Getting Back to The Art of Startup

Let’s talk about why entrepreneurs have a mandate to take giant risks and make crazy decisions.

If you read me regularly, you might get the sense that startup is a numbers game. And when I say “numbers,” you might think that I mean money. I wouldn’t blame you for thinking that. One of my missions as a relatively successful entrepreneur has been to sift through all the bullshit I’ve been told over the last 20 years and pull out the stuff that I believe contributed the most to my success. I write about it here so others don’t have to reinvent the wheel.

If I had to put all those lessons into one sentence, it would be something like: Live the dream, keep an eye on the numbers. Everyone wants to live the dream, no one wants to monitor the numbers. Watching numbers is boring. Plus they go down like 90% of the time. So it’s also disheartening.

But there’s no escaping the fact that numbers in startup are a lot like numbers in sports. Money, profit, revenue, margins, market share, and all the rest — that’s the way to keep score.

While numbers are crucial, they don’t tell the story of how we actually play the game.

The things we do to run up that score come from a mix of data and creativity, science and art. The numbers are the data, the art is the gut — taking in the knowledge that comes from observing, analyzing, and understanding how we live our daily lives, then acting in an effort to make our lives and the lives of those around us better. All good art strives for this, and in startup, the brush strokes we use come from acting out of belief, character, bravery, and the desire to be unique.

Unlike skills in science and math, those softer traits can’t be repeated and packaged. Despite how business may look at times, success isn’t a literal paint-by-numbers path that can be gleaned from a book, a course, or a seminar.

In other words, I can’t give you a bunch of lessons on the art of startup. But art can be self-taught. And that’s something I can help you with.

Maybe some of us get all philosophical and navel-gazey in the dark hours before we get those precious few hours of sleep, but otherwise, most entrepreneurs rarely talk about the drive that keeps them burning oil late into the night.

Sure, some might splash the bottom of their company’s about page with a buzzword-filled mission statement of world-making and life-changing — lately the go-to move is to also add a personal anecdote. But for the most part, entrepreneurs rarely talk about the “why” of what they do.

Which is odd, because the why should be the criteria for every single decision that comes next.

Actors often ask their director, “What’s my motivation for this scene?” Entrepreneurs should be asking themselves this question at every step of the company’s growth plan. This isn’t necessarily an existential quest, although there’s nothing wrong with that in small doses, the questions are more about figuring out the finished product.

Apple didn’t become Apple by accident. But Apple didn’t become Apple because iPhones started flying off the shelves in 2007, or even because Macs started revolutionizing personal computing with an ad in 1984. Steve Jobs may have been a genius, but he wasn’t hearing voices. He was observing, analyzing, understanding, and philosophizing. The numbers told him he was onto something, but it was his gut that was telling him what that something would look like when he got from point A to point B.

This is not easy. We’re all basically discouraged from thinking and acting with creativity and heart when it comes to business. And like I said, I get this, I know that at the end of the day startup can be a numbers game. But put too much trust in the numbers, and those numbers will start to change, recede, dwindle, collapse, whatever you want to call the end of a trend.

Your inner philosopher should never let this happen.

The 21st century seems like a constant struggle between machine and human. Automation and technology are truly wonderful things, and they’re the reason I got a degree and why I put on a shirt with a collar sometimes. But tech without a human touch will always lose.

Cars that drive themselves, realities that are completely virtual, marketplaces where transactions are executed and fulfilled with minimal human interaction — these are all here. But when we completely remove the human element, even when we lean too much on automation and tech to execute, we jump the shark from innovation to straight science.

And no one wants too much straight science in their life. Except scientists.

The rest of us need application.

At my current startup, Spiffy, we wash and maintain people’s cars and we come to them. There are all sorts of technology and automation requirements here, everything from pre-determining what will go wrong with your vehicle next to making sure our techs show up when you want them there.

But we’ve seen over and over again, not just in our space but in a lot of these mobile marketplaces, startups building amazing tech and skipping the part where the tech provides an experience that pleases the customer. All science and no art.

And this applies at every end of the technology spectrum. At my previous startup, Automated Insights, we built software for machines to write articles from data. We weren’t the only startup doing this, but we won because our mission wasn’t to use the most or the broadest data, but to build a result that created the most important insights and present those first.

At the end of the day, it wasn’t about what the machine could do, it was about what the human wanted the machine to do.

Even with these posts I write, I keep a ton of data on them and I have a choice every time I start a new one. I can maximize my audience or I can give the best advice. In fact, my data tells me that this post will fail spectacularly on the former. I’m hoping the data is wrong, but I can live with the result if only a handful of people get this one, because I believe in the advice.

Here’s where we come full circle back to giant risks and crazy decisions.

The hardest lesson for any entrepreneur to learn is that momentum always stops. No matter how revolutionary our product, no matter how groundbreaking our model, no matter how many waves of customers become rabid fans out of the gate, at some point the numbers will go down, and it usually happens at twice the speed they went up.


I’ve learned over the years that while numbers may be able to delay the drop, they can’t prevent it. The only action we can take is to start another cycle that lifts new and old numbers alike. This is where art in startup saves the day.

Taking a methodical or scientific approach to generating another cycle usually fails. Back to Apple, the numbers didn’t tell Steve Jobs that people wanted a better user experience with their personal computing in 1984, his analysis and philosophy did. And the numbers didn’t tell him that people wanted computers in their pockets all the time in 2007. But those same ideas that created Apple were the ideas that eventually saved Apple.

Those ideas will always seem crazy and the risk that comes with them is inherently giant. If startups don’t have this vision, no matter how tight their data and how accurate their projections, they’ll always, always hit the wall where those numbers cave.

So the next time you’re struggling with growth, take a step back, take a high level look. Observe what’s going on with your product, your company, your market, your industry. Hell, take an extended vacation and get back to what people do with the rest of their lives when they’re not using your product.

Then come back to it, fire up the right side of your brain, and produce some art.

I’m a multi-exit, multi-failure entrepreneur. Sold ExitEvent. Building & GetSpiffy. Former Automated Insights. More info at

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