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

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.

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 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.

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

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.

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.

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.

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.

I was successful since the moment I was born.