This is the story of a girl who grew up with no fixed address and no one telling her what she was allowed to become, and who spent the next seventy years finding out.

She was born Gloria Marie Steinem on March 25, 1934, in Toledo, Ohio, to a father who sold antiques out of the back of a house trailer and a mother who had once been a real journalist herself, writing under a man’s byline because that was the only way a newspaper would run her work. For years the family didn’t live anywhere so much as move through places, winters in Florida or California chasing whatever the trailer could sell, summers back in Ohio. There wasn’t much regular schooling in those years. There were books, though, stacks of them, read indiscriminately by a kid nobody was supervising closely enough to stop her.

Then, when Gloria was ten, her parents split. Her father drove off to keep chasing sales. Her mother, worn down by years of instability and what would now likely be recognized as untreated mental illness, could no longer really function as an adult in charge of a household. So a ten-year-old ran the household instead. Gloria cooked and managed money. She sat with her mother through nights when her mother believed people were coming to hurt them. It was not a childhood built for confidence. It was a childhood that taught her, early, what it looks like when a woman’s ambitions get quietly erased by circumstance a lesson she wouldn’t have language for until much later, but never stopped carrying.

She got out the way a certain kind of determined, bookish kid from a broken household sometimes does: by being good enough at something to leave. She finished high school living with her older sister in Washington, D.C., got into Smith College, and graduated in 1956 with a degree in government. Then, instead of doing what a young woman with a good degree was supposed to do next, she used a fellowship to disappear to India for two years.

In India, she fell in with local organizers running grassroots campaigns against caste violence, walking village to village, building support one conversation at a time rather than waiting for permission from anyone above them. Nobody there had institutional power. They built power anyway, out of persistence and presence. Steinem watched how it worked and filed the lesson away without knowing yet what she’d use it for.

Birth Of An Icon: A Bunny Tale

Back in New York, trying to break in as a serious journalist, she ran straight into a wall built entirely out of what editors assumed a woman writer was good for: stockings, hairstyles, dating advice. Real political reporting simply wasn’t offered to her. In 1963, chasing an assignment that might finally prove otherwise, she agreed to something almost nobody else would touch: going undercover, under a fabricated identity, as a Playboy Bunny at Hugh Hefner’s flagship New York club, to find out what the job actually did to the women inside it. She lasted eleven days in a costume so tight she could barely breathe, endured mandatory physicals and a demerit system designed to keep the women compliant, and came out with a two-part exposé that forced real changes at the clubs. It also, for a long stretch of years afterward, nearly buried her as a serious writer; editors couldn’t see past “the Bunny girl” to the reporter underneath. She turned down the money that would have let her cash in on the notoriety and kept fighting for the assignments she actually wanted. It took years to be taken seriously again.

The turn that mattered most arrived almost by accident, in 1969, at a meeting she’d only gone to as a reporter. It was a gathering of a radical feminist group, and Steinem went planning to cover it the way journalists are trained to, from a careful, professional distance. Instead, listening to women describe experiences that suddenly sounded exactly like her own life, something in her rearranged. The essay she wrote afterward, “After Black Power, Women’s Liberation,” wasn’t reporting from outside a movement. It was her stepping into one, in print, under her own name, for the first time.

A Revolution Was Born

From there, she stopped being only a writer and started being a builder. In 1971 she helped found the National Women’s Political Caucus alongside Bella Abzug, Shirley Chisholm, and Betty Friedan, an organization built to get women into elected office. That same year, with a community organizer named Dorothy Pitman Hughes, she co-founded the Women’s Action Alliance and began touring the country with her speaking on campuses and in church basements about a movement most of the press had already decided was a complaint for bored, comfortable, white women. Pitman Hughes, standing beside her, made that story impossible to hold onto.

What began as an idea for a fundraising newsletter turned, over months of arguing and organizing with a small group of women editors, into something much bigger: a national magazine about women’s actual lives, controlled by women, answering to no one else’s idea of what belonged in it. Nobody thought it would work. There had never been anything quite like it. The money that got it off the ground was an unlikely patchwork of small checks from friends, seed funding from a newspaper publisher, a bigger investment from a media company betting on something it didn’t fully understand. When the preview issue of Ms. hit newsstands at the end of 1971, tucked inside another magazine with no advertising budget of its own, the editors braced for it to sit for months. It sold out its entire run nationwide in eight days.

Keeping Ms. alive took nearly twenty years of a harder fight: advertisers who didn’t believe women decided what to buy, sponsors who demanded control over what ran near their ads, years when the staff genuinely didn’t know if payroll would clear. In 1989, the money finally ran out, and the magazine went dark. Instead of chasing a rescue on someone else’s terms, Steinem and the team made a different bet: when Ms. came back seven months later, it carried no advertising at all, funded instead by readers willing to pay more for a magazine that wouldn’t compromise. It worked. The magazine survived on exactly the terms it had been built for.

Her Legacy Continues.

She kept building for decades after that: the Ms. Foundation for Women, Take Our Daughters to Work Day, the Women’s Media Center in 2005, founded well into her seventies alongside Jane Fonda and Robin Morgan. She wrote books, including Revolution from Within, which argued that believing in your own worth wasn’t vanity but the actual foundation of any real fight for change.

In 2013, President Obama gave her the Presidential Medal of Freedom, telling the room how much of the way the country talked about equality had been shaped by her work.

She married once, in 2000, to a British-born entrepreneur named David Bale, and cared for him through the illness that killed him three years later. She never had children of her own, though she often said the movement had given her something like a very large, complicated family.

Gloria Steinem died on September 2, 2026, at her home in New York City, at the age of 92. Her foundation said she’d spent her final years doing the two things she loved most: sitting in conversation with people, and writing. She never stopped working for the world she believed in.

A memoir she’d finished, An Unexpected Life, arrives in bookstores later this month.

She started with no stable home, no institutional backing, and no proof that any of it would work. What she had instead was a willingness to keep showing up, in a Playboy Club she had every reason to walk out of, in a movement meeting she only meant to cover, in a magazine office where the lights nearly went out more than once, until showing up turned into something that outlasted her.

New article every Thursday.

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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

New episodes drop every Tuesday.

Be Bold. Be Real. Be Anomalous.

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

Let me tell you a story.

There were two farmers. Both planted their seeds at the same time. Both worked their land every single day. Early mornings, long hours, hands in the soil, showing up without fail.

But one farmer was obsessed with his neighbor’s field.

Every morning, before tending to his own crops, he would walk to the fence and look over. Was his neighbor’s field growing faster? Were his crops fuller? Was the rain falling more on his side? And every time he saw his neighbor thriving, he felt that quiet, uncomfortable sting. Because in his mind he was the better farmer. He worked harder. He was more honest. He treated his land with more care. So why was his neighbor doing just as well? Maybe even better?

And so he kept watching. Kept comparing. Kept waiting for the universe to make it make sense.

Meanwhile, his own field, the one he was supposed to be tending, was growing. Quietly. Slowly. Doing exactly what it was supposed to do. But he was too busy looking over the fence to notice.

The second farmer never looked up.

He just planted. Watered. Showed up. Day after day after day. Not because he was guaranteed a good harvest. Not because he believed the universe owed him one. But because this was his field. His work. His life. And that was enough.

I was the first farmer this week.

Something got under my skin. Someone else’s success was bothering me in a way I couldn’t shake. And when I finally got quiet enough to ask myself why really why what I found was uncomfortable to admit.

I had attached success to being a good person.

Deep down, I believed that if you do the right thing, if you stand up for what is right, show up with integrity, try to be good, life rewards you for it. And people who don’t? They get what they deserve eventually.

But life doesn’t work that way. And when someone I felt had acted wrongly seemed to be thriving, my whole equation fell apart. And what I felt wasn’t just discomfort. It was the particular sting of someone who expected fairness and didn’t get it.

That was the real thing. Not their success. My broken equation.

Because success is not a moral report card; good people struggle every day. People who cut corners get ahead. Life doesn't keep score the way we want it to. And if your peace depends on that scorecard, you will spend so much of your life at the fence. Watching. Waiting. Quietly resenting. While your own field grows untended.

So here is what I am taking into this week.

Tend your field. Every single day. Not because you are guaranteed a good harvest. Not because you are waiting for the universe to reward you for being good. But because it is your field. Your work. Your life.

Be good because it is who you are. Do the work because it matters to you. Stand up for what you believe in because you believe in it, not because you expect something in return.

And stop looking over the fence.

Your harvest is growing. You just have to show up for it.

Let’s have a great week.

What Else Dropped This Week

Off Script

The Unconventional Path to Business Strategy — Dr. James Richardson on CPG, Growth & Being an Outsider

Under the Hood

David Senra - The Man Who Built an Empire on a Six-Year Paywall Nobody Wanted

What I’m Reading

Caste: The Origins of Our Discontents -Isabel Wilkerson

This book made me question how much of who we become is truly ours, and how much is shaped by the systems we’re born into.

Start with Yourself - Emma Grede (Finishing)

A practical guide to taking ownership, building influence, and creating opportunities.

Things That Happened Around

1. Apple’s Ternus Takes the Reins as CEO, With AI as Job No. 1

2. Why Silicon Valley’s Vision of the AI Future Should Worry You

3. A $2 Hot Dog Explains the Human Advantage Every Company Will Need as Automation Spreads

4. What’s Behind India’s Next Era of Growth

5. The New Map of AI Power

Note to Self

Your work is compounding every single day you show up. You may not see it yet. But it is happening. The bamboo grows underground for years before it breaks through the surface, and when it does, it shoots up fast. That is your work. That is your field.

