In 2013, Michael Moritz of Sequoia Capital put $8 million into a year-old grocery delivery startup called Instacart and took a seat on its board.

If you knew Moritz’s history, this was a strange bet. Sequoia had been one of the backers of Webvan, the online grocer that raised hundreds of millions, went public in 1999, and was gone by the summer of 2001. When Bloomberg asked him about the new investment, Moritz joked that his firm had still been in “outpatient therapy for our Webvan fiasco.”

Same investor and Same idea: groceries, ordered online, brought to your door. Twelve years apart.

One became the most expensive cautionary tale of the dot-com era. The other went public in 2023 at a $9.9 billion valuation.

The usual explanation is that Instacart executed better. That’s true, but it skips the more interesting question:

Why now?

Under the Hood is where we take apart the companies and founders behind the headlines the decisions, the numbers, and the years nobody saw. If you’re building through the hard middle, subscribe. This one’s for you.

The Lens: Paul Orlando’s Two Questions

Paul Orlando has built and run four startup accelerators around the world. He teaches entrepreneurship at USC and directs its startup incubator. After watching thousands of teams, he kept seeing the same thing: some founders worked brutally hard and still failed, while others seemed to work a little less and won anyway. Often, the difference was timing. He wrote the book on it: Why Now: How Good Timing Makes Great Products.

"Somebody came along later doing pretty much the same thing. And it wasn't that the management style was radically different. It was: the business model didn't support it back when we were doing it, and it does support businesses doing it now." — Paul Orlando, on Be Anomalous

His framework boils down to two questions. We’ll run both companies in each pair through them.

Question 1: What has changed in the world that makes this possible now? Paul tracks twelve forces he calls timing drivers: technology, social and behavioral shifts, regulation, installed base (existing products you can ride on), economics, networks, distribution, access to capital, organizational models, available talent, demographics, and crisis. No single driver makes a company. Winners usually sit where several converge.

Question 2: Do those changes actually fix the business model? This is the part most founders skip. A trend only matters if it changes your unit economics, what it costs to acquire, serve, and keep a customer. A real need served at a loss is still a loss, no matter how good the timing looks.

Case Study 1: Webvan vs. Instacart

The idea

Order groceries online. Get them delivered to your door. Identical promise, twelve years apart.

Why Webvan failed

Webvan was founded in 1996 by Louis Borders, who had co-founded Borders Books. It had blue-chip investors, and the customers who used it genuinely loved it. It did not fail because people didn’t want it.

It failed because it had to build the entire system itself, before demand existed to pay for it.

Webvan started taking orders in the Bay Area in June 1999. Five weeks later, with roughly 10,000 customers, it placed a $1 billion order with Bechtel to build automated warehouses in 26 markets. Each hub cost around $30 million. Borders said he wanted Webvan in every metro area big enough to have a major league sports team. That November, it raised $375 million in its IPO. It bought a fleet of trucks. It bought its money-losing rival HomeGrocer for $1.2 billion in stock.

Every warehouse, every truck, every driver was a fixed cost Webvan carried before it knew whether customers would come in enough volume. They didn’t. In July 2001, Webvan filed for bankruptcy, laid off 2,000 people, and left more than $800 million in losses behind.

Why Instacart won

Apoorva Mehta launched Instacart in mid-2012 and went through Y Combinator that summer. He wasn’t a first-timer: by his own account he’d tried around twenty companies that didn’t work, and before that he’d been a supply chain engineer at Amazon working on fulfillment. He knew exactly what had killed Webvan, and he designed the opposite.

Instead of building warehouses, Instacart treated existing supermarkets- Safeway, Whole Foods, Trader Joe’s, Costco as its warehouses. Instead of buying trucks, it dispatched independent shoppers in their own cars. Its core asset wasn’t concrete; it was software that batched orders, mapped store aisles, and routed shoppers.

The result: Instacart could open in a new city without building anything. No warehouse, no fleet, no inventory risk.

Then the crisis driver hit. When the pandemic arrived in 2020, grocery delivery became a necessity overnight. Instacart brought on 300,000 new shoppers in the weeks after March 2020, and by October its private valuation had reached roughly $17.7 billion. In September 2023, it went public at a $9.9 billion valuation, raising $660 million.

The timing scorecard: 1999 vs. 2012

Installed base

• 1999: Nothing to ride on. Webvan had to build its own warehouses and buy its own trucks.

• 2012: The iPhone was five years old. Customers ordered from their pockets, shoppers were routed through theirs, and thousands of stocked supermarkets served as ready-made warehouses.

Organizational model

• 1999: Delivery meant hiring and managing a full workforce.

• 2012: On-demand contractor work had become a recognizable model.

Available talent and economics

• 1999: A tight boom-era labor market.

• 2012: The Great Recession had left a large, flexible labor pool looking for hours.

Social and behavioral

• 1999: Online shopping was still a novelty for most households.

• 2012: A decade of e-commerce had made buying from someone you’d never meet feel normal.

Capital access

• 1999: Bubble-era money let Webvan commit a billion dollars before proving its model.

• 2012: Post-crash investors, including the ones who’d lost money on Webvan, wanted capital efficiency.

Crisis

• 2001: The dot-com crash cut off the funding Webvan depended on.

• 2020: The pandemic turned Instacart from a convenience into infrastructure.

The verdict

Run it through Paul’s two questions. Question 1: almost every driver Webvan lacked was present for Instacart. Question 2: those drivers didn’t just make delivery possible; they collapsed the cost of entering a market from hundreds of millions of dollars to almost nothing.

Webvan wasn’t wrong about the future. It was wrong about when the future would be cheap enough to afford.

Case Study 2: Pets.com vs. Chewy

The idea

Sell pet food and supplies online. Ship them to the door. Identical promise, thirteen years apart.

Why Pets.com failed

Pets.com launched in November 1998. Amazon took a major stake in its first funding round. Its sock puppet mascot became a genuine celebrity, with a balloon in the 1999 Macy’s Thanksgiving Day Parade and a national Super Bowl ad in January 2000. That February, Pets.com went public and raised $82.5 million.

Two hundred and sixty-eight days later, it was shutting down.

