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Entrepreneurs who regret starting businesses

170 points by pmoriarty 4y ago

biren34 4y ago
I say that the need to start your own thing is a bug not feature. It IS a hard life, with tons of risk, change, and uncertainty. My wife hates the instability of it all. I've missed or worked through many vacations, concerts, and other things over the years. It's not even clear that it's a good deal, when you factor in opportunity costs, hours worked, and chances of success. So, it if you don't have to do it, don't do it. You're not going to succeed unless you are just the kind of person who can't be happy going down another path. It all sounds harsh, but it's actually a lot better than the risk/reward offered in many other fields: acting, writing, sports, etc. This is just how professions with tournament-style payouts work, and you either buy in or you don't. Know thyself...it never pretended to be anything else.
gumballindie 4y ago
“But as evidenced by the collapse of Silicon Valley Bank in March, which left many small firms without access to their essential accounts” Yeah as if that happens every day. This sob story was clearly written by someone who has no clue what running a business means.
known 4y ago
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ttcbj 4y ago
This article is super generic. It could have been written about any career path -- Some people who dedicate their careers to ascending in a single corporation regret it, Some people who aspire to be corporate lawyers regret it, Some people who become ski instructors to have more time to ski regret it. Careers are long, and I think the key is to try things, learn what suits you, and generally try to evolve towards things that are a better fit for you.
game_the0ry 4y ago
One thing that I did not see discussed in the article but I think should be contemplated - when your business goes bust years down the road, it is not easy to go back into the job market. My dad had successful business he started in his 40s, but it failed in his mid 50s. He was engineer before, so it wasn't like he could just go back in the job market. Those were very difficult years.
SlickStef11 4y ago
“Whether you think you can, or you think you can't--you're right.” https://matt-rickard.com/reasons-to-do-a-startup https://matt-rickard.com/reasons-to-do-a-startup
bobleeswagger 4y ago
Regret is a natural part of any long term choice.
idopmstuff 4y ago
I started and run an e-commerce company, and my best advice before starting a business is to think very little about what you want your product to be and a whole lot about what you want your lifestyle to be. Want to have relaxing end-of-year holidays? Don't start a B2B SaaS company in which you're going to close a huge % of your yearly revenue in the last few days of the year. Want to be able to travel? You're probably better off with an internet business than a brick-and-mortar store. Want to be able to eventually step back? You need to make sure that there's a path to lessening your involvement over time without hurting the business. I started mine during the pandemic and got it to profitability. It's not world-shifting money, but it produces solid cashflow. At that point, rather than trying to raise money and aggressively scale, I automated as much as I could. Got a manufacturer to make the products. Found a 3PL to handle fulfillment. Went through all the common types of support emails I got and made sure those questions were addressed proactively in the product or emails, so I get basically no support emails. Handed off bookkeeping to a professional. Some of that has changed (the 3PL was terrible and for now I'm doing some fulfillment myself and using Amazon for the rest), but overall I'm only spending a few hours a week on the business. I write marketing emails, ship some product and place orders for stuff as needed. The really nice thing is that I can move things on or off of my own plate as my workload changes. I'm working a full time PM job that I'm loving, and my wife just had a baby, so I might offload the marketing emails soon (but honestly they're super quick and I often just reuse last year's, so that's tough to justify). If I leave my job, I could definitely move manufacturing in house to expand margins. I think more than anything, it's those qualities of the business that make it great for me (definitely more than the product).
- james-revisoai 4y ago
  > The really nice thing is that I can move things on or off of my own plate as my workload changes. This is the goal! > Want to have relaxing end-of-year holidays? Don't start a B2B SaaS company in which you're going to close a huge % of your yearly revenue in the last few days of the year. Can you tell me more about where this point comes from please? I'm not sure if it's a US-UK cultural difference, but if ever, business tends to close around the financial year ends here (early April), not christmas. If you haven't got something signed in November, it usually doesn't happen till January and UK workers take quite long christmas breaks. Or have I not experienced what you are talking about it?
janetacarr 4y ago
I think what people don't seem to understand is that entrepreneurship is a skillset. You can get better at it by practicing. Like any skillset, you can build a career out of it. And, just like any career, you could end up on the scale of loving it to hating it. I'll admit it's quite a bit harder than any other career though since often you can't look to your peers for advice or examples of success. It's largely a game of taking on risk to provide value to people who will pay for it. If you've never promoted yourself online, how do you expect to learn enough marketing chops to get people to the value you provide with your business; how do you expect to learn enough sales chops if you've never sold anything to anyone before. As for me, I'm just a lowly independent consultant, so make of this what you will, but I understand that I'm slowly getting better at sales and marketing, and understanding the value I can provide to my clients, and what makes my consulting different (and hopefully better) than others. Like a natural career progression, I hope to give myself a promotion by creating and selling digital products one day using the skills I've built at the bottom of the ladder.
nkotov 4y ago
I'm in year five of building companies, three years doing it full-time. I don't have regrets but there have been extreme low point - primarily tied to other people. Firing others. Having investors pull out last second and forcing us to shutdown. Having cofounders quit, or worse, intentional sabotage the team. It takes a certain type of person to want to continue doing this long-term. Most people don't have that. One thing I wish someone told me early was that being consistent is the key. I spent the first ten years of my tech career looking for hacks to just realize the best hack is to just doing things consistently and speak to new people all the time. Once you have your pace set, just running with it and sticking with it results in things to start happening.
theery 4y ago
It definitely looks easier than it is. You have to want it.
rco8786 4y ago
I am 100% certain that many entrepreneurs regret their choices. But kicking off this article highlighting a person whose stated alternative to entrepreneurship was "consistent 7-figures at a management consulting firm" is laughable, as though that's an option for most people.
- avidphantasm 4y ago
  Yeah, my reaction to that quote was, “well at least probably did less damage to society as an entrepreneur.”
  - koromak 4y ago
    Exactly
- akrymski 4y ago
