Practice the decisions that built
(and killed) every company you know.

PayPal: Pay $20 Per Signup?

It is late 1999. You are a PM at Confinity (the company that will shortly merge with X.com to become PayPal). You have a product that allows people to beam money between Palm Pilots using infrared ports. It's technically impressive, but it's a niche tool for tech geeks in Silicon Valley.

Peloton: Recall the Tread+?

It is April 2021. You are a key executive at Peloton. The company has experienced astronomical, unprecedented growth during the pandemic. You are a cultural phenomenon, a multi-billion dollar darling of Wall Street, and you've just launched the Peloton Tread+, a premium $4,000 treadmill designed to do for running what your bike did for cycling.

Pinterest: Engineer Scarcity?

It is late 2010. You are the first Product Manager at Pinterest. The site is a visual "pinboard" for collecting inspiration, and while the growth is steady, it's limited to a tiny, tight-knit community of designers and hobbyists in the Midwest.

Quibi: Charge a Premium Price?

You are the head of growth at a new streaming startup. The product: ~10-minute "quick bites" of premium-quality video content (scripted shows, Hollywood production values, A-list stars), designed exclusively for mobile-vertical viewing during commute moments. You have $1.75B in raised capital and 50+ shows in the pipeline.

Razorpay: Pivot Inside Regulation

You are one of two co-founders of a fintech startup in India. You spent the first 18 months building a peer-to-peer payments app — imagine Venmo for India, before UPI existed. Adoption is real but slow; growth is constrained by the friction of bank-to-bank transfers (which take 2-3 days to settle in 2014).

The 3AM Margin Call: Clearinghouse Crisis

Pivot in the Middle of a Series A?

You are the CEO of a Series-A-stage AI startup, mid-process on a $15M round. Term sheet from a tier-one lead is signed but not closed; another investor is finalizing diligence. The round thesis is: "AI agent for sales SDR workflows."

Snap Spectacles: Hype or Product?

It's late 2016. You are leading the launch of Snap Inc.'s first hardware product: Spectacles. They are stylish, brightly colored sunglasses with an integrated camera that records 10-second circular videos directly to Snapchat. You've just rebranded the company to "Snap Inc. - A Camera Company."

Betamax vs VHS: Open or Proprietary?

It's 1975. You are a senior executive at Sony. You are about to launch the Betamax, a revolutionary home video cassette recorder. It boasts superior picture quality, a compact tape design, and the unmatched engineering pedigree of Sony. Your objective is simple: own the living room.

Spotify: Moderate Joe Rogan?

It's January 2022. You are the CEO of Spotify.

Tesla: Automate the Model 3 Line?

It's early 2018. You are a senior manufacturing leader at the Tesla factory in Fremont, California. The company is in what Elon Musk famously called "production hell" with the Model 3. Tesla's survival depends on scaling production to 5,000 cars per week. Currently, you are barely scraping together a few hundred.

Theranos: Do You Walk Away?

You are a senior R&D scientist at a high-profile health-tech startup. The company has raised $400M+ at a $9B valuation. The CEO is on the cover of business magazines. Board members include former Secretaries of State and military generals.

TikTok: Secure the Music Rights?

It's late 2017. You are a key executive at ByteDance. You've recently acquired the lip-syncing app Musical.ly for $1 billion and merged it with your own app, Douyin, to create the global powerhouse: TikTok.

Uber: Cold-Start a New City

It is March 2011. You are the Launch Lead for Uber. After a successful but small launch in San Francisco, you are tasked with opening your first expansion city: Seattle. The problem is the "Cold Start." You have zero drivers and zero riders. If a rider opens the app and sees "No Cars Available," they delete the app and never come back. If a driver logs on and gets no rides for an hour, they go back to driving for a traditional limo company. You have a limited budget from Travis Kalanick. You need to create "Liquidity" (the state where a rider can get a car in under 5 minutes) as fast as possible. But Seattle is a different beast than SF. The hills are steeper, the weather is worse, and the taxi lobby is more aggressive. You must decide how to prime the pump. Do you focus your scarce resources on recruiting drivers (Supply) or acquiring riders (Demand)? In the marketplace wars, getting this sequence wrong is the fastest way to burn $10M and fail the expansion test.