The demand was real: pet owners wanted someone else to haul the dog food. The problem was what it cost to haul it. Pets.com was shipping heavy, bulky, low-margin goods like fifty-pound bags of kibble, often below cost, with free shipping to win customers. Every order dug the hole deeper. In the first nine months of 2000, it lost $147 million. By November it had closed, and about 300 people were out of work.

This is Paul’s clearest example of failing Question 2. The value proposition was sound. The cost structure was impossible. And no amount of brand awareness fixes an order that loses money every time it ships.

Why Chewy won

Ryan Cohen was 25 when he started Chewy in 2011 with Michael Day. It wasn’t their first idea. The pair had put $150,000 of their own money into an online jewelry business, realized at a trade show they had no passion for it, sold the inventory for 80 cents on the dollar, and started buying pet supplies from distributors with what was left.

Chewy faced the exact question that killed Pets.com: how do you profitably ship a fifty-pound bag of dog food?

Its answer was Autoship. Pets don’t stop eating, so pet food is one of the most predictable purchases a household makes. Chewy built around that: customers sign up once, and the food arrives on schedule. That one design choice rewires the unit economics:

• Acquisition: You win the customer once instead of paying to win them back every month.

• Inventory: Recurring orders make demand forecastable, so stock runs leaner.

• Fulfillment: Shipments can be planned rather than improvised.

• Retention: Round-the-clock customer service that treated pet owners like family built the loyalty Pets.com tried to buy with Super Bowl ads.

It worked. Chewy hit nearly $900 million in revenue within five years. In 2017, PetSmart bought it for $3.35 billion, the largest e-commerce acquisition at the time. In 2019, it went public at roughly $8.7 billion. In its most recent fiscal year, Chewy reported $12.6 billion in net sales across 21.3 million active customers, with $10.5 billion of that coming from Autoship customers, roughly five of every six dollars.

The timing scorecard: 2000 vs. 2011

Social and behavioral

• 2000: Buying online was new and untrusted for most people.

• 2011: Online shopping was routine, and Amazon Prime had spent years teaching customers to expect a box on the doorstep.

Distribution

• 2000: Shipping heavy goods nationally was slow and expensive.

• 2011: National parcel networks were faster, denser, and more efficient.

Technology

• 2000: E-commerce infrastructure was expensive and had to be built at bubble-era prices.

• 2011: That infrastructure was cheap and standard.

Capital access

• 2000: Easy money funded growth and advertising without a path to profit, then disappeared overnight.

• 2011: Post-crash investors demanded a business that could stand on its own math.

Business model

• 2000: One-off orders, free shipping, prices below cost.

• 2011: Recurring orders that made every customer more valuable over time.

The verdict

On Question 1, Chewy had real tailwinds Pets.com never had. But this case is mostly about Question 2. The drivers made online pet supplies easier by 2011; they didn’t automatically make it profitable. Chewy still had to design a model: Autoship, which turned the heavy, boring repeat purchase that killed Pets.com into its greatest asset.

What Actually Compounds

The comforting reading of these four companies is that timing is luck. Paul’s work says the opposite: timing can be studied, tested, and designed for.

An idea that “already failed” might just have been early. Grocery delivery wasn’t a bad idea in 1999. Online pet supplies weren’t a bad idea in 2000. They were good ideas waiting for the world to catch up, and for the right founders, shaped by years nobody saw, to be ready when it did.

Be Bold. Be Real. Be Anomalous.

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Natalia Flores didn’t set out to start a business.

She grew up in Mérida, in the south of Mexico, studied in Monterrey, and came to Berkeley on a six-month exchange program. Six months became a year. A year became an internship, then a job, and eight years later she still calls San Francisco home.

Then COVID hit. Stuck at home and cooking constantly, she missed the spicy flavors she grew up with, and she couldn’t find them here. So she started making them herself: salsas cooked in the same pan she used for dinner, peppers chopped with her own kitchen knives, jars ordered from Amazon, and labels designed in Canva and printed at home.

She sold 20 to 40 jars a month to friends, just for fun. Then someone she’d never met, a friend of a friend, reached out to buy one.

That message changed how she saw it.

A chance conversation with the founder of a major salsa company pointed her to La Cocina, San Francisco’s nonprofit incubator for food businesses. She applied with six different salsas. By the time she launched, she’d narrowed it down to one: a crunchy chili crisp made from just three ingredients.

Today, Flor de Chile is made by a team of four in a commercial kitchen in the Mission, and her best friend is now her business partner. They can make 400 jars in six hours, all by hand, and the brand is stocked in stores across San Francisco.

Along the way, she’s learned that you never have it all figured out before you begin. You start, and you figure it out as you go.

This conversation goes far beyond food. We talk about:

• The moment a hobby starts becoming a real business

• Why one order from a stranger meant more than a hundred from friends

• How La Cocina helped her formalize the business, and why she launched one product instead of six

• How to think about leaving your job, and why her transition was gradual

• Running a business while working full time, then part time

• What happens when your best friend becomes your business partner

• Going from a home kitchen to a commercial kitchen, one problem at a time

• Managing inventory, forecasts, and shelf life in a food business

• Bootstrapping on $10,000, and why every dollar of revenue gets reinvested

• When outside capital becomes necessary to scale

• Building a team when you’ve always done everything yourself

• Creating a brand rooted in culture without leaning on clichés

• Why she isn’t worried about anyone copying her recipe

• Why getting on the shelf is the easy part, and getting off it is the hard part

• Her advice for anyone whose fear is holding them back

Natalia’s story is a reminder that you don’t need a plan to start.

Sometimes a craving becomes a recipe. A recipe becomes a business.

And a business becomes a way to share home with the rest of the world.

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A Line From the Conversation

"Don't wait for it to be perfect... just try it out, and you'll figure out the rest along the way."

Favorite Book

Shoe Dog by Phil Knight

Natalia’s pick is a fitting one for this conversation. Phil Knight’s memoir of building Nike shows how messy the early years of a company really are: the cash crunches, the near-misses, and the decisions made without all the answers. It’s the same truth running through Natalia’s story. Behind every brand you see on a shelf is a founder who kept going without having it all figured out.