  I'm pretty sure that the probability of hitting 7-figures in a consulting firm is smaller than hitting that figure as a founder of a startup.
  - pg938hkd 4y ago
    Yeah but hitting 300-500k is still quite comfortable
- rwmj 4y ago
  Plus if he was a management consultant I bet he'd hate it even more.
- deleted 4y ago
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- jrochkind1 4y ago
  I honestly stopped reading right there in paragraph 3 or whatever, it made me too mad. But i still came here for the comments!
osigurdson 4y ago
The YCombinator model seems pretty good. Try something bold when you are young, if it doesn't work out - whatev. The 1%-2% that go on to become successful are able to fund the whole system.
bicijay 4y ago
Great first article to see in the morning, while trying to bootstrap a startup! Today is gonna be a good day.
- HeyLaughingBoy 4y ago
  And you didn't even need to use your AK.
onion2k 4y ago
One of the things I learned running my first startup was that I really don't enjoy running a business. The mountains of admin work, the never-ending decision making, the constant anxiety of whether or not I made the right call, the pressure to never actually switch off and just work work work, all of the pointless 'networking' with people who're pretending to be interested ... it all adds up to a pretty horrible experience. The high points (raising a successful round, first revenue, first hires, etc) kind of make it worthwhile, and obviously an exit is nice (not that I'd know... I've never got to that point), but I don't think I'd do it again unless I have an amazing idea that I have to build. Anyone who tells you being a C-level person in a startup is fun and glamorous isn't running a real startup.
- rsrsrs86 4y ago
  I always ask candidates why they want to work at an early stage startup as a developer, and “because it must be fun” is a show stopper. Being a founder is certainly not fun. The good parts are there, like earning money, interacting with your team and seeing them grow, the first round, the first sale. But the job is quite painful itself. Please note that not all startups and founders are / want to be funded with billions of dollars. The true story is that you are going to be overworked and fail 99% of times.
  - s1artibartfast 4y ago
    Maybe fun isn't the right word, but the best startup engineers that I've met found great satisfaction in their work. They enjoyed the engineering, the subject matter, and the process of learning. It is closer to the type of "hard fun" one has training and running a marathon, than the "easy fun" of watching a movie or playing a game.
    - rsrsrs86 4y ago
      Yes, it's hard fun :)
  - amanj41 4y ago
    Similar to the sibling commenter, I would say it's a matter of semantics. I am one of three developers at a small startup and definitely would describe the experience as fun albeit stressful. The two sentiments are not mutually exclusive. If it's not fun / interesting / challenging, the possibility of options being worth something in future would absolutely not justify the stress of working at a startup
donutdan4114 4y ago
I don’t know that I fully regret starting a business but boy does it suck like 90% of the time. I’m fortunate in that the business does really well, but…. I just can’t stand it anymore. The stress, the boring, the frustrating, the getting taken advantage of, the weekend hours…. I suppose I fell a little bit into the trap of someone wanting to open a cafe because they like being at a cafe… well I like programming, I like solving problems… but running a business (and a successful one at that) is tough. I can see why most CEOs are non-technical, because it’s a special type of sadistic person who would ask for this. I’ve tried steering the ship towards some goal or task that would maybe make things better but there’s no point. The business is on autopilot. The business is like it’s own person with its own wants, needs, desires… and they come first. They always come first. Bending over backwards to keep something running, get some bug fixed, satisfying some customer, putting out fires… takes higher priority than friends, family, personal time, etc… It has to. I can’t let the business suffer. People depend on its success, most of all my family. I can understand why the rich suffer so.
- enumjorge 4y ago
  > the getting taken advantage of I’ve been thinking of starting my own business and I hadn’t heard of this before. It sounds draining. If you’re comfortable, would you mind sharing an example of how people try to take advantage of you?
FlyingSnake 4y ago
Entrepreneurship is like one of those carnival games where you throw darts or something. Middle class kids can afford one throw. Most miss. A few hit the target and get a small prize. A very few hit the center bullseye and get a bigger prize. Rags to riches! The American Dream lives on. Rich kids can afford many throws. If they want to, they can try over and over and over again until they hit something and feel good about themselves. Some keep going until they hit the center bullseye, then they give speeches or write blog posts about "meritocracy" and the salutary effects of hard work. Poor kids aren't visiting the carnival. They're the ones working it. -- Original comment from notacoward here: https://news.ycombinator.com/item?id=15659076 https://news.ycombinator.com/item?id=15659076
- deleted 4y ago
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- nightski 4y ago
  The world will never be fair, I'm not even sure that is an ideal goal. The best things in my life have come from when I faced adversity, not when I was in a position of privilege. While opportunities are not always equal in quality or number, there are opportunities if you seek them. It's ironic that even though lots of things come down to luck, it's very possible to put oneself in a position that makes it feel like they are very lucky! "Luck" tends to follow those with initiative.
  - coldtea 4y ago
    If fairness is not an "ideal goal" what is? >The best things in my life have come from when I faced adversity, not when I was in a position of privilege Does that hold for kids hungry and unable to finish school because their parents don't make enough then? (Or much worse situations)?
    - detourdog 4y ago
throwaway8456 4y ago
I started, boostrapped and sold a SaaS business. By most standards, this was a resounding success. I won't have to work again ever if I don't want to. This being my first company, I was obsessed with it. Towards the end, I burnt myself out, I had neglected my wife and kids for years, and I was just so miserable. I used to love programming, but I could not concentrate anymore. I started developing resentment against the entitlement of the software engineers I would hire. My heart was broken every time I would read articles/comments on HN about how working for a start up is a scam that only benefits the founders. It was time to get out. I was lucky that I sold in 2021, when the multiples were higher than ever. But I have lost my marriage along the way, and I have definitely lost a few years of life expectancy. I really wonder if it was really all worth it. I know at the end of the day though I had to go through that. I had to see it with my own eyes. In the end, things worked out for me. I can't even fathom how I would feel if the whole thing had failed. I really came to the conclusion that most of the time, starting a company is for suckers.
- throaway33355 4y ago
  From throwaway to throwaway: Would you mind sharing some contact details, or reaching out to throaway33355@proton.me? Am in similar situation and would love to have a chance to reflect with someone who's been through it.
- inconceivable 4y ago
