Ask HN: Entrepreneurs, how long did it take you to succeed? How long did it take? How many ideas did you go through? What made you stick to an idea vs pivot? EDIT: People keep asking about the definition of success. Success means you had a venture that was successful from your perspective. Whether that's a small business that generates enough income to replace a day job, or a million dollar exit. I don't consider a side project a success though, would need to be full time |
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 don't want to speak for everyone, but to me he is such a huge inspiration, not only business wise, but also personality wise.
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.
It was an eBay-related business that I had used many times. The resources I used were common sense and a realistic perspective on business, neither of which I was raised with :O. I went in knowing it might be a ripoff so I didn't go into debt. Just used up some of my retirement account.
There was little time for due diligence so I developed a relationship to the owner of the business to help calm my nerves.
Genuinely curious where this might be, the only place I can think of might be Tillamook, OR!
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 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.
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.
literally my goal. hopefully we can meet up on the strait of malaca at some point
What is it with boats anyway?
But I haven’t succeeded yet, so I might not be giving the best advice!
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.
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.
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)
Yes I agree founding is much better than being first engineer. Reason I kept joining as first engineer is because I found product market fit for my self (it's funny to say that haha). I was able to pitch myself as first engineer that builds first product and first teams. Someone super technical who likes to grow code and grow people is actually pretty rare in startup world so I was able to ask for high comp and choose to work on interesting projects.
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).
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.
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.
Due to some perverse incentives in the industry as well as some protectionism and legal chilling none of the players actually solved their customers fundemental problem. They got stuck as these weird tweener lifestyle companies.
I quit, moved to a cheap studio apartment in Brasil for 3 months (we still had a bully in the space put together a bs packet and used their connections to get some FBI agents to show up on our doorstep only to drop everything after our little interview), coded out a marketplace play and launched it.
Ycombinator flew us out but declined and a group in a smaller market gave us the only money we ever had to raise. Due to the fact that we built a legitimately fun marketplace play that solved a lot of frustrations in the space Scott Hanselman tweeted us out to his followers and that was all we needed to get the exposure and google juice ball rolling.
Due to the industries continuing perverse incentives, I could start the same company again tomorrow except it would take a big ad words dump of cash and I don't want to pull out of my own pocket yet again (I did just prior to covid but it's an industry that was totally shut down during covid and I no longer have the appetite.)
So by overnight I mean, we started generating huge buzz in the industry and 10x traffic of established players overnight and middlemen don't have motes so we never really had to raise, it was just the time to code out the platform and get it populated with data at the MVP level.
My next one paid me a salary, but I had a falling out with my cofounder and sold my shares for very little to get away. Success? I felt like it, again, maybe externally.
Two duds after that, one I raised money for so I got paid a salary and I sold it to recoup most of investors money.
The one after that was a big hit: we grew to 50 employees, 8 figures in revenue and 9 figure exit.
I like to say: if I could find the perfect job, it’s much easier to work for someone else than start my own thing. But I have specific interests I want to chase so creating a company is my way to create the “perfect” job for myself. If you take this approach, it’s much more likely to be successful in your own eyes.
Within six months of starting development I had my first customer- who hated my product's bugs, but helped me find and offered ideas for improvements. A year later I was at $30k ARR. That doubled year after year for some time before leveling out. It was enough to live comfortably for ~15 years, but nobody mistook me for wealthy.
No exit opportunities.
I didn't start by dwelling on ideas. Some parity has to come first, then add value. I looked at companies building things of interest to me that I knew to be attainable wrt time and money. I emulated in my own style what they did best, I avoided or improved upon what they did poorly and I shouldered my way into the market. Above all, I listened to my customers and followed their lead.
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.
Did you have experience in that space? Are you a solo founder?
And yes, solo founder.
maybe you’ve already succeeded and don’t know it
There are many people out there who enjoy building. Even if it gets very low traction and doesn't make them life changing fortune, people enjoy it. Along the way, they might make some money. Of course, there are also a lot of people who get on to this journey with the primary goal of making it big. We should not look at the "side-effects" and think that is the cause.
I more latched onto the time and succeed part, that's why I answered at all.
But, I never said that entrepreneurship is only about money, or that it can be replaced, I simply shared a way to succeed in life, which I think is cool.
There is something to be said for wealth equaling success, however. If happiness is success and wealth buys happiness, which it does[1], then wealth is success, in my book. Success is relative, for someone, they could be poor and unhappy, but have lots of kids and think that's what success means. I think it's about happiness in life.
I think it's cool that people can succeed(gain happiness from not worrying about finance, among other benefits of wealth) even without taking on all that risk and burden of entrepreneurship.
I definitely respect people building things. I was just sharing my personal path.
[1] https://www.forbes.com/sites/johnjennings/2024/02/12/money-b...
PS: It seems I started a trend of "entrepreneur" being capitalized, whoops :)
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_...
Ideas came from building something that I wished existed. Honestly I didn't overthink any of them and I'm glad I didn't. If you do too much market research it tends to make your vision seem less exciting IMO.
Either way my whole point is to just iterate on your initial idea for long enough that it goes from being "your fun idea" to "your fun idea that people are willing to pay for". Then just repeat that loop until you retire :)