Favorite Quote

"Shoot for the moon. Even if you miss, you'll land among the stars."

(00:00) Intro: Natalia’s journey from Mérida to San Francisco
(01:37) Growing up in Mérida, Mexico
(02:37) How a six-month exchange became eight years
(04:07) A COVID hobby begins
(05:26) The order from a stranger that changed everything
(06:58) Selling 20 to 40 jars a month from her kitchen
(09:05) Discovering La Cocina
(10:21) From six salsas to one product
(12:03) Running a business while working full time
(13:11) How to know when to quit your job
(15:28) The support system behind the business
(17:50) When your best friend becomes your business partner
(19:43) Protecting the friendship
(22:08) From home kitchen to commercial kitchen
(25:30) From 200 jars a month to 400 in six hours
(26:57) Why they still make every jar by hand
(27:56) Inventory, forecasting & shelf life
(30:34) Bootstrapping vs. raising capital
(32:25) What it actually costs to start
(33:45) Building a team
(37:05) A brand rooted in culture
(41:07) The story behind the name
(42:59) Is she worried about copycats?
(45:16) The biggest challenge: getting it off the shelf
(48:51) What’s next for Flor de Chile
(51:09) What she’s learned as a leader
(54:12) Advice if fear is holding you back
(55:24) Favorite quote & book

Most of us have an idea we keep coming back to. Few of us act on it, because we’re waiting until we have it all figured out.

Natalia didn’t wait. She started with what she had, solved one problem at a time, and let the business grow as she did.

If you’ve been sitting on an idea, waiting for the right moment, this conversation is for you.

Subscribe to Be Anomalous for honest conversations with founders, creators, and cultural disruptors who are building outside the lines.

New episodes drop every Tuesday.

Be Bold. Be Real. Be Anomalous.

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

Picture the post. A product drops at 9 a.m. By noon, it’s sold out. The founder shares a screenshot of the Shopify dashboard, the comments fill with fire emojis, and somewhere a reader in the hard middle of building their own thing feels: why isn’t that me?

Here’s what the screenshot doesn’t show. It doesn’t show how much was spent on ads to get those buyers. It doesn’t show whether the inventory run was 50,000 units or 500. And it can’t show the only thing that actually matters yet: whether any of those customers will come back.

This week, Under the Hood isn’t about one founder. It’s about the instrument panel every founder eventually has to learn to read. Because once you can see what’s underneath the buzz, you stop comparing your quiet progress to someone else’s loud launch. You start measuring what compounds.

Under the Hood is a weekly breakdown of how real businesses are built, for people still in the invisible years of building their own. Subscribe so the next one lands in your inbox.

The Only Question That Matters Early

A business works when it can turn demand into repeatable, profitable growth. Not a viral month or create a timely buzz.

For a consumer brand, that boils down to one question: do people buy once because the marketing worked, or buy again because the product works?

Revenue can’t answer that. A brand can buy millions in sales with ads, discounts, influencers, and a splashy retail launch. If none of those customers return, that isn’t a business. It’s expensive distribution. That’s why, for most early brands, retention is the more honest number. Five companies show what that looks like from different angles.

Poppi: Attach Yourself to a Habit

Poppi didn’t invent a new behavior. It walked straight into one of America's most frequent purchases, a can of soda, and offered a version people felt better about drinking.

That choice is the whole business. A product people reach for daily gives you dozens of chances a year to earn a repeat. The viral TikToks and the celebrity fans only mattered because the next can got bought too. When PepsiCo closed its acquisition in May 2025 for $1.95 billion, it wasn’t paying for a moment. It was paying for a habit that had already proven itself on shelves.

The lesson: the strongest consumer brands rarely create demand from nothing. They find a habit people already have and make it more desirable.

What to watch: repeat rate by cohort, units per customer per month, retail velocity (units sold per store per week), margin after retailer fees and promotions.

Rhode: Attention Is Not the Business

Hailey Bieber can make millions of people look at a lip treatment. That’s real leverage: it makes customers cheaper to acquire. But attention only gets you the first order. The question every celebrity brand eventually faces is whether the product keeps selling once the novelty wears off.

Rhode’s answer showed up in two places. First, on the shelf: e.l.f. called its Sephora North America debut record-breaking. Second, in the numbers after the hype. On e.l.f.’s Q4 fiscal 2026 call (fiscal year April 2025 to March 2026), the company said Rhode did roughly $390 million in net sales, up more than 80%, and over $500 million in global retail sales on an annualized basis.

Notice those are two different numbers. Retail sales is what shoppers paid at the register. Net sales is what the brand actually received after retailers took their cut. Learning to ask which one you’re looking at is half of reading any headline.

The lesson: celebrity lowers the cost of the first sale. Product quality and replenishment decide every sale after that.

What to watch: hero-product sell-through, time between repurchases, sales per store per week, share of revenue from returning shoppers.

Thrive Causemetics: The Money Is in the Second Order

Karissa Bodnar built Thrive around hero products that solve a specific problem, sold mostly direct to the customer. When you sell direct, you own the relationship: the email address, the purchase history, the chance to suggest what comes next.

That changes how you think about the first sale. A mascara bought through an ad might barely break even. Its real job is to start a relationship. The profit lives in the second order, the third, and the brow gel and eyeliner that join the routine later.

The lesson: one hero product can be your acquisition engine. The economics are decided by what happens after the first purchase.

What to watch: first-to-second-order conversion, days until the second order, order size from bundles and cross-sells, share of revenue from email and SMS, how many months it takes to earn back what you spent acquiring a customer (CAC payback).

Costco: The Renewal Is the Product

Most people think Costco sells groceries. But it sells a yearly decision: is this membership still worth it?

The flywheel runs like this. Membership fees help fund rock-bottom prices. Low prices pull members in more often. More traffic gives Costco leverage with suppliers, which keeps prices low, which makes renewing an easy call. The visible metric is sales. The one that proves the model is renewal.

In its fiscal Q4 2026 results (the quarter ending August 30, 2026), Costco reported a 92.3% renewal rate in the US and Canada and 89.8% worldwide, across 150.4 million cardholders. Analysts watch that number closely, and even a slip of a few tenths of a point makes headlines. That metric is their real business.