  i also sold in 2021 when the money flowed easy. i'm not set for life but i could easily go 10 years, longer if i sold assets. eventually the burnout faded, my health improved (knock on wood) and the boredom got to me after 1.5 years and i'm working again. working on personal projects "for fun" is not the same as making money, no matter what anyone says. buying expensive shit is awesome for a while but it gets old. especially if you already have a home you actually like living in and the 'expensive toys and experiences' itch has been scratched for a while because your business was already successful by the time you sold it. i don't want a huge house and i don't need another car or overpriced workstation computer. it makes me wonder what drives billionaires to keep going. they're probably just bored when they're not working. it really might be as simple as that.
rozenmd 4y ago
I wanted to document a regular person's experience building a business while working full time, it wasn't until the end of my third year before I made my first dollar from a stranger on the internet: year 1: https://maxrozen.com/2018-review-starting-an-internet-business https://maxrozen.com/2018-review-starting-an-internet-busine... year 2: https://maxrozen.com/2019-further-reflections-trying-to-start-an-internet-business https://maxrozen.com/2019-further-reflections-trying-to-star... year 3: https://maxrozen.com/indiehacking-3-year-review https://maxrozen.com/indiehacking-3-year-review year 4: https://maxrozen.com/2021-strangers-paid-my-macbook https://maxrozen.com/2021-strangers-paid-my-macbook year 5: https://maxrozen.com/2022-just-keep-shipping https://maxrozen.com/2022-just-keep-shipping In the end, my business has been described as an "internet laundromat", it's definitely not a unique idea, it was a pain in the ass to get here, but I don't regret it.
- mportela 4y ago
  Great story and write ups. Thanks for sharing it!
gizmo 4y ago
> The start-ups he later launched all ultimately failed. And even now, as a solopreneur, combining freelance consultancy with writing books and developing information-based products, he often looks back with regret at not simply sticking with his job at a large management consultancy in Beirut. He now has a consultancy called "Business Model Hackers LLC". One of his books is titled: "Vision, Mission, Values, Aspirations, Do They Matter?: A Business Professionals’ Guide to Drafting Vision/Mission Statements and Their Purpose in Modern Organizations". I wrote a couple of paragraphs and deleted them, because really, there is nothing left to say.
- rchaud 4y ago
  Lots of ex-management consultants do this in their 50s, writing books and getting on the paid speaking gig circuit. Any business will have significant marketing and admin work that's challenging to manage. That's true whether you're shilling a book or running a SaaS company renting Shopify plugins to dropshippers.
shubhamjain 4y ago
Both the examples in the article are agency/consulting businesses. There's a reason for that. Such businesses offer no respite of any kind, especially so if you've decided to scale. You're constantly on the hook to find new clients, and to meet the demand, hire more employees, and then, find even more clients because the hires aren't getting utilized enough. And let's not forget about downturns. Even a small dip is enough to left you scrambling to pay your employees. In most cases, the revenue multiple tends to be much on the lower side in the case of a sale. So, don't except a big pay day. I am not saying, product business is easy either. But, consulting business is relatively easier to start and lures you into thinking that it will also be easy to scale, which is an easy trap to fall into. With entrepreneurship, the kind of ship you're driving matters. I don't think there's much to regret when you're running a profitable software business with 80% gross margins and <10 employees. In today's economy, it's not an impossible dream.
davidn20 4y ago
My guess is running a startup is like running a marathon. The idea of it is great to many people, but as people start to train they realize all the work it takes and drop out. People get into things without fully understanding it all the time. The few that really love it or enjoy the process makes it to the starting line.
- simonswords82 4y ago
  Totally agree. The number one rule of (most) startups is that everything takes infinitely longer than you would imagine. And then, even longer than that still...
- slavoingilizov 4y ago
  Understanding everything before you get into it is overrated. Belief is a necessary requirement to move the world forward. And that in itself requires some naivety. Otherwise those people who can actually see it through wouldn't even start - most of them didn't "understand" it before they started.
okeuro49 4y ago
A cynic would say that the BBC is preparing the public for the Online Safety Bill, where many small online ventures will become unviable.
- simonswords82 4y ago
  Sadly the beacon of balanced reporting that the BBC once was is now a distant memory. It's politicised, click bait nonsense just like most of the news on the Internet. So your assessment is more than likely accurate.
- postsantum 4y ago
  That's what I thought. BBC and their likes lost all credibility and the first thing the reader should wonder about is what agenda they are pushing today
- revelio 4y ago
  Yes. It depresses me no end that this comes from the BBC. How predictable. You can argue that the Californian sun-always-shines mentality is unrealistic, but you can't argue with the results it generates. Perhaps the British attitude is just normal and not anything in particular, but compared to the attitude of the people at the top it's a culture of defeatism. I think it may also be reflective of the culture and mentality at the BBC specifically, though. It's well known their staff is completely dominated by Guardian readers. These are people whose idea of success in life is taking control of a powerful pre-existing institution. The sort of people who make wild bets on unintuitive beliefs and end up disrupting industries are pretty much opposed to that value system and it shines through in all sorts of subtle ways.
  - okeuro49 4y ago
    I wouldn't usually be so cynical, but I noticed recently how the BBC was responding to the inflation crisis, by somehow making it out to be some external thing that nobody could control, and nobody could have predicted. When in fact there were many people saying that the massive state spending programs during coronavirus, were going to contribute to a high rise in inflation, and that policies such as paying the wages of the entire middle class were not going to come without a cost. The BBC manufactured consent for those state policies, then now act like inflation is some random incident, like the weather.
mindvirus 4y ago
I think the real message is to reflect and know what you want out of life, and to know what you're optimizing for. And not just getting away from your current situation.
opentokix 4y ago
Well, all mentioned in the article do bullshit jobs. "Advisor to high networth individuals" "Career coach" and other bullshit.
strangescript 4y ago
You always here about the 5% that make it, not the 95% that don't. Even when you do its easy to brush off why they failed. "Oh their idea was bad", or "they didn't know what they were doing". This is only amplified further by those 5%'ers running around encouraging everyone to start a business. Writing books about their success. Giving motivational speeches, etc.
- gumballindie 4y ago
