🔥 Early-bird $67 — ends April 30 at midnight PT. Price goes up to $97 on May 1.

⭐ Trusted by 10,000+ language learners worldwide
Powered by Teacher AI With Shayna · Greg · Anna

The 30-Day English

Speaking Challenge

The Good Old Days

Tell your childhood stories in English. One question a day, 30 days, with Shayna from Espresso English — joined by Greg (English with Greg) and Anna (English Like A Native) — and your own AI speaking partner available 24/7.

Shayna from Espresso English
Shayna
Your host
Anna from English Like A Native
Anna
British
Greg from English with Greg
Greg
British
Join the Challenge · $97

Starts May 1, 2026

30
Days of Speaking
4
Live Hangouts
24/7
AI Practice Partner
Sound Familiar?

You can read English. You can follow YouTube videos.
But speaking is still where you get stuck.

You've put in the hours. You've probably been following Shayna and other English teachers for years — you understand their videos, you can follow along, you've picked up a lot. But the moment someone asks you "How are you?" — you freeze. Your comprehension is miles ahead of your speaking. You don't have a grammar problem. You have a speaking problem. And the only fix is reps.

😰

You freeze before the sentence even starts.

The fear of sounding wrong keeps you silent.

🗓️

You have no one to practice with.

Native speakers talk fast. Tutors are expensive. Scheduling is a hassle.

🔁

You always start and then stop.

Motivation on Monday, gone by Thursday. No structure, no accountability, no follow-through.

📚

You keep studying instead of speaking.

Grammar books and vocab lists are fine — but they'll never make you fluent.

That's Why We Built This

Introducing the 30-Day English Speaking Challenge:
The Good Old Days.

Shayna from Espresso English
Shayna
Your host · Espresso English
Anna from English Like A Native
Anna
British · English Like A Native
Greg from English with Greg
Greg
British · English with Greg

Together with Shayna from Espresso English — joined by Greg from English with Greg and Anna from English Like A Native — we designed a challenge that solves the speaking problem directly. Every single day, for 30 days, you speak English out loud — telling your own stories.

This time, the topic is "The Good Old Days." One question every day about childhood memories, the places you loved, the people who shaped you, the smells and sounds you've never forgotten. And the best part? Shayna answers the question too — so every day you hear one of her own favourite stories from the old days, told in natural English, before you tell yours.

Most language learners separate studying from speaking by weeks or months. They wait until they feel "ready." That moment never comes. We fixed it with what we call the Same-Day Speaking Method: every day you get the question of the day, hear Shayna answer it, get a short breakdown with the key vocabulary — and then you jump into the Teacher AI app and have a real conversation with Shayna's AI clone around that topic. Speak as much as you want, for as long as you want.

Because this is a live cohort, Shayna shows up for you during the 30 days. You're not doing this alone. You have an experienced teacher, a supportive group of learners from around the world, and a clear structure that keeps you moving all the way to day 30.

📖

Learn

One English lesson every day, straight to your inbox, with short videos and breakdowns from Shayna.

🗣️

Speak

Practice that same lesson by speaking with Shayna's AI clone in the Teacher AI app.

🔒

Lock it in

Speaking activates vocabulary in a way that studying never can. 30 days and it sticks.

🤝

Stay consistent

A live teacher, a private WhatsApp group, and a streak tracker make sure you finish what you started.

What You'll Talk About

30 questions. 30 stories. Every day in May.

The theme is "The Good Old Days" — the memories, places and people that shaped you. Each day you get one simple question, a short lesson to give you the vocabulary and structures you need, and 10–15 minutes (or as long as you want) to have a real conversation about it with your AI speaking partner. The questions look simple on purpose — but you can speak as much as you want, at whatever level fits you today.

A few of the 30 questions you'll explore:

🏡 "What was the house you grew up in like? Can you describe it?"
🎬 "What's the first film you remember watching at the cinema?"
🎵 "What kind of music did you listen to as a teenager?"
🧑‍🏫 "Tell me about a teacher who had a big influence on you."
🍝 "Share a childhood memory related to food."
👃 "What's a smell that reminds you of your childhood?"
🇬🇧 "If you could visit any moment in Britain's past, what period would you choose?"
💌 "What advice would you give to your younger self?"