But only if you are tending it.

Stop watching someone else’s harvest. You might just miss your own.

Be bold. Be real. Be Anomalous.

— Sai Menon

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

In 2010, a friend dragged David Senra over to watch Joe Rogan’s show on a scrappy livestreaming service called Ustream. Senra wasn’t a media guy. He wasn’t chasing a platform or a following. He just sat there and had the thought that would eventually rearrange his entire life: he could listen to something this raw, this long, this unfiltered, whenever he wanted, from his phone. It rewired something in him. Six years and several failed businesses later, that couch-side revelation became a podcast recorded alone in a Miami kitchen, with a hundred-dollar microphone and absolutely no plan for how it would ever make money.

Every Business Before This One Was a Test Run

Senra had been starting businesses since he was eighteen, detailing cars and boats, then a company called RoboDB that tracked the origin of robocalls. None of it failed. He was pulling in what he called “dentist or doctor money,” comfortable, unremarkable, the kind of income that quiets people down instead of pushing them forward. But nothing he built held his attention the way a good biography did, and it never had, not since he was a kid discovering there was nowhere quite as absorbing as someone else’s whole life laid out on a page.

That restlessness matters, because it explains why Senra didn’t wait for permission or a market signal before he started Founders. He’d already spent a decade proving to himself he could build things that worked financially and still felt hollow. What he was chasing wasn’t a bigger business but a one that he cared enough to know the result didn’t matter.

The Debt Nobody Talks About

Senra’s grandfather was not an educated man. He worked as a butcher, then in a factory that made shoes or socks; even Senra isn’t sure which anymore. In 1959, in his late thirties, married, with a newborn son who would grow up to be David’s father, he watched Castro take over Cuba and made a decision: leave, with no English, no money, and no education, and start over in a country that owed him nothing.

Senra has said, without flinching, that the family that followed wasn’t an easy one to grow up in. He was the first person in his family to graduate high school, the first to graduate college, and in his own words, “the first male in my family not to go to prison in three generations.” He worked full-time during the day and went to the University of Central Florida at night, because that was the only way he could go to college.

Built With No Producer, Paid For By No One

Founders launched in 2016 with no team, no distribution deal, and no safety net. Senra did and still does every part of it himself: choosing the biography, reading it with a pen and a six-inch ruler, marking the pages that mattered, sitting alone in a room, and recording his thoughts out loud. He hosted the show through a small distribution partner called Colossus and made an unusual bet on the business model: the first thirty minutes of every episode were free, and the rest sat behind a paywall.

He kept that structure for six years. Six years of turning away casual listeners at the exact moment they might have gotten hooked, because he believed the work itself had to be worth paying for before he’d let it be free. It was, by any conventional startup logic, a strange way to try to grow. It also meant that the audience he did build in those years wasn’t casual. It was people who’d decided, thirty minutes in, that this was worth their money.

Underneath the recording schedule was discipline. By his three-hundredth episode, Senra had read more than three hundred biographies over a hundred thousand pages and logged every meaningful passage into a reading app called Readwise. He started pulling the sharpest lines from his research and posting them on social media, not as marketing, but as an extension of the reading itself. Those quotes became the thing that pulled strangers toward the show years before most of them ever pressed play on an episode.

The Tweet That Did What No Ad Budget Could

Growth stayed slow and word-of-mouth for years. Then, one May, Patrick Bet-David, a business podcaster with real reach, posted that he never finds new shows worth recommending, except this one. Senra knew Bet-David only in passing. A mutual friend, the former NBA executive Sam Hinkie, connected them properly, and the two hit it off immediately over a shared obsession with entrepreneurship and history. Bet-David didn’t just mention the show once. He kept sending people to it. So did Rob Moore. So did Andrew Huberman, whose own show would go on to dwarf most podcasts in the world.

None of them had a reason to help beyond actually believing in the work. Podcasting, as an industry, tends to reward this kind of unpaid generosity between hosts, and Senra’s growth curve is a direct product of people who owed him nothing choosing to talk about him anyway. By the time listener counts were being seriously tracked, Founders was pulling well over a hundred thousand unique listeners an episode, built almost entirely on people telling other people, rather than on any campaign Senra ran himself.

Choosing Ed Thorp Over the Killers

Nine years and more than four hundred biographies in, Senra has developed a theory: a lot of the most ruthlessly successful people he’s studied are miserable to be around, and often miserable to be. Instead of chasing that version of success, he’s said his real role model became Ed Thorp, the quantitative investing pioneer who made his fortune and then deliberately stopped trading time for more of it, choosing health, family, and curiosity instead. Senra has built his own life closer to that model than to the “killers” he reads about for a living: he keeps his two kids and his wife, who is Colombian, largely out of the public story, and stays rooted near her extended family in Miami rather than chasing the kind of scale that would swallow all of it.

If you had to compress everything he’s learned from nine years and four hundred lives into a single word, Senra has said, it would be focus. ( The irony is, when asked what is the one thing common in all the founders he studied, he said: focus)

Lessons from David Senra

I narrowed down the lessons from David from multiple resources so you don’t have to.

1. Study people who have already done what you want to do

You don’t have to learn everything through your own mistakes. Biographies let you study decades of someone’s decisions, failures, successes, and experiences in a fraction of the time.

Takeaway: Find people who have already achieved something you want and study how they did it.

2. Find something you genuinely care about

The people David studies tend to become deeply invested in something. They’re not simply chasing an outcome, they care about the work itself so the outcome doesn’t matter.

Takeaway: It’s much easier to sustain extraordinary effort when you actually love what you’re doing.

3. Persistence is a competitive advantage

A lot of people quit before their efforts have had enough time to compound. Staying with something for years can become an advantage because your knowledge, skills, relationships, reputation, and opportunities accumulate.

Takeaway: Before abandoning something, ask whether you’ve actually given it enough time.

4. Work extremely hard

Talent helps, but David repeatedly sees extraordinary work ethic among the people he studies.

It’s not just working long hours. It’s being willing to repeatedly do the difficult, boring, uncomfortable work that others aren’t willing to do.

Takeaway: Don’t underestimate how far sustained effort can take you.

5. Think for yourself

Many of the people David studies were willing to disagree with conventional wisdom.

They listened to other people, but ultimately made their own decisions.

Takeaway: Seek advice, but don’t outsource your judgment.

6. Focus requires saying no

You can’t pursue every interesting opportunity. Exceptional people tend to become very selective about where they put their time and attention.

Takeaway: Saying no to good opportunities can be necessary to pursue a great one.

7. Learn from failure without letting it define you

Failure appears constantly in the biographies David studies. Many successful people experienced periods where their businesses, careers, or ideas looked like complete failures.

The difference is that they treated failure as information rather than a permanent identity.

Takeaway: Ask “What did this teach me?” rather than “What does this say about me?”

8. Build before you have validation

David’s own experience with Founders demonstrates this particularly well. He continued producing the podcast for years before it became a major success.

Takeaway: Don’t require other people to believe in your idea before you’re willing to work on it.

9. Obsession can be powerful,but understand what drives it

David has noticed that some extremely successful people were fueled by insecurity, dissatisfaction, or a need to prove themselves.

That energy can produce enormous results, but it can also become unhealthy.

Takeaway: Use ambition as fuel, but eventually try to develop a genuine love for the craft rather than living permanently in a state of needing to prove yourself.

10. Don’t optimize your life only for money

David’s perspective increasingly emphasizes autonomy, ownership, and doing meaningful work, not simply maximizing income.

Money matters, but it isn’t necessarily the best measure of whether you’re winning.

Takeaway: Think about what you want your life to look like, not just your bank account.

11. Protect your attention

The people who accomplish extraordinary things tend to devote an unusual amount of attention to their primary objective.

Constantly switching between things makes deep work much harder.

Takeaway: Your attention is one of your most valuable resources. Spend it deliberately.

12. Become a lifelong learner

David’s entire career is essentially built around continuous learning. He keeps studying people, looking for patterns, questioning what he believes, and updating his understanding.

Takeaway: Don’t think of education as something that ends when school ends.

13. Look for patterns across many people’s lives

One biography can be interesting. Hundreds of biographies allow you to distinguish between one person’s story and recurring patterns.

That’s one of the unique advantages of David’s approach.

Takeaway: When you encounter an idea, don’t immediately assume it’s true. Look for whether the same pattern appears repeatedly.

14. Use history as a shortcut

Human technology changes rapidly, but human behavior changes much more slowly.

Ambition, jealousy, fear, greed, status, competition, friendship, leadership, and relationships existed long before today’s world.

Takeaway: History contains lessons that remain relevant even when the circumstances look completely different.

15. Build something that can compound

The most powerful work isn’t necessarily work that produces an immediate result.

A skill, business, audience, reputation, relationship, or body of knowledge can become more valuable over time.

Takeaway: Prefer activities where today’s work makes tomorrow’s work more valuable.

16. Your circumstances don’t determine your ceiling

The biographies David studies are full of people who started with disadvantages, failed repeatedly, or weren’t initially taken seriously.

Their starting point wasn’t necessarily predictive of where they ended up.

Takeaway: Don’t confuse your current circumstances with your permanent circumstances.

17. The goal isn’t to imitate successful people

Studying someone isn’t about copying their morning routine, personality, business model, or exact decisions.

