The Curious Engineer

Tomasz Tunguz

2015–2026

1,414 posts

← 2010–2014

2026 167

October 2026

  1. Crossing the Trillion Dollar Chasm
  2. Beyond Automation at OpenAI
  3. Anthropic S-1 Analysis: How 7 Key Metrics Stack Up
  4. The Third Product-Market Fit in AI
  5. How Large is the AI Circle?
  6. Closing Eight Figure Deals in Two Weeks
  7. The GPU Revenue Ladder
  8. What if They're All Clouds?
  9. Price War in the Chip Aisle
  10. The Theory 2026 AI Survey Results
  11. Sales in the Age of AI
  12. A Change in AI Strategy
  13. How to Automate Inbound
  14. Inference Is the Most Important Market in Software
  15. Do We Grow Software or Do We Design It?

September 2026

  1. The Fastest Growing Market in Tech isn't AI
  2. Segmentation Drives Market Share Wins in AI
  3. How GPU Prices Can Double While AI Gets Cheaper
  4. Thinking in Systems, Shipping in Loops
  5. The Most Important Market in AI is the Middle
  6. AI Comes for the If Statement
  7. The Harness Margin Opportunity
  8. When Inbound Sells Itself
  9. What Does Pacing Mean?
  10. Is the 3x AI Productivity Gain just a Computer that Never Sleeps?
  11. The Three Waves of AI Consumption
  12. Concrete, Silicon, & Leverage
  13. The Ads Model for Prompts Vertically Integrates AI
  14. AI Productivity Doesn't Mean What I Thought It Means

August 2026

  1. The Price of Entry to the Frontier
  2. Revenue per Megawatt & The AI Model Factory
  3. NVIDIA's $108b Quarter
  4. How Long Should an AI Agent Live?
  5. The AI Bullwhip
  6. Mainframes became personal. So will your data center.
  7. Previously Unmanufacturable
  8. Birds Don't Fly Like Planes. Neither Does AI.
  9. When Models Learn
  10. Honestly, Who Buys SOTA?
  11. The OpenAI Hack & the Question of Intent
  12. A Winner in Every Category
  13. AI Harness' ARR Multiples
  14. The Secret Chat Room
  15. Spending Like a Hyperscaler
  16. Racing to Sustain Jevons' Paradox
  17. AI is a Terrible Ghostwriter

July 2026

  1. AWS's Road to a Trillion
  2. Microsoft Resells the Frontier
  3. Aftermarket Harnesses
  4. Yeltsin in the AI Aisle
  5. Google's Cloud Revenue Converges to NVIDIA's Growth Rate
  6. AI Engineering Productivity is Anything But Normal
  7. Open Models Tack Toward the Frontier
  8. The Blank Slate AI Strategy
  9. The Harness Is the New Battleground
  10. The AI Colander
  11. Three Years In
  12. 8.9 Million AI Users
  13. The AI Preflight Check
  14. The $10B FDE Boom
  15. AI Worldviews
  16. Most AI Work Can Wait

June 2026

  1. The CIO's Choices are Clear in 2026
  2. When AI Costs More Than the Engineer
  3. What If There Is No Moat Yet?
  4. Full Sail on Asynchronous Inference
  5. Defending Against AI-Powered Attackers
  6. The Quietest Part of Startupland isn't so Quiet
  7. So You Want to Sell Inference
  8. Databricks Widens the Lead on the Yellow Brick Token Path
  9. 5x for Free : The Local Coding Stack
  10. The Golden Age of AI Applications
  11. A CEO's Cost of Capital Advantage
  12. The AI Glass Ceiling
  13. The Substitution Wave in AI
  14. The Minimill of AI
  15. Local in Reality
  16. Intelligence Per Dollar
  17. The Thriving Ecosystem of Open Models
  18. The AI Skepticism Map

