Everyone loves to tell founders to never quit. Grind, push through, the only real failure is giving up. I have a more useful rule, and it is almost the opposite.
If customers are paying you, then keep going. If the only money coming in is from investors, quit. You have not found product-market fit, and no amount of grit will manufacture it.
That sounds harsh. It is the kindest thing I can tell you, because it saves you years.
When I started raising for Caribu, I walked into an angel group in Miami with my cute little product and basically said, look at this, give me money. They said no. Then they asked where my friends and family round was. I genuinely did not know what that meant. They explained: that is your rich friends and family each handing you ten thousand dollars to get going. And I said, what friends and family do you have, and can I come to one of their birthday parties?
Then came the kicker. If your own friends and family didn't invest, they said, they must not believe in you, so why should we? That is the chicken-and-egg trap that quietly keeps women, people of color, and anyone who did not grow up around money on the outside of the whole game. Nobody in my circle had ten grand lying around. That is not a signal about the business. It is a signal about who already had access.
So I found a workaround, because finding workarounds is the actual job in the early days. I love being on a stage, I am a former teacher, so I entered every pitch competition I could find. We ended up a winner or finalist in over thirty of them.
Now, most of those wins were vanity metrics. A vanity metric is what you wave around when you don't have the real ones yet. The numbers investors actually care about are revenue, recurring revenue, customer count, and retention. When you are starting out, you have none of those. So you fake it till you make it, honestly: we had a slide that said the crowd and the judges keep picking us, which means there is something real here.
Two things came out of those competitions that mattered far more than the prize money, which was usually stickers and a weird logo anyway. First, every judge's question was free feedback, and I would fold the answer into the next pitch so it never caught me off guard again. By competition thirty, my pitch was a machine. Second, as a consumer product, standing in front of a thousand people and showing it to them was marketing. Our early growth was word of mouth, because when something actually solves a problem, people tell everyone they know.
So here is the test, stripped all the way down. Are real customers paying you real money because you solve a real problem? Keep going, find the workarounds, get scrappy. Are you alive only because an investor topped up the account? Be honest with yourself and either stop or change what you are building until someone who is not an investor is willing to pay for it.
The grind is not the virtue. Solving an expensive problem is. The grind is just what it costs once you have found one.
Next, the part of the journey nobody prepares you for, and everyone romanticizes: what it actually feels like to sell your company.
A note on how this got written: I used AI to help me write this. The stories, the opinions, and the scars are all mine. I just have a very good robot assistant who helps me get them out of my head and onto the page. Which is more or less the whole point of what I do now.