Why Playing It Safe Can Be the Riskiest Move: Lessons from Apple and Warby Parker

Ever wonder what drives a company to really shake things up? Is it all about beating the competition, or is there something more at play?

The whole idea of Innovation-Competition Fit might sound a bit formal, but it’s actually pretty simple to understand, totally crucial and can be the difference between the best and the rest.

The truth is not every business manages to nail this concept or in most cases, businesses belive that innovation has to be something completely game-changing.

But those that get it, change their industry, survive, thrive and set the trends others follow.

We’re going to dive into some stories of companies that have done just that. Apple, Warby Parker, and Lemonade—each took a bold step that others hadn’t even dreamed of yet. We’ll break down what worked for them and think about how we can use these insights to do our own thing in fresh, innovative ways.

Apple’s Big Moves: The iPod and iPhone

Back in the late 90s and early 2000s, Apple were struggling. But then, something changed. They didn’t just jump on the bandwagon; they built a whole new one.

It all started with the idea: “a thousand songs in your pocket”. At the time, most legacy companies were still focused on CDs or MP3 players that could barely hold a couple of albums and were difficult for non-techy people to use. Apple saw a gap and thought, “Let’s fill it, but let’s do it style.”

The iPod wasn’t just an MP3 player, Apple built their GTM directly into the product. The iPod was a fashion statement, a tech icon, and most importantly, it was easy for everyone to use. That didn’t stop the innovation though, they set the goal of launching a new product substantially better than last year’s model to keep competition at bay and give customers a reason to upgrade.

Just when everyone thought Apple had peaked, the real invocation was on the horizon. Phones were getting smarter—people started dreaming about a device that could do more than make calls. What did Apple do? They essentially asked, “Why carry a phone and an iPod, when you can have an iPhone?” They were cannibalising their own product with something even better, and that’s a pure Apple style.

Apple’s gamble to push the boundaries showed the world how merging a phone with an MP3 player—and later adding an internet communicator—could change the way we live, work, and play.

Apple invocation was a game changer that created new businesses and markets but not all innovation needs to be at this scale.

Warby Parker’s Clear Vision

In 2010, buying glasses was painful. You had to travel to a store, search through the clutter, squint to see prices and then pay through the nose.

Enter Warby Parker, a group of friends at Wharton who think, “There’s got to be a better way.” And they find it.

Their idea? Sell glasses online, direct to the consumer, at affordable prices. But they didn’t stop at just selling cheap glasses—they made them stylish and turned buying glasses into a fun experience. With their Home Try-On program, you could pick five pairs to try at home for free, totally changing the game.

Warby Parker started a retail revolution that challenged the giants and carved out a niche where they became the trendsetters, all while maintaining a commitment to social good with their “Buy a Pair, Give a Pair” program.

Warby Parker’s Innovation was looking at the holistic customer journey and making it less cumbersome for the user. However, not all innovation needs to be in the customer journey.

Lemonade’s Refreshing Take on Insurance

Now let’s talk about Lemonade. Lemonade burst onto the insurance scene in 2015 with Zest (pad pun, sorry) and a big promise: to turn insurance from a necessary evil into a social good. Using AI and big data, they cut through the red tape typical of traditional insurance companies. You could sign up in minutes, make claims via a chatbot, and not feel like you’re talking to a brick wall.

What really set Lemonade apart was its business model. They took a flat fee from your premiums for operations and gave what was left at the end of the year to charities chosen by their customers. It was revolutionary, shaking up the old-guard insurance industry and aligning their profits with their customers’ best interests.

Both Warby Parker and Lemonade didn’t just meet customer expectations—they anticipated needs customers weren’t even fully aware of yet. By focusing on customer experience and ethical innovation, they rewrote the rules in industries ripe for change.

Lemonade’s innovation wasn’t just the customer journey it was in the way people thought about their business and their market. It was a business model innovation that sacrificed immediate revenue for the brand and wow did it work.


Looking at companies like Apple, Warby Parker, and Lemonade, it’s clear that innovation comes in all shapes and sizes but one thing is true that innovation sets you apart.

These companies transformed their industries by anticipating needs and daring to do things differently.

Consider these points as you reflect on your own business strategy:

  • Purpose-Driven Innovation: How can your innovations serve a greater purpose beyond profit? Is there a way to align your business goals with the broader needs of society?
  • Risk and Reward: Are you prepared to take calculated risks like Apple did, potentially disrupting your own success truly game-changing?
  • Legacy of Change: What kind of impact do you want to leave on your industry? How can your business be remembered for changing the game?

Let these questions guide your thinking to set new benchmarks in your field.

Finally, Tomas Edison said “There is a better way to do it – find it!”

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