The lesson: find the number that proves customers are choosing to stay, not the one that just reports activity.

What to watch: renewal rate, comparable-store sales, sales per member, membership-fee income, inventory turns.

Netflix: Watch What a Company Stops Telling You

For a subscription business, the real question isn’t how many people signed up. It’s whether they keep finding enough value to stay. Someone who watches every week rarely cancels. Lower churn makes every dollar spent on content and marketing work harder. Engagement is the leading indicator; retention is the payoff.

Netflix made this point. Beginning in 2025, it stopped reporting quarterly subscriber numbers, calling engagement its best proxy for customer satisfaction. Then in July 2026, it said it would publish engagement reports only once a year starting in 2027, focusing on revenue and operating profit instead.

Companies highlight the metrics that provide value to them and quietly retire the ones that don’t. When a number disappears, ask why. Mature businesses often shift to profit metrics as growth slows, and that shift can be healthy.

The lesson: in subscriptions, engagement predicts retention. And for any company, what it chooses to disclose is data too.

What to watch: churn, time spent per user, ad-tier adoption, revenue per member, engagement per dollar of content spend.

The Cheat Sheet: Vanity vs. Business Metrics

Next time a brand’s success crosses your feed, swap the number on the left for the question on the right.

“Sold out” deserves a special note. It can mean overwhelming demand. It can also mean a cautious production run. The proof is whether the product keeps selling after the restock, at a healthy margin.

What Actually Compounds

The five questions explain every business in this piece. Use them on any company you’re studying, including your own:

1. What job does the product do? What habit, frustration, or desire is it replacing?

2. What proves customers care? Repeat orders, renewals, sell-through, people searching for you by name.

3. What makes growth affordable? Margin, order size, lifetime value, and how fast you earn back acquisition costs.

4. What makes it repeatable? A channel you can keep pouring into: direct, Amazon, retail, wholesale, subscription.

5. What could break it? Rising ad costs, weak repeat, discount dependence, one retailer holding too much power, or a business that only works while the founder is posting.

None of these answers show up in a launch-day screenshot. They show up months later, in the quiet data. Which is exactly why the early, unglamorous stretch counts so much: it’s when repeat customers and real margins are actually built.

Your Move

If your launch didn’t sell out, you’re not behind. If you have fifty customers and twenty of them came back, you may have something many viral brands never find: proof the product works.

Revenue tells you people bought it. Retention tells you they actually want it. Margin tells you whether the business deserves to survive.

Be Bold. Be Real. Be Anomalous.

Sources

• PepsiCo: completion of Poppi acquisition (May 2025)

• e.l.f. Beauty Q4 FY2026 earnings call

• WWD: e.l.f. fiscal 2026 forecast and Rhode Sephora launch

• Costco Q4 FY2026 supplemental information (SEC)

• Variety: Netflix to stop reporting subscriber numbers

• Morningstar: Netflix moves engagement reports to annual

• BCG: the LTV: CAC ratio

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

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

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

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

The experience changed the way Paul thought about entrepreneurship.

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

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

This conversation goes far beyond startups. We talk about:

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

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

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

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

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

• How AI is changing what a solo founder can build

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

• Whether Paul would ever become a founder again

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

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

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

🎧 Listen to the episode

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A Line From the Conversation

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

Favorite Book

Erewhon by Samuel Butler

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

In This Episode

In this conversation:

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

The world is changing faster than ever.

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

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

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

Subscribe to Be Anomalous for honest conversations with founders, creators, and cultural disruptors who are building outside the lines.

New episodes drop every Tuesday.

Be Bold. Be Real. Be Anomalous.

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

This week I started thinking about death.

Not in a morbid way. In a life-and-death way.

Hear me out.

We all live with what I am calling a boxed time mindset. Each phase of life comes with its own set of worries, its own checklist, its own version of what we are supposed to be focused on.

In your 20s, it is career and finding the right partner. In your 30s, it is growing that career, making money, having kids or raising them. In your 40s, it is your kids’ education, raising them well, trying to hold everything together. In your 50s and 60s, it is health, retirement, finding your footing again as a couple. And your 70s, it is your health and the legacy you leave behind. The safety of the people you love.

We move through these phases like checkboxes. Like if we hit each one on time, we will have lived well.

But here is what I have been sitting with.

You want a career, for what? If you are not enjoying the process of the work. You want a family, for what? If you are not actually present with them. Phones down, eyes up, fully there. You want money for what? To prove your worth while you spend your days doing things that drain you?

Adding why you want something changes everything. It turns a deadline into a direction. It turns a milestone into a meaning.

A lot of what I wanted in my 20s I don’t want anymore. I don’t know whether that is good or bad. But I do know my definition of wealth has changed. And I think that is worth paying attention to.

Calculation That Changes Your Perspective

I did a calculation this week that I really made me think.

I did a calculation this week that stopped me cold.

The average lifespan is 70 years. Let’s say you spend your working years from 25 to 55 in front of a laptop. That is 30 years. 30 years multiplied by 52 weeks is 1,560 weeks. Five working days a week gives you 7,800 working days. At 6.5 hours a day, that is 50,700 hours of your life in front of a screen.

That is almost 6 full years. Gone. Staring at a laptop.

Now look at the bigger picture. If you sleep 8 hours a night, you have roughly 170,000 waking hours in your entire lifetime. And nearly 30% of every single one of those waking hours is spent in front of a laptop.

And that is before you count the scrolling. The commuting. The hours spent doing things out of obligation rather than joy.

So the real question is, of the time that is actually left, how much of it is truly yours?

That number changed something in me this week. Not to spiral into guilt, but to feel the weight of it. Because we move through our days like time is infinite. Like there is always more somewhere. There isn’t. There never was.

There are 96 days left in 2026.

Not next year. Now. And they are going to pass regardless.

The only question is what you do with them.

Don’t wait for the new year to change your life.

Start today. With whatever you have. With wherever you are.

96 days is nothing. 96 days is everything if you decide to use them.

