Entrepreneurs who regret starting businesses • Hacker News Board

Re: Entrepreneurs who regret starting businesses

#91

Post by Axsuul » Tue, Apr 04, 2023, 1:33 PM UTC

hu3 wrote: post #42

jwr wrote: post #30

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? H…

Thank you for sharing your experience. It's the style of life I want to pursue. I'm starting a B2B SAAS business (the dream) on the side where I also plan to work on my own (no investors, no employees) and maybe be helped by my wife. My question to you is: Do you have experience with free tiers? I'm thinking about having a free tier to lure in customers and allow them to play around with the app without having to com…

I wouldn’t recommend it early stage since it can be a distraction and use up lots of support bandwidth. And you should be focusing on paid customers and the features that will bring value instead. But like everything in business, it depends (on the idea, vitality nature of it, etc)

Re: Entrepreneurs who regret starting businesses

#92

Post by andrepd » Tue, Apr 04, 2023, 1:39 PM UTC

shubhamjain wrote: post #39

FlyingSnake wrote: post #8

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…

[flagged]

> There are thousands of examples that will refute your assumptions.

Someone needs to take a statistics/numeracy 101 class :)

Re: Entrepreneurs who regret starting businesses

#93

Post by ericmcer » Tue, Apr 04, 2023, 1:40 PM UTC

shubhamjain wrote: post #39

FlyingSnake wrote: post #8

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…

[flagged]

Agreed, article was about the emotional impacts of working for yourself vs someone else. GP warped that into some metaphor about classism. Cool but unrelated.

Re: Entrepreneurs who regret starting businesses

#94

Post by TrueSlacker0 » Tue, Apr 04, 2023, 1:41 PM UTC

boplicity wrote: post #74

FlyingSnake wrote: post #8

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…

> Middle class kids can afford one throw. Gotta disagree with this. As someone who grew up middle class, I was fortunate, in a lot of ways, to also learn to be prudent with money. I started bootstrapping microbusinesses with almost no monetary investment. This eventually allowed me to support myself (on a very low budget), and then, later, on a slightly larger budget. Eventually, one of these businesses became succes…

This goes back to Jim Collins book Great by Choice and the idea of Bullets then Cannonballs.

[1]"First, you fire bullets (low-cost, low-risk, low-distraction experiments) to figure out what will work—calibrating your line of sight by taking small shots. Then, once you have empirical validation, you fire a cannonball (concentrating resources into a big bet) on the calibrated line of sight. Calibrated cannonballs correlate with outsized results; uncalibrated cannonballs correlate with disaster. The ability to turn small proven ideas (bullets) into huge hits (cannonballs) counts more than the sheer amount of pure innovation."

[1] https://www.jimcollins.com/concepts/fire-bullets-then-cannon...

Re: Entrepreneurs who regret starting businesses

#95

Post by pc86 » Tue, Apr 04, 2023, 1:42 PM UTC

dazc wrote: post #31

throwaway8456 wrote: post #10

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 t…

'I really wonder if it was really all worth it.' You concede your marriage suffered and suggest the impact on your health was negative, but both of these things could have happened if you were just surviving in a low paid regular job. Don't be so hard on yourself and enjoy your success.

But they were already a programmer, so "low paid regular job" is extremely unlikely. Probably the "worst" they could have done was mid-level dev at a bank in the middle of nowhere making $65-80k/yr, which is certainly doable as half the household income to have a nice middle class life. The math changes in you're in a big city but the income does too.

It's easy to choose destroying your relationships and risking your health when the alternative is poverty. It's not so easy when the alternative is still making twice what the average American makes working in a cubicle at worst.

Re: Entrepreneurs who regret starting businesses

#96

Post by czbond » Tue, Apr 04, 2023, 1:42 PM UTC

FlyingSnake wrote: post #8

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…

Realize the game you and your family are playing.

Middle class have 3 paths out:

- Single shot entrepreneurship

- Repeated entrepreneurship with a job (no free nights or weekends)

- Long term, multi generational wealth building over the course of 40-100 years with a mixture of stable career or above

A wealthy family did the above but a generation or two before you or yours & someone else is reaping the benefit. Don't get mad at someone else because of your own families path.

Re: Entrepreneurs who regret starting businesses

#97

Post by Sebb767 » Tue, Apr 04, 2023, 1:43 PM UTC

endisneigh wrote: post #40

revelio wrote: post #22

Earlier quoted context omitted.

A nice analogy but it doesn't work. There aren't that many entrepreneurs who failed multiple times before succeeding at a business. If you look at the big businesses that dominate the US tech economy, they're all first time founders (Amazon, Apple, Google, Microsoft etc). There are also very few entrepreneurs bootstrapping their own business. Even rich kids go to VC, they aren't usually risking their own funds. Final…

> There aren't that many entrepreneurs who failed multiple times before succeeding at a business. If you look at the big businesses that dominate the US tech economy, they're all first time founders (Amazon, Apple, Google, Microsoft etc). For this analysis to be complete you'd have to look at all companies, not an arbitrary selection of tech companies. Furthermore, tech is unique (and so is the list of your companies…

> Amazon - It's true the name was the same, but the company pre and post 1998 (Amazon as a bookstore, and then Amazon as an ecommerce site, and then the development of what is known as AWS in the early 2000s) was fundamentally different. The only real similarity is the name.

> Apple - Similar to Amazon in that Apple as a name and company had continuity from now to its beginning, but Steve Jobs started Next which you could argue is the DNA of modern Apple (it merged back with the almost then defunct Apple), as well as Pixar.

These two do not really support your point. The grandparent said:

> There aren't that many entrepreneurs who failed multiple times before succeeding

Starting a successful company and then used that basis to branch out into another successful company does not disprove this point.

Re: Entrepreneurs who regret starting businesses

#98

Post by melenaboija » Tue, Apr 04, 2023, 1:44 PM UTC

boplicity wrote: post #74

FlyingSnake wrote: post #8

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…

> Middle class kids can afford one throw. Gotta disagree with this. As someone who grew up middle class, I was fortunate, in a lot of ways, to also learn to be prudent with money. I started bootstrapping microbusinesses with almost no monetary investment. This eventually allowed me to support myself (on a very low budget), and then, later, on a slightly larger budget. Eventually, one of these businesses became succes…

I think you missed the point.

As middle class you can't fail with your dart, you are either lucky or good with it. Maybe you are part of the latter, but if you miss your shot you are fucked in either case.

Wealthy people can be damn bad with it but keep trying until it works, and if you are rich enough you don't even need to hit the center once and keep going.

Re: Entrepreneurs who regret starting businesses

#99

Post by ttcbj » Tue, Apr 04, 2023, 1:44 PM UTC

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.

Re: Entrepreneurs who regret starting businesses

#100

Post by jotjotzzz » Tue, Apr 04, 2023, 1:45 PM UTC

revelio wrote: post #22

FlyingSnake wrote: post #8

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…

A nice analogy but it doesn't work. There aren't that many entrepreneurs who failed multiple times before succeeding at a business. If you look at the big businesses that dominate the US tech economy, they're all first time founders (Amazon, Apple, Google, Microsoft etc). There are also very few entrepreneurs bootstrapping their own business. Even rich kids go to VC, they aren't usually risking their own funds. Final…

This sounds like survivorship bias.

Rich kids have a golden parachute for a smoother fall than all the other kids. In addition, most rich kids belong to wealthy, well-connected parents who have already built a network for them. Middle-class to poor kids do not have these resources. However, that doesn't mean bootstrapping will not work. But it is harder for them than rich kids to build a multi-million business.