  I dont know but most place i read i read about those who fail and about how difficult starting a business is. One can rarely read about those who start small but successful businesses. Usually stories are either about failures or those immensely successful.
- sshine 4y ago
  There's a lot of timing, luck, market fit, retrying. The whole story is never a sample-size of one. Hacker News is pretty good at portraying those who failed five times in a row, those who give up after trying for years, those who seem to get it, and those who persevere.
jwr 4y ago
I can see a number of data points in the comments, let me add another one. I started a self-funded SaaS business fairly late (in my 40s). I was tired of being dependent on others, especially as others mostly failed me in the past. I wanted to be independent: no investors, no bosses, no employees. Just me. It took five years of slow growth to get to a stage where I didn't have to worry about revenue. Do I regret it? Hell no! It's the best decision I've ever taken in my life. I am now very happy with where I am: I have a business that depends on very few external factors and runs well. I don't have to worry about investors doing crazy investory things. I don't have to worry about employees pulling crazy employee stunts (believe me, I've seen a good number of those in the past, and the entitlement of many employees is absolutely crazy). I don't have to worry about user numbers, only about paid subscribers and maintaining slow revenue growth. Nobody pushes me for crazy growth. Most importantly, the business model is simple: my customers pay me because my software improves their workflows. That's it. There is no "monetization", no shove-it-down-your-throat marketing, no tracking, none of that unpleasantness that seems to be dominating today's world. If they like the software, they pay a subscription fee, if they don't, well, they don't, and I have a problem. But so far it seems they do :-) The only thing I had to carefully manage was my engagement: it's easy to get pulled in and work crazy hours, because in a single-person business there is always much more to do than you can possibly ever do. You have to become good at prioritizing, which means identifying the single (ONE!) most important thing at this moment and focusing on that. But you also have to accept that most things will not get done and be OK with it. That was hard for me, but I learned, and I keep sane hours and a good work-life balance. I'm posting this just to provide a counterpoint to many negative comments. PS: if I were to provide one bit of advice to aspiring entrepreneurs, it would be: look for a business that delivers high value to customers with money. So don't start a B2C business that does something easily replicable with a low value. B2B is where it's at.
- randlet 4y ago
  How do you deal with the bus factor as a B2B? I lost a few larger contracts because customers would not risk making a one person business a core part of their workflow.
  - 4y ago
xwdv 4y ago
Overemployment where you hold multiple jobs simultaneously is the far better goal for those who are ambitious and want to make a lot of money these days. Not entrepreneurship. As an overemployed worker, you will work less than an entrepreneur but probably start making far more money than them right away. Overemployment is also more friendly to failure. If you fuck up a job and lose it, it takes little effort to just find a new one. You might even have a severance as a bonus. The entrepreneur will probably just drink beer and spiral into depression as they wrestle with the choice of starting yet another business or finding some kind of job they can tolerate. Overemployment will also force you to have incredible time management, and the high you get from running your day like a well oiled machine delivers far better satisfaction than the terrifying uncertainty that comes with entrepreneurship. Furthermore, overemployment allows you to truly “turn off” in a way entrepreneurship doesn’t. At the end of the day, since you’re just working for another company, your responsibilities are limited. You can push away from your desk and live life stress free. You could be grossing around $500k a year easily as an overemployed worker, meaning that with prudent saving and investment you will have amassed millions in the span of a decade, almost guaranteed. The entrepreneur probably has to work a decade just to maybe get the chance at a similar pay day someday, and for many that day never comes. Entrepreneurship doesn’t carry the same prestige it used to. Nowadays there’s a lot of “entrepreneurs” out there and the term has become a bit derogatory, hence the need for quotes. Indeed, someone is more likely to be a charlatan or just a fucking loser if they call themselves an entrepreneur, rather than an actual successful business owner. Overemployment on the other hand is gaining prestige. Most people are immediately impressed when you tell them you have two six figure jobs at the same time. Imagine how eyes would nearly pop out of people’s heads if you told them you worked at Facebook and Google, at the same time. You can’t bullshit overemployment the way you can bullshit entrepreneurship: two jobs is two jobs. So all you young men take this advice: build the most valuable skill set and knowledge base you can, and get multiple six figure jobs with decent tech companies. The world doesn’t really need another shitty business idea, it needs people who want to work.
Michelangelo11 4y ago
Profiling only two people in an article like this seems like a breach of journalistic standards. If they'd interviewed like 4+ people from very different backgrounds, maybe the article could have packed a punch. As it is, I don't feel like I've learned much of anything from this. I mean, surely it's unsurprising to anyone with some life experience that, as with any career choice, some people regret entrepreneurship, and here are two examples of that, and -- so what... ?
sshine 4y ago
I don't regret not starting a business. But I've always wanted to start a business. At the least I could have something to regret.
yawnxyz 4y ago
What's worse: failing to start a company, or believing your skills and your job are going to keep you safe/secure and create a sustainable life and retirement? At this point, they're probably equally risky.
- elforce002 4y ago
  Interesting take. My parents were risk averse and work until retirement age. My father told me he doesn't regret being employed but times change, companies are not what they used to be, and the way things are going it'll be better to just pick a niche and try to come up with a startup. This is coming from a person who didn't go to college and got his house, cars, vacations every year, etc... all that just by working a 9-5 job. Company loyalty and career development is almost not existent. Things have changed for the worse and we might as well give it a shot.
- NineStarPoint 4y ago
  Well if your skills and your job are considered static, yeah that’s equally risky. If you have the ability to keep learning and evolve with the job market, then no I think that’s still a much safer option. Or maybe it’s better to say that starting a successful company is extremely reliant on your ability to have insight into what need in the market isn’t being filled and how to monetize that need (or what needs can be created, if you’re extremely ambitious). If you can learn quickly, navigating “what skills will existing businesses pay a premium for” takes much less insight in comparison.
simonebrunozzi 4y ago
Super important to know what Ergodicity is [0], and how it affects the chances of someone (e.g. from middle class) "rising" to the top. [0]: https://en.wikipedia.org/wiki/Ergodicity https://en.wikipedia.org/wiki/Ergodicity