You don't have to prepare. You just have to show up and talk. And because these are stories you already carry — in your native language — you'll be surprised how much English actually comes out when the topic matters to you.

What's Included

Everything you need. Nothing you don't.

🎯

A New Question Every Day · Answered by All 3 Teachers

Every morning, a new conversation question about the good old days — answered by all three teachers. Shayna goes first in her clear US English. Then Greg shares his own answer in British English (with a Yorkshire accent). Then Anna answers in modern British English. Three real stories, three vocabulary breakdowns, both American and British English in the same lesson — all waiting on your personal course platform before it's your turn to speak.

🤖

Your Own AI Speaking Partner, 24/7

Practice speaking anytime with Shayna's AI clone — built around the exact challenge content. No judgment, unlimited attempts, your pace.

🎥

4 Live Hangouts with Shayna, Greg & Anna

Relaxed Google Meet sessions where you can talk directly to Shayna, Greg and Anna — ask your questions about learning English and practice speaking with real native teachers. Recordings available for 30 days.

💬

Daily Accountability WhatsApp Group

A private group with fellow learners from all over the world. Share your daily progress, ask for tips, and feel part of a real community.

📱

Full Teacher AI App Access

Complete access to the Teacher AI speaking app for the entire 30 days — the same app trusted by 10,000+ language learners worldwide.

📝

Lifetime Access to the Lesson Materials

Even after the challenge ends, you keep all 30 lesson videos to revisit anytime.

The Daily Routine

Here's exactly what each day looks like.

About 20 minutes a day. Do it on your lunch break, your commute, or hands-free while cooking. Three steps, every day, for 30 days.

1
📩

Receive today's question by email

Each morning a short email lands in your inbox with today's "Good Old Days" question and a link to your course portal.

📬 Daily email
2
📖

Study on your course platform

Open your personal course portal (hosted on Teachable) and watch the day's three video answers — Shayna's, Greg's and Anna's — each with their own vocabulary breakdown. Usually 5–8 minutes per video, in both American and British English.

🖥️ Course platform
3
🗣️

Speak with the AI clone

Open the Teacher AI app and have a real conversation around the day's topic with Shayna's AI clone. Speak as much as you want — anytime, anywhere, no pressure.

🤖 Teacher AI app

+ Join us in the WhatsApp group to share how it went — and read how everyone else answered the same question. Four times across the challenge, meet Shayna (and the other teachers) live on Google Meet.

Powered by Teacher AI

Seamless speaking practice, integrated with every lesson.

Unlike other apps that throw random topics at you, Teacher AI is completely aligned with what you're learning. Every speaking session is built around the challenge content — you practice exactly what Shayna teaches you, the same day you learn it.

🧠

Question-aligned AI conversations

Your AI partner knows today's question and today's lesson. They'll ask it, listen to your answer, and keep the conversation going — exactly around the story you're trying to tell.

✏️

Corrections that don't break the flow

Soft, in-conversation corrections that keep you talking — or detailed grammar explanations when you want to go deeper. You choose your style.

🎙️

Hands-free mode

Practice English while cooking, commuting or walking. Like a phone call with an English friend.

📊

Watch your fluency grow

Count every English word you speak. See your streak and vocabulary expand day by day across the 30 days.

🔗

Challenge content, fully built into the app

Shayna's AI clone lives inside Teacher AI — and for this challenge, all 30 questions and lessons have been built directly into the speaking exercises. Hear Shayna's answer, learn the vocab, then speak your own. Same topic, same day.

Inside the App

A look at the Teacher AI app.

Here's what your daily speaking practice actually looks like — the same app you'll be using every day of the challenge, built around Shayna's lessons.

Turn what you study into real speech

Every day's question appears right inside the app, so you practice saying it out loud — not just reading about it.

Real conversations, not drills

Your AI partner asks follow-up questions and keeps the conversation going — just like a real chat.

Natural corrections

Small mistakes get gently corrected in the flow — so you keep talking instead of freezing up.

