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It's a torturous chaos until it isn't

Even at wildly successful startups, the beginning is gut-wrenching and uncertain, with death lurking arond every corner, and pessimism seems like realism.


When you mention “explosive startup growth,” a few darlings come to mind. Facebook, Slack, now OpenAI, …

I wonder… what did they all look like prior to “year 1” on that chart?

HubSpot is a nice example, because they published that data. They are a proper juggernaut of growth; as of the beginning of 2024, they’re still growing fast past $2B ARR:

When you shift left eight years, the curve looks similar, just with smaller absolute numbers:

Shifting left again, it still looks similar, but now we’re getting to the crux of our investigation: The beginning.

Wait, how long did it take them to get their first 500 customers? Two and a half years?

Yes. In fact, after ending 2006 with just 3 (three!) customers, they ended the next year with only 48 (source). That’s less than one a week on average. For a year.

That is not a growth juggernaut. In fact, that sounds downright bad. Like, maybe you should shut the company down because it’s obviously not working. Or at least, there should be an existential struggle about whether to continue.

What was going on during those first years? What it was not: an obviously bright future with a clear vision validated by a torrent of customers opening their wallets in agreement. OK, what was it?

A barely-controlled chaos, awake at 2:43am worrying about how to make payroll or whether the numbers will look good enough by next spring to raise another round? Unsure which products to double-down on and which to kill, and worried the wrong choice would tank the entire company? Staying bright and cheery on the outside for the press, customers, investors, and employees while that one horsehair suspending Damocles’ Sword is sure looking a little worn out?

Of course it was. It always is.

Then again, the story is the same when the company “runs off a cliff without leaving skid-marks,” never reaching Product/Market Fit; possibly never having extracted a single dime from a single person. The one that really should have shut down.

The same struggle, same uncertainty, same near-impossibility.

And most of the time, it means it’s not working, and should be shut down. Most startups fail.

So how do you tell the difference between the tortuous chaos that leads to unthinkable success and that which leads nowhere at all?

I’m not sure you can.

I mean, there are some questions you can ask yourself. But:

Objectively, what’s the difference between Basecamp v1.0 and any number of knock-offs? All of them “the tool we wish we had so we just build it,” all of them simple, all of them usable by relatively non-technical people, all of them web-based, all of them missing half the features that any given customer wished it had.

Objectively, what’s the difference between StackOverflow and the twenty copycat Q&A websites and thousands of forums? Why was Quora still able to stand out? Could you measure this difference? Could you plot it on a chart?

One thing you know for sure—what doesn’t explain it is a standard “feature comparison chart.” Or financial metrics. Or “social media.” Or whether they raised money. Or whether they went to Stanford. Or whether the market was already there. Or whether the competition was already there.

Or anything else. Even with my roadmap for Product/Market Fit in hand, everything has an exception. I say there needs to be founder fit, but the founders of AirBnB weren’t experienced in hotels or hospitality and the founders of Uber weren’t experienced in car services. And that’s just part of the first of eight steps—there are obvious exceptions to every “rule.”

Take Peldi, founder of Balsamiq Mockups. He blogged a bit, but unlike StackOverflow he didn’t have a head-start with an online presence, and English is his second language. He lives in Italy, not surrounded by an American startup culture. Prior to entrepreneurship he was a lifer at Adobe, so that didn’t prepare him for bootstrapping a company from scratch.

Guess what his growth chart looks like? It’s like Hubspot, but what’s more interesting is what it looked like during year #1:

Balsamiq Markups revenue, 2008

How do you think Peldi felt during those first six months? Do you think the anguish subsided quickly? Or ever? Do you think Peldi was still sure his ideas and execution were good in June? Or even afterward—this was one-time revenue, not recurring, so it could stop at any time.

Or more recently, Nathan Barry at Convertkit. How did it feel in January 2015, more than two years in and almost nothing to show for it?

ConvertKit’s early MRR growth

Or more recently still, Pallyy, with two years of making less than $3k/mo in MRR, and then it changed:

Pallyy’s four-year MRR

And it’s not just startups.

Zen and the Art of Motorcycle Maintenance book cover

Robert Pirsig’s book Zen and the Art of Motorcycle Maintenance was rejected by 121 publishers. How do you keep going after “just” 100 rejections? After 20 even?

Then it was published by William Morrow & Company in 1974 and stayed on best-seller lists for decades, with total sales of over 5 million copies. For comparison, Dr. Seuss’s Green Eggs and Ham has sold 8 million copies.

Speaking of Dr. Seuss, he was rejected by 27 publishers before Green Eggs was published. Stephen King’s Carrie was rejected 30 times before Doubleday took a chance on it. J.K. Rowling was rejected 12 times. “I was the biggest failure I knew” she said of herself during that time, before she went on to sell 450 million books and be worth over $1B.

It is impossible to live without failing at something, unless you live so cautiously that you might as well not have lived at all—in which case, you fail by default.
—J.K. Rowling

Of course, your struggles might indeed be in vain. The vast majority of authors never succeed. Nor startups. Nor even new product lines inside established companies. Most of the time, it doesn’t work; that’s the hard truth.

But this I do know:

The fact that you’re in over your head, that you almost cannot will yourself to continue, that you’re completely in the dark, that you’re working yourself to an early grave, that you seem to slide two steps back for every one forward, that nothing’s ever good enough, that that your friends and family can’t understand why you’re turning yourself inside out with no apparent progress, that you’re supposed to be enjoying the journey but you’re not, that you yourself doubt whether you’re even capable of this

These things mean you haven’t yet succeeded, but neither do they prove that you’re failing.

It’s always like this, until it isn’t.

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