What do you mean by succeed? To me, it's very specific. It is to live without debt or a mortgage in a safe place where I can afford medical insurance (which currently costs me $65,000/year). It also meant being able to spend as much time with them as my children required.
I guess you could say it took me from ages 21-38. If you count study as a child, 12-38.
However by the time I was 23 I was already super happy. I had a good job and could afford to take my girlfriend out a couple times a week. So the times from 23-38 were fulfilling and very enjoyable even though I didn't feel I "made it" until 38.
12: Started reading business books & biographies
16: Kicked out of high school
21: Dropped out of college & started to teach myself programming.
21: Fired from my first job as programmer
23-31: Worked as computer programmer, moonlighting journalist & got lots of free learning materials. Also spent all extra money on books.
25: Got angel funding for a business that sort of failed 3 years later
28-31: Programming jobs. Fired from another one.
34: PM job at Microsoft. Everyone sold their stock options due to dumb things Marc Andreesen said but I kept it all. Stock went up 1300% in the next 4 years. My friends who had been there much longer all seemed to listen to Marc.
38: Retired to due handicapped kid born. Stock was worth $1 million, had to sell it when I left. So $600K after taxes.
40: Bought a business, fixed it up, and it supported us beautifully for the next 20 years. Spent a lot but also saved a lot. HN calls it a lifestyle business. I made, say, minimum salary for an NFL football player. We bought our house for cash in a neighborhood where one of my favorite guitarists lived, but they couldn't make the house payment and moved out. Same for a local newscaster. I bought another house in the neighborhood for cash as an office.
60: Sold the business, now live off investments. Traded the houses for a farm in town.
People usually think of "making it" as a single point in time that's binary. Granted, there's some truth to that: most people will feel fully comfortable with a few millions in their bank account.
But in reality, success can be savored a lot more pleasantly if you allow yourself to be conscientious of milestones and include having a great process of getting there as the definition of success.
I've met so many people (myself included) that burned themselves by thinking they will spend only a few years grinding to reach a certain milestone, and get frustrated when the narrow definition of success they've created for themselves isn't met.
I've also met a few others that have realized the above, usually with burnout then self-discovery, many which also "made it" by the standard definition, but have a strong sense of fulfillment.
Naturally the question is how. For myself, what worked is a mix of taking more risks (becoming a founder at 35+), experimentation and using various techniques (therapy, meditation, the usual suspects) to find what can drive me to work hard but with purpose or joy.
The saying goes: it takes ten years to become an overnight success.
As for the stick or twist question, if your only goal is to make money then twisting whenever it seems to make that more likely makes sense. Most people thrive on doing work they care about enough to stick with when it is hard, and my guess is that gets better results over time.
One bit of practical advice: celebrate the little successes on the way to whatever you may think a big success looks like. Wherever the journey ends up, it's important to enjoy it as much as possible.
I started cdbaby.com in my bedroom, just me, fulfilling orders myself.
It got an immediate great reception from a few people, very thankful, happy to pay for the service, and telling all their friends. So that's how I knew it was worth sticking with.
But still, it was very VERY slow going, like even after 9 months I was only getting a few orders a week. After a year it was a few orders a day. That's when I hired my first employee.
It didn't really take off until FOUR YEARS later, of this continuous slow growth.
In hindsight, looking at the numbers, it doubled in size every year for 10 years. But that didn't look like success until year 4.
So when people say, “I started my business but it's been a few months and it's not a success yet!” I have to tell this tale.
I would define that as success. My definition is the feeling of success in the eyes of the founders, not millions of dollars or whatever hyped up benchmark
Founding engineer 8 times. 5 exits(2 sold shares back to investors, 2 acquihires, 1 acquisition). Never really made any significant money. I would make 10x more if I spent same time at big tech. Milage may vary but my 2 cents if you want to be entrepreneur or work for a startup:
1. Enjoy the process (You can push harder and longer if you enjoy what you do and at the end it won't matter if money doesn't come because any time spent enjoying what you do is already a win)
2. Work with people you like (For founders: don't be single founder, 90% of the times single founders either don't know how to share or no one wants to work with them)
Why didn't you found yourself at any point? I understand gaining experience as a founding engineer, but after a certain point, you need to work as hard as the technical founder, take the same career risk, for way less payout
I am a middle aged man who lives on a sailing boat. A decade in early stage / founding without an exit that's closer to a car crash. Still trying, I don't have the temperament for consulting or corporate.
