Ray Blakney of

    We Spoke to Ray Blakney of on Being an Effective Leader During Turbulent Times

    As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company,” we had the pleasure of interviewing Ray Blakney, CEO and co-founder of, a renowned online language learning platform. offers a unique and immersive approach to mastering a new language, as it pairs users who want to learn Spanish, French, German, Chinese, and more with their own hand-picked, certified, native-speaking tutor for online teaching sessions. An award-winning Filipino-American entrepreneur, speaker, and podcaster, Ray builds and helps others build 6- and 7-figure businesses on a bootstrap budget using SEO.

    Thank you so much for joining us in this interview series. I know that you are a very busy person. Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you grew up?

    While it seems normal to me, I have been told that my backstory is anything but. I was born in the Philippines to a Filipina mother and an American father (but my American father grew up in Rhodesia). At the age of one, we moved to Turkey, where I spent most of the next 15 years of my life. At 15, I got sent to a boarding school in the US (since the US school in Turkey did not have the last two years of high school). I completed high school and went to university in the US, where I graduated with a B.S. in Computer Engineering. After college, I spent about five years working in Silicon Valley and for Fortune 500 companies as a software engineer. When I turned 26, I had a quarter-life crisis where I saw myself sitting in a cubicle and writing code for the next 40 years. It was not the life I wanted to live. Within a few days of this epiphany, I had applied to join the US Peace Corps as a volunteer. Within three months, I had quit my almost-6-figure job, sold my condo and all my worldly possessions, and was on a plane to Mexico where I would help indigenous communities in the south of the country.

    While in Mexico, I met my wife and after I completed my two years in the Peace Corps, we decided to try our hand at a business together. Our first business was a chain of language schools in Mexico, which we sold in 2012. As part of our language schools, we had online classes — which we started offering in 2009 to help our business survive during the Mexican Swine flu crisis — and we kept that portion of the business.

    The online portion grew into what is today We are one of the largest online language schools in the world, and the only one in the top five that has not received any venture funding.”

    What were your early inspirations that set you off on your particular journey?

    My journey began when I was inspired by a quote:

    ‘If they were to write a book about your life, would anybody want to read it?’

    I remember hearing that quote on a commercial for the US Navy when I was 26 years old. While it did not inspire me to sign up for the Navy, it did get me thinking ‘with what I am doing now, will my life be interesting enough to put in a book?’

    This did not mean that I wanted to, or even now want to, write a book about my life. It just started me down the path to living a life that would be interesting enough to read if I did. Within a month of seeing that commercial, I had quit my job and joined the US Peace Corps. As soon as I finished my two years in the Peace Corps, I launched my first business. That was over a decade ago now and I love the journey I am on.”

    Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

    When I started our business, our first office was in Mexico (even though is registered in Boston). Thus, I was working with primarily native-Spanish speakers, and while I was communicative in Spanish, I was not fluent yet. Like anybody new to the business, I made a lot of mistakes in the job.

    So I would constantly try to say ‘I am embarrassed’ in Spanish. Since I did not know the word for embarrassed at the time, I took a guess and said ‘embarassado’. Embarrassed, plus, -ado. Makes sense? When I said it the staff members would laugh.

    I thought they were laughing because I was being humble, but that was not the case. Embarassado (correctly spelled ‘embarazado’, but it is pronounced the same) means pregnant. I was a male telling everybody I was pregnant. The staff was laughing at me, not with me! The big ‘takeaway’ from that experience is that you ARE going to mess up when you start anything new, whether it is a language or a business. You can either let it bring you down or laugh at it. After learning this, I blushed for a bit, but then went with the latter option.”

    None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

    That one is easy: my wife. She has been not only my life-partner but also my business partner at for the last 12 years and counting. Without her, there would have been multiple times I would have wanted to give up and just get a job that paid me every month.

    One incident that really stands out to me was when we were starting out. This is what led to the revelation of taking a rest vacation every six months as I mentioned in the last question. My idea of how to run a business was, sadly, from movies and what I heard on TV. I thought that to start a successful business, it was all about hustling for years until you finally get your big break, make lots of money, and can enjoy the rest of your life.

    So, for the first three years, I never took a day off and I even worked most weekends. By the end of that time, I was burned out and did not want to work. My wife saw this, and without even telling me, she booked one week in an all-inclusive resort. I told her I did not want to go, but she had already paid.

    The first night we got there, I slept for 14 hours. I did not even realize how stressed and tired I was. By the end of the week, I felt like a new person. Without this intervention, I don’t think I would have reached where I am today.”

    Can you tell us a story about the hard times that you faced when you first started your journey?

