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

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

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

🎧 Listen to the Episode

[Spotify] | [YouTube]

What You’ll Learn

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

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

• How COVID unexpectedly became the catalyst for starting her company

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

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

• How pop-ups validated product demand before opening stores

• The realities of bootstrapping a physical retail business

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

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

• The importance of staying lean while scaling intentionally

Favorite Quote

“Work hard and be nice to people.”

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

Favorite Books

📖 The E-Myth Revisited — Michael E. Gerber

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

In This Episode, We Cover

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

(05:00) Early ambition and shifting career paths

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

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

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

(25:00) Launching online during the pandemic

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

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

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

(45:00) Balancing motherhood and entrepreneurship

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

(55:00) Redefining success across life and business

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

Referenced in This Episode

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

• Entrepreneurship during COVID and business resilience

• Multi-brand retail strategy in children’s fashion

• Bootstrapping vs. fundraising decisions

• Hiring, delegation, and early-stage team building

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

• The future of in-person retail experiences

• Global sourcing of children’s clothing brands

New episodes drop every Monday and Thursday.

Be bold. Be real. Be anomalous.

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

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This week felt different, not because it was easier, but because I could finally see it clearly. My son had spring break, and it also happened to be my birthday. My husband and I are always working to balance careers and childcare, to carve out real time with him. This week, that balance tilted toward me. My husband carried a heavier load at work and felt the weight of missing out. I had more flexibility, and so I had more of our son.

And here’s what struck me: a year ago, maybe two, I would have said I have to take care of him this week. A quiet resentment buried in the phrasing, the kind you don’t even notice until it’s gone. This week, without really planning it, I noticed myself thinking differently: I get to be here with him.

Watching my husband grieve the moments he was missing made it real for me. Time with a child isn’t a given. It isn’t owed. It’s a gift, and like most gifts, it’s easiest to take for granted right up until the moment you can’t have it.

Don’t get me wrong, I’m not saying every day is easy. Some days it does drive you a little crazy. But the mindset shift doesn’t ask you to pretend otherwise — it just changes how you hold it. It invites you to be in the moment rather than enduring it.

And once you see it, you can't unsee it. It starts to reach into everything. I get to work out. I get to do my work. I get to be with my family. None of it is guaranteed. All of it is precious.

That’s been my realization this week: Savour it. Take the chance. You don't know how long you get to do any of it.

Reframe Your Mindset

• Notice the language you use Start by just catching yourself. When you hear "I have to," pause and ask: Is this actually something I chose, or something I'm lucky to have? You don't have to force a reframe every time; just noticing builds the habit.

• The subtraction exercise. Imagine the thing is gone. The school pickup, the work meeting, and the dinner to cook. Who would you be without it? Often, what feels like a burden is actually evidence of a life you built: a job, a family, a home. Subtraction makes the invisible visible.

• Anchor to the “why” behind the “what.” Instead of thinking about the task, think about what it represents. Driving your kid to practice = you have a healthy child who gets to play. Paying bills = you have a home and a life running. The task is just the surface; underneath is the meaning.

• Change the story you tell others. When someone asks how your week was, notice if you lead with a complaint or with gratitude. You don't have to pretend it was perfect but try ending on what you were glad to have, even in a hard week. How we narrate our lives shapes how we experience them.

Gratitude isn't pretending the hard days don't exist. It's making sure the good ones don't pass unnoticed.

What I’m Reading

Grit — Angela Duckworth (Finishing)

This one really stays with you. It breaks down the idea that success isn’t just about talent; it’s about consistency, resilience, and showing up even when it’s hard. What I’ve been reflecting on most is how grit isn’t always loud.

A Different Kind of Power - Jacinda Ardern

It reflects on her journey into leadership and the personal values that guided her time in office.It explores how empathy, resilience, and compassion can redefine strength in politics and inspire a more human-centered approach to power.

What Else Dropped This Week

Off Script

How Shahezad Left IT to Build Cousins Burger (Lessons on Scaling & Risk)

Under the Hood

He Started With $1,000, One Customer, and a Mediocre Product. Two Years Later, He Sold for $100 Million.

Note to My Future Self

The practice is simple, even when it isn’t easy. Notice the language. Anchor to the meaning. Show up for the ordinary moments as if you know because you do know, that they won’t last forever.

“I have to” keeps you surviving your life. “I get to” lets you live it.

That’s the whole shift. Two words. One choice. Made again and again, on the hard days especially.

Be bold. Be real. Be Anomalous.

— Sai Menon

In July 2015, Moiz Ali bought a domain name on GoDaddy. It was his birthday.

He had $1,000 of his own money and one idea: a natural deodorant people might actually buy online. Twelve days later, he launched a website. There was no product in hand, just 3D-rendered images of a deodorant stick he hadn’t manufactured yet. He planned to take orders first, then figure out the supply.

Day one: one sale.

He nearly shut the whole thing down.

The Setup: A CVS Aisle and an Unreadable Label

Moiz Ali was 30 years old and had already sold his first company, Caskers, a craft spirits e-commerce business he’d started with a law school friend. That exit was seven figures. Comfortable money, not retire-forever money. He was looking for his next move.

He found it reading the back of a deodorant can while standing in a CVS aisle. Aluminum Zirconium Tetrachlorohydrex. Isopropyl Palmitate. Cyclopentasiloxane. He couldn’t pronounce a single ingredient. His sister was pregnant at the time and asking questions about the chemicals in her Dove deodorant. And he’d noticed something else: natural deodorant was the number one product on Etsy in 2015. A real market, mostly being served by small artisan makers out of their home kitchens.

The mainstream natural options that existed felt clinical or ineffective. There was a gap: a natural deodorant that worked, looked premium, and didn’t require you to identify as a health food person to buy it.

In Ali’s own words, his goal was to do what Whole Foods did to food, but to the deodorant category. Not something “very hipster or grungy, but something mainstream.”

He went on Etsy, found the best natural deodorant makers, and asked if any of them would white-label their product for him. It took dozens of rejections before one person agreed to a woman making deodorant in her hobby room in Southern California. He placed his first small order.

Then he launched.

The Launch: No Product, No Photos, No Guarantee

He launched the website with zero deodorants in hand and no photos of the physical product. Instead, he found someone to 3D render the product to use as images on his site. He wasn’t sure people would shop for deodorant online, so he treated the launch as a test; he would order the deodorant once he made sales.

He decided on the price of $12 a stick by working backwards from his costs. Six dollars to manufacture, three dollars to ship, one-fifty in packaging. The math pointed to $12, two to three times the price of drugstore deodorant. He didn’t discount his way in. He set the price that made the business work and bet that the product would justify it.

Day one: one customer. Ali was deflated. Then a connection helped get Native bumped onto Product Hunt’s front page. Day two: dozens of orders. He called his manufacturer and placed his first real production order. He packed and shipped those early sticks himself.

His reaction to a friend asking what he knew about deodorant captures everything about his approach:

“I know nothing, and in six months, I’m going to become one of the world’s leading experts on deodorant. I’m just going to spend my time learning, and I’m going to figure it out.”

The First Year: One Employee, Thousands of Emails

For the first year, Ali was the only employee, handling everything himself.

The product, by his own admission, wasn’t very good. It was powdery, hard to apply, and occasionally had a consistency problem in the summer heat in May 2016. As temperatures rose, the deodorant started melting to the consistency of lotion. Rather than quietly recall it, he stopped production, rushed an improved formula that had only been tested on a dozen people, and got it to market as fast as he could.

What saved him wasn’t the formula. It was his relationship with customers.

Ali emailed every single customer for the first two years of the business with the same message:

“You just got a stick of Native deodorant. Love to know what you think about it. If you love the product, please leave a review on our site. If you don’t, reply to this email and tell us what you don’t like, and we’ll try to fix it.”

The complaints came in consistently for the first year: too powdery, too hard to apply, too many oils. He listened. He iterated. The repeat purchase rate, which tells you whether people are actually satisfied, started at around 20%. It climbed steadily to 50% as the product improved. He bought deodorant from every competitor and noted every detail that made them better. The formula changed dozens of times.

Native went from a couple of hundred dollars in revenue per month in July 2015 to $75,000 in revenue per month by January 2016, and it was still just Moiz. By May 2016, they were doing $100,000 a month.

“I wish Silicon Valley didn’t glorify massive fundraising rounds as much as they do,” he later said. “People don’t respect how much one person can do.”

The Growth Engine: Discipline Over Flash

As revenue grew, Ali built each piece of the business the same way he built the product: methodically, based on what the data actually said.

Pricing held firm. He never discounted. The $12 stick gave him a real gross margin enough to invest in customer acquisition while building toward profitability. He understood early that the economics of DTC only work if you know your customer’s lifetime value and never spend more than that to acquire them.

Subscriptions compounded. He built a subscription option offering customers 15% savings with multiple delivery interval choices. This turned episodic buyers into predictable recurring revenue, compressed his payback period on customer acquisition spend, and gave the business a foundation that looked genuinely attractive from the outside.

Advertising was measured, not sprayed. He tracked every Facebook and Instagram dollar against long-term customer value, not just first purchase. When he found a channel that worked, he doubled down. When a conference in San Diego introduced him to better Facebook advertising techniques, he came back and grew 400% in 60 days.

Retail was ignored — intentionally. Costco called. Whole Foods called. Every major retailer you can imagine called. He turned them all away. He had a just-in-time inventory system for DTC that could barely keep up with demand; he never had excess product to ship to brick-and-mortar retailers. He stayed focused on what was working.

The revenue progression tells the story clearly: January 2016, $50,000 in monthly revenue. June, $250,000. November was the first $1 million month. The following November, $5 million.

Within 18 months of launch, Native had $13 million in cash in the bank. By the time P&G came calling, it was generating close to $1 million in EBITDA per month.

The Exit: $100 Million, 2.5 Years In

In November 2017, Procter & Gamble acquired Native for $100 million in cash. It was P&G’s first acquisition in nearly a decade, and until the deal closed, Native hadn’t sold a single stick of deodorant outside its own DTC website.

Ali hadn’t set out to sell. But the business was at an inflection point; every major retailer in America wanted in, and scaling into retail would have required a different kind of company: more capital, more inventory, more infrastructure. P&G could provide all of it.