170 points by pmoriarty 4y ago

I say that the need to start your own thing is a bug not feature. It IS a hard life, with tons of risk, change, and uncertainty. My wife hates the instability of it all. I've missed or worked through many vacations, concerts, and other things over the years. It's not even clear that it's a good deal, when you factor in opportunity costs, hours worked, and chances of success. So, it if you don't have to do it, don't do it. You're not going to succeed unless you are just the kind of person who can't be happy going down another path. It all sounds harsh, but it's actually a lot better than the risk/reward offered in many other fields: acting, writing, sports, etc. This is just how professions with tournament-style payouts work, and you either buy in or you don't. Know thyself...it never pretended to be anything else.

gumballindie 4y ago

“But as evidenced by the collapse of Silicon Valley Bank in March, which left many small firms without access to their essential accounts” Yeah as if that happens every day. This sob story was clearly written by someone who has no clue what running a business means.

known 4y ago

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ttcbj 4y ago

This article is super generic. It could have been written about any career path -- Some people who dedicate their careers to ascending in a single corporation regret it, Some people who aspire to be corporate lawyers regret it, Some people who become ski instructors to have more time to ski regret it. Careers are long, and I think the key is to try things, learn what suits you, and generally try to evolve towards things that are a better fit for you.

game_the0ry 4y ago

One thing that I did not see discussed in the article but I think should be contemplated - when your business goes bust years down the road, it is not easy to go back into the job market. My dad had successful business he started in his 40s, but it failed in his mid 50s. He was engineer before, so it wasn't like he could just go back in the job market. Those were very difficult years.

SlickStef11 4y ago

“Whether you think you can, or you think you can't--you're right.” https://matt-rickard.com/reasons-to-do-a-startup https://matt-rickard.com/reasons-to-do-a-startup

bobleeswagger 4y ago

Regret is a natural part of any long term choice.

idopmstuff 4y ago

I started and run an e-commerce company, and my best advice before starting a business is to think very little about what you want your product to be and a whole lot about what you want your lifestyle to be. Want to have relaxing end-of-year holidays? Don't start a B2B SaaS company in which you're going to close a huge % of your yearly revenue in the last few days of the year. Want to be able to travel? You're probably better off with an internet business than a brick-and-mortar store. Want to be able to eventually step back? You need to make sure that there's a path to lessening your involvement over time without hurting the business. I started mine during the pandemic and got it to profitability. It's not world-shifting money, but it produces solid cashflow. At that point, rather than trying to raise money and aggressively scale, I automated as much as I could. Got a manufacturer to make the products. Found a 3PL to handle fulfillment. Went through all the common types of support emails I got and made sure those questions were addressed proactively in the product or emails, so I get basically no support emails. Handed off bookkeeping to a professional. Some of that has changed (the 3PL was terrible and for now I'm doing some fulfillment myself and using Amazon for the rest), but overall I'm only spending a few hours a week on the business. I write marketing emails, ship some product and place orders for stuff as needed. The really nice thing is that I can move things on or off of my own plate as my workload changes. I'm working a full time PM job that I'm loving, and my wife just had a baby, so I might offload the marketing emails soon (but honestly they're super quick and I often just reuse last year's, so that's tough to justify). If I leave my job, I could definitely move manufacturing in house to expand margins. I think more than anything, it's those qualities of the business that make it great for me (definitely more than the product).

james-revisoai 4y ago
> The really nice thing is that I can move things on or off of my own plate as my workload changes. This is the goal! > Want to have relaxing end-of-year holidays? Don't start a B2B SaaS company in which you're going to close a huge % of your yearly revenue in the last few days of the year. Can you tell me more about where this point comes from please? I'm not sure if it's a US-UK cultural difference, but if ever, business tends to close around the financial year ends here (early April), not christmas. If you haven't got something signed in November, it usually doesn't happen till January and UK workers take quite long christmas breaks. Or have I not experienced what you are talking about it?

janetacarr 4y ago

I think what people don't seem to understand is that entrepreneurship is a skillset. You can get better at it by practicing. Like any skillset, you can build a career out of it. And, just like any career, you could end up on the scale of loving it to hating it. I'll admit it's quite a bit harder than any other career though since often you can't look to your peers for advice or examples of success. It's largely a game of taking on risk to provide value to people who will pay for it. If you've never promoted yourself online, how do you expect to learn enough marketing chops to get people to the value you provide with your business; how do you expect to learn enough sales chops if you've never sold anything to anyone before. As for me, I'm just a lowly independent consultant, so make of this what you will, but I understand that I'm slowly getting better at sales and marketing, and understanding the value I can provide to my clients, and what makes my consulting different (and hopefully better) than others. Like a natural career progression, I hope to give myself a promotion by creating and selling digital products one day using the skills I've built at the bottom of the ladder.

nkotov 4y ago

I'm in year five of building companies, three years doing it full-time. I don't have regrets but there have been extreme low point - primarily tied to other people. Firing others. Having investors pull out last second and forcing us to shutdown. Having cofounders quit, or worse, intentional sabotage the team. It takes a certain type of person to want to continue doing this long-term. Most people don't have that. One thing I wish someone told me early was that being consistent is the key. I spent the first ten years of my tech career looking for hacks to just realize the best hack is to just doing things consistently and speak to new people all the time. Once you have your pace set, just running with it and sticking with it results in things to start happening.

theery 4y ago

It definitely looks easier than it is. You have to want it.

rco8786 4y ago

I am 100% certain that many entrepreneurs regret their choices. But kicking off this article highlighting a person whose stated alternative to entrepreneurship was "consistent 7-figures at a management consulting firm" is laughable, as though that's an option for most people.

avidphantasm 4y ago
Yeah, my reaction to that quote was, “well at least probably did less damage to society as an entrepreneur.”
- koromak 4y ago
  Exactly
akrymski 4y ago
I'm pretty sure that the probability of hitting 7-figures in a consulting firm is smaller than hitting that figure as a founder of a startup.
- pg938hkd 4y ago
  Yeah but hitting 300-500k is still quite comfortable
rwmj 4y ago
Plus if he was a management consultant I bet he'd hate it even more.
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jrochkind1 4y ago
I honestly stopped reading right there in paragraph 3 or whatever, it made me too mad. But i still came here for the comments!

osigurdson 4y ago

The YCombinator model seems pretty good. Try something bold when you are young, if it doesn't work out - whatev. The 1%-2% that go on to become successful are able to fund the whole system.

bicijay 4y ago

Great first article to see in the morning, while trying to bootstrap a startup! Today is gonna be a good day.

