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Ask HN: Entrepreneurs, how long did it take you to succeed?

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Re: Ask HN: Entrepreneurs, how long did it take you to succeed?

#31

Post by simonswords82 »

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).

Re: Ask HN: Entrepreneurs, how long did it take you to succeed?

#32

Post by tomcam »

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.

Re: Ask HN: Entrepreneurs, how long did it take you to succeed?

#33

Post by asdev »

e9 wrote: post #28

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 a…

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

Re: Ask HN: Entrepreneurs, how long did it take you to succeed?

#34

Post by sivers »

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.

Re: Ask HN: Entrepreneurs, how long did it take you to succeed?

#35

Post by asdev »

sivers wrote: post #34

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 f…

what a cool business. were you in the music world before starting this?

Re: Ask HN: Entrepreneurs, how long did it take you to succeed?

#36

Post by quirk »

sivers wrote: post #34

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 f…

Dude I loved CDBaby. And yes, even 4 years is kind of a short time to be successful (profitable, sustainable).

Re: Ask HN: Entrepreneurs, how long did it take you to succeed?

#37

Post by e9 »

asdev wrote: post #33
e9 wrote: post #28

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 a…

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 founded 2 of the companies above (1 acquihire, 1 sold big portion of my shares back to investors when I left).

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.

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