Chapter 24

Small Steps

Once something becomes successful, in retrospect it can seem like an overnight victory. When Pokémon Go attracted half a billion downloads in just two months, earning millions of dollars a day through in-app purchases and advertising, most people thought it was an instant success. But the origin of Pokémon Go actually extends back decades. Founder John Hanke started creating multiplayer games in 1994, at the time experimenting with online maps and photos, a project that Google bought in 2004, turning it into Google Earth. Once at Google, Hanke worked on Google Street View, and then created multiplayer games linked to maps. When a 2014 April Fool’s joke went viral—a video in which Google announced positions for Pokémon Masters—Hanke wondered: Could he combine Pokémon with his maps games? In 2016 Hanke launched Pokémon Go and although by 2020 the company was making $1 billion a year, it had taken twenty years to get there.1 The truth is that, as was the case with Pokémon Go, big breakthroughs are often through small experiments, one after another, day by day, not by big leaps.

A recent study conducted at Stanford underscores the value of small steps. The researchers compared eight startups (two matched cases in each industry) and asked whether it is more effective for entrepreneurs to tackle the tasks required to build a startup all at once or one at a time.2 For example, they compared competitors Zaarly and Paintzen, which were in a race to create online marketplaces. Zaarly seemed to have everything going for it, winning first place at Los Angeles’s Startup Weekend, raising $15 million in funding, and gaining endorsements from Bill Gates, former eBay and Hewlett Packard CEO Meg Whitman, and tech investor Ashton Kutcher. In just eleven weeks, Zaarly claimed to have successfully assembled an engineering team, built robust technology, opened two offices, filed several patents, and launched to the market. By contrast, Paintzen, seemed only to be getting started, chasing a narrower market in painting, and had only just started testing an estimation tool. They didn’t have painters or customers, let alone a launch to the market. Instead they planned to tackle these things later, one at a time, after they had nailed the estimation tool. If you had to invest, where would you put your money? It might surprise you that, in the end, Zaarly’s team failed to get any traction, burning out because they were spread too thin. “We were doing a lot of things poorly,” its CEO admits. “We saw a lot of glimpses of [success], but there was no way to guarantee more of it without just really, really tightening focus.”3 By contrast, by taking small steps one at a time, Paintzen built such a strong platform that they beat out well-funded competitors like EasyPaint and Amazon Home Services.

Taking Small Steps Like a Great Chef

The Stanford researchers concluded that the best way to pursue a new project in an uncertain environment is to take small steps, switching between different demands rather than trying to do everything at once. They suggest focusing on the most critical area (and using backstops for the others) until it is good enough—though not necessarily perfect—and then switching to the next most critical area. It is a bit like preparing a meal. A great chef doesn’t try to stir every pot at the exact same time, nor finish one dish to perfection and then put it aside to spoil while perfecting the next dish. Instead, they juggle the tasks in a series of small steps. The most critical tasks are on the front burner, the less critical items are on the back burner, and the chef rotates them when the one in front is good enough (as opposed to finished), and so on, weaving together a meal.

Juggling small steps helped Aashi Vel and Steph Lawrence to build the successful culinary startup Traveling Spoon, which connects travelers with local hosts. The inspiration for Traveling Spoon began on a trip to Mexico, when Vel recalls seeing “through a window a woman in her kitchen, making dinner,” and feeling the keen longing to be “sharing a homemade meal with this local Mexican woman, hearing her stories and learning about her culture.”4 Vel and Lawrence joined forces to create a new platform to host authentic cultural experiences. But they debated the best way forward. A recently launched competitor in Paris doing the same thing seemed to be pulling ahead of them by doing everything at once.

Nonetheless, Vel and Lawrence decided to proceed one small step at a time. For example, after talking to as many people as possible, they realized that great hosts would be the key to drawing users and fueling future growth. “We spent two years in just [India and a few other Asian countries], really understanding what it is that [hosts] wanted,” Lawrence recalls. Along the way they discovered that some of their assumptions turned out to be wrong. “We thought we would give women in rural villages the opportunity to make money doing what they love … [but] we found very quickly that because we required that our hosts speak English and have access to the internet, that put them into a middle or upper income bracket.”5

Focusing and taking small steps helped them develop simple rules (like “choose hosts who speak English and can access the internet”) and using backstops for the noncritical areas helped them save time and money. “We were so glad that we didn’t spend tens of thousands of dollars building something because we just didn’t know [what was best]…. We can’t decide at stage one what travelers would need,” Lawrence reflects.6

Once they reached a learning plateau where their understanding of hosts was “good enough,” like great chefs, Vel and Lawrence switched to the next most critical activity, in this case figuring out the right geographies to focus on. After spending time exploring this next small step, they developed simple rules like “avoid partier locations” and ideas about how to best recruit hosts. Vel and Lawrence continued working sequentially, tackling one activity at a time until it was good enough, absorbing the most important lessons, and then turning their attention to the next big issue. Ultimately Traveling Spoon grew to become a profitable, sustainable company, hosting food experiences in more than 180 cities in 60 countries. By contrast, the Paris-based food tourism startup that tried to do everything at once failed, their founders concluding that they had never been able to really get traction because they were doing too much at the same time.

