealous of my satisfaction.

~~~
s73ver_
Cons: Insurance and pre-existing conditions.

Not to put a damper on your post, as it sounds like you have had good success.
But this is a very real thing for many people. When I graduated and went out
into the world, I needed insurance, and this was before the ACA, which meant
that my pre-existing condition was not something that would be insurable, at
least at any decent rate. The ACA fixed that, but now you have the GOP
attempting to return things to how they were before, especially for pre-
existing conditions. They failed now, but they're not going to stop. So, for
many people, currently the climate is not one where they could go without a
group plan that they'd get at their employer.

~~~
mgkimsal
Getting political for a moment... it's disturbing that we've had health care
fundamentally tied to employment (in the US) for decades now. I don't quite
know how you break this down. I wouldn't think it has to be 'single-payer' to
get past this but... I don't know.

> for many people, currently the climate is not one where they could go
> without a group plan that they'd get at their employer.

It's been this way for decades. 20+ years ago I remember talking to people
about freelancing, or starting their own business, and the same reasons came
up "Oh, i've got this medical condition" or "we can't afford to lose this
insurance".

I can't speak to the 60s or 70s, but for the bulk of my adult life where I've
been aware of this issue, it's been like this. :(

~~~
eru
> I wouldn't think it has to be 'single-payer' to get past this but... I don't
> know.

For a start, eliminate the tax discrimination that makes employer paid health
insurance cheaper.

~~~
mgkimsal
From a tax standpoint, as an independent contractor, my premiums are 100%
deductible. But I don't get any sort of 'group rate' discount.

~~~
eru
But for regular employees there's a different tax treatment when they pay for
their own health insurance, isn't it? (Not an American myself.)

~~~
mgkimsal
I have to assume their is, if you're purchasing directly for yourself, but are
also considered a full-time employee of an employer that doesn't offer it to
you.

Hrm... found this, to explain it...

[http://www.healthedeals.com/articles/are-health-insurance-
pr...](http://www.healthedeals.com/articles/are-health-insurance-premiums-
deductible)

" if you’re self-employed and claiming the self-employed health insurance
deduction on Form 1040, you don’t have to exceed the 10 percent mark. That’s
because you’re writing the premiums off as an adjustment to your income rather
than as a deduction."

This is what I do.

The standard approach many folks take is to "take a deduction" (which occurs
at a different point in the tax calculating) - and for that, you can only
deduct any amount that exceeds 10% of your "adjusted gross income". In my
case, I'm adjusting the gross income by deducting the insurance expense there.
That may only be something I can do because I'm not an employee of anyone? I
do this every year and it's still confusing as heck to me.

But the original point stands - anyone that is purchasing health insurance
should be able to not pay any tax on the premiums. Or... no one should be able
to(employee, employer, freelance). Level playing field theory and all that
jazz...

------
jedberg
The advice I always give to a new college grad is try and get a job at one of
the big tech companies.

The work and the mission may not be exciting, but there is huge room for
growth and often the large companies have programs especially designed for
career growth for new college grads.

But don’t get stuck. The job will comfortable. After a few years it’s time to
move on. Maybe you’ve found a few folks to cofound with, or maybe you just
have a good lead on a much bigger role. But the only way to really advance is
to leave — most big companies have artificial limits on salary growth and
promotions. You can always go back later.

~~~
eradicatethots
It sounds very stressful to work at a major company

~~~
arthurjj
Eh. Having worked at a Defense Company, a unicorn and then a Big 5 tech
company I can honestly say the work life balance is probably the best at the
the Big 5.

At Defense companies you're both clearly a cost center and a cog in an
unfathomably large machine. Imagine a combination of Kafkaesque and Chtulhu.

At a Unicorn. You learn a lot but only because you work insane hours. Also
you're paid under market wages because your job is sexy.

~~~
oakswood
Very much agree here. I've done the same to a lesser extent (defense
contractor, maybe a Big 15, failed startup, and then freelancing).

Freelancing is pretty good in terms of work-life balance as well, although it
can feel like an endless pursuit of finding projects (interviewing, selling
yourself, etc)

------
koolba
Regardless of which path you'd like to go down, learn some basic financial
planning, frugality, and learn to live like a miser. It'll pay dividends, both
figuratively and literally.

Regarding the executive path, or more generally any management role, learn
early on if it's for you. If you're the type that gets caught up in human
interest stories, considers it inhumane to fire low performers, or generally
believes in a sense of fairness to the world then forget about it and stick
with being an employee. It's better for your own sanity.

~~~
krat0sprakhar
For someone who recently graduated and quite clueless about financial
planning, do you have some resources to get started?

~~~
koolba
The usual generic financial advice I give is:

\- Maximize every retirement vehicle offered to you (max 401k, HSA, etc).

\- Pretend that any money you sock away for retirement doesn't exist. This is
best done with automated withdrawals so you never even consider it money in
your checking account.

\- Learn to cook. This doesn't actually save much money at the individual
level but is huge for families.

\- Set up separate accounts for expenses and savings. Most payroll setups
allow you to automatically divert funds to multiple accounts. This lets you
automatically put $X in your expense account and $TOTAL - $X in the savings
account. Again, the idea is to never consider that money spendable. It goes
into a lock box.

\- Shoot for a 50+% after tax savings rate. It sounds nuts but it's actually
easier than you think. The key is to not bump up your expenses as your income
increases. You might not be there when you first start out but if you're
increasing earnings 5-10% per year you'll get there quite quickly
(particularly in tech).

\- Never buy a new car. They're for chumps.

\- Never lease a new car. That's for the biggest chumps.

\- Once you've built up an 8 to 12 month nest egg of reserve cash, start
allocating the rest in a diversified portfolio. Pick securities from the
trading company that don't have transaction costs (large discount brokers
usually have in house mirrors of popular ETFs for this).

Stick on this path and you'll eventually be sitting on a decent nest egg. Plus
if you've reined in your expenses, if you decide to go the founder route
you'll have plenty of runway to pursue your ideas.