For P&G, the acquisition made strategic sense on multiple levels. They were under pressure from activist investor Nelson Peltz to acquire on-trend brands rather than just cut costs. Native offered a beachhead in the growing natural personal care segment, a proven DTC playbook, and something P&G couldn’t manufacture internally: authentic customer trust built on a genuinely better product.

Ali stayed through early 2020. By the time he left, Native was doing $60 million a year in Target alone and had become the third best-selling deodorant brand in the store behind Secret and Dove. P&G extended the brand into body wash, hair care, and lotion. The $1,000 birthday bet had become one of the most successful consumer brand exits of its decade.

What It Actually Teaches

The Native story gets told as a fairy tale, a guy with a great idea who got lucky with timing and cheap Facebook ads. That’s comfortable, so you can get off the hook.

What Ali actually did was execute a set of principles with unusual consistency and discipline.

He launched before he was ready and used reality to course-correct, rather than spending months perfecting something in private before exposing it to customers. He priced for margin from day one and never flinched, because he understood that discounting is how you build a business that can never become profitable. He treated every customer email as product research. He ignored every shiny retail opportunity until the core business was undeniably working. He built a subscription model not as a marketing gimmick but as a genuine retention mechanism that made his unit economics legible to anyone looking at the company.

And he did almost all of it alone, for longer than most founders would tolerate.

The lesson isn’t that you had to launch in 2015 to build Native. The lesson is that there is another Native launching today, and the founders building it are probably being told they should raise more money, open more channels, and move faster. Most of them won’t need to do any of those things.

They’ll need to do what Moiz did: make something people actually want, listen until they’re sure of it, and have the discipline not to complicate what’s working.

If this was useful, please share it with anyone who needs to hear it.

New Article drops every Tuesday.

Be Bold. Be Real. Be Anomalous.

Episode Description

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

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

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

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

It’s how unexpected it all was.

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

And for a long time, he believed it.

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

Until one day, he decided to try something different.

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

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

And he did it differently.

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

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

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

This conversation goes beyond restaurants.

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

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

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

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

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

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

🎧Listen to the Episode

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

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

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

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

• How to scale a business without losing quality or control

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

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

• The importance of choosing the right partners and team

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

Favorite Quote

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

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

Favorite Books

📖 Roald Dahl collection

📖 The Da Vinci Code — Dan Brown

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

In This Episode, We Cover

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

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

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

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

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

(35:00) Using storytelling and AI in marketing

(45:00) Redefining success beyond money

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

(55:00) Final reflections and advice for builders

Referenced in This Episode

Cousins Burger and restaurant scaling

Entrepreneurship and career pivots

Storytelling in business and brand building

AI in content creation and marketing

Partnerships, hiring, and team building

Redefining success and long-term vision

New episodes drop every Monday and Thursday.

Be bold. Be real. Be anomalous.

This week, I was listening to a conversation with Michelle Obama, and she shared a moment that made me think.

She described the time her mother was close to the end of her life. And in that moment, her mother said, “This went by fast.”

Michelle asked, “What did?”

Her mother said, “Life.”

Even she felt it went by quickly after living an incredible life. And she said it with peace, not regret. That hit me deeply.

It made me want to pause. So I went through my photos over the years. And it put a real smile on my face.

Here’s what I noticed: around my birthday, I usually feel this immense pressure. The weight of getting older, of goals I haven’t reached, of time passing. There’s a quiet shame that comes with that.

But this time, something shifted. When I changed how I looked at things, I stopped measuring what I hadn’t done and started seeing everything I had actually lived. The moments that were never on any goal list. The things that happened anyway, and mattered.

And I smiled.

It might seem morbid to think about death. But thinking about death makes you think about life, really think about it.

A life that feels like it went by fast is a life worth living every single day.

So take time for gratitude. Spend your time with people who care about you, and who you care about.

Make your life worth living.

What I’m Reading

Grit — Angela Duckworth (Finishing)

This one really stays with you. It breaks down the idea that success isn’t just about talent; it’s about consistency, resilience, and showing up even when it’s hard. What I’ve been reflecting on most is how grit isn’t always loud.

Caste — Isabel Wilkerson (Starting)

Starting this next. It dives into the hidden structures that shape inequality across societies, beyond race or class alone. I’m curious to see how it reframes the way we think about systems, identity, and power, and what it reveals about the world we move through every day.

What Else Dropped This Week

Off Script

How Melissa Built a Beauty Brand for the People the Industry Overlooked

Under the Hood

The Quiet Profit Machine: How Store Brands Are Reshaping Retail

On My Reading Desk

1. Shoe brand once worth $4B closes all stores, avoids bankruptcy

2. The secret to mastering AI is getting the division of labor right

3. When AI Vendors Fail: Lessons From The Sora Shutdown

4. Apple’s ‘Nice Guy’ Heir Apparent

Note to My Future Self

Look at the photos. Look at the moments that never made it onto any goal list, yet there they are. That is your life. And it is more than you gave yourself credit for.

That’s what you want. A life that moves. A life that, when you look back, makes you smile without even trying.

So on the days the pressure creeps in, come back to the photos. Come back to the people. Come back to the moments that weren’t planned but happened anyway.

Those moments are not detours. They are the life.

You are not behind. You are exactly where you are supposed to be.

Be bold. Be real. Be Anomalous.

— Sai Menon

Walk into any Costco, and you’ll find it almost immediately: the Kirkland Signature label, displayed across everything from coffee to cashmere. At first glance, it looks like a house brand something to grab when you’re watching your wallet. Look closer, and you’ll find it’s made by Starbucks, Duracell, or Jelly Belly, sold at a fraction of the national brand price, and generating an estimated $60 billion in annual sales. That’s more than Nike.

The store brand, also called private label, is no longer a value proposition. It’s a profit engine, a loyalty machine, and increasingly, an existential threat to the brands that helped build the retail industry in the first place.

Store brands now account for roughly one in five consumer packaged goods sold in the United States, a share that has grown every year for the past decade. Understanding how they work and what they do to everyone else on the shelf has become essential for anyone tracking the modern retail landscape.

The Economics of the Shelf

To understand why store brands are so powerful, you need to understand where the money goes in a typical consumer goods transaction.

When a national brand sells a product, the manufacturer covers production costs, then adds significant marketing and advertising spend, often 15 to 25 percent of revenue, to build brand awareness that justifies a premium price. On top of that, the manufacturer pays the retailer slotting fees: essentially, rent to occupy shelf space, particularly prime eye-level real estate. By the time the product reaches the consumer, the retailer’s margin is typically 15 to 20 percent.

A store brand changes every one of those variables.

The retailer contracts directly with a manufacturer, often the same manufacturer making the national brand, which removes the marketing spend and slotting fees, and keeps the price lower for the consumer while capturing dramatically higher margins for itself. Where a national brand yields a 15 to 20 percent margin, the equivalent store brand often yields 35 to 55 percent. The retailer owns the shelf, so there is no auction for placement. The product goes where the retailer wants it.

The consumer wins too on price. Store brand products typically come in 20 to 30 percent cheaper than their national brand equivalents. For a household buying groceries every week, that gap compounds into meaningful savings. Retailers have learned to use this positioning deliberately: lower prices on store brand staples can be what gets a shopper through the door, and then through the rest of the store.

How the Major Players Execute

Not every retailer approaches private label the same way. The most sophisticated operators have developed distinct strategies that reflect their customer base, category mix, and competitive positioning.

Costco: The Membership Multiplier

Kirkland Signature is probably the most studied private label program in the world, and for good reason. Costco has built a brand so trusted that shoppers actively seek it out, the inverse of the traditional private label dynamic, where house brands compete on price because they lack brand pull.

The formula is deliberate. Costco caps its markup on any item at 15 percent, a policy that forces it to source with exceptional efficiency. It also contracts with best-in-class manufacturers. The Kirkland Signature batteries are made by Duracell; the coffee was long roasted by Starbucks, which means the quality is genuine. The result is a membership that renews at over 90 percent annually, driven in significant part by the value Kirkland provides.

The store brand doesn’t just generate margin; it is the reason people come back.

Target: When Private Label Becomes a Brand

Target’s approach is philosophically different. Where Costco uses Kirkland to deliver value, Target uses its owned brands to deliver aspiration.

The retailer has built more than ten owned brands, several of which exceed $1 billion in annual sales. Cat & Jack, its children’s apparel line, generates more than $3 billion a year. Threshold is the home care brand. Good & Gather has quietly become a credible grocery label. They are positioned and marketed as brands in their own right, with their own aesthetic and identity.

The implication is significant: Target’s owned brands can command comparable prices to national brands while still delivering higher margins, because the retailer controls the full value chain.

Safeway and Kroger: The Tiered Approach

Traditional grocery retailers have taken a more systematic route. Rather than building one signature brand, they run multiple tiers simultaneously: a value label for price-conscious buyers, a mid-tier for everyday quality, and a premium or organic label (O Organics, Simple Truth) for shoppers willing to pay up. Each tier competes with a different national brand segment, meaning the retailer captures margin at every price point rather than just one.

Store brands now account for 25 to 30 percent of grocery units sold at these chains, and the margin differential versus national brands has been a meaningful driver of profitability even as food inflation has complicated the broader business.

What This Does to National Brands

For the brands sharing shelf space with a private label competitor, the consequences range from uncomfortable to existential, depending on the category.

The most immediate pressure is positional. Retailers control shelf placement, and as their own brands grow, the incentive to give national brands prime real estate diminishes. Products slide from eye level to ankle level. SKU counts get trimmed. In some categories, national brands that fail to maintain volume get delisted entirely.

The second pressure is financial. To retain prime placement, national brands pay slotting fees, and as store brands expand, the negotiating leverage shifts. The retailer now has an alternative to offer shoppers. The national brand needs the shelf more than the shelf needs the brand.

The third, and subtlest, pressure is perceptual. When Kirkland Signature batteries sit next to Duracell, made by the same factory, the brand premium becomes harder to justify. Consumers who experience the equivalence firsthand rarely forget it.

The threat varies sharply by category. Commodity goods, such as paper towels, dish soap, canned goods, and pantry basics, are the most vulnerable. The functional difference between a national brand and a store brand equivalent is often minimal, and price sensitivity is high. Premium, identity-driven categories are more resilient. Nobody buys private-label perfume as a status signal. Dyson doesn’t lose much sleep over a Costco competing vacuum. Stanley and Starbucks have built communities where the brand itself is part of the product’s value.