It’s about understanding how they thought.

Takeaway: Borrow principles, then adapt them to your own circumstances.

David Senra’s story is the one of hope. You choose to do your work with all sincerity, and focus without going into the result because you enjoy it, the results will follow, if not today, not tomorrow, or maybe years later. Your time isn’t the same as anyone else’s, so keep going and believing in yourself.

New article every Thursday.

Be Bold. Be Real. Be Anomalous.

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

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

YouTube | Spotify | Apple Podcasts

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.

Be Bold. Be Real. Be Anomalous.

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

Before there was Sun Microsystems, before Kleiner Perkins, before Khosla Ventures backed the company that would become OpenAI, before any of it, there was a twenty-year-old engineering graduate in India trying to start a soy milk company. He’d noticed something simple: most people around him didn’t have refrigerators, and soybeans were cheap, plentiful protein that didn’t need one. It was a good insight. The company failed anyway. There was no funding to be found, and when he was told he’d have to wait seven years just to get a phone line installed, he did the only thing that made sense to a person who refuses to accept the world as it’s currently arranged. He left for Silicon Valley.

This is the part of Vinod Khosla’s story worth sitting with the longest. Not the venture fund that would one day help buy an NFL franchise. The failed startups that came first, and the fact that he didn’t treat it as a verdict on himself.

“Only those who dare to fail can succeed.”

No Business Connections, Just a Magazine Article

Khosla grew up in an Indian Army household in New Delhi, the kind of household where the expected path was the military, not a garage full of computer parts. He had no business or technology connections of any kind. What he had, at sixteen, was a copy of a trade magazine with a story about a new company called Intel, and a decision he made on the spot: he was going to start a technology company of his own someday. Nobody around him could have shown him how. He simply decided it was going to happen and spent the next several years figuring out the mechanics one degree at a time: a bachelor’s in Electrical Engineering from IIT Delhi, then, after the soy milk company folded, a scholarship to Carnegie Mellon for a Master’s in Biomedical Engineering.

Silicon Valley was the actual destination, though, and getting there ran through Stanford’s Business School. Twice, Stanford rejected him. The second time, an admissions officer told him bluntly that he needed real work experience. So Khosla did something almost nobody would think to do: he took two full-time jobs simultaneously for a year, manufacturing exactly the résumé line he’d been told was missing, then reapplied. Rejected Again.

The Persistence

Most people would have called that the end of the story. Khosla enrolled at Carnegie Mellon’s Business School instead and kept going. But he also, in the meantime, made a point of getting to know every single person in Stanford’s admissions office except the director who kept turning him down — learning the acceptance rates, the waitlist mechanics, all of it — and then simply refused to stop calling. The director eventually put him on the waitlist mostly, by Khosla’s own telling, to get him to stop. He didn’t stop. He called every few weeks.

Carnegie Mellon’s semester started in early September. Stanford’s started a few weeks later. In the gap between those two calendars, days before Stanford’s classes began, someone dropped out. The admissions office called Khosla. He got his spot.

It’s actually the whole operating system he’d run for the next five decades: apply, get told no, absorb exactly what the no was actually about, and come back with the specific thing that closes the gap, instead of a louder version of the same pitch.

Building the Machine, Then Walking Away From It

Khosla graduated from Stanford in 1980 and, with three classmates, Andy Bechtolsheim, Scott McNealy, and Bill Joy, founded Sun Microsystems two years later, raising $300,000 in seed money from Kleiner Perkins. As the company’s founding CEO, he helped pioneer open computing systems and the RISC processors that would reshape enterprise computing for a generation. Sun went from nothing to a billion dollars in annual sales within five years. And then, in 1984, at the moment most founders would be settling in to enjoy what they’d built, Khosla left.

He joined Kleiner Perkins as a general partner in 1986 and spent eighteen years there, backing companies like Juniper Networks and Nexgen and turning a single $3 million bet on Juniper into billions in returns for the firm. By any normal measure, this was already a full career’s worth of success. In 2004, he walked away from that too, putting roughly $1.5 billion of his own capital behind a new firm built around a philosophy most institutional investors would consider reckless: fund the “science experiments” the ideas so early, so unproven, so likely to fail, that safer money wouldn’t touch them.

The Freedom to Fail, on Purpose

Khosla Ventures backed Square, Stripe, DoorDash, Instacart, Impossible Foods, Affirm, Opendoor, and Rocket Lab in their earliest, most uncertain days. In 2018, it became the first institutional investor in a research lab called OpenAI, years before most of the world had heard the term “large language model.” The firm also poured money into fusion energy, biofuels, and dozens of clean-tech bets that never worked out, because Khosla’s whole thesis was that the wins only need to be big enough to make the failures irrelevant. “I don’t mind failing,” he’s said, “but when we succeed it has to be worth it.” By 2025, Khosla Ventures was managing roughly $16 billion, with more than 1,500 investments and nearly 200 exits.

That philosophy is easy to admire from a distance and much harder to actually live by, because it requires being genuinely at peace with being wrong, in public, over and over, on the way to being right once, enormously. Khosla has said failure doesn’t actually matter; success does. The rejected Stanford applications. The clean-tech bets that went nowhere.

None of it slowed him down, because none of it was ever treated as the final word on what he was capable of.

From a Garage Idea to the Defending Super Bowl Champions

That same appetite for the long, improbable bet is what led, this July, to a Khosla-led group agreeing to buy the Seattle Seahawks for a reported $9.612 billion, a record price for an NFL franchise, and one of the largest team purchases in the history of professional sports. The Seahawks, fresh off their second Super Bowl title, were being sold by the estate of the late Paul Allen, whose will directed that the team be sold to benefit charitable causes. Khosla’s wife, Neeru, his girlfriend since he was 16 years old and married since 1980, will serve as the team’s controlling owner, with their son Neal expected to take an active role as well. As part of the deal, the Khosla family agreed to give up its existing minority stake in the San Francisco 49ers entirely, choosing full ownership of one team over a foothold in two.

“We are honored to be entrusted as the next stewards of the Seattle Seahawks,” Khosla said on behalf of his family. “We look forward to building on the winning legacy Paul Allen created and to earning the trust of the Seahawks organization and fans everywhere.” He added, in a social media post, that he was equally glad to see the proceeds from the sale go toward charitable causes, the same instinct for building something bigger than the individual payoff that had defined the rest of his career.

What the Whole Arc Actually Says

There’s a version of this story that’s just about money: a soy milk failure turned into a $9.6 billion football team, an immaculate rags-to-riches arc. That version misses the actual mechanism. The story about a kid with no connections in a New Delhi army household to the owner’s box at Lumen Field isn’t luck, and it isn’t talent alone. It’s a specific, repeatable habit of treating every rejection as a lesson and not his fate. The Stanford admissions office, the soy milk investors, every clean-tech bet that didn’t pan out, and then coming back with something more specific than before.

If you’re in your own stretch of being told no right now, the useful thing to take from Khosla’s life isn’t “never give up,” which is true but not especially actionable. It’s closer to what he actually did at Stanford: find out exactly what the no is about, close that specific gap, and keep showing up until the math changes in your favor.

The soy milk company still failed. He got into Stanford anyway. Both things were true at once, and only one of them ended up mattering.

The work you put in will be rewarded.

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The FIFA World Cup does something to people.

It brings out a kind of passion that is hard to explain: flags everywhere, faces painted, strangers becoming family in the stands, an entire country holding its breath over a single kick. And watching it all unfold this week, one word kept coming back to me.

Patriotism.

It is a strong word. The true definition, a deep sense of love, devotion, and attachment to one’s country or homeland. Simple enough on paper. But for some of us, it is a lot more complicated than that.

My homeland is India. I am deeply rooted there, my culture, my traditions, my essence, the way I see the world. All of it traces back to India. And yet I have never lived there for more than a year. India is where I am from. It is not where I grew up.

I grew up in Oman. I built my life in the US. Three countries. Three places that have shaped me in completely different ways. I have no legal obligation to Oman or America, no passport, no citizenship, no formal ties. But I have something else. An emotional attachment that is just as real. Just as deep.

So what does patriotism mean for someone like me?

Which country do I wave the flag for?

The World Cup made me sit with that question in a way I hadn’t before. Because everyone around me was so clear about who they were rooting for. So certain. So unambiguous in their loyalty. And I found myself thinking that kind of singular belonging is something I have never quite had.

I think for immigrants, for people who have lived between worlds, who carry more than one place in their chest, patriotism doesn’t fit neatly into one country. It can’t. Because your identity was never just in one place. It was the accumulation of everywhere you have ever called home. Every culture that shaped you. Every country that left its mark on you.

My patriotism is layered. It is Indian at its roots. It is shaped by the warmth of Oman. It is expanded by the opportunity of America. All three live in me simultaneously. And I don’t think I have to choose.

But here is why this actually matters.

Because when you don’t accept it, when you resist the in-between, you live in denial.

And denial is exhausting.

It looks like spending your life waiting to go back. Holding the place you are in at arm’s length because it doesn’t feel like home. Never fully investing in where you are because somewhere in the back of your mind, you are still planning to leave. But the truth is, you chose to be where you are. And that place is giving you something. Something real enough to make you stay.

When you finally accept that when you stop fighting the in-between and start living in it, everything changes.

You stop mourning the place you are not. You start loving the place you are. You stop existing in the gap between two worlds and start owning the fact that you get to carry both. That is not a consolation prize. That is actually a gift.