May 2026

  1. Skill Distillation
  2. Security in the Age of AI Agents: Office Hours with Jonathan Jaffe
  3. Software After AI
  4. Agent Gravity : Who's Running Your Agents
  5. Plastic User Interfaces
  6. SpaceX's Limitless Ambition : An AI Conglomerate
  7. SpaceX S-1: Project Apex and the $1.75T Conglomerate
  8. SpaceX's Confidential S-1 - The $2 Trillion Rocket Ship
  9. The Unsustainable Subsidy
  10. Observations on Writing with AI
  11. The First Derivative of Inference
  12. What Would AI Email Cost?
  13. The 6 Messages That Actually Matter
  14. 2026 Theory GTM Survey
  15. Localmaxxing
  16. Securing the Agentic Enterprise
  17. AI at Discount
  18. Optimizing Software Factories
  19. All the AI You Need for 8 Ads per Day
  20. This Week's Sign the Apocalypse Isn't Upon Us

April 2026

  1. The $112 Billion Quarter
  2. Timing Cashflows of Your Sales Commissions and Your Customers
  3. Darwinian Specialization in AI
  4. Reorganizing Your SaaS Startup's Organizational Structure to Optimize the Customer Lifecycle
  5. An Often Forgotten Characteristic About Your Startup's Ideal Customer Profile
  6. The Three Questions in AI Sales
  7. GPU Spot Prices Surge 114% in Six Weeks
  8. Technical Schematics: AI Tool Evolution
  9. Competitive Strategy in the Age of AI
  10. Intelligence About Business
  11. A $10 Billion Call Option
  12. A Proactive System of Intelligence for Security
  13. The Beginning of Scarcity in AI
  14. Founders, Equip Your Agents
  15. The AI Problem Matrix
  16. Emerging from the Mythos
  17. Pocket Power : From State of the Art to Your Phone in 23 Months
  18. Tokenmaxxing

March 2026

  1. Marketing in the Agentic Era
  2. Veblen & Jevon Walk Into a Data Center
  3. A New Axis of Competition
  4. AI's Bundling Moment
  5. Cursor, Kimi & the Open Source Imperative
  6. The Pricing Power of Agents
  7. The Robotic Tortoise & the Robotic Hare
  8. The 12x Bet on AI
  9. Hello, Claude? Are You There?
  10. One Billion Lost Packages
  11. The Marginal Hire
  12. The Org Chart Math Behind AI-Native Speed
  13. Is This Tomasz's Agent?
  14. The Sword of Damocles in Software
  15. Data Center Intelligence at the Price of a Laptop
  16. Not Prompts, Blueprints
  17. Would You Buy Generic AI?
  18. Databricks Overtakes Snowflake

February 2026

  1. The Game on the Field Has Changed
  2. Is AI Doing Less & Less?
  3. Why Saudi Aramco Isn't a Proxy for SpaceX
  4. AdSense for AI
  5. SpaceX, OpenAI & Anthropic IPOs : A $3 Trillion Stress Test
  6. 9 Observations from Building with AI Agents
  7. A Third, A Third, A Surprising Third
  8. Will I Be Paid in Tokens?
  9. The AI Acqui-Hire Wave
  10. The 2026 Rotation
  11. Can You Fly That Thing?
  12. How Markets Price AI Risk
  13. Google's 52x AI Growth
  14. The Other Leverage in Software & AI
  15. Building Developer Infrastructure at Scale : Office Hours with Jim Everingham
  16. Dissecting the Internet's Most Novel Creature

January 2026

  1. $281b From One Customer
  2. A Coxswain on Your Shoulder
  3. Is Your Margin My Opportunity in Software?
  4. The Model T Comes to Silicon Valley
  5. AI Managing AI
  6. When the Market Questions Relevance
  7. The Postmodern Data Stack is AI
  8. Software That Debugs Itself While I Sleep
  9. A Third Time Up the Roller Coaster
  10. Dead Companies Walking
  11. Eleven Steps to the Epiphany[^1]
  12. Open APIs Are Over
  13. Trajectory
  14. The Text Box Isn't Enough
  15. The Done List

2025 160

December 2025

  1. Gross Profit per Token
  2. My Favorite Books of 2025
  3. Motive S-1 Analysis: How 7 Key Metrics Stack Up
  4. Scoring 2025's Predictions
  5. Scoring 2025's Predictions
  6. 12 Predictions for 2026
  7. Thursday is Podcast Day
  8. A Flash of Deflation
  9. The Bifurcation in the AI Market
  10. Is Your AI Funded by Junk Bonds?
  11. The Average Founder Ages 6 Months Each Year
  12. The Two Context Databases Powering Enterprise AI
  13. The AI Value Gap : Where Does the $7,000 Per Seat Go?
  14. Streaming Comes into the Fold
  15. From 10 to 31 Tasks Daily : The Agent Inflection Point
  16. Top 10 Posts of 2025