Although Traveling Spoon and Paintzen are in vastly different markets, the lesson remains unchanged: You do not have to do it all at once. Taking small steps helps you make more progress and learn more effectively. You don’t have to reach perfection either. Instead you can pause at a plateau, rather than waiting for a peak, which allows you to effectively switch focus to other important elements. Although we are attracted to stories of overnight success, more often the slow, incremental path up the mountain leads to better outcomes.

Use Experiments to Take Small Steps

Thinking of each small step as an experiment can help you move forward, blowing away the fog on the opportunity landscape and creating more confidence with each step. As Ken Moore, chief innovation officer at Mastercard, describes it, small experiments help you “move from a huge number of assumptions [about the unknown], to do work to turn those into knowns.”7

For example, when Nathan’s students wanted to create a baby monitor using wireless pulse oximetry to monitor an infant’s oxygen levels and warn parents about breathing problems in the night, they faced a forest of unknowns. Hardware is complex and expensive, big players dominate the distribution channels, and they were inexperienced undergraduates. Rather than try to tackle every uncertainty at once, Nathan encouraged them to focus exclusively on the most important unknown: Would customers want it? After initial conversations with parents proved promising, they created a video that was “nothing more than smoke and mirrors showing what the product would do.” It got picked up by media outlets, leading to tens of thousands of inquiries from urgent parents writing, “Just sell it to me now.”8

With the uncertainty around customer demand resolved, they turned their attention to the next unresolved uncertainty: Can we build it? Even though the team had limited engineering skills, they realized they could still develop a prototype. With only $2,000 they managed to build a functional prototype, proving that the idea worked, but also revealing an important design flaw—they needed to change from an easily dislodged ankle monitor to a snug sock. With the technical uncertainty resolved, the next big unknown was what price they could charge customers. To explore this question, they called thirty baby stores to ask what prices parents pay for baby monitors, which for the time was good enough. Later, when they wanted to get a more precise understanding of the optimal price, they ran an A/B test on their website offering that customers could “Reserve Now” at different prices.

At some point along the way, the team discovered that if the device had an alarm, it would require an expensive FDA approval process. Rather than give up, they asked a different question: Would parents still buy a baby monitor providing great data but without an alarm? To experiment about this unknown, they printed out pictures of their product and three competitors’ products and stood outside of baby stores asking parents, “Which one would you buy?” They were happily surprised to discover many parents wanted their product the most.

The team faced much competition, including teams founded by alumni of Google, IDEO, and MIT. But in founder Kurt Workman’s words, “We had experimented … and we knew better than our competitors that what parents wanted most was not the data, but to know everything was OK.” Through hundreds of small steps, the team succeeded in commercializing the Owlet baby monitor, rising to number one in their category and going public at a billion-dollar valuation.

Anyone Can Experiment, Not Just “Innovators”

Experimenting can seem like something only innovators can do, but we would argue that it is the other way around: being willing to experiment is what creates an innovator. Back in 2001, an undistinguished university graduate was struggling to stay positive in his first job, making cold calls to sell data storage, until one day he asked himself: “What if I tried something completely different for forty-eight hours?” Instead of making calls during the day like everyone else, he started making calls morning and evenings, and rather than following the script, he decided to just ask questions to customers. During his liberated daytime, he studied the technical details of the data storage so he sounded more like an engineer than a salesperson. By catching clients during off hours when they were less stressed and asking them questions, in the next quarter he outsold the competitor’s entire office. That lowly employee, Tim Ferriss, today a popular author, reflects on that experience arguing that “success, however you define it, is achievable if you collect the right field-tested beliefs and habits.”9

Get Moving, Keep Moving

Albert Szent-Györgyi recounted how during World War I a group of Hungarian soldiers became lost in a blizzard in the Alps. To everyone’s surprise, they made it out alive, stumbling into camp days later. When their lieutenant asked how they found their way back, the soldiers credited the map they had found in their packs. But when the lieutenant inspected the map, it was of the Pyrenees, not the Alps!10 The story has since been retold many times to teach an important, enduring lesson: getting started is more important than having all the information. As Charles Gorintin, cofounder of one of Europe’s fastest-growing insurance companies explains it, “We encourage our leaders to make a decision with seventy percent of the data because making a decision is often more powerful than delaying a decision. Even if you make the wrong decision, if you just get started, you have time to figure out the mistake and fix it.”11

Creatives and innovators consistently harp on the importance of just getting started and then creating an environment that helps you persist. Cartoonist Scott Adams recounts how he hated his job and commute, so he created a routine of rising at 4 a.m. to draw, which eventually led to the wildly popular comic strip Dilbert.12 Author Brad Modlin purposely didn’t sign up for internet service at home so that at night he could focus on writing.13 Creative Jessica Abel argues that the idea of “the starving artist in the garret, the heroic paint-spattered painter with a whisky in hand … [is] super destructive in terms of how people think creativity is supposed to work. Creativity comes out of coming back to the ‘thing’ over and over again—by confronting yourself with it, letting yourself sit with it, and then moving forward bit by bit. That’s how things get finished.”14

