When The Switch Flipped

What it’s like finding product-market fit after three years of struggle

When the startup I co-founded, Grasswire, failed to raise a round at the last minute, I found myself floating the company’s last expenses personally as I learned we had officially failed. Doing so left me in debt, unemployed, and living in the middle of nowhere with a newborn baby. But that’s a story for another day.

What I want to share today is what happened when I pulled myself back out of that. And how I did. And what changed when I did. And, perhaps most importantly, how that felt.

The Mental State

I think people underestimate the importance psychology has in the way we live our lives and the decisions we make.

For example, I remember talking to one very talented, very smart, very capable individual the day after he was let go from his job. He had been making well into the six figures not long after he dropped out of college, but for one reason or another things weren’t working out.

He told me about how he went golfing with some of his friends, and noticed that there was someone who was being paid to walk around and pick up the extra golf balls that had escaped the driving range.

He explained to me, “Maybe I could do that and I would be good enough not to be fired.”

When Grasswire failed, that is pretty much how I felt, despite my ease in finding a job that was the perfect fit for me.

But, despite finding the job, I was still deep in debt, and, realistically, hadn’t done anything successful or revenue-generating in years.

That hurts. It’s hard to tell yourself you’re worth something or are capable of anything when those are the facts on the ground.

Debt

And added to that misery there was debt. Something I’d avoided so religiously we were able to pay cash when my newborn daughter spent her first week in the newborn intensive care unit.

Yet here I was — eyeballs deep in it with my dreams crushed.

I don’t think I ever went more than a couple of hours without thinking of that debt. It was my constant mental companion, and every time I checked my balance I was reminded of how much I had screwed everything up and how long it would take me to climb out of it.

I estimated that if I saved every penny I could and lived, as they say, on “rice and beans, beans and rice,” I would get rid of the debt over the course of one year. One more year of thinking about it every passing moment — I felt powerless to think of anything else, and every time I did I was reminded of how I let down myself, my cofounder, my family, my investors, our employees, and all of our users.

I’m not quite that patient, and I knew I would eventually crumble under the weight of those constant thoughts. So instead of resolving to wait I came up with a plan.

I had been slowly writing a book on growth marketing over the course of the past few years, and I wanted to publish it. I tried finding the time to do so, but between my long commute, young family, and long hours at a startup job it was really, really difficult to do so.

The Book

Instead of trying to do it all alone, I reached out to one of the sharpest growth marketers I had ever met, and convinced him to finish the book with me. And what’s more, we would turn it into a video course, and start preselling it.

The few chapters I had written had already been viewed over one million times, but I had no idea if anyone would ever buy it. We set our Kickstarter goal at $10,000, because that much would cover most of what I still owed, and set it live.

The day we did so was one of the defining moments of my life.

The Struggle

The difficult thing for me to swallow, now, is that despite fighting and toiling hour after endless hour on Grasswire, and despite dedicating my entire life to it for as long as I possibly could and driving visitors most easily measured in the millions, we never truly achieved product-market fit.

The one thing I knew was that life was hard, and getting people to care about something was even harder. And that was for a free product. So I knew intuitively that selling something would likely be even harder.

But nevertheless we finally set the Kickstarter live at 6 AM. I put in the first donation, and then hit refresh as I watched donations from friends and family who took pity on us roll in. In just a few minutes it reached $500 — more revenue than we ever had in the three years of working on Grasswire.

By lunch we had already pre-sold $12,000 in book and video courses, and I knew that I was officially going to be out of debt. As I felt the weight of the world lift off of my shoulders (for what I now recognize to be a trivial amount), we decided to go to lunch. Lunch is when the switch flipped in my mind.

The Switch

On return from lunch I checked the Kickstarter campaign again — $13,500.

We had made $1,500 eating lunch.

I wish I could take a taste of that moment and pass it along to every entrepreneur I had ever met.

We actually had product-market fit for a fairly large and willing market. And because that was the case I made more eating lunch that day than I had in the three years of struggle prior to that.

Product-market fit, it turns out, is somewhat binary. If your fit score is “0” it doesn’t really matter what else is happening.

If it’s “1,” however, the whole world opens up.

I wish I could go back to myself three years ago and tell myself to stop. Calm down, take a step back, and find product market fit — true product market fit. Not, “Hey we had 250,000 visitors yesterday and none of them will ever come back,” but “we showed this to 10 people and they loved it. Better yet, they opened their wallets and paid for what we had.

Until you reach that level, any other efforts to multiply your product are multiplying by the base number — zero.

I think I’ve figured it out now; it all comes down to what Ev Williams said at XOXO, “Find something people have wanted and needed for a long time and take out steps.” Paul Graham says it, “Make something people want.”

It doesn’t matter how long you struggle for, how hard you fight, or anything else that you do, until you finally hit a point where there’s that fit.

When you hit that point you’ll know. A switch will flip in your mind, and you’ll feel the difference. Until you reach that point, don’t worry about optimizing or raising or hustling or doing anything else. Just get to that point where people love and need what you’re creating.

Follow-Up

It’s now been almost three months since we first launched the book. We’ve sold $93,000 worth of the book, and we’ve taken the learnings from selling that original course and turned it into $13,000 of additional revenue for another product.

Time will only tell how things will scale,