What I’m Reading

Caste: The Origins of Our Discontents -Isabel Wilkerson (Finishing)

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

Careless People: A Cautionary Tale of Power, Greed, and Lost Idealism (Starting)

A scathing whistleblowing memoir by Sarah Wynn-Williams, a former Director of Global Public Policy at Facebook (now Meta). The book pulls back the curtain on the company’s high-level operations, detailing internal decision-making surrounding major global crises, content moderation controversies, and big-tech influence. I want to read this before the movie adaptation of the book comes out: The Social Reckoning.

Things on my Reading Desk

1. Why ‘Identity Permission’ Is the New Competitive Advantage

2. One of AI’s Fiercest Critics Says All the Doom Talk Is ‘Meant to Distract Us

3. The scariest AI doom scenario you haven’t thought about

4. How McDonald’s Is Adapting to a Changing Economy

Note to Self

You have been living in a timebox.

Worrying about the right things at the right ages and hitting the right milestones at the right time. Meanwhile, life is passing, and the things you actually want to do keep getting pushed to the next phase.

There are 96 days left in this year.

Free yourself from the box. Do the things you keep saying you will do later.

Later is not a time. Now is.

Be bold. Be real. Be Anomalous.

— Sai Menon

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

The most unfashionable career advice you’ll hear this year is also the oldest: stay, and get very good at the job you already have.

Between 1980 and 1982, three young people took jobs nobody would put on a vision board. In Michigan, an 18-year-old inspected hood and fender panels at a Pontiac plant, as part of a GM program that helped pay for her college. In 1980, a mechanical engineering student from a Lower East Side housing project started at Xerox as a summer intern. And in Arizona, a community college business student took a seasonal forklift job at Price Club over his holiday break.

Four decades later, one runs General Motors, one ran Xerox, and one runs Costco.

None of them had a master plan. What they had was a floor to stand on and the patience to learn every inch of it.

Under the Hood is Be Anomalous’s long-form series on the people behind the companies, written for anyone in the hard, unglamorous middle of building something. Subscribe to get the next one in your inbox.

I. The Forklift Driver Who Stayed

Ron Vachris was born on Staten Island in 1965. His father was a utility lineman who, after one too many freezing winters working on the poles, moved the family to Arizona when Ron was a teenager.

In 1982, Ron was studying business at Glendale Community College outside Phoenix. Over the holiday break, he took a seasonal job driving a forklift at Price Club, a members-only warehouse store. It wasn’t glamorous. The company was small, with about 17 warehouses. But its founders, Sol and Robert Price, had built a culture of treating and paying people well, and they talked about growing to 200 locations someday.

The break ended, and he didn’t go back. “I’m learning more here in real life than I am at school about business,” he later explained. He decided to stay for a little while and never finished his degree.

After several years on the forklift, he became an assistant warehouse manager in Phoenix. In 1991, the company asked him to help open its first Colorado locations, where he co-managed warehouses in Aurora and Westminster, and by 1992 he was running a third. When Price Club merged with Costco in 1993, the company asked him to go back to Arizona and manage warehouses through the transition. In 1999, he was offered a regional VP role in San Diego overseeing 24 Southern California warehouses, a job he held for a decade. In 2010, headquarters called him north to Issaquah, where he oversaw about 62 warehouses across seven Western states.

Then came the ask that scared him. In 2015, Costco co-founder Jeff Brotman asked him to run real estate. Vachris was stunned. He saw himself as a pure operator whose whole career had been running warehouses. He said yes anyway, scouting sites around the world and learning international business at a founder’s side. He calls it one of the best educations he ever had in global business. The lesson he still repeats to employees: if someone has confidence in you to take on something new, don’t let discomfort talk you out of it.

A year later, then-CEO Craig Jelinek asked him to try something new again: running merchandising and all of Costco’s buying. In 2022, he was named president and COO, and on January 1, 2024, he became only the third CEO in Costco’s history. That fiscal year, revenue grew 5% to $254 billion.

Ask him how he did it, and he won’t hand you a strategy. His father’s advice was “Don’t chase a title.” His own version is just as plain: work alongside great people, pay attention, listen, and learn what they teach you.

Inside Costco, he says, there are plenty of people like him. There’s just only one CEO seat. The numbers back him up: 87% of Costco’s 876 warehouse managers started as hourly employees. Its head of merchandising started as a door greeter. The executive in charge of fresh foods started by cleaning the meat department at night.

Nobody taught Vachris the business in a classroom. He learned it pallet by pallet and warehouse by warehouse, and he kept saying yes each time the company asked him to learn a new part of it.

II. The Girl Who Found the Defects

Mary Barra grew up inside the company before she ever worked for it. She was born Mary Makela in Royal Oak, Michigan, in 1961. Her father spent 39 years at GM’s Pontiac division, starting as a die maker on the assembly line.

Her first job came through the school she chose. The General Motors Institute in Flint, now Kettering University, ran on a co-op model: students alternated between classes and paid work at GM plants. In 1980, at 18, Barra enrolled, and her first assignment was at the Pontiac plant inspecting the hood and fender panels of Pontiac Grand Prix cars. The job paid her tuition. It also gave her an early lesson. She kept finding defects. “It was not a good time for GM quality,” she has said.

She graduated in 1985 with an electrical engineering degree and started as a senior engineer at the Pontiac Fiero plant. GM quickly marked her as management material. In 1988, it gave her a fellowship to Stanford, and she finished her MBA in 1990.

Barra’s career wasn’t a linear path.

First came a job as executive assistant to CEO Jack Smith, a posting GM gave to rising stars. She has said it exposed her to the whole operation. Next, she was asked to fix a struggling internal communications department. In 2003, she took over the ailing Detroit-Hamtramck assembly plant, which led to running vehicle manufacturing engineering from 2004 and global manufacturing engineering from 2008.

Then the company itself broke. Right after GM’s 2009 bankruptcy, CEO Ed Whitacre put her in charge of human resources, a job that isn’t normally on the path to CEO. It mattered anyway: GM needed to keep its best people from leaving so it had the talent to recover, and few left. Her signature move there was small and telling. She cut GM’s 10-page dress code down to two words: “dress appropriately.” Her own HR team pushed back and wanted to add specific rules to the manual. She held the line. She reasoned that if GM trusted managers with millions in budget and teams of people, it could trust them to judge what to wear.