There's gotta be a ton of people in their 20s working remotely and living on a boat right now. They don't have to bust their ass like an entrepreneur either. They're just normal employees.
It took me about ten businesses and over 20 years to "succeed". I wanted to retire at 35 for as long as I could remember, missed that by 7 years.
Sold Staff Squared in 2022 for a good sum (7 figure), reinvested most of it into Fundipedia.
Sold Fundipedia for life changing (8 figure) sum in 2025.
All businesses were bootstrapped, reinvesting profits to grow them organically.
I'm now angel investing and consulting. I'm posting more about my journey on my personal website over the coming months https://www.simonswords.com
Rough timeline:
2000 - started a computer hardware company called Atlas alongside a speed dating company (that's not a joke, I ran a speed dating company and some other weird businesses).
2002 - switched Atlas to designing websites, stopped selling hardware and associated support - fed up with call outs to fix networks at the weekend.
2004 - started to design AND code websites, grew Atlas out as a custom software shop - had about 10 employees. Made about 10% margin on a good year. Tough business.
Around 2006 - Vowed to find ARR working with our team on various software solution ideas.
2007 - built first version of what would become Fundipedia - a data management platform for buy side asset managers e.g. HSBC/Barclays/LGIM etc.
2011 - got fed up with internal HR admin as we took on more staff. Built internal HR/time off tracking system that would eventually become Staff Squared - a SaaS HR solution for small businesses.
2012 - 2016 - ran Atlas, Fundipedia and Staff Squared - not very well, but never made a mistake that killed these businesses. Although it nearly killed me - super stressful.
2017 - Fundipedia showed signs of promise as clients were coming to us via word of mouth - we did not market it at all. So I put a plan in place to grow Fundipedia and take on challenge of learning more about the asset management space.
2021 - landed massive Fundipedia client. Sold Staff Squared to a private buyer, wound down Atlas clients.
2025 - With Fundipedia leading the sector it was in - busting the rule of 40 it was now a real threat and an opportunity to our larger competitors in the space. I sold to FE FundInfo (who backed by Hg Capital).
It's very important to know when to call it quits. If you are at the point where it feels like there is nothing more than you can do other than wait for a lucky-break, give yourself a hard deadline for an exit and stick with it.
This is what scares me about people raising insanely large $10 million seed rounds. It's too much runway. Takes too long to fail.
It took me 4 years of working on 3 different startups, with 2 different set of cofounders, before I landed on the idea/business that finally became successful.
Two of those failed companies were part of YC. Thank god every investor turned us down. It allowed us to shut down and move on to the next idea way faster.
Edit: If you're a founder sitting on a giant bank account with a startup that you're losing faith in... remember you aren't obligated to spend all that money. Investors will respect you for returning the money and admitting it's time to try something else.
You should almost always stick with an idea for longer than you think. I've had 3 successful projects (one making over 100K MRR[0]) IMO the main differentiator between winning and losing is how fast you are iterating based on customer feedback.
I think about it like throwing a dart at the dartboard. You might hit the bullseye in one shot but usually you'll just hit somewhere random then it's up to you to iterate and find the version of your idea that the market will actually pay for. This is the feedback part of the equation and giving up and throwing random darts may never pay off.
were your projects in spaces you were familiar with? I feel like that makes the dart less random. Also I feel like it's hard to get customers/users on calls
Still haven’t succeeded! I’m on my 8th business since being a teenager. I have lost quite a bit of money. I’ve earned some through consulting. I think for those of use for whom it doesn’t come easy or natural (and maybe, for everyone) you have to identify as an entrepreneur—wanting and even trying isn’t enough. Then let go of all outcomes. Then just move forward every day.
But I haven’t succeeded yet, so I might not be giving the best advice!
Had one business (dev shop) that was successfully aqui-hired - but it took my 10 years to build it.
