Rob shows us what it takes to transition out of the structure and stability of the familiar path and embark on something creative and entrepreneurial.
Raised in Kent in the south of England, Rob spent a decade working in partnerships for the Cannes Festival of Creativity before deciding to move away from the success and stability he’d built. Through a recalibration of his mindset, a reconnection to his values, and adopting a new approach to the process of evolving his career, Rob found his ideal next step as the founding partner of Super Okay, the creative design studio.
Outside of work Rob is a photographer, avid record collector, and occasional DJ.
In this episode, we talk about:
- Leaving something successful, stable, and structured that no longer feels meaningful
- Letting go of classic markers of career success like title, brand-name, and money
- How he navigates the rollercoaster of entrepreneurship.
- The power of vulnerability when building a business
- The mix of humility, humor, and curiosity that keeps you grounded
Rob is funny, vulnerable, and honest about the messy process of becoming yourself.
If you’re navigating change or craving more alignment, this episode is for you.
Timestamps:
00:00 – Intro
03:05 – Growing up in a creative household
04:03 – Early career: Cannes Lions & advertising
05:44 – Discovering creativity through business development
07:53 – Burnout, cycles, and the March 2020 pause
09:27 – Redefining success beyond money & titles
11:53 – Discovering personal and professional values
13:46 – The power of conversations & networking
15:18 – Breaking down old identities and rebuilding
16:10 – Personal work: alcohol, mental health & avoidance
18:46 – Acceptance, self-awareness & emotional regulation
20:26 – The roller coaster of self-growth
21:10 – Becoming an entrepreneur
22:24 – Separating self-worth from business success
24:30 – Fulfillment through people, clients & values
27:54 – Anxiety, fear & resilience in entrepreneurship
31:10 – Advice to his younger self
32:10 – Billboard message: “Know thyself”… or not
32:44 – “Make DJing cool again” hot take
34:14 – Closing reflections & gratitude
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Julia makes reinvention look easy. And she credits it to staying curious, believing in people, listening to herself, and cultivating optimism.
Growing up in the Soviet Union around the Black Sea, Julia’s curiosity, intuition, creativity, and tenacity eventually led her to local fame in Moscow as a music journalist for MTV Russia and early pioneer of internet television. She then reinvented herself as a techno dj in Berlin. In 2013 she moved to New York with no local community and without a strong grasp of English. She navigated this challenge by throwing herself into music production and launching her own record label, Jujuka Music.
Today Julia is renowned internationally for her innovative sound; The New Yorker called her music beguiling. She’s a regular at Tresor in Berlin and holds a residency at Public Records in New York where she also does programming focusing on modern techno and obscure club music.
She’s also currently realizing a long-held dream of having a space where she can host friends, create events, and pour people drinks as the managing partner of the artist-run bar E-Flux Bar Laika in Clinton Hill in Brooklyn.
In this episode, we get into 1. How curiosity and tuning into yourself is the foundation for your evolution 2. The power of optimism and seeing life as full of possibilities 3. The opportunities created from seeing the good in people 4. Managing multiple major life transitions at once with no safety net 5. Julia’s philosophy on the duality required to be a strong artist 6. How experience helps your course correct in a more aligned way 7. Navigating an industry that will judge you first on your looks 8. The magnetic power of having character
Julia is warm, funny, and honest about her journey and what it takes to build a life with character, one that takes you to places you would’ve never imagined.
If you’re considering a new transition, building a career based in creativity, or navigating a hard moment, this episode is for you!
Timestamps:
00:00 – Listening to Yourself & The Challenge of Transition
01:49 – Childhood in the Soviet Bloc & Identity Shifts
02:32 – Success vs Experience: Julia’s Reframe
03:15 – Intuition as a Superpower
06:00 – Reinvention Series: Journalist → MTV Host → Blogger → Producer → DJ → Cultural Curator
09:14 – Anger, Negativity & How to Avoid Getting Stuck
11:43 – From “Somebody” in Russia to “Nobody” in NYC
13:09 – A New Poem for a New Chapter
14:47 – Looking Back at the Years of Disguise
15:42 – Toxic Work Environments & Energy Absorption
18:56 – Style as Practicality, Comfort & Movement
20:31 – The Pressure on Women in Electronic Music
22:47 – Collaboration, Trust, and Creative Partnerships
23:38 – The Hard Work Behind a “Lucky” Career
24:56 – Community, Dance Floors & Cultural Responsibility
27:24 – What She’s Working On Now
28:15 – Advice for Anyone in a Transition
29:32 – What Character Means to Julia
Do you ever feel like the career you built is the one you thought you wanted - but then you wake up one day and realize it’s no longer clicking?