In 2011, CEO Dan Akerson pulled her out of HR to run global product development, a division he described as chaos. She took it on with almost no experience designing cars. She cut the number of vehicle platforms, and in 2013 purchasing and supply chain were added to her responsibilities.

She has said she never set out to become CEO. Her rule was simpler: whatever job you have, own it and “do it like you’re going to do it the rest of your life.”

In January 2014, she became CEO, the first woman to run a Big Three automaker. Weeks later, the teenager who found defects faced the biggest one in the company’s history. In her first year, GM issued 84 safety recalls covering more than 30 million cars, and she testified before Congress about the faulty ignition switch. She told lawmakers the company would do the right thing, and she apologized to the families of those who were hurt or killed. Then she launched “Speak Up for Safety” to rebuild the company’s safety culture.

Twelve years later, she still runs GM, nearly half a century after she first walked onto the Pontiac line.

III. The Intern Who Kept Raising Her Hand

Ursula Burns grew up with what she has described as three strikes against her: she was Black, a girl, and poor. Her single mother, a Panamanian immigrant, raised three children in public housing on the Lower East Side. She took in ironing and ran a daycare from home so the kids could attend Catholic schools. Her highest annual income was $4,400.

Burns calls herself accidental to everything, both the engineer and the executive. As a high school senior, she was good at math and asked a guidance counselor, a nun, what to do next. The counselor offered three options: nun, nurse, or teacher. Burns knew none of those salaries would lift her family. So she went to the library and found a Barron’s guide listing starting salaries by degree. Chemical engineering paid the most, so that became the plan, even though she had no idea what engineers actually did.

She chose Brooklyn Poly because it was close enough to walk home and help her mother. A state opportunity program covered her full tuition and gave her a stipend for the subway and food. She switched to mechanical engineering after deciding she hated chemistry.

Her first real work in the field came before Xerox. She spent two summers at Bell Labs, where a Black engineer named Roland Harris became her first role model. He showed her how the work was done, and also that she belonged there. In 1980, she did a summer internship at Xerox. When she tried to join full-time after graduation, Xerox told her no, not yet. “You need a master’s degree, and we’ll pay.” With a fellowship from the GEM consortium, she finished her Columbia master’s in 18 months and joined Xerox in 1981. She stayed 38 years.

Through the 1980s, she did the unglamorous work of product development and planning. Then she raised her hand. At a 1989 town hall, an employee asked whether Xerox’s diversity push meant lowering hiring standards. Senior executive Wayland Hicks answered casually, and Burns asked him why he would entertain the question at all.

She expected to be reprimanded. Instead, Hicks called her in and offered her a job as his executive assistant. At 31, it felt like a step backward, but she took it, understanding that being close to power was its own education. In June 1991, she became executive assistant to chairman and CEO Paul Allaire. She has described the role as chief cook and bottle washer, essentially a training position. Allaire later recalled asking her what she thought after a string of high-level meetings. Her answer: “I could do your job.”

That training job opened more doors. Vernon Jordan, the civil rights leader and Xerox board member, met her in a hallway, stopped her, and asked why she hadn’t introduced herself. That night he sent her a typed note and three books to read. He remained her mentor for the rest of his life.

From there she ran businesses: the fax and office color business, a copier group in London, and global manufacturing as VP from 1999. In 2000 she became senior VP of corporate strategic services, overseeing manufacturing and supply chain. As Xerox nearly collapsed, she worked alongside Anne Mulcahy, and the two steered the company through it. She became president in 2007 and CEO in July 2009, succeeding Mulcahy. It was the first time one woman handed a Fortune 500 company to another, and Burns became the first Black woman to lead a Fortune 500 company.

Where you are is not who you are.

What Actually Compounds

Look past the titles, and these three stories share a structure.

The floor is the curriculum. Each of them started where the product physically lives: on a forklift in a warehouse, on the line checking panels, in engineering at the drafting table. By the time they reached the top, they understood the business from the bottom, which is where most businesses break. Barra didn’t learn quality from a dashboard. She learned it with her hands at 18.

The detours were the promotions. Burns took an assistant’s job that looked like a demotion. Barra went from manufacturing to communications to HR, then to product development with no design background. Vachris gave up a degree and later moved into real estate and merchandising. Each “sideways” move added a view of the business that specialists never get.

Speaking up raised the ceiling. Burns’s career didn’t take off because she stayed quiet and competent. It took off the day she challenged a senior executive in public. Loyalty got her in the room. Candor got her noticed.

Staying only compounds if the place bets on you. This is the part motivational posts leave out. GM paid Barra’s tuition and her Stanford MBA. Xerox paid for Burns’s master’s. Costco is built on promoting from within. Their patience paid off because each institution invested back. If you’re an employee, pick a place that grows its people. If you’re a founder, you’re building the warehouse someone else will spend forty years climbing, so build one worth staying in.

You Are Not Behind

If you’re three years into something nobody is clapping for, stuck on the forklift, doing the unglamorous inspections, sitting in meetings where you’re the least senior person in the room, these three stories aren’t asking you to hope. They’re asking you to be excellent at the job in front of you, to learn the business from the floor up, to take the strange sideways move, and to raise your hand when it matters.

The invisible years aren’t a waiting room. They’re the foundation.

“Where you are is not who you are.”

Be Bold. Be Real. Be Anomalous.

How many open goals do you have right now?

Not the ones you are actively working on. The other ones. The ones sitting in the back of your mind, collecting dust while the years pile on. That pair of skinny jeans you refuse to give away because you will wear them again when you lose the weight. That set of paints sitting in the corner of your room because you will start painting again someday. That business idea you keep revisiting in your head, when things are more stable, when the time is right, when you feel ready.

We all have them, and we keep them open like tabs on a browser we never close, convincing ourselves that keeping them open is the same as working on them.

It isn’t.

You Have To Say Yes To Be Saved

There was a man whose town was hit by a terrible flood. The waters rose fast. He climbed to the roof of his house and held on, and he prayed. He prayed for God to save him. For a miracle to come.