November 2025

  1. Vercel's AI Sales Agent : 10 SDRs Down to 1 in Six Weeks
  2. Private Equity : The New Distribution Channel for AI Startups
  3. The Bacon & the Skillet: When Does the AI Market Congeal?
  4. The Scaling Wall Was A Mirage
  5. What 375 AI Builders Actually Ship
  6. Teaching Local Models to Call Tools Like Claude
  7. Running Out of AI
  8. Datadog: As Reliable as Your Golden Retriever
  9. Are We Being Railroaded by AI?
  10. A 1 in 15,787 Chance Blog Post
  11. OpenAI's $1 Trillion Infrastructure Spend

October 2025

  1. Small Data Becomes Big Data
  2. $555B of Cloud Spend
  3. The Growth Premium Persists in SaaS Valuations
  4. Product-Market Fit is No Longer Static
  5. Engineering for the AI-Native Era : Office Hours with Calvin French-Owen
  6. From Columns to Rewards: Automating the Two Pillars That Drive Modern AI
  7. Where Is Your AI Running?
  8. Good Morning & Good Luck
  9. The Data Pendulum Swings to Consolidation
  10. Is Token Consumption Growth Slowing Down?
  11. Congratulations, Robot. You've Been Promoted!
  12. Building Sales Teams in the Age of AI : Office Hours with Chris Klayko of Databricks
  13. From Books to Prompts: The Instant Future of Productivity
  14. Circular Financing: Does Nvidia's $110B Bet Echo the Telecom Bubble?
  15. Data & AI Infrastructure Are Fusing

September 2025

  1. Adding Complexity Reduced My AI Cost by 41%
  2. From A to B Without Inventing Letters
  3. The Efficient Frontier of AI
  4. The Math of Hypergrowth: Two Paths to the Same Goal
  5. Is T3D2 Dead? Has AI Killed It?
  6. The Post-AI Org Chart
  7. Beyond a Trillion : The Token Race
  8. How AI Tools Differ from Human Tools
  9. Coffee, Omelettes, and Five-Course Meals: A New Software Menu
  10. Developer Relations at Theory
  11. 10 Months into AI Agents : Which Are Used Most?
  12. Two Data Giants, One Revenue Milestone
  13. What It Feels Like to Build in AI
  14. A Living Market Map

August 2025

  1. The $20/Month Software Revolution
  2. The AI Tide Lifts Databases
  3. The Second-Order Effects of AI
  4. Netflix's New AI Role
  5. What Will You Reinvent Today?
  6. A Narrative Violation on a Friday Morning
  7. Achieving Flow with AI
  8. When One AI Grades Another's Work
  9. Explore vs. Exploit in Agentic Coding
  10. The Groupon Era of AI
  11. EvoBlog: Building an Evolutionary AI Content Generation System
  12. Why AI Can't Crack Your Database
  13. What is Chrome Worth?
  14. Who is Talking to My Users?
  15. From Knowledge to Action
  16. Small Action Models Are the Future of AI Agents
  17. The AI-Driven Cloud Market Share Shift

July 2025

  1. Why Seed Rounds Are Growing as Startups Shrink
  2. PageRank in the Age of AI
  3. The AI Search Tipping Point
  4. The Question I Ask Myself Before I AI
  5. The Sales Strategy Conquering the AI Market
  6. Hidden Technical Debt in AI
  7. The Rise of the Agent Manager
  8. Budgeting for AI in Your Startup
  9. The Hungry, Hungry AI Model
  10. Revenue Comes to Crypto
  11. Figma's S-1: A PLG Powerhouse

June 2025

  1. Voice, Context & Control: The Three Pillars of Useful AI Email
  2. Why Data is More Valuable than Code
  3. The Multimodal Lake House : Partnering with Lance
  4. Fighting for Context
  5. DuckLake - Subsecond Latency on a Petabyte
  6. The Data Decacorn Derby
  7. The Coming Wave of Acquihires
  8. Partnering with Maze Security
  9. Patterns Across 5 Years of YC Investing
  10. The IPO Door is Swinging Open
  11. Stuck in the Middle of AI Workflows
  12. What Level of AI?

