Paul Orlando didn’t set out to become an entrepreneur.

Earlier in his career, he worked in corporate roles at AT&T and in management consulting, advising large Fortune 100 and Fortune 500 companies. Then a restructuring eliminated his entire practice, and instead of looking for another job like it, Paul started exploring what else he could build.

That eventually led to Chatfe, a startup that began as a way for strangers to have spoken conversations and later focused on connecting people recovering at home with others who understood what they were going through.

The experience changed the way Paul thought about entrepreneurship.

Today, he runs the startup incubator at USC, teaches entrepreneurship, writes about startups and business strategy, and has worked with hundreds of founders across different industries and countries.

Along the way, he’s learned that entrepreneurship isn’t about avoiding every mistake. Some mistakes are unavoidable. The real skill is recognizing patterns, adapting quickly, and understanding which decisions you can make better next time.

This conversation goes far beyond startups. We talk about:

• Why Paul says he was essentially “forced” into entrepreneurship

• What building his first startup taught him about figuring things out

• The simple co-founder conversation that he says can prevent major problems later

• What entrepreneurship can actually be taught and what may be harder to teach

• Why “agency” and the ability to figure things out matter so much

• How AI is changing what a solo founder can build

• Why Paul made AI mandatory in his classrooms rather than banning it

• What happened when he gave the same assignment before and after ChatGPT

• Why he believes some things still need to be learned the hard way

• What he learned building startup ecosystems in New York, Hong Kong, and Los Angeles

• How culture can dramatically change the speed at which people build relationships and businesses

• Why Hong Kong had incredible connectivity but a very different startup culture

• Why being too early can be more dangerous than being too late

• How to think about “Why Now?” without pretending you can predict the future

• What founders should look for when deciding whether a market is actually ready

• The things Paul believes won’t change even as technology does

• Why economic resilience requires both a financial buffer and the ability to change direction

• How having side projects can create optionality when your career changes unexpectedly

• The 30-day “rejection therapy” challenge he gives his students

• What more than 300 companies have taught him about the fundamentals of building a business

• Why understanding customers, sales, and unit economics still matters—even in the age of AI

• Whether Paul would ever become a founder again

Paul’s story is a reminder that careers rarely unfold according to plan.

Sometimes a layoff becomes a startup. A startup becomes a lesson.

And a lesson becomes a career helping other people build what comes next.

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A Line From the Conversation

“It is more dangerous to go in early because if the business model does not mean that we could build a financially sustainable business for years, then we are just losing money.”

Favorite Book

Erewhon by Samuel Butler

Paul’s recent pick is a particularly fitting one for this conversation: a utopian novel about a society that has deliberately prohibited certain technologies. It became a jumping-off point for a conversation about our relationship with technology, what happens when we intentionally stop technological progress, and how dependent we have already become on tools like AI.

In This Episode

In this conversation:

(00:00) Intro — Paul’s unconventional path into entrepreneurship
(02:00) From corporate jobs to becoming a founder
(03:39) Building Chat Faye and discovering the founder journey
(05:48) Can entrepreneurs avoid mistakes?
(07:26) The co-founder mistake that can be prevented
(10:34) What Paul learned from founders as an incubator leader
(12:51) Can entrepreneurship actually be taught?
(15:15) Agency, resilience & figuring things out
(17:05) Solo founders and what AI changes
(18:38) How Paul accidentally ended up teaching at USC
(22:05) Teaching entrepreneurship in the age of AI
(23:22) What happened when ChatGPT entered the classroom
(25:08) The AI experiment that changed what Paul saw in his students
(27:15) Learning the hard way in an AI world
(30:07) Reading old books, screens & staying curious
(33:26) Building startup ecosystems across New York, Hong Kong & LA
(36:14) Why Hong Kong moved at a different speed
(39:42) The challenges of building startups in Hong Kong
(45:15) Why being too early can be more dangerous than being too late
(47:16) Understanding “Why Now?”
(49:49) What do you do when you’re too early?
(53:32) What doesn’t change in a rapidly changing world?
(57:52) Economic resilience & surviving uncertainty
(01:01:22) Staying agile when your industry disappears
(01:04:15) The 30-day rejection therapy challenge
(01:06:40) What 300+ companies have taught Paul
(01:11:12) Would Paul become a founder again?
(01:12:05) Erewhon, technology & the future
(01:14:45) Final thoughts

The world is changing faster than ever.

But some things remain remarkably constant: understand your customer, build something people will pay for, learn continuously, and be willing to change direction when reality tells you to.

Paul’s journey is ultimately about that tension: knowing what to hold onto, knowing what to change, and learning how to keep moving when the path isn’t obvious.

If you’ve ever wondered whether you’re too early, too late, or simply on the wrong path, this conversation is for you.

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Lekha Vyas is the founder and CEO of SynQ Wellness, building sublingual supplement strips designed to make it easier for people to actually get the nutrients their bodies need. Before that, she spent years moving up the corporate ladder fast at P&G, L’Oréal Luxury, Chanel, Estée Lauder, and a stint in private equity doing M&A.

But her path to becoming a founder was anything but conventional.

Lekha was born in India and moved constantly growing up before landing in Michigan for school. Out of the twelve jobs she applied for, she got eleven offers; by every conventional measure, she’d made it.

Everything changed when her mother was diagnosed with stage four breast cancer. Lekha built her first company, Elvy Lab, with her mom working on it together in the hospital during her treatment. A trademark dispute with a much larger brand eventually forced her to legally separate the two ventures, and what would become SynQ Wellness was born directly out of watching her mom struggle to get basic nutrition through a feeding tube during chemo. Her mother passed away two years ago. Instead of stepping back from building, Lekha built her way through the grief.

This conversation goes far beyond wellness startups. We talk about:

Why Lekha walked away from a fast-rising corporate career at P&G, L’Oréal, Chanel, and Estée Lauder

Growing up in a matriarchy and how it shaped who she became as an adult

Building her first company with her mom in a hospital room during chemo

The trademark dispute that forced her to legally split her business in two

Why she built SynQ Wellness directly out of watching her mom struggle to get nutrition through a feeding tube

Hitting rock bottom more than once, and what it actually takes to come back from it

Why women are taught to hold their emotions in, and what happens when you do it for years

Being a sponge for feedback, and why taking it well disarms people

Leaning on friends and learning not to push people away when she’s struggling

Finding her way back through dance, creativity, and small daily rituals for her inner child

The Bhagavad Gita, The Alchemist, and what grief taught her about faith

What she’s building next in female hormone health

Lekha’s story is a powerful reminder that having it all was never something you could actually measure. Sometimes the bravest thing you can do with an unbearable loss is build something real out of it.

🎧 Listen to the episode

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Favorite Quote

“You gotta save yourself, because nobody else is gonna come save you.”

Favorite Books

The Alchemist by Paulo Coelho

The Bhagavad Gita — a childhood ritual with her nani that she’s returned to since a solo trip to Varanasi

In This Episode

In this conversation:

(00:00) Intro — Lekha’s unconventional journey
(02:51) Moving, adapting & growing up in a matriarchal family
(07:31) Grief, loss & becoming a different version of yourself
(16:01) Being the “black sheep” & learning to prove yourself
(17:15) Gender bias and the assumptions women face
(19:24) From P&G to climbing the corporate ladder
(25:08) Losing her mother & hitting rock bottom
(27:27) Varanasi, spirituality & learning to surrender
(30:12) How her mother’s illness inspired her founder journey
(32:18) Building Sync Wellness around a real problem
(35:07) Building credibility outside your traditional expertise
(38:51) Women’s health, hormones & the future of wellness
(42:28) The reality of leaving corporate to become a founder
(44:39) What it really costs to build something of your own
(45:35) The support system you need to take the leap
(47:28) Why being “strong” can make it harder to ask for help
(55:38) The inner child, the parent & the adult
(59:39) The quote and book that guide Lekha now

Lekha’s story reminds us that strength isn’t about doing everything alone.