A neighbour came by in a rowboat. “Get in; I will take you to safety.”

The man shook his head. “No. God will save me.”

The waters rose higher. A rescue team came by on a motorboat. “Sir, get in. We will get you out of here.”

Again he refused. “God will send a miracle. I am waiting.”

The waters kept rising. A helicopter appeared overhead and dropped a ladder.

“Grab on; this is your last chance.”

He waved them away. “God will come.”

And the waters took him.

When he arrived at the gates of heaven, he looked at God and said, “I prayed. I believed. Why didn’t you save me?”

And God said, “I sent you a rowboat. A motorboat. A helicopter. What were you waiting for?”

Act Now, or That is Our Story

If we don’t act, this can be our story.

The flood is life going by, the years piling on while you wait for the perfect moment.

The man drowning is you, watching your life pass, your goals collecting dust, convincing yourself you will come back to them.

The people offering help are the opportunities knocking on your door at the right moment, the person who showed up, the available resource, the window that opened.

Including this: if you are reading this right now, this is your rowboat. This is someone throwing you a line.

Waiting for God to send a miracle is waiting for the perfect conditions: when I am more stable, when I have more money, when the kids are older, when the time is right.

And dying in the flood is arriving at the end of your life with those goals still open, still dusty, still waiting, still unbegun. Looking back at all the boats you waved away.

The opportunities knock. The doors open. The rowboats come. And we wave them away because it wasn’t the miracle we imagined.

And the years go by.

I looked at my own life recently and got honest about something uncomfortable. I have open goals that have been open for years. Things I keep telling myself I will come back to. And I realised keeping them open indefinitely was its own kind of trap. Because an open goal with no deadline is just a dream with nowhere to go.

So I made a decision.

I am giving every open goal in my life a deadline. A real one. Either I am moving toward it, starting now, starting small, starting with whatever I have, or I am closing it. Permanently. Not because I am giving up. But because I would rather know now that something is not for me than wake up ten years from now and realise I spent a decade waiting to begin.

Clarity is a gift. Even when it hurts.

The Systems I Created

Because wanting to change is not enough.

You need a system. Here is what I put in place.

1. The Open Goal Audit.
   Write down every open goal you have been carrying. Every single one. Get them out of your head and onto paper. Then, next to each one, write honestly: Am I moving toward this, or am I just keeping it alive because letting go feels like failure?

2. The Deadline Rule.
   Every open goal gets a deadline. Not a vague “someday.” A specific date. By this date, I will have taken these specific steps, or I am closing this goal and freeing up the mental space it has been occupying.

3. The Start Small Rule.
   You don’t have to overhaul your life to start. If you want those jeans to fit, go for a walk today. Watch what you eat this week. Something small is infinitely more powerful than nothing at all. Because small things compound. And years from now you will be grateful you started, even if you started small.

4. The Close With Intention Rule.
   If a goal gets to its deadline and you have not moved, close it. Consciously. Not with guilt. With intention. Say this is not for this season of my life. And mean it. Because carrying dead weight disguised as hope is one of the most exhausting things we do to ourselves.

The boats are coming. They have been coming. The question is whether you are going to get in.

Because the flood is not waiting. And neither is your life.

What Else Dropped This Week

Off Script

She Lost Her Mom. Then She Built a Company | Lekha Vyas

Under the Hood

Gloria Steinem: The Legacy She Left Behind

What I’m Reading

Caste: The Origins of Our Discontents -Isabel Wilkerson (Finishing)

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

Careless People: A Cautionary Tale of Power, Greed, and Lost Idealism (Starting)

A scathing whistleblowing memoir by Sarah Wynn-Williams, a former Director of Global Public Policy at Facebook (now Meta). The book pulls back the curtain on the company's high-level operations, detailing internal decision-making surrounding major global crises, content moderation controversies, and big-tech influence. I want to read this before the movie adaptation of the book comes out, The Social Reckoning.

Things That Happened Around

1. Warren Buffett’s last lesson as chair: Culture and capital require different guardians

2. Angela Duckworth Says Successful People Share 1 Habit: They Ask for Help

3. Why The “K-Shaped Economy” Really Matters

Note to Self

Life is hard. Some weeks more than others. And some days it feels like the water is rising and the boats have stopped coming, and you are just out there, alone on that roof wondering how everyone else seems to be holding it together.

They aren’t. Not always. We are all in this together, figuring it out, falling behind, starting over, trying again. Nobody has it completely sorted. We are all just showing up as best we can with what we have.

And here is what I want you to remember.

You have more power than you think. More than the circumstances suggest. More than the hard week is telling you. More than the open goals and the dusty dreams and the years gone by are making you feel.

The life you want is not out of reach. It is just waiting for you to decide you are worth the effort of building it.

So take a breath.

You are not behind. You are not too late. You are not alone.

Now get back up. The boats are still coming.

Be bold. Be real. Be Anomalous.

— Sai Menon

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

What she’s building next in female hormone health

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

🎧 Listen to the episode

YouTube | Spotify | Apple Podcasts

Favorite Quote

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

Favorite Books

The Alchemist by Paulo Coelho

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

In This Episode

In this conversation:

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

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

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

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

Subscribe to Be Anomalous for honest conversations with founders, creators, and cultural disruptors who are building outside the lines.

New episodes drop every Tuesday.

Be Bold. Be Real. Be Anomalous.

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

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

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

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

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

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

Birth Of An Icon: A Bunny Tale

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

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

A Revolution Was Born

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

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

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

Her Legacy Continues.

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

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

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

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

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

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

New article every Thursday.

Be Bold. Be Real. Be Anomalous.

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

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

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

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

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

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

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

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

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

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

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

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

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

Over time, that changed.

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

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

But this conversation goes far beyond investing.

We talk about:

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

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

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

• What she calls her “practical MBA”

• How to think about risk before making your first investment

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

• What Solai looks for when evaluating founders

• Why execution matters more than simply having a great idea

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

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

• The power imbalance that can exist when founders raise capital

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

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

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

• What it means to build a portfolio career

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

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

• How confidence can become more internal over time

• What Solai is learning about the next generation of founders

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

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

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

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

🎧 Listen to the episode

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Favorite Quote

“Leap and the net will appear.”