May 2025

  1. How Monte Carlo's Daily Revenue Model Rewrote Their Strategy
  2. 1000x Increase in AI Demand
  3. A Banner Year for M&A only Five Months In
  4. What's in Your Bank's Wallet?
  5. Theory is Looking for an Investor
  6. My Prompt, My Reality
  7. How AI Redefines User Experience
  8. When Will We Pay a Premium for AI Labor?
  9. Nobody Wants to Read Your Stuff
  10. The Impact of AI on Education & What It Means for Work
  11. A CEO of AI Applications Marks a New Era of AI Competition
  12. An Explosive New Distribution Channel
  13. No Asterisk Needed
  14. 100 Trillion Tokens

April 2025

  1. Semantic Cultivators : The Critical Future Role to Enable AI
  2. When Every Employee Becomes an Agent Boss
  3. A 1600% Improvement in Sales to Lead Conversion
  4. Tokenization as a SaaS Liquidity Option
  5. Rabbits on Firetrucks Redux
  6. Integrations as Competitive Advantage
  7. Social AI
  8. Speed Running a 50 Year Old Software Category
  9. My Bottleneck with AI
  10. Beyond ARR: How Monte Carlo Reinvented Their Business with Daily Revenue
  11. The Impact of Tariffs on Series As
  12. What do Tariffs Mean for Startupland?
  13. A Founder's Guide: Essential Sales Advice for Startups

March 2025

  1. Welcome, Bryan and Philip!
  2. The Great Liquidity Shift
  3. The Price of Distinctiveness
  4. The Digital Hot Dog : Marketing in the Age of AI
  5. The Third UI : The Rise & Fall of the Keyboard
  6. The Implications of the Wiz/Google Deal
  7. Halving R&D with AI & the Impact to Valuation
  8. The Mirage in the Software Clouds
  9. This Analysis Cost 27 Cents
  10. Positioning Startups in the Age of AI
  11. How Much Is A Venture Firm Worth?
  12. Why War & Peace Is Killing Your Data Budget
  13. A Founder's Guide: Essential Management Advice for Startups
  14. Lopsided AI Revenues

February 2025

  1. Four Marketing Principles That Redefine Markets from Klaviyo's Former CMO
  2. The Complete Guide to SaaS Pricing Strategy
  3. AI Fluency : The Next Interviewing Skill
  4. Auctions in AI : Cost of Capital as a Strategic Advantage
  5. The AI Elbow's Impact : What Reasoning Means for Business
  6. Theory is Looking for a Head of AI
  7. Fast-Track Your Growth: GTM & Marketing Office Hours for SF Founders
  8. Faster Sales Cycles & Software Buyer Confidence
  9. AI Impact Curves
  10. Google's Future in Search & AI
  11. $1.2b of Revenue in 30 Days
  12. It Pays to be an AI Company

January 2025

  1. $13b Run Rate & Doubling
  2. Darwin's Finches in AI
  3. The AI Cost Curve Just Collapsed Again
  4. Top Themes in Data in 2025
  5. Top Themes in Data Transcript
  6. What DeepSeek's Newest Model Means for AI
  7. From Blank Canvas to a Brilliant Presentation with AI
  8. Why Synthetic Data Is the Secret Weapon for AI Startups in 2025
  9. Building GTM for AI : Office Hours with Maggie Hott
  10. Tech's $370B Paradox: Why Cash-Rich Giants Might Not Lead 2025's M&A Race
  11. Back to Text: How AI Might Reverse Web Design

2024 120

December 2024

  1. 2025 Predictions
  2. My Favorite Books of 2024
  3. Desktop, Touch, Browser, Now AI? The Next OS in Computing
  4. The Intelligence Imperative: How AI Went From Feature to Foundation
  5. Finding the Midnight Snacker : Agentic Marketing
  6. I Use AI 100 Times Per Hour
  7. Top 10 Posts of 2024
  8. Why I Let AI Grade My Writing (Just Like My AP English Teacher)
  9. The Year Algorithms Learn to Act

November 2024

  1. Theory Two
  2. My Little Library
  3. 75 Cents per Month
  4. Small but Mighty AI
  5. The Post Election Surge is Unevenly Distributed
  6. I Talk to Robots While Driving
  7. The White Collar Revolution
  8. Profit Dollars per GPU Dollar

October 2024

  1. My AI Rube Goldberg Machine
  2. Trends in the Post-Modern Data Stack
  3. Productivity One Year from Now
  4. AI Prompts as PRDs : Why Prompts Will Become Important IP Assets
  5. The Premise of a New S-Curve in AI
  6. Why Lifetime Value is Relevant Again in Software
  7. A Challenge to SaaS Orthodoxy
  8. How M&A Fosters Innovation
  9. Fulfilling Crypto's Original Promise
  10. Where is the Budget for AI Coming From?