~~~
defined
> \- Never buy a new car. They're for chumps.

> \- Never lease a new car. That's for the biggest chumps.

Disagree on the leasing if you have your own company. The lease payments are
all interest and deductible from your income. Sure, you don't end up with a
car but if you do a 36 month lease, your new car is under warranty the whole
time.

I've seen too many people suffer from the false economy of used cars. If you
are lucky (or a skilled mechanic), you can benefit, but if not, the repair
expenses and vehicle breakdowns become a large drain.

I agree that financing a new car is just a depreciation hole, but you need
your wits to avoid being screwed over when getting a used car. You just never
know what's been done to it.

~~~
nilkn
> I've seen too many people suffer from the false economy of used cars

Just get a 1-2 year old low-mileage CPO vehicle. It should still have the
original warranty active. Ideally you should also target brands with great
warranties like Hyundai (100k miles/10 years). This is as far as I can tell
close to the optimal financial strategy for car ownership.

Personally, though, I do buy new, and I pay cash so I never, ever have a car
payment. I hate the feeling of paying off a car over years as it depreciates.
I really prefer to just get it over with and then enjoy knowing that I totally
own it, no strings attached.

------
harryh
I liked this essay better when Venkatesh Rao wrote it in 2009.

[https://www.ribbonfarm.com/2009/10/07/the-gervais-
principle-...](https://www.ribbonfarm.com/2009/10/07/the-gervais-principle-or-
the-office-according-to-the-office/)

~~~
pavlov
This should be the top comment. Three paths indeed.

------
Chiba-City
I founded a company that helped many other 90-00's founders along with some
legacy industries in crisis. I am a reader so I read many business books. But
I missed two specific dynamics I wish I had known earlier.

First, executives will routinely attempt to take the founders' roles.
Industries vary widely, but they are roughly "showy spenders" and not savers.
Many have no experience in new ventures. They have ridden high and will panic
against adversity. If they cannot flee in an overall industry downturn, they
will feed on the founders. Be very careful to make "executive" expectations
brutally clear and consequences for any and all hubris terminal.

Second, many founders want to be 1-hit wonders. Unlike our industry ecosystem
building heroes, they are neither in the ecosystem nor interested in
developing the ecosystem. They want in to get out ASAP. Their short termism
sadly translates into teaching bad examples to employees.

Nevertheless, the information rich life of the "small rooms" where plans are
crafted and industry roads remapped on whiteboards are truly the most
wonderful teachers anyone can expect to access.

~~~
shostack
> "Be very careful to make "executive" expectations brutally clear and
> consequences for any and all hubris terminal."

Any examples of how to "do it right?"

~~~
Chiba-City
I wish I had a clear answer. We have to be nice enough to people, but we have
a world of needy charlatans transacting for themselves with little concerns
for outcomes, responsibilities and reputations.

Here are some ideas.

IBM's head of federal sales said make hires show their past tax forms. Her
point was to remove any "cleverness" over negotiating salaries and outcome
responsibilities. Negotiate serious matters "naked." Watch details like
commute times, time consuming rituals or debt levels.

Reading and writing are paramount requisites of organizing. I would recommend
seeking at minimum faithful business press readers who are not day traders.

Seek executives who show up for smart dialog at the office. Teams have to
share the world and not just their own company. Smart people are team players
who seek correction or validation.

Seek executives who apply methods they can describe. Beware the latest
buzzword fads.

Places like SV, NYC Or BO have deep benches of worldly smarties. That worldly
wiseness is important in a startup seeking relevance to very real supply
chains in constant motion. Many job seekers at all levels are very narrow
specialists who have "rounded themselves" adapting to roles deep inside very
incestuous companies or industries. Those folks are motivated by popular
delusions of "riches" or "wonders" hiding elsewhere.

Attrition is normal. But recruiting is costly and executive attrition is super
costly for the teams and companies left behind.

Industries are all different. But enduring purpose, role and focus are good
character attributes to seek in startup hires. That's not highly prized in our
fast-transacting careless world.

------
CalChris
There is a fourth path. _Levi Strauss_.

Don't get me wrong. The gold miners needed jeans and supplies. But Levi
Strauss lived off them and not the reverse. So the fourth path is service
providers: lawyers, accelerators, accountants, contractors, ..., even VCs to a
degree. I think Silicon Valley has a competitive advantage in having the best
but it is a different path. And as much experience as they have when I talk to
them, they haven't done it themselves.

Well, most haven't. Ben Horowitz knows. Some know but most don't. That doesn't
keep them from doing an awesome job. It's just a different path.

~~~
lalos
That would be a founder solving a specific problem by providing a service.

------
simonbarker87
Can a failed, or mildy successful, founder jump to the exec track and get some
level of success faster than if they had just set out on that path to begin
with? I’m thinking of those people who have run a business for 3+ years before
it tanks or who are looking for a new thing and just decide to leave

~~~
k__
Isn't this the default route for failed founders?