Hands-free mode

Practice while walking, cooking or commuting. Just like a phone call with an English friend.

Your creator's AI clone

Shayna's voice and teaching style, available 24/7 — so you practice with the same teacher every day.

Lock in vocabulary with flashcards

Save new words from any conversation and drill them later with smart flashcards.

See your streak & leaderboard

Count every English word you speak, and see how you're doing against fellow learners in the cohort.

Note on the mockups: these screenshots show Spanish, Italian, Portuguese and French conversations — Teacher AI supports many languages. For The 30-Day English Speaking Challenge, of course, everything runs in English with Shayna's AI clone.

Your Coach

Meet Shayna from Espresso English.

Shayna from Espresso English
Shayna · Espresso English

Shayna is the voice behind Espresso English, one of the most practical English teaching channels on YouTube. Originally from Connecticut and now based in Salvador, Brazil, she has been teaching English for over 10 years — first in classrooms, then online. Her CELTA-certified, bite-sized teaching style is built on a simple promise: clear lessons that fit into a few minutes a day — perfect for learners who want results without overwhelm.

For this challenge, we've created an AI version of Shayna — her image and voice, right inside the Teacher AI app. Every question of the day is waiting for you there, so you can practice speaking out loud with Shayna's AI clone as often as you like, 24/7, until it sticks.

And it's not just Shayna. When you join through this page, you also get the daily video answers from Greg (English with Greg) and Anna (English Like A Native) for every single question — so you hear the same story told three times, in two flavours of native English: American (Shayna) and British (Greg & Anna). Three teachers, one price.

745K+
YouTube subscribers on Espresso English
Mark Your Calendar

4 Live Hangouts with Shayna, Greg & Anna

These aren't webinars. They're relaxed Google Meet hangouts where you can talk directly to Shayna, Greg and Anna — ask your questions about learning English and practice speaking live with real native teachers. Can't make it live? Recordings are available for 30 days.

Shayna
Shayna
Espresso English
Greg
Greg
English with Greg
Anna
Anna
English Like A Native
Session 01

Group Kickoff · all 3 teachers

Tuesday, May 5

9am NYC · 2pm London · 3pm Madrid

Session 02

Hangout with Anna

Tuesday, May 12

9am NYC · 2pm London · 3pm Madrid

Session 03

Hangout with Greg

Tuesday, May 19

9am NYC · 2pm London · 3pm Madrid

Session 04

Hangout with Shayna

Tuesday, May 26

9am NYC · 2pm London · 3pm Madrid

All four hangouts run at 9am NYC time (2pm UK / 3pm Spain). Can't make it live? Every session is recorded and available for 30 days.

Enrollment

Join the Challenge

$ 97
$97Save $30 with early-bird pricing 🔥 Early-bird ends April 30 · Price goes up to $97 on May 1

One-time payment · No subscription · Challenge starts May 1, 2026

  • 30 daily questions + lessons delivered by email — with 3 video answers per question from Shayna, Greg & Anna (American & British English)
  • Personal course platform with all study materials
  • Full access to Teacher AI app for the 30 days — no separate subscription needed
  • Unlimited speaking practice with Shayna's AI clone
  • 4 live Google Meet hangouts with Shayna, Greg & Anna
  • 30-day replay access to all live sessions
  • Private Daily Accountability WhatsApp group
  • Lifetime access to your 30 questions + lesson materials

About the payment: Your $97 covers everything — including full access to the Teacher AI app for 30 days. There is no separate subscription to start, no free trial to cancel, nothing to unsubscribe from afterwards.

Already a Teacher AI subscriber? Your subscription is paused for the 30 days. You pay $0 extra and resume your regular plan on day 31.

🛡️ Our guarantee: Not speaking more English by day 15? Email us for a full refund. No questions asked.
Yes, I want to speak English →

🔥 Cohort starts May 1, 2026 — spots are limited

Results

Participants activated thousands of words in 30 days.

Across past learners in our Teacher AI speaking challenges, 200+ students from 25 countries spoke their target language out loud every single day — most for the first time in years.