September 2024

  1. Would You Listen to AI Generated Podcasts?
  2. Interwoven with Initia
  3. AI Advantage for Startups : Changing the Workflow through Services
  4. Will We See a Better Exit Market Next Year?
  5. Writing Software for Robots
  6. 2024 Theory Ventures Go-to-Market Survey: Optimism Rises Amid Changing Market Dynamics
  7. The New Software GTM Playbook
  8. The Rarity Shibboleth
  9. The Challenge of the AI Demo
  10. Which Design Era Are We In?

August 2024

  1. The Dislocation Between Public & Private Web3 Markets
  2. Higher Levels of Abstraction
  3. What Has Your GPU Done For You Today?
  4. AI Public & Private Premia for AI Companies
  5. Things that Used to be Impossible, but are Now Really Hard
  6. The PostModern Data Stack
  7. Snowflake's 4 Areas of Investment in AI
  8. The Ghost in the Machine : Invisible Ads in Generative Search
  9. The 3 Attributes of an Attractive Market for AI

July 2024

  1. Rewriting the RFP for AI
  2. The Battle for AI Gravity
  3. Agentic Systems' Sales Cycles
  4. The Future of Blockchain Data : Our Investment in Allium
  5. Punctuated Equilibrium in AI : Is it Better to Be A First Mover or A Last Mover?
  6. No SaaS! How AI Agents Will Change Software Pricing
  7. AI Pricing Strategies for SaaS Companies Offering Copilots
  8. Select avg(Moby Dick) limit 2 sentences
  9. The First of Your Newsletters

June 2024

  1. The Four Barriers to AI Adoption
  2. 2024 Theory GTM Survey
  3. How Much Revenue Must a Company Generate to IPO?
  4. The Series A Crunch or the Seedpocalypse of 2024
  5. What about Human Training?
  6. Databricks' Accelerating Growth
  7. Apple's AI Challenger Sale
  8. One Line of Code Can Wipe a Billion Rows : Investing in Tobiko
  9. Is the Software Market in Trouble?

May 2024

  1. The AI Trust Fall
  2. Nvidia 2024 05 23
  3. Chatting With Her - The ChatGPT App on Mac
  4. AI Spending Patterns : It's Not What You Think
  5. BI's Third Form : Office Hours with Benn Stancil
  6. Are AI Companies Valued Differently Than Non-AI Companies?
  7. A Series of Unfortunate Decisions
  8. The Fastest Growing Category of Venture Investment in 2024
  9. The Capex Conquest in the Cloud

April 2024

  1. Massive Acquisitions in Software Startups
  2. When 1% Market Share Shifts Represent $5b of Market Cap
  3. Partnering with Dropzone: Automating Security Operations with AI
  4. A Shift in LLM Marketing : The Rise of the B2B Model
  5. Modern Data Architectures : Jordan Tigani of MotherDuck on Office Hours
  6. Are Software Companies Good Businesses?
  7. The Most Profitable Software Company in Q1 2024
  8. The Market Size Mistake
  9. My Favorite Uses of AI
  10. Extreme PMF : Sustaining Success with Scale
  11. SUI Generis : Office Hours with Evan Cheng of Mysten Labs
  12. The Art of Product Management in the Fog of AI
  13. Micromanaging AI
  14. This Message Will Self-Destruct in 33 Seconds
  15. Rubrik S-1 - Burning the Boats in Data Security

March 2024

  1. AI in the Hands of Software Buyers
  2. Selling AI : Category Creation of a Different Flavor
  3. To Be or Not To Be an Agent
  4. AI SaaS Companies Will Be More Profitable
  5. Analyze All the Things : Data Omniscience with Omni
  6. The Vector Computer Company
  7. Why Databases Won't Charge for Storage in the Future
  8. The Opposite of a Good Idea is a Good Idea
  9. Looking into the Future of BI With Colin Zima
  10. What Happens When AI Performance Asymptotes?