HeyLaughingBoy 4y ago
And you didn't even need to use your AK.

onion2k 4y ago

One of the things I learned running my first startup was that I really don't enjoy running a business. The mountains of admin work, the never-ending decision making, the constant anxiety of whether or not I made the right call, the pressure to never actually switch off and just work work work, all of the pointless 'networking' with people who're pretending to be interested ... it all adds up to a pretty horrible experience. The high points (raising a successful round, first revenue, first hires, etc) kind of make it worthwhile, and obviously an exit is nice (not that I'd know... I've never got to that point), but I don't think I'd do it again unless I have an amazing idea that I have to build. Anyone who tells you being a C-level person in a startup is fun and glamorous isn't running a real startup.

rsrsrs86 4y ago
I always ask candidates why they want to work at an early stage startup as a developer, and “because it must be fun” is a show stopper. Being a founder is certainly not fun. The good parts are there, like earning money, interacting with your team and seeing them grow, the first round, the first sale. But the job is quite painful itself. Please note that not all startups and founders are / want to be funded with billions of dollars. The true story is that you are going to be overworked and fail 99% of times.
- s1artibartfast 4y ago
  Maybe fun isn't the right word, but the best startup engineers that I've met found great satisfaction in their work. They enjoyed the engineering, the subject matter, and the process of learning. It is closer to the type of "hard fun" one has training and running a marathon, than the "easy fun" of watching a movie or playing a game.
  - rsrsrs86 4y ago
    Yes, it's hard fun :)
- amanj41 4y ago
  Similar to the sibling commenter, I would say it's a matter of semantics. I am one of three developers at a small startup and definitely would describe the experience as fun albeit stressful. The two sentiments are not mutually exclusive. If it's not fun / interesting / challenging, the possibility of options being worth something in future would absolutely not justify the stress of working at a startup

donutdan4114 4y ago

I don’t know that I fully regret starting a business but boy does it suck like 90% of the time. I’m fortunate in that the business does really well, but…. I just can’t stand it anymore. The stress, the boring, the frustrating, the getting taken advantage of, the weekend hours…. I suppose I fell a little bit into the trap of someone wanting to open a cafe because they like being at a cafe… well I like programming, I like solving problems… but running a business (and a successful one at that) is tough. I can see why most CEOs are non-technical, because it’s a special type of sadistic person who would ask for this. I’ve tried steering the ship towards some goal or task that would maybe make things better but there’s no point. The business is on autopilot. The business is like it’s own person with its own wants, needs, desires… and they come first. They always come first. Bending over backwards to keep something running, get some bug fixed, satisfying some customer, putting out fires… takes higher priority than friends, family, personal time, etc… It has to. I can’t let the business suffer. People depend on its success, most of all my family. I can understand why the rich suffer so.

enumjorge 4y ago
> the getting taken advantage of I’ve been thinking of starting my own business and I hadn’t heard of this before. It sounds draining. If you’re comfortable, would you mind sharing an example of how people try to take advantage of you?

FlyingSnake 4y ago

Entrepreneurship is like one of those carnival games where you throw darts or something. Middle class kids can afford one throw. Most miss. A few hit the target and get a small prize. A very few hit the center bullseye and get a bigger prize. Rags to riches! The American Dream lives on. Rich kids can afford many throws. If they want to, they can try over and over and over again until they hit something and feel good about themselves. Some keep going until they hit the center bullseye, then they give speeches or write blog posts about "meritocracy" and the salutary effects of hard work. Poor kids aren't visiting the carnival. They're the ones working it. -- Original comment from notacoward here: https://news.ycombinator.com/item?id=15659076 https://news.ycombinator.com/item?id=15659076

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nightski 4y ago
The world will never be fair, I'm not even sure that is an ideal goal. The best things in my life have come from when I faced adversity, not when I was in a position of privilege. While opportunities are not always equal in quality or number, there are opportunities if you seek them. It's ironic that even though lots of things come down to luck, it's very possible to put oneself in a position that makes it feel like they are very lucky! "Luck" tends to follow those with initiative.
- coldtea 4y ago
  If fairness is not an "ideal goal" what is? >The best things in my life have come from when I faced adversity, not when I was in a position of privilege Does that hold for kids hungry and unable to finish school because their parents don't make enough then? (Or much worse situations)?
  - detourdog 4y ago

throwaway8456 4y ago

I started, boostrapped and sold a SaaS business. By most standards, this was a resounding success. I won't have to work again ever if I don't want to. This being my first company, I was obsessed with it. Towards the end, I burnt myself out, I had neglected my wife and kids for years, and I was just so miserable. I used to love programming, but I could not concentrate anymore. I started developing resentment against the entitlement of the software engineers I would hire. My heart was broken every time I would read articles/comments on HN about how working for a start up is a scam that only benefits the founders. It was time to get out. I was lucky that I sold in 2021, when the multiples were higher than ever. But I have lost my marriage along the way, and I have definitely lost a few years of life expectancy. I really wonder if it was really all worth it. I know at the end of the day though I had to go through that. I had to see it with my own eyes. In the end, things worked out for me. I can't even fathom how I would feel if the whole thing had failed. I really came to the conclusion that most of the time, starting a company is for suckers.

