Full training
Notes from Rome
A room full of language teaching businesses, and what's actually
working right now
June 2026
Great two days with a room full of language teaching
creators and course businesses, a few of us from this
group among them. Expected a lot of hand-wringing
about AI. Got the opposite: people quietly proving that
the human side of this work is more valuable than ever.
Here are the ideas that stuck with me, in case they're
useful for yours.
THE BIG SHIFT
AI and the human moat
AI IS A TOOL, NOT THE THREAT EVERYONE FEARS
One creator reported revenue down 50% year on
year, with students self-teaching from AI instead of
buying. Real, and worth taking seriously.
But the consensus was clear: AI can copy information.
It can't copy trust, accountability, belonging or a real
person in the room. That's the moat, and it's getting
stronger, not weaker.
The businesses growing right now lean into the
human side rather than competing on volume of
content.
SELL BELONGING, NOT RESULTS
Giulia, an Italian teacher serving the Brazilian market
and one of the biggest creators in the room, said her
business turned the day she stopped selling "learn
the language" and started selling "we're in this
together."
Her line: today anyone can learn anything online, but
everyone wants to belong somewhere.
She frames it as a tribe, not a school. Everything
reinforces that, and it's what keeps people paying
year after year.
REVENUE & RETENTION
Where the money actually is
THE REPURCHASE WINDOW IS 60-70%, NOT COMPLETION
Teachable shared their own platform-wide data (Yas,
their Customer Success Lead): students who are 6070% through a course repurchase at 66-86%.
Students who complete? Only 19-27%.
At two-thirds through, they've proven your method
works for them and they trust you. That's the buying
moment.
If you're waiting for completion to offer the next thing,
you're offering it too late. Email at the 60-70% mark:
- "You're most of the way there, ready for your next
- step? Buy now, start later."
- MOST STUDENTS NEVER EVEN START
Also from Teachable's platform data: 88% of course
buyers have never opened a single lesson, and
around 30% never logged in at all.
Getting people to log in and finish lesson one is
upstream of any upsell.
A simple onboarding lesson (how the course works,
the schedule, what to expect) plus a "log in and start"
nudge moves the needle.
LIFETIME ACCESS: DON'T STRIP IT, TEST TIERS
Big debate on removing lifetime access to force
recurring revenue. The room's caution: older
audiences deeply value permanence, and you can
lose a whole segment by taking it away.
Better play: test tiers (6 months / 12 months / lifetimepremium) rather than removing the option.
Use expiry as a re-engagement moment. Peers
running automated expiry emails with a discounted
extension see 20-30% renew.
LIVE & COMMUNITY
Cohorts and belonging
A LIVE COHORT PLAYBOOK WORTH STEALING
Cap classes at ~12 so everyone actually speaks.
Cameras mandatory.
Set the rules with a short video students watch before
joining (camera on, be alone, take turns). Saves you
policing it live.
Use breakout rooms, polls and chat tasks to keep
everyone active.
Bundle: sell the course plus a few months of free
community, then convert to paid membership.
Win-back: when someone's about to cancel, a
feedback call that becomes a discounted lifetimeupgrade offer.
COMMUNITY MECHANICS THAT DO THE SELLING FOR YOU
More from Giulia's model. Gated subscription: you
can't just buy it. You have to attend the free classes
first, which qualifies and warms people before they
pay.
Gift the extras. Masterclasses, cook-alongs,
conversation groups given to members, never sold.
Scarcity and belonging do the converting.
A once-a-year premium/lifetime offer at an
anniversary event, open to everyone, converts
subscribers at an emotional high point.
TRUST & TOOLS
Building the relationship
THE 7-11-4 TRUST RULE
From Philip's talk on using Substack as a funnel:
- people need roughly 7 hours of your content, across
- 11 touchpoints, in 4 different places before they trust
- you enough to buy (he credited it to Google's
research).
It reframes your podcast / video / email / social stack
as one trust-building system that compounds, rather
than separate channels.
Check your own funnel against it: are you actually
giving people enough to get to buying-level trust?
TRAIN AI TO WRITE IN YOUR OWN VOICE
Stefano gave a brilliant talk on building a set of AI
"skills" that write his campaign emails in his real
voice, so he keeps his authentic tone without writing
every word from scratch.
Keys that made it work: feed it only your recent
finished campaigns (last ~18 months), not day-to-day
admin email; build separate small skills rather than
one giant prompt; add a "humanizer" pass that strips
the AI tells.
The point isn't to sound generic and fast. It's to
protect your voice while saving hours.
A DISCOVERABILITY CHANNEL FOR NEW AUDIENCES
Philip's whole talk was on this: Substack as a top-offunnel channel, not the revenue itself, but a way to
reach people who aren't already searching for you,
then funnel them to your courses. He's built it into
serious course sales from a standing start.
Every subscriber joins your email list (unlike a social
follower), and the audience skews intentional.
Note: it won't replace a proper blog for high-intent
search traffic. Its job is new-audience discovery, not
SEO.
The question I left with: is our existing audience
already on Substack, or are the people there a
genuinely new audience for us? That's the thing worth
knowing first, because the whole value is reaching
people who aren't already following us.
TEAM
Getting off the bottleneck
HIRING, IF YOU'RE THE BOTTLENECK
Hire for values and culture fit over raw skill, especially
for a small team built on a personal brand.
Learn the function yourself first so you can actually
judge the work.
Practical filters: state the salary upfront so people
self-select, and screen with a short form of real
scenario questions before any call.
Several creators hire from their own audience, people
who already love the brand.
The overall mood: this is a good moment to be a humanled teaching business, not a scary one. The
relationships, the trust and the craft are exactly the
assets that win now.