February 2024

  1. What If LLMs Change the Business Model of the Internet?
  2. 3 Key Marketing Tactics for Early-Stage Startups: Lessons from a Former Klaviyo & Lightspeed Executive
  3. The Secrets to Building Vibrant Communities in Web3 Open-Source
  4. The First $100m ARR AI Security Company
  5. Nobody Knows : Steel & Blockchains
  6. One of the Biggest Public Offerings in 20 Years
  7. Building a $20b Behemoth : Office Hours with Steven Goldfeder of Offchain Labs
  8. The Sudden Repricing of Startups in Early 2024
  9. AI Design Patterns
  10. Standard Issue AI

January 2024

  1. Experience as a Status Symbol
  2. The Fastest Growing Software Sectors in 2024
  3. AI Drove the Largest New Bookings of Any New Product
  4. Dissecting Delegation: Diving Deep on The Missing B-School Class
  5. 5th Grade Outlining in Mrs. L's Class : Metawriting before the Age of AI
  6. From Prompt to Paper in 60 Seconds
  7. The Class Missing from Business School
  8. Open Source Models : What Can We Determine from Download Patterns?
  9. The 10x Salesperson
  10. Gordian Knots in Software Engineering
  11. Make Hay When the Sun Shines : Liquidity in Startup Exits
  12. 2024 Predictions

2023 114

December 2023

  1. Why Startup M&A in 2024 Will Rebound
  2. Data Product Teams : Best Practices for a Modern Data Team
  3. Synthesis as Brilliance : Worldly Wisdom from Charlie Munger
  4. Step-Ups & Duration : The Shape of Things to Come to the Series A in 2024
  5. How to Improve Your LLM : Combine Evaluations with Analytics
  6. In Like a Lamb, Out Like a Lion
  7. Top 10 Posts of 2023

November 2023

  1. Managing Data as Product : Office Hours with Philip Zelitchenko
  2. Snow Angels Come Early to Data : Snowflake's Strength Spells Success for Startups
  3. The New Threat to a Data Leader's Career
  4. Who Took a Bet on You?
  5. Sudden Disturbances in Rapidly Moving Objects : The Implications of the OpenAI Fiasco
  6. How Much Does it Cost to Use an LLM?
  7. The First Mac Predates Modern Central Banking
  8. The Software Industry's Productivity Boom: Analyzing Revenue per Employee Trends
  9. Purchasing Patterns in Software : Positivity Punctuating Q3
  10. Top 10 Trends for Data in 2024
  11. Only The Dogged Thrive : More Good News in Startupland
  12. What's Measured is Managed : Earnings Surprise in Public Software in Q3 2023
  13. How Much Should Quotas Increase Next Year?

October 2023

  1. The Impact of Anti-trust on M&A in Startupland
  2. Gas Gas Revolution
  3. AI Reaccelerating Cloud Growth
  4. Top 10 Trends in Data & AI at the Impact Summit
  5. The Convergence of Data & Software Engineering in the Age of AI
  6. Outbound Marketing Fury : Office Hours with Raj Sarkar
  7. What Loom & Klaviyo Indicate about Exit Valuations
  8. The PLG Trap : Lessons Learned from Oliver Jay, former CRO at Asana
  9. The Promise and Pitfalls of Chaining Large Language Models for Email
  10. SaaS Competitive Advantage Through Elegant LLM Feedback Mechanisms
  11. Centaurs & Cyborgs : The Jagged Frontier of AI

September 2023

  1. Artisanal Emails
  2. Avoiding the PLG Trap : Office Hours with Oliver Jay
  3. Building Applications with AI - Lessons from LangChain, Hearth, & Context.ai
  4. Cisco & Splunk Continue the Trend of SaaS Take Privates
  5. Building a Generational Business Databrick by Databrick
  6. 4 Key Takeaways from the AI Panel at Saastr 2023
  7. A Little Yellow Book in the Corner Bookshelf of a Coffee Shop
  8. Whispers of the Future
  9. The Rise of Data Lakes in Software Architecture
  10. The Evolution of Open Source Business Models

