growing a teaching business and a family - jennifer-2

Growing a Teaching Business and a Family: Interview with Jennifer from English Outside the Box

I’ve got a great interview for you today.

Jennifer (English Outside the Box) and I discuss growing a teaching business while also growing a family, how to go from one-to-one lessons to online courses, and her tips for those getting started.

We get into the different platforms that you can use to host your courses, favorite social media platforms, the biggest frustration in the early days and much more.



Jennifer moved to Brazil with her husband and that’s when she started teaching English.

After three years of teaching in language schools, she wanted to have more independence. One night, started on a teaching platform before creating a website and profiles on Facebook and Instagram.

The biggest frustration at the beginning was managing student expectations and finding the balance between helping learners for free and creating an income.

Jennifer found students through Facebook in the beginning. She started with an old student who she used to teach and got many referrals from this initial student.

When I asked about her favorite social media platform, you’ll notice that this has changed. At first, it was Facebook, then Instagram, and she is currently coming up with a new strategy.

We then talked about YouTube and why she stopped giving a live lesson at the same time every week. She has seen growth since stopping this.


Jennifer started by putting her online courses on Udemy, then on to her own site, before going with Teachable.

Here is a break down of these platforms:

Udemy (affiliate link):

  • they host and sell your online course
  • marketplace for students
  • less control over your customer information and pricing

Selz (affiliate link)

  • digital product payments and delivery
  • no marketplace for students (market your own courses)
  • no online course templates

Teachable (affiliate link)

  • best all-in-one solution
  • not as much control than hosting it on your site

Own Website

  • most control
  • can be difficult to set up

Jennifer spent her evenings and weekends creating her first courses; like a side hustle.


Jennifer thought about maternity leave in advance.

She collaborated with other teachers so she had content to post for the first few weeks after giving birth.

She also decided to work asynchronously with her learners where she gave them feedback on their speaking and writing.

Routines are constantly changing. She worked while her son was napping. Boundaries are important.

She wants to improve the courses she has now and start doing live events.

Learn more about her company here.



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Beyond One-to-One Lessons: An Interview with Teacher Vanessa (Watch This!)

Vanessa Joy has built a very successful online teaching business.

She teaches one-to-one and, recently, she opened a new subscription program.

In this interview, she shares how she managed to have all this success in such a short amount of time. You’re going to love this.

Thanks for watching.

Interview Takeaways

Making Mistakes

Teaching English online there for those who commit to it. Yes, you’re going to make mistakes at first. Who doesn’t?

The key is to take action and learn as you go.

Vanessa also talked about the importance of taking courses (she is a TEOC member, after all!) and learning what you need to do to get this right.

Safe Environment

Vanessa’s goal is to give her learners a safe environment. A bad comment on one of her videos isn’t the end of the world and she’s surprised by the lack of nasty, YouTube style, comments.

She’s also a serial banner!

Getting Students and a Clear Marketing Strategy

Vanessa uses email marketing to fill her schedule and sell her courses.

In summary, this is how it works:

  • Give something away for free
  • Create content and send learners from your content to your free download
  • Create automated emails that build trust and sell your lessons

Click here to learn more about how to do this.

Subscription Program

Vanessa has gone all in and created a monthly course for learners.

Doing something like this is a big commitment. Vanessa was prepared for this and is creating the type of materials that she was creating for free anyway. As you can tell, she’s on top of it all.

Resources Mentioned

Over to You

Has this interview inspired you? What have you learned?

Let us know in the comment section below!


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Olly Richards Interview

Olly Richards on Monetizing his Blog and Language Learning & Teaching

Olly Richards InterviewYou’re going to love this one…

Olly and I first connected a couple of years ago. I love his writing style and his story, so I had been trying to get him do a guest post for a while.

Instead, we went all in and did an hour-long interview. We discussed how he got started learning languages, how he grew his blog and monetizes it, his podcast, and his approach to teaching languages.

We recorded this interview live on YouTube. It was a lot fun doing this – and I enjoyed asking Olly questions from those who joined us live.

If you want to skip to specific sections, you can do so by reading the notes below. But I think this will be an hour of your time well spent.

Here is the interview:

Subscribe to my channel here. And then, read on below to read a summary of our conversation.

Learning Languages

Olly learned languages at school, but it wasn’t until he started working in a local cafe that he got the bug. He wanted to be able to speak to his workmates in their native languages.

He started using self-study books but didn’t have any idea of what it actually took. Like he said, you don’t know what to expect if you haven’t done it before.