Is Your Vibe-Coded App Ready to Ship?

You are the solo founder of an AI-powered scheduling app, built over 4 weekends using Cursor + Claude. The app works. You have: fast onboarding, calendar sync, AI-suggested meeting times, a Stripe checkout, basic auth. ~12 friends are using it daily and loving it. You haven't told anyone outside that circle.

Vine vs Instagram Video

It's June 2013. You are a senior product leader at Vine, Twitter's breakout hit app. You've popularized the 6-second looping video, and the cultural impact is massive. Creators are minting memes, growth is vertical, and the app is fundamentally defining internet humor for a generation.

WeWork: Software Company or Landlord?

It's 2017. You are the Chief Financial Officer at WeWork, working closely with the charismatic and mercurial founder, Adam Neumann. SoftBank, led by Masayoshi Son, has just poured billions into the company, valuing it at an astronomical $20 billion. The mandate from Neumann and Son is simple: blitzscale. Grow at all costs, open locations globally, and dominate the market before anyone else can.

Zomato: Acquire Blinkit?

You are the CEO of a publicly-listed food-delivery company in India. Revenue is ~$1B annualized, ~30% YoY growth. Your closest competitor is similar size. Both of you are noticing the same shift: 10-minute grocery delivery (~$1B category in India, growing 3x year-over-year) has emerged as a new consumer habit, dominated by a 4-year-old startup called Blinkit.

Zoom: One-Click Join at Any Cost?

It is 2018. The enterprise video conferencing market is widely considered "solved." Giants like Cisco (WebEx), Microsoft (Skype for Business), and LogMeIn (GoToMeeting) control 90% of the Fortune 500. They have the sales teams, the security certifications, and the bundled contracts.

OpenAI Ships Hardware. Now What?

You are the founder of a $3M ARR AI productivity app. ~80K paying users at $5/mo on iOS + Android. Your app combines voice notes, AI-summarized meetings, and task extraction. You've been growing 20% MoM.

Nokia: Which Ecosystem Do You Pick?

It's February 2011. You are Stephen Elop, the new CEO of Nokia. You have just authored the infamous "Burning Platform" memo. Nokia's Symbian OS is obsolete, clunky, and hemorrhaging market share. Your internal next-generation OS, MeeGo, is elegant but too slow to develop—it won't have a broad portfolio of devices ready for years.

Netflix: Cannibalise the DVD Business

You are the CEO of a publicly-traded mail-order DVD rental company. ~$1B in annual revenue, profitable, market leader. Your business is at peak: 7M subscribers, ~95% gross margin on each DVD rented through the postal system. Wall Street loves you.

MoviePass: Price It at $9.95?

It is August 2017. You are part of the leadership team at MoviePass. The company has been struggling for years with various pricing models, trying to build a viable subscription service for theatrical movies. Growth has been stagnant at around 20,000 users.

Zune: Take On the iPod?

It is late 2006. Apple's iPod has an iron grip on the portable media player market, holding over 75% market share. More importantly, the iTunes ecosystem is a fortress. Consumers have spent hundreds of dollars buying $0.99 tracks that are DRM-locked to Apple devices.

Microsoft: Give Up Windows First?

You are the newly-appointed CEO of a publicly-traded $400B+ market cap software giant. Your predecessor built the company around two identities: (1) we make operating systems, and (2) Windows is the hill we die on. Every other product — productivity software, servers, mobile attempts, browsers — has been treated as a Windows feature, never as an independent business.

The Reality Labs Pivot

You are the CEO of the world's most dominant social media conglomerate. It is late 2021. Your core business is a money-printing machine, generating over $110 billion in annual revenue, with operating margins north of 40%. You have over 3 billion monthly active users across your family of apps.

MCP: Build on It or Skip It?

You are the CTO of a Series-B SaaS company (~$15M ARR, 80 customers). Your product is a CRM for sales teams with deep integrations into email, calendar, and call-recording tools.

LEGO, 2003: Near Bankruptcy

It is early 2003. You are Jørgen Vig Knudstorp, the newly appointed CEO of The LEGO Group. The company is facing its first-ever deficit in its 70-year history. You are losing $1 million a day. The situation is catastrophic.

Instagram: Clone Stories or Not?

It is mid-2016. You are Kevin Systrom, CEO and co-founder of Instagram.

Google Reader: Kill a Beloved Product

You are the VP of Product at Google in early 2013. The company is in the midst of "Spring Cleaning," a sweeping mandate from the CEO to focus resources on core bets like Android, YouTube, and the new social network, Google+. Every product that isn't moving the needle on these core strategic metrics is under intense scrutiny.

Google+: Enforce Real Names?

It's July 2011. Google has just launched Google+, attempting to challenge Facebook. Early traction is phenomenal. Millions of users are signing up.

Discovery Moved to AI Search

You are the head of marketing at a B2B SaaS company. Organic search drives 40% of your pipeline. In Q2 2026, two of your top 10 keywords dropped from page 1 of Google to "AI Overview included" — Google now answers the query directly with an LLM-generated summary, and your traffic on those keywords is down 35%. Your CEO is asking what's happening.

Foursquare: Split the App in Two?

It's early 2014. You are a PM at Foursquare, one of the most beloved mobile apps in the world. You have built an incredible check-in network driven by a strong social graph and addictive gamification (competing for Mayorships, unlocking badges).

A Model Lab Just Shipped Your Product

You are the CEO of a $4M ARR AI startup. Your product is an AI sales assistant — drafts cold emails, summarizes calls, suggests follow- ups. ~200 customers, mostly SaaS sales teams. You raised a $12M Series A six months ago on the "AI-native sales agent" thesis.

Figma: Build Design in the Browser?

It is 2015. You are the VP of Product at Figma. The design world is dominated by Adobe Photoshop and Sketch. Both are native desktop applications. They are fast, powerful, and industry-standard.

Facebook's Bet on Mobile

It is May 2012. You are a Product Director at Facebook. The company is weeks away from its IPO, and the pressure is suffocating.

Dropbox: Build Virality Into the Product

It is late 2008. You are the Head of Growth at Dropbox. You have a product that people love, but your Cost Per Acquisition (CAC) is killing you.

Digg v4: Redesign for the Mainstream?

It's August 2010. You are the product lead at Digg, the undisputed king of social news aggregation. Your platform defines internet culture, driving massive traffic, breaking news, and boasting a passionate community of millions. A front-page placement on Digg (the "Digg Effect") can literally crash a startup's servers.

Entering the AI IDE War Third

You are the founder of a YC-backed AI IDE startup. 9 months in, ~$400K ARR, 18 customers, a tight 6-person team. Cursor is the category leader (~$500M ARR, $9B valuation). Windsurf is the closest competitor with a different agentic angle.

CRED: Who Do You Let In?

You are the founder of a new fintech startup in India. Your product helps users manage credit card payments — pay all your cards on time through one app, with rewards on each payment. Credit card payment reminders aren't novel; HDFC Bank, ICICI, and Paytm all offer the feature. Your reward structure is interesting but copyable.

Clubhouse: Open the Gates or Hold?

It is mid-2020. The world is in lockdown, and a new app called Clubhouse is the only place where people are "hanging out." It is a live audio social network, and it is currently the most exclusive club in Silicon Valley.

BYJU'S: Too Much Capital, Too Fast

You are the founder-CEO of India's largest education technology company. Two years into a global pandemic, your business is at peak momentum — schools are closed, parents are paying for online tutoring, your subscriber base has grown 5x in 24 months. You've raised over $1.5B in the last 18 months alone. Cash position is ~$2B. Valuation just touched $22B in the most recent round.

BlackBerry Meets the iPhone

It's early 2008. You are a senior PM at Research In Motion (RIM / BlackBerry), the undisputed king of the smartphone market.

Apple Maps: Ship Before It's Ready?

It's mid-2012. You are Scott Forstall, Apple's powerful SVP of iOS Software. For years, Google Maps has been the default, pre-installed mapping application on the iPhone, functioning as a massive driver of consumer value.

Would You Cannibalise the iPod?

It is late 2005. You are a Senior VP of Product at Apple, reporting directly to Steve Jobs.

Amazon Prime: Give Away Free Shipping?

