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Heyy,

Happy weekend.

Let me tell you about a moment that changed everything.

In 2012, Stewart Butterfield was sitting in a room with 45 employees. He was about to tell them their company is shutting down.

They'd spent 4 years building Glitch - a quirky multiplayer game where you milk butterflies and eggs grow on trees, had raised $17.5 million and had thousands of passionate users.

But 97% of people who tried it left within 5 minutes.

The math didn't work. 

It was simple that the company was dying.

What happened next turned a failed game into a $27.7 billion acquisition by Salesforce.

That's the power of knowing when (and how) to pivot.

Today, we're covering

  • The 3 types of startup pivots and when each one actually works

  • Why Instagram killed an entire year of work to focus on photos (and hit 25,000 users in 24 hours)

  • How Zomato pivoted from restaurant listings to food delivery and captured 52% market share

  • The decision tree that tells you which pivot you actually need

  • Why most founders pivot the wrong thing at the wrong time (and lose everything)

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Today’s Edition

The $50 Billion Mistake Most Founders Make

A few things that kill a startup:

  • Not pivoting when you should.

  • Pivoting when you shouldn't.

  • Pivoting the wrong piece of the business.

According to CB Insights, 42% of startups fail because there's no market need for their product. But here's the thing - most of them had the capability to pivot. They just didn't know which type of pivot they needed.

There are three types of pivots. 

Each solves a different problem. Each has different economics and mixing them up is how you burn through runway changing the wrong things.

---

Pivot Type 1: Product Pivot

What It Is: Same market, different product

When It Works: You have distribution but wrong product-market fit

Case Study #1 Instagram

  • In 2010, Kevin Systrom and Mike Krieger built Burbn - a location-based check-in app inspired by Foursquare. 

  • They raised $500,000 from Baseline Ventures and Andreessen Horowitz.

  • Then they built the whole thing. Full native iPhone app. Complete feature set.

  • And it was terrible.

Systrom later said: "We actually got an entire version of Burbn done as an iPhone app, but it felt cluttered, and overrun with features."

But they noticed something: users were obsessed with the photo-sharing feature. People didn't care about check-ins. They cared about sharing visual moments.

The Pivot:

After a YEAR of work, they threw everything out.

They cut everything except photo, comment, and like capabilities.

8 weeks later, they launched Instagram.

The Results:

  • 25,000 users in 24 hours

  • 10 million users by end of first year

  • $1 billion acquisition by Facebook in 551 days

Same investors. 

Same market (mobile social). 

But different product.

They didn't need to find new users. They needed to build what users actually wanted.

Case Study #2: Zomato

In 2008, Deepinder Goyal and Pankaj Chaddah launched Foodiebay (later Zomato) as a restaurant discovery platform.

You could browse menus, read reviews and find restaurants.

But you couldn't order food.

For 7 years, Zomato was purely a restaurant aggregator providing menu information, user reviews, and recommendations.

The business model was advertising revenue from restaurants who wanted better placement.

But in 2015, they saw something: smartphone penetration was exploding. 

Food delivery infrastructure was maturing and consumer behavior was shifting.

The Pivot:

In March 2015, Zomato started its food delivery service in India, initially partnering with logistics companies, then acquiring delivery startup Runnr in 2017 to build its own fleet.

Same market (people looking for food). 

Same users (already on the platform). 

But different product (delivery instead of just discovery).

The Results:

  • Acquired Uber Eats India in January 2020, giving Uber 9.99% stake and increasing Zomato's market share to 52%

  • IPO in 2021 as India's leading food delivery platform

  • Processed transactions worth billions while competitors like TinyOwl and Foodpanda shut down

Revenue model shifted from advertising commissions to delivery commissions (18-25% per order) plus delivery fees.

Average order value: ₹350-400

Platform commission: 20-25%

Delivery partner cut: ₹30-50 per order

The pivot unlocked recurring revenue instead of one-time advertising deals.

---

Pivot Type 2: Market Pivot

What It Is: Same product, different market

When It Works: You built something valuable but for the wrong customer

Case Study #1: Slack

Stewart Butterfield (yes, the same guy from the opening) tried to build a game TWICE.

First time: Game Neverending → pivoted to Flickr (acquired by Yahoo for $25 million).