The in-between is not a waiting room. It is a life. Your life.

And it is worth showing up for fully, not with one foot always pointed toward somewhere else, but with both feet planted exactly where you are.

That is the life of an immigrant. You don’t belong entirely to one place. You belong to all of them and to none of them at the same time.

Accept that. Love that. Because that is you. All of you.

And you carry the world with you. Not everyone gets to say that.

What I’m Reading

My Life in Full: Work, Family, and Our Future- Indra Nooyi (Starting)

A leadership memoir on balancing ambition, purpose, family, and long-term impact.

Start with yourself - Emma Grede (Finishing)

A practical guide to taking ownership, building influence, and creating opportunities.

Note to Self

You are not lost between worlds. You are made of them.

Accept where you are. All of it. Because the life you keep waiting to go back to and the life you are living right now — they are both yours.

Stop waiting. Start living.

Be bold. Be real. Be Anomalous.

— Sai Menon

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Most career advice assumes a ladder. Go to the right school, land at the right company, climb one rung at a time, and eventually, if everything breaks your way, you become CEO.

Fidji Simo’s career completely breaks that model.

She grew up in a small coastal town in France with no obvious route into global tech. Today she runs one of the most consequential parts of OpenAI. In between, she helped rebuild Facebook around mobile, took Instacart public as an outside CEO, and then did something most executives never do: she stepped down from the CEO seat to become an operator again. Each of those moves looked risky in the moment. Together, they trace the outline of a very different kind of career strategy, one built around proximity to what’s next, not distance climbed on a single ladder.

Starting Without a Map

Simo was born in Sète, a fishing town on France’s southern coast, where the local economy ran on boats, not startups. She was the first in her family to finish high school, a fact she’s often returned to, not as a sentimental detail but as the moment her sense of what was possible expanded.

With no built-in path into the tech world, she leaned on curiosity instead. That took her to HEC Paris for a master’s in management, and during that program, a year on exchange at UCLA gave her a first real foothold in the United States. For most students, a semester abroad is a memory. For Simo, it turned out to be the opening move of an entirely different life.

The Unglamorous Years

Her first job out of school was on eBay’s corporate strategy team, not a headline role, but a formative one. Strategy work forces you to understand a business from the inside: incentives, unit economics, customer behavior, the internal politics of how decisions actually get made and unmade.

It’s not the part of a résumé anyone highlights. It’s often the part that matters most later.

Ten Years Inside One Machine

Everything changed in scale after Simo joined Facebook in 2011. She didn’t hop between companies chasing bigger titles; she stayed put and let her responsibilities grow. Over a decade, she moved from building mobile ad products to overseeing Facebook Live and Watch, and eventually to running the entire Facebook app: News Feed, Stories, Marketplace, Groups, Gaming, Dating, Video, and Ads, the daily experience of billions of people.

That decade helped her lead to the next chapters. Speed gets celebrated in tech narratives, but Simo’s advantage came from the opposite instinct: staying long enough inside one complex system to actually understand how it worked, rather than skimming the surface of several.

Running a Company You Didn’t Build

In 2021, Simo took the harder version of the CEO job, stepping in to lead Instacart, a company she hadn’t founded, replacing Apoorva Mehta. That kind of transition comes with built-in friction: employees measure you against the founder, customers measure you against the founder, and you’re expected to protect the culture while also changing the business.

She leaned into what she’d spent a decade building: product instinct and the ability to scale. Under her leadership, Instacart grew its advertising business, pushed into AI-driven shopping tools, reached profitability, and completed its IPO. It was proof of a specific kind of leadership, the discipline of the operator who writes the next chapter.

Trading a CEO Title for a Bigger Bet

In 2025, Simo made the move that surprised the most people: she left the CEO seat at Instacart to join OpenAI. On paper, it read as a step down in title. In practice, it may have been the most deliberate decision of her career, a bet on proximity to the technology reshaping every industry, over the comfort of a title already earned.

She wasn’t arriving cold. Simo had previously served on OpenAI’s board, giving her a working understanding of the company’s strategy before she ever took an operating role there. Now, as CEO of AGI Deployment, reporting directly to Sam Altman, she oversees most of the company’s product and business machinery engineering, sales, finance, marketing, communications, policy, legal, and people. Since joining, she’s helped steer the launch of ChatGPT Health and the push to unify ChatGPT, Codex, and OpenAI’s broader tools into one coherent experience.

The easy read is that she swapped one prestigious job for another. The more accurate read: she moved toward where the next decade of technology is actually being built.

A Pause, Not an Ending

In April 2026, Simo took medical leave from OpenAI to deal with a relapse of a chronic neuroimmune condition, POTS, that she has managed for years. In July, she shared that the road to recovery was proving longer than expected and that she would not be returning to the role full-time, instead transitioning into a part-time advisory position at the company. Her responsibilities have since been distributed among other OpenAI leaders, including President Greg Brockman and CFO Sarah Friar.

What stood out in how she announced it was the candor. Simo pointed to an earlier moment in her career when Facebook offered her a full year of medical leave, and she turned it down without a second thought and said, in effect, that she’d learned the lesson too late the first time. This time, she made a different choice.

It’s a reminder that even a career built on relentless forward motion eventually has to reckon with limits that have nothing to do with ambition. Stepping back from a role of that scope, publicly and on her own terms, is its own kind of decision-making, the same instinct for knowing when to move that shaped every earlier chapter of her career, just pointed inward instead of outward.

A Career Measured Beyond the P&L

Simo’s footprint doesn’t stop at the org chart. She co-founded Women in Product, built to open up one of tech’s most influential career tracks to more women. She’s also put real weight behind biomedical research work shaped in part by her own experience with a chronic health condition and holds leadership roles supporting research into neuroimmune disorders. She also serves on Shopify’s board.

What Actually Compounds

Look past the job titles, and a clearer pattern emerges. Simo spent years going deep before she ever went broad.

That’s the real lesson underneath the résumé: titles, companies, and even entire industries shift underneath you. The thing that doesn’t depreciate is the ability to learn faster than the world around you is changing.

That’s the asset Fidji Simo has been quietly compounding the whole way through.

New article every Tuesday.

Be Bold. Be Real. Be Anomalous.

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There’s a stretch in Mira Kulkarni’s life that doesn’t show up in the headlines about her billion-dollar company. It’s not the Estée Lauder deal, not the London store, not the wedding in Jodhpur that changed everything. It’s two years, sometime after 2000, when she was working out of her home in Delhi, reformulating the same soaps and oils over and over, with no product on a single shelf and no guarantee any of it would ever leave her kitchen.

If you’re in the middle of building something right now, the version where you’ve put in real time and still have nothing to show for it, where the thing you’re making only exists in your head and a few notebooks, that’s the part of her story worth sitting with the longest. Not the acquisition. The two years before anyone had a reason to believe in her.

Starting Late, Starting Small

Kulkarni married at twenty. She’s described herself at that age as completely unaware and unexposed, a young wife who moved from Delhi to Chennai, then came back years later with two small children to raise. There was no five-year plan sitting underneath any of it. Looking back, she’s said something easy to feel but hard to say out loud: that so much of her early life passed by before she understood what she was actually capable of. “You’re in this little pond,” she said, “and you don’t know what to do.”

She didn’t leave the pond at twenty-five, or thirty, or even forty. She left it in her mid-forties, an age the startup world still quietly treats as too late, as if ambition comes with an expiration date. In 2000, with ₹2 lakh, roughly $4,500 at the time, and no outside money or safety net beyond her own conviction, she started making soaps and candles at home using coconut oil, almond oil, and ghee.

Ayurveda hadn’t been given a real chance at luxury. It had only ever been sold as medicine or sold cheaply.

She tested the idea small, low-stakes, low-cost: a home exhibition she called Candlemania, beeswax candles infused with herbs and pressed flowers, made from scratch in her own house. It sold out. That was the whole go-to-market plan: make something honest, put it in front of people, see if it lands.

The Part That Doesn’t Make It Into the Success Story

It took nearly two years of testing after that before the first real products shipped. Two years of a business that, from the outside, looked like nothing was happening. No funding round to announce. No press. No proof it was working, other than her own sense that the ghee, the sandalwood, the saffron needed to actually do what centuries of use said they could do, and that shortcutting that process would show up eventually, in a product that didn’t hold up.

This is the stretch that gets skipped over in most versions of a founder’s story, because it isn’t dramatic; it’s just quiet, uncertain, unglamorous work with no external validation. But it’s also the reason nobody could easily copy what came next. A competitor could copy an ingredient list off a label in an afternoon. Nobody could compress two years of getting the formulation right into a shortcut. If you’re in that stretch right now the invisible part, the part where you’re not sure it’s going anywhere it’s worth remembering that this is usually the part that becomes the moat later, even though it doesn’t feel like one while you’re in it.

The Hotel Order That Changed the Trajectory

The Delhi Hyatt Regency began ordering the soaps for its rooms after the property’s general manager personally requested bath essentials for the hotel. One relationship did something no advertising budget could have: it put Forest Essentials into the hands of exactly the people who could afford to buy the full-size version later, in a setting where trust already came built in.

By the time the first standalone store opened at Khan Market in Delhi in 2003, Forest Essentials wasn’t introducing itself to strangers. It had already quietly earned a reputation with the people who mattered most.

