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.

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!

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'm not an Entrepreneur, but I will probably become fairly well-off, slowly by following the Bogleheads strategy.

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 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.

As soon as people found me and saw value for their money.

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.

i'll tell you if it ever happens