Sometimes, it’s about knowing when to let people in.

If you’ve ever questioned whether you’re taking the “right” path, this conversation is for you.

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In this episode of Be Anomalous, Solai joins me for an honest conversation about unconventional careers, angel investing, identity, calculated risk, and what it means to trust your own path, even when it doesn’t make sense to everyone else.

Solai is an investor, advisor, board member, writer, speaker, teacher, and founder. She has built what she describes as a portfolio career, bringing together her experience across investing, startups, governance, and entrepreneurship.

But her path to becoming an investor was anything but conventional.

Solai began her career as an actuary, working in financial risk and analysis before spending years in the corporate world. Eventually, curiosity led her to take a different path.

She joined a startup. That experience changed the way she thought about work, growth, and what was possible.

She went from working inside a large corporation with clearly defined roles and systems to working in a company with just a handful of people—where everyone had to build, experiment, and figure things out as they went.

Her curiosity about the startup ecosystem eventually led her to angel investing.

Instead of using money she had set aside for an MBA, Solai began investing in early-stage companies, using the process to learn.

She calls it her own version of a “practical MBA.”

Over time, she developed her approach to investing, learning not only how to evaluate businesses but how to observe founders, understand execution, and recognize the difference between what someone says they will do and what they actually build.

As an Australian of South Asian heritage, Solai has also spent much of her career in rooms where she was one of the few people who looked like her.

Earlier in her career, she often felt the pressure to prove herself.

Over time, that changed.

She learned that being dismissed or underestimated often says more about the other person than it does about you, and that confidence doesn’t always come from proving yourself to the world.

Sometimes, it comes from investing in yourself and becoming more comfortable with who you already are.

But this conversation goes far beyond investing.

We talk about:

• Why Solai chose to leave a structured corporate career for the uncertainty of a startup

• How working as an operator shaped the way she thinks as an investor

• Why she used money saved for an MBA to begin angel investing

• What she calls her “practical MBA”

• How to think about risk before making your first investment

• Why early-stage investing isn’t about getting your money back quickly

• What Solai looks for when evaluating founders

• Why execution matters more than simply having a great idea

• How investors can unconsciously gravitate toward founders who are similar to them

• The importance of transparency and mutual respect between founders and investors

• The power imbalance that can exist when founders raise capital

• What founders need to understand about equity, dilution, and fundraising

• Why having a rigid exit strategy too early can be a distraction

• How founders can learn to delegate and let go as their companies grow

• What it means to build a portfolio career

• Navigating spaces where you’re one of the few people who look like you

• Why investing in yourself can be the best investment you make

• How confidence can become more internal over time

• What Solai is learning about the next generation of founders

• How AI is helping founders move faster—and where it can go wrong

• Why curiosity has been the common thread throughout her unconventional career

Solai’s story is a powerful reminder that you don’t need to have your entire life mapped out before taking the next step.

Some of the most meaningful opportunities in her career came simply from following her curiosity.

🎧 Listen to the episode

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Favorite Quote

“Leap and the net will appear.”

Favorite Books

The Life-Changing Magic of Tidying Up by Marie Kondo

Quit by Annie Duke

In This Episode

(00:00) Meet Solai and her unconventional portfolio career
(01:00) Growing up between New Zealand, Australia, and South Asian identity
(03:30) Why Solai became an actuary
(05:30) From corporate life to the startup world
(09:00) What working as a startup operator teaches you about growth
(12:30) How curiosity led Solai into angel investing
(15:30) Creating a “practical MBA” through investing
(18:30) What first-time angel investors need to understand about risk
(22:00) How Solai evaluates founders and what she looks for
(25:00) Being an outsider in rooms where you don’t look like everyone else
(29:00) Why confidence has to become an internal process
(33:00) Power dynamics between founders and investors
(36:00) Equity, dilution, and the realities of raising capital
(40:00) Why founders need to think long-term
(43:00) Learning when to delegate and let go as a founder
(46:00) Building Chai and Capital and exploring the India–Australia tech ecosystem
(50:00) What Solai is learning from the next generation
(53:00) AI, agents, and the danger of AI slop
(56:00) The unconventional career moves that shaped Solai’s journey
(58:00) Solai’s favorite quote and the lessons behind knowing when to leap

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In this episode of Be Anomalous, Dr. James Richardson joins me for an honest conversation about unconventional careers, entrepreneurship, neurodivergence, and what it means to build a career around the way you actually think.

James is a professionally trained cultural anthropologist turned business strategist, the author of the award-winning business book Ramping Your Brand: How to Ride the Killer CPG Growth Curve, and the founder of Premium Growth Solutions, a strategic planning consultancy for emerging consumer packaged goods brands.

He has helped more than 150 CPG brands with their strategic planning, including Dude Wipes, Once Upon a Farm, Dr. Squatch Soap, Trü Frü, Earth Breeze, Dr. Bronner’s, Happy Egg, and Made Good.

But his path to becoming a business strategist was anything but conventional.

After leaving academia, James had to teach himself how business worked. He learned by stepping into rooms he wasn’t necessarily qualified to be in, making mistakes, enduring discomfort, and figuring things out along the way.

As a highly functioning autistic professional, James also spent much of his career trying to understand environments, expectations, and social rules that didn't always come naturally to him. Over time, he learned he didn't necessarily need to change who he was; he needed to understand how he worked and build an environment that let his strengths come through.

And that outsider perspective eventually became one of his greatest strengths.

But this conversation goes far beyond business strategy.

We talk about:

• Why James left academia and had to teach himself business

• What happens when you’re the outsider in a room full of people who think you don’t belong

• Why being willing to look foolish can accelerate your learning

• How his background in cultural anthropology shaped the way he approaches business

• Neurodivergence, self-awareness, and learning to work with your brain rather than against it

• Why traditional networking didn’t work for him and how he built authority through content instead

• The unconventional path to becoming an independent consultant

• Why founders should never make major business decisions from a place of panic

• The importance of cash-flow forecasting and understanding the math behind your business

• Why “growth at all costs” can be dangerous for emerging brands

• The realities of raising money and the risks founders need to understand

• Why sometimes the smartest move for a struggling business is to shrink before it grows again

• The difficult conversations consultants have to be willing to have with founders

• Why successful founders can become vulnerable to distraction once they have money and momentum

• What James has learned from working with more than 150 CPG brands

James doesn’t romanticize entrepreneurship.

He challenges a lot of the conventional advice founders hear about funding, scaling, distribution, and growth—and offers a much more grounded perspective on what it actually takes to build a sustainable business.

🎧 Listen to the episode

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Favorite Quote

“Never make friends in haste.”
— Tiruvalluvar, from his 2,000-year-old book of aphorisms from Tamil India

Favorite Book

Never Split the Difference by Chris Voss

In This Episode

(00:00) Meet Dr. James Richardson and his unconventional path
(02:00) From cultural anthropology to business strategy
(06:00) Learning business without an MBA
(09:00) Being an outsider and learning through discomfort
(13:00) Neurodivergence, research, and finding your own way of working
(18:00) Why networking matters—and why it didn’t come naturally to James
(21:00) Building a consulting business around your strengths
(29:00) Using content to build authority instead of traditional networking
(34:00) The truth about growing an emerging CPG brand
(38:00) Why founders shouldn’t make decisions while panicking
(42:00) Cash flow, contribution margins, and doing the math
(47:00) Raising money without losing control of your business
(52:00) The risks founders need to understand when taking outside capital
(55:00) The tough conversations successful founders need to hear
(59:00) Knowing when to focus, shrink, or change direction
(01:03:00) What being an outsider can teach us about building your own path

New episodes drop every Tuesday.

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Episode Description

In this episode of Be Anomalous, Rebecca Bartlett joins me for an honest conversation about entrepreneurship, creativity, motherhood, and what it really means to build a business on your own terms.