I know a bunch of them now leading some divisions or branch offices.

~~~
simonbarker87
Was thinking the default route would be to try again but if they didn’t would
it be a _faster_ way to climb to exec

~~~
k__
I don't know...

It seemed to me that most people aren't 'serial entrepreneurs' they just heard
of the success of SF tech founders, tried it at home, failed, marked it as
something they weren't made for, went for a simpler job.

Also, some get a family and start to avoid risk.

------
lliamander
When considering these different paths, it's also worth considering the kind
of temperament one needs to have to be successful in each role.

Founders, from what I understand[1], tend to be high on the Big 5 Personality
trait "openness", which has to do with creativity. Executives (and employees
to an extent as well) who are successful tend to be high in trait
"conscientiousness" which has to do with being hard working and orderly.

[1]
[https://www.youtube.com/watch?v=P830JMVeKLo](https://www.youtube.com/watch?v=P830JMVeKLo)

------
JimboOmega
My experience has been that jumping from employee to any level of executive is
the absolute hardest step, at least for me.

I think once you are a team lead and have some number of direct reports, you
can then start jumping your way up that ladder. But going from 0 to 5 direct
reports has often seemed impossible. I'd be open to tips on how to do it.

~~~
sshumaker
A manager isn't an executive. In addition to new skills, there are also mental
shifts necessary at various stages in your career, as you climb to increasing
levels of leadership.

You can see this on the IC track as well for top-tier tech companies - there
is a step-function difference in mindset at certain levels.

Jumping from IC to line manager, as you suggest, is one; you need to recognize
you are no longer shipping code but are shipping your team - they are your
output, and their performance is how you are measured.

At director it switches again, you are responsible not precisely for the
people but for your organization as a whole. There is an adage that you know
you're a director after your first re-org and are moving people's names around
as cells on a spreadsheet.

It changes again at VP, as an executive of the company you are responsible and
accountable for an entire function. Excuses cease to matter, even external
forces - you should have accounted for them. You are optimizing for the
company's overall future and not your org or people.

This is a vastly simplified explanation, obviously.

~~~
JimboOmega
You're saying what's necessary to do the job, not what's necessary to get it -
which is my bigger problem. I don't feel that I want to remain an IC forever;
become a true technical expert and honing that skill further is not a path
that I personally want to focus on

~~~
shostack
The way to break free from the IC mold generally takes a combination of a few
things:

1\. Interest in growing which you make known to those above you.

2\. Available positions (hard to grow into a manager when there is no manager
role available or budget to support one)

3\. Understanding the difference between "strategy" and "tactics." They mean
very different things, and as a manager, depending on the size company, you
may be responsible for setting the strategy while your team executes on
tactics.

4\. A demonstrated willingness and ability to put the company first and
protect it. There is a lot of debate on this one and what it means, but
generally those who do this get ahead faster than ones who don't, regardless
of your viewpoints on whether that is right or not.

5\. A growing focus on process and where you team fits in with the rest of the
company. By focusing on this, you can find ways to improve team efficiency and
performance, and better interface with other departments. As a manager, your
job is literally to improve the efficiency and performance of your team and be
the glue to other teams.

------
peterburkimsher
My dad refused promotion at CERN several times. He continued to work as a
testing engineer, and would not climb the corporate ladder into management
roles. That reduced his paycheck.

When the company had financial trouble though, they fired all the middle
managers and kept the engineers. He learned an important lesson - working at a
low level with only machines below you is a safe and stable job.

I want to do the same. I'm now 28, so I have plenty of flexibility. But I'm
worried that as I get older, there will be more pressure to go into management
instead of staying in engineering. Companies want fun, young engineers who
know all the latest tech - they don't want experience at the technical level.

~~~
gaius
_When the company had financial trouble though, they fired all the middle
managers and kept the engineers_

The truth is that most layoffs don't work like that, unfortunately. Members of
the management class will generally try to protect their own, and they see
engineers as mere blue-collar workers, no matter how skilled or qualified
those engineers are. Yes, even software engineers.

------
austincheney
> The last thing I’ll say is it takes time to be good at each role. When
> you’re in college there is this idea that you should take your 20s to
> discover yourself and the find the work that is most enjoyable to you. The
> problem is that if it takes 5-10 years to truly get good at something and
> you spend 10 years discovering what you want to get good at…it’s going to
> take a long time for you to feel like a highly skilled productive person
> (and to recieve the rewards that come with this). It’s not that you
> shouldn’t explore, it’s that you need to understand the costs of that
> exploration and plan accordingly.

\---

This is an understatement that I see many new or junior developers completely
missing. You don't magically become a rockstar. Working with rockstars is
helpful, but it won't make _you_ a rockstar. Company name/brand is irrelevant
to becoming a rockstar. It is all about practice solving hard problems, which
takes lots of time and concentration. This is the only factor that separates
the amazing developers from everybody else, and honestly most people don't
have the discipline or personality to get there.

Actually, now that I think about, becoming an awesome developer is similar to
the advice for becoming a successful founder. You, counter-intuitively, have
to spend a lot of time doing things that don't scale. A good example is
ignoring all those frameworks and abstractions so that you can really learn
how the code actually works. If you expect tools to do your job for you or
grow reliance upon some temporary artifact you aren't as strong or self-
reliant developer.

In order to be a great executive you have to be a great employee. The military
flavor of this is that you have to learn to follow before you can learn to
lead. You have to know what your people are going through and be willing to
step in and assist your people if the situation calls for it.

