Why Entrepreneurs Stop Innovating

At some point, every entrepreneur stops innovating. Let’s talk about how to put that off for as long as possible.

Make no mistake, the end of the innovation cycle is inevitable. It’s also necessary. At my last startup, Automated Insights, two years after we were acquired, we decided to go all in and push the sales accelerator to the floor. At that point we had spent over seven years developing, extending, and evolving our product, so this was the moment when innovation became a department instead of a core value.

Now, that’s a natural growth step. What I’m talking about in this post is slacking on innovation when our startup breaks through to a new level of success, whether that’s from none-to-some or a-little-to-a-lot.

We’ve all taken an innovation vacation, maybe without even realizing it. So here are some warning signs that we’re spending too much time and energy basking in the glow of success and not enough time on getting to the next level.

We Fall in Love With Numbers

Data is so awesome. The instant gratification of real time results is the closest thing to heaven in my book. The dopamine rush I get watching each new sale come in, refreshing the browser and seeing each uptick in the KPIs, that’s the best feeling in the world.

Am I right?

And these numbers, that data, they’re incredibly important. At first. Each sale is an opportunity to chase down the source — Why did that customer just buy our product and can we make that scenario happen again?

If we can answer that question, we can create some algebra: X + Y + Z = This much expected revenue. There are also hooks off that formula, experiments we can run to try to tweak, optimize, make the end result bigger. So we do that.

But at some point, that well will run dry, so we’d better be drilling exploratory wells while the rush is on. We’ll need to create new hypotheses that maximize the value of those customers as they flow in.

In other words: We figured out how to get the customer to buy our ketchup, now can we make them buy mustard too? Will they buy fancier ketchup? Did they find any new uses for our ketchup?

It’s so much easier and more fun to just do something we know works and do it faster and harder. Watch out for that trap.

We Start Serving the Company, Not the Customer

Success brings legitimacy. People are buying the thing we’re making, that thing that was just an idea not too long ago. We’re a real company now. So we better act like one.

There’s absolutely nothing wrong with that. To a point.

Now that we’re running a real company, our people need titles and teams and direct reports and indirect reports and committees and tribes and squads and they definitely need an org chart.

Of course, we’ll need meetings. Executive meetings, management meetings, board preparation meetings, revenue meetings, status meetings, all-hands, stand-ups, scrums — and those meetings need agendas, action items, minutes, post-mortems, maybe even pre-mortems.

We’ll need to document and discuss our mission statement, core values, by-laws, codes of conduct and dozens of other processes and procedures.

Please understand that I’m neither kidding, nor being (completely) sarcastic. But please, please, please don’t spend all of your time building your company and not serving your customer. This is where innovation dies.

There’s a time — and a pace — to build the machine that’s delivering the goods. But our big thinkers need to spend at least some of their time, if not most of it, thinking about the customer.

We Go Status Quo Instead Of Doing What Works

Success in startup is precious, especially early, but with that success comes fear, fear of not screwing it up.

That’s natural, but we can’t let too much doubt sneak in with the fear. Remember, we got to where we are mostly by doing exactly what we’ve done. And while it never hurts to streamline what’s working and revamp what isn’t, it’s always a little too easy to start integrating “tried and true” processes into our startup.

It could be PMI, it could be Agile. Doesn’t mean we need it all overnight.

The CEO of a company I advise recently dropped a massive new issue resolution flow chart on me. Via text. “What do you think of this?” she texted. “Overkill,” I texted back.

When we had a chance to talk, she agreed, and we walked through her new six-box, 30-step resolution plan. It was actually astute, logical, and totally necessary. The company was performing, but was starting to splinter, and accountability and preparation was falling off as sales picked up. The weekly all-hands was dragging on for hours, with long minutiae-filled discussions around each issue.

After our talk, she decided on a compromise consisting of two solutions. 1) Keep the all-hands meeting to a listing of issues and the assignment of solvers — who then go away and have that necessary free-flowing discussion that doesn’t hide flaws or make work. 2) Keep the 30-step plan, but introduce it slowly, a few boxes and a few steps at a time, then revisit as warranted.

We let an experiment run too long or not long enough.

When we don’t have a lot of success, we don’t have a lot of customers, and in a strange sense, there’s some comfort in that. We can test the viability of our product, run our experiments, try new features, and so on, for as long as we have runway, essentially for the entire life of the company. When we don’t have enough customers, we might as well have zero.

Dark, but true.

When we do break through, we get our first artificial time limits on making the call between the success and failure of whatever we try next.

Is that new feature getting used? Are the customers finding value in it? Is the problem the UX or that new marketing channel? How much change is too much change? Are we getting too many complaints?

These questions take time to answer, but we really never know how much time. If we’re not careful, we’ll end up pulling a new feature too soon or keeping a dead feature in play too long.

Both of these things happen out of fear of rocking the boat — the success we have keeps us from the success we need. Success never seems fleeting when it’s happening to us, but it is. Always. So treat it that way.


You know this one, so I don’t need to explain much. Just a warning that no one is immune to ego inflation.

It’s not even that success can make us insufferable, but that it can make us stop listening. I can tell you I have never achieved success the same way twice. The minute I think I know everything, I realize I know next to nothing.

There are probably a couple more of these, the ones I’ve listed here are the ones I see the most often and have the most experience with. The funny thing is that they’re all OK, sometimes even necessary. I mean, what entrepreneur succeeds without a good dose of ego?

Just don’t let a little success stop you.