That’s where Caroline Witmer found herself. Brown grad. Columbia MBA. Wealth management. Private equity. She’d ticked all the boxes, jumped from chapter to chapter with ease, externally she was ‘crushing it’… but never looking inside to ask herself, are you happy? Is this really what you want?
In this episode of Character, I sit down with Caroline—who's actually a former coaching client of mine—to talk about her journey from finance to founding Tuck Shop, a handcrafted chocolate company capturing the spirit of your happy place.
Caroline shares how she’s building something meaningful while raising three kids under four without the pressure and intensity that colored her career in finance.
In this honest conversation about career change and building a life with character, we explore:
- How do you know when it’s time to leave a career that looks good on paper?
- Letting go of other people’s opinions.
- Giving yourself permission to play.
- Building a business while raising babies.
- What it takes to let go of the pressure and hold things looser.
Connect with Caroline and Tuck Shop:
Website: https://shoptuckshop.com/
Instagram:
@shoptuckshop https://www.instagram.com/shoptuckshop/
Timestamps:
00:00 Introduction & Early Aspirations
01:33 Path into Finance
03:38 Finance Career Growth
05:15 Business School & Transitioning Roles
07:04 COVID & Life Changes Triggering Reflection
09:08 Coaching & Transitioning Mindset
12:43 Shifting from Finance to Entrepreneurship
16:25 Founding TuckShop
20:01 TuckShop Growth & Operations
24:24 Learning Operational Skills
27:14 Spirituality & Grounding Practices
29:18 Balancing Motherhood & Entrepreneurship
32:38 Impact of New York City on Career & Creativity
34:53 Advice to Younger Self & Key Takeaways
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What happens when you build something you thought would work and then it doesn’t? And there’s no plan B.
Sutian Dong, Partner at Multitudes and Co-Founder of Global Women in VC, is fascinated with creating products, technologies, platforms, services, and communities that move humanity in a positive direction by not changing how we do things, but the way that we think and feel. After years of lucky breaks and things always just working out, Sutian found herself in uncharted territory when her original concept for Multitudes failed and she had no idea what came next. That moment of disorientation became the catalyst for profound self-inquiry that ultimately sparked the insights that created her new venture, Multitudes, which invests in and incubates ideas that explore the edge of human consciousness.
This conversation is a reminder that growth isn’t always a straight line and that the best ideas often happen when you give yourself permission to rest and reflect.
On this episode of Character, Sutian joins me to talk about:
Why running a business is one of the rawest forms of self-expression
The modalities Sutian used to move through processing failure and figuring out what came next
Navigating discomfort to support your growth
The relevance of spirituality in the modern world
Using tools like astrology, tarot, and aura photography to access self-connection and build community
The second-order effects of AI
Multitudes’ approach to investing in initiatives at the edge of human consciousness
This episode was recorded at Love Letter, an aura photography studio, on the Lower East Side.
Learn more about Sutian’s work: https://www.sutiandong.com/Learn more about Love Letter: https://www.loveletter.nyc/
TIMESTAMPS:
00:00 — The Power of Pause
00:52 — Meet Sutian Dong
02:10 — Childhood Dreams
04:17 — Growing Up Entrepreneurial
05:30 — From Structure to Self-Reliance
07:34 — When Success Stops Working
09:56 — Forced Introspection
11:50 — Feeling the Feelings
13:57 — Tools for Healing
16:35 — The Gradual Sunrise of Change
19:16 — Compounding Change & Self-Advice
20:58 — Redefining Venture Capital
23:01 — The Power of Belief Systems
24:08 — Following Curiosity
25:57 — Flux and Rebirth
27:10 — Searching for Meaning in Chaos
What does it mean to build a life around authenticity, intuition, and joy—even when it defies expectations?