Rebecca is the Founder and Creative Director of Bartlett Brands, the agency behind some of the beauty and wellness industry’s most recognizable startups. After beginning her career inside one of beauty’s fastest-growing companies, she left corporate life to help founders build brands from the ground up—partnering with visionary entrepreneurs from day zero.

But this conversation goes far beyond branding.

We talk about:

• Why leaving corporate wasn’t the hardest part—learning to sell herself was

• The confidence gap women are taught to live with

• Negotiating your worth and unlearning the need to stay small

• Why startup founders need courage more than certainty

• Building brands that take risks instead of playing it safe

• The importance of trusting your intuition when choosing clients and making decisions

• Motherhood, ambition, and the impossible expectations placed on women

• The myths around postpartum, work-life balance, and “having it all”

• Why slowing down can actually make you a better leader

• What separates brands that survive from those that disappear

Rebecca’s story is a reminder that success isn’t about chasing someone else’s definition of achievement. It’s about building a life, a career, and a business that aligns with who you are—and having the courage to trust your own path.

🎧 Listen to the episode

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Favorite Quote

“You don’t have to burn it down. Sometimes you just need to slow down a little.”

Favorite Book

Out in the Woods by Gregg Olsen

In This Episode

(00:00) Meet Rebecca Bartlett and the story behind Bartlett Brands

(02:00) From corporate beauty to building brands from scratch

(05:00) Why women struggle to sell themselves and own their expertise

(08:00) Negotiating your worth and overcoming imposter syndrome

(12:00) Why startups succeed by taking risks, not avoiding them

(16:00) Choosing the right clients and trusting your gut

(21:00) Entrepreneurship, motherhood, and the pressure to do it all

(24:00) The reality of postpartum and breaking impossible expectations

(30:00) Why ambitious women need permission to slow down

(36:00) Building resilient brands that last beyond the hype

(42:00) Raising confident children and redefining success

(46:00) What it truly means to build an extraordinary life on your own terms

New episodes drop every Monday and Thursday.

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Episode Description

In this episode of Be Anomalous, Susanne Mitschke joins me for a conversation about entrepreneurship, clinical research, women’s health, and what it really takes to build a company that lasts.

Susanne is the co-founder and CEO of Citruslabs, a company helping consumer brands validate their products through decentralized clinical studies. Before building Citruslabs, she studied biostatistics and epidemiology, conducted research at Harvard, and founded a digital health startup focused on cognitive health.

But this conversation goes far beyond clinical trials.

We talk about:

• Why Susanne chose to build Citruslabs without venture capital

• The lessons she learned from her first startup and why revenue matters from day one

• What founders misunderstand about fundraising and investor incentives

• How Citruslabs grew organically through customer demand

• Hiring, leadership, and building a low-hierarchy culture

• Why women’s health has historically been underrepresented in research

• The role social media has played in pushing women’s health conversations forward

• Founder health, sleep, exercise, and sustainable performance

• Failure, resilience, and why unconventional paths require unconventional thinking

Susanne’s story is a reminder that success doesn’t always look like headlines, funding rounds, or hypergrowth. Sometimes it’s building something valuable, profitable, and resilient enough to still be here decades from now.

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Favorite Quote

“If you want to do something unconventional, you have to be unconventional and you shouldn’t follow conventional advice.”

Favorite Books

Extraterrestrial by Avi Loeb

A fascinating exploration of ʻOumuamua and the possibility of extraterrestrial life through the lens of one of Harvard’s leading astrophysicists.

Starter Villain

A humorous novel about an ordinary man who unexpectedly inherits a fortune—and a lot of cats.

In This Episode

(00:00) Meet Susanne Mitschke and the mission behind Citruslabs

(03:00) Growing up in Germany and choosing a career path at 17

(06:00) The first startup: MindMate and lessons from failure

(10:00) Why Citruslabs never raised venture capital

(16:00) Clinical research, transparency, and consumer health brands

(20:00) Why women’s health research has historically lagged behind

(23:00) The role of advocacy and social media in changing healthcare

(24:00) Founder health, sleep, and sustainable performance

(27:00) Building a team and hiring for culture fit

(30:00) What does success mean after building multiple companies

(33:00) Leadership, delegation, and letting people fail

(36:00) Why failure is necessary for growth

(37:00) Unconventional advice for unconventional founders

(38:00) Books, curiosity, and the search for bigger questions

New episodes drop every Monday and Thursday.

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Episode Description

In this episode of Be Anomalous, Hiba joins me for a conversation about identity, belonging, entrepreneurship, and what it truly means to bet on yourself before the path is clear.

Hiba is the founder of Twenty5% — a hybrid agency, studio, and media company for the South Asian and Muslim community. Her path to get here was anything but conventional: pre-med, cancer research at Northwestern, a pivot into the music industry, and eventually building the company she always knew the world needed — even when the world hadn’t asked for it yet.

But this conversation goes far beyond business.

We talk about:

• Growing up Indian and Muslim in the Midwest — and owning every part of that identity

• Leaving behind three high-paying pharmaceutical job offers to chase something she couldn’t fully name

• What the music industry taught her about creativity, community, and herself

• Cold outreach, cold starts, and why relationships are everything

• Bootstrapping Twenty5% and why she’s never had a scarcity mindset

• What real representation looks like — and why nuance is the only way forward

• The daily battle with self-doubt, and the gratitude practice that pulls her back

Hiba’s story is a reminder that the world doesn’t always have a blueprint for what you’re building. Sometimes you have to be the one to draw it.

🎧 Listen to the episode

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Favorite Quote

"If you focus on what you've left behind, you'll never see what lies ahead." — From Ratatouille

But she puts her own spin on it: don't ignore your past, learn from it. That's where resilience lives.

Favorite Books

No Rules Rules — the Netflix culture book. Learnings that stuck.

In This Episode

(00:00)Why Hiba leads with where she's from, not what she's done
(04:00) Growing up Indian and Muslim post-9/11
(08:00) How her parents raised her to be unapologetically herself
(12:00) Pre-med to cancer research, the path that taught her discipline
(17:00) The Shah Rukh Khan tour that changed everything
(22:00) What the music industry revealed about her creative side
(27:00) Mumbai vs. New York: the work cultures
(31:00) The origin of Twenty5% identity, community
(36:00) Why representation without nuance isn't enough
(41:00) How Twenty5% found its first clients
(46:00) The daily battle with self-doubt
(50:00) Vanity metrics, cold outreach
(54:00) Why are more people building their version of Twenty5% is the win
(57:00) Where she wants to take Twenty5% — a Hello Sunshine, an A24, for us

New episodes drop every Monday and Thursday.

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In this episode of Be Anomalous, I sit down with Aravinda Seshadri, founding partner of Venturous Counsel, a boutique law firm dedicated to serving underrepresented founders and diverse teams in tech. Aravinda’s story weaves together law, entrepreneurship, motherhood, and a mission to equalize access in Silicon Valley.

We talk about her unlikely path into law, leaving big firms where she never saw herself reflected, and starting her own practice while pregnant — a leap she says she made “too late, but just in time.” Aravinda opens up about battling imposter syndrome, learning to set boundaries, and why she built a firm that prioritizes humanity as much as transactions.

This episode is about courage, conviction, and carving out systems that don’t just profit a few — but empower the many.

If you’ve ever wrestled with self-doubt, considered a career pivot, or wondered whether kindness has a place in cutthroat industries, Aravinda’s journey proves it does.