August 2023

  1. Context.ai - Unlocking Insight into LLM-Based Applications
  2. A New Marketing Behemoth Klaviyo : How 7 Key Benchmarks Stack Up in the S-1
  3. Around the World in 21 Days
  4. The Dawn of AI : Pricing Power & Profits in NVidia's Business
  5. Mean Reversion: When Will Startup Investing Return to Normal?
  6. Seizing the Moment: Strategies for Startups to Outmaneuver Competition in a Turning Economy
  7. Teaching a Computer to Ghoti
  8. Surprising Data Points about the Venture Capital Market
  9. How Will a Venture Capital Recovery Feel? Observations from 2008
  10. Busting the Myth: Higher Funding Doesn't Mean Faster Hiring in Startups

July 2023

  1. What the New Relic Sale Means for SaaS
  2. The Paradox of AI and Data Roles: How Automation Will Increase Demand for Data Professionals
  3. Signs We've Touched the Bottom
  4. The Pilgrims Raised 4 Rounds of Financing
  5. Operating in the Dark
  6. Producing Charts with AI
  7. The Fracking of Information
  8. There is No Such Thing as Series A Metrics
  9. What 70m Thread Users Mean for B2B Marketers
  10. How Markets Value Software Companies in 2023

June 2023

  1. Picking Teams in AI
  2. MotherDuck - DuckDB in the Cloud
  3. Marketing Teams as Hedge Funds
  4. Does an AI Premium Exist in the Fundraising Market?
  5. What if Every SaaS App Spoke English?
  6. Web3 in SaaS Clothing
  7. The AI API : The Twilio Moment for Machine Learning
  8. How Much More Efficient Should a SaaS Startup Be When Using AI?

May 2023

  1. Observations Using LLMs Every Day for Two Months
  2. When Will SaaS Budgets Increase Again?
  3. The Publicly Traded Company Worth 250x More in 10 Years
  4. High-Flying SaaS Startups' Surge Won't Change the Valuations in Ventureland
  5. How Should You Staff Your Startup in 2023
  6. Which AI Model Should You Pick for Your Startup?
  7. Seeking a Distribution Advantage with AI
  8. Tinkering with LLMs
  9. The Greatest Profitability Turnaround in Software History
  10. When 1 is Bigger than 4 for AI
  11. Every Customer is a Design Partner - Leading Your Sales Motion with Sales Engineering

April 2023

  1. Microsoft's Billion Dollar AI Business
  2. Software Spending Growth Will Accelerate by 40% in 2023, But it Doesn't Feel that Way
  3. Why Every Startup Needs an AI Strategy
  4. How Much will the US Early Stage Venture Market Contract in 2023?
  5. ChatGPT & Taylor Swift
  6. Economics in the Sometimes Strange World of Web3
  7. The 4 Questions Startups Should Ask Themselves about Building with Generative AI
  8. Theory
  9. The Change in Burn Multiple for Startups in 2023

March 2023

  1. Usage as the Moat in AI
  2. The Typical Startup Saw a 24% Increase in Sales Cycle in 2023
  3. The Hardest Round to Raise in 2023
  4. How to Build Your Startup like Google & Stripe
  5. Take a Breath
  6. 2023 Go-to-Market Survey - Understanding How Startups Have Shifted in 2023
  7. How ChatGPT Will Restructure Engineering Teams & Create Opportunity for Startups
  8. Pulp Nonfiction : What I Learned Writing a Blog Post with ChatGPT

February 2023

  1. Magical Metrics with Omni
  2. The Implications of Increased Regulatory Scrutiny for Startup Acquisitions
  3. Which Customer Segments are Healthiest During the Downturn?
  4. A Flare Across the Clouds : Cloudflare's Earnings Report
  5. Venture Capital, Withering & Dying
  6. The Compounding Advantage of a Big Chip Stack in a Downturn
  7. Predicting Cloud Growth Rates for 2023
  8. When AI Favors the Incumbents

January 2023

  1. The Future of Startup Office
  2. Microsoft as a Mirror - What We Can Expect for SaaS in 2023
  3. How Layoffs in Startupland Differ Between B2B & B2C Companies
  4. Is the Suite Strategy Right for Your SaaS Startup?
  5. The Most Acquisitive Acquihirers in Software
  6. Rabbits on Firetrucks : Generating Images for B2B Blog Posts Using AI
  7. 2023 is the Year of _________
  8. The Startup M&A Market Fell 94% Year over Year - But One Segment Thrives
  9. Sizing the Web3 B2B Software Market

