Ask HN: Entrepreneurs, how long did it take you to succeed?
Source: Hacker News
You should almost always stick with an idea for longer than you think. I’ve had three successful projects (one making over 100 K MRR). In my experience, the main differentiator between winning and losing is how fast you iterate based on customer feedback.
I think about it like throwing a dart at a dartboard. You might hit the bullseye in one shot, but usually you’ll just hit somewhere random, and it’s up to you to iterate and find the version of your idea that the market will actually pay for. This feedback loop is crucial—throwing random darts without learning never pays off.
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.
It’s very important to know when to call it quits. If you reach the point where it feels like there’s nothing more 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 creates too much runway and takes too long to fail.
It took me four years of working on three different startups, with two different sets of co‑founders, 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 much faster.
Edit: If you’re a founder sitting on a giant bank account with a startup 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.
I am a middle‑aged man who lives on a sailing boat. A decade in early‑stage / founding without an exit feels closer to a car crash. Still trying; I don’t have the temperament for consulting or corporate life.
I am a middle‑aged man who lives on a sailing boat.
Literally my goal. Hopefully we can meet up on the Strait of Malacca at some point.
There are probably 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; they’re just normal employees.
What is it with boats anyway?
I still haven’t succeeded! I’m on my eighth business since being a teenager. I have lost quite a bit of money, but I’ve earned some through consulting. For those of us 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 and just move forward every day.
But I haven’t succeeded yet, so I might not be giving the best advice!
First company: csper.io (2019) – took maybe three months until I had my first customer, and around month 6 I started getting ~1 customer per week, continuing to scale after that. I felt pretty comfortable with the idea and didn’t need to pivot.
Second/current one: dmarcdefender.io (2025) – took maybe six months until I had my first customer, but now it’s growing much slower. There’s a lot more competition, and I’m still figuring out where I fit and how to market it. I was originally positioned as a security‑focused product, but now I’m pivoting to a marketing/deliverability focus. Honestly, I’m not sure where it’s going, but I’m still fighting the fight.
Overnight, with a really solid idea and good timing, I understood the space. The same idea with bad timing (re‑entry after a fantastic exit, with a condition not to re‑enter the space for three years, and a subsequent launch just before COVID) never materialized because I wasn’t willing to spend my own money on getting it off the ground again post‑COVID.
I have three things working now that are ten years in the making, if they ever succeed. I tinker. Ideas aren’t actually worthless as many say; the devil is in the time, space, and implementation details.
I think the slowdown with Y Combinator successes is exactly because they went hard in choosing teams over ideas, when the ideas and their framing are in fact reflective of the teams.