Cohort 1 · Starts November 1

Cuppa
Coffee & Conversation

Cuppa is full of incredible people. This is your invitation to get matched with 10 of them for an interesting coffee and conversation. ☕

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10 thoughtful matches for $100

200+ members, 24 good humans joined this month

The Neighbours

Who your next conversation could be with…

A sleep whisperer? A cyber hacker? A happiness expert? A survivor turned storyteller? A modern day elder? Only one way to find out.

Luke

Luke.

Sydney

Helping You Turn Pivotal Moments Into Powerful Movements

Fun facts about Luke

I’ve always believed the most powerful movements begin with a single, often messy, moment. From my early days in radio to launching businesses and leading teams, one truth has stayed constant: real change happens when people share stories, connect deeply, and take action — especially when it feels uncomfortable. I’m a cultural transformation expert, speaker, and founder of Cuppa.tv. My personal journey — marked by burnout, business loss, sudden grief, and reinvention — taught me that our most challenging moments can also be our most meaningful. Those moments shaped my purpose: helping others turn their own defining experiences into movements that matter. Today, I support individuals, teams, and organisations in navigating change, building culture, and embedding impact that goes beyond profit. My Moments to Movements framework turns pivotal life or leadership moments into personal growth, collective action, or even social good. With over 20 years in leadership, I create spaces where people move from passive observers to active explorers — because the world doesn’t shift through ideas alone. It shifts when someone chooses to show up, speak up, and step forward. If you're sitting in a moment and wondering what’s next — let’s explore where it might lead.

What Luke is working on now

Coming soon

Open to meet

Online / In person

Ashleigh

Ashleigh.

Brisbane

Grief-informed speaker & corporate advisor | Yellow Falcon founder

Fun facts about Ashleigh

Ashleigh was 29 and 17 weeks pregnant with triplets when her husband died suddenly in an accident. People were so kind - the flowers, the lasagnes, the messages. But none of them came with a roadmap for what actually came next. The estate. The financial collapse. The administrative nightmare. The months when her brain wasn't working but the decisions kept coming. So she built one. Counsellors handle the emotional weight. Funeral directors handle the day. Lawyers handle the estate. But no one walks you through the practical chronology of life after loss - and organisations don't have systems to support people through it. That's what Yellow Falcon is. In the organisations Ashleigh works with, one in four employees are grieving at any time. Most offer bereavement leave, then nothing. Support stops at the exact moment it's needed most - month three, month six, the anniversary. The cost appears later as absence, performance issues, or resignations, but it's never labelled as grief. A bereaved employee loses roughly 30 working days to absence and impaired focus in the year after a loss - which equates to roughly $21,000 in lost productivity per person. That doesn't factor in the employee's own financial crisis - loss of spouse's income, compounding superannuation gaps, bills unchanged. Psychosocial risk now sits within Work Health and Safety obligations, and grief is one of the most overlooked hazards organisations carry. Ashleigh helps organisations solve this with keynotes, training, workshops, and advisory to build manager capability, response protocols, and systems that ensure someone checks in when most have moved on. Not therapy. Not a wellbeing initiative. The practical framework organisations actually need, complementing existing EAP services.

What Ashleigh is working on now

Coming soon

Open to meet

Online / In person

Barry

Barry.

Sydney

Modern Day Elder, Mentor Story Teller

Fun facts about Barry

Many of you will know me as the co-host of the Logie award-winning lifestyle, TV show The Livingroom, alongside Amanda Keller, Miguel Maestre and Dr Chris Brown. We brought energy entertainment and fun to your living rooms—every Friday night on Channel Ten. My specialty in that role was design and renovation and for 13 years, I crafted and shared design theories and renovation processes to empower viewers. During that period of time, I also shared my own life experiences with Mental Health and Cancer. Using my media platform to empower others to bounce back from adversity. Embrace change and cultivate a positive mindset for personal transformation. A proud board member of RUOK day and Leukemia Foundation ambassador. I have become a sort after keynote speaker and coach specialising in Resilience, thriving after adversity and motivation. I proudly, and passionately use a lifetime of education, and experiences to make other people's journeys, the best they can be.

What Barry is working on now

Coming soon

Open to meet

Online / In person

Belinda

Belinda.

Sydney

Helping leaders harness flexible working to fuel performance and wellbeing

Fun facts about Belinda

Flexible work isn’t just a perk. It’s a secret weapon. I help leaders turn flexibility into a key driver of productivity, talent retention, inclusion and long-term business success. With a strong commercial foundation and real-world leadership experience, I deliver talks, workshops and coaching sessions that spark aha moments and lead to real results. Think of me as your guide to making flexibility work for your people, your customers and your business.

What Belinda is working on now

Coming soon

Open to meet

Online / In person

(*) Everyone here has said YES to 10 conversations. You could be one of them.