At some point a founder has to transition from _founder_ to _executive_ if
their company is to grow or they are to keep their job. Promoting, building,
and marketing a new production or solution is great, but at some point other
people will do that for you. You must be able to lead these people, build
confidence in the team, and provide proper direction. You have to be a leader.

------
alexandercrohde
> • Often don’t get a voice in major decisions – even when you “know the right
> answer”

I'm not sure if the use of quotes here is intended to imply one doesn't
actually know the right answer, but only feels that way. It's a particularly
important point, I feel in my career I've met so many managers insecure in
themselves that they would never consider listening to an idea from a report,
not unless you can convince them it was their own idea.

~~~
shimon
There are a lot of insecure managers who don't want to be challenged on the
merits of their decisions. There are also lots of individual contributors on
teams who are strident in their beliefs even though they might be informed
only from a narrow perspective.

If you're a manager, you can address this by inviting thoughtful debate and
sharing information. But if you're a non-manager employee, you can't always
rely on managers (even when they're good and capable) to have _time_ to deeply
consider your ideas and share relevant info. Therefore, sometimes you have to
accept that major decisions get made without your input.

Ideally you have managers you trust even when they make decisions you don't
understand. In practice, getting that requires a willingness to move and
enough social acumen that you're likely moving into management yourself.

~~~
alexandercrohde
What you're saying is true, you can't rely on your manager to always have time
to listen to what you're saying.

But at the same time that doesn't mean what you're saying isn't something the
manager should have made time to listen to.

Of course it's easy for me to criticize management when a lot of the startups
I've worked at have gone out of business and a lot of the features I've been
asked to build get canceled.

~~~
shimon
True. At the same time, even well managed startups are risky enterprises and
we can't always be sure a feature is right before we ship it. (But we should
try pretty hard.)

------
wolco
Missed the all important contractor. More money, more control over types of
projects taken but little control over actual project.

~~~
ryanSrich
If I had to recommend any path, contractor would be at the bottom of the list.
The stress, constantly shifting from one company to another, not knowing when
you're going to land another client or if your contract will be extended,
having to constantly look for new gigs, etc. Finding a new job is like moving.
It just sucks all around. Being a contractor is like constantly having to find
a new job.

~~~
richardknop
I'd agree in theory. But if you're a good engineer in some tech hub like SF or
London then finding new contracts will be very easy so it might be worth it in
that case.

------
fuddle
This reminds me of the Cash Flow Quadrant by Robert Kiyosaki. A great read:
[https://www.amazon.com/Rich-CASHFLOW-QUADRANT-Robert-
Kiyosak...](https://www.amazon.com/Rich-CASHFLOW-QUADRANT-Robert-Kiyosaki-
ebook/dp/B00BFHV90W) You can either be an Employee, Self-Employed, Business
Owner or Investor.

------
jondubois
I think that the tech industry is unreasonably obsessed with A-list 'brand
name' corporations.

I haven't worked for any A-list brand name companies (no Googles or Facebooks)
but I've worked for quite a few B-list and C-list corporations and also some
B-list startups as a software developer/engineer (including a YC startup) -
The startups which I worked for the longest have grown very fast and are
profitable.

In spite of this, the last time I was looking to switch companies, the only
thing that prospective employers were interested in was my open source work.
Nobody was interested in hearing more about the small startups I worked for
which ended up becoming successful because they're not A-listers.

I know engineers who work for A-list companies (I've worked alongside some of
them in the past), they're very good; but not different from engineers who
work for B-list companies; maybe they're better at taking technical tests.

------
trevyn
There are paths to founder that do not require it to be "incredibly
stressful".

Another pro for founder is that you can remove yourself from echo chambers if
you choose. Maybe this falls under "Choose the people you work with".

~~~
nugget
My experience is that to be a successful founder you have to be "on call"
pretty much 24/7 as you never know when either a major opportunity or a major
crisis will arise. People handle situations and stress differently, so this
may be more of a burden for some than others.

~~~
ghostbrainalpha
This was my experience. I had a relatively successful period as Startup
founder, and was able to put away some retirement money.

Then instead of doing another startup, I took a less stressful job for less
money, and enjoyed my family time.

As a founder I never really had a day off for 5 years. Even if I was "taking a
vacation", my laptop was never always in a backpack within 20 feet from me for
emergencies, and my mind was always focused on the consequences of failure.
For me it was living in fear, even during success.

Some people are more optimistic. They don't feel stress in the same way. I
think that is a KEY ingredient in being a successful founder long term.

------
orthoganol
What about the world of contracting? You can also be someone who has
flexibility on where/ when they work and for who, and it's probably a more
viable 'path' in tech than in any other industry.

Since the vast majority of founders fail, having significant financial
cushions from your family or years working prior is probably the top pre-
requisite if 'founder' is your path.

~~~
Clubber
Contracting is good, but there is a trap. If you find yourself as a contractor
and the market crashes, finding new contracts is much more difficult. At least
I experienced this during the dot bomb / 911 collapse in 2001. Also, you have
to pay for your health insurance, which is getting crazy expensive, and only
gets more expensive as you get older. Make sure you adjust your rate
accordingly.

This may or may not apply to all locations and all collapses, but expect
collapses to happen every 8-10 years.

~~~
dredmorbius
It's possible to switch to _not_ being a contractor.

I'm also not all that certain that down markets don't hit all categories with
similar force. Contractors may be cut slightly earlier (discretionary
spending), but that depends on contracting terms and duration (there are set-
length contracts), and as a bonus might be hired back earlier.

Much depends on whether or not you have a specific skillset that's in demand,
and know how to market it effectively. And that's regardless of your
employment terms.

