Software

How to Build Technology for People Who Hate Software

Plus 100 side hustle ideas for 2026

How Toast Turned Customer Success Into Automatic Revenue

How a cloud-based, all-in-one platform turned clunky cash registers into a $20B+ restaurant SaaS powerhouse

Inside Descartes’ $651M Roll-up Machine

Plus how to double your luck and obsession in the pursuit of mastery.

The Platform That Turned Neutrality Into a Moat

Plus the future of Profit Snack, insurance options for the self-employed, and how to scale with confidence.

The Playbook That Reshaped American Car Dealers

Plus Value Creation Blueprints and how to scale with confidence.

How Alarm.com Became the Backbone of the Smart Home

Plus Battle Plans, clarity workbooks & how we get tricked into training robots for free.

Shopify's International Blueprint

Why removing payment friction beats price competition.

🅿️ How AirGarage Scaled to 300 Locations Without Building a Single Parking Spot

The art of scaling without spending.

💥 The design tool that turned community into an enterprise sales engine

How a “share first” strategy beat heavyweight sales and pushed revenue to $749 million

The $12B Exit That Defied Venture Logic

How two bootstrapped founders beat venture capital at their own game.

From Bankruptcy to Billions: How CLEAR Built an Identity Empire

What happens when two hedge‐fund vets scoop up a failed biometrics startup for pennies on the dollar with hopes of building the infrastructure for modern identity?

💲 How Segment turned a “worst idea ever” into a $3.2B exit

The billion-dollar company that started as a classroom flop

🖥️ Adobe blew up its business model and it worked

Why Adobe chose friction today for compounding tomorrow

😇How Radical Honesty Built a $20M Business

Take a Look Inside the Startup That Refused to Keep Secrets

📊What Carta Did to Solve a Startup Problem No One Could Crack

The One Idea That Made Carta the Go-To for Equity Management

The landing page builder that rewrote the rules of online marketing

How one marketer’s frustration turned into a SaaS empire

🎤The “unproductive” growth hack that made this SaaS startup a market leader

The startup that grew by talking, not advertising

🩲 The founders who stripped down in public to build a $1 billion company

How this fintech company “hid nothing” to win loyal customers

📅 Would you risk it all on a scheduling tool? He did.

The risky decision that made Calendly unstoppable

💍 The Rise of the $5B Ring

How Notion Built a $10B Business in 10 Years

🏆 The HubSpot Playbook

🧠 The Magic of Microsoft

💰 How Uber Built A $150B Empire

🚀 Becoming the #1 Food Delivery Service