Second time: Glitch → pivoted to Slack (acquired by Salesforce for $27.7 billion).

Let's focus on the second one.

Between 2009-2012, Butterfield's company Tiny Speck built Glitch - a multiplayer game with a devoted cult following.

  • Average paying user spent $70/year. 

  • Had engaged community. 

  • Great retention for those who stayed.

The problem was that 97% of people who signed up left within 5 minutes.

Classic retention leak. 

You can't build a billion-dollar company on 3% conversion.

While building the game, they created an internal tool for team communication. 

IRC wasn't cutting it and emails were chaos.

So they built something better.

The Pivot:

In November 2012, Butterfield announced they were shutting down Glitch.

Then he pitched the team on pivoting to their internal communication tool.

"It's all your team's communication in one place, synced, searchable, and available wherever you go", he said.

Same product (the tool they'd already built).

Different market (enterprise teams instead of casual gamers).

The Results:

- August 2013: Announced Slack

- February 2014: Public release, grew 5-10% weekly

- First 6 months: 16,000 users registered without any advertising

- October 2014: Raised $120M at $1.2B valuation - just 2 years after shutting down Glitch

- December 2020: Salesforce acquisition for $27.7 billion

Gaming monetization: $70/year per user, 3% conversion, high churn

Enterprise SaaS: $8/user/month standard, $15/user/month plus tier, annual contracts, <5% churn

Same infrastructure with the same team but different buyer with 10x better unit economics.

Case Study #2: Paytm

In 2010, Vijay Shekhar Sharma launched Paytm (Pay Through Mobile) with $2 million as a prepaid mobile and DTH recharge platform.

You'd use Paytm to top up your phone and pay your bills. That's it.

Market: Individuals who needed convenience for bill payments.

Product: Digital recharge platform.

But in 2014, Sharma saw the smartphone revolution coming. Digital payments were nascent but growing.

The Pivot:

In 2014, Paytm launched its digital wallet service, transforming from a bill payment utility to a digital payments platform.

Same product (digital transactions platform).

Different market (moved from bill payers to anyone making any digital payment).

But in November 2016, India demonetized ₹500 and ₹1000 notes. Overnight, Paytm went from 120 million wallets to 180 million wallets.

The tagline "Paytm Karo" became synonymous with digital payments in India.

The Results:

  • By January 2014, Indian Railways and Uber added Paytm Wallet as payment option

  • January 2014: Paytm Wallet captured estimated 80% market share in digital wallet segment

  • 2017: Launched Paytm Payments Bank

  • 2021: India's largest IPO at ₹18,300 crore ($2.2 billion), exceeding Coal India's 2010 record

Bill payment model: Low-margin utility, one-time transactions

Digital wallet model: Transaction fees, merchant commissions, cross-sell financial services

The pivot didn't change the technology. It changed who was paying and why.

---

Pivot Type 3: Business Model Pivot

What It Is: Same product, same market, different revenue model

When It Works: You have product-market fit but wrong monetization

Case Study #1: Netflix

In 1997, Reed Hastings and Marc Randolph founded Netflix as a DVD-by-mail rental service.

The first model was pay-per-rental - customers paid for each DVD.

First Pivot (Within DVD Business)

September 1999: Introduced monthly subscription concept

By early 2000: Dropped per-rental model entirely for flat-fee unlimited rentals without due dates or late fees

Same product (DVDs by mail). 

Same market (movie renters). 

But different business model (subscription vs. transactional).

The Results of First Pivot:

- By 2002: 600,000 subscribers

- May 2002: IPO, raised $82.5 million at $15/share

- By 2005: 4.2 million subscribers, mailing 1 million DVDs per day

But Hastings knew DVDs were temporary. The company was literally called Net-Flix (internet + movies).

Second Pivot (Streaming)

2007: Netflix launched streaming service

Initially bundled streaming with DVD subscription, starting with around 1,000 titles

January 2008: All rental-disc subscribers got unlimited streaming at no additional cost

Same market (people who want to watch movies at home). 

Different delivery mechanism. 

Different cost structure.

The Failed Pivot Attempt:

2011: Netflix tried to split DVD and streaming into two entities - Netflix for streaming, "Qwikster" for DVDs, coupled with price hike

Result were that 800,000 subscribers canceled, stock price plummeted 77%

Hastings reversed it immediately.