🎧 Listen to the episode
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What You’ll Learn

• How Aravinda stumbled into law school and found her way to startup practice

• The difference between litigation and transactional law (and why she chose the latter)

• Why representation in law firms and startup ecosystems matters

• How growing up in Salt Lake City shaped her awareness of majority vs. minority dynamics

• The challenges of leaving a big firm (and why she waited longer than she should have)

• What it was like to launch a firm while pregnant — and hire her first associate who was also expecting

• How she built a fully remote, diverse team that thrives without an office

• Practical legal advice for founders on formation, fundraising, and avoiding costly mistakes

• Her philosophy on saying “no,” preserving team wellbeing, and choosing the right clients

Favorite Quote

“An eye for an eye makes the whole world blind.”
— Mahatma Gandhi

Favorite Books

📖 Venture Deals by Brad Feld
📖 Man’s Search for Meaning by Viktor Frankl

In This Episode, We Cover:

• (00:00) Life updates and the hidden struggles behind the highlight reel

• (05:00) Why Aravinda chose law and why she pivoted from litigation to startups

• (08:00) Leaving firms that didn’t reflect her and starting her own practice

• (10:00) Growing up South Asian in Salt Lake City and formative experiences with bias

• (14:00) The peer court convention story that cemented her passion for equity

• (17:00) Starting Venturous Counsel while pregnant — and what she learned from it

• (20:00) Hiring, trust, and building a culture that values humans first

• (23:00) Why pedigree matters less than skills (and how she tests for them)

• (26:00) On leaving too late, fear of uncertainty, and listening to yourself

• (29:00) The rise of remote work and what it means for law firms and startups

• (32:00) Boundaries, bad clients, and learning by doing it wrong first

• (37:00) Rethinking imposter syndrome and learning from bad managers

• (42:00) Advice for aspiring lawyers: explore, shadow, and choose deliberately

• (45:00) Advice for founders: start small, test your ideas, and listen to yourself

• (49:00) The legacy she hopes to leave with Venturous Counsel

• (50:00) When to get legal counsel, how much to budget, and why “legal debt” is real

• (56:00) Her favorite quotes and books

Where to Find Aravinda Seshadri

• Venturous Counsel

• LinkedIn

Referenced in This Episode

• Clerky (startup formation platform)

• Venturous Counsel Events

• Hustle Fund (Elizabeth Yin)

New episodes drop every Monday and Thursday.

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Episode Description

What does success really look like when you’re building a company, raising a child, and navigating an industry that wasn’t designed for you?

In this episode of Be Anomalous, Helen Diaz joins me for a powerful conversation about entrepreneurship, hospitality, motherhood, and redefining success on your own terms.

Helen is the co-founder of Chareau, the world’s first aloe plant-based spirit, and has helped grow the brand from a startup sold out of the trunk of a car into a nationally distributed company carried by Whole Foods Market, Total Wine & More, Marriott Hotels, and more.

Before Chareau, Helen spent over two decades in hospitality, co-owned Fifty Fifty Cocktail Co., developed bar programs from the Bay Area to Tokyo, became the first Latina to win Miss Speed Rack California, placed in the Top 8 nationally, and now serves as a judge for the prestigious San Francisco World Spirits Competition.

But this conversation goes far beyond business.

We talk about:
• Taking risks before you’re ready
• Building a company through uncertainty and the pandemic
• The realities of fundraising and scaling a brand
• Breaking barriers as a Latina woman in hospitality
• Motherhood, ambition, and work-life balance
• Why success means something completely different today than it did 10 years ago.

Helen’s story is a reminder that the biggest opportunities often begin with a leap of faith and that success isn’t about following someone else’s blueprint. It’s about creating your own.

If you’ve ever wondered whether it’s too late to start, too risky to pivot, or too ambitious to chase the life you really want, this episode is for you.

Favorite Quote

"Todo lo que siembre, cosecharás."

(Everything you put out into the world, you will receive.) — Helen's grandmother

Favorite Books

📖 Kitchen Confidential — Anthony Bourdain

📖 The Power of Now — Eckhart Tolle

In This Episode

(00:00) “I Am a Mama First” — Why Helen leads with motherhood
(04:00) Moving to SF at 19 with no plan
(07:00) How she got behind the bar — and why she loved it
(12:00) What hospitality taught her about resilience and emotional regulation
(18:00) Meeting Kurt at 5 am in New Orleans — and saying yes to Chareaux
(23:00) What makes Chareaux different: aloe, 80 calories, and half the sugar
(31:00) Bootstrapping, distributors, and knocking on every door in SF
(38:00) The pandemic wiped out 90% of their business overnight
(42:00) When your investor goes bankrupt — the real lessons in fundraising
(47:00) What motherhood taught her about burnout and leadership
(51:00) Success redefined: presence over performance
(53:00) Being the first Latina in the room — and why she never flinched
(57:00) What’s next: new line extensions and a coffee mountain in El Salvador

Referenced in This Episode

• Bourbon & Branch, Beretta, and Lolinda — SF cocktail bars where Helen honed her craft

• Total Beverage Solution Chareau’s current portfolio partner

• Whole Foods, the 2024 retail milestone that changed its visibility

• Eckhart Tolle, spiritual author and one of Helen’s go-to reads.

New episodes drop every Monday and Thursday.

Be Bold. Be Real. Be Anomalous.

Follow for more Be Anomalous stories, conversations, and behind-the-scenes.

Episode Description

In this episode of Be Anomalous, Steph opens up about the fear of judgment, self-doubt, motherhood, content creation, and the moment she finally stopped waiting for permission to pursue the life she actually wanted.

For years, she wrestled with the same fear so many people quietly carry:
What will people think of me?

But over time, she realized something deeper — the opinions of others matter far less than the regret of never trying.

This conversation explores the emotional reality of putting yourself online, building confidence before you fully feel ready, and learning how to trust yourself even when validation hasn’t arrived yet.

Steph shares how landing her first major brand deal became more than just a financial milestone. It became proof that her voice, creativity, and perspective had value. But more importantly, it gave her permission to stop shrinking herself.

We also talk about identity, motherhood, leading by example for your children, and why the most powerful thing you can do is show people what’s possible by living authentically.

This episode is about letting go of perfection.
Letting go of fear. And realizing your life is too important to be controlled by other people’s opinions.

🎧 Listen to the Episode

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

• Why fear of judgment keeps so many people stuck

• The mindset shift that helped Steph stop caring what others think

• How regret can become a stronger motivator than fear

• Why the first “proof of success” changes your confidence

• The emotional reality of becoming a content creator online

• How motherhood shaped the way Steph approaches risk and growth

• Why authenticity matters more than perfection online

• The connection between self-trust and creative freedom

• How to build confidence before you fully feel ready

• Why your children learn more from your actions than your advice

Favorite Quote

“ Be the change you wanna see in the world."”

Favorite Book

📖 Mindset — Carol S. Dweck

📖 The Miracle Morning — Hal Elrod

In This Episode

(00:00) Letting go of the fear of judgment

(03:00) Why regret became a bigger fear than failure

(07:00) The emotional reality of putting yourself online

(11:00) Learning to trust yourself before validation arrives

(16:00) The first major brand deal and what it changed internally

(21:00) Confidence, content creation, and self-worth

(27:00) Motherhood and becoming an example for your children

(33:00) Why authenticity resonates more than perfection

(38:00) Navigating criticism and public opinions online

(44:00) Building a life aligned with who you really are

(50:00) Advice for anyone afraid to start

Referenced in This Episode

• Steph’s course

• Content creation and personal branding

• Motherhood and identity

• Confidence and self-trust

• Authenticity online

• Creative entrepreneurship

• Personal growth and reinvention

• Overcoming fear of failure

New episodes drop every Monday and Thursday.

Be Bold. Be Real. Be Anomalous.

Follow for more Be Anomalous stories, conversations, and behind-the-scenes.

Episode Description

In this episode of Be Anomalous, Alix Peabody joins me for a raw conversation about entrepreneurship, burnout, identity, and what it really takes to build a category-defining brand from nothing.

Before Bev became one of the most recognizable canned wine brands in the country, Alix was hearing “no” over and over again. More than 200 investors passed on the idea. She was building in a male-dominated industry, navigating constant rejection, and trying to create a brand that didn’t fit the traditional rules of alcohol culture.

But this conversation goes far beyond startup success.

We talk about growing up between cultures, studying abroad as a teenager, building confidence through discomfort, and why entrepreneurship forces you to confront every version of yourself. Alix opens up about the emotional reality of scaling a company, the loneliness that comes with being a founder, and the identity shift that happens after an exit.