Creating his Blog and Podcast

Olly started his blog in 2013. This is where he helps others learn languages. At this point, he didn’t know what an online business looked like. He committed to writing one post per week and saw steady growth. Like he said, if you start writing and commit to it, you will get better.

He wrote guest posts for other blogs to help him grow his audience. And he gets ideas for his posts from forums and from his audience.

One year ago, Olly started his podcast. He kept it simple as he knew he wouldn’t be able to sustain a complicated format. Check out his podcast here.

Creating Videos

We broke down two ways of creating videos:

  1. Super-produced
  2. Raw

There is, obviously, some middle ground here. But I think it’s good to think about what you want to get out of making videos and how you are going to do this over the long-term.

(Jack’s note: here is a post I wrote on making videos – I include the equipment you’ll need)

How He Does All of This

I asked Olly how is he was able to build a popular blog, learn languages, and work a full-time job at the same time. His quick answer? Hard work. He went on to elaborate saying that he worked evenings, weekends, and over his lunch-breaks, and that everything was sequential.

(Jack’s note: To learn more about how to build a teaching business on the side, check out my post here.)

Monetizing and Selling Products

We then moved on to how he monetizes his blog. Olly has multiple income streams: online courses, books, audiobooks, other products, sponsors and affiliate marketing.

His advice here is simple: know what problems your audience have and solve them.

We then went on to talk about free vs paid. As Olly said, if you invest in a course, you are investing in yourself. I added that there are three types of people:

  1. Those who never pay for anything
  2. Those who are on the fence
  3. Those who are ready to buy what you offer

Don’t worry about the first group – you’re not going to change their mind easily. Focus on helping those in group two and three instead.

(Jack’s note: if you want to build a successful online teaching business, check out my course and community here.)

How to Teach for Fluency

Finally, I asked Olly about how he incorporates his knowledge and experience of second language acquisition into language lessons.

He started off by saying that traditional classroom lessons are an unnatural construct. Students see you (the teacher) as the solution. But language isn’t imparted, it’s learned. With this in mind, we need to think about how best to spend out time with the learner. We can teach the language, strategize with our learners, or spend time using the language in class.

This is what we need to work out as teachers and work through with our learners. A lot depends on what the learner is willing to do outside of the lesson. There is no easy answer here.

Over to You

We covered a LOT of ground. A common theme, if you want to build your teaching brand online, is to get started and stay consistent.

What did you think about the interview? Do you agree with Olly that we need to be learning a language ourselves to become better teachers? How do you help your learners outside of the classroom?

What other thoughts do you have on starting a blog, monetizing etc.?

I would LOVE to hear your thoughts. Please leave a comment below!

And check out Olly’s blog here.


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James Taylor Interview

James Taylor Interview: Blogging, Twitter, English Teaching Methods, Non-Native Teachers and More!

James Taylor is one of the busiest English teachers I know.

He has a lot going on and he is heavily involved in ELT, both online and off. We get into a lot during this interview, including:

  • how he got into teaching
  • why he started a blog
  • Twitter and #eltchat
  • his podcast
  • TEFL Equity Advocates
  • teaching methods

What We Discussed

James fell into language teaching out of circumstance (I did too), but fell in love with it. He’s moved around a lot and now works for Cultura Inglesa.


James started blogging five years ago. He had already read other blogs and had things he wanted to say. Here is his blog.

Twitter and ELT Chat

James joined Twitter over six years. He is a moderator for #eltchat. This is a Twitter-based discussion where English language teachers discuss different topics.

Each chat has a transcript and summary.


James also has a podcast called The TEFL Commute Podcast. As James put it, it’s a podcast fo English language teachers that isn’t about language teaching.


When James moved to Belgium, he noticed that there wasn’t a teaching association in the country.

After discussing this with colleagues, they decided to set one up in 2013. Being the President has taught James a lot about teaching and helped him pick up new skills.

TEFL Equity Advocates

James has also worked with TEFL Equity Advocates. Part of his work was to write a post called Why I Wish I Was a Non-Native English Teacher.

This has gained a lot of attention (and is a great example of a headline getting interest).

Teaching Methods

James’s teaching style changed after taking his CELTA in South Korea. This is where he “made the transition from someone who taught English to becoming an English teacher.”

He then discovered Teaching Unplugged. This is a method that is light on materials and conversation driven. He has also recently been influenced by Philip Kerr.

Finding the Time

Finally, I asked James how he found the time to do all this. He talked about how it’s his hobby and that he feels it’s his responsibility as a teacher.

