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Helping you find your perfect style online!
What if shopping online actually understood you — your wardrobe, your taste, your real-life style — instead of throwing endless trends and products your way?
That’s exactly the problem Kathleen Sheppard set out to solve with Tote, a personalised fashion-tech platform designed to help people cut through the noise and rediscover their own style.
Tote flips the traditional shopping model on its head. Instead of starting with products, it starts with you. Users log their outfits, build a picture of their real wardrobe, and receive tailored recommendations from an AI stylist — turning shopping into something closer to a personal shopper than a scrolling marathon.
In this episode, Georgie Brown and Kathleen unpack how Tote is rethinking fashion discovery, why personal style has become so hard to define online, and what it takes to build a startup that balances speed, intention, and community.
In this episode, we cover:
Why online shopping feels exhausting, not exciting
How Kathleen went from sustainable fashion founder to fashion-tech builder
The difference between trends and true personal style
Why discovery — not checkout — is the real problem in e-commerce
How Tote works (and why users describe it as “BeReal for outfits”)
Building an AI stylist that learns your taste, not the algorithm’s
The role of community in making style feel safe and personal
Tote’s future plans, including B2B partnerships with fashion brands
Whether you love fashion or dread shopping altogether, this episode is a refreshing look at how technology can support self-expression instead of overwhelming it.
Key Takeaways:
Choice overload is killing joy: Too many brands and trends make shopping harder, not better.
Style is personal, not performative: Tote focuses on what people actually wear, not what’s trending.
Discovery is the real pain point: Most people don’t need more products — they need better guidance.
AI works best with context: Logging real outfits helps Tote deliver genuinely relevant recommendations.
Community builds confidence: Seeing how others dress creates trust and relatability.
B2B is the next frontier: Tote plans to power personalised shopping experiences for brands, not just consumers.
Chapters / Timestamps:
00:00 — Why online shopping feels broken
04:10 — Kathleen’s journey from fashion founder to tech startup
07:11 — The discovery problem in e-commerce
10:02 — Who Tote is built for
12:54 — How Tote works (from outfits to recommendations)
15:36 — B2B ambitions and brand partnerships
17:55 — The realities of building a startup
20:55 — Advice for early-stage founders
21:45 — Founder shout-outs
22:37 — The future of personalised shopping
View all episodes
By Georgie BrownWhat if shopping online actually understood you — your wardrobe, your taste, your real-life style — instead of throwing endless trends and products your way?
That’s exactly the problem Kathleen Sheppard set out to solve with Tote, a personalised fashion-tech platform designed to help people cut through the noise and rediscover their own style.
Tote flips the traditional shopping model on its head. Instead of starting with products, it starts with you. Users log their outfits, build a picture of their real wardrobe, and receive tailored recommendations from an AI stylist — turning shopping into something closer to a personal shopper than a scrolling marathon.
In this episode, Georgie Brown and Kathleen unpack how Tote is rethinking fashion discovery, why personal style has become so hard to define online, and what it takes to build a startup that balances speed, intention, and community.
In this episode, we cover:
Why online shopping feels exhausting, not exciting
How Kathleen went from sustainable fashion founder to fashion-tech builder
The difference between trends and true personal style
Why discovery — not checkout — is the real problem in e-commerce
How Tote works (and why users describe it as “BeReal for outfits”)
Building an AI stylist that learns your taste, not the algorithm’s
The role of community in making style feel safe and personal
Tote’s future plans, including B2B partnerships with fashion brands
Whether you love fashion or dread shopping altogether, this episode is a refreshing look at how technology can support self-expression instead of overwhelming it.
Key Takeaways:
Choice overload is killing joy: Too many brands and trends make shopping harder, not better.
Style is personal, not performative: Tote focuses on what people actually wear, not what’s trending.
Discovery is the real pain point: Most people don’t need more products — they need better guidance.
AI works best with context: Logging real outfits helps Tote deliver genuinely relevant recommendations.
Community builds confidence: Seeing how others dress creates trust and relatability.
B2B is the next frontier: Tote plans to power personalised shopping experiences for brands, not just consumers.
Chapters / Timestamps:
00:00 — Why online shopping feels broken
04:10 — Kathleen’s journey from fashion founder to tech startup
07:11 — The discovery problem in e-commerce
10:02 — Who Tote is built for
12:54 — How Tote works (from outfits to recommendations)
15:36 — B2B ambitions and brand partnerships
17:55 — The realities of building a startup
20:55 — Advice for early-stage founders
21:45 — Founder shout-outs
22:37 — The future of personalised shopping