~~~
Domenic_S
> _It 's possible to switch to not being a contractor._

Sure, but during an economic contraction is typically not a good time!

~~~
dredmorbius
It depends, much of that on your relationship with clients and their own
savvy.

If you're a valued contributor and your client is aware of that, they may be
able to swing things. That may end up being a zero-sum game, with existing
headcount being eliminated. Much depends on the organisation's own policies
and savvy.

It's an argument for maintaining good relations, though.

------
ryandrake
> Often times there are hard barriers preventing people from starting a
> company. In these cases my best advice is to move to a tech hub (preferably
> the Bay Area) and work for a tech company until you can save the money

I had to laugh there. Moving to the Bay Area will _reduce_ your ability to
save money, not increase it. I was probably saving 40-50% of my salary when I
worked in Nowhereville, Florida. With the housing costs out here in the Bay
Area, the long commute (wear and tear on vehicles) and the massive local and
state taxes, it's almost impossible to save.

~~~
mahyarm
80k* %50 = 40k vs. 160k * %35 = 56k

Bay area in a nutshell. You can have higher savings rates too, I do around %40
and I could save even more. Working at a startup does make it harder, usually
it's better to work at FANG. You also learn a lot and realize the difference
between 'facebook does this dev practice because it's huge so it has to vs.
it's the better practice'

~~~
mdorazio
Pre or post-tax, and at what standard of living? Weather aside, you can get
significantly better housing/schools/daycare/whatever for that 80k elsewhere
than you can for 160k in the Bay Area. If you're young and single this is
probably a non-factor, but for people >30 it can be significant.

~~~
mahyarm
Very true on the having kids part. But you typically have 7 years of your life
before you reach 30.

Probably contributes to the logan's run effect you see in SV tech companies ;)

What I've seen from colleagues with kids is the spouse also works some sort of
6 figure job and they either commute a lot or bought a house before it got
extra crazy. Like one who bought a $600-700k TIC around the Haight ~4 years
ago. Or they sacrifice their living standard somehow. The current family set
you see today bought when it was more affordable.

~~~
mdorazio
Good points on how families in the Bay Area are setup today or established
themselves a few years ago. To be fair, though, you have 37 years of
employment after you reach 30... It's kind of scary to think about the Bay
Area being a good place to establish yourself for only 15% of your career.
Logan's Run effect indeed.

~~~
mercutio2
Good developers can make way, way more than 160k total comp without much
effort in the Bay Area. Not at startups, so if you want to earn lots of money,
don’t join a startup.

