Dearest you.

Kriti Gupta calls herself an Internet Anthropologist — a translator of the signals young people are sending about who they are, what they value and what it’s like to be them.

In this honest conversation, we explore how Gen Z and Alpha are reclaiming their time, presence and self expression in an era defined by algorithms and increasingly, artificial intelligence.

Kriti helps us understand the subcultures and online worlds shaping identity, power and belonging for the next generation and what that means for brands, creators and leaders who want to connect meaningfully.

Kriti also opens up about her lived experience as a brown woman and creative trying to belong in rooms that value her ideas but not the face presenting them. Her reflections on reclamation, identity and creating her own tables are deeply moving.

Alison xo

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Dearest you.

This conversation with my friend, peer and fellow world-builder, Alex Taylor, has been 10 years in the making. We first met in our Who What Wear days — two young leaders shaping the same brand world from opposite sides of the world.

A decade later, Alex is the co-founder of Perelel Health, one of the most politically influential women’s health companies in the US with advocacy reaching all the way to the White House. 

This episode explores the parts of the founder journey that aren’t spoken about enough. The quiet questioning, the real costs, the faith required before investors and customers believe in what you're building.

Together we explore:

• How a brand earns the right to advocate
• Building community from scratch
• The tension between vision and viability
• Holding the mission before the market believes in you
• Navigating 100+ investor “no’s” while staying devoted to the work
• Feminine power, relational power and community power in leadership
• How our seasons as women shape the way we lead
• Why founders need boundaries, privacy and an inner life of their own
• The evolution of digital intimacy and brand world-building today

This is a conversation for founders, creators and builders who are quietly carrying the weight of their vision and looking for a reminder that they’re not alone. It’s also an invitation to rethink what modern leadership can be when it’s grounded in truth and generosity.

Alison xo

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Dearest you.

Are you sitting with a desire to become something or someone entirely new? To evolve your professional or personal expression in the most unlikely, bold way?

Maybe, like my guest Ruby Jean Cottle, you want to become a published author. Or maybe you’re an accountant who wants to become an artist. Or a leader who longs to be led again.

I hope this episode inspires you to take intentional action in the direction of who and what Nature is wanting you to become. I hope it affirms the quiet knowing that you’re ready to leap into the life you’ve been longing for.

Ruby and I trace her journey from multi-hyphenate creative and mother of two navigating “work” while living with endometriosis, to becoming a published author of Black River — a young adult fantasy novel she wrote before she ever had an agent or a book deal.

This is a conversation for anyone holding a creative dream inside them, wondering if they’ll ever feel ready.

Alison xo

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Dearest you.

If you’re an OG Offline Angel, you'll remember my first conversation about Human Design back in 2019 (listen here). Six years on and I'm feeling pulled back into this intricate knowledge system, this time through the lens of career and business building.

I'm thrilled to be joined by Human Design expert and portfolio career strategist, Julie Fedele, for an honest conversation about learning to trust and interpret the energetic signals already alive in our bodies — the ones we so often ignore.

Alison xo

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Dearest you.

What does it mean to become the condition for the world so many of us are longing for?

In this honest conversation, teacher, author, activist and US presidential candidate, Marianne Williamson, invites us to stop waiting for change and instead begin to live as progressive agents of love and right action in the here and now. Your personal awakening is what will fuel system and political change.

We also explore how activism can be rooted in compassion rather than contempt and how as female leaders, we can soften without surrendering our strength. She speaks candidly about the lessons, heartbreaks and growth that emerged from her presidential campaign which I'm really grateful for, offering rare insight into the courage and forgiveness that has been required.

Marianne is bringing her talk Inner Light, Outer Change to Australian in February. Get your ticket here.

Alison xo

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Dearest you.

In this honest conversation with Dr. Shefali Tsabary — clinical psychologist, author and global teacher of conscious parenting — we explore what it means to truly steward the next generation.

How can we start to see our children not as extensions of ourselves, but as spirits with their own unique signature? Dr. Shefali also shares her perspective on technology, cultural conditioning and how parents and leaders can return to wholeness so that our children feel safe to do the same.

This is a conversation about redefining success, resisting cultural lies and guiding our children to know who they really are. Surely this is the greatest inheritance.

Alison xo

• Buy tickets to see Dr. Shefali live in Sydney or Melbourne here

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Dearest you.

I have over 1,000 voice mentoring memos on my phone that I've recorded over the last handful of years for co-creators inside Offline spaces like serve. This is one of them.

A co-creator asked me what strategic documents she can have in place to hold her through the wobbles that come with being in business.

My response might surprise you. I share how to move beyond rigid strategies and into inner stability, how to practice daily contact with your Highest Vision and how to steward your business through financial ebbs and flows without abandoning yourself or the business itself.

The Highest Vision Worksheet I reference in this episode is here.

What you'll learn:

• Why clarity of vision and a mission for your money matters more than rigid strategy
• The daily energetic practices that make your Highest Vision feel inevitable
• How to use minimum viable, median and True Self Success salaries as responsive financial tools
• The importance of reserves, rhythms and quarterly reviews in building financial resilience
• How to hold yourself — and your business — through the dips without collapsing or constantly starting over

I hope this one helps you on your way.

Alison xo

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Dearest you.

Part two of my honest conversation with Del Rainbow co-founder, Bianca Gregg. Del Rainbow is the fashion sales agency supporting brands like St. Agni, Deiji Studios and Viktoria & Woods thoughtfully scale into new markets and here in part two, we move beyond tactics and into the heart of brand expansion.

What does it really take to grow globally and stay grounded?

Bianca shares her wisdom on how Australian fashion brands can break into international markets without losing the essence that made them special. We talk about the power of wholesale in 2025 and beyond, the energetic intelligence of global cities and the role brand founders play in stewarding not just scale, but resonance.

This episode is about more than just growth. It’s about belonging. About becoming the kind of founder who can hold more — more money, more visibility, more opportunity — without breaking alignment.

We hope this episode helps you on your way.

Alison xo

P.S. You can watch this episode on YouTube here.

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Dearest you.

Part one of my honest conversation with Del Rainbow co-founder, Bianca Gregg. Del Rainbow is the fashion sales agency supporting brands like St. Agni, Deiji Studios and Viktoria & Woods thoughtfully scale into new, global markets.  

In this episode — the first 45 minutes of our two-hour chat — we get into the experience 16 year-old Bianca had that taught her the true power of energy, connection and embodying our highest role: the conduit. 

In part two, we get into scaling strategy, her advice to Australian fashion founders who want to take their label global and the larger role wholesale plays within a fashion brand’s world building efforts. 

Alison xo

P.S. You can watch here :)

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Dearest you.

I have over 1,000 voice mentoring memos on my phone that I've recorded over the last handful of years for co-creators inside Offline spaces like serve. This is one of them.

A co-creator asked me how to receive more support at home now that she's working full-time, and when her partner earns more than her.

There's also some great insight into how to accept the season we're in, and how to let our manager know we need more support without coming across as incompetent.

I hope this 30-minute listen helps you on your way.

Alison xo

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Little, Rich Life Workbook

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Hosted on Acast. See acast.com/privacy for more information.