Ariel Palitz, nightlife veteran, entrepreneur, and former NYC Nightlife Mayor, joins me for a conversation about defiance, self-discovery, and designing a life by trusting what feels good. Growing up in Manhattan, Ariel found herself drawn early to the freedom of nightlife as a place where she felt most alive. From experimenting with PR and music, to opening her own nightclub, to ultimately creating a career at the intersection of community, culture, and advocacy, Arielle’s story is one of resilience, intuition, and flow.
On this episode of Character, Arielle joins me to talk about:
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What does it take to leave behind security and familiarity and start over in pursuit of purpose?
Brandon Ross, a former flight attendant turned massage therapist and founder of Romie Massage in New York City joins me for a story of reinvention, courage, and self-acceptance.
From a delayed blooming growing up gay in a conservative Christian household, to an angry rebellion as he built his first career as a flight attendant, and then switching it all up to create an entrepreneurial career around what energized him, Brandon’s story is one that anyone who dreams of more can learn from!
On this episode of Character, Brandon joins me to talk about:
Navigating his love for dance and choreography while growing up in a strict religious household that didn’t embrace this self-expression
The freedom and adventure he found as a flight attendant — and why it ultimately left him searching for more
How he discovered massage therapy through years of travel, curiosity, and noticing the artistry of touch
The leap of faith it took to leave corporate stability and build his own practice
Lessons on identity, devotion over discipline, and the importance of surrounding yourself with people who believe in your vision
TIMESTAMPS:
00:00 – Meeting Brandon at a Buffalo party
01:15 – Wanting to be a choreographer
04:50 – Growing up in a strict household
08:10 – Flight attendant years & freedom in travel
14:30 – Discovering massage therapy
19:20 – Taking the leap into entrepreneurship
22:30 – Staying committed through challenges
26:20 – Devotion vs discipline
27:50 – Flow and alignment through massage
28:50 – Tools for reconnecting with self
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What if finding true connection had less to do with swiping on apps—and more to do with romancing yourself and showing up authentically in the world?
Amy Van Doran — matchmaker, CEO, and founder of The Modern Love Club — joins me for a deeply inspiring conversation about love, identity, and why community and spirituality matter more than ever.
On this episode of Character, Amy shares:
- How her unconventional childhood shaped her unapologetic sense of self
- Why loneliness can be transformed into a gift that fuels connection
- The parallels between careers and romantic relationships — and why both require risk, curiosity, and play
- How creating community might be the real antidote to our modern dating crisis
SUBSCRIBE NOW:
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How does an Argentinian psychoanalyst and sommelier with no formal design training build a beloved fashion and bridal line in New York City? We dive into Delfina’s journey in the first episode of Character and discuss:
The culture and influences that shaped her early career and life in Buenos Aires
Making the move to New York and exploring a variety of careers
Using intuition to guide the launch of her first collection and the launch of her widely successful non-traditional bridal line
The powerful role ayahuasca played in her ability to navigate this growth and tap into her authentic self-expression and creativity
The lessons learned from 14 years living in New York and building her own brand
Subscribe to the Character Substack for:
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Want to create an energizing career you love like Delfina?
Learn more about Anne’s unconventional career coaching that blends deep healing with neuroscience and classic career tools to help you create clarity, momentum, confidence, and deep self-trust.
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Website: https://www.annebenveniste.com
LinkedIn: linkedin.com/in/annebenveniste/
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New York City is full of characters: unapologetically authentic people who create the vibe that make this city great. People who have thrown out the rulebook and become the artist of their life.
We dive into the messy, unpredictable journey towards fulfillment and authentic self-expression. We talk to creatives and artists, entrepreneurs and change-makers about where they came from, who they’ve become, and what it took to get here. These are honest, intimate conversations, where we explore taking risks, trusting your intuition, career twists, creative awakenings, and the role this intense and powerful city played in shaping their path. We explore the structures and tools they used to support them - from psychedelics to therapy, spirituality to community.
We get real. We have fun. We go deep. Always in the quest to leave you wiser and more inspired. This show is about the character it takes to build an authentic and fulfilling life that feels uniquely your own.
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