You have to be good, and work hard, but I know lots and lots and lots of tech
workers who are single earners with kids and a house they didn’t buy before
the boom.

~~~
mahyarm
I agree, but people would of started coming out of the woodwork and giving me
even more exceptions to the rule and how it's unrealistic, so I did the
startup lower bound.

------
losteverything
A good read. What about very stable high paying non-tech jobs in very
techicnal companies? That is the advice i looked for.

Sales/marketing, finance, investor relations, training/ hr, event planning,
etc

For me back 25 years ago, the thought of being in my 40s & 50s learning the
latest version was tiring.

CEOs back then came from finance or marketing.

------
mads
Needs a consultant path. I think once you drank the koolaid too many times,
you just get apathetic.

------
adamzerner
> Executive (Senior Manager at a Large Company)

> A higher likelihood of having a huge impact (given that most startups fail).

I think it's important to note that regarding money, starting a company does
have a very high _expected value_. It's just that it's high risk-high reward,
which makes it a bad fit for people with lower risk tolerances. But if your
goal is to have as big an impact on the world as possible, risk doesn't matter
too much.

[https://80000hours.org/2012/01/salary-or-startup-how-do-
good...](https://80000hours.org/2012/01/salary-or-startup-how-do-gooders-can-
gain-more-from-risky-careers)

------
findoer
Lately I'm getting less emotional about this stuff, and realizing that the
market is probably smarter than me. If skilled businesspeople, politicians,
and people managers are more rewarded by the market, they are probably more
valuable to more of society, or at least the parts with money to give. The
elite probably choose to have their children educated in the humanities rather
than the sciences for a reason. Given that an entry level software development
job will give me enough money to sustain myself indefinitely while saving a
lot, I'm investing in these areas rather than being upset. My logical
reasoning skills (as I can observe them through my performance at chess or
math, two of my hobbies) seem to be improving anyway.

------
DeadReckoning
I am an ambitious employee at a large tech company and I think about this a
lot.

I am living my dream life. I'm 26 and about to break 200k base salary. I have
been programming for fun since I was 13 and I enjoy most of what I do every
day. I feel myself growing both technically and in soft skills. I rarely work
more than 40 hours a week but I still feel very productive. I'm receiving
excellent feedback and am being groomed for engineering management. I walk to
work, the grocery store, and the weed store. I have time outside of work to
focus on self improvement, fitness, and side projects.

But then my acquintance tells me he bought a house in cash after earning XX
million from their startup and I feel I'm completely off track.

------
captainmuon
How about the good old humble entrepreneur? You have a little bit of each
category. In contrast to the founder of a startup, you are not going for
exponential growth or a buy-out, but for a steady income. You'll have both
technical and business tasks, but you can offload some to employees or
contractors, so you can choose where your focus is to some extent.

------
pers0n
You forgot outsourcer/contractor. The company I work for has no one that can
code iOS or Android apps, we outsource everything on Odesk and mark up the
price, of course the quality is crap too. But since we can delete Google
reviews and push down Yelp reviews and disable reviews on Facebook, everything
is fine :/

------
rothbardrand
I've worked for startups for 30+ years. I've seen this industry from before
the dotcom era into the cryptocurrency era (and I work in crypto now.)

Here's my perspective-

\-- Experience is undervalued by people who don't have it. It is critical for
a startup. You don't all have to be experienced, but get someone who has
experience. One of the real killers of startups is bad management, and one of
the causes of bad management is management by instinct, especially terrible is
"type a" CEOs (to pick a stereotype for succinctness sake only) whose
management history was being president of a frat in college, telling software
engineers how to build product, but he knows nothing about software.

\-- Experience as an executive who didn't start out as an individual
contributor is not experience. If you cannot do your subordinates jobs, you
cannot manage them effectively, unless you have a subordinate who _can_ do the
jobs (like a lead) who you manage.

\-- Your CEO needs to be proficient in the unique value of the company. EG: If
you are a sales organization you need to have a CEO who is a proficient sales
person. Apple needed a proficient CEO when it was an engineering / product
organization (and Steve Jobs was that- not as a good an engineer as Woz but he
knew electronics and software development) ... but now Tim Cook is a
proficient supply chain master and that's what Apple needs to thrive now. As a
startup your CEO needs to be able to build the product. Or he will make bad
decisions.

\-- Founders give investors way too much power. They seem to think that
investors are an old boys club that decides who wins and loses. In the valley
for BS startups that's maybe true- you can get BS money until you make it. But
if you're not a Golden Child then you need to get traction and revenue, and
you always, always, want to be in the drivers seat for investment. You never
want to need it.

I've seen so many VC and even lately angel deals with terrible terms that I'm
convinced the reason being a founder is not as remunerative as it should be is
founders signing bad deals desperate to keep the company going.

Always keep your burn rate low.

When I was making minimum wage in college I was ecstatic because I could
afford to go see a movie in the theater every week. That was "luxury" for me.
As my income grew, I kept my definition of "luxury" well below my income. This
produced savings. Those savings helped greatly in lean times.

Run your business that way. You may be able to grow to 100 people now, but
don't, grow to 70 or whatever, so you have more cushion.

If your hiring is ahead of your traction you're probably not hiring the right
people anyway.

------
bogomipz
I am curious if anyone has gone from employee(engineering) and then to founder
and failed and if you were able to seamlessly go back to engineering where you
left off career-wise and pay-wise. Is it a concern?

------
golergka
"Founder" path focuses on start-up. What about small business, as a consulting
shop or a dev shop, that has a very different risk/reward ratio?

------
Philomath
What if you had executives that actually understood the tech behind it? Isn't
that also the point of the CTO being an important role in a company?

------
edw519
_Employee (individual contributor / middle manager) Pro: More work and fewer
meetings_

LOL, IF ONLY!

Another example that people in silicon valley (and yc in particular) have no
idea what goes on in the real world.

(HN reply in one window, with skype and webex open in 2 other windows, my 5th
and 6th meetings today. I've been on HN for 10 years with over 5,000
contributions, almost all while in meetings, ignoring talking heads and
engaging you guys. You don't actually believe I'd be here if I had meaningful
work to do, do you?)

~~~
lkbm
Individual contributors where I work have significantly fewer meetings than
people who choose the leadership route.

What makes my company less real world than yours?

~~~
firebird84
As soon as I indicated I would try exploring the leadership path (I had
originally intended to only progress as an individual contributor, but I'm
bored and I'll learn any skills I can at this point), my managers gave me the
role and immediately I was swamped with meetings. I don't resent it, but I'm
going to see if I can push to streamline the behaviors that lead to this. My
time is now even more precious than ever and I have to find ways to reclaim
it.

------
PeraltaJ
Can't help but this Comma in "Founder, Executive, or Employee " after "
Executive" bugs me...

~~~
nlh
Welcome to the wonder world of the Oxford Comma...a source of debate perhaps
rivaled only by the great Emacs vs Vim wars...

[https://www.grammarly.com/blog/what-is-the-oxford-comma-
and-...](https://www.grammarly.com/blog/what-is-the-oxford-comma-and-why-do-
people-care-so-much-about-it/)

------
jacquesm
You can easily be all three in the course of a single lifetime. It's not a
choice between those three.

------
h4shz
In this life you're either a soldier for someone, a leader for someone, or a
dead man.

------
trhway
the dao of SV - a colleague/peer of mine in employee trenches couple jobs back
become CTO in his next gig and a co-founder of the next gig after that,
already a unicorn just in a few years ...

------
robertocarlos
What would you say maximizes your expected financial returns?

~~~
FLUX-YOU
Safe is being an employee. Risk is the other direction. How much risk you can
tolerate is up to you and how much you have in assets, savings, etc.

------
crb002
And independent consultant. Which I guess is founder?

------
peterwwillis
So why aren't there any tech co-ops?

------
hullsean
what about...

• freelancer • advisor • fractional cto • performance consultant • various
other vendors

------
snow_mac
What about the consultant path?

------
dagss
Consultant.

------
forkstar
Where is the freelance path?

------
metalliqaz
Missing from the strategies for the first two (really all three): come from
wealthy background.