    My first business was a chain of brick-and-mortar language schools (which I sold in 2012). My wife and I launched this enterprise in 2008 with just under $2000 US in the bank account to start our business and to live off of.

    We luckily had students from the first week that helped pay our bills and helped us re-invest and furnish our school (the first day we only had two desks). Six months in, we were doing well. The school was fully booked and we were making what to us was a good income at the time.

    Then, Mexico got hit with the Swine Flu. Most of our students had flown in to Mexico from other countries to study Spanish with us. Within a 14-day period, we went from the school being full and booked out for the next three months to all of the students leaving. We received cancellations for most of the students for the next few months. The country even closed its borders for two weeks, and those people who had booked could not come down to our school even if they wanted to.

    At that point, we had a fully furnished school but only enough savings to stay running for 1–2 months.”

    Where did you get the drive to continue even though things were so hard?

    We had no choice. Ok, that sounds a bit more drastic than it was, as we did not risk being on the streets. We both had great parents who would have taken us in as we figured out the next step. I am a computer engineer, and my wife is a bilingual teacher. We would have been fine.

    But if we wanted to live a life we were proud of (a life that somebody ‘would want to read about’), then we had no choice. We had to figure out how to survive.”

    So, how are things going today? How did grit and resilience lead to your eventual success?

    Things are going great. Swine flu was probably the best thing that could have happened to our business. During the Swine flu crisis, we had to find a way not only to pay our bills but also to pay our teachers so they could support their families. It was during this time that we had the idea to offer classes to our former students via Skype. That worked so well and had such a great response that we decided to launch a website to offer that service to the world in general.

    Remember, this was back in 2009 and almost nobody was doing that. This idea eventually became We are now one of the top online language schools in the world and are able to share language learning with thousands of students each year.”

    What do you think makes your company stand out? Can you share a story?

    In a world where every business, including online language schools, is growing for the sake of growth, we have had great success by focusing on staying personal and family-owned. When a student signs up with us, they work with one of our specialists to get paired with their ideal language tutor. We don’t make the students search through thousands of tutors for themselves. We do all the work for them.

    When each student signs up, they get a personal welcome email from me with my direct email address so they can contact me directly with anything they need. A few weeks later, my wife and co-founder emails them as well to see how the classes are going. She runs the academic end of things and is on hand to help them make progress.

    This approach has not only helped us in our business but has also helped us grow our group of friends. We have met with many of our students in person, either when they visit our area or when we visit theirs. I have also had the opportunity to connect with and get to know some celebrities and very well-known CEOs with this approach. It is not why we do it, but it has been a fun and unexpected benefit of being a more personal, family-owned business.”

    Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

    This one took me years to discover but has changed my life. Make sure you plan at least a 1-week ‘rest vacation’ every six months. Never skip it. A ‘rest vacation’ is one where you go to a place where you can entirely disconnect from work (nobody is allowed to call, and you should ideally have very limited internet/email access) and you focus on resting. This is not a vacation where you are exploring a new country or seeing tourist sites every day.

    That can be different for everybody, but for us, it includes going for morning walks on the beach and reading fiction books 10–12 hours a day by a pool. If you do it right, you will notice that about 4–5 days in, you will feel re-energized. By day 6–7, you can’t wait to get back to work. Normally during the first 1–2 weeks after these vacations I not only make up for the lost time but also get more work done than the other five months between the rest vacations.”

    How have you used your success to bring goodness to the world?

    By its nature, we are in the business of bringing people closer together, which in turn brings goodness to the world. At, we not only teach languages with live tutors, but also we make sure the teachers are originally from the country where the language is spoken so that they can also share their culture and history.

    This helps bring together people and cultures that would otherwise never have a chance to meet together and learn about each other. In addition to this, in 2018 we started sponsoring children’s education around the world through Save The Children. Our mission is to bring everybody closer through education, so Save The Children was a perfect fit for us.”

    Wonderful. Here is the main question of our discussion. What are your “5 things I wish someone told me before I started leading my company” and why? Please share a story or example for each.

    Before I started my company, I wish someone gave me these tips:

    1) Be prepared to eat multiple slices of humble pie.

    If you want your company to be successful, you need to hire good people to work in it. By definition, ‘good’ people means they will, either from the start or eventually, be better at and more knowledgeable in what they do than you are. When that time comes, they may call you out on some of your plans and, in polite words, tell you that your idea is awful.

    The reflex is to become defensive and take the commentary personally, but don’t do that. You don’t have to accept everything they tell you, but to become a good leader you do need to listen to what they say and make sure you carefully consider it before making any decision.

    2) Become comfortable not doing things yourself.

    This one was very hard for me. As an engineer by training, I was used to my days being about what I, personally, was able to do and create. That is what made me feel like I had accomplished something.