Growth from there was slow, on purpose. In 2005–2006, the company posted sales of around Rs. 6 crore, but nowhere near explosive built one category at a time: body oils, then bath essentials, then body polishes, then hair care. Kulkarni has described the model plainly: profits went back into the business, growth was slower for it, and there was no external target to hit and no funding to chase. No burn rate. No runway anxiety. Just a founder deciding the pace of her own credibility, even when slow, probably didn’t feel like a strategy; it probably just felt like reality.

A Meeting That Was Supposed to Last Thirty Minutes

In 2007, Leonard Lauder, chairman of Estée Lauder, whose mother had built the company from nothing, traveled to India for a wedding in Jodhpur and was gifted some Forest Essentials products. He was curious enough to ask his Indian country manager to look into the company. A meeting was scheduled in Delhi, meant to last thirty minutes. It ran two hours because Kulkarni and Lauder realized their founding stories rhymed two people who’d each built something out of very little, decades and an ocean apart.

A few months later, Estée Lauder took a 20% stake in Forest Essentials, its first investment in an Indian brand. It would have been easy, at that point, for Kulkarni to oversell, to dilute faster than made sense, to hand over more control than the moment required just because the offer was finally there. She didn’t. She treated the investment as fuel, not rescue. The board met twice a year to talk about long-term strategy. Estée Lauder stayed out of day-to-day operations. And the stake didn’t move again for twelve years; it stayed at 20% until 2020, when it rose to 49%. Not because anyone was hedging, but because two parties who already trusted each other felt no urgency to renegotiate something that was working.

What Nearly Three Decades of Patience Bought Her

By the time Forest Essentials was competing in India’s crowded 2020s beauty market, a landscape Kulkarni has described watching with something close to bewilderment, as thousands of new, VC-backed beauty brands appeared almost overnight, most indistinguishable from one another, the slowness had quietly become the advantage. Nearly 200 stores across India. Exports to 120 countries. A first international store in London’s Covent Garden in 2022 opened only after the brand had already proven itself online to the UK’s Indian diaspora, rather than betting everything on an untested physical launch.

And in March 2026, Estée Lauder Companies agreed to buy the remaining stake outright — the company’s first-ever full acquisition of an Indian brand, coming after eighteen years of partnership. Estée Lauder isn’t describing this as a rescue of a plateaued asset. Forest Essentials is currently ranked as the country’s top prestige skin care brand, with net sales projected to keep growing at a low double-digit rate. The acquirer’s own leadership has said the name, the pricing, the product strategy, and Kulkarni’s leadership will stay exactly as they are, with her son Samrath Bedi continuing alongside her. The brand keeps its Himalayan manufacturing base, its Ayurvedic R&D, its Indian identity intact — the things a faster-scaling, more anxious version of this company might have traded away for distribution a decade earlier.

If You’re in the Middle of the Hard Part

Here’s the thing worth carrying out of this story, if you’re in your own version of those invisible years right now: Kulkarni wasn’t rewarded for being fast. She was rewarded for being right, slowly, in a way that couldn’t be rushed or faked. She didn’t refuse help when it came; she took Estée Lauder’s investment the moment it was genuinely offered, on terms that let her keep building. The discipline was never about refusing capital or staying small out of principle. It was about not needing anything badly enough to accept it on terms that would have cost her the thing that made the whole effort worth doing.

If you’re sitting on something the world currently treats as ordinary, or cheap, or unglamorous, the question isn’t how to change to fit in. It’s what it would actually take to make the highest-quality version of it, the kind of quality that takes real time and can’t be shortcut by someone with more funding and less patience than you.

Kulkarni spent years with nothing to show anyone. Then twelve more years letting a single investor stake sit untouched, because the relationship didn’t need fixing. She was in her mid-forties when she started. She was sixty-nine when the company she built from a kitchen counter became worth a billion dollars to the people who’d once needed convincing.

The work you put in will be rewarded.

New article every Tuesday.

Be Bold. Be Real. Be Anomalous.

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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

YouTube | Spotify | Apple Podcasts

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.

Be Bold. Be Real. Be Anomalous.

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The person who fears losing the most is not the person who has nothing.

It is the person who has everything.

Think about that for a second.

When you are at the bottom, trying to climb, you are not afraid of falling. You are just focused on the next step—the next rung. The only direction that exists is up, and so that is where all your energy goes. There is a clarity in that—a kind of freedom in having nothing to protect yet.

But then you start climbing. And something shifts.

The higher you get, the more you have to lose. The more you have to lose, the more afraid you become of going back down. And suddenly, the climb that once felt like pure momentum starts to feel like something heavier. You are no longer just climbing toward something. You are also running from the thought of losing what you have already gained.

And here is the other thing.

Once you get what you were chasing, you want the next thing. The finish line moves. It always moves. So you are never really arriving anywhere. You are just chasing, gaining, fearing, chasing again. On a loop. Indefinitely.

I saw a video that made me think about how much of our lives we spend in this cycle chasing, gaining, protecting, chasing again. And I realized something sitting with it.

That is not the point.

The point is to enjoy the climb itself. To find something you love doing so much that everything else — the wins, the recognition, the results — becomes a bonus. Because if you are already happy while you are climbing, if the climb itself is the reward, then the fear of losing loosens its grip. What you gain along the way is wonderful. But it is not the source.

You are.

So ask yourself whether you are enjoying the climb? Or are you just chasing the top?

Because the top will always become the bottom of the next thing.

The climb is all there is. You might as well love it.

What I’m Reading

Crush It - Gary Vee (Reading)

I want to use this as a guide for building.

Never Split the Difference - Chris Voss(Reading)

I have been told this is a must-read for negotiating.

What Else Dropped This Week

Off Script

Why This Founder Refused VC Money & Built a Thriving Business | Susanne Mitschke

Under the Hood

The Attention Arbitrage Engine

Note to Self

Keep your blinders on.

Not because the destination is everything, but because the journey is. The climbing, the building, the figuring it out as you go. That is the achievement. Not the moment you arrive. The whole beautiful, messy, uncertain journey getting there.

Do what you love. Enjoy the climb. Let everything else be the bonus.

And when the fear of losing creeps in — and it will — remind yourself that you didn’t start this to protect what you have. You started this because something in you had to.

Keep going.

The journey is the point. It always was.

Be bold. Be real. Be Anomalous.

— Sai Menon

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Every durable consumer business is, underneath the product story, a bet on attention. Somebody spotted a place where eyeballs were gathering faster than the market had priced in, planted a flag there. At the same time, it was still cheap, and converted that audience into revenue before the competition woke up. The product gets the credit in the press release. The channel did the work.

There’s a name worth borrowing for the mechanism: attention arbitrage. Buy distribution while it’s underpriced, build an audience you actually own, convert that audience into a business, then reinvest the audience into the next bet. It’s the same logic as financial arbitrage, exploiting a gap between price and value before the gap closes, except the asset is human attention and the window is always closing. Most founders fall in love with the product and treat distribution as an afterthought. The arbitrageur inverts it, because a mediocre product on an underpriced channel beats a great product on a saturated one almost every time.

The cleanest way to see the engine is to watch one operator run it four separate times, in four unrelated categories, over twenty-five years. Gary Vaynerchuk is the obvious specimen, not because he’s a marketing personality, but because he’s the rare case where the same play is documented end to end, including the run where it broke.

Run one: the proof of concept

Vaynerchuk took over his father’s New Jersey liquor store, Shopper’s Discount Liquors, in the late nineties, fresh out of Mount Ida College. The conventional growth path for a $3-to-4-million regional retailer was to open a second location, then a third. He did something stranger. He renamed it Wine Library, launched winelibrary.com as one of the first alcohol e-commerce sites in the country, and then went hunting for cheap attention to point at it.

The tactical details are where the arbitrage lives. He built an aggressive email operation back when email was free and nobody respected. And in the most instructive move of his career, he became one of the first advertisers to buy the keyword “wine” on Google, paying ten cents a click while everyone else ignored search entirely. Ten-cent attention, converting to bottle sales. That’s the whole thesis in one line item. In roughly five years, the business went from about $3 million a year to $60 million. He didn’t outsell his competitors on the floor; he found a distribution channel they hadn’t noticed and bought it.

Run two: turning himself into the asset

In February 2006, barely a year after YouTube existed, he pointed a camera at himself. He started Wine Library TV, a near-daily wine-review show he ran for 1,000 episodes before retiring it in 2011. On paper, it sold wine. What it actually did was far more valuable: it converted the most underpriced channel of that moment, online video, into a personal audience that belonged to him rather than to the store.

That audience compounded into assets the liquor business never could have produced. A keynote at the Web 2.0 conference became the spine of a roughly $1-million, ten-book deal with HarperCollins, and the first of those books, Crush It!, became his first New York Times bestseller. The realization underneath this run is the one most founders miss: his own attention was a reusable asset, and unlike inventory, it didn’t deplete when he spent it. He’s since stacked six bestsellers and an audience of 45 million followers on top of that single insight.

Run three: selling the engine to everyone else

By 2009, the move was obvious enough to productize. He and his brother, AJ, founded VaynerMedia on a simple pitch: we did this for a liquor store, we can do it for your brand, and, true to the arbitrage mindset, never raised a funding round, starting in a borrowed conference room. The agency’s job was to run attention arbitrage as a service for companies that couldn’t run it themselves.