This episode is about resilience. About learning how to trust your instincts before the world validates you.
And about building something bold enough to change the culture around it.

🎧 Listen to the Episode

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

• Why 200 investor rejections didn’t stop Alix from building Bev

• The mindset shift founders need when fundraising

• How studying abroad shaped her confidence and adaptability

• What it’s really like building in a male-dominated industry

• Why branding is more about authenticity than expensive agencies

• The hidden emotional cost of entrepreneurship and burnout

• How the founder's identity becomes deeply tied to the company

• Why do second-time founders approach business differently

• The importance of routines, health, and mental resilience while building

• What founders misunderstand about success, scaling, and exits.

Favorite Quote

“Luck falls on the shoulders of those prepared to receive it.”

— Alix Peabody’s Grandfather

Favorite Book

📖 The Surrender Experiment — Michael Singer

In This Episode

(00:00) Who Alix Peabody is beyond Bev

(03:00) Growing up in New York with five siblings and studying abroad

(08:00) Why discomfort and movement shaped her entrepreneurial mindset

(12:00) From Bridgewater to Silicon Valley: building the foundation before Bev

(17:00) The origin story behind Bev and creating a brand with cultural impact

(23:00) Raising money after 200 investor rejections

(28:00) Building confidence as a woman in a male-dominated industry

(34:00) Hiring, leadership, and learning how to build the right team

(40:00) Burnout, sacrifice, and the emotional weight of entrepreneurship

(46:00) The reality of exits and losing your identity after building a company

(51:00) Founder loneliness, pressure, and mental health

(56:00) Why routines and self-care matter more than founders admit

(01:00:00) Advice for unconventional founders building something different

Referenced in This Episode

• Startup fundraising and venture capital

• Founder psychology and burnout

• Branding and consumer storytelling

• Women in entrepreneurship and leadership

• Identity, ambition, and resilience

• Building culture-driven consumer brands

• The emotional realities of startup exits

New episodes drop every Monday and Thursday.

Be Bold. Be Real. Be Anomalous.

Follow for more Be Anomalous stories, conversations, and behind-the-scenes.

Episode Description:

In this episode of Be Anomalous, Rama Afullo joins me for a conversation about identity, ambition, and what it really takes to build something the world doesn’t yet understand.

Rama isn’t just a founder.
He’s an engineer, systems thinker, and global citizen who has spent his life moving between countries, cultures, industries, and ideas.

Before founding Satlyt, a company building the future of orbital networking and AI infrastructure in space, Rama worked at Tesla, Google, and SpaceX. But this conversation isn’t about prestige.

It’s about conviction.

About what happens when you trust your vision before the market validates it.
When you walk away from stability to build something bigger than yourself.
And when your identity becomes the foundation, not the obstacle, to your ambition.

We talk about growing up across Africa and Europe, navigating race and belonging, surviving systems not built for you, and learning how power actually works inside some of the world’s biggest technology companies.

🎧 Listen to the Episode

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

• Why identity can become your greatest advantage as a founder

• What working inside Tesla, Google, and SpaceX actually taught Rama

• The hidden realities of venture capital and startup ecosystems

• Why many “prestigious” systems are far less innovative than they appear

• How moving across countries shaped his resilience and worldview

• Why confidence matters when building unconventional ideas

• The difference between hype and real innovation

• What founders misunderstand about fundraising and growth

• Why relationships matter more than credentials in business

• How Rama is building the future of orbital AI infrastructure through Satlyt

  ---

Favorite Quote

“Nothing is forever. Things fall apart.”

—Inspired by Things Fall Apart by Chinua Achebe

Favorite Book

📖 Things Fall Apart - Chinua Achebe

In This Episode

(00:00) Who Rama is beyond the résumé

(04:00) Growing up across Kenya, Botswana, South Africa, Europe, and the U.S.

(08:00) How movement and adversity shaped his mindset

(12:00) Early entrepreneurship and learning hard lessons about venture capital

(18:00) Working at Tesla Africa and building telecommunications infrastructure

(22:00) The reality of Google culture and leadership

(28:00) Why he joined — and left — SpaceX

(34:00) The origin story behind Satlight

(40:00) Orbital data centers, AI, and the future of space infrastructure

(46:00) Fundraising, startup pressure, and founder psychology

(50:00) Identity, race, and building confidence from within

(54:00) Leadership, ambition, and defining success on your own terms

Referenced in This Episode

• Venture capital and startup ecosystems

• Orbital computing and AI infrastructure

• Identity, race, and cultural belonging

• Founder psychology and resilience

New episodes drop every Monday and Thursday.

Be Bold. Be Real. Be Anomalous.

Follow for more Be Anomalous stories, conversations, and behind-the-scenes.

Website | Instagram | LinkedIn | YouTube | @iamsaimenon

Episode Description

In this episode of Be Anomalous, Julie Castro Abrams joins me for a conversation about power, identity, and what it actually means to build a life rooted in values, not validation.

Julie isn’t just a venture capitalist.
She’s a social worker at her core. A systems thinker. A builder of ecosystems that weren’t designed for women and definitely not for women who don’t play by the rules.

But the most important thing about Julie isn’t what she’s built.
It’s why she built it.

She grew up believing her life should be in service of others, not in theory, but in action. That belief shaped everything: her career in social impact, her decision to study inequality, and the way she’s navigated power in rooms that weren’t built for her voice.

But this conversation goes deeper than credentials.

We talk about identity not as a label, but as something you constantly shed and rebuild.
We talk about privilege, not as guilt, but as responsibility.
And we talk about what it means to lead without losing your humanity.

Julie also shares what she’s seen behind closed doors — in boardrooms, in fundraising conversations, and inside the systems that quietly decide who gets funded… and who gets overlooked.

And then we get real about the things no one teaches you:

How power actually works
Why women are still playing a game that wasn’t designed for them
And what it takes to build something when the odds — and the system — aren’t in your favor

This episode isn’t just about business.
It’s about self-awareness. Courage. And choosing to lead differently.

If you’ve ever felt like you don’t belong in the rooms you’re trying to enter…
This conversation will challenge you to stop asking for permission — and start redefining the room itself.

🎧 Listen to the Episode

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

• Why identity isn’t fixed and how to consciously redefine it

• The difference between power, privilege, and responsibility

• What’s really happening in fundraising rooms (that no one says out loud)

• Why are women asked different questions than men, and how does it impact outcomes

• The hidden risks of choosing the wrong co-founder

• Why emotional resilience matters more than intelligence in building a company

• How to build a team when you can’t compete on salary

• The truth about imposter syndrome, even at the highest levels

• Why success without alignment leads to burnout

Favorite Quote

“When you let your light shine, you unwittingly give others permission to do the same.”— Marianne Williamson

Favorite Book

📖 Forces for Good — Leslie Crutchfield & Heather McLeod Grant

📖 The Founder’s Dilemmas— Noam Wasserman & Mark Mosely

In This Episode

(00:00) Who Julie is beyond her resume

(04:00) Growing up with purpose and choosing a life of service

(08:00) Power, privilege, and what most people misunderstand

(12:00) Living between identities — culture, race, and belonging

(18:00) Women, power, and surviving in male-dominated spaces

(24:00) The reality of bias in fundraising

(30:00) Why many founders fail before they even start

(36:00) Co-founder mistakes that can destroy companies

(42:00) What actually makes a successful founder

(48:00) Hiring, firing, and leading with clarity

(52:00) Redefining success at different stages of life

(54:00) Why women need to be investing, not just building

(56:00) Final reflections on leadership, visibility, and impact

Referenced in This Episode

• Venture capital and funding bias

• Women in leadership and boardrooms

• Identity, code-switching, and cultural navigation

• Startup building and founder dynamics

• Power structures and systemic inequality

• Mental health and high-performance environments

New episodes drop every Monday and Thursday.

Be Bold. Be Real. Be Anomalous.

Follow for more Be Anomalous stories, conversations, and behind-the-scenes.