throaway33355 4y ago
From throwaway to throwaway: Would you mind sharing some contact details, or reaching out to throaway33355@proton.me? Am in similar situation and would love to have a chance to reflect with someone who's been through it.
inconceivable 4y ago
i also sold in 2021 when the money flowed easy. i'm not set for life but i could easily go 10 years, longer if i sold assets. eventually the burnout faded, my health improved (knock on wood) and the boredom got to me after 1.5 years and i'm working again. working on personal projects "for fun" is not the same as making money, no matter what anyone says. buying expensive shit is awesome for a while but it gets old. especially if you already have a home you actually like living in and the 'expensive toys and experiences' itch has been scratched for a while because your business was already successful by the time you sold it. i don't want a huge house and i don't need another car or overpriced workstation computer. it makes me wonder what drives billionaires to keep going. they're probably just bored when they're not working. it really might be as simple as that.

rozenmd 4y ago

I wanted to document a regular person's experience building a business while working full time, it wasn't until the end of my third year before I made my first dollar from a stranger on the internet: year 1: https://maxrozen.com/2018-review-starting-an-internet-business https://maxrozen.com/2018-review-starting-an-internet-busine... year 2: https://maxrozen.com/2019-further-reflections-trying-to-start-an-internet-business https://maxrozen.com/2019-further-reflections-trying-to-star... year 3: https://maxrozen.com/indiehacking-3-year-review https://maxrozen.com/indiehacking-3-year-review year 4: https://maxrozen.com/2021-strangers-paid-my-macbook https://maxrozen.com/2021-strangers-paid-my-macbook year 5: https://maxrozen.com/2022-just-keep-shipping https://maxrozen.com/2022-just-keep-shipping In the end, my business has been described as an "internet laundromat", it's definitely not a unique idea, it was a pain in the ass to get here, but I don't regret it.

mportela 4y ago
Great story and write ups. Thanks for sharing it!

gizmo 4y ago

> The start-ups he later launched all ultimately failed. And even now, as a solopreneur, combining freelance consultancy with writing books and developing information-based products, he often looks back with regret at not simply sticking with his job at a large management consultancy in Beirut. He now has a consultancy called "Business Model Hackers LLC". One of his books is titled: "Vision, Mission, Values, Aspirations, Do They Matter?: A Business Professionals’ Guide to Drafting Vision/Mission Statements and Their Purpose in Modern Organizations". I wrote a couple of paragraphs and deleted them, because really, there is nothing left to say.

rchaud 4y ago
Lots of ex-management consultants do this in their 50s, writing books and getting on the paid speaking gig circuit. Any business will have significant marketing and admin work that's challenging to manage. That's true whether you're shilling a book or running a SaaS company renting Shopify plugins to dropshippers.

shubhamjain 4y ago

Both the examples in the article are agency/consulting businesses. There's a reason for that. Such businesses offer no respite of any kind, especially so if you've decided to scale. You're constantly on the hook to find new clients, and to meet the demand, hire more employees, and then, find even more clients because the hires aren't getting utilized enough. And let's not forget about downturns. Even a small dip is enough to left you scrambling to pay your employees. In most cases, the revenue multiple tends to be much on the lower side in the case of a sale. So, don't except a big pay day. I am not saying, product business is easy either. But, consulting business is relatively easier to start and lures you into thinking that it will also be easy to scale, which is an easy trap to fall into. With entrepreneurship, the kind of ship you're driving matters. I don't think there's much to regret when you're running a profitable software business with 80% gross margins and <10 employees. In today's economy, it's not an impossible dream.

davidn20 4y ago

My guess is running a startup is like running a marathon. The idea of it is great to many people, but as people start to train they realize all the work it takes and drop out. People get into things without fully understanding it all the time. The few that really love it or enjoy the process makes it to the starting line.

simonswords82 4y ago
Totally agree. The number one rule of (most) startups is that everything takes infinitely longer than you would imagine. And then, even longer than that still...
slavoingilizov 4y ago
Understanding everything before you get into it is overrated. Belief is a necessary requirement to move the world forward. And that in itself requires some naivety. Otherwise those people who can actually see it through wouldn't even start - most of them didn't "understand" it before they started.

okeuro49 4y ago

A cynic would say that the BBC is preparing the public for the Online Safety Bill, where many small online ventures will become unviable.

simonswords82 4y ago
Sadly the beacon of balanced reporting that the BBC once was is now a distant memory. It's politicised, click bait nonsense just like most of the news on the Internet. So your assessment is more than likely accurate.
postsantum 4y ago
That's what I thought. BBC and their likes lost all credibility and the first thing the reader should wonder about is what agenda they are pushing today
revelio 4y ago
Yes. It depresses me no end that this comes from the BBC. How predictable. You can argue that the Californian sun-always-shines mentality is unrealistic, but you can't argue with the results it generates. Perhaps the British attitude is just normal and not anything in particular, but compared to the attitude of the people at the top it's a culture of defeatism. I think it may also be reflective of the culture and mentality at the BBC specifically, though. It's well known their staff is completely dominated by Guardian readers. These are people whose idea of success in life is taking control of a powerful pre-existing institution. The sort of people who make wild bets on unintuitive beliefs and end up disrupting industries are pretty much opposed to that value system and it shines through in all sorts of subtle ways.
- okeuro49 4y ago
  I wouldn't usually be so cynical, but I noticed recently how the BBC was responding to the inflation crisis, by somehow making it out to be some external thing that nobody could control, and nobody could have predicted. When in fact there were many people saying that the massive state spending programs during coronavirus, were going to contribute to a high rise in inflation, and that policies such as paying the wages of the entire middle class were not going to come without a cost. The BBC manufactured consent for those state policies, then now act like inflation is some random incident, like the weather.

mindvirus 4y ago

I think the real message is to reflect and know what you want out of life, and to know what you're optimizing for. And not just getting away from your current situation.

opentokix 4y ago

Well, all mentioned in the article do bullshit jobs. "Advisor to high networth individuals" "Career coach" and other bullshit.

strangescript 4y ago

You always here about the 5% that make it, not the 95% that don't. Even when you do its easy to brush off why they failed. "Oh their idea was bad", or "they didn't know what they were doing". This is only amplified further by those 5%'ers running around encouraging everyone to start a business. Writing books about their success. Giving motivational speeches, etc.

