"When?" is the Most Important Question for Entrepreneurs. (The Answer: Now?)

When do you launch? When do you act? When do you change? The cofounder of Square has answers.
"When?" is the Most Important Question for Entrepreneurs. (The Answer: Now?)
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13 min read

This story appears in the March 2020 issue of Entrepreneur. Subscribe »

I am an entrepreneur, but I am also a glassblower, and every glassblower has a mentor.

In fact, we all have the same one: Lino Tagliapietra. Glassblowing is the only profession I know where everyone agrees on who the best practitioner is. Nobody knows who the best accountant or mortician or loan shark is, but the world’s best glassblower is Lino. 

Everyone learns from the Maestro, usually by meeting someone who has met someone who has taken one of Lino’s classes. Maestro’s classes are legendary, right down to an admission process that would impress the Harvard registrar. There was even an essay question, and a collection of T-shirts for sale to salve the pain of rejection. It took me 15 years to earn a place, but I was finally admitted. 

Lino’s class lasted two weeks, and during that time, each student was allowed to ask Maestro one question. Everyone obsessed over his or her question, and as a result most questions followed the same format: A student would ask Lino how to do something impossible with glass. We would then sit in rapture as Maestro demonstrated how to do it. But when the day came for my question, none of the other students even paid attention to Lino’s answer, for my question was so basic that they already knew it. Or so they thought.

I asked the best glassblower in the world how to put a simple foot on a bowl.

You’ve seen this before. Imagine any kind of glass bowl, and now imagine it resting perfectly atop a small glass base. That’s the foot — it keeps the bowl upright. Putting a foot on a bowl is not complicated; the basic technique is taught in every beginner class. By this point in my career, I had performed the process at least a thousand times, but I could never get comfortable with the move. Sometimes it worked, and sometimes it didn’t. I had studied different techniques, purchased different tools, but nothing worked consistently. Sometimes the foot would proudly elevate the bowl on top; other times it looked like it had frozen while trying to escape. Every time I needed to apply a foot, I got anxious. So, after 15 years of stress and failure, I used my one question to ask the Maestro how to do this right. 

Related: 4 Benefits of Finding a Mentor

I expected him to answer me as he had the other students, by demonstrating the proper technique, but that is not what Maestro did. Lino told me to make a bowl, which I did promptly. Then he told me to make a foot, which is simply a hot gather of glass taken directly from the furnace and shaped into a tennis-ball-size glob. I made the foot.

He then told me to put the foot on the bowl, but just as I was about to let the hot foot drop onto the colder bowl, he said: Wait. I stood there with the bowl in my left hand and the foot in my right until he gave the second half of the lesson: Now. I let the now slightly less hot foot fall, and it went on perfectly. This blew my mind. 

I was expecting a lesson in how, but Lino gave me a lesson in when. I already knew how — I had been doing the how part right for 15 years. My problem was when. If you make a shape out of glass that is too hot, you can make the shape, but the glass will just collapse afterward. If the glass is too cold, however, it becomes too stiff and you cannot make the shape in the first place. It’s timing, not technique. 

I left the studio that evening thinking about all the other places in my life where I had done the right thing at the wrong time. How many times had I spoken when the other person was not ready to listen? How often had I been too late or too early with the right answer? I saw a cascade of failures over my lifetime resulting from knowing how to do something but ignoring when to do it.

I decided to become a student of when. I wasn’t in search of some formula for perfect timing — I knew that didn’t exist outside glassblowing. Instead, I wanted to learn the patterns that can help us when opportunities arise. And in my study of entrepreneurial companies, several patterns kept reappearing. This is what I want to share with you…now.

Schools teach how. We learn to copy what works, with the emphasis always on the how and not the when. In my various academic studies, I learned how to construct complicated mathematical models, but I never learned when presenting such a model was inappropriate. I learned to reason logically, but I never learned when logic might offend someone. I learned contract law, but I never learned when to just shake hands.

It is difficult to fault our schools for emphasizing how, since it is difficult to study when. Determining how to perform a task means repeating the steps over and over until you achieve a successful result. Once we learn how to do something, the formal learning usually stops. We then learn how to do the next thing.

Related: How to Launch a New Brand: 4 Tips that Work

But timing does matter. So how do we approach it? Instead of trying to see time as an overwhelmingly infinite set of temporal options, I find it easier to just ask, “When should we begin?” There are really only two answers to this question: now and later. Now is often the right answer. In this world of highly similar products, speed is a huge advantage. If you create innovation first, economics tells us that you can profit from it only until your competitors copy you. And there is good reason to believe that you won’t have much time. The history of simultaneous innovation also suggests that someone else has had the same idea, so, again, the reward goes to the first mover. 

In fact, now is so often the right answer that many successful people default to it. They always want to be first. But sometimes, it really is better to wait.

If you are racing through the streets of Europe, the type of race matters. Formula 1 drivers in Monaco wind through streets so narrow that there are very few opportunities to pass. The car in the pole position usually wins the race. But in a bicycle race through those same streets, the leader will often become exhausted before the race is finished, handing victory to those who waited patiently in the slipstream. 

In the world of entrepreneurship, being first is not always best. This is because innovations build on each other. I call it the “innovation stack”: One innovation makes another innovation possible, which makes yet another innovation possible. Innovation stacks are at the core of world-changing businesses; they are the result of entrepreneurs who solve the right problem at the right time by building upon what’s already possible. This means that, when a critical element of your company is outside your control, waiting can be the best option. It’s possible to launch too early. 