For last two years working on a startup, pivotel last year to GRC / compliance management. Finally with profit and growing number of paying customers, but still waiting to pay myself a decent salary. Moments of doubt are hiting more often recently, but I still think it's worth it.
Had experience with compliance before, now building on it and learning a ton. Growing number of customers suggest I’m onto something, so doubts are minimal
First company was csper.io (2019), took maybe 3 months till I had my first customer, and then around month 6 I started getting ~1 customer/week, and continued scaling after that. Felt pretty comfortable with the idea and didn't need to pivot/drop.
Second/current one, dmarcdefender.io (2025), took maybe 6 months till I had my first customer, but now it's growing much slower. There's a lot more competition and still trying to figure out where I fit in / how to market it among all the competition. I was originally positioned as a security focused product, but now pivoting to more of a marketing/deliverability product. But to be honest not really sure where it's going, but still fighting the fight.
Overnight with a really solid idea with good timing where I understood the space.
The same idea with bad timing (rentry after a fantastic exit that I juiced with a condition to not renter the space for 3 years and a subsequent launch just prior to covid), never, because I'm not going to spend my own money on getting it off the ground again post covid.
I've got 3 things working now that are 10 years in the making if they ever succeed.
I tinker. Ideas aren't actually worthless like so many people say but the devil is in the time/space/implementation details.
I think the slowdown with ycombinator successea is exactly because they went hard in choosing teams over ideas when the ideas and their framing are in fact reflective of the teams.
What do you mean by succeed? To me, it's very specific. It is to live without debt or a mortgage in a safe place where I can afford medical insurance (which currently costs me $65,000/year). It also meant being able to spend as much time with them as my children required.
I guess you could say it took me from ages 21-38. If you count study as a child, 12-38.
However by the time I was 23 I was already super happy. I had a good job and could afford to take my girlfriend out a couple times a week. So the times from 23-38 were fulfilling and very enjoyable even though I didn't feel I "made it" until 38.
12: Started reading business books & biographies
16: Kicked out of high school
21: Dropped out of college & started to teach myself programming.
21: Fired from my first job as programmer
23-31: Worked as computer programmer, moonlighting journalist & got lots of free learning materials. Also spent all extra money on books.
25: Got angel funding for a business that sort of failed 3 years later
28-31: Programming jobs. Fired from another one.
34: PM job at Microsoft. Everyone sold their stock options due to dumb things Marc Andreesen said but I kept it all. Stock went up 1300% in the next 4 years. My friends who had been there much longer all seemed to listen to Marc.
38: Retired to due handicapped kid born. Stock was worth $1 million, had to sell it when I left. So $600K after taxes.
40: Bought a business, fixed it up, and it supported us beautifully for the next 20 years. Spent a lot but also saved a lot. HN calls it a lifestyle business. I made, say, minimum salary for an NFL football player. We bought our house for cash in a neighborhood where one of my favorite guitarists lived, but they couldn't make the house payment and moved out. Same for a local newscaster. I bought another house in the neighborhood for cash as an office.
60: Sold the business, now live off investments. Traded the houses for a farm in town.
People usually think of "making it" as a single point in time that's binary. Granted, there's some truth to that: most people will feel fully comfortable with a few millions in their bank account.
But in reality, success can be savored a lot more pleasantly if you allow yourself to be conscientious of milestones and include having a great process of getting there as the definition of success.
I've met so many people (myself included) that burned themselves by thinking they will spend only a few years grinding to reach a certain milestone, and get frustrated when the narrow definition of success they've created for themselves isn't met.
I've also met a few others that have realized the above, usually with burnout then self-discovery, many which also "made it" by the standard definition, but have a strong sense of fulfillment.
Naturally the question is how. For myself, what worked is a mix of taking more risks (becoming a founder at 35+), experimentation and using various techniques (therapy, meditation, the usual suspects) to find what can drive me to work hard but with purpose or joy.
The saying goes: it takes ten years to become an overnight success.
As for the stick or twist question, if your only goal is to make money then twisting whenever it seems to make that more likely makes sense. Most people thrive on doing work they care about enough to stick with when it is hard, and my guess is that gets better results over time.
One bit of practical advice: celebrate the little successes on the way to whatever you may think a big success looks like. Wherever the journey ends up, it's important to enjoy it as much as possible.