gumballindie 4y ago
I dont know but most place i read i read about those who fail and about how difficult starting a business is. One can rarely read about those who start small but successful businesses. Usually stories are either about failures or those immensely successful.
sshine 4y ago
There's a lot of timing, luck, market fit, retrying. The whole story is never a sample-size of one. Hacker News is pretty good at portraying those who failed five times in a row, those who give up after trying for years, those who seem to get it, and those who persevere.

jwr 4y ago

I can see a number of data points in the comments, let me add another one. I started a self-funded SaaS business fairly late (in my 40s). I was tired of being dependent on others, especially as others mostly failed me in the past. I wanted to be independent: no investors, no bosses, no employees. Just me. It took five years of slow growth to get to a stage where I didn't have to worry about revenue. Do I regret it? Hell no! It's the best decision I've ever taken in my life. I am now very happy with where I am: I have a business that depends on very few external factors and runs well. I don't have to worry about investors doing crazy investory things. I don't have to worry about employees pulling crazy employee stunts (believe me, I've seen a good number of those in the past, and the entitlement of many employees is absolutely crazy). I don't have to worry about user numbers, only about paid subscribers and maintaining slow revenue growth. Nobody pushes me for crazy growth. Most importantly, the business model is simple: my customers pay me because my software improves their workflows. That's it. There is no "monetization", no shove-it-down-your-throat marketing, no tracking, none of that unpleasantness that seems to be dominating today's world. If they like the software, they pay a subscription fee, if they don't, well, they don't, and I have a problem. But so far it seems they do :-) The only thing I had to carefully manage was my engagement: it's easy to get pulled in and work crazy hours, because in a single-person business there is always much more to do than you can possibly ever do. You have to become good at prioritizing, which means identifying the single (ONE!) most important thing at this moment and focusing on that. But you also have to accept that most things will not get done and be OK with it. That was hard for me, but I learned, and I keep sane hours and a good work-life balance. I'm posting this just to provide a counterpoint to many negative comments. PS: if I were to provide one bit of advice to aspiring entrepreneurs, it would be: look for a business that delivers high value to customers with money. So don't start a B2C business that does something easily replicable with a low value. B2B is where it's at.

randlet 4y ago
How do you deal with the bus factor as a B2B? I lost a few larger contracts because customers would not risk making a one person business a core part of their workflow.
- 4y ago

xwdv 4y ago

Overemployment where you hold multiple jobs simultaneously is the far better goal for those who are ambitious and want to make a lot of money these days. Not entrepreneurship. As an overemployed worker, you will work less than an entrepreneur but probably start making far more money than them right away. Overemployment is also more friendly to failure. If you fuck up a job and lose it, it takes little effort to just find a new one. You might even have a severance as a bonus. The entrepreneur will probably just drink beer and spiral into depression as they wrestle with the choice of starting yet another business or finding some kind of job they can tolerate. Overemployment will also force you to have incredible time management, and the high you get from running your day like a well oiled machine delivers far better satisfaction than the terrifying uncertainty that comes with entrepreneurship. Furthermore, overemployment allows you to truly “turn off” in a way entrepreneurship doesn’t. At the end of the day, since you’re just working for another company, your responsibilities are limited. You can push away from your desk and live life stress free. You could be grossing around $500k a year easily as an overemployed worker, meaning that with prudent saving and investment you will have amassed millions in the span of a decade, almost guaranteed. The entrepreneur probably has to work a decade just to maybe get the chance at a similar pay day someday, and for many that day never comes. Entrepreneurship doesn’t carry the same prestige it used to. Nowadays there’s a lot of “entrepreneurs” out there and the term has become a bit derogatory, hence the need for quotes. Indeed, someone is more likely to be a charlatan or just a fucking loser if they call themselves an entrepreneur, rather than an actual successful business owner. Overemployment on the other hand is gaining prestige. Most people are immediately impressed when you tell them you have two six figure jobs at the same time. Imagine how eyes would nearly pop out of people’s heads if you told them you worked at Facebook and Google, at the same time. You can’t bullshit overemployment the way you can bullshit entrepreneurship: two jobs is two jobs. So all you young men take this advice: build the most valuable skill set and knowledge base you can, and get multiple six figure jobs with decent tech companies. The world doesn’t really need another shitty business idea, it needs people who want to work.

Michelangelo11 4y ago

Profiling only two people in an article like this seems like a breach of journalistic standards. If they'd interviewed like 4+ people from very different backgrounds, maybe the article could have packed a punch. As it is, I don't feel like I've learned much of anything from this. I mean, surely it's unsurprising to anyone with some life experience that, as with any career choice, some people regret entrepreneurship, and here are two examples of that, and -- so what... ?

sshine 4y ago

I don't regret not starting a business. But I've always wanted to start a business. At the least I could have something to regret.

yawnxyz 4y ago

What's worse: failing to start a company, or believing your skills and your job are going to keep you safe/secure and create a sustainable life and retirement? At this point, they're probably equally risky.

elforce002 4y ago
Interesting take. My parents were risk averse and work until retirement age. My father told me he doesn't regret being employed but times change, companies are not what they used to be, and the way things are going it'll be better to just pick a niche and try to come up with a startup. This is coming from a person who didn't go to college and got his house, cars, vacations every year, etc... all that just by working a 9-5 job. Company loyalty and career development is almost not existent. Things have changed for the worse and we might as well give it a shot.
NineStarPoint 4y ago
Well if your skills and your job are considered static, yeah that’s equally risky. If you have the ability to keep learning and evolve with the job market, then no I think that’s still a much safer option. Or maybe it’s better to say that starting a successful company is extremely reliant on your ability to have insight into what need in the market isn’t being filled and how to monetize that need (or what needs can be created, if you’re extremely ambitious). If you can learn quickly, navigating “what skills will existing businesses pay a premium for” takes much less insight in comparison.

simonebrunozzi 4y ago

Super important to know what Ergodicity is [0], and how it affects the chances of someone (e.g. from middle class) "rising" to the top. [0]: https://en.wikipedia.org/wiki/Ergodicity https://en.wikipedia.org/wiki/Ergodicity