Third Pivot (Original Content)

2013: Released House of Cards, first original series, produced for $100 million over two seasons

Business model shift: From content distributor to content creator.

Why?

Because licensing costs were killing margins and studios were pulling content to launch their own services.

The Results:

  • By 2020: Netflix spent over $17 billion annually on content production

  • By 2010: More than 20 million subscribers, streaming overtook DVD as primary revenue source

  • 2025: 301.6 million paid memberships globally

DVD rental economics: Physical inventory costs, shipping costs, limited scale

Streaming economics: Infrastructure costs decrease per user as scale increases

Original content economics: Upfront investment, owned IP, no licensing fees long-term

Each pivot changed how money flowed through the business without changing the core value proposition: entertainment at home.

The Decision Tree: Which Pivot Do You Need?

Here's how to know which pivot type your startup needs:

Question 1: Do people want what you're building?

→ NO: You need a PRODUCT PIVOT

- Symptom: Users try it and leave immediately

- Example: Instagram (Burbn → photo sharing)

- Fix: Strip to core value, rebuild around what users actually use

→ YES: Go to Question 2

Question 2: Can you reach enough of those people profitably?

→ NO: You need a MARKET PIVOT

- Symptom: Great engagement, terrible CAC or conversion

- Example: Slack (gamers → enterprise)

- Fix: Same product, different buyer with better unit economics

→ YES: Go to Question 3

Question 3: Can you capture enough value to build a sustainable business?

→ NO: You need a BUSINESS MODEL PIVOT

- Symptom: Growth but no path to profitability

- Example: Netflix (rental → subscription → streaming → content)

- Fix: Change how you monetize, not what you build

Insider Takeaway

The companies that survive aren't the ones that never need to pivot.

They're the ones that pivot the RIGHT thing.

Instagram didn't change markets. They changed product.

Slack didn't change product. They changed market.

Netflix didn't change audience. They changed business model.

Remember:

Change ONE variable. Not three.

When you try to change product AND market AND business model simultaneously, you're not pivoting. You're starting over.

And starting over burns cash you don't have.

Most founders are afraid to pivot because it feels like admitting failure.

But:

Systrom threw out a full year of work on Burbn and built Instagram in 8 weeks.
Butterfield shut down a game with $17.5 million invested and built Slack.

The ego cost of pivoting is high.

The financial cost of NOT pivoting is bankruptcy.

Comic As A Collectible:
Teenage Mutant Ninja Turtles #1

You know what's funny about pivots?

In 1984, Kevin Eastman and Peter Laird were broke illustrators sharing a one-bedroom apartment in Dover, New Hampshire.

One night, watching TV, Eastman sketched a turtle with nunchucks as a joke. Laird drew three more. They added "Ninja" and "Teenage Mutant" because it was funny.

They decided to make a comic.

The problem was that they had no money.

Eastman's uncle loaned them $1,200. They printed 3,000 copies at Kinko's.

The Original Comic:

The first TMNT comic was dark, violent, made for adults. The Turtles killed people. It was a parody of Frank Miller's grim 1980s comics.

The Pivot:

When toy companies wanted to license it, most creators would have sold the IP and taken a flat fee.

Eastman and Laird said: "Sure, but we control creative approval and we OWN the IP."

They pivoted from adult indie comic to kids' empire WITHOUT losing ownership.

The Results:

  • 1987: Cartoon becomes #1 kids show in America  

  • 1988: Toy deal generates $1.1 BILLION in first 4 years

  • 1990: First movie, $13.5M budget, $201M box office

  • 2009: Eastman sells his half for $60 million

  • 40 years later: $6+ billion in toy sales, still going

Current Value:

  • CGC 9.8: $90,000+

  • CGC 9.6: $35,000-$50,000

  • Raw first print: $5,000-$15,000

Why It Matters:

They borrowed $1,200 and kept ownership.

Pivoted the audience (adults → kids) while keeping control.

Built generational wealth.

Meanwhile, Jerry Siegel and Joe Shuster got $130 for Superman.

Gerry Conway got $800 for The Punisher (worth $1B+ to Marvel).

Pivoting the business model (work-for-hire → IP ownership) made all the difference.

That $1,200 gamble is now sitting in plastic cases worth $90,000.

Because they knew which thing to pivot.

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