It scaled the way an engine scales when you sell it as infrastructure rather than a product. Revenue hit roughly $100 million by 2016, and by 2023, the agency was managing over a billion dollars in ad spend a year, with its consultancy arm growing revenue 46 percent in a single year. It now sits inside the VaynerX holding company alongside media properties like PureWow and ONE37pm, runs around 2,000 employees, and carries third-party revenue estimates near $288 million. The figures are estimates, it’s privately held, but the shape is unmistakable: he turned a personal skill into a recurring-revenue machine by renting it out.

Run four: the same bet, made with money

His angel portfolio is the purest distillation of the thesis, because it’s the identical trade executed with capital instead of content. His first three checks went into Twitter, Facebook, and Tumblr, followed by Venmo, Snapchat, Coinbase, and Uber. Read that list again, everyone is a company building a new surface for consumer attention before the mainstream understands it. He wasn’t running discounted cash-flow models. He was betting on where attention would migrate next, which is the only question he’s ever really asked. The portfolio now runs past 170 investments with 37 documented exits, and the two cleanest operator wins, Resy to American Express in 2019 and Empathy Wines to Constellation Brands in 2020, came from the same instinct applied to building rather than buying. For the record, he passed on Uber’s first round and calls it one of his biggest misses. The arbitrageur doesn’t catch every window.

What founders can actually take from this

The honest read for anyone trying to copy this is that the engine is learnable, but two of its advantages aren’t available on demand. One is timing, a liquor store hitting e-commerce in 1998, a creator hitting YouTube in 2006, and an angel hitting the social wave in 2009. You can’t summo

n a once-a-decade channel into existence because you’re ready for it. The other is the flywheel itself: by his second run, he was launching every new bet to an audience of millions, which is the exact asset most founders are still trying to build and the reason his fifth idea travels further than your first.

But the part you can steal is the part that matters. Stop optimizing the product in a vacuum and start asking the only question the engine has ever asked: where is attention gathering right now that the market hasn’t priced yet, and how do I plant a flag there before it does? Build the audience before you need it, on a channel you own, and convert it into something with real value underneath so that when the channel cools, as every channel eventually does, you’re standing on a business and not on a floor price. The operators who win aren’t the most talented in the room. They’re the ones who showed up to the right channel early and stayed long enough to own the audience.

That’s the whole game. Find the gap. Buy it cheap. Own what you build.

New article every Tuesday.

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, 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.

🎧 Listen to the episode

Youtube | Spotify | Apple

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.

Be Bold. Be Real. Be Anomalous.

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

We are social animals.

We need people around us. Community. Connection. The feeling of being needed, liked, and understood. That is not a weakness; that is just human. But here is where it gets complicated. When we constantly look outside ourselves for validation, when who we are becomes a reflection of what others expect, we slowly lose the thread that connects us to ourselves.

And most of us don’t even notice it happening.

I talk to a lot of people. And one of the things I hear more than almost anything else is some version of this: I used to be really good at drawing or painting or writing or music. Or something. Some outlet, some gift, some part of themselves that got quietly buried under the years of becoming what they were expected to become.

I understand that more than I can say.

In high school, I wanted to be a fashion designer. I used to draw sketches. I was cultivating something, a skill, a vision, a version of myself I was curious about. But I didn’t have access to that world. I couldn’t see what you could actually do with those skills. My dad is an engineer. My mom is an accountant. They were building a business, doing what worked, doing what made sense. And so I followed what I could see. I was good at problem-solving, and that part of computer science made sense to me. So I went there and, in doing so, quietly buried the creative, designing side of who I was.

I am not saying I would have become a fashion designer. That is not the point.

The point is that who we are today is shaped far more by our surroundings than by what was actually inside us. The access we had. The examples we could see. The expectations that were spoken and unspoken. We became what was visible to us. And everything else, the gifts, the curiosities, the quiet passions got left behind.

So stop for a second.

Is there something in you that got buried? Something you were once good at, once drawn to, once lit up by that you haven’t touched in years?

One of the reasons I love talking to people from so many different industries and walks of life is that I want people to see the opportunities that lie ahead. The ones I couldn’t see when I was a kid, standing at the edge of a world I didn’t have a map for.

I was always a dreamer. I didn’t always have the window to see what was possible.

Maybe this is your window.

How do you find it again?

If you are confused about how to even get started, the following might help, but I do have to say it is an effort, and you have to take the time.

Go back to childhood.

What did you love before the world told you what to love? Before the pressure of practicality, before the expectations, before you knew what was realistic. Think back to what you did purely for the joy of it.

Notice what you admire in others.

Sometimes what we admire most in other people is a reflection of something dormant in ourselves. The artist you follow obsessively. The writer whose work stops you cold. Ask yourself what it is about them that pulls me? The answer is usually closer to home than you think.

Try things without the pressure of being good at them.

We stopped exploring because we became afraid of being beginners. Permit yourself to be terrible at something new. Take the class. Pick up the instrument. Open the sketchbook. You are not auditioning. You are excavating.

Sit in the quiet and ask yourself honestly.

If nobody was watching. If money weren’t a factor. If you had nothing to prove, what would you spend your days doing? Write that answer down. However impractical it sounds.

What I’m Reading

The Cold Start Problem - Andrew Chen(Finished)

Explores why platforms like Uber, Airbnb, Tinder, and Facebook struggled in their earliest days and how they overcame the challenge of building network effects from zero. This is a must-read for anyone who is starting a marketplace or using network effects.

Crush It - Gary Vee (Reading)

I want to use this as a guide for building.

Never Split the Difference - Chris Voss(Reading)

I have been told this is a must-read for negotiating.

What Else Dropped This Week

Off Script

Identity, Nuance, and Building the Media Company South Asians Deserve | Hiba Irshad

The Startup Lawyer Breaking Every Rule, and Writing Better Ones - Aravinda Seshadri

Under the Hood

The New Media Moguls Nobody Saw Coming

Note to Self

Somewhere along the way, you buried a part of yourself to become what made sense to everyone else.

You are the only person who will be there for yourself till the very end. So enjoy your own company. Get curious about yourself again. The way you were before the world had opinions about who you should be.

That person never left. She just got quiet.

It is time to listen.

Be bold. Be real. Be Anomalous.

— Sai Menon

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

A 13-year-old kid in North Carolina uploads a gaming video to YouTube from a secondhand laptop. A 24-year-old graduate in New York records a podcast about her dating life with her roommate from their Lower East Side apartment. A university dropout in Manchester builds a social media agency out of his bedroom and starts talking into a microphone because he has no one else to tell his ideas to.

None of this looked like the future of media. All of it was.

While television executives were protecting their ad rates and radio programmers were cutting staff and magazine publishers were asking why nobody was reading anymore, a different kind of media company was being built in bedrooms and apartments. Just a camera, a microphone, and an audience that kept getting bigger.

The creator economy, the industry built around individuals who produce and monetize content independently, is now worth an estimated $250 billion globally, and is projected to reach $500 billion by 2030. YouTube’s daily usage passed Netflix worldwide in 2026. Podcasts converted 67% of their listeners into buyers of something. Netflix is now cutting deals to put podcasts on its platform because daytime television is in freefall. The old guard didn’t see the disruption coming because it didn’t come from Silicon Valley or Hollywood. It came from people who just refused to stop posting.

Three of those people, Jimmy “MrBeast” Donaldson, Alex Cooper, and Steven Bartlett, are now building what traditional media always claimed it was: a genuine connection with a massive audience that translates into real money. Here’s how they actually got there.

Jimmy Donaldson Started With Nothing. He Still Acts Like It.

In 2012, a 13-year-old from Greenville, North Carolina, started posting gaming videos. His channel was called MrBeast6000, a name that came from a randomly generated Xbox gamertag. His production quality was terrible. His thumbnails were an afterthought. He spent close to five years posting consistently before he hit a million subscribers.

What he was doing in those early years, though, wasn’t just posting. He was studying the platform obsessively, analyzing what made videos spread, what kept viewers watching, and what the algorithm rewarded. He made videos counting numbers for hours. He ranked other YouTubers’ subscriber counts. He reacted to bad content to attract people who made bad content. None of it was glamorous, but all of it was data. He dropped out of East Carolina University after two weeks because he was editing videos in the parking lot instead of going to class.

The breakthrough came when he stopped trying to optimize the algorithm and started trying to break it. In 2017, he posted a video of himself reading out loud for 24 hours. Then he started giving money away, $10,000 to a stranger, $100,000 buried in a field, and a Lamborghini to someone who kept their hand on it longest. Spectacle as content. Generosity as strategy. The thesis was simple: if the video was worth more to the viewer than anything else competing for their time, they’d watch. They’d share. They’d come back.

It worked. By 2022, he had surpassed PewDiePie to become the most-subscribed individual creator in YouTube history.

How does he make money? Every possible way. YouTube ad revenue from hundreds of millions of views per video. Feastables, the chocolate bar brand he launched in 2022, now sits in over 80,000 retail locations across North America, including Walmart, Target, and 7-Eleven, pulling an estimated $200 million in annual revenue. Beast Industries, the holding company behind all of it, raised at a $5 billion valuation. And then there’s Beast Games, the Amazon Prime Video reality competition where he put up a $10 million prize pool and nearly 5,000 contestants. Amazon made over $100 million in profit from Season 1 within its first four weeks. Season 2 aired in January 2026. Season 3 is in negotiation, with Donaldson reportedly asking $150 million per season, and last week, he reached 500 million subscribers on YouTube.

He is, by every measure, the largest individual media operation in the world. And he still talks about it like a kid who might wake up and find out it wasn’t real.

Alex Cooper Was Told No. She Found a Different Door.