The Why

Why are people saying YES to 10? YES to 100?

The world is changing faster than any one of us can keep up with.

New tools. New industries. New ways of living, working, and making a living. And most of what's coming next won't show up in your feed. It will show up in conversations you weren't part of.

The people who keep up aren't the ones reading more. They're the ones talking to more people.

Don't get left behind. Compare notes over coffee. ☕️

Sign Me Up for 10 →

10 thoughtful matches for $100

The experience

How does it work?

A blueprint for keeping up with the world, one conversation at a time.

  1. 1

    Tell us what you are working on.

    Who you are, what you’ve lived, what you’re working on.

  2. 2

    Get matched with someone new.

    A glimpse of what they are working on and why we think you two should compare notes.

  3. 3

    Compare notes

    Thirty minutes on what they’re building. Thirty minutes on what you are building.

  4. 4

    Reflect

    Five minutes each to write down what you learned and what you will take with you.

  5. 5

    Make it a ritual.

    Ten people. Ten things you’d never have seen on your own. By the end, you’re not just keeping up. You’re ahead.

9:41●●●
Tell us about you
Q1What do you do, and why do you do it?
Q2What could you talk about for hours?
QUESTION 3 OF 11

What kinds of people would you genuinely love to meet?

Humans are more than a checklist. Pick as many as resonate.

Surprise meBuilder / entrepreneurTradespersonFarmer or food growerCreative / artistTherapist or counsellorTeacherCoachSomeone in healthcareDeep thinkerCurious humanQuiet observerBig dreamerIntrovertExtrovertCommunity builderAdventurerLifelong learnerSomeone new in town
+ 8 more questions
Next question
Your new matchCOFFEE #3
COMPLETE
Barry B., Sydney
Barry B.
SYDNEY
ONE-LINE STORY
Modern Day Elder, Mentor Story Teller
Schedule coffee
Betsy W. and Barry B. on a video call
OCT15
Thursday · 10:00–11:00 amYou both said yes.
Add to calendar
☕ CUPPA COFFEE & CONVERSATIONS2 members met.8 more coffees and conversations to go. Tap a face to meet them.
AnnieBryce
2 / 10
My journey to 10 conversationscuppa.com.au
Your reflectionCOFFEE #3 · BARRY B.
1  How was it?
😕😐🙂😊🤩
2  What did you talk about?
Second careersOld thingsSydneyFamily+ Add
3  What did you learn or notice?Twenty years in emergency rooms, and she still believes the best in strangers.
4  Do you want us to match you again in the future?
Yes, pleaseMaybeNot right now
5  How long into the future?
1 month3 months6 months12 months
Send reflection
In their own words

Meet the members. Hear what’s next.

What they’re building, exploring, and figuring out right now. A conversation about their next chapter—and yours.

  • World champions

    Layne Beachley won seven world surfing titles. Ask her what she’s chasing now.

    LayneLizzieLeighTomShannah
  • Founders who built brands you know

    Kristina Karlsson built kikki.K from an idea. Find out what she’s dreaming up next, and tell her yours.

    KristinaAshleighEranNicoleJoanna
  • People who’ve led from the boardroom

    Karen Stein spent 24 years as a Deloitte partner. Hear what she’s deciding now, and the very human questions behind it.

    KarenSandraLeaMichelleAaron
  • Minds shaping the AI era

    Yasmin London and Lee Foster help organisations navigate AI. Hear what they’re seeing right now, before everyone else does.

    YasminLeeBastienReannaMilo
  • Explorers with extraordinary stories

    Sarah Davis was the first woman to lead an expedition down the Nile. Ask her where she’s heading next.

    SarahAdamCamillaPaulLisa
  • Humans turning compassion into action

    Peter Baines founded a charity that has raised over $40 million. Hear what he’s building now, and what you could build too.

    RenukaJonAbangAnthonyNerissa

In the wild

What YES looks like.

Two people sharing what they’re working on, and both walking away with more: more ideas, more reach, more understanding, and someone new in their corner. In person or online.

Two speakers on a one-on-one online coffee call
Two speakers smiling over coffee at a cafe table
Two speakers on a one-on-one online coffee call
Two speakers laughing with takeaway coffees outside a cafe
Two speakers on a one-on-one online coffee call

Side effects may include: New ideas. Unexpected intros. Fresh eyes on your own work. Ten people who know what you’re building. Losing track of time. ☕️

Questions from the community

Frequently asked questions.

How many people know what you’re building right now?

In ten coffees, ten people will.

Your next opportunity can’t find you if no one knows what you’re building.

THE INVITATION, ONE LAST TIME ☕️

10 members. 10 coffees. 10 conversations.

Discover a side of the Cuppa community that only the members can reveal.

Sign Me Up for 10 10 thoughtful matches for $100