The Rebalancing of Retail Power

For most of the 20th century, retail power flowed toward the brands. The companies that built consumer desire: Procter & Gamble, Nestlé, Colgate, and Unilever effectively dictated shelf terms to retailers who needed their products. The late 20th century began shifting that balance as Walmart and then Amazon demonstrated what scale could do to supplier leverage.

Store brands represent the latest, and perhaps most structurally significant, shift in that balance. They give retailers not just scale leverage but category independence. The retailer no longer just sells brands; it competes with them. It has learned, often from the brands themselves, how to manufacture, market, and distribute, and it has done so while capturing the margin that previously went elsewhere.

The national brands that will survive this era are the ones that stand for something a retailer cannot replicate: a genuine innovation, a community, an identity, a service. Everything that is merely functional is, eventually, a cost to be optimized away.

New article every Tuesday.

Be Bold. Be Real. Be Anomalous.

Episode Description

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

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

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

But the way she arrived here wasn’t linear.

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

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

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

It started with a realization:

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

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

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

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

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

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

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

🎧 Listen to the Episode

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

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

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

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

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

• The importance of representation in both branding and product development

• How to build a team that truly understands your customer

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

• The reality of balancing entrepreneurship and motherhood

Favorite Quote

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

—Betty Friedan

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

Favorite Book

📖 Pachinko — Min Jin Lee

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

In This Episode, We Cover

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

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

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

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

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

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

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

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

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

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

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

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

Referenced in This Episode

K-beauty and global beauty standards

Melanin-rich skin and dermatology insights

Startup fundraising and early-stage strategy

Building a beauty brand from scratch

Representation in consumer brands

Entrepreneurship and motherhood

Global market expansion and cultural positioning

New episodes drop every Monday and Thursday.

Be Bold. Be Real. Be Anomalous.

I finished The Next Day by Melinda French Gates last night, and I haven’t been able to stop thinking about it.

The book touches on the end of marriage in two different stories. Once through death, and once through divorce. They’re not the same kind of loss; the pain is different, the aftermath is different, but in both, life continues. You move on. What stayed with me is how honestly she sits with that.

It got me thinking about my own culture. Divorce isn’t common where I come from (it’s becoming more accepted), slowly, but the older generation, especially, a lot of those marriages probably should have ended, but didn’t. Not because things were good, but because nobody wanted to put that on the family. I used to understand that reasoning. Now I’m not sure I agree with it. Staying in something that isn’t working isn’t protecting anyone, not the people in the marriage, not the people around it. I think choosing to leave, when that’s the right choice, takes its own kind of courage.

But honestly, what I kept coming back to wasn’t even about marriage specifically.

It’s this: you can’t lean too heavily on anyone. Not your husband, not your kids, not your friends. Not because they don’t matter, they do, but because people change. Everyone is, in some way, a passing cloud.

The only person who is always there is YOU.

So I keep coming back to this to find the quiet. Sit in it. Listen to yourself. What do you want? What are you feeling? What are you becoming? Because here’s the thing, even you change. You’re not the same person you were five years ago, and you won’t be the same person five years from now. So self-knowledge can’t be something you figure out once and set aside. It’s something you have to keep coming back to.

That’s what this week has been for me. A reminder to check back in with myself.

Methods to Find Yourself

I started thinking about what it actually means to check back in with yourself, as a practice. Something I can do regularly. Because the noise doesn’t stop on its own. The world doesn’t pause and say, take a moment, find yourself. You have to carve that out.

So here are the things I’m bringing into my life, as commitments.

Write

There is something that lives underneath your thoughts that you don’t know is there until you start writing. Journaling isn’t about documenting your day. It’s about excavating yourself. You put pen to paper, and things surface feelings you hadn’t named, patterns you hadn’t noticed, truths you’d been too busy to sit with. You don’t know what you actually think until you write it down.

Try it. You’ll surprise yourself.

Meditate

Meditation is another way to listen to yourself. Or maybe more accurately, a way to stay still. We are so used to moving, filling, doing. Meditation is the practice of stopping and just stopping the running. That capacity to just be to sit inside the quiet without immediately reaching for a distraction, is rarer than it sounds.

Read

Reading is solitude that doesn’t feel lonely. A good book pulls you out of the noise of your own life and somehow, in doing that, helps you see it more clearly. It slows things down. And right now, slowing down is exactly the point. It has transformed me.

Walk Without Distractions

Just walk out into nature. There is something about moving through the world in silence that shakes things loose. Some of the most honest conversations you will ever have are the ones you have with yourself on a quiet walk.

Sit in the Quiet

This one is the simplest and somehow the hardest. Just sit in the quiet. We have trained ourselves to fill every gap, to reach for something the moment stillness arrives. But the quiet is where you hear yourself. Really hear yourself. What you want. What you’re carrying. What you’ve been avoiding. It’s all in there.

What I’m Reading

The Next Day— Melinda French Gates(Finished)

I recommend this book; it’s an easy read. Personally, I found it enlightening to see how someone like her can embrace change and go through it so publicly. She has written about her experiences beautifully.

Everything Is Tuberculosis— John Green (Currently reading)

This book explores the history and global impact of tuberculosis (TB). The book explains how TB has shaped societies, medicine, and public health, while also highlighting the inequalities that affect who gets treated and who doesn’t. Excited to dive in.

What Else Dropped This Week

Off Script

How Priya Built Punar with Purpose — and Took It to the Oscars

How to Turn Strategy Into Action, Natalie Trotta on Building a Consulting Career

Under the Hood

The Art of the Brand Collab: Why Some Partnerships Work and Others Blow Up

On My Reading Desk

1. Every AI gives you the same answer—that should worry you

2. How Apple became Apple: The definitive oral history of the company’s earliest days

3. AI is creating the first generation of cognitively outsourced humans

4. How This Founder Grew Her Brand’s TikTok Shop Revenue 10x in Just 1 Year

Note to My Future Self

No matter what happens, no matter what ends, what changes, what catches you off guard, you have to move forward. That part isn’t a choice. But whether you move forward knowing yourself, whether you stay connected to who you are along the way, that part is entirely up to you.

I’d rather move forward with myself than leave myself behind in the process.

Be bold. Be real. Be Anomalous.

— Sai Menon

One of the biggest ways to access customers from two different worlds is through brand colloboration and it is the age-old marketing technique used by business owners of any size. While I was recently reading an article about Glow Recipe's collaboration with Beautyblender, it got me thinking which collabs work and which don’t. What are some of the principles to follow?

How a collab actually works

Think of it like a strategic friendship with a purpose.

When two brands collaborate, they’re essentially saying: you have something I don’t, and I have something you don’t, so let’s combine them, and both come out ahead. That something could be an audience, a distribution network, a technology, a reputation, or simply a cultural moment.

At its most basic level, a brand collab is a value exchange.

What makes it different from just buying what you need is that a collab keeps both brands intact and independent. You’re borrowing each other’s strengths for a defined period, for a defined purpose, and then you each walk away having grown.

The business mechanics that sit underneath that simple idea are contracts, IP ownership, revenue splits, exclusivity terms, and exit clauses. But the instinct that drives the best collabs is much simpler: find a partner whose strengths fill your gaps, make sure your strengths fill theirs, and build something neither of you could have built alone.

6 Types of Brand Collaborations

1. Co-created products: Brands design and launch something new together.

2. Joint marketing campaigns: Brands team up on shared promotions to reach a wider audience.

3. Sponsorships: One brand supports another’s event or initiative for visibility.

4. Content collaborations: Brands create content together to engage their audiences.

5. Licensing agreements: One brand allows another to use its IP for co-branded products.

6. Influencer partnerships: Brands work with influencers to build trust and reach.

Two that got it right

Nike + Apple: when hardware meets movement

In 2006, Nike and Apple released Nike+, a sensor embedded in a shoe that synced with an iPod to track your run. It sounds obvious in retrospect, but at the time it was genuinely new: a sports brand and a tech company creating an entirely new product category together.

The partnership worked because the audience overlap was precise, athletes who were already buying both brands, and because each company contributed something the other couldn’t replicate on its own. Nike knew runners. Apple knew software and hardware miniaturization. The result wasn’t a logo slapped on a limited-edition sneaker; it was a product that changed how millions of people exercise. It eventually evolved into the Apple Watch’s core fitness identity.

The lesson: the best collabs create something that genuinely wouldn’t exist without both parties.

Doritos + Taco Bell: a billion tacos

When Taco Bell and Frito-Lay launched the Doritos Locos Taco in 2012, it became one of the fastest-selling items in fast-food history, with over 1 billion units sold in the first year. The premise was almost comically simple: replace the taco shell with a Doritos chip. And internally, it was met with plenty of skepticism. Executives questioned whether the idea was too gimmicky, too niche, too weird for mainstream America.

Development was a grind; it reportedly took three years just to get the shell right, with engineers struggling to transfer the Doritos’ signature dust coating onto a taco shell without it crumbling or flaking off.

But it beat every odd stacked against it. It worked because the brands occupied the same moment in a person’s life. Taco Bell and Doritos are both late-night, casual, unapologetically flavor-forward. The product also created a new reason to visit Taco Bell at all, meaning both brands drove traffic to each other without cannibalizing anything. What looked like a stunt turned out to be one of the most successful food collaborations in history.

The lesson: the most unlikely-sounding collabs can outperform the safe, polished ones because when the fit is instinctively right, customers don't need to be convinced. They just get it.

Two that fell apart

Starbucks + Kraft: the billion-dollar breakup

In 1998, Starbucks partnered with Kraft to distribute its packaged coffee into grocery stores across America. By most measures, it worked. Kraft was good at distribution, sales grew, and Starbucks coffee found its way into millions of homes. But by 2010, Starbucks had outgrown the arrangement and wanted to control its own consumer packaged goods future. So it walked away from the contract early. Kraft refused to go quietly and sued. In 2013, an arbitrator sided with Kraft and ordered Starbucks to pay $2.76 billion, one of the largest contract dispute payouts in consumer goods history.

The lesson: a collab that works commercially can still end in disaster if the exit isn’t handled right. Always know how you’re getting out before you sign on how you’re getting in.

Gap + Kanye West: the deal without guardrails

In 2020, Gap and Kanye West (now legally Ye) announced Yeezy Gap, a high-profile partnership meant to reinvent Gap’s relevance and bring Ye’s design vision to a mass audience. It collapsed in 2022 amid public disputes, missed timelines, and a breakdown in the relationship, culminating in Ye making increasingly erratic and harmful public statements.

The failure had multiple dimensions. Structurally, the deal gave enormous creative control to a single individual with no formal accountability mechanisms for reputational risk, no morals clause with real teeth, and no contingency plan. When Ye’s public conduct became brand-toxic, Gap was stuck. There was also a fundamental tension between Ye’s instinct to create scarcity and chaos (products dropped in garbage bags, delayed releases) and Gap’s need to run a predictable retail operation.

The lesson: always include an exit. Any deal involving a single personality needs contractual protection against the possibility that the person becomes a liability.

Conclusion

Successful collaborations are the ones that truly understand how customers think and shop—and make that experience easier. But for that to happen, the partnership has to be intentional and well thought out, especially in a time when technology and consumer behavior are constantly evolving.

For more in-depth analysis, stay tuned.

New Article drops every Tuesday.

Be Bold. Be Real. Be Anomalous.

Episode Description

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

Priya’s journey is anything but linear.

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

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

It began with a question.

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

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

But this conversation goes far beyond sustainability.

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

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

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

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

🎧 Listen to the Episode:

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

• How curiosity can turn into a business

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

• The realities of building a sustainable brand from scratch

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

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

• How flexibility in execution can unlock unexpected opportunities

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

• Why ethical and sustainable businesses require both conviction and strategy

Favorite Quote

“Everything you seek is inside of you.”

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

Favorite Book

📖 Atomic Habits — James Clear

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

In This Episode, We Cover

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

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

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

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

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

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

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

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

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

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

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

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

Referenced in This Episode

• Sustainable fashion and textile waste

• Ethical production and circular design

• Gender inequality in tech and entrepreneurship

• Founder mindset and resilience

• Building mission-driven brands

• Community and collaboration in business

Resources Priya Mentioned in This Episode

• United Nations Sustainable Development Goals (SDGs)

• Founder communities and women-led business networks

New episodes drop every Monday and Thursday.

Be Bold. Be Real. Be Anomalous.

Act I: The pitch that started everything

Emma Grede didn’t have the birth lottery. Raised by a single mother in East London, she saved wages from a paper route to buy fashion magazines, glossy, airbrushed worlds that felt a million miles from her own life. But instead of being bitter about that gap, she became obsessed with it.

At 26, she founded ITB Worldwide, her own entertainment marketing agency in London. Over the next decade, she built relationships with some of the biggest names in fashion and entertainment and eventually relocated to Los Angeles, where an opportunity of a lifetime awaited.

In 2015, at Paris Fashion Week, she was introduced to Kris Jenner. She fixed a meeting, and Emma walked in with a single, focused idea.

“I wanted to take a pain product something women genuinely struggled with and solve it. Denim was that product.”

She pitched the idea to Khloé Kardashian, and something clicked immediately. “I pitched her that idea and a light bulb went off in her head, and she literally finished my sentences,” Emma recalled. “I knew in that moment that Khloé was the person I wanted to work with.”

Two women from very different worlds found themselves finishing each other’s sentences over a shared frustration. That alignment was the seed of everything that followed.

Act II: The launch that broke records

Before Good American officially launched in October 2016, Emma and Khloé hosted a casting call at Milk Studios in New York. They hoped maybe 10 women would show up. Around 5,000 came.

That wasn’t a fluke. It was a signal and proof that the market they were targeting was enormous, underserved, and hungry.

On launch day, Good American went live online and at select Nordstrom locations. In the first hour, they recorded $1 million in sales. By the end of the day, another million. It was the largest denim launch in history.

$1 million in the first hour. The largest denim launch in history.

This was a well-thought-out strategy. It was a brand that had identified a real problem, built a genuine message around it, and showed up with the receipts to prove they meant it. Good American launched with sizes 00 through 24, the widest range in the industry at the time.

Act III: The order they said no to

Within weeks of launch, a major retailer came calling with a significant wholesale deal. It could have accelerated the brand’s growth overnight.

There was one condition: they would only carry sizes 0 through 8.

Emma and Khloé said no.

Before working with any retail partner, they had established a non-negotiable rule: any store that carried Good American had to stock its full-size range and display it in one place, with no separate “plus-size” floor.

“We’re going to have a company based on a set of principles, because we don’t want to negotiate every step of the way.”

For a brand that was just weeks old, turning down a major retailer was a genuinely scary decision. But it told the world and its customers exactly who Good American was. When they said they were inclusive, they were backing it up with actual business decisions that cost them real money.

Act IV: From jeans to a movement

After launch, the founders studied their data obsessively. In 2018, they noticed that 50% of their returns were coming from customers in sizes 14 and 16. The fashion industry had historically jumped from 14 to 16, leaving a gap.

Good American created a size 15.

That decision illustrates something profound about how they operated: they listened to what customers were telling them through their behavior, not just their words. They responded with a product solution.

That same year, they expanded beyond denim into activewear and ready-to-wear. The brand expanded its retail footprint to include Nordstrom, Saks, Bloomingdale’s, Anthropologie, and H&M. In 2023, it opened its first physical store at Westfield Century City in Los Angeles.

Today, Good American employs 120 people and generates over $200 million in annual revenue.

The real lesson from Good American

Here’s what most people get wrong when they study a brand like Good American: they look at the outcome and reverse-engineer a fairy tale.

Had a celebrity co-founder, a perfect launch, which would lead to a multi-million dollar business. But that’s not what happened. What actually happened was messier, slower, and far more instructive. A retailer said no to the full-size range, and they walked. Khloe Kardashian gradually stepped back from promotion, and they built anyway. A category expansion didn’t land the way they expected, and they went deeper into their product instead of wider into hype. And when the business hit walls, Emma Grede did what she had always done: got closer to the customer and let the data show her what to do next.

“I didn’t know what could go wrong and so I just got on with things that right now would seem scary or stupid.” -Emma Grede

You will make the wrong bets. You will expand too fast into a category your customers aren’t ready for. You will rely on something, a platform, a person, a moment of trend, that eventually shifts. Every brand makes these mistakes. The ones that survive aren’t the ones that avoided those mistakes. They’re the ones that built something real enough underneath to outlast them.

You need to be like Emma Grede, the one who knows the customer, holds the line, and keeps building long after the glamour of day one has faded.

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

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

But the way she arrived there wasn’t linear.

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

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

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

But this conversation goes far beyond career milestones.

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

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

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

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

🎧 Listen to the Episode

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

• Why nonlinear careers can become a strategic advantage

• How to translate big ideas into real execution

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

• How Natalie built her consulting business through relationships and network

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

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

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

• Why quitting the wrong things can unlock real progress

Favorite Quote

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

— Maya Angelou

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

Favorite Books

📖 Quit — Annie Duke

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

📖 Big Magic — Elizabeth Gilbert

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

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

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

In This Episode, We Cover

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

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

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

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

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

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

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

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

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

(47:00) Reframing failure and learning from uncertainty

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

Referenced in This Episode

• Consulting and founder strategy

• MBA career paths and executive education

• Startup and founder productivity systems

• Career pivots across industries

• Building a consulting business

• Time management for entrepreneurs

New episodes drop every Monday and Thursday.

Be Bold. Be Real. Be Anomalous.

This week, one question kept sitting with me:

how much discipline and consistency is actually normal?

It started with a post I came across online. Someone had written that sticking to a routine at every moment is neurotic. And honestly? A younger version of me would have agreed.

There was a time when I saw structure as a kind of rigidity. Something that got in the way of being spontaneous, or flexible, or just easy to be around. So when the late night came around, I’d stay. When someone needed me to show up somewhere I hadn’t planned for, I’d rearrange. When the choice was between my early morning and someone else’s comfort, I usually chose theirs.

Each compromise felt small. Collectively, they added up to something I didn’t have a name for at the time. Now I do:

I was consistently putting myself last and calling it being easygoing.

Protecting My Habits

The habits were always there. Protecting them was the hard part.

Waking up early. Sleeping early. Eating well. Moving my body. Simple things, but they require guarding. And guarding them comes at a social cost.

Being disciplined means being the person who says, “I can’t make it, I have to be up early for my workout.” It means declining invitations. Being unavailable. Sometimes being misunderstood. And when you’re younger, that friction feels too expensive.

So you give in. You show up to things you hadn’t planned for. You skip the workout to prove you’re not rigid. You break the sleep schedule so no one thinks you’re antisocial. And each time, it feels like a small sacrifice for the sake of the relationship, not a pattern.

But it is a pattern.

If I can show up for other people without question — rearrange my day, lose sleep, push through why can’t I show up for myself with that same reliability?

We extend enormous grace to others. We honor their time, their events, their needs. We rarely question it. But the commitments we make to ourselves? Those are the first ones to go.

That asymmetry stopped making sense to me. And once I saw it, I couldn’t unsee it.

Skipping an event to stick to your routine is not antisocial. It’s self-respect.

I don’t mean this as an excuse to be rigid or unavailable. I mean it literally: keeping a promise to yourself is an act of respect toward yourself.

People who don’t have structure often find it threatening in others. Not maliciously, but your consistency holds up a mirror they weren’t ready to look into.

You don’t owe anyone an explanation for going to sleep early. You don’t need to justify prioritizing your health. And you don’t need to frame your own self-care as an inconvenience and then apologize for it.

What I’m Reading

10% Happier - Dan Harris(Currently Reading)

The book follows journalist Dan Harris after a live-TV panic attack prompts him to explore meditation and mindfulness. He shows that training your attention helps quiet the constant chatter in your mind, making you calmer and slightly happier about “10% happier.

This American Woman - Zarna Garg (Currently Reading)

The memoir is a sharp, funny, and deeply personal reflection on identity, resilience, and what it means to claim your own voice in a country where you’re constantly told who you’re supposed to be.

What Else Dropped This Week

Off Script

How Shai, One of the Youngest U.S. Diplomats, Became a Startup Founder

Under the Hood

You Don’t Need VC Money. You Might Need VC Money. Here’s the Truth.

On My Reading Desk

1. Forget KPIs: Vibes, community, and culture are how to build a brand in 2026

2. Adobe CEO to Step Down as Company Faces Intensifying AI Battle

3. Create & Cultivate Founder Jaclyn Johnson Opens Up About the Hidden Costs of Scaling Too Fast

4. Replit CEO Says Its New AI Agent Can Vibe Code a Startup From Scratch

Note to My Future Self

Discipline is not the enemy of freedom. It is the structure that makes freedom possible.

And the next time someone implies your consistency is excessive — pause and ask yourself: who does agreeing with them actually serve?

You showing up for yourself is not neurotic. It never was.

Be bold. Be real. Be Anomalous.

— Sai Menon

Thanks for reading this week’s debrief. If this resonated, share it with someone who needs the reminder

Four brands. Two paths. One question worth answering.

There’s a war of narratives in the startup world.

On one side: “Bootstrapping is freedom. VCs will ruin your vision. Build slow, build real.”

On the other: “You need capital to win. Without funding, you’re bringing a knife to a gunfight.”

Both camps have followers for their own reasons. Both camps have horror stories. And both camps, it turns out, have genuinely iconic success stories.

So instead of picking a side, let’s look at the evidence: four brands that built something remarkable, and what their funding path actually meant for how they got there.

The Bootstrapped Brands

1. Mailchimp — The $12 Billion “Failure” to Take VC Money

In 2021, Intuit acquired Mailchimp for approximately $12 billion. The founders, Ben Chestnut and Dan Kurzius, owned the entire company. They had never taken a dollar of outside investment.

Let that sink in.

Mailchimp started in 2001 as a side project. A web design agency needed an email tool for small-business clients, so they developed one. It stayed a side project for years. They were profitable almost immediately because they had to be. There was no runway to burn.

The turning point came in 2009, when they introduced a freemium model, offering up to 500 subscribers for free. Signups exploded. By 2012, they were sending 10 billion emails per month. By 2019, they hit $700 million in annual revenue.

What bootstrapping forced them to do:

• Focus obsessively on the customer, not the pitch deck

• Stay profitable at every stage, making them resilient during downturns

• Own their product decisions completely, no board telling them to “move upmarket” or chase enterprise

• Build at a pace that lets culture develop organically

Chestnut has said that not taking VC money meant they could serve small businesses, the “little guys”, without pressure to abandon them for higher-margin enterprise clients. That customer loyalty became a moat.

The irony? Many VC-backed competitors with greater resources (Campaign Monitor, Constant Contact) never caught up to them.

The lesson: Constraints create clarity. When you can’t outspend, you have to out-think.

2. Spanx — From $5,000 to a Billion-Dollar Brand, Alone

Sara Blakely started Spanx in 2000 with $5,000 in personal savings, a patent she filed herself after reading a book on patents, and a cold-calling hustle that would make most salespeople quit.

She was selling fax machines door-to-door when she had the idea. She couldn’t afford to hire a lawyer, so she wrote the patent herself. She couldn’t afford a PR firm, so she drove to Neiman Marcus, asked for 10 minutes, and convinced a buyer to stock the product in the room.

For the first two years, she ran the company entirely alone, taking orders, packing boxes, handling returns, and doing her own PR.

By 2012, she was on the cover of Forbes as the world’s youngest self-made female billionaire. Spanx was valued at over $1 billion. She still owned 100% of the company.

She finally received outside investment in 2021, a private equity deal with Blackstone that valued Spanx at $1.2 billion, only after two decades of building entirely on her own terms.

What bootstrapping forced her to do:

• Get creative with marketing (she mailed her product to Oprah’s team with a handwritten note, Oprah featured it as a “Favorite Thing”)

• Stay deeply close to the product and customer because she was the only one working on it

• Make every hire count, every dollar matters

• Prove the concept with real revenue before scaling

Blakely didn’t raise money because no one would give it to her at first. She has said investors didn’t take her seriously. So she just... kept going.

The lesson: Sometimes the “no” is a gift. Rejection from capital markets forces you to find validation where it actually matters, from customers.

The VC-Backed Brands

3. Airbnb — How $600K Saved a Company That Sold Cereal to Survive

Before Airbnb became a $75 billion company, the founders were selling novelty cereal boxes to pay rent.

Brian Chesky and Joe Gebbia were so financially constrained that they created “Obama O’s” and “Cap’n McCain’s” limited-edition cereal boxes tied to the 2008 presidential election and sold them for $40 per box to fund the company. They raised approximately $30,000 from cereal sales. That money kept Airbnb alive long enough to get into Y Combinator.

Y Combinator invested $20,000 in early 2009. Sequoia and others followed. But the most important capital came from Andreessen Horowitz, which led a $7.2 million Series A in 2010, the round that enabled Airbnb to move from “interesting experiment” to “real company.”

The funding didn’t just buy them time. It bought them:

• The ability to fight Wimdu, a Rocket Internet clone in Europe that was trying to outspend and out-hustle them internationally

• Introductions to key operators, legal resources, and industry contacts

• The credibility to attract world-class engineers when competing with Google and Facebook for talent

• Speed in a marketplace business, getting to liquidity (enough hosts AND guests) is an existential race

Here’s what’s critical to understand about Airbnb and VC: the business model required scale to work. A marketplace with 200 listings is nearly worthless. With 4 million listings, it’s irreplaceable. The network effects required capital to reach escape velocity — bootstrapping would have meant building too slowly in a market where speed was survival.

Airbnb IPO’d in December 2020 at a valuation of $47 billion, closing its first trading day at over $100 billion. Total VC invested: roughly $6 billion over the company’s life.

The lesson: In marketplace and network-effect businesses, capital isn’t optional; it’s the driver.

4. Glossier — Building a Beauty Empire on Community and Capital

Emily Weiss launched Into The Gloss, a beauty blog, in 2010. It became a cult hit. In 2014, she raised $2 million in seed funding to launch Glossier — a direct-to-consumer beauty brand built on one radical idea: let customers co-create the products.

This wasn’t just marketing. Weiss and her team would post the question, “What do you want in a moisturizer?” to their community and then compile the responses. Product development driven by comment sections.

But here’s where the VC money mattered:

• An $8.4 million Series A in 2015 let them invest in product development and build a real supply chain

• A $24 million Series B in 2016 funded the kind of experiential retail and content that felt organic but cost real money to execute

• By their Series D in 2019, Glossier was valued at $1.2 billion, and the capital allowed them to launch in new markets and categories

Glossier’s product is inseparable from its community, but the community required content, channels, and physical experiences to remain viable—that cost money. The brand could not have been bootstrapped to the same scale because its identity was the scale. Being everywhere, being cultural that takes capital.

The company experienced a rough patch in 2022 (layoffs, a leadership reset), which is worth noting: VC-backed companies can grow faster, but they can also overcorrect, overhire, and face pressure to justify their valuations in ways bootstrapped companies never do.

Still, Glossier redefined what a beauty brand could be, built a genuine community of millions, and created a template that every DTC brand since has tried to copy.

The lesson: When your brand is the community, and community requires content and presence at scale, capital accelerates the flywheel.

So: Bootstrap or Raise?

Here’s the honest synthesis:

Bootstrap when:

• Your business can be profitable quickly (SaaS, services, CPG at a small scale)

• You’re solving a problem that doesn’t require network effects

• Optionality and ownership matter more to you than speed

• You want to serve a customer segment that VCs might pressure you to abandon

• You’d rather build a $100M business you own than chase a billion-dollar outcome you might not

Raise when:

• You’re building a marketplace, platform, or network — where scale IS the product

• You’re in a winner-take-most market where being second means being irrelevant

• The window of opportunity is genuinely time-limited (regulatory, technological, cultural)

• The capital will buy you asymmetric leverage, not just runway

The brands above didn’t succeed because of their funding path. They succeeded because their funding model aligned with their business model and ambitions.

Mailchimp didn’t need VC money because it could grow sustainably with customer revenue. Airbnb absolutely needed it because it was in an existential race with copycats who had unlimited capital.

The worst outcome isn’t choosing wrong between bootstrap and VC. It’s taking VC money for a business that didn’t need it (and losing ownership and control for no reason), or refusing capital for a business that did (and losing to a well-funded competitor while being philosophically pure).

Know your business. Know your market. Then choose accordingly.

If this was useful, share it with one founder who’s wrestling with this decision right now. It might be the most important choice they make.

New Article every Tuesday.

Be Bold. Be Real. Be Anomalous.

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

Shai’s path is anything but conventional.

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

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

It began much closer to home.

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

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

But this conversation goes far beyond startups.

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

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

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

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

🎧 Listen to the Episode:

[Spotify] | [Apple] | [YouTube]

What You’ll Learn

• Why empathy can be a founder’s greatest advantage

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

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

• How personal problems can reveal massive market opportunities

• Why navigating broken systems often leads to innovation

• How cross-cultural experiences shape leadership and communication

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

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

Favorite Quote

“Your vibe attracts your tribe.”

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

Favorite Book

📖 Parable of the Sower — Octavia E. Butler

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

In This Episode, We Cover

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

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

(12:00) Representing the United States abroad

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

(28:00) Leaving diplomacy and exploring new paths

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

(42:00) Building Carelumi and solving credentialing problems

(50:00) What founders should understand about AI

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

Referenced in This Episode

• Healthcare credentialing and insurance systems

• AI and automation in healthcare

• Cross-cultural leadership

• Founder of empathy and lived experience

• The future of work in an AI-driven world

• Building companies from personal problems

Resources Shai Mentioned in This Episode

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

• U.S. diplomat career tracks

• Perplexity Comet Link

• Gemini Pro (free for students)

• Granola AI Meeting Notes

• Vercel (alternative to Lovable)

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

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

New episodes drop every Monday and Tuesday.

Be Bold. Be Real. Be Anomalous.

This week, a question has been sitting with me, the way a pebble in a shoe makes itself known on a long walk. How much of who I am today is actually me?

We are born, arguably, the most ourselves we will ever be. Unfiltered. Unapologetic. Loud when hungry, soft when held. And then slowly, gently, relentlessly, the world begins its work on us.

It starts with parents. The first mirrors we are ever handed. Their fears become our caution. Their love languages become our emotional vocabulary. Their silences teach us what is too heavy to name. We absorb so much before we even have words for what we’re absorbing.

Then come friends, the ones who laugh at your jokes and teach you which version of yourself is worth performing. Partners who soften certain edges and sharpen others. Children who demand a kind of selflessness that quietly, permanently rewrites you. Each relationship is a new layer. Each layer is a small departure from whoever you were before.

How much of who we are today is us and how much is the accumulated sediment of everyone who has ever loved us, needed us, or shaped us?

The Archaeology of Self

Think of identity like layers of sediment. Each year, each relationship, each role we take on, parent, partner, daughter, colleague, deposits something new. And here’s what unsettles me: the original rock, the bedrock self, becomes harder and harder to reach.

The influences arrive uninvited and often unnamed.

Parents. Friends. Partners. Children. Workplaces. Culture. Time. Grief.

None of these are villains. This is not a story about damage. It is a story about permeability, the fact that we are, by nature, porous creatures. We seep into each other. We take on the colours of the rooms we spend the most time in.

Is the Chipping a Loss or a Becoming?

Part of me mourns it. The girl who had opinions before she had an audience. The version of me that hadn’t yet learned to edit herself before speaking. There’s something in that unguarded self that feels like the truest version, or at least the most original one.

But another part of me wonders if the chipping is the point. A sculptor doesn’t ruin a block of marble by chipping at it; they reveal something. Maybe the people in our lives are doing the same. Not taking from us, but uncovering us. Even when it hurts.

Perhaps we don’t disappear into the people we love. Perhaps we expand into them and lose track of where we end.

Still. There is value in the audit. In pausing long enough to ask:

Which parts of me feel chosen? Which parts feel inherited? Which parts would I keep, if I were starting from scratch?

Identity isn’t a fixed object to protect. But it isn’t nothing, either. Somewhere between the self we were born as and the self that’s been shaped by decades of love and loss and compromise, there is a thread. A continuous note running through all the versions.

This week, I’m just trying to listen for it.

What I’m Reading

Mattering- Jennifer Breheny Wallace (Finished)

Mattering examines how the need to feel significant shapes our ambition, relationships, and identity, and why true confidence comes from knowing we matter beyond achievement.

10% Happier - (Currently Reading

The book follows journalist Dan Harris after a live TV panic attack leads him to explore meditation and mindfulness. He shows that training your attention helps quiet the constant chatter in your mind, making you calmer and slightly happier about “10% happier.

What Else Dropped This Week

Under the Hood

How to Think About Funding Your Business: A Founder’s Guide

Skin Deep

The Beginner’s Guide to Moisturizing: Everything You Need to Know to Start Your Skincare Journey

On My Reading Desk

1. The Estée Lauder Companies and Forest Essentials to Enter a New Chapter in Their Long-Term Partnership

2. Brands Are Ditching Purpose. Rare Beauty Is Doubling Down—and Winning

3. This CEO explains what’s really behind layoffs—and it’s not AI

4. Jamie Dimon Says These ‘Dumb Things’ in Our Current Economy Could Point to Another Financial Crisis

Note to My Future Self

There will always be people who come into your life, and there will always be reasons they do.

Let them in. Let them change you in the ways that matter.

But hold on, quietly and firmly, to the part of you that existed before any of them arrived. The part that is not a reflection of someone else's needs, not a response to someone else's presence.

The part that is just “YOU”. That part is worth protecting.

Don't let it get so buried under layers of love and adaptation that you forget it's still there. It is. It always has been. Keep it close.

Be bold. Be real. Be Anomalous.

— Sai Menon

The money you take and how you take it shape everything from your daily decisions to your eventual exit. Here’s how to think clearly about the options.

The Question Nobody Tells You to Ask First

Most first-time founders frame the fundraising question as:

“How do I raise money?”

The better question is:

“What kind of company am I building and what kind of money fits that?”

Funding is not a prize. It’s a tool. And like any tool, the wrong one for the job causes damage. A venture-backed founder building a lifestyle business will feel the walls closing in. A bootstrapped founder competing in a winner-take-all market may lose before they get a chance to compete. Understanding the landscape clearly, without hype, is the first real job of a new entrepreneur.

The Funding Spectrum

Think of startup funding not as two camps (VC vs. bootstrapping) but as a spectrum of trade-offs along three axes:

• Control — How much say do you keep over decisions?

• Speed — How fast can you grow and hire?

• Obligation — Who do you owe, and what happens if things go sideways?

Here’s a breakdown of the main paths, from most autonomous to most capital-intensive.

1. Bootstrapping — Building on Your Own Terms

What it is: You fund the company from your own savings, early revenue, or a combination of the two. No outside investors. No board telling you what to do.

The upside:

• Full ownership. Every dollar of value you create stays yours.

• Decisions are yours alone. You can pivot, pause, or change direction without a board vote.

• Forces discipline. Constraints breed creativity. Bootstrapped founders tend to become excellent at unit economics early.

The downside:

• Slow by design. You can only grow as fast as revenue allows.

• Personal financial risk. If you’re funding from savings, a failed year hits your household.

• Some markets simply require capital to compete. You can’t bootstrap your way into semiconductor manufacturing.

Real example: Basecamp (formerly 37signals) is the canonical bootstrapping success story. Jason Fried and David Heinemeier Hansson built a profitable, product-focused company without ever taking VC money and have been vocal about why. Their software business generates tens of millions in revenue with a small team and no pressure to exit or grow beyond what feels right.

Contrast that with a founder who bootstrapped an e-commerce brand, grew it to $2M in revenue, but couldn’t afford the inventory to fulfill a major retail partnership. The opportunity expired. A small outside investment could have changed the outcome.

Best for: Service businesses, SaaS with modest acquisition costs, niche products with loyal customers, founders who prize autonomy and sustainable growth over speed.

2. Friends, Family & Angels — The First Outside Capital

What it is: Money from people who believe in you as much as they believe in the idea. Angels are typically high-net-worth individuals who invest their own money in early-stage companies.

The upside:

• Faster and less formal than institutional fundraising.

• Angels often bring mentorship, introductions, and operational experience.

• Terms can be founder-friendly (especially at pre-seed, using instruments like SAFEs or convertible notes that delay valuation negotiations).

The downside:

• Friends and family money carries emotional weight. A bad quarter isn’t just a business problem; it’s Thanksgiving dinner.

• Angels vary wildly. A great angel adds real value. A bad one calls you every week asking for updates.

• Amounts are typically modest ($25K–$500K), which may not be enough for capital-intensive models.

Real example: When Jeff Bezos left his Wall Street job to start Amazon in 1995, his parents, Mike and Jackie Bezos, wrote him a check for roughly $250,000, money they'd saved over a lifetime. They knew they might lose it all. That's the defining feature of friends and family capital: it's backed by belief in the person, not a financial model. Amazon went on to become one of the most valuable companies in history, but for every Bezos, there are founders whose parents lost that money quietly. The stakes are personal in a way no term sheet can capture.

Best for: Very early validation, pre-product founders, businesses where $100K–$500K is enough to reach meaningful milestones.

3. Revenue-Based Financing (Borrowing Against Your Future Revenue)

What it is: A lender gives you capital today; you repay it as a percentage of monthly revenue until you’ve paid back a fixed multiple (typically 1.2x–2x the loan). No equity given up.

The upside:

• No dilution. You keep full ownership.

• Repayment flexes with your business's slow month, smaller payment.

• Faster than traditional bank loans, no collateral required (usually).

The downside:

• Only works if you have predictable, recurring revenue already.

• The effective interest rate can be high if you repay quickly.

• Not for pre-revenue or early-stage companies.

Real example: Wing, a marketplace for virtual assistant services, took $500K in revenue-based financing from Efficient Capital Labs in 2023 and put it directly into marketing. The result: 210% annualized growth in the months that followed without giving up a single share of equity. It's a quiet success story, which is fitting. RBF tends to work best for exactly this kind of company: real revenue, a clear growth lever, and no need to hand a board seat to someone to pull it.

Best for: E-commerce, SaaS, media, and any business with recurring or predictable revenue that needs fuel for growth, not for product development.

4. Venture Capital — Rocket Fuel With a Clock Attached

What it is: Institutional funds (managing money from university endowments, pension funds, wealthy families) invest in exchange for equity in your company. They expect one or more companies in their portfolio to return the entire fund, which means they need outcomes of 50x–100x.

The upside:

• Large checks ($500K to $50M+) that allow aggressive hiring, marketing, and expansion.

• The best VCs are genuinely helpful, pattern-matched on hundreds of companies, with networks that open doors.

• A strong VC brand (a16z, Sequoia, Benchmark) can attract talent and customers who take signals from investor reputation.

The downside:

• You are now on the VC’s timeline, not your own. They have 10-year fund cycles and need exits.

• Dilution is real and compounds. After a seed round, Series A, and Series B, founders often own 15–30% of their own company.

• VC is optimized for one outcome: a very large exit (IPO or acquisition). A $20M profitable business is often considered a failure by a VC fund — not by you, but by the structure of the deal.

• Board dynamics change. Disagreements over strategy, hiring, or pace can become existential.

Real example: WeWork is the cautionary tale. Masayoshi Son’s SoftBank poured billions into Adam Neumann’s vision of “physical social networks.” The money allowed WeWork to expand recklessly, subsidizing growth that masked terrible unit economics. When the IPO window opened, the scrutiny revealed a business that couldn’t survive without continuous capital infusion. Neumann walked away with hundreds of millions; thousands of employees lost jobs.

On the other side: Stripe. The Collison brothers took venture money but were disciplined in how they deployed it. They built real infrastructure, prioritized developer experience, and grew into genuine dominance. VC accelerated something that was already working.

Best for: Companies in large, winner-take-all markets where speed is a competitive moat — fintech, marketplaces, enterprise software, biotech.

5. Small Business Loans & SBA Financing

What it is: Traditional bank lending, often backed by the U.S. Small Business Administration (SBA), which reduces lender risk and enables better terms for borrowers.

The upside:

• No equity given up. This is debt, not dilution.

• SBA loans can offer low interest rates and long repayment terms.

• Works for businesses that don’t fit the VC mold — restaurants, retail, trades, professional services.

The downside:

• Requires personal guarantee in many cases. Your house may be collateral.

• Slow process; weeks to months.

• Requires some operating history; hard to access at the idea stage.

Real example: Thousands of Main Street businesses, bakeries, plumbing companies, and dental practices are built with SBA loans. This is the backbone of small business America, and it works well for businesses that generate consistent cash flow and don’t need to scale to $100M to be meaningful and profitable.

Best for: Established small businesses, franchise expansion, asset-heavy businesses, and professional service firms.

The Mental Framework: Three Questions Before You Decide

Before choosing a funding path, every first-time founder should sit with these three questions:

1. What does “winning” look like for me? A $5M lifestyle business that funds a great life is a completely legitimate goal. So is building the next Stripe. But they require different capital strategies. VC optimizes for the latter. Bootstrapping preserves the former.