    As a leader, it is not about you doing everything. In fact, the fewer things you do yourself, and the more you entrust to your team, the better leader you will be. You and your company will actually accomplish more.

    3) Make sure your team members know they come first.

    Let me clarify here. I don’t mean that a leader should make their team members feel like the boss at work. What I mean is that as a leader, you should make it clear that you put more importance in them as a person than the product or output of their work.

    If they are sick, or if they have a tragedy in the family, give them time off. This may require you, the leader, to pick up the slack. If they are behind on work due to no fault of their own — sometimes businesses get busy unexpectedly — try to figure out a way so they don’t have to spend every day for a month working 18 hours a day to get things done. Figure out a schedule in which they can go home and spend time with their friends and loved ones.

    Make your team members know they come first, and they will return it with long-term loyalty and great work.

    4) Don’t try to be their best friend.

    As a father, I constantly see parallels between fatherhood and being a leader at work. One of the key things I have learned in both scenarios is that you are not there to be their best friend. Your responsibility is to support your team members and make them feel appreciated. Your job is to help guide them to grow both as individuals and within their skill set. You should do what you can to help them reach their own personal goals, but also make sure they know the rules and don’t break them or get into trouble.

    As a leader, your job is not that they like everything you do all the time. It is not about going out for drinks with them every night. It is more about making sure they reach their own long-term goals and help your business along the way.

    5) Keep an eye out for leaders within.

    The final tip I wish I knew at the beginning was to look out for leaders within my team earlier on and nurturing them. When we are in a leadership position, we sometimes forget that we may not always be there, at least not in the same role we are now in. If we are in a larger company, we may be promoted or move to another department. If we are the owner of our own business, we may get to the point that we no longer want to run the day-to-day operations, or at least want help so we can pursue other projects.

    In both those cases, having another person who has been trained and is ready to take over for you is critical for not only your future plans but also for those of the company and the team moving forward.”

    Now that you have gained this experience and knowledge, has it affected or changed your personal leadership philosophy and style? How have these changes affected your company?

    Absolutely. The biggest transition for me over the last 13+ years of being a leader — in and in my other companies beforehand — was moving from the position of me having to do everything (or at least being involved in the nitty-gritty of each project) to trusting my team members to simply take my ideas and direction and execute them themselves.

    This was not an easy process, and I still backslide sometimes. However, figuring out how best to convey my ideas to my team members so that they not only understand the work that needed to be done, but also buy in to the vision of ‘why’ the work has to be done is something I have been working on for years, and still work on today.”

    This series is called “5 Things I Wish Someone Told Me”. This has the implicit assumption that had you known something, you might have acted differently. But from your current vantage point, do you feel that knowing alone would have been enough, or do you feel that ultimately you can only learn from experience? I think that learning from mistakes is the best way, perhaps the only way, to truly absorb and integrate abstract information. What do you think about this idea? Can you explain?

    As a lifelong martial artist, I am a strong believer in learning by doing. You can read all the Karate manuals and watch all the Kung Fu movies you like, but you are never going to get any better until you show up to a dojo and start practicing.

    Business is no different. You can read books and articles like this. While they will give you a high-level awareness of what can happen in the future, they really won’t sink in until you are in the right place in your development as a leader and the information is immediately relevant to you.

    It is not until you start applying things, and seeing what works for you as a leader, can you improve. The key here is ‘for you’. You may read something that sounds good in this article, or in a business book by one of the titans of your industry, but if what they recommend doing does not work with your personality, your team, or your leadership style, it is useless. The only way to find that out is to experience it.”

    You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

    Free co-working spaces for aspiring entrepreneurs in developing and 3rd world countries. There are many aspiring entrepreneurs around the world that have the potential to build a successful online business. I am not necessarily talking about the next Facebook or Amazon, as that is not a reasonable bar for most people. Successful in many parts of the world would be a business that brings in $500 — $1000 US of profit each month.

    This may not sound like a lot to somebody in a developed country, but in many parts of the world, including the Philippines where I was born, that would take you from poverty to middle-upper class. These free co-working spaces would operate a social enterprise, not a charity. They would offer workspaces, Internet access, computers, and even seminars and training to aspiring entrepreneurs, all free of charge.

    The way money would be brought in, so the co-working spaces can continue operating, would be that they would gain a share in each company started by people who work in the co-working space. If done right, this global network of free co-working spaces could own shares in hundreds if not thousands of micro online businesses, which then would allow them to continue to operate for free to help each subsequent generation start an online business and take themselves out of poverty.”

    How can our readers further follow your work online?

    You can find me at, at my new venture,, and at the below social media channels: