
Ask HN: Regreting Not Doing a Startup - hfar
Hey, to anyone late in their career who wanted to start a business but didn’t do it, do you regret it? Why?
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rafiki6
I did one for about 6 months. It flamed out hard. My co founders and I parted
ways. We had no idea what we were doing and it showed. Had we persisted we
might have succeeded, but honestly who knows or cares. You have to ask
yourself what it is you actually want from starting a business.

Is it to become a wealthy and famous billionaire? Don't bother unless you have
all the pieces stacked in your favor.

Is it to do something you're passionate about? Find a way to do that anyway,
whether it's through working with friends on it, working for someone on it, or
working by yourself on it. You can still do that with a day job, just try to
limit all the other things in your life that might distract you.

Is it to be your own boss? You're not gonna ever be your own boss. Your boss
is the person who pays you the money. You can only be your own boss by
achieving financial independence which you can do with similar amounts of risk
in other ways.

Is it because you hate your job or chosen career? Entrepreneurship amplifies,
not limits, the effects of that.

Most successful businesses are started by people in their mid careers who have
developed a solid network and good set of skills as well as a decent financial
cushion and sent their kids of to be independent of them financially.

------
kokanee
I very nearly did a startup with a friend. We had a bit of seed money and were
accepted into an accelerator, and had a decent beta. But we had major concerns
about the market, which seemed to be a bit of a fad, so we pulled out at the
last minute. I don't regret that decision at all - within a couple years the
primary competitors failed and Amazon ate their lunch.

What I do regret is never finishing my side projects. I recently stumbled
across a little website that my boss had paid me $50 to make for his cousin
years ago. It was a slick but very simple site that basically just played a
few useful audio files. The site now accepts donations and has been wrapped
into paid iOS and Android apps that have thousands of downloads. It kills me
that someone has made thousands of dollars off of that dead-simple weekend
project. Over the last 10 years there has virtually never been a time when I
wasn't working on a side project, and yet I haven't actually launched and
monetized a single one.

~~~
jjoonathan
I have a similar story. I let myself steer pretty far in the startup direction
before I ultimately dropped those plans.

7 years later, I'm on a M&A team evaluating startups in the exact space I
would have been in. There are many of them and few of us (companies looking to
acquire). Most of them have failed or will fail and get nothing (beyond
investment). The winner will get a mediocre payout that, for the founder, will
merely compare to the salary I've earned in the meantime, if my back-of-the-
envelope is correct. The stress, of course, will not compare. That's the
reward for the _winner_.

I don't envy the people across the table.

------
thrownaway954
i regret working myself into early alcoholism and it costing me my marriage.

i look back on life now and realize that me being a workaholic wasn't
necessary. i was making damn good money with the career i had, but always
needed MORE. wish the old me could tell the young me that you're rich enough
and if you really want to make an impact on this world, be one of the few in
your generation to celebrate a 50 year wedding anniversary.

my friend... if you're married, go home and kiss that spouse of yours.

~~~
YorkianTones
love this, thank you for sharing the advice

~~~
hfar
Yeah, good advice. Always hard to balance career vs personal life success.

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im_down_w_otp
I'm not the archetype you were asking for, but I am later-ish in my career (40
years old). I co-created a startup not all that long ago (little over a year).
I don't regret creating a startup, _but_ it is very very hard at times in ways
I did not anticipate. So, there are times when I'm very envious of my former
self. Where I got to deal with the perils of regular employment rather than
the perils of being an employer. Thoughts like, "Ah, I remember the good old
days when this kind of thing was somebody else's problem to deal with. Those
were good times. Good times. Welp... (rolls up sleeves to try to figure out
the least bad decision from a mountain of uncertainty)"

That's despite having previously operated a moderately successful small
business and also helping lots of other companies take on difficult technical
challenges and get their products to market. So, there are a lot of things
that I had my eyes wide open to that sometimes less experienced founders I
know end up a bit blindsided by.

I can't speak for anyone else, but I can say for myself that if my motivation
for undertaking this were rooted primarily in the possibility of regretting
not having done it, said FOMO would probably not provide the sustaining
fortitude necessary to keep pushing and pushing and pushing through the
numerous challenges in fundraising, development, go-to-market execution, etc.
etc.

So, my only real bit of commentary would be to do a startup because you're
dead certain that's the thing you want/need/should do to achieve some goal
about something you want to change about the world, the marketplace, and/or
the state of technology, etc. I'd not suggest doing it on the fear of regret
of not doing it. If that makes any sense? That said, if you have a goal or
ambition like that, then I'm always supportive of folks who want to go out
there and grab ahold of entrepreneurship and ride it either into the dirt or
into the sunset.