2. How big is the market, and how fast does it move? In markets where speed creates a defensible moat, where the first mover captures most of the value, slow capital is a liability. In stable, fragmented markets, patience is a competitive advantage.

3. What happens if I’m wrong? VC money has expectations baked in. If you take $5M and the company doesn’t grow into a $50M+ outcome, you’ll face pressure to sell at an uncomfortable time, or worse, watch the company shut down because it’s too small for a VC exit but too leveraged to survive as a small business. Bootstrapping’s failure mode is slower and more recoverable.

A Note on the Hybrid Path

Many successful companies don’t pick one lane and stay in it. They bootstrap to product-market fit, then raise a small angel or seed round to accelerate distribution, then raise a Series A only when the model is proven, and the capital will compound.

This sequencing validates before you scale, protects founders from the most common funding mistake: using other people’s money to determine whether the idea works.

The Bottom Line

There is no universally correct answer. The best funding path is the one that matches your market, your goals, your personal risk tolerance, and the stage your business is actually in, not the stage you hope it’s in.

Venture capital is not a status symbol. Bootstrapping is not a consolation prize. Revenue-based financing is not a crutch. Each is a tool, shaped for a specific job.

The founders who navigate this well are the ones who understood what they were building before they decided how to pay for it.

New Article every Tuesday.

Be Bold. Be Real. Be Anomalous.

There’s a phrase we’ve all heard at some point: live like today is your last day. It sounds motivating on the surface, but when you really sit with it, it falls apart. If today were truly your last day, most of us wouldn’t be doing much of anything productive. We’d be in a panic, calling people we’ve lost touch with, abandoning every responsibility, and probably eating a ridiculous amount of dessert. That’s not living, that’s reacting.

This week has been a reminder of a different kind of philosophy. Not everything-on-fire urgency of “last day” thinking, but something more grounded and more powerful: do what you can today, because you don’t know what tomorrow holds.

The Procrastination Trap

Let’s be honest, procrastination is one of the easiest habits to fall into, and one of the hardest to shake. There’s always a reason to wait. You’re tired. You’re not in the mood. The task will still be there tomorrow. And sometimes, that’s true. But sometimes, tomorrow looks nothing like you expected.

You might wake up with the flu. A family emergency might call you away. Life has a way of rearranging your carefully laid plans without asking for permission. The small things you kept pushing, the email you meant to send, the conversation you kept putting off, the trip you said you’d book “soon”, they pile up quietly until they become regrets.

This isn’t about catastrophizing. It’s about a simple truth: the most certain time you have is now.

A Better Framework: The Five-Year Window

Instead of the anxiety-inducing “last day” mindset, try this: imagine you have five more years, and picture everything you want to have done, seen, and felt within that window.

Five years is long enough to be realistic. It’s not a countdown to disaster; it’s a planning horizon that forces clarity. When you think in five-year terms, the travel you keep postponing stops being a vague “someday” dream and starts being a decision. The time you want to spend with family and friends becomes a priority you can actually schedule. The work you keep pushing gets assessed honestly. Is it worth your time, or has it been weighing on you for reasons you’ve been avoiding?

That timeline helps you see life in a much sharper sense. The five-year lens also turns abstract desires into real questions you have to answer.

If you’ve been thinking about quitting your job, would you still be there in five years, or would you have finally made the move? If you want to go skydiving, what exactly are you waiting for? If there’s something you’ve wanted to say to someone, what are the chances the moment will be more convenient later?

These aren’t questions designed to create pressure. They’re questions designed to create honesty.

What I’m Reading

Raising Brows - Anastasia Soare (Finished)

The story of how Anastasia Soare arrived in the U.S. without speaking English and built a billion-dollar global beauty empire by mastering a single, overlooked detail. This is a book of inspiration.

Mattering- Jennifer Breheny Wallace (Currently Reading)

Mattering examines how the need to feel significant shapes our ambition, relationships, and identity, and why true confidence comes from knowing we matter beyond achievement.

What Else Dropped This Week

Off Script

Why Deepa Walked Away From Corporate to Build Her Own Brands

Under the Hood

The Sephora Paradox: One Brand Sold for Millions. The Other Just Shut Down. Both Were in 600 Stores.

Skin Deep

The Beginner’s Guide to Moisturizing: Everything You Need to Know to Start Your Skincare Journey

On My Reading Desk

1. They were about to shut down their business. Then a raw TikTok changed everything.

2. Update is Skims, you can drink

3. Reese Witherspoon Has Some Surprising Career Advice: Stop Chasing Your Dreams — And Do This Instead

4. Science Says Rich People Aren’t Inherently Smarter. Mark Cuban Agrees

Note to My Future Self

Enjoy what you can today. Do the things you’re capable of doing now. Say the things you mean to say. Take the steps you’ve been circling.

Not because the world is ending. Not because you should live in a state of urgency or fear. But because the present is the only moment where action is actually possible. The future is where we store our intentions. Today is where we act on them.

Be bold. Be real. Be Anomalous.

— Sai Menon

If you’ve ever stood in the skincare aisle feeling completely lost, this one’s for you.

Let’s be real, skincare can feel overwhelming. There are serums, essences, toners, oils, creams, and gels, each one promising to transform your skin in 30 days or less. It’s a lot.

But here’s what I want you to know before you spend a single dollar on any of it: the most important thing you can do for your skin isn’t a $100 serum or a 10-step routine. It’s something far simpler.

It’s moisturizing.

Done consistently, every single day, a good moisturizer is the foundation on which everything else is built. And once you understand why, it starts to make sense.

First, Let’s Talk About Your Skin Barrier

Your skin isn’t just the surface you see in the mirror. It’s a living organ, and its outermost layer, called the skin barrier, does two critical jobs: it keeps moisture in and irritants out.

Think of it like a brick wall. The skin cells are the bricks, and the lipids and fats between them are the mortar holding everything together. When that wall is intact and healthy, your skin stays hydrated, resilient, and calm.

But when the barrier gets damaged through harsh cleansers, cold weather, over-exfoliating, or just the natural aging process, water starts to escape faster than it should. Dermatologists call this transepidermal water loss, and it’s the root cause of dry, flaky, tight, or dull-looking skin.

Moisturizing is how you repair and reinforce that wall. It’s not a cosmetic step. It’s maintenance.

What Does a Moisturizer Actually Do?

Not all moisturizers work the same way. The best ones contain a combination of three types of ingredients, each doing a different job:

Humectants are the water magnets. They draw moisture from the air and from deeper layers of your skin up to the surface. Hyaluronic acid and glycerin are the most common examples you’ll see them in almost every moisturizer worth buying.

Emollients are the smoothers. They fill in the tiny gaps between skin cells, giving skin that soft, silky texture. Think squalane, ceramides, jojoba oil, and shea butter.

Occlusives are the sealers. They sit on top of the skin and create a physical barrier to stop moisture from evaporating. Petroleum jelly is the most effective occlusive there is, humble, cheap, and extremely effective.

A good moisturizer will ideally combine all three. That’s how you get skin that’s not just temporarily plump, but genuinely healthy over time.

Which Moisturizer Is Right for You?

The wrong moisturizer, even a good one, won’t work well for you if it doesn’t suit your skin type.

Here’s a quick breakdown:

Dry skin tends to feel tight, rough, or flaky after cleansing. You need a richer, creamier formula that delivers both hydration and a strong occlusive seal. Look for ceramides, shea butter, and squalane. Avoid anything with a high alcohol content, which will only make dryness worse.

Examples: Embryolisse Lait Creme, Cocokind Resurrection Polypeptide Cream,

Oily skin can feel greasy by midday and is often prone to breakouts. Here’s the thing, though: oily skin still needs moisture. When oily skin is stripped through harsh cleansers, it often compensates by producing more oil. The key is finding a lightweight, water-based gel or fluid that hydrates without clogging pores. Look for the word non-comedogenic on the label, and reach for ingredients like niacinamide and hyaluronic acid.

Examples: Netrogena HydroBoost, Cocokind Electrolyte Water Cream

Combination skin is exactly what it sounds like: oilier in the T-zone (forehead, nose, chin) and drier on the cheeks. A medium-weight moisturizer often does the job, or some people prefer using two different products on different areas of the face.

Examples: CeraVe PM Facial Moisturizing Lotion, Belif Aqua Bomb

Sensitive skin reacts easily to products, weather, stress, you name it. Keep it simple. Look for fragrance-free, minimal-ingredient formulas with calming ingredients like ceramides, oat extract, or centella asiatica. Fragrance, even “natural” fragrance from essential oils, is one of the most common causes of skin irritation, so avoiding it is a good rule of thumb when you’re starting.

Examples: Avène Tolerance Control Cream, Embryolisse Lait Crème Sensitive Moisturizer

When Should You Moisturize?

Twice a day: morning and evening. Every day. That’s the short answer.

The slightly longer answer: the best time to apply moisturizer is right after cleansing, while your skin is still slightly damp. Damp skin absorbs ingredients more effectively, and the moisture that’s already there gets locked in rather than evaporating. Pat your skin dry (don’t rub), and apply your moisturizer within about 60 seconds of cleansing.

In the morning, a lighter moisturizer works best because it layers well under sunscreen, and yes, sunscreen is non-negotiable, even in winter, even when it’s overcast. It goes on after your moisturizer, as the last step before makeup.

In the evening, your skin is in repair mode. Cell turnover speeds up overnight, and your skin is more receptive to nourishing ingredients. This is the time to use a richer formula. If your skin is very dry, you can even try slugging, applying a thin layer of petroleum jelly as the very last step to seal everything in while you sleep. It sounds strange, but it works.

The Bottom Line

Healthy skin isn’t about having the most elaborate routine or the most expensive products. It’s about consistency, understanding what your skin actually needs, and giving it that every day.

Moisturizing is where most beginners see the fastest, most noticeable improvement: less tightness, smoother texture, fewer dry patches, and over time, a more even and resilient complexion.

Start simple. Stay consistent. And trust the process your skin barrier will thank you for it.

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Briogeo and Ami Colé both made it to Sephora’s shelves. Both were Black-founded. Both were beloved. What happened next could not have been more different, and every entrepreneur building a consumer brand needs to understand why.

Getting into Sephora is supposed to be the moment. It’s the validation that your brand is real. It’s the distribution that opens you up to millions of new customers. It’s the press pitch that writes itself. “Now available at Sephora.”