Website | Instagram | LinkedIn | YouTube | @iamsaimenon

In this episode of Be Anomalous, I sit down with Mitali, the founder of Fashom and XFashom, two ventures that bridge fashion, technology, and sustainability. Her path is anything but traditional: from growing up in Oman and Saudi Arabia, to studying engineering in Florida, to leaping headfirst into the fashion industry in New York. Along the way, she’s built platforms that celebrate real women, real bodies, and real style long before “body positivity” was a marketing trend.

We talk about the cultural whiplash of moving from Saudi Arabia to the U.S., the loneliness of being a woman in male-dominated industries (both engineering and tech), and what it takes to raise money when investors tell you, “What if you spend it shopping?” Mitali shares how she turned rejection into resilience, why customer feedback is her secret weapon, and how she built not one but two companies that marry AI, style, and sustainability, all while running a nonprofit in Africa and teaching at a fashion institute.

This episode is about resilience, pivoting with purpose, and building companies that empower women without burning yourself out in the process.

If you’ve ever felt torn between safety and passion, or wondered how to balance ambition with self-care, Mitali’s story is a reminder: you can redefine success on your own terms.

🎧 Listen to the episode

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

• How Mitali went from engineering to fashion and why problem-solving, not design, has always been her superpower

• What it was like growing up in Oman and Saudi Arabia as a young woman obsessed with fashion

• How cultural constraints and reverse culture shock shaped her worldview

• The founding story of her first app, celebrating real women and unfiltered style

• Fundraising as a woman in tech: discrimination, rejection, and lessons in resilience

• Why customer feedback is the most important data point for a founder

• How YouTube unboxings (not Instagram) unlocked her first wave of traction

• Pivoting from fashion box to data-driven technology engine

• Her leadership philosophy: emotional intelligence, empathy, and mindful workplaces

• Burnout as a founder — how she rebuilt balance and why mindfulness is now a business strategy

• Building sustainable solutions for fashion waste and retailer returns

Favorite Quote

“Your world is the reflection of your state of consciousness.

— Eckhart Tolle

Favorite Book

📖 The Power of Now by Eckhart Tolle

In This Episode, We Cover:

(01:00) Mitali’s love for fashion, despite an engineering background
(02:00) The leap from engineering to entrepreneurship
(03:00) Launching her first company to showcase real bodies and unfiltered style
(04:00) Growing up in Oman and Saudi Arabia, cultural constraints and identity
(06:30) Moving to the U.S.: Florida, New York, and reverse culture shock
(07:00) Engineering as problem-solving and a foundation for entrepreneurship
(09:00) Bootstrapping vs fundraising and the sting of investor bias
(10:30) Always going back to her “why” of women’s empowerment
(11:30) Pivoting into Fashom and XFashom: AI, style boxes, and tech for retailers
(14:00) Operations lessons, returns, and building warehouse systems from scratch
(16:00) Running a nonprofit in Swaziland and teaching at Marangoni
(18:00) Burnout, mindfulness, and choosing balance over endless growth
(20:00) Emotional intelligence as the underrated skill of leadership
(22:00) Building team culture through values, wellness, and empathy
(24:00) Founder loneliness and why surrounding yourself matters
(25:00) Resilience, pivoting, and flexibility as must-have founder traits
(27:00) Customer feedback as the key to knowing when to pivot
(29:00) From a kitchen full of boxes to the first warehouse, early founder realities
(31:00) Finding traction on YouTube unboxings and reaching suburban moms
(32:00) Customer stories that remind her of her “why.”
(33:00) Sustainability goals: cutting waste and reducing returns
(34:00) Favorite book, quote, and final reflections

Referenced in This Episode

The Power of Now — Eckhart Tolle
Sarah Blakely (Spanx) — Founder inspiration
YouTube unboxings as a growth channel
Institute of Marangoni (where she teaches)

New episodes drop every Monday and Thursday.

Be bold. Be real. Be anomalous.

Follow for more Be Anomalous stories, conversations, and behind-the-scenes.

Website | Instagram | LinkedIn | YouTube | @iamsaimenon

Katherine is the founder of Francis Henri, a curated children’s clothing retailer that brings together thoughtfully selected international baby and toddler brands for the U.S. market through both brick-and-mortar stores and an online platform.

In this episode of Be Anomalous, she shares her journey from a childhood dream of becoming a wedding planner to building a career in PR at Neiman Marcus and ultimately leaping into entrepreneurship during the pandemic to create a growing retail brand.

What started as curiosity, a personal Excel list of favorite brands, and frustration with international shipping costs evolved into a business that now spans online retail and physical storefronts. Katherine’s story is one of experimentation, intuition, and learning by doing—while raising three young children.

🎧 Listen to the Episode

[Spotify] | [YouTube]

What You’ll Learn

• How Katherine turned a personal passion for kids’ fashion into Francis Henri

• Why did she start by building an Excel sheet of global baby brands before launching a business?

• How COVID unexpectedly became the catalyst for starting her company

• The transition from corporate PR at Neiman Marcus to full-time entrepreneurship

• Why she believes brick-and-mortar retail still has a powerful future

• How pop-ups validated product demand before opening stores

• The realities of bootstrapping a physical retail business

• How motherhood reshaped her priorities and decision-making as a founder

• Why hiring slowly helped her understand every part of her business

• The importance of staying lean while scaling intentionally

Favorite Quote

“Work hard and be nice to people.”

A simple but powerful principle that guides how Katherine approaches business, leadership, and life, balancing ambition with empathy and integrity.

Favorite Books

📖 The E-Myth Revisited — Michael E. Gerber

A foundational book on building systems and scaling a small business into a sustainable company.

In This Episode, We Cover

(00:00) Introduction and Katherine’s journey into Francis Henry

(05:00) Early ambition and shifting career paths

(10:00) From PR at Neiman Marcus to entrepreneurial curiosity

(15:00) The origin of Francis Henry and the Excel brand list

(20:00) Discovering international baby brands and unmet demand

(25:00) Launching online during the pandemic

(30:00) Growing through pop-ups and early customer reactions

(35:00) Why brick-and-mortar retail still matters

(40:00) Hiring, delegation, and learning to let go

(45:00) Balancing motherhood and entrepreneurship

(50:00) Bootstrapping, funding decisions, and staying lean

(55:00) Redefining success across life and business

(01:00:00) Final reflections and advice for founders

Referenced in This Episode

• Building Francis Henri from online to brick-and-mortar retail

• Entrepreneurship during COVID and business resilience

• Multi-brand retail strategy in children’s fashion

• Bootstrapping vs. fundraising decisions

• Hiring, delegation, and early-stage team building

• Work-life balance as a founder and mother of three

• The future of in-person retail experiences

• Global sourcing of children’s clothing brands

New episodes drop every Monday and Thursday.

Be bold. Be real. Be anomalous.

Follow for more Be Anomalous stories, conversations, and behind-the-scenes.

Instagram | LinkedIn | YouTube | @iamsaimenon

Episode Description

In this episode of Be Anomalous, Shahezad joins me for a conversation about reinvention, risk, and what it really looks like to build something from the ground up without a blueprint.

Shahezad is the founder of Cousins Burger, a fast-growing restaurant brand that started from a single, reluctant decision to show up at a food festival.

Today, it’s a multi-location business generating millions in revenue.

But what makes this story interesting isn’t just the growth.

It’s how unexpected it all was.

Shahezad spent over two decades in IT, building a stable, predictable career. Entrepreneurship was never the plan. In fact, growing up, he was told he wouldn’t succeed in business at all.

And for a long time, he believed it.

But over the years, through small wins, moments of curiosity, and experiences that quietly built his confidence, that narrative began to shift.

Until one day, he decided to try something different.

What followed wasn’t a perfectly planned transition. It was messy, uncertain, and filled with moments of doubt.

From figuring out how to cook at scale, to managing teams, to learning how to build a brand through storytelling and social media—Shahezad built Cousins Burger in real time.