~~~
leeoniya
not really.

my family moved to the states from moscow when i was 7. we spent all our money
that we got from selling a crappy apt on the move itself. we lived on food
stamps, had to learn english, my parents (both with technical university
degrees) went to community college and worked low wage jobs to pay the rent,
bills and tuition. we had a super old used ford that was rusting everywhere a
vehicle can rust and the dollar store was where we went shopping. today, i'm
somewhere between employee and executive [limited only by personal preference
of work/life balance] thanks to my parents; my children will certainly have it
easier than my folks or i ever did. but to say that it was because of some
innate wealth misses the mark.

~~~
didibus
> but to say that it was because of some innate wealth misses the mark

I'm not sure it misses the mark. All data show that wealth carries over
multiple generations. That doesn't mean that non wealthy can't make it, just
that wealthiest will, on average or even probably some p95 and up metric.

And wealth should be put into perspective, its often more to do with the
surrounding education of the wealthy. If your surrounding growing up ran
businesses of their own, knew how to manage people, understood finance,
investments, calculating risks, knew about markets and business, had
connections, that's a great environment to learn the same from. You mentioned
both your parents had technical university degrees, so you had some advantage
there.

Everyone can give it a shot, we have equal opportunity, but not equal
challenges to face. You making it out of less is double awesome to you, even
if maybe you felt it was easy, dunno, its still a hard thing you did, harder
then if you had come from a more supportive environment.

~~~
leeoniya
certainly i'm not saying that prior wealth does not play a major factor or
isn't strongly correlated, but it is not a prerequisite by any stretch, which
was my interpretation of the comment.

~~~
Akujin
I have the same background as you. Crimea, not Moscow.

Americans will never understand. Our parents stood in breadlines. We are
making six figures in America.

It's not about wealth. It's about a culture that respects hard work,
education, and opportunity.

