#93 - Anna Roubos, 2x Founder, Friend, Mama: On Failure, Fintech, Divorce, Motherhood and Investing

#93 - Anna Roubos, 2x Founder, Friend, Mama: On Failure, Fintech, Divorce, Motherhood and Investing

In this episode, Kylie talks with a dear friend, past colleague, PR agency and fintech startup founder, mama, and comms specialist extraordinaire Anna Roubos about life, and life after.

Anna and Kylie have been acquainted for over a decade and spent years working with scrappy startups together in the trenches of a (then new and up and coming) SF PR agency, Method Communications. Since that time, a lot has changed.

The two are reconnecting for a deep, vulnerable discussion on life after the last decade.

On loss, on divorce, on dating. On finding your passion and using it as purpose during evolutionary periods.

This episode is literally for the girls. Listen if you want to feel like you’re talking with a best friend who also happens to be smart, financially literate (Anna will like this one!) and wants less aesthetics, and more reality.

Connect with Anna on LinkedIn here or on Instagram here.

Connect with Kylie here.

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Jaksot(93)

#91 - Why Women Feel Restless Right Now | Uranus in Gemini Explained

#91 - Why Women Feel Restless Right Now | Uranus in Gemini Explained

✨ EPISODE SUMMARY ✨In this episode, Kylie explores the powerful energetic shift happening as we enter Gemini season and the larger Uranus in Gemini era — and why women everywhere suddenly feel the urg...

27 Touko 1h 8min

# 90 - 🌙 The Astrology of Motherhood in 2026: Why Everything Feels Like It’s Shifting

# 90 - 🌙 The Astrology of Motherhood in 2026: Why Everything Feels Like It’s Shifting

In this episode, Kylie speaks to the quiet but undeniable shift many mothers are feeling right now—the sense that something deeper is changing. Through an exploration of current astrological transitio...

1 Huhti 24min

#89 - The Identity Economy Comes for Corporate America

#89 - The Identity Economy Comes for Corporate America

In this episode, Kylie gets real about the tension between 🧠 expertise and 💫 identity — and what happens when your job title no longer feels like your truth.After years of chasing promotions, perfor...

4 Maalis 38min

#88 - The Art of Editing Your Own Life

#88 - The Art of Editing Your Own Life

🎙️ Episode 133: The Art of Editing Your Own Life ✍️✨In this episode, Kylie dives deep into the idea that we’re all editors — not just of our feeds or wardrobes, but of our stories. 💭 From rewriting ...

25 Helmi 30min

#87 - What Death Anxiety Can Teach You About Living Fully

#87 - What Death Anxiety Can Teach You About Living Fully

Lately, Kylie’s been lying awake wondering — why do I keep thinking about death? 💭 Turns out, those late-night spirals aren’t about fear… they’re about purpose.In this soul-searching solo episode, Ky...

11 Helmi 24min

#85 - You Don’t Have to Know What’s Coming Next (You Just Have to Trust Yourself)

#85 - You Don’t Have to Know What’s Coming Next (You Just Have to Trust Yourself)

There's a quote in a new book I'm reading, The Alchemist, that says — “People need not fear the unknown if they are capable of achieving what they need and want.”When I first read that, it stopped me ...

15 Tammi 28min

#86 - Riding the Fire Horse: How to Harness 2026’s Most Transformative Energy

#86 - Riding the Fire Horse: How to Harness 2026’s Most Transformative Energy

In this episode, Kylie dives deep into the rare and transformative energy of the Year of the Fire Horse — a once-in-sixty-years cosmic cycle that calls us to burn away illusion and live from radical t...

15 Tammi 20min

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