I started cdbaby.com in my bedroom, just me, fulfilling orders myself.
It got an immediate great reception from a few people, very thankful, happy to pay for the service, and telling all their friends. So that's how I knew it was worth sticking with.
But still, it was very VERY slow going, like even after 9 months I was only getting a few orders a week. After a year it was a few orders a day. That's when I hired my first employee.
It didn't really take off until FOUR YEARS later, of this continuous slow growth.
In hindsight, looking at the numbers, it doubled in size every year for 10 years. But that didn't look like success until year 4.
So when people say, “I started my business but it's been a few months and it's not a success yet!” I have to tell this tale.
what a cool business. were you in the music world before starting this?
You have to define succeed.
I have had small business success in that it gave me and a small number of other people a really good ordinary income for 20 years.
I have never had a breakout success that accelerates to something much bigger than that, despite trying for a very long time.
I would define that as success. My definition is the feeling of success in the eyes of the founders, not millions of dollars or whatever hyped up benchmark
Founding engineer 8 times. 5 exits(2 sold shares back to investors, 2 acquihires, 1 acquisition). Never really made any significant money. I would make 10x more if I spent same time at big tech. Milage may vary but my 2 cents if you want to be entrepreneur or work for a startup:
1. Enjoy the process (You can push harder and longer if you enjoy what you do and at the end it won't matter if money doesn't come because any time spent enjoying what you do is already a win)
2. Work with people you like (For founders: don't be single founder, 90% of the times single founders either don't know how to share or no one wants to work with them)
Why didn't you found yourself at any point? I understand gaining experience as a founding engineer, but after a certain point, you need to work as hard as the technical founder, take the same career risk, for way less payout
I am a middle aged man who lives on a sailing boat. A decade in early stage / founding without an exit that's closer to a car crash. Still trying, I don't have the temperament for consulting or corporate.
> I am a middle aged man who lives on a sailing boat.
literally my goal. hopefully we can meet up on the strait of malaca at some point
Unironically, living on a boat and working on my own thing is my dream right now.
There's gotta be a ton of people in their 20s working remotely and living on a boat right now. They don't have to bust their ass like an entrepreneur either. They're just normal employees.
What is it with boats anyway?
It took me about ten businesses and over 20 years to "succeed". I wanted to retire at 35 for as long as I could remember, missed that by 7 years.
Sold Staff Squared in 2022 for a good sum (7 figure), reinvested most of it into Fundipedia.
Sold Fundipedia for life changing (8 figure) sum in 2025.
All businesses were bootstrapped, reinvesting profits to grow them organically.
I'm now angel investing and consulting. I'm posting more about my journey on my personal website over the coming months https://www.simonswords.com
Rough timeline:
2000 - started a computer hardware company called Atlas alongside a speed dating company (that's not a joke, I ran a speed dating company and some other weird businesses).
2002 - switched Atlas to designing websites, stopped selling hardware and associated support - fed up with call outs to fix networks at the weekend.
2004 - started to design AND code websites, grew Atlas out as a custom software shop - had about 10 employees. Made about 10% margin on a good year. Tough business.
Around 2006 - Vowed to find ARR working with our team on various software solution ideas.
2007 - built first version of what would become Fundipedia - a data management platform for buy side asset managers e.g. HSBC/Barclays/LGIM etc.
2011 - got fed up with internal HR admin as we took on more staff. Built internal HR/time off tracking system that would eventually become Staff Squared - a SaaS HR solution for small businesses.
2012 - 2016 - ran Atlas, Fundipedia and Staff Squared - not very well, but never made a mistake that killed these businesses. Although it nearly killed me - super stressful.
2017 - Fundipedia showed signs of promise as clients were coming to us via word of mouth - we did not market it at all. So I put a plan in place to grow Fundipedia and take on challenge of learning more about the asset management space.
2021 - landed massive Fundipedia client. Sold Staff Squared to a private buyer, wound down Atlas clients.
2025 - With Fundipedia leading the sector it was in - busting the rule of 40 it was now a real threat and an opportunity to our larger competitors in the space. I sold to FE FundInfo (who backed by Hg Capital).