Hard Work

Experimenting is hard, but don’t let that stop you from getting started. Annemarie O’Sullivan is a former competitive swimmer who was working as a coordinator in a local hospital when she took a course on basket weaving. Just feeling the willow branches in her hands “felt like swimming again, it was just so natural. I just wanted to do this.”15 Despite recognizing her calling, she persisted in her hospital job in which she felt ever-decreasing interest. Months later, she was crabby and frustrated, and her husband Tom, observed, “You seem really calm and happy when you are weaving.” Annemarie snapped at him, “Of course I am! Can’t you see this is what I want to do?”

Tom replied calmly, “You can.” Annemarie was thunderstruck. They were in the middle of two careers, with two young boys in tow. Could it be possible? But Tom, a thoughtful and generous companion, sat down and together they came up with a plan. Tom started a landscaping business that would cover living expenses. “It wasn’t my passion,” Tom admits, “but it let Annemarie start weaving.” From there, it was a series of “tiny, tiny steps,” she recalls. “It was a lot of hard work,” and “you have to be prepared for things to go wrong.” But the basket orders started to trickle in until one day a huge order came in from a chic San Francisco boutique. Tom suggested that he close down the landscaping business and join her full-time. Today they work together and their baskets, using traditional methods and heirloom varieties of willow, have been featured in museum exhibitions, galleries, and the New York Times.

Reflection and Practice

Wes Anderson is one of the most distinctive and influential filmmakers of our time. His career started because he was willing to run experiments. He recalls how in the beginning he had no more to go on than questions. “Maybe it should be like this … I think maybe this is the lens? And this is the shot? And this is the angle? This is the feeling?”16 Success came one step at a time. Some experiments worked and some failed. His first big break, a thirteen-minute short with friends Luke and Owen Wilson, won critical acclaim. But when they were funded to create a feature-length movie based on the short, the resulting film Bottle Rocket flopped. Anderson describes the experience as a Cinderella story in reverse, with an emphasis on turning back into an ordinary pumpkin at the end. Still, Anderson continued experimenting, ultimately creating films that have won scores of awards.

Despite his success, he continues to experiment. When asked to curate an exhibit at Vienna’s Kunsthistorisches Museum, he and partner Juman Malouf designed a room full of the empty carrying cases for precious things (without the things themselves) such as cases for Italian crowns and archaic instruments, as well as a room containing only emerald green objects. It was not an easy exhibit to develop. When they asked curators for a list of emerald green objects, the curators just rolled their eyes. Some reviewers panned the exhibit, but many found it enlightening, allowing them to appreciate objects that had been locked away in warehouses for decades. Afterward, Anderson reflected that “should our experiment fail … we are, nevertheless, confident it will, at the very least, serve the purpose of ruling out certain hypotheses, thereby advancing the methods of art history through the scientific process of trial and error. (In this case, mostly error.)”17

We might be more willing to experiment if we realize, like Anderson, that even failed experiments teach us important lessons. Moreover, virtually everything can be transformed into an experiment, even complex, expensive things. SpaceX has a prototype of the Falcon rocket laid out so teams can experiment with changes in advance. IDEO likes to test building layout changes with cardboard mockups before knocking down walls for remodels. To get started on your experiment, here are some questions to ask yourself.

  1. What decision, project, or idea could you transform into an experiment? How could you break it down into a smaller, faster test?
  2. What is the deal-breaker assumption that needs to be tested? Take that hypothesis and find out whether it holds or not using a low-cost experiment. For example, Jennifer Hyman and Jenny Fleiss identified the most critical questions that could undercut the idea for their company, Rent the Runway: are women highly motivated to rent a designer dress for one-tenth the price of buying it, and will they return it in good condition? To test this question, they broke the unknown down into something they could test with a fast, low-cost experiment: they borrowed dresses and set up a rental room in a Harvard dorm before a big dance. Hyman and Fleiss observed that 34 percent of women who visited the booth rented a dress and 96 percent returned it in good condition. This seemed encouraging, so they repeated the experiment several times, first by allowing women to see the dresses at the kiosk but not try them on, and later by skipping the kiosk and simply sending an email offering dresses for rent. Each experiment helped them discover the opportunity and today, hundreds of experiments later, their company Rent the Runway has over $100 million in revenue.18
  3. If you want to change jobs, how could you turn it into an experiment that would give you a better idea of what the new opportunity would be like? Can you volunteer part-time to explore the new job? Can you save some vacation days and do a week-long internship in the new position? Could you set up an option to return to your existing job while you try something new? How about just taking people who work in that organization or job for coffee?
  4. Want to change the course of your life? How would you do it as an experiment? It may help to revisit chapter 7 on regret minimization, including the idea of transforming “one-way door” situations into “two-way door” options.
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