About James

You can find out more about James by visiting his blog and can connect with him on Twitter and Facebook.


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Interview Shayna

Shayna Oliveira Shares Her Story of How She Built Espresso English in Her Spare Time

One of the biggest challenges for teachers moving online is finding the time to get things moving.

Shayna, from Espresso English, shares how she built an online business while working in other positions in this latest interview.

In addition to sharing how she made the transition into going full-time with her business, I ask Shayna about how she built her brand into one of the most popular sites for English learners, what products she sells, how she markets her courses, and her plans for the future.

Watch in HD!

What We Discussed

Shayna started her website after one of her learners asked if she could send daily lessons by email. She soon realized that she could reach a lot more people this way and published the lessons on her new website.

The first stage of her online business lasted around 6 months. She posted consistently (nearly every day) taking inspiration from her offline classes. She then launched her first ebook “100 Common Errors in English”, and the feedback and sales from this encouraged her to keep moving forward.

While Shayna was building her brand, she was teaching in her local area and working 10+ hours per week for a web development client in the U.S. She waited for the right time to go full-time with her business, and her offline teaching was the first to go. After “chickening out” once, she quit her other job in 2014.

As of today, Espresso English offers 3 books, 9 online courses, and a monthly subscription program. There are 40,000 learners subscribed to her email newsletter and her site brings in 300,000 visitors a month.

Shayna puts her growth down to consistently giving away free content. In addition to her blog, she also posts videos on YouTube and has a popular podcast.

Shayna has used an email newsletter right from the start. In every email, she links to a relevant product. Her motto is, “Always present, never pushy.”

Shayna plans to go back and improve the courses she currently has. This will be based on the feedback she receives from those inside her courses.

Over to You

I really enjoyed interviewing Shayna and I have learned a lot from her during out mastermind meetings.

Her transition into online teaching is a perfect example of someone building something on the side and going full-time when the time is right. Additionally, the way she has consistently posted free content shows just how far you can take things if you stick at it.

I hope you enjoyed the interview. Please leave any comments or questions you have below!

You can connect with Shayna through the contact form on the Espresso English website.


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Interview Jase

Jason R. Levine: Teaching English through Music, Travelling, and Helping Learners Do More in English

Jason R. Levine is an English teacher who travels the world performing songs he has written specifically for English learners.

In the interview, we talk about how he got started with making music, why he was nervous about putting his songs out there, what he likes most about doing workshops around the world, and how he uses social media to connect with and inspire English learners worldwide.

Watch in HD!

What We Discussed

After getting a masters in TESOL, Jase started teaching English in New York.

He started using music in the classroom right from the start to give learners more exposure to the language in a way that was fun and sustainable.

His first song, StickStuckStuck, has nearly three million views on YouTube. He talked about how he was a little nervous about putting this out there at first, but his learners persuaded him to do it. He didn’t have a plan for where he wanted things to go, but this song was the catalyst for his current success.

His first tour came about after a teacher in Morocco shared his video on Facebook. She pulled some strings and he headed over there to perform.

At this time, he also realized how powerful social media could be. He started using it as a way to get feedback from learners and teachers. We talked about how different online platforms have allowed him to expand his reach and help him inspire learners to do more in English.

It addition to the touring (Gallery Languages help with this), Jase has started creatings courses for learners and teachers. Here is a mini-course that he is going to teach in late June/early July.

Over to You

It is obvious from the interview that Jason is passionate about reaching English learners on a large scale. His work with teachers is incredibly inspiring too.

If you follow Jase on social media, you’ll realize that he enjoys sharing, commenting, collaborating, and working with other teachers. He is incredibly active and his success online is down to the work he puts in.

I would love to hear what you think about this interview, so please leave any comments you have below!

Follow Jason on Facebook here.


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Interview Andrea

Andrea Giordano on Teaching Online and Selling Products

Joining Teaching ESL Online in this latest interview is Andrea Giordano from ESL Basics.

Andrea and I recently collaborated on a video together and, after looking at her website and YouTube channel, I reached out to ask if she would like to share her online teaching story with us.

In the interview, we discuss how she got started, email marketing and social media, and her courses for English learners.

Watch in HD!

What We Discussed

Andrea started teaching English in 2006 while she was in the process of getting her TESOL. But after binge watching Food Network Star, she thought, “I can do this.” So, after bouncing ideas around with her brother, she decided to start teaching English through video.

She shot several hundred videos on her YouTube channel in the first couple of years and has continued uploading free content since then. Her biggest challenge in the beginning was working out who her audience was and how she was going to connect with them.