~~~
gbarc888
Same background here. China, not Moscow or Crimea

I worry about the next generation. They say that wealth skips every other
generation, because if a child grows up in a well-to-do family, they will not
value hard work as much.

~~~
dragonwriter
> They say that wealth skips every other generation

Strangely, in all the empirical studies of socioeconomic status and its
relations to family and environment, I've ever seen one detect that effect.

I suspect that the popular saying really just reflects that parents and
children have high contact and lots of friction, and grandparents and
grandchildren less so, and nothing about the reality of wealth or hard work.

------
5706906c06c
As an Executive, I find the other two to be painful to deal with.

------
01096232042
مصطفى عبد الله

------
01096232042
Rayed

------
01096232042
ايمل

------
graycat
For the OP, I see some good news:

Generally there is better advice!

=== Startup Big Point

Here is a big, huge, gigantic point about doing a startup and owning 100% of
it: In broad terms, that's the American way!

Or, it's obvious; just look: All across the US, east to west, north to south,
from an isolated house in the woods to a crossroads up to the largest cities,
sole, solo entrepreneurs start and run successful businesses. No biggie. No
tech. No MBA. No venture funding. No team of co-founders. By the millions --
wrong, by the 10s of millions. If that was so difficult to do, then there
wouldn't be tens of millions of people doing it.

=== US Mainline Business

What do they do?

Mow grass -- the ones on my street show up with $100+ K of capital equipment
counting the truck, the trailer, the mowers, etc.

Note: Now $100 K will pay for one heck of a powerful Web server farm; if you
can keep that farm busy, then just at standard ad rates you have nearly a
license to print money. Or, for computing, $100 K in capital equipment is now
a LOT.

Do auto body repair.

Do other auto repair.

Sell car tires.

Add asphalt to driveways.

Do landscaping, architecture to grass mowing, for good customers, e.g., any
company with nice grounds.

A dentist.

A CPA.

A pizza carryout.

A Chinese food carryout.

An Italian red sauce restaurant.

A manufacturer's representative.

A local wholesale plumbing, electrical, building materials supplier.

A wide range of what can be called _big truck, little truck_ businesses -- buy
stuff delivered in a big truck and sell it out of a little truck.

Run several fast food restaurants, gas stations with convenience stores, etc.

And on and on.

Generally these businesses have one of the most powerful advantages in all of
business -- a strong barrier to entry. That barrier is, and may I have the
envelope, please [drum roll], geographical, that is, the businesses are not in
competition with anyone more than 100 miles away. In particular they are 100%
immune to competition from China. If they are in Tennessee, then they have no
competition with anyone in NYS or CA. Etc. So, if they can do comparatively
well in a radius of 100 miles, then they can do well for their career.

A huge fraction of the people who pay full tuition for their children at
private universities did not take venture capital, did not have co-founders,
didn't get an MBA or a STEM field college degree, were nearly never an
employee, and were not close to any of the scenarios in the OP.

Okay, that, my friends, is American Business 101 Facts of Life. That's the
overwhelmingly popular version of US business and, indeed, US careers. Nothing
else even comes close. And the OP is far away from that.

So, take that US business 101 and, with computing, try to do more -- the
computing should be an advantage.

=== Being an Executive

Okay, briefly, for being an executive: No security. None. Zip, zilch, zero. No
matter what. Instead are an _at will_ employee that at any time can be fired
for any reason or no reason. Biggie reasons for getting fired: (A) As in the
OP, office politics. E.g., there's gossip (you get accused, tried, convicted,
and fired all while knowing nothing about it). (B) The company does poorly.
(C) The company does fairly well but gets bought out by another company. (D)
The owner has a son and wants to give him your job. Etc. The crucial point is,
you don't own the business.

Just as an _executive_ , your skills, alliances, knowledge of your current
job, etc. anywhere else with a dime usually won't cover a 10 cent cup of
coffee.

Is there a way? Okay, be in sales and have a nice list of your accounts that
do well. You don't really want to be the sales manager, just a good sales guy.
If your employer goes out of business, gets bought out, etc., then take your
customer list to whatever company in the industry wants to server your
customer list. Be sure the industry will be solid even if your employer might
not be.

There's just no magic to being an executive. And there's nearly no power;
instead your job is to get along, go along, and hope nothing bad happens. If
you sponsor a new project and it fails, then you have a black mark on your
record, and everyone else has an excuse to gang up to fire you. If the project
is successful, then you have jealous enemies all the way to and including the
BoD.

Part of this is the fact that currently the US economy has about 94 million
people out of the labor force. So, mostly, there's no shortage.

Currently it's too common for Mr. Big CEO to wake up, have a bad day, look at
his budget and organization, draw a big X, and say "Off with their heads." In
this way big, famous companies have suddenly fired dozens, hundreds,
thousands, tens of thousands of people. E.g., at one time, as computing was
roaring ahead, IBM suddenly went from 407,000 employees down to 209,000. They
cleaned out rush hour traffic over big parts of NY, CT, and NJ.

Another time, at IBM Research, a group of about 100 people got into serious
political trouble, and when the dust settled a lot of managers were demoted or
fired and a about half of the rest, about have high-end Ph.D. holders, were
fired. It was all about work-place politics, cliques fighting each other, etc.

Sure, decades ago lots of people could join a company and work until a nice
retirement. Things changed slowly. E.g., could work for Sears for decades and
retire. Sears? It's about to go belly up, totally. No more; that's rarely the
case now. If you really want that, then: (A) Work for a company, e.g., a
public utility, where the employees have a strong union and join the union.
E.g., at one time could do that with the Bell System. Alas, even Ma Bell
didn't last. A local water company might be better. Be careful about a local
electric utility since that industry might change a lot before you get to
retire. (B) Work for government, local, state, or Federal. Remember, though,
even working for government have to be careful about the slot. E.g., don't be
a civilian Civil Service employee for the US military: Then some military
officer is running the place; they likely have their job changed each two
years or so; so a new guy comes in and quickly doesn't like you or your job,
and you are OUT. So, each two years you have to sell yourself to another
person you never met before. That person can make a big mistake firing you,
but, then, you are still fired. So, for a 40 year career, you have to sell
yourself to 20 people you never met before, and you have to be 100% successful
in all 20 attempts. That's not good job security. (C) Work for, say, some very
solid, stable financial institution, maybe The Ford Foundation.

Officer in the US military? Every now and then you are up for promotion, and
if you get passed over three times or some such, then you are out. So, as time
goes on, the many lower level officers become many fewer upper level officers.
It's not at all clear which lower level officers will leave; it is totally
clear that nearly all of them will.

Net, it's better to be a non-commissioned officer, e.g., a sergeant where you
can keep your job. Even if you get 4 stars, like General Mattis, you can be
out because someone up there didn't like you.

Some private companies have personnel policies similar to the military for
their officers: They hire lots of people in their 20s, and by age 35 they are
in management or out the door. It's not at all clear who will be out the door,
but it's totally clear that nearly all of them will be. A lot of those people
would be better off in their 20s starting and growing a grass mowing service,
quite literally: There's a good geographical barrier to entry, and the grass
will keep growing. Commonly in the US, a Ph.D. in electronic engineering will
have a better long term career as a licensed electrician. No joke.

I know a guy, bright enough, who got a Master's in environmental engineering.
His real career was as a plumber and installer of home heating systems.

=== Being a Founder

What the OP says about being a founder is quite narrow.

I have a high school friend. His father was selling beer for a small brewery.
The brewery went out of business, but he knew a lot of people in the beer
business. He went to the NW corner of his state, arranged to distribute about
six brands of beer (right, the beer came to his warehouse on a railroad siding
via railroad freight car) and sold out of little trucks. Somehow people still
like beer! He passed the business down to his son. People still like beer!
Good business. Darned good business.

If want to go into computing, then be sure you have an even better business
than selling beer.

The OP wants to say that the business idea in computing is not very important.
IMHO, that's mostly nonsense.

Sure, if want only routine technology, then the OP comments about employees,
teams, etc. are important. But a business with only routine technology tends
to have a darned small barrier to entry. Sure, one of the best barriers to
entry was virality from a social network with a strong network effect, but
that's path seems to be about saturated.

Again, there are 94 million people out of the labor force. So, if you want a
job as founder of a successful business, then, IMHO, need to do something new
and powerful with a good barrier to entry. Basically you have to plow new
ground in US business, have to do something those 94 million don't know how to
do.

------
gaius
_Producing results isn’t necessarily how you move up the corporate ladder.
Internal politics are usually as important, if not more so_

For those kinds of people, that should be listed as a pro rather than a con. A
job you can do purely by schmoozing and not producing is exactly what they
want!

------
mattdawson
The lack of even a nod to diversity issues (race, gender, class, etc.) that
the tech industry is dealing (or not dealing with) is tone deaf and insulting
to the extreme.

~~~
powera
This insistence that everything always has to be about diversity is both
insulting and counter-productive. Maybe some of the time we can talk about
things that work for all people?

~~~
greglindahl
That's exactly what diversity is about -- taking the status quo and changing
it to something that works for all people.