Alex Cooper grew up in Newtown, Pennsylvania, played Division I soccer at Boston University, and had her athletic career ended by a knee injury. She graduated in 2016 and moved to New York to work entry-level media jobs, navigating a dating life in Manhattan she later described as “chaotic in the best and worst ways.”

In 2018, she and her roommate, Sofia Franklyn, started recording a podcast from their apartment. The idea was simple: say the things women actually talk about among themselves but never out loud in public, sex, relationships, ambition, and dating disasters. They called it Call Her Daddy. They uploaded it to Barstool Sports, which gave them distribution and a small salary in exchange for owning the show.

Within two years, Call Her Daddy had become one of the most listened-to podcasts in the country. Then everything almost fell apart. In 2020, a contract dispute with Barstool founder Dave Portnoy became public. Franklyn left. Cooper was left holding a podcast she didn’t fully own, with an audience who’d watched her fight publicly for control of her own work. Instead of waiting for the situation to resolve itself, she negotiated hard, won sole ownership of the show, and kept going alone this time.

In 2021, Spotify signed her to an exclusive deal worth $60 million over three years. In 2024, SiriusXM came with a bigger offer: up to $125 million over three years, with advertising and distribution rights not just for Call Her Daddy but for the entire Unwell Network, the podcast collective she’d been quietly building around herself, backing voices she thought could command the same kind of loyalty she had built. Kamala Harris came on the show during the 2024 election campaign, the same week Donald Trump appeared on Joe Rogan’s. That parallel told you everything about where political press tours had moved.

How does she make money? The $125 million SiriusXM deal is the anchor, but the business underneath it keeps expanding. Unwell Hydration, her electrolyte drink brand, launched in partnership with the National Women’s Soccer League. Unwell Creative Agency launched with Google as its first client, helping brands reach Gen Z through original productions. She directs the creative, earns the ad revenue, owns the IP, and, unlike every radio host or television personality who came before her, keeps the upside from everything she builds on top of it.

Steven Bartlett Dropped Out After One Lecture.

Steven Bartlett was born in Botswana, moved to England at two years old, grew up in Plymouth, and lasted exactly one month at Manchester Metropolitan University before he decided a classroom wasn’t going to teach him what he needed to know.

In 2014, he co-founded Social Chain, a social media marketing agency that understood something most traditional agencies didn’t: that internet communities were the new media channels, and the brands that learned to speak their language would win. Social Chain grew to over 200 employees, landed clients including Apple, McDonald’s, and the BBC, and went public through a merger in 2019. Bartlett, at 27, became one of the youngest people to take a company public in Europe.

He stepped down as co-CEO in 2020. And instead of retiring or starting another agency, he did something most people coming off a nine-figure business exit don’t do: he started a podcast because he wanted to figure out what he’d actually learned.

The Diary of a CEO launched in 2017 while he was still running Social Chain, initially as a personal audio diary, something to organize his own thinking. Over time, it became something else. He started interviewing entrepreneurs, scientists, psychologists, athletes, world leaders, and anyone who’d done something worth understanding. By 2025, Spotify Wrapped ranked it as the second-most-popular podcast globally. It now has over 15 million YouTube subscribers, 70 million monthly downloads, and has passed one billion YouTube views in late 2025.

In October 2025, Bartlett raised a major eight-figure investment for Steven.com, his holding company, at a $425 million valuation, retaining over 90% ownership. The structure underneath it: FlightStory, a media production arm; FlightCast, a podcast hosting platform built natively for video; FlightFund, a venture arm with investments in SpaceX, Whoop, Groq, Replit, and MrBeast. He has backed more than 40 companies. His stated ambition is to build the Disney of the creator economy. This machine takes creator IP and compounds it the way Disney compounded Mickey Mouse into a century-long entertainment empire.

How does he make money? The Diary of a CEO generates an estimated $20 million a year in advertising alone. FlightStory produces content for other creators and brands. FlightFund invests. FlightCast monetizes the infrastructure. And as the youngest-ever Dragon on BBC’s Dragons’ Den, he’s gained equity stakes in businesses that have nothing to do with content at all.

What This All Actually Means

The numbers are one thing. The shift underneath them is something bigger.

Traditional media, television, radio, and publishing were built on a model where the institution owned the audience. A network had viewers. A station had listeners. A magazine had subscribers. The individual on camera or behind the microphone was the hired talent. The distribution was the asset, and the institution held it.

What MrBeast, Cooper, and Bartlett built is the opposite of that. The individual is the distribution. The audience follows the person, not the platform, which is why Cooper can move from Spotify to SiriusXM and take her listeners with her, why MrBeast can launch a chocolate bar and have it in 80,000 stores within three years without a single traditional marketing campaign, and why Bartlett can raise $425 million at 33 and still own 90% of the company. None of them is an employee of the medium they work in. They own the relationship.

This is what “replacing traditional media” actually looks like. Not a dramatic collapse, but a quiet migration of audience trust from institutions to individuals, and with it, a migration of the economics. The ad money that used to flow to television networks and radio stations is now flowing directly to the people audiences chose to spend their time with. YouTube’s daily usage passing Netflix isn’t a quirk. It’s a verdict.

The three people above didn’t plan to build media empires. They started with a camera, a microphone, and something they wanted to say. The audiences found them and then stayed. In a world overflowing with content, that sustained attention turned out to be worth more than anything the old model ever produced.

New article every Tuesday.

Be Bold. Be Real. Be Anomalous.

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

I found true liberation when I stopped caring what people think.

And I don’t say that lightly. It changed everything about how I live, how I speak, how I react, how I show up. There is a freedom in it that I cannot fully put into words, but once you feel it, you cannot unfeel it.

We spend so much of our lives consumed by it. What will they think? Will they misunderstand me? Will they think I am rude? Too much? Not enough? And all of that noise, all of that second-guessing quietly shrinks you. It keeps you performing a version of yourself for an audience that isn’t even paying as much attention as you think.

Here is what I know now. If you know your intentions, if you know who you are at your core, and you are not guilty of doing anything wrong, there is nothing to defend. Nothing to explain. Nothing to shrink for.

I won’t pretend it is easy. It took me 36 years to get here. And sometimes I think if I had realised this earlier, how much I would have done differently? But then I remember the journey is what got me here. Every part of it.

This life is yours to create. Yours to build into exactly what you want it to be. Yes, circumstance matters. Access matters. The birth lottery is real. But don’t start by looking at what others have. Start with what you have. And from there climb. It might take longer. But your days will be happier. I truly believe that.

I have been happiest building what I love and spending my days with the people I actually want to be around.

That is it. That is the whole thing.

How did I get to not caring?

These are the things that actually moved the needle for me

Reading more

Reading truly changed my life. The more I read, the more I understood myself. The more I understood the world. The more I stopped needing external validation to feel grounded in who I am.

The book Let Them by Mel Robbins

This one was crucial. The first time I read it, it liberated me. It validated something I had been feeling but didn’t have the words for yet. If you haven’t read it, read it.

Changing my circle

As I started creating distance from people who were bringing me down, people who made me question myself, people who drained my energy without adding anything back, everything shifted. You don’t realise how much weight you are carrying until you put it down.

Discipline and working out

When you commit to something hard, when you show up for yourself physically, consistently, it changes what you believe you are capable of. That belief bleeds into everything else. You stop doubting yourself as much. You start trusting yourself more.

And one more thing — this one might surprise you.

I used AI to generate an image of the future I am building. The life I am working toward. And seeing myself there visually, concretely, became one of the biggest sources of motivation I have ever had. Everything else starts to become noise when you can actually see where you are going.

What I’m Reading

The Cold Start Problem - Andrew Chen(Currently Reading)

Explores why platforms like Uber, Airbnb, Tinder, and Facebook struggled in their earliest days and how they overcame the challenge of building network effects from zero. The book offers a practical framework for entrepreneurs on how to create momentum, reach critical mass, and turn a small community into a thriving network.

Crush It - Gary Vee (Reading)

I want to use this as a guide for building.

What Else Dropped This Week

Off Script

Identity, Nuance, and Building the Media Company South Asians Deserve | Hiba Irshad

The Startup Lawyer Breaking Every Rule, and Writing Better Ones - Aravinda Seshadri

Under the Hood

How Three Startups Broke Three Different Monopolies

Note to Self

You are not performing for anyone.

You know your intentions. You know who you are at your core. That is enough. You don’t owe anyone an explanation for how you live, what you choose, or who you are becoming.

Stop shrinking for rooms that were never built for the fullest version of you.

The people who are meant to understand you will.

The ones who don’t — let them.

This life is yours. Build it accordingly.

Be bold. Be real. Be Anomalous.

— Sai Menon

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

Three companies did exactly that.

• Warby Parker attacked an economic monopoly built on vertical integration.

• Uber dismantled a government-protected monopoly propped up by artificial scarcity.

• Spotify survived a platform monopoly enforced by a 30% tax on its own existence.

Each fight was different. Each win was instructive.

The Economic Monopoly: Luxottica and Warby Parker

Before Warby Parker existed, the eyewear industry was one of the most quietly predatory monopolies in American consumer goods. Starting in 1961 as a small workshop in Agordo, Italy, Luxottica grew from a parts manufacturer into a vertically integrated empire, designing, making, distributing, and selling glasses all under one roof. Over decades, it executed a simple but devastating playbook: buy everything. It acquired Ray-Ban in 1999, Oakley in 2007, and built a portfolio that let it dictate industry trends and set pricing standards across both luxury and sports eyewear. Then it bought the stores. After acquiring Sunglass Hut and LensCrafters, Luxottica controlled an estimated 80% of luxury eyewear manufacturing and roughly 50–60% of global retail optical. You didn’t choose to work with Luxottica. You realized you had to.