Most of her early videos were around 15-20 seconds long. As she became more comfortable and built up her experience teaching in the classroom, she started to make longer-form videos.

She regrets not starting an email list straight away but, when they did, it was a game-changer, and this is when they started to see their audience grow.

They have had ups and downs with YouTube – having your advertising cut off is never nice! – but it has helped them cast a wide net and bring more learners into their world.

Andrea interacts with learners through her various channels. She talked about how she reaches out to people through Twitter, not to sell them her courses, but to get the conversation going. As she mentioned, she really cares about helping learners improve their English.

They use Selz as their payment provider for their products. We both talked about how easy it is to set up and use, and Andrea mentioned how impressed she was with their customer service.

They have had much success with helping learners who need to take the Citizenship Test in the U.S. and have various products and videos in this area.

A new course (The Spoken Life) is going to be introduced soon (by the time you read this, it will most likely be live) and it is there to help English learners become more confident with their speaking.

You can reach out to Andrea by email or by contacting her through Twitter.

Over to You

I hope you enjoyed listening to Andrea’s story. Unfortunately, I messed up the recording of the video a little but we got to see her at the end!

One of the biggest takeaways for me was the amount of time she spends interacting with people online. Doing this shows that you care and helps you build trust with English learners.

Please let me know your thoughts on the interview in the comment section below!


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Interview Justin Murray

Justin Murray on Connecting English Learners, Building an Audience, and Solving Problems

What would you do if Facebook deleted your group with over 120,000 English learners?

That happened to Real Life English (RLE), and one of the co-founders, Justin, joins Teaching ESL Online to share this story, and to give us an insight into how the RLE team built a very popular site for English learners.

Watch in HD!

What We Discussed

Justin started by introducing Real Life English as follows:

“It’s a global community of English learners and speakers dedicated to help people all around the world speak English through real life conversations, real people, and real learning materials.”

RLE got started with a party in Belo Horizonte, Brazil. Justin, and his cofounder Chad, wanted to teach English in a way that would help people to live it. And after they saw how popular the parties were, they decided to start a blog.

For nearly two years now, they have been posting content (videos, podcasts, articles etc.) 4-5 times a week. One of their former cofounders started a podcast and a Twitter account. And talking about the podcast, Justin said:

“If you keep doing something over and over again, you get better.”

We then talked about the Facebook group that they built to over 120,000 members. But out of nowhere, their group was deleted.

“If you build your house on Facebook, they can always take it away from you.

This is why it’s so important to build your own blog/website and email list.

We then talked mored about Facebook, specifically organic reach (how many of your followers see your content when you post). Justin then went through the difference between a Facebook page (business page) and a Facebook group.

Justin’s former cofounder started their Twitter account and employed different tactics to grow their following (currently at 70k), using tools such as Tweepi. They also use Hootsuite to schedule their tweets.

They have a free ebook for learners and this has helped them grow their following. Focusing on email marketing has been a big part of their strategy from the start.

Justin and the team spend most of their time interacting with learners through email, and prioritize this over social media.

We moved on to talk about the different products they have sold. They have offered an audio version of the ebook mentioned before, a course called Fluency Plus, and a product that goes with their podcast. I’ve seen one of the podcast lessons, and it’s incredible how detailed and in-depth they are.

The RLE team are now in Chile in a startup incubator. They are shifting their mindset to try and understand what learners really need, and to build a business around this. And the problem that they are trying to solve is to help learners connect with others and use their English in a way that feels real.

You can learn more about Justin and Real Life English here.

Over to You

What was your biggest takeaway from this interview?

Leave your comments below!


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Interview Gabby Wallace

Gabby Wallace on Teaching Online, Youtube, Podcasts, and Online Courses

In this latest interview, I speak to Gabby Wallace about teaching online.

Gabby has a very successful YouTube channel, co-founded a popular podcast, and has created various online courses for her English learners.

We discuss the above and much more in our interview below. Hope you enjoy it:

What We Discussed

We started off talking about our mastermind group. Now, a mastermind group is where you meet either online or in-person to brainstorm, share your successes and failures, give advice, share resources, and give each other support.

“For me, it’s been really motivating and it’s held me accountable too.”

Like Gabby said, it’s about collaboration, not competition, and we both recommend finding people who have something in common with you if you want to start your own mastermind group.

Gabby has been teaching language for over ten years in many different settings and age groups. About five years ago, she picked up a copy of The Four Hour Work Week, read other entrepreneurial books, and liked the idea of moving online and helping more people.