~~~
mikekij
>I'd not suggest doing it on the fear of regret of not doing it

Second this. Don't start a company because you think it's "checking a box". It
has to be something you can't imagine not doing, or else you're in for a world
of hurt.

~~~
bdcravens
Also, unless you're going to be a one-person operation, it's a very serious
responsibility. People will be affected by your hiring and firing decisions
(and not just your employees, but those in their circle).

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mikekij
I'm the opposite of the person you're asking for, but I'll take a stab. I have
the academic pedigree to have worked in a lucrative scientific / banking /
management field, but instead chose to take an entrepreneurial path. I could
likely have made more money (risk adjusted) on the other path, but am thankful
on a DAILY BASIS that I'm a pirate, and didn't join the navy.

Had I not chosen the entrepreneurial path, I'm confident I'd be the person
you're asking for: late in my career and regretting not starting a business.

~~~
tluyben2
Same here exactly!

------
xapata
Nope. I refuse to regret my past choices, so that I can be happy with my
situation. If you gambled and won, it might have been a bad bet. If you
gambled and lost, it still might have been a good bet. No sense in regrets.
Best of all possible worlds, and all that.

~~~
JangoSteve
This is so true. I've started a few startups and had a good acquisition. I've
since made it one of my missions to espouse the underappreciated role that
luck plays in a successful startup, and in life, in general.

You don't often hear it from people who have had the kind of success that
leads them to being keynote speakers, I think, because everyone wants to feel
like they deserve the success they've gotten. So, survivorship bias tends to
kill this message. I think it's important, though, for people to understand
when evaluating decisions (past, present, and future) and for learning from
and empathizing with others.

Everyone likes to think of life as a meritocracy; that when you succeed it's
because of the decisions you made and actions you executed. But people can
make the right decisions for the wrong reasons, or vice versa. People can be
prevented from making the decisions they'd like through no control of their
own. And perhaps most significantly to the point, two different people can
make the same decisions with different outcomes.

------
martythemaniak
Before you regret something you didn't do, ask yourself whether you understand
that thing well enough to regret it. Why did you want to do a startup?

For example, one popular reason is "I'm my own boss", but that's largely
wrong. If you're trying to make money, you have bosses. Going from a salaried
job means going from one or a few bosses to many, many bosses. Depending on
the startup, these could be a multitude of consumers, a few big clients and/or
investors. These bosses will not tell you directly what to do, but will rather
stop paying you, or never pay to begin with if you don't do what they want out
of you.

You needs and wants about what you _want_ to do is probably very different
from what your bosses will pay you to do, and adjusting your needs/wants/ideas
to what will pay is what we call "finding product-market fit". Yes, new
markets arise, and sometimes someone extraordinary will mold the market to
themselves, but largely you'll be molding yourself to the market.

This is not to say being your own boss is BS - you still get plenty of
autonomy and are the final decision maker. The layers between you and the
market are extremely thin, so the highs are higher and the lows are lower.

~~~
wpietri
One point I love about having many bosses is that the more numerous they are,
the more you can get away with ignoring any single one. When I was consulting,
I always tried to keep a few gigs going at different levels. That way if one
client wanted something insane or dangerous, I could say, "Gosh, so busy!" and
move along.

Paradoxically, having the ability to say no meant I didn't have to say it very
much. When a client wanted something foolish, I could say confidently, "I
don't think that's in your best interests," and explain why without fear.

------
AnotherGoodName
I recommend side gigs. I co-founded a reasonably successful business (5
employees) from a side-gig (i was supporting getting remote sensor data
remotely from a modem into a form easily red by clients).

Side gigs are reasonably risk free and will grow or shrink organically. You're
not trying to force a market. The question is do you know something that works
as a side gig? If so go for it.

Remember that the big idea->millions in venture funding->unicorn or bust path
isn't the only way to go. That's a very stressful path.

------
xwdv
No. You can start a startup at any time.

What people mean when they regret not doing a startup they mean they typically
regret not trying to start one when young, having it become a booming success
and then reap the rewards for a larger portion of their lives.

There are better regrets to avoid in life; the regret of a lost love, the
regret of not reconciling with your parents, the regret of not having a child,
or the regret of not tending to ones health.

------
coffeemaniac
I'm not exactly late in my career but having been doing this for ~7 years I'm
not clear how people are able to accumulate the capital to start a business
and have enough cash to live on until it makes money. It's something that
seems like a great experience, and I can see myself wishing I had been able
to, but I just don't know how I'd afford it.

