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

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

#1
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

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

#2
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.

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

#3
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!

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

#4
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.

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

#6
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.

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