Leaderboard from day 23 of a previous cohort showing seven learners with 4,000–8,700 English words activated
Real leaderboard from day 23 of a past Teacher AI speaking cohort. Every learner you see here had already activated thousands of words in their target language — the top student at 8,710.
★★★★★
"I was impressed. The AI actually understands what I'm saying, and corrects my mistakes accurately. I feel reassured."
François · France
★★★★★
"I was surprised how natural the voices sound. I love that they repeat my sentences back to me correctly. It's fun, and I think by the end of the month I'll be speaking more fluently."
Stefanie · Germany
★★★★★
"A native speaker friend tried it and said the AI's accent is really natural."
Tom
★★★★★
"Day 2 of the challenge and I already feel at ease. It's so much fun — this challenge is worth it."
María Luisa · Mexico
★★★★★
"Thank you for this amazing idea. I've been using Teacher AI for almost a year, and the challenge gave me back the desire to practice every day."
Lelie · existing Teacher AI subscriber
★★★★★
"Thank you for this first challenge. Despite the mistakes and the fear of going for it, I've learned so many words and grammatical structures."
Naima
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FAQ

Common questions

The challenge is built for learners at roughly A2–B1 level or higher — you should be comfortable reading simple English and following basic conversation. If you're a complete beginner, we recommend waiting for our beginner track (launching July 2026).

No. Your $97 includes full access to the Teacher AI app for the 30 days — no recurring charges, no free trial to cancel, nothing to unsubscribe from. If you're already a Teacher AI subscriber, your plan is paused during the challenge and resumes automatically on day 31.

Shayna recorded hours of voice and lesson content. We used that to build an AI clone of her inside the Teacher AI app — you can speak to her like you would on a phone call. The clone knows exactly what lesson you're on and will practice that material with you, give feedback, and keep the conversation going.

Both — and that's by design. When you join through this page, every daily question is answered by all three teachers: Shayna from Espresso English (US English), Greg from English with Greg (Yorkshire-rooted British English) and Anna from English Like A Native (modern British English). So each lesson exposes you to two flavours of native English in the same topic — most learners benefit from understanding both, even if they prefer to speak one. Your speaking practice in the app is with Shayna's AI clone, so your daily conversations stay in her US English.

The theme is "The Good Old Days" — 30 questions about childhood memories, the places and people who shaped you, and your relationship with the past. Everything from "What was your dream job as a child?" to "What's a smell that reminds you of your childhood?" to "If you could visit any moment in Britain's past, what would you choose?" Each question looks simple, but you can answer at any level — a few sentences or a long story, whatever fits where you are today. All three teachers — Shayna, Greg and Anna — answer every question themselves, so each day you hear three real stories in natural English (American and British) before it's your turn.

Every morning, an email lands in your inbox with the day's question and a link to the lesson on your personal course portal (Teachable). Inside the portal you'll find three video answers — one each from Shayna, Greg and Anna — each with their own vocabulary breakdown, plus written materials. Then you open the Teacher AI app and have a real conversation around that topic with Shayna's AI clone — speak as much or as little as you want, for as long as you want.

All four hangouts are recorded and available for 30 days. You can watch them back anytime.

About 20 minutes: roughly 5–8 minutes of video, then 10–15 minutes of speaking practice. You can do it on a lunch break, commute or walk.

A smartphone works best (Teacher AI has iOS and Android apps). You can also use the web version on a laptop. If you can use WhatsApp and a smartphone, you can do this — we'll help you get set up on day 1.

Yes. The Teacher AI app has a History tab where you can scroll through every conversation you've had with Shayna's AI clone — read the transcript, listen back, and see the corrections you received. Downloading transcripts isn't supported right now.

Yes. If by day 15 you don't feel you're speaking more English, email us and we'll refund you — no questions asked.

You keep lifetime access to the 30 questions, daily lessons, and videos. The Teacher AI app subscription continues only if you explicitly choose to subscribe — we'll send alumni a special offer around day 28.

In 30 days

you could be

speaking English with ease.

All you need is 30 days, one question a day, and Shayna cheering you on. You can do this.

Join the Challenge · $97

Starts May 1, 2026

🛡️ 15-day money-back guarantee · One-time payment · No subscription