The Ex-Monk Who Founded An App With $100 Million Annual Revenue

Oct 05, 2020
 Created by Author — original image from Wikimedia Commons


Early adulthood was cruel to Andy.

He narrowly missed death when a drunk driver plowed into his friends after a night out. Two of his friends weren’t so lucky and a dozen others ended up in intensive care. Within months, his stepsister died in a cycling accident and an ex-girlfriend passed away from cancer.

The psychological effect was devasting, I couldn’t begin to imagine his pain. He couldn’t shake the feeling of something being missing in his life despite a daily meditation practice and loving his sports science degree. This uneasiness led him to take the drastic step of flying to the Himalayas to become a monk.

For the next 10 years, he traveled across Asia and Europe to unlock the secrets of his mind. Incredibly it was a circus arts degree that brought him back home to the UK. He started a small practice in the backroom of a doctor’s office where he set about changing the way people viewed meditation. Here he met Richard Pierson and together they launched Headspace.

Today the app has been downloaded 65 million times and is worth over $250 million. Andy has transformed countless lives for the better. This isn’t your typical success story of programmer strikes big. It’s something so much more.


Find your mission before even thinking about the business

Do you know what Andy didn’t do? He didn’t make a grand plan at 22 to do a bunch of cool things just so he could become rich later in life.

Sometimes entrepreneurs can be so focused on making money and hustling they forget the best ideas come from living. No one would have told someone to spend 10 years as a monk to become a successful digital entrepreneur in 1994. Andy followed his heart and even gave up all of his material possessions during his journey.

He spent the last few years of his Tibetian monastic service in Russia where stressed locals and ex-pats would visit him for advice. It was in Moscow he realized his monk clothing stopped his message from being heard clearly. It mystified meditation and made people believe they could only achieve it by going to extremes.

Now Andy had a mission, he was going to educate the world and change lives. For years this was just one-to-one sessions and he became effective at spreading his message. This is what allowed him to create a multi-million dollar business.

  • Bill Gates wanted to put a computer in every house.
  • Steve Jobs wanted to create tools for the mind that advanced mankind.
  • Mark Zuckerburg just wanted to create a community.

Everything got bigger afterward because they chased non-monetary goals initially. First, figure out a way you can change the world for the better then find out if it works as a business.


Find a co-founder who is the chalk to your cheese

A Tibetian monk and a workaholic marketing manager walking into a bar sounds like a bad joke rather than the start of a company worth $250m.

The split worked better than either could have expected because of they shared a mission. They wanted to demystify meditation and spread the benefits to more people. Andy provided the wisdom and the soothing voice while Rich handled all the backend and business side. Both knew what they were good at and luckily they covered each other’s flaws.

Disaster struck Andy early into the app’s existence when he was diagnosed with cancer. Headspace had temporarily lost its main attraction and the reliance on one man became clear. Andy found it “amazing to watch the capacity” Rich had to cover his entire role by learning how to do all the events Andy previously did.

If you can find a cofounder whose skills complement yours and who can step up when you need time off then you’re on the right path.


Don’t forget ideas you originally hated

Andy dismissed his cofounder’s idea for an app straight away in their early discussions. He wasn’t tech-savvy and it went against everything he had learned in his traditional training. Mindfulness was best taught from teacher to student in person or so he thought.

For the first two years, Headspace was a struggling events business because it wasn’t making any profit. The model wasn’t scalable and they were struggling to reach as many people as they would like to. Yet the people who heard Andy raved about him and he was building a celebrity and sports star following.

So they went back to the drawing board and Andy was open to trying the app. The first time around he refused as he didn’t know enough, not because it didn’t further his mission. If he’d been stubborn and kept a fixed mindset, 65 million people wouldn’t have had the pleasure of listening to his soothing voice.

Some business owners fall to the sunk cost fallacy where they’ve made a decision and stick to it no matter what. Andy showed remarkable maturity by overcoming this. There’s no shame in accepting you were wrong and changing strategy later on.


Generosity and kindness > venture capitalists

“I don’t think this idea is going to work, it’s terrible. But if anyone can make it work, I think you two guys can.” — Rich Pierson’s dad

For the first 5 years of Headspace, Andy relied purely on goodwill without any official funding at all. The founders started with their savings and the generosity of their friends and family. Rich’s dad didn’t think he’d ever see a return of his investment but he trusted Andy which made all the difference.

For the first version of the app, a friend gave them free access to his recording studio because he believed in them. The impact of this can’t be understated. It would have been far harder for the company to get going if they needed to worry about costs at this early stage. Without the kindness of their friends and family, Headspace would have never got off the ground.

Isn’t this the dream? Rather than focusing on how to win corporate money to get your idea going, focus on persuading those you know to support your mission. Dirty tricks will not work but becoming the person who others want to help will. Andy proves that nice guys don’t always finish last.


Get legit

Let’s face it, many people think meditation is a load of bull and I used to be one of them. It may seem trendy now but remember the app launched in 2012 when only 4.1% of Americans had meditated in the previous year. It’s increased significantly to 14.2% but it’s still a minority.

Andy had lived experience which proved value to him but he wasn’t naive so the second paid employee Headspace hired was a scientist. The company has invested in academic rigor to show the app does what it says and it’s not just a marketing trick. They built relationships with large corporations to craft professional credibility.

Other companies can be so focused on 101 techniques to increase stats and forget the most important thing about any product; it has to work! Headspace hopes to gain FDA approval in 2020 which would mean doctors can prescribe its meditation sessions and health insurers will cover the costs.

If they can pull it off, it represents a giant leap for the legitimacy of mindfulness practice as a whole, far beyond a single company. It’s inspiring to think of how many people this former monk could help through tough times.


The greatest lesson we can learn from Andy Puddicombe’s success is to stop being obsessed with the early markers everyone chases. You don’t need to be a child prodigy or study coding. He was broke at 32 yet never considered himself a failure. He embraced life like so few of us do and prioritized making a real difference to other people.

He’s a rich man now and if he becomes a billionaire, it seems it couldn’t happen to a nicer guy.

Listen to these interviews and tell me if you disagree.

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