The result for consumers was brutal. Frames were being sold at prices 20 to 25 times their manufacturing cost. A $13 frame hitting shelves at $300 or more wasn’t a pricing quirk; it was the system working exactly as designed.

The four Wharton students who founded Warby Parker in 2010 stumbled into this while researching why glasses were so expensive. The answer kept coming back to one company. Luxottica had a near-monopoly on the eyeglass and sunglasses market; prices were too high, products weren’t great, and the shopping experience was poor.

Their insight wasn’t just that the prices were wrong; it was why they were wrong. Luxottica’s power came from owning every link in the chain. So Warby Parker built their own chain. They created a vertically integrated model that bypassed retailers and middlemen, transferring the cost savings directly to consumers. Glasses started at $95. The Home Try-On program ships five frames to your door, solving the one genuine objection to buying glasses online: you can’t see how they look on your face.

As co-founder Neil Blumenthal put it, “The market charges too much for glasses, and that was due to a consolidation of power within the industry that had been built up over decades,” which was exactly what allowed Warby to come in and charge $95 for a $500 product.

By 2025, Warby Parker had reached $872 million in annual revenue with 323 retail stores across North America. They didn’t beat Luxottica at its own game. They changed the game entirely.

The Government Monopoly: Taxi Medallions and Uber

Luxottica’s monopoly was built through acquisition. The taxi industry was built through legislation, which made it, in some ways, even harder to crack.

The medallion system was a masterpiece of artificial scarcity. Cities required taxi companies to purchase government-issued medallions to operate legally. The supply was capped. The cap meant prices stayed high. In New York City, medallion prices peaked at over $1 million each. The system benefited medallion holders enormously and consumers almost not at all. No competition meant no incentive to improve service, invest in technology, or lower prices.

Uber’s origin story is almost too clean: Travis Kalanick and Garrett Camp couldn’t get a cab in Paris in 2008. That frustration became a company. But the real strategic insight wasn’t the app; it was the classification. Uber entered as a technology company, not a taxi company. Drivers weren’t taxi drivers. They were independent contractors using personal vehicles. That framing put Uber outside the regulatory framework that the medallion system depended on. You can’t require a software platform to buy a taxi medallion.

From there, Uber’s expansion followed a deliberate sequence: target young, affluent, tech-comfortable early adopters in dense urban markets; build supply and demand simultaneously on both sides of the marketplace; deliver an experience so obviously superior to taxis that switching became reflexive. GPS tracking, cashless payment, upfront pricing, and two-way ratings were each a direct attack on a specific failure of the incumbent.

The medallion system collapsed not because regulators dismantled it, but because consumers stopped caring about it. By the time cities fought back with new regulations, Uber was already embedded in daily life. The monopoly didn’t lose a regulatory battle. It lost the consumer.

The Platform Monopoly: Apple and Spotify

Warby Parker’s enemy owned the supply chain. Uber’s enemy owned the permits. Spotify’s enemy owned the device.

When Spotify launched in 2008 and expanded to the US in 2011, the company faced two simultaneous existential threats. The first was the music industry itself, alarmed by the sudden erosion of their business, the major record labels finally signed licensing deals with Spotify and quietly took an estimated 14% combined stake in the company. The second threat was Apple, which controlled the platform through which most people would actually discover and use Spotify.

The mechanics of Apple’s leverage were precise. Apple took a 30% cut of any Spotify subscription paid through the App Store. One of Spotify’s main competitors was Apple Music, which paid no such toll. Apple also prohibited Spotify from telling its own users that cheaper subscription options existed outside the app. In many cases, getting app approvals required sharing proprietary strategies with Apple, Spotify’s biggest competitor, with no restrictions on what Apple could do with that information.

The competitive math was simple and ugly: Spotify either absorbed the 30% tax and made its premium tier more expensive than Apple Music, or it removed in-app purchases entirely and accepted a worse user experience. Either way, Apple won.

Spotify’s response was to fight on three fronts simultaneously. It scaled aggressively to build the kind of user base that made it impossible to ignore — Spotify not only had to build its own brand, but it also had to educate an entire customer base about the benefits of streaming. It was the icebreaker that cut the path through which Apple, Amazon, YouTube, and others could follow. It diversified its revenue base, pouring resources into podcasts to reduce dependence on music royalties. And in 2019, it went nuclear: CEO Daniel Ek filed an antitrust complaint with the European Commission, accusing Apple of abusing its control over the App Store to stifle competition and restrict consumer choice.

The regulatory campaign took five years. In March 2024, the European Commission fined Apple nearly $2 billion — the first-ever antitrust penalty levied by the EU against Apple, and four times higher than insiders had predicted. The ruling forced Apple to allow Spotify to show pricing information to EU users and link directly to external purchase pages. The 30% tax on music streaming was effectively over in Europe.

Spotify finally reached profitability in 2024. It took sixteen years. The platform monopoly didn’t fall to a clever product feature or a better user experience. It fell to a sustained regulatory campaign backed by the weight of Spotify’s 600 million users.

The Pattern Underneath

The pattern underneath is clear: the companies that break monopolies do not fight the incumbent’s surface; they attack the mechanism that makes the incumbent powerful. Warby Parker did not try to become a fancier Luxottica; it built a new supply chain and a new way to buy glasses. Uber did not ask for a better place inside the taxi system; it made the taxi system itself feel outdated. Spotify could not go around Apple, so it moved fast enough, scaled hard enough, and changed listening behavior enough to make the old gatekeeping less effective.

That is the real founder lesson. We are often trained to optimize for caution, for narrow niches, for staying out of the incumbent’s line of fire. But the companies that matter most are the ones that see the structure clearly and build something that makes that structure irrelevant. The monopoly is never the full story. The mechanism is. And once you see the mechanism, disruption stops looking like rebellion and starts looking like strategy.

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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.

Be Bold. Be Real. Be Anomalous.

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Are you feeling consumed by the pace of everything around you?

Things are moving fast. Everyone is running toward the next big win, the next big bet, the next big thing. There is a constant hum of urgency that follows you everywhere on your feed, in your conversations, in the back of your mind at 2 am when you should be sleeping.

And if you are feeling behind, overwhelmed, like you are scrambling to catch up to everyone and everything, I want you to know something.

You are not alone. I feel it too.

But here is the truth that nobody says out loud. Everyone is trying to catch up to something that nobody really knows. We are all chasing so we are not left behind. But left behind from what exactly? Nobody has a clear answer. We are all just running because everyone else is running. And somewhere along the way, the running became the point.

It isn’t a race.

Or if it is, nobody told us where the finish line is. Nobody agreed on what winning looks like. And yet here we all are, breathless, comparing our pace to everyone else’s, wondering why we can’t keep up.

So take a breath.

Just stop for a moment. Because the world will keep moving whether you sprint or whether you pause. And the pause is not falling behind. It is the only way to remember why you started running in the first place.

You are not behind. You are exactly where you are.

And that is enough to work from.

Let’s do something today. Together.

Write it down. Right now. With me.

Because if we are going to run, and we will run, that is just who we are, we should at least know what we are running toward.

And we should know how far we have already come.

What is your finish line?

Not someone else’s, or not the one you feed, is selling you. Yours. What does winning actually look like for you in your life, on your terms? Get specific. Write it down. Because a finish line you cannot see is just exhaustion with no reward at the end.

What are you chasing?

Be honest with yourself here. Is what you are chasing something you actually want, or is it something you feel you are supposed to want? Is it yours, or did you inherit it from the noise around you? Write it down. The answer might surprise you.

How far have you come?

This is the one we skip the most. We are so focused on how far we have to go that we never stop to look back at the ground we have already covered. The things you have figured out. The hard seasons you have survived. The version of yourself you have already left behind. Write it down. You have come further than you are giving yourself credit for.

Take the time today. Not tomorrow. Today.

Because you cannot run well toward something you have never clearly defined. And you cannot appreciate the journey if you never stop to look at how far you have already travelled.

You are not behind. You are building. And you have been building all along.

Now write it down.

What I’m Reading

Start with Yourself - Emma Grede (Finished)

This is an easy, engaging read. If you admire Emma or consider yourself ambitious, it's well worth your time.

The Cold Start Problem - Andrew Chen(Currently Reading)

Explores why platforms like Uber, Airbnb, Tinder, and Facebook struggled in their earliest days and how they overcame the challenge of building network effects from zero. The book offers a practical framework for entrepreneurs on how to create momentum, reach critical mass, and turn a small community into a thriving network.

What Else Dropped This Week

Off Script

From Bartender to Co-Founder: How Helen Diaz Built a National Brand Without Losing Herself

The Startup Lawyer Breaking Every Rule, and Writing Better Ones - Aravinda Seshadri

Under the Hood

The Scarcity-to-Scale Paradox: How an 11-Table Restaurant Built a $2.7 Billion Brand

Note to Self

Stop running for a moment.

You cannot win a race you never defined. So before you take another step, get clear on what you are actually chasing and why.

And while you are at it, look back. You have come further than you think.

Be bold. Be real. Be Anomalous.

— Sai Menon

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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
Youtube | Spotify | Apple

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.

Be Bold. Be Real. Be Anomalous.

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