But before all that, she started making short videos that answered the questions she had in the classroom, and uploaded the videos to YouTube.

There was no business plan at this point, but she started receiving positive feedback, and made more videos. YouTube has now become a focus for her online teaching business (driving people to her website and to continue learning with her).

She was a little self-conscious and worried about putting herself out there at first, but it’s something she has got used to.

Gabby has also had a lot of experience with podcasting and has been very successful in this area. She was the co-founder of All Ears English. It was, and still is, hugely popular. But after a year or so, Gabby started her own podcast and concentrated all her efforts on her own brand.

Before starting the first podcast, Gabby admitted that she had never listened to one before. There were a lot of things that she had to figure out to get things going, but once she had gone through this process once, she knew exactly what to do the second time.

After creating around 100 videos on her YouTube platform, she posted her first course on Udemy. This year, she posted a new course on her own site, which is solely video based. She has a total of six courses with a new one on the way.

Just like Stephen, Gabby listens to her learners and creates her courses based on the feedback she gets.

In the past, Gabby couldn’t get things to work on her own platform, but changing the software she used made a big difference. When creating her courses, Gabby sets a deadline, pre-sells the course, and then gets the material out there.

Gabby’s plans for the future are to continue working on Go Natural English, and also wants to help online teachers become successful online through her blog, Laptop Language Teacher.

Here are some links to her social platforms:

YouTube for GNE
YouTube for LLT
– Her Facebook page

Thanks Gabby for sharing your story with us!

Over to You

Did you enjoy the interview?

Please comment/ask questions on anything we discussed. Gabby and I will respond to any questions you have.


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Interview Stephen Mayeaux

Hip Hop, Making Connections, and Online Courses: An Interview With Stephen Mayeaux

In this post, I interview my friend Stephen Mayeaux over at

Stephen started his blog after his experience teaching an elective course at UC Davis.

His main focus at the university was academic preparation, but in his elective, he was free to do something different. This is when he started using hip hop in the classroom.

In this interview, we go deep with his use of hip hop with his English learners, the feedback he has received on this, how he got started online, and then, we learn about a new course he is creating for a specific niche.

Watch in HD!

Interview Notes and Resources

We start off with how we connected, and briefly talked about the importance of making connections when working online.

I love how he talks about the struggles he had when he first started using hip hop in the classroom. This was mainly due to the cultural differences, and he gave the example about his Japanese students not understanding the social issues of the police in the U.S.

He had his friend help him create his site using WordPress (he is now quite adept with coding). The feedback he received from the lessons he created was really positive, both from teachers and students.

He blasted 100 lessons out in the first year, but has slowed down his output since to about one lesson per month.

Using Hip Hop in English Lessons

If you want to use hip hop in the class, he recommends going back in time to the old school era, for example, The Beastie Boys and MC Hammer. Additionally, he recommends using the hook and the chorus of modern hip hop.

I really wanted to know about the response Stephen has had about using hip hop in the classroom. I love his answer to this: he is focusing on his students and what they can get out of it, and that, haters gonna hate! But generally speaking, he hasn’t received much negativity.

A Course for a Specific Niche

We then moved on to what Stephen is currently doing; he is in Korea at right now working for a local school – we talked about how they are trying to introduce new teaching methods there.

He has a new video course coming out in March in a very specialized niche: OPIC. It’s not a very well known exam, but after seeing that his students were asking for more help in this area, he decided to create something for them.

He is completely engrossed in this process, and is learning new things each day about what creating a course entails. Stephen said something key about how he is creating the materials for his course:

“…Listening to my students, their concerns, and what they really want.”

He is creating the content for his course based on what his learners are asking for.

We then talked about deadlines and the power of setting a specific deadline (his deadline is March 14/15th – he wants you to hold him to this!).

He has hired a freelance marketer to help him with the marketing side of things. I then talked about outsourcing, and specifically, the two types of tasks to outsource: tasks that you are not skilled at and don’t want to learn; and also the mundane and repetitive tasks.

In my case, outsourcing the transcripts for my course helped me in a great way.

We then moved on to social media, and how he uses Facebook and LinkedIn. We focused on using these platforms to make and maintain connections. An example he gave was connecting with Gallery Languages and how they have partnered on many projects.

Here is an example of one of the video’s he mentioned:

Over to You

Have you used hip hop or other music genres in your lessons? Have you thought about creating a course for English learners?

Answer these questions and/or leave any other comments below…

You can connect with Stephen by using the contact form over at You can also connect with him on TwitterFacebook, and LinkedIn.


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