Favorite Books

The Life-Changing Magic of Tidying Up by Marie Kondo

Quit by Annie Duke

In This Episode

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

New episodes drop every Tuesday.

Be Bold. Be Real. Be Anomalous.

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Let me tell you a story.

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

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

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

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

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

The second farmer never looked up.

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

I was the first farmer this week.

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

I had attached success to being a good person.

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

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

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

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

So here is what I am taking into this week.

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

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

And stop looking over the fence.

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

Let’s have a great week.

What Else Dropped This Week

Off Script

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

Under the Hood

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

What I’m Reading

Caste: The Origins of Our Discontents -Isabel Wilkerson

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

Start with Yourself - Emma Grede (Finishing)

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

Things That Happened Around

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

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

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

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

5. The New Map of AI Power

Note to Self

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

But only if you are tending it.

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

Be bold. Be real. Be Anomalous.

— Sai Menon

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

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

Every Business Before This One Was a Test Run

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

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

The Debt Nobody Talks About

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

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

Built With No Producer, Paid For By No One

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

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

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

The Tweet That Did What No Ad Budget Could

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

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

Choosing Ed Thorp Over the Killers

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

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

Lessons from David Senra

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

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

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

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

2. Find something you genuinely care about

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

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

3. Persistence is a competitive advantage

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

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

4. Work extremely hard

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

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

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

5. Think for yourself

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

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

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

6. Focus requires saying no

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

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

7. Learn from failure without letting it define you

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

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

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

8. Build before you have validation

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

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

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

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

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

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

10. Don’t optimize your life only for money

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

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

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

11. Protect your attention

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

Constantly switching between things makes deep work much harder.

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

12. Become a lifelong learner

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

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

13. Look for patterns across many people’s lives

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

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

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

14. Use history as a shortcut

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

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

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

15. Build something that can compound

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

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

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

16. Your circumstances don’t determine your ceiling

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

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

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

17. The goal isn’t to imitate successful people

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

It’s about understanding how they thought.

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

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

New article every Thursday.

Be Bold. Be Real. Be Anomalous.

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

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

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

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

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

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

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

But this conversation goes far beyond business strategy.

We talk about:

• Why James left academia and had to teach himself business

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

• Why being willing to look foolish can accelerate your learning

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

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

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

• The unconventional path to becoming an independent consultant

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

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

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

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

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

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

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

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

James doesn’t romanticize entrepreneurship.

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

🎧 Listen to the episode

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Favorite Quote

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

Favorite Book

Never Split the Difference by Chris Voss

In This Episode

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

New episodes drop every Tuesday.

Be Bold. Be Real. Be Anomalous.

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

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

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

“Only those who dare to fail can succeed.”

No Business Connections, Just a Magazine Article

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

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

The Persistence

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

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

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

Building the Machine, Then Walking Away From It

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

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

The Freedom to Fail, on Purpose

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

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

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

From a Garage Idea to the Defending Super Bowl Champions

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

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

What the Whole Arc Actually Says

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

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

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

The work you put in will be rewarded.

New article every Tuesday.

Be Bold. Be Real. Be Anomalous.

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The FIFA World Cup does something to people.

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

Patriotism.

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

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

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

So what does patriotism mean for someone like me?

Which country do I wave the flag for?

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

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

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

But here is why this actually matters.

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

And denial is exhausting.

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

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

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

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

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

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

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

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

What I’m Reading

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

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

Start with yourself - Emma Grede (Finishing)

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

Note to Self

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

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

Stop waiting. Start living.

Be bold. Be real. Be Anomalous.

— Sai Menon

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

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

Fidji Simo’s career completely breaks that model.

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

Starting Without a Map

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

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

The Unglamorous Years

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

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

Ten Years Inside One Machine

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

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

Running a Company You Didn’t Build

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

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

Trading a CEO Title for a Bigger Bet

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

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

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

A Pause, Not an Ending

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

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

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

A Career Measured Beyond the P&L

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

What Actually Compounds

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

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

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

New article every Tuesday.

Be Bold. Be Real. Be Anomalous.

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

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

Starting Late, Starting Small

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

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

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

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

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

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

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

The Hotel Order That Changed the Trajectory

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

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

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

A Meeting That Was Supposed to Last Thirty Minutes

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

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

What Nearly Three Decades of Patience Bought Her

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

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

If You’re in the Middle of the Hard Part

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

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

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

The work you put in will be rewarded.

New article every Tuesday.

Be Bold. Be Real. Be Anomalous.

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Episode Description

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

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

But this conversation goes far beyond branding.

We talk about:

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

• The confidence gap women are taught to live with

• Negotiating your worth and unlearning the need to stay small

• Why startup founders need courage more than certainty

• Building brands that take risks instead of playing it safe

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

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

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

• Why slowing down can actually make you a better leader

• What separates brands that survive from those that disappear

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

🎧 Listen to the episode

YouTube | Spotify | Apple Podcasts

Favorite Quote

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

Favorite Book

Out in the Woods by Gregg Olsen

In This Episode

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

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

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

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

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

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

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

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

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

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

(42:00) Raising confident children and redefining success

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

New episodes drop every Monday and Thursday.

Be Bold. Be Real. Be Anomalous.

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

It is the person who has everything.

Think about that for a second.

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

But then you start climbing. And something shifts.

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

And here is the other thing.

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

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

That is not the point.

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

You are.

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

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

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

What I’m Reading

Crush It - Gary Vee (Reading)

I want to use this as a guide for building.

Never Split the Difference - Chris Voss(Reading)

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

What Else Dropped This Week

Off Script

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

Under the Hood

The Attention Arbitrage Engine

Note to Self

Keep your blinders on.

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

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

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

Keep going.

The journey is the point. It always was.

Be bold. Be real. Be Anomalous.

— Sai Menon

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

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

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

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

Run one: the proof of concept

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

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

Run two: turning himself into the asset

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

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

Run three: selling the engine to everyone else

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

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

Run four: the same bet, made with money

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

What founders can actually take from this

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

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

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

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

New article every Tuesday.

Be Bold. Be Real. Be Anomalous.

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