It's very important to know when to call it quits. If you are at the point where it feels like there is nothing more than you can do other than wait for a lucky-break, give yourself a hard deadline for an exit and stick with it.
This is what scares me about people raising insanely large $10 million seed rounds. It's too much runway. Takes too long to fail.
It took me 4 years of working on 3 different startups, with 2 different set of cofounders, before I landed on the idea/business that finally became successful.
Two of those failed companies were part of YC. Thank god every investor turned us down. It allowed us to shut down and move on to the next idea way faster.
Edit: If you're a founder sitting on a giant bank account with a startup that you're losing faith in... remember you aren't obligated to spend all that money. Investors will respect you for returning the money and admitting it's time to try something else.
You should almost always stick with an idea for longer than you think. I've had 3 successful projects (one making over 100K MRR[0]) IMO the main differentiator between winning and losing is how fast you are iterating based on customer feedback.
I think about it like throwing a dart at the dartboard. You might hit the bullseye in one shot but usually you'll just hit somewhere random then it's up to you to iterate and find the version of your idea that the market will actually pay for. This is the feedback part of the equation and giving up and throwing random darts may never pay off.
[0]https://www.zigpoll.com
were your projects in spaces you were familiar with? I feel like that makes the dart less random. Also I feel like it's hard to get customers/users on calls
Still haven’t succeeded! I’m on my 8th business since being a teenager. I have lost quite a bit of money. I’ve earned some through consulting. I think for those of use for whom it doesn’t come easy or natural (and maybe, for everyone) you have to identify as an entrepreneur—wanting and even trying isn’t enough. Then let go of all outcomes. Then just move forward every day.
But I haven’t succeeded yet, so I might not be giving the best advice!
Define "to succeed".
Had one business (dev shop) that was successfully aqui-hired - but it took my 10 years to build it.
For last two years working on a startup, pivotel last year to GRC / compliance management. Finally with profit and growing number of paying customers, but still waiting to pay myself a decent salary. Moments of doubt are hiting more often recently, but I still think it's worth it.
To succeed, I mean product market fit, or the business being healthy enough from the founders perspective with minimal(always non zero) doubts.
Did you have experience in that space? Are you a solo founder?
Had experience with compliance before, now building on it and learning a ton. Growing number of customers suggest I’m onto something, so doubts are minimal
And yes, solo founder.
First company was csper.io (2019), took maybe 3 months till I had my first customer, and then around month 6 I started getting ~1 customer/week, and continued scaling after that. Felt pretty comfortable with the idea and didn't need to pivot/drop.
Second/current one, dmarcdefender.io (2025), took maybe 6 months till I had my first customer, but now it's growing much slower. There's a lot more competition and still trying to figure out where I fit in / how to market it among all the competition. I was originally positioned as a security focused product, but now pivoting to more of a marketing/deliverability product. But to be honest not really sure where it's going, but still fighting the fight.
i decided i’ve succeeded, took myself out of the rat race, spend my days golfing and day trading.
maybe you’ve already succeeded and don’t know it
It took about 2 years to succeed in letting go of that business idea.
i'll tell you if it ever happens
I'm not an Entrepreneur, but I will probably become fairly well-off, slowly by following the Bogleheads strategy.
Which is?
Here[1], you can learn about it. It's simple, but not easy.
For me, it means buying Fidelity 0 funds in a Roth IRA and not selling them.
[1]https://www.bogleheads.org/wiki/Bogleheads%C2%AE_investment_...
Autoinvest diversely and don't sell. Minimize transactions. Never invest based on the news.
Overnight with a really solid idea with good timing where I understood the space.
The same idea with bad timing (rentry after a fantastic exit that I juiced with a condition to not renter the space for 3 years and a subsequent launch just prior to covid), never, because I'm not going to spend my own money on getting it off the ground again post covid.
I've got 3 things working now that are 10 years in the making if they ever succeed.
I tinker. Ideas aren't actually worthless like so many people say but the devil is in the time/space/implementation details.
I think the slowdown with ycombinator successea is exactly because they went hard in choosing teams over ideas when the ideas and their framing are in fact reflective of the teams.
Can you clarify more on your "overnight success"?
I was successful since the moment I was born.