Two brands — Briogeo and Ami Colé got that moment. Both were clean beauty brands. Both were Black-founded. Both built genuine communities of devoted customers. Sephora believed in both of them enough to put them on the shelf.

Briogeo was acquired by Wella in 2022 in a deal that made Nancy Twine one of the most celebrated exits in indie beauty. Ami Colé announced it was shutting down in July 2025, with its founder writing in an essay for The Cut that she couldn’t compete with brands that had deeper pockets and that “prime shelf space comes at a price” she could no longer afford.

Same retailer. Same category. Same cultural moment. Completely different outcomes.

The question worth sitting with: why?

Briogeo: The Goldman Sachs VP Who Made Hair Care Her Life’s Work

Nancy Twine didn’t set out to build a beauty company. She set out to build a life with more meaning in it.

She’d been at Goldman Sachs for nearly a decade, working her way to VP. She was successful, but she was unfulfilled. Then her mother died suddenly, and the loss opened something up. Twine kept returning to memories of her childhood kitchen, where her mother, a physician, would concoct homemade hair and skin treatments from natural oils, butters, and extracts picked up from health food stores.

She started doing what most people do when they’re considering a pivot but still paying rent: she researched obsessively at night. She wrote a business plan on weekends. She contacted manufacturers, talked to chemists, ordered samples, and sent boxes to friends. For a year, she did this while still drawing a Goldman salary.

What she saw in the market was a gap between natural and performance. Most clean hair care felt earnest but ineffective. Most high-performance hair care was full of silicones, sulfates, and parabens that Twine didn’t want on her hair. She wanted both, and she believed other women did too.

She built Briogeo around a simple framework she called “6-free”: no sulfates, silicones, parabens, phthalates, DEA, or artificial dyes. Products that were 93 to 100 percent naturally derived, but that actually worked. The name combined brio, an Italian word for vibrancy, with geo, a nod to the earth. She developed four products. She packed them in sample boxes in her tiny East Village studio apartment.

In 2013, she took those samples to a beauty trade show in Las Vegas. Six months later, she got an email from Sephora. They wanted to carry her line.

Two weeks later, she quit Goldman Sachs.

The Sephora Relationship That Changed Everything

Twine has been direct about what Sephora meant to her: “I’m forever indebted to Sephora because they took a bet on me before anyone else really did. Because of that, we were able to really grow our brand and bring in so many incredible customers from around the world.”

But Twine didn’t just take Sephora’s bet and coast. She understood what it actually required of her to land on that shelf.

She had spent nearly a decade watching Goldman’s clients, some of the most sophisticated businesses in the world, manage financial complexity, capital allocation, and operational risk. She brought those instincts to Briogeo. She didn’t hire fast. She didn’t raise VC money. For six years, Briogeo never took any outside VC or PE investment. Twine funded the business by dipping into her personal savings until the brand became profitable.

She treated Sephora not as a finish line but as a growth channel with its own demands, and she learned those demands intimately. She sampled aggressively because she understood that in prestige retail, trial converts skeptics. She developed hero products that could anchor the line and become reliable repeat purchases. Her Deep Conditioning Mask became one of the most awarded products in Sephora’s hair category, winning the Allure Best of Beauty Award every year from 2018 onward.

She also understood what Sephora couldn’t do for her. It could put her product in front of millions of customers. It couldn’t build her brand. That was her job. She used digital, editorial, and community to pull customers into the brand so that when they walked into Sephora, they were already looking for Briogeo, not just stumbling across it.

The business grew steadily. By 2020, Briogeo had an estimated gross revenue of $40 million. It was one of the top-selling hair care brands on Sephora.com. It had expanded to Nordstrom, Urban Outfitters, and international markets. And then, in 2022, nine years after launching, Briogeo was acquired by Wella Company. At 29, Twine had become the youngest Black woman to launch a product line at Sephora. By her early thirties, she had built and sold one of the most successful indie hair care companies in the country.

Ami Colé: The Right Brand at the Wrong Time

Diarrha N’Diaye-Mbaye’s story starts in a Harlem hair salon. Her mother, Aminata — Ami, for short, ran a salon that was the social and cultural heart of their Senegalese community in New York. Growing up inside it, N’Diaye-Mbaye absorbed something that would shape everything she built: the idea that beauty isn’t just a product, it’s community, culture, identity, and belonging.

She spent a decade working in the beauty industry, at Temptu, L’Oréal, and Glossier, before she tried to build something of her own. She had the idea for years, but the doors kept closing. Investors told her Fenty Beauty already existed, implying the market for Black beauty was somehow complete. She couldn’t get traction.

Then George Floyd was murdered in May 2020. Corporate America responded with a wave of pledges, capital commitments, and public declarations about equity. The Fifteen Percent Pledge launched, pressuring retailers to dedicate shelf space to Black-owned brands. Sephora signed. Investors became, in N’Diaye-Mbaye’s words, “a little bit more sensitive and sensitized to where they sit on the spectrum of equity.”

Within weeks of the uprisings, she received an influx of requests to bring her “deserving brand” to life. She raised over $1 million in pre-seed funding and launched Ami Colé in May 2021 with three products: a skin tint, a lip oil, and a highlighter, all formulated specifically for melanin-rich skin.

The brand was an immediate cultural hit. Within months of launching, Ami Colé sold out its first run of products, created a viral lip oil that became a staple in makeup bags from Harlem to Accra, and became a favorite among celebrities like Kelly Rowland, Mindy Kaling, and Martha Stewart. It went on to win more than 80 product awards and earned a spot on Oprah’s Favorite Things list.

In December 2022, Ami Colé launched in 277 U.S. Sephora doors, a full-circle moment for N’Diaye-Mbaye, who had worked as a Sephora sales associate during her undergraduate years at Syracuse. By 2024, the brand had expanded to 600 Sephora locations across North America. L’Oréal’s BOLD venture fund made a minority investment.

By every visible measure, Ami Colé had made it.

The Hidden Cost of the Shelf

Here is what the press releases don’t tell you about getting into Sephora at scale: the shelf is not the reward. The shelf is where the real battle begins.

Sephora is not a charity. It is a retailer with aggressive sell-through targets. If a brand doesn’t move product at the pace Sephora needs, it gets moved or removed. To move product at that pace, a brand needs marketing. Not the organic kind, the paid kind. Premium shelf placement, the eye-level spots, and the front-of-store displays are literally purchased. When you walk into Sephora and see stacks of Sol de Janeiro body mists off the bat, that’s their $200 million marketing budget at work.

N’Diaye-Mbaye wrote about this directly in her essay for The Cut: “I couldn’t compete with the deep pockets of corporate brands; at retail stores, prime shelf space comes at a price, and we couldn’t afford it.”

Ami Colé’s roughly $3 million in total funding is a lot for a layperson, but a drop in the bucket for achieving success at Sephora. The cost of the inventory alone, scaled to 600 stores, with the kind of shade range an inclusive makeup brand is expected to carry, is enormous. Add the marketing spend needed to drive traffic to those stores, the PR, the influencer seeding, and the operational infrastructure to manage it all, and you’re looking at a capital requirement that most indie brands simply cannot meet.

N’Diaye-Mbaye also described how her attempts to grow hurt her: “We made operational decisions that felt necessary at the time, like scaling up production to meet potential demand, without truly knowing how the market would respond.” Stock levels became difficult to predict, as viral peaks caused products to sell out and then be overstocked.

This is the Sephora paradox for undercapitalized brands: you need scale to afford the shelf, and you need the shelf to get the scale. The math only works if you have enough capital to absorb the gap between the two. Ami Colé didn’t.

The Funding Cliff That Nobody Warned About

There’s a harder dimension to Ami Colé’s story that N’Diaye-Mbaye addressed with unusual candor.

In 2020, investors were talking a big game about equity and representation by pledging dollars, launching initiatives, and building buzz. Some of that capital was genuine. Some of it was performative “diversity investing” that was more about optics than the long-haul commitment that consumer brands require.

N’Diaye-Mbaye wrote that investor expectations had become “temperamental,” that some of the investors who had talked about “betting big on inclusivity” in 2020 changed their tune as years passed. The landscape changed considerably, with funding drying up for Black-owned brands and broader DEI rollbacks under the current political administration hindering institutional support.

Ami Colé raised $3 million total. Briogeo bootstrapped for six years before taking any outside capital and only did so after the business was profitable. The sequence matters. Briogeo earned its way to scale. Ami Colé was asked to grow before the business was fully ready, and then the capital environment that had encouraged that growth evaporated.

This isn’t a story about one brand failing and another succeeding. It’s a story about the conditions different founders inherited and how much those conditions shaped the options available to them.

What Every Founder Building for Retail Needs to Hear

Sephora is not the goal. Sephora is a channel. And like every channel, it has its own economics, its own margin requirements, its own marketing costs, its own expectations for velocity and growth. Going in underprepared or undercapitalized doesn’t just slow you down. In prestige retail, it can end you.

The question isn’t whether to pursue retail. It’s when, at what scale, with how much capital in reserve. Briogeo went in at the right time, with the right product, and enough personal commitment to survive the early years before the business could support itself. Ami Colé went in at a pace the business and its capital structure couldn’t sustain.

None of this is a criticism of Diarrha N’Diaye-Mbaye. She was handed a structural challenge, the expectation of rapid scale with insufficient long-term capital, that would have broken most founders. She turned $1 million into a brand that sold out its launch, went viral, won 80 awards, landed on Oprah’s list, and reached every Sephora in North America.

In her own words: “Don’t be afraid to fail out loud.”

The harder truth is systemic: the capital that rushed toward Black-owned brands in 2020 came with the same growth expectations as any other VC bet, without the same depth of patient support. And in a category as capital-intensive as prestige makeup, that mismatch was always going to be dangerous.

Both founders built something real. One had the runway to let it compound. The other was asked to run before she could walk, and when the runway ran out, there was no one to extend it.

The Lesson

If you’re building a consumer brand and thinking about retail, understand the true cost of the shelf before you say yes to it. Not just the margin economics. The marketing spend. The inventory commitment. The operational infrastructure. The capital you’ll need to compete for attention against brands with budgets that dwarf your entire raise.

Briogeo took nine years to get to an exit. Nine years of building, iterating, and earning its way to scale. That’s not a cautionary tale. That’s the whole point.

If this was useful, share it with a founder who’s about to sign a retail partnership without running the real numbers first.

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