It is late 2004. You are Jeff Bezos, CEO of Amazon.

Amazon's Fire Phone: Ship or Kill?

Step into 2012-2013 as the VP of Product for Amazon's highly secretive phone project. Jeff Bezos is pushing hard for a "Dynamic Perspective" feature (a 3D UI using four custom cameras) to differentiate from Apple and Samsung. Engineering is screaming about battery drain, bill-of-materials (BOM) cost, and schedule delays.

Your Search Traffic Is Collapsing

You're the founder of a 4-year-old B2B SaaS content site. ~$2M ARR. 90% of your pipeline traditionally came from Google organic search — long-form articles, comparison pages, glossary content. You have ~400 pages indexed, most of them ranking page-1 for high-intent queries.

Can an AI Assessment Predict a Good Hire?

You are the VP of Engineering at a growth-stage company. Hiring pace has accelerated — 30+ open engineering roles, ~500 applicants per role. Your recruiting team is overwhelmed, and senior engineers are spending 10+ hours/week in interview loops.

How Much Autonomy Do You Give an Agent?

You are the lead PM on an AI agent product. Your agent reads the user's email, calendar, and CRM, and is designed to help busy founders manage their day. It already drafts reply emails (user reviews them before send) and books calendar holds (auto-confirmed if the slot is free).

Linear: Free Forever for Individuals?

You are the CEO of a new project-management tool for software teams. You've built a faster, opinionated alternative to the dominant incumbent. Your product is meaningfully better — faster, keyboard-shortcut-driven, designed for engineers.

Notion, 2015: Nuke It and Restart?

You are the co-founder of an early-stage productivity startup, two years post-founding, $2M raised, four engineers including the two co-founders. You've shipped a v1 product — a tool that lets users combine notes, tasks, and databases on a single canvas. It has a few hundred power users who love it, but daily-active users are flat and signups have been steady at ~30/day for nine months.

A Rival Shipped Your Roadmap

You are the head of product at a Series-B AI-powered hiring platform. Your team has spent six months designing an "AI candidate screener" — an agent that conducts the first round of interviews asynchronously, summarizes them, and ranks candidates for human recruiters. Beta launch in 8 weeks. Investors are excited.

Stripe: Price at 2.9% + 30c?

You are one of two co-founders of an early-stage payments infrastructure startup. You have a few hundred private-beta developers integrated, the product works, and you're about to make pricing public. Every competitor charges some combination of: setup fees ($500-2000), monthly minimums ($25-100), per-transaction rates (2.5-3.5%), per-transaction fixed fees ($0.20-0.50), and hidden line items (chargeback fees, currency conversion spreads, gateway fees).

Apple Opens Siri: Now What?

You are the CEO of a voice-AI startup. ~$2M ARR. Your moat was "voice + AI in one product" — your assistant runs on iOS and Android, uses your own NLU pipeline plus an LLM backend, and your enterprise customers (call centers, legal intake, healthcare scheduling) pay $50-200/seat/month for it.

Slack: Ship the Internal Tool?

You are the CEO of a venture-funded gaming studio. Five years in, $17M raised, ~50 employees. Your flagship MMO has been live for fourteen months and bookings are still under $1M ARR. Player retention is flat. The board is asking pointed questions about runway.

Zee: Stream the World Cup at Scale

It's June 11, 2026. You are the Head of Product at ZEE5. The FIFA World Cup opening match is ten minutes away. Your dashboard shows 8M concurrent users—double your highest stress test. The "Unite8" launch is on the line. What is the move?

A Better Model Ships. Do You Switch?

You are the CTO and a co-founder of an AI-powered customer support startup. ~$1.2M ARR, 18 months in, Series A close is six weeks out. Your entire production stack runs on GPT-4 — your prompts are GPT-4-tuned, your evals are GPT-4-benchmarked, your enterprise contracts cite "GPT-4" by name in the SLA.

Airbnb, 2008: Out of Runway, No PMF

You are one of three co-founders of a year-old marketplace startup. The product lets travellers pay to stay in strangers' spare rooms or on their couches — verified hosts, verified guests, your platform handles the bookings and takes a cut. Two of you are designers; the third is the engineer who rejoined the team two months ago after a brief detour at another company.