Sean Kim – CEO and Founder of Rype

The biggest breakthrough for me recently has been that no one is going to give you permission to do what you want to do. Only you can, and the sooner you give yourself permission, the sooner you’ll build a life you want.

Sean Kim is the CEO and Founder of Rype, one of the world’s leading language learning platforms online. He’s also the host of The Sean Kim Show, where he interviews NYTimes Bestselling Authors to World-Class Entrepreneurs such as Robert Greene, Gretchen Rubin, Suzy Welch, and more. Check out his blog on

Where did the idea for Rype come from?

I was living in South America for 18 months, and I could barely speak Spanish even after several months. I realized that living in a foreign country means nothing if you don’t have the time and resources to learn the language.

I’ve tried language schools, mobile applications, instructional courses, and none of them worked for me. And it only frustrated me more knowing that I wasted money and valuable time that I can never get back.

The only experience that I genuinely enjoyed and benefitted greatly from was when I was working with a private teacher. It was interactive, fun, and 100% immersive compared to anything else.

But when I returned home to Canada, finding a native speaking teacher that I trusted was nearly impossible. Instead of relying on Craigslist, I reached out to my former teacher in Argentina, and the idea of Rype was born.

Helping busy, on-the-go people (like myself) learn languages online with trusted professional language teachers. A learning experience where you can learn from the best, at any time of the day, anywhere you are in the world. Best of all, offer it for a fraction of the cost complemented with simple pricing.

As someone who dropped out of University, redesigning the outdated educational model was something I became passionate about solving.

What does your typical day look like and how do you make it productive?

My typical day starts by following a morning routine that I try to practice every day. I start with a shower (cold when I can), do a 10-minute meditation practice, and write down 3 big things I need to accomplish for the day.

Having the same routine sounds boring from the outside, but I feel that I need the regular routine to prime myself for whatever may come my way during the day. The stability of how I start my day actually frees me up to be more spontaneous.

How do you bring ideas to life?

There’s really no magic here. I’ve had moments when it takes me ages to upstart a project, and moments when it takes me a few hours.

I think the secret to executing your ideas is ironically to think less and do more. When you start thinking about the little details, it’s easy to get in analysis paralysis mode. I’ve been there many times, and it’s one of the least productive times I’ve had.

What’s one trend that excites you?

To be honest, I don’t know if there’s one specific trend that I’m passionate about. But the combination of multiple trends that can work together is something that I’ll be looking at more carefully.

For example, online education paired up with virtual reality and machine learning.

What is one habit of yours that makes you more productive as an entrepreneur?

Going to the gym is by far the most productive thing. I think every entrepreneur needs to have their one go-to stress reliever that is accessible anywhere, anytime.

If your main stress reliever is race car driving or rock climbing, it’s harder to gain access to these activities at all times. Whereas working out or meditation is something you can do wherever you are, at anytime.

What advice would you give your younger self?

The biggest breakthrough for me recently has been that no one is going to give you permission to do what you want to do. Only you can, and the sooner you give yourself permission, the sooner you’ll build a life you want.

That applies to not only business but in all aspects of your life.

Tell us something that’s true that almost nobody agrees with you on?

Most advice you receive throughout your journey will be bad advice. Be selective in who you ask for advice and be aware of unsolicited advice.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Documenting my journey. Whether that’s recording a podcast, writing on my blog, or in my journal. When I’m down and under, I look back to previous journal entries a year or two ago, and I’m marveled at the progress and growth that I’ve been through in such a short span of time.

What is one strategy that has helped you grow your business? Please explain how.

Content marketing has and always will be huge in my business and any future companies I may start or invest in the future.

It’s almost ingrained as a value-add to the product or service you offer, helps you build a relationship with customers and prospects, while helping you attract more. A triple threat.

What is one failure you had as an entrepreneur, and how did you overcome it?

Not sure if it’s a failure necessarily since I’m still practicing it. But knowing when to think things through slowly and precisely, and when not to think at all. I think many entrepreneurs struggle with this, but I can be very impatient.
I could have saved a lot of time and mistakes just by taking the time to plan on key initiatives within the business.

What is one business idea that you’re willing to give away to our readers?

I think building a similar model to what we created at Rype, but for content marketing would be interesting. Reliability and trust is huge when you’re hiring someone to spread your message online, and it’ll be a big time saver for business owners.

What is the best $100 you recently spent? What and why?

I don’t know about one specific investment, but the combination of paying a slightly higher price for better service or product would be it.

Rather than penny-pinching for everything you purchase, paying for quality has improved the overall quality of my life. This includes purchases in personal and my professional life.

What is one piece of software or a web service that helps you be productive? How do you use it?

I use a tool called Calendly that helps me schedule meetings without the back and forth interaction. That’s probably saved a lot of time for me.

What is the one book that you recommend our community should read and why?

I struggle with this question, because I think timing is a big factor on how a book impacts you. One book can change someone’s life if they’re just beginning their career, while it could be a waste of time for someone else.

If we’re speaking in general terms, Awaken the Giant Within by Tony Robbins, is a book that I will always re-read.

What is your favorite quote?

“Whenever you find yourself on the side of the majority, it is time to pause and reflect.” -Mark Twain