And he did it differently.

Instead of chasing rapid growth, he focused on building intentionally.

Instead of following industry norms, he leaned into creativity, community, and culture.

And instead of optimizing just for profit, he started redefining what success actually meant to him.

This conversation goes beyond restaurants.

We talk about fear, identity, scaling, and the tension between comfort and ambition.

Shahezad also shares how he’s using storytelling and AI to build his brand, why he’s selective about growth, and what it takes to build something that actually lasts.

This episode is for anyone who’s ever felt like they were starting late…

or questioning whether they’re “cut out” for something more.

If you’ve ever stood at the edge of a decision and wondered if you should leap,

This conversation is your reminder that you don’t need certainty to begin.

🎧Listen to the Episode

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

• Why Shahezad left a 24-year IT career to start Cousins Burger

• How a single food festival turned into a multi-million dollar business

• The concept of “golden handcuffs” and why it’s hard to walk away

• How to scale a business without losing quality or control

• Why storytelling is one of the most powerful tools in business

• How Shahezad is using AI to create content and grow his brand

• The importance of choosing the right partners and team

• Why success isn’t just about money—and how that mindset shifts over time

Favorite Quote

“A bird does not worry about the branch underneath it breaking… because it trusts in the strength of its wings.”

A reminder that real security doesn’t come from what you hold onto, it comes from what you’re capable of building.

Favorite Books

📖 Roald Dahl collection

📖 The Da Vinci Code — Dan Brown

Stories that shaped imagination, curiosity, and a love for storytelling.

In This Episode, We Cover

(00:00) Introduction and Shahezad’s unexpected journey

(05:00) Growing up with limiting beliefs about entrepreneurship

(10:00) The food festival that started at Cousins Burger

(15:00) Early challenges and learning the business from scratch

(25:00) Scaling the brand and building the right team

(35:00) Using storytelling and AI in marketing

(45:00) Redefining success beyond money

(50:00) Lessons on growth, risk, and decision-making

(55:00) Final reflections and advice for builders

Referenced in This Episode

Cousins Burger and restaurant scaling

Entrepreneurship and career pivots

Storytelling in business and brand building

AI in content creation and marketing

Partnerships, hiring, and team building

Redefining success and long-term vision

New episodes drop every Monday and Thursday.

Be bold. Be real. Be anomalous.

Episode Description

In this episode of Be Anomalous, Melissa joins me for a conversation about identity, motherhood, and what it really looks like to build a company that challenges an entire industry.

Melissa is the founder of a K-beauty brand designed specifically for melanin-rich skin, but what she’s building goes far beyond skincare.

It’s about representation, science, and rewriting who beauty is actually for.

But the way she arrived here wasn’t linear.

Melissa grew up between cultures, Caribbean, Italian, and French, moving across countries and learning to adapt to different environments from a young age. That exposure shaped her curiosity, her worldview, and ultimately her ability to bridge gaps that most people don’t even see.

She started her career in high fashion, working closely with brands, models, and creatives. From there, she launched her first startup in swimwear, learning the realities of building a business from scratch, from sales to logistics to partnerships.

After stepping away and going back to school to sharpen her business skills, Melissa began connecting the dots that would eventually lead to her current company.

It started with a realization:

K-beauty, one of the most innovative industries in the world, wasn’t built with melanin-rich skin in mind.

And then it became personal. When her daughter told her, “I’m not pretty because I’m brown,” everything changed.

That moment became the foundation of what she’s building today. But this conversation goes far beyond beauty.

We talk about what it means to build something rooted in purpose, the realities of fundraising, and how to navigate entrepreneurship while raising a family.

Melissa also shares how she approached product development from a scientific perspective, why she chose to work directly with Korean labs and the government, and what it takes to build credibility in an industry that wasn’t designed for you.

This episode is for anyone building something that challenges the norm — especially if you’ve ever felt overlooked by the very systems you’re trying to enter.

If you’ve ever questioned whether an industry was built for you… This conversation is a reminder that sometimes the answer is to build your own.

🎧 Listen to the Episode

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

• Why K-beauty hasn’t historically worked for melanin-rich skin

• The science behind skin differences and why “one-size-fits-all” products fail

• How Melissa validated a global market gap before building her brand

• What it really takes to fundraise in a competitive, saturated industry

• The importance of representation in both branding and product development

• How to build a team that truly understands your customer

• Why being close to your market matters more than online data

• The reality of balancing entrepreneurship and motherhood

Favorite Quote

“You can have everything — but not at the same time.”

—Betty Friedan

A powerful reminder that balance isn’t about doing everything at once, it’s about being intentional with where your energy goes in each season.

Favorite Book

📖 Pachinko — Min Jin Lee

A deeply moving story that follows generations of a Korean family, exploring resilience, identity, and the strength of women who carry everything forward.

In This Episode, We Cover

(00:00) Melissa’s identity beyond work and growing up between cultures

(05:00) Discovering K-beauty and realizing the gap for darker skin tones

(10:00) The moment her daughter said, “I’m not pretty because I’m brown.”

(15:00) Building a brand rooted in science, not just marketing

(20:00) Why representation in beauty still falls short

(25:00) Lessons from her first startup and learning business the hard way

(30:00) Building the right team and choosing the right co-founder

(35:00) Moving to Korea and working with labs + the government

(40:00) Understanding where customers actually shop and how they behave

(45:00) Fundraising, strategy, and building in a saturated market

(50:00) Balancing entrepreneurship, motherhood, and personal life

(55:00) Final reflections on purpose, impact, and building for the next generation

Referenced in This Episode

K-beauty and global beauty standards

Melanin-rich skin and dermatology insights

Startup fundraising and early-stage strategy

Building a beauty brand from scratch

Representation in consumer brands

Entrepreneurship and motherhood

Global market expansion and cultural positioning

New episodes drop every Monday and Thursday.

Be Bold. Be Real. Be Anomalous.

Episode Description

In this episode of Be Anomalous, Priya Ravindra joins me for a conversation about curiosity, self-belief, and building a business rooted in values in a world that often rewards speed over intention.

Priya’s journey is anything but linear.

She grew up in India, shaped by strong women, deep-rooted values around fairness, and an early belief that speaking up wasn’t optional. As a teenager, she moved to Australia to study engineering, eventually finding herself in tech as one of the only women coding in the room.

But the company she’s building today didn’t begin in tech.

It began with a question.

During the pandemic, as consumption skyrocketed, Priya found herself wondering: Where does all of this go? What happens to the clothes we buy, wear, and discard?

That curiosity led her down a path into textile waste, sustainability, and eventually into building Punar, an ethical brand working with recycled materials, conscious production, and a mission to rethink how we consume.

But this conversation goes far beyond sustainability.

We talk about growing up between cultures, navigating gender inequality across countries, the realities of building a business from scratch, and why visibility and speaking up are essential, especially for women founders.

Priya also shares the behind-the-scenes of entrepreneurship, the failed samples, delayed shipments, self-doubt, and the resilience it takes to keep going when nothing is guaranteed.

This episode is for founders, builders, and anyone trying to follow a path that doesn’t come with a clear blueprint.

If you’ve ever felt pulled toward something you couldn’t fully explain yet, this conversation is for you.

🎧 Listen to the Episode:

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

• How curiosity can turn into a business

• Why self-belief is built through action, not confidence

• The realities of building a sustainable brand from scratch

• How to navigate being the only woman in male-dominated spaces

• Why speaking about your work is not ego, it’s a responsibility

• How flexibility in execution can unlock unexpected opportunities

• The importance of community and “finding your tribe” as a founder

• Why ethical and sustainable businesses require both conviction and strategy

Favorite Quote

“Everything you seek is inside of you.”

A reminder that the answers, the clarity, and the direction we’re searching for externally often already exist within us — if we’re willing to trust it.

Favorite Book

📖 Atomic Habits — James Clear

A powerful framework for understanding how small, consistent actions compound over time — and how real transformation doesn’t come from drastic change, but from steady, intentional shifts.

