Building a Scalable Online Teaching Business with Jack Askew

Jack’s Spanish sojourn

When Jack Askew studied economics and marketing at university, he certainly wasn’t planning a teaching career. 

But he did have a hankering to try teaching in Spain — mainly because of a mate’s great stories. And when Jack’s wife got a teaching scholarship in Spain, he couldn’t wait to get started. 

Armed with a TEFL certificate, he taught English at a shipyard in Balboa for a year before shifting to a language school in Valencia. Then, while he was waiting for a visa to live in the USA, Jack started to think seriously about online teaching as a full-time gig. 

It didn’t take Jack long to get a full complement of students. 

Strategies for finding students 

Jack recommends thinking short term to find your first online language students. Short term strategies work fast to get your fledgeling language business off the ground.

They include:

• Classified ads on sites such as Craigslist
• Physical flyers 
• Advertising on Google and Facebook
• Referrals from past students and friends

These are all good ways to let students know about you and your language teaching. 

What exactly are you advertising?

Jack says that the best thing to advertise is a free lesson.

The all-important call to action

“The key is to have some kind of website landing page where people can easily take that action in order to take the initial step.” 

It isn’t hard to give away a free lesson. Here’s how you do it.

1. Use a scheduling service like Calendly, where people can reserve a time with you for a free trial lesson; if you don’t have a website, use a Calendly personalised link. 
2. Advertise that link with a call to action to book a free lesson.

Be sure that the free lesson gives your prospective student both confidence and value. 

When Jack gave trial lessons, he built up confidence by asking his student questions that they could easily answer. Then he introduced something a little more challenging and gave a mini-lesson on that. Finally, he asked what they would like to do next? 

If they booked and paid for lessons — fantastic. If not, Jack followed up with an email or two, to encourage that next step.

Getting your advertisements right

Two groups might see your language lesson ads. One is a cold audience – they have no idea who you are and are tentative when they click your link. 

The other audience has already warmed to you. They’ve seen your Facebook page or watched your videos and already have some idea of your style and what you offer. 

So, there’s a lot to get right for ads to work

• Know who you are targeting with the ad.
• Send out the right message, including the words, image and video.
• Have a Call To Action which leads to a landing page.
• Make it easy for people to book with you. 

You can also test various messages and videos to see which performs best. Some will appeal to your audience more than others. 

Jack says that retargeting ads work well too. These are advertisements aimed at people who have already watched your videos and know who you are. 

Long term strategies build a brand and an audience

While short-term strategies work to get your language business off the ground, you also need to think about the bigger picture. There is a limit to how many one-to-one lessons you can give in a day so that income is capped. 

It means that one day you’ll probably want to scale, and that’s where the long term strategy of building your brand pays off. Whether you’re running a website, a podcast or creating videos for Instagram, TikTok or YouTube, it takes time and lots of quality content to build an audience of people who like what you’re offering. And that’s the audience you need when you want to launch the next stage of your business.

Why Jack recommends starting on Instagram

“If you like putting yourself out there Instagram is a good place to go. The restrictions on Instagram make it easier to create.”

With YouTube, anything goes, and that can be overwhelming. It can take expensive equipment and time to create a stand-out video too. 

However, with Instagram, you’re restricted to a picture or a one minute video just using your phone. On top of that, you can use the Stories feature, which is a lot of fun and very interactive. Stories are a great way to build engagement.

Make sure that you put your Calendly URL into your profile as a link, or offer a different gift. Create content; build a following. And always make that call to action enticing and easy for people to follow.

The importance of making connections

“Connections are key with all of this. I grow the fastest when I’m connecting and collaborating.”

Jack has a simple way to create content and connections at the same time. 

Share other teachers’ posts in your stories.

Search, e.g. #learnenglish

If there’s a video or post that you like, click the share button and share to Stories. Mention that person in the story as well. A lot of the time, people will then share back as a way to say thank you.

Jack admits that having the two brands helps because it enables him to make even more connections. People tend to share content from both his channels. He doesn’t see this as a strategy, though. He’d prefer to view it as genuinely helping others in his community.

Can you really make a living from language teaching?

Yes, absolutely, says Jack. There are many ways to get paid as an online teacher.

1. Focus on YouTube monetisation and get paid through Adsense and sponsored videos.
2. Give one-to-one private lessons – be aware there’s a ceiling to this. You can only teach so many hours and charge so much. 
3. Specialise and help people with a particular need (e.g. passing exams)
4. Sell books.
5. Run a monthly subscription programme.
6. Promote affiliate links to sell other people’s courses. 
7. Make your own courses: there’s no ceiling to this, but you need a big following to make it work. That’s where your long term strategy of building an online brand pays off.

What’s one massive mistake language teachers often make?

Building a fancy website and forgetting the call to action.

“A lot of teachers will create a website which looks good and fancy; has all the information about lessons but it’s hard for the student to actually click a button and book something with the teacher.”

Jack can’t emphasise the importance of that CTA enough. It’s the button that will get the students in the door and on your email list. 

Jack’s tips for Langpreneurs 

• Identify short and long term goals. 

E.g. if you’re starting to teach one-to-one; a short term goal might be to get a full-time schedule in six months. 

“Now you’ve got a deadline so you’re not making excuses and putting things off. Then you can say what do I need to do to reach that goal?”

But your long term goal might be to create and sell online courses. You can start working towards those by building an email list and an Instagram following.

• Validate your online course before you produce it.

In 2014 Jack began to advertise his first online course. But he didn’t write the material until people started to sign up. The fact that people were willing to pay upfront gave him the confidence that he was on the right track. 

Then he made the slides for a six-week course which he taught live and recorded at the same time. That also gave him the material to improve and repeat at a later date.

• Stand out by being yourself.

“I think the best way is to be yourself and teach in the way you want to teach, because then you’re going to attract the type of learners who want to work with you.” 

Connect with Jack

To Fluency (website)

To Fluency (YouTube)

Teaching ESL online (website)

Teaching ESL online (homepage)

Jack on Instagram

Other links mentioned in this podcast

Camera Conspiracies

Vegetable Conspiracies