Even assuming you have virtually no business expenses other than cloud
hosting, are you just supposed to watch your emergency fund disappear?

~~~
Dave_TRS
The solution for me was buying cheap houses in Detroit. For $30K you can buy a
house that nets you $500 a month ($800/month rent minus expenses) so for
example if you save $150K from your job that buys 5 houses yielding $2500 a
month (or if you had $300K savings, $5K a month). That was the way I was able
to replace at least part of my income and venture off to the land of not
having a salary to free up time to pursue other projects.

~~~
paganel
That's a 20% yield if I'm not mistaken, there's got to be some catch to it.

Are those people renting a $30,000 house with $800 per month able to get
banking services (and mortgages)? If not, I would feel like a dickensian
landlord renting those houses to them.

~~~
deleuze
Even at a 10% interest rate and 0% down, a $30k mortgage is only $263/mo. This
person is basically admitting that they are extracting value off the backs of
the working poor due to unequal access to the banking system. I cannot imagine
admitting being a slumlord on a public forum. And people wonder why people
hate landlords.

~~~
poulsbohemian
If he got a loan, it wouldn't be 0% down because it would be on investment
terms not residential terms. Chances are a $30K house needed improvement
before it could be rented, and rentals are seldom free to run either --
there's ongoing maintenance, there's the carrying costs between tenants, etc.
Calling the parent poster a slumlord without facts when your account is just a
few hours old is pretty lame.

------
ruffrey
I worked with a man who had done boring and lucrative government contracting,
startups, tech companies, and self employment over a 35 year career. His last
“job” is a startup. You always have choices. Especially if your skills are up
to date.

------
wpietri
I have started a few things with varying levels of success. I was looking at
starting another thing, but instead decided to take a job with a not-for-
profit. I don't regret the choice, because as a general rule I believe it's
never too late to start something. I'll never stop having ideas, and given
that we've had 250 years of technological and economic innovation, I think
there will always be opportunities.

What I would regret is walking past a specific confluence of circumstances
that seemed especially auspicious. It's sort of the inverse of my top reasons
startups fail: [https://www.quora.com/Startups/What-are-the-early-
symptoms-t...](https://www.quora.com/Startups/What-are-the-early-symptoms-
that-a-startup-is-going-to-fail/?share=1)

If this time I had found people I really wanted to work with, an idea that had
promise, a market that we loved, etc, then I would be kicking myself for
walking past that. At the end of the day, I ended up taking the path where I
thought my next few years would have the most impact on the things I care
about. I made the best decision I could with the facts I had. We'll see!

------
PopeDotNinja
I started a business. Sold it for a couple years salary. Glad I did it. Don’t
miss it.

~~~
vasergen
could you share the details, which type of business

~~~
PopeDotNinja
It was a recruiting business. You can read the short version on my LinkedIn
page. Link in profile.

------
poulsbohemian
My first internships were early-stage / startup type businesses, and the last
decade+ of my tech career were at similar companies or businesses of my own.
They gave me a wider array of experiences and a greater sense of personal
control, but there's no doubt I would have made a lot more money elsewhere.

I wish in the early part of my career I would have not been so eager to get
into startup / entrepreneurship land and had instead tried to get a few more
"name brands" on my resume, for the experiences and contacts. That would have
helped down the road.

I would actually spin this question back around on you: Now that you are in a
later stage of your career, what's stopping you from starting something now?
Don't ask if you will regret not doing it, figure out your plan and do it.

------
remote_phone
Honestly, don’t regret not starting a business. It’s about 1000 times harder
than you think it is, despite all the glamor and wealth that 1% of the people
achieve. Doing a startup takes a certain personality type. I am not that
personality type. I joined a startup and saw the type of madness that was
occurring and that made me understand how ill suited I was to start my own
company.

My guess is that if you didn’t already start one at this point, you probably
don’t have the proper personality type in the first place. Founders don’t need
the opportunity, then just go for it, and it’s that type of spirit that keeps
them going through all the ups and downs.

~~~
rafiki6
Doing a startup takes luck. So much luck. Luck of birth, luck of everything
going right, luck of meeting co founders, luck of circumstances being right to
allow you to take risk. It's mostly just luck.

------
danpozmanter
It isn't a binary question of "startup or not" \- but always comes down to the
specifics of what problem you wanted to solve, how you wanted to solve it, and
all of the logistics (especially timing and team composition).

------
ykevinator
I am 50, my advice is don't fall into the trap that its either or. You can get
a lot of signal without quitting your job. You can get a lot of work done by a
$15/hour stay at home mom remotely. You don't have to risk it all. Once you
are making money you can make the jump, or abort if it's not working. Just
make sure your spouse is on board so there are no fights. If she is not (no
sexism intended, I assume you are a man because women don't typically ask
questions like this) then dont lose your marriage over it. That is a very real
thing.

------
dred_prte_rbrts
I think about this most days. The problem is that startups that fail put you
very far behind relative to peers and the majority of startups fail.

It's fun, but it's also gambling with your financial future.

~~~
michaelmior
> startups that fail put you very far behind relative to peers

I think this really depends on what metric you're using for success. If it's
finances, a failed startup is almost certainly a significant setback. In terms
of experience, that's much more debatable.

~~~
xwdv
Believe me, finances is the metric of success for 95% of people and for the 5%
where it isn’t they are either independently wealthy already or so delusional
that failure is guaranteed.

~~~
convolvatron
if no one did anything because they loved it, or because they thought it would
help humankind, the world would be a much sadder and more transactional place.
i dont know that we would have mathematicians, musicians, writers, costumers,
chefs...or really much of anything

maybe just replace delusional with 'idealistic' or some other dismissive but
less directly offensive term

~~~
bradlys
Or maybe it's that many people who did those things and became successful with
it are from privileged positions that allowed them to do such things...

And so if we lifted people into positions where they didn't feel like their
basic needs would be taken away if they didn't work some job making money then
they could experiment and do things that were less transactional... But until
we have that Star Trek future - we gonna be transactional.

~~~
convolvatron
i guess i was talking sideways...was trying to say that some of the most
valuable things we do as a species are already non or quasi transactional.

------
binarysolo
Have data on the opposite end: super stable type (Stanford MS&E undergrad; PhD
track in ML 10+ years ago) who chose startups and entrepreneurship in scrappy,
un-sexy niches of retail excess, operations research in shipping, etc.,
passing up opportunities in ibanking, hedge fund, and ML in Big Tech in the
past ~15 years. My East Asian extended family was INCREDIBLY FRUSTRATED that I
kept going off the beaten path and not following the "cultural formula" of
good school->good role in company->seniority through years of service for a
tried-and-true path forward... and they were right.

The EV of every path I've skipped was probably low eight figures by age 40 and
more comfort/sanity, based on my friends/peers who went into them. Instead I
have a semistable lifestyle business that I obsess over 24/7 and am constantly
doing things outside my comfort zone, and while I make a reasonable amount
there's a lot of business and inventory risk loaded in every step.

If I had a recommendation it would be this: instead of FOMO, collect a data
point or two -- especially since you're implying that you're more steady-eddy
and mature in your career path, switching to do a business for 2-3 years is
super respectable and has very little downside since I imagine you have plenty
of network and history to fall back to. Several of my friends in their 30s-40s
have expressed a romanticized view of my career path to me, to which I bluntly
say: this is mostly shit work that I suffer through to be consistent with
identity and my values. It's got higher highs and WAY lower lows than your
traditional 9-5, and I wouldn't wish this upon my enemies or friends. Do it
only because you see unfilled needs and it bothers you so deeply that you
gotta fix it on the market yourself.

There's a deep amount of glorification of entrepreneurship that's
celebrated... and while I think everyone loves to see the journey, I honestly
don't think most people would care for it themselves. To use an analogy: it's
exhilarating to see an olympic gymnastic do her thing and push the limits of
human possibility in 3-5 minutes on TV... but honestly, do most kids wanna
practice 4-8 hours daily in a gym during your formative years of 8-18,
obsessing over form and weight transfers and live with constant soreness and
bodyaches while most people their age get to play videogames and gossip with
friends and develop life their own way? Starting a business can have tradeoffs
that feel similar -- for the brief moments of glory that are celebrated
there's a lot of discomfort, monotony, suffering, and uncertainty that
accompanies it that is rarely portrayed.

But simmer in that angst and FOMO... just realize you can use that as energy
to get you to start down the path. Get a good advisor who's done it MULTIPLE
TIMES BEFORE and hash out an MVP, and get the experience yourself before you
figure out whether you want more. You're in a good position of having
developed a long track record, so leverage your strengths and come collect a
data point. :)

~~~
hfar
Very thoughtful reply, thank you :)

~~~
binarysolo
Good luck on your decision -- it's a toughie! :)