In This Episode, We Cover

• (00:00) Introduction and Priya’s early life in India

• (05:00) Moving to Australia and entering engineering

• (10:00) Being one of the only women in tech

• (15:00) Understanding gender inequality as a global issue

• (22:00) The curiosity that led to sustainability

• (30:00) Starting Punar and learning textiles from scratch

• (38:00) Early failures, product development, and persistence

• (45:00) Building a brand through storytelling and community

• (52:00) From B2C to B2B — evolving the business model

• (58:00) Sales, visibility, and speaking up as a founder

• (01:05:00) Mistakes, delays, and learning resilience

• (01:12:00) Advice for founders building unconventional paths

Referenced in This Episode

• Sustainable fashion and textile waste

• Ethical production and circular design

• Gender inequality in tech and entrepreneurship

• Founder mindset and resilience

• Building mission-driven brands

• Community and collaboration in business

Resources Priya Mentioned in This Episode

• United Nations Sustainable Development Goals (SDGs)

• Founder communities and women-led business networks

New episodes drop every Monday and Thursday.

Be Bold. Be Real. Be Anomalous.

In this episode of Be Anomalous, Natalie Trotta joins me for a conversation about nonlinear careers, curiosity, and what it really looks like to build a path that doesn’t follow a script.

Natalie describes herself as someone who translates strategy into action — helping founders and leadership teams take the ideas in their heads and turn them into something real.

But the way she arrived there wasn’t linear.

Natalie grew up in Ohio and knew from a young age that she wanted to build a life in New York. That intuition eventually led her to Pace University in the financial district, where she began building a career across multiple industries.

Over the past decade, she has worked across fashion, beauty, tech startups, neuroscience research, climate initiatives, and higher education, gaining a rare perspective on how different industries operate and how innovation actually moves from idea to reality.

After completing her MBA at Columbia Business School, Natalie eventually launched her own consulting practice, working with founders and emerging brands to turn big visions into executable strategies.

But this conversation goes far beyond career milestones.

We talk about curiosity as a career compass, the power of staying in motion when you don’t yet know the destination, and how working across industries can become one of your greatest strategic advantages.

Natalie also shares the practical systems she uses to run her consulting business, how she structures her days to stay productive when no one is managing her time, and why quitting the wrong things can be essential to focusing on what truly matters.

This episode is for anyone navigating career uncertainty, exploring entrepreneurship, or trying to figure out how to turn their ideas into something real.

If you’ve ever felt pressure to follow a traditional career path, this conversation is a powerful reminder that the most interesting careers are often the least linear.

🎧 Listen to the Episode

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

• Why nonlinear careers can become a strategic advantage

• How to translate big ideas into real execution

• The real value of an MBA and when it makes sense

• How Natalie built her consulting business through relationships and network

• Practical systems for managing your time when you work for yourself

• Why curiosity can be a better career guide than rigid planning

• How founders can stay resilient when things don’t go as planned

• Why quitting the wrong things can unlock real progress

Favorite Quote

“People will forget what you said, people will forget what you did, but people will never forget how you made them feel.”

— Maya Angelou

A powerful reminder that impact often has less to do with titles or achievements and more to do with how we show up for others.

Favorite Books

📖 Quit — Annie Duke

A compelling exploration of why strategic quitting is often necessary for meaningful progress.

📖 Big Magic — Elizabeth Gilbert

A thoughtful look at creativity, courage, and learning to follow curiosity without fear.

📖 10x Is Easier Than 2x — Benjamin Hardy & Dan Sullivan

A counterintuitive approach to growth that challenges how we think about scaling work and ambition.

In This Episode, We Cover

(00:00) Introduction and Natalie’s early ambition to move to New York

(05:00) Growing up in Ohio and building independence early

(10:00) Internships, early career exploration, and learning across industries

(16:00) Moving from fashion and beauty into tech and innovation

(20:00) Why Natalie decided to pursue an MBA at Columbia

(28:00) Lessons from business school and building a powerful network

(32:00) Starting a consulting practice and formalizing the business

(36:00) Systems for productivity and time management as a founder

(42:00) Working with founders and translating strategy into action

(47:00) Reframing failure and learning from uncertainty

(50:00) Advice for anyone trying to figure out their next step

Referenced in This Episode

• Consulting and founder strategy

• MBA career paths and executive education

• Startup and founder productivity systems

• Career pivots across industries

• Building a consulting business

• Time management for entrepreneurs

New episodes drop every Monday and Thursday.

Be Bold. Be Real. Be Anomalous.

In this episode of Be Anomalous, Shai Basys joins me for a conversation about empathy, leadership, and how some of the most meaningful companies begin with deeply personal problems.

Shai’s path is anything but conventional.

She began her career as one of the youngest U.S. diplomats, representing the United States overseas in her early twenties. Her work took her across countries and cultures, navigating complex political environments while learning how systems operate on a global scale.

But the company she’s building today didn’t begin in diplomacy.

It began much closer to home.

When someone in her family lost access to critical healthcare services, Shai experienced firsthand how difficult it can be to navigate the systems meant to provide care. What started as an attempt to solve a personal problem quickly revealed something much larger: a structural issue affecting providers, families, and patients across the healthcare system.

That experience eventually led her to build Carelumi, a company focused on automating insurance credentialing for healthcare providers so they can get approved faster and help more patients access care.

But this conversation goes far beyond startups.

We talk about growing up between cultures, the complexity of representing your country abroad, navigating leadership at a young age, and how empathy can become a founder’s greatest advantage.

Shai also shares her perspective on the future of AI, what it can automate, what it can’t replace, and why human judgment, ethics, and philosophy may become some of the most important skills in the years ahead.

This episode is for founders, builders, and anyone trying to turn lived experience into meaningful work.

If you’ve ever wondered how personal moments shape professional paths, or how empathy can become a strategic advantage, this conversation is for you.

🎧 Listen to the Episode:

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

• Why empathy can be a founder’s greatest advantage

• What working as one of the youngest U.S. diplomats teaches you about leadership

• How navigating autism care for a family member revealed a broken healthcare system

• How personal problems can reveal massive market opportunities

• Why navigating broken systems often leads to innovation

• How cross-cultural experiences shape leadership and communication

• What founders should understand about AI and the future of work

• Why philosophy and ethics may become essential skills in an AI-driven world

Favorite Quote

“Your vibe attracts your tribe.”

A simple reminder that the energy you bring into the world, the way you think, lead, and build, shapes the people who choose to join you.

Favorite Book

📖 Parable of the Sower — Octavia E. Butler

A powerful novel about change, resilience, and shaping the future in uncertain times, a theme that resonates strongly in today’s rapidly evolving world.

In This Episode, We Cover

(00:00) Introduction and Shai’s journey into diplomacy

(05:00) Becoming one of the youngest U.S. diplomats

(12:00) Representing the United States abroad

(20:00) Leadership and navigating authority at a young age

(28:00) Leaving diplomacy and exploring new paths

(35:00) A personal healthcare challenge that changed everything

(42:00) Building Carelumi and solving credentialing problems

(50:00) What founders should understand about AI

(58:00) Why empathy may be the most valuable skill of the future

Referenced in This Episode

• Healthcare credentialing and insurance systems

• AI and automation in healthcare

• Cross-cultural leadership

• Founder of empathy and lived experience

• The future of work in an AI-driven world

• Building companies from personal problems

Resources Shai Mentioned in This Episode

• 80k hours is a fantastic resource, especially for anyone looking for non-technical careers in AI:

• U.S. diplomat career tracks

• Perplexity Comet Link

• Gemini Pro (free for students)

• Granola AI Meeting Notes

• Vercel (alternative to Lovable)

• 11Labs (amazing if anyone is interested in building voice agents)

• HeyGen (next level if you want to create a digital twin or give your voice agent a face)

New episodes drop every Monday and Tuesday.

Be Bold. Be Real. Be Anomalous.