Do you recall the first social network? Wrong — it was GeoCities back in 1995. Friendster came next in 2002 and did better. Then Myspace elbowed out Friendster beginning in 2003. Finally, Facebook took over. Why are we not all connecting with each other over Geo chat? Part of the answer is that GeoCities, Friendster, and Myspace all launched before mobile computing was commonplace. Without always-on access to the system, as well as a camera in everybody’s pocket, the appeal of a social network is diminished. 

Should we fault GeoCities, Friendster, and Myspace for not anticipating the looming ubiquity of mobile devices? Each of those companies was OK for its time, but Facebook’s timing was fantastic. Facebook had a dozen components of its innovation stack ready when mobile exploded, and then it quickly purchased Instagram when Instagram was beating it in mobile. 

You can be too early. Quick, name the 18th search engine company. (Ahem — you might want to google that.)

Related: The Complete, 12-Step Guide to Starting a Business

So, what then? If you are purposely waiting for the right moment to move, is there anything to do in the meantime? Yes. The decision to wait implies that at some future time you will have to move, so you still have plenty to do. You work on all the other elements of your innovation stack — everything else that you’re creating — so that when the final element exists, everything else is ready to go.

For example, consider what happened at my company, Square. We began in 2009 by developing mobile card readers — those small devices you can plug into a phone or tablet and then swipe a credit card through. But at the time, Visa and Mastercard had rules specifically prohibiting the kind of technology we were creating. We spent a year trying to convince them to change their rules — and while that happened, we worked on other elements of our innovation stack, with the hope that the last piece would eventually happen. It was a gamble, but when Visa and Mastercard finally agreed to change their rules, the rest of our stack was ready to go, and the gamble paid off. 

Waiting for one element should not impede all the others. This is risky, of course — but most of the entrepreneurs I studied took this same type of risk, even if it made them uncomfortable.

Now let’s talk about moving now.

How does now feel? Well, in my case, I get nervous. Toward the end of my first year at Square, I was actually having “mild” panic attacks about all our unresolved issues. I remember pulling off the road one day and running into a pharmacy and getting a bottle of aspirin to fight the heart attack I was sure I was having. But this was good, in a crazy way. Here’s why: Right feels early. 

If the timing feels right, you are probably too late. That’s because we, as people, move in herds. If the innovation feels right to you, it probably feels right to a hundred other people with the same idea. If it feels too early, in my experience, that’s a good time to leave the walled city. There is no way to know when the unknown is arriving, but it will probably arrive sooner than you think.

There’s a secondary benefit: When you act now, you can actually create change — sometimes supplying whatever the missing element is in your business. In other words, leaping can cause you to grow wings. 

In Square’s case, let’s return to the permission we needed from the card networks. We built a system that violated their rules...but had we not already built the system, Mastercard and Visa probably never would have bothered to rewrite their rules to accommodate us. Our system gave them something to aim for. Once Mastercard (and then Visa) agreed to revise its regulations, the tone of our conversations was basically “Square is cool, so how do we make it compliant?” 

Southwest Airlines has a similar story. It created the low-cost-­airline model, but it did so in an era in the 1970s when the federal government regulated airline prices. It could have waited for the laws to change, but it chose not to. Instead, it proved itself as best it could; it operated only in Texas, which, because it wasn’t crossing state lines, meant it wasn’t subject to federal laws. Soon people took notice of its demonstrably better price, speed, and service — including Massachusetts senator Ted Kennedy, who led the fight to deregulate the industry. By moving before the country was ready, Southwest created the environment in which the country could be ready.

At that point, the big question was: Is Southwest ready to take full advantage? And the answer was yes — it was more prepared than all of its competition.

Related: 6 Ways to Launch a Business

This is an important part of timing. You have to be ready when the missing elements suddenly appear. I have seen the following pattern in dozens of entrepreneurial companies: Their innovation stack begins to function, and then the world suddenly changes; but because their company is still evolving, they can quickly capitalize on this new world order before any other firm can adapt to the new ecosystem. 

At the time of deregulation in 1978, Southwest Airlines had already been flying passengers around for seven years as a small regional airline. But because of its earlier battles with the airlines and regulators, Southwest’s flights, planes, finances, pricing, staff, pilots, passengers, and a dozen other blocks in its innovation stack were ready before deregulation hit. When the change came, Southwest was already in the air doing 500 knots, the only company prepared for a world where leanness and low cost would win the day. It had happy customers, lower fares, better punctuality, better safety within Texas, and a culture that was accustomed to adapting quickly. Now it just had to scale everything up. 

When is not a science. Not even the world’s best econometrician knows exactly when to make a move. Experience helps, but by definition it is impossible to have experience for anything that is truly new.

I find, however, that simply being aware of the temporal components makes my enterprises more nimble. I race to be ready early. But as soon as I feel ready, a voice in my head asks, Is the world also ready? 

If the world is ready, then creating an innovation stack comes with a responsibility to create a market for as many new customers as possible. You are rewarded with a massive market that is nearly impossible for competitors to steal, so long as you can grow fast enough. This is fun, stressful, and necessary work. Your time indeed has come. 


Adapted from The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time, by Jim McKelvey, to be published March 10 by Portfolio, an imprint of Penguin Publishing Group, a division of Penguin Random House, LLC. Copyright © 2020 by Jim McKelvey.

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