2022 124

December 2022

  1. A $30B Software Company from a $15m Investment
  2. My Quest for Speed - Learning to Use My Computer the Fastest Way Possible
  3. From a $200k Annual Burn to Raising $80m+ : Notes from Office Hours with Fredrik Haga
  4. Five Predictions for 2023
  5. A Funny Thing Happened on the Way to Sand Hill Road
  6. My Favorite 10 Books of 2022
  7. What the $6B Coupa Acquisition Means for Software Startups
  8. PLG & Profitability : More Product Doesn't Necessarily Mean Greater Profits
  9. Top 10 Posts of 2022

November 2022

  1. Napoleon's Influence on the Modern Data Stack : hyperdimensional Analysis with Malloy
  2. The Uniswap Token Launch : Tokens as CAC Part II
  3. The Most Successful Web3 Launch in 2022
  4. The Best Time of Year to Raise for Your Startup
  5. A New Chapter
  6. My Laptop is Faster than Your Cloud : Announcing MotherDuck
  7. Office Hours with Fredrik Haga of Dune : What is the Future of Web3 post-FTX?
  8. Soft in the Middle - Examining Your Startup's Org Chart
  9. What the FTX Fiasco Means for Web3
  10. Losing a Month of Runway to Inflation
  11. Cutting R&D to Grow GTM Spend : Is it Happening Across Software Companies?

October 2022

  1. Sales Efficiency through Covid : Reading the Tea Leaves for Startups
  2. Grey Skies in Cloud Earnings
  3. 9 Predictions for Data in 2023
  4. Would You Leave the Cloud to Improve Sales Efficiency by 11%?
  5. Five Pillars of PLG with Carilu Dietrich
  6. Antifragility as a Competitive Advantage in 2022
  7. How Low Could Valuations Go?
  8. Office Hours with Carilu Dietrich - Marketing for Hypergrowth Companies
  9. Just How Troubled is the Bay Area Startup Scene?

September 2022

  1. 10 Predictions for Data at the Impact Summit
  2. Pipeline Supply Shocks in SaaS Sales
  3. Are We Seeing the Beginning of SaaS Consolidation?
  4. The State of Web3 in 2022 through Data
  5. Figma's 50x ARR Multiple & What it Means for Startup Fundraising
  6. Your Customers' Profitability is Your Startup's Future Health
  7. Systematizing Go-To-Market Hiring
  8. Web3 Users Are Just Like Web2 Users
  9. 200% NDR: What Does it Take to Achieve this Stellar Milestone?

August 2022

  1. Don't Look Now But Web3 Companies are Beginning to Trade Like their Web2 Counterparts
  2. Why We'll See More New Types of Web3 Apps in the Next Year
  3. Fundraising in 2022: Where We Are & Where We're Going
  4. Pipeline Analysis Playbook
  5. Omni - A Big Step Forward in the Decade of Data
  6. How to Structure a Startup Sales Team for Optimal Land & Expand
  7. The Trillion Dollar Empire that Started with a Coupon
  8. Growth is No Longer the Best Predictor of a Software Company's Value
  9. Do PE Acquisitions of Public Startups Imply We've Hit a Pricing Bottom?
  10. Messaging: the Bottleneck for Web3
  11. The Math Behind Starting a Successful Software Startup

July 2022

  1. How Much Should You Expect Your Startup to Slow in 2022? About 21%.
  2. Office Hours with Bill Binch: Structuring Sales Teams for Success
  3. The Health of Cloud Spending in Mid-2022
  4. How to Structure Your Sales Compensation Plan to Deliberately Undersell
  5. How Important is Your Software to Your Customer? It's Time to Find Out.
  6. Spot the Difference
  7. PE in VC in 22
  8. The Bid/Ask Spread in Venture Capital
  9. A Masterclass in Sales Development from Lars Nilsson at Snowflake
  10. The Missing Letter from the English Alphabet
  11. 1% of Salesforce's Revenue Makes a Unicorn
  12. Deliberately Underselling as Sales Strategy
  13. The End of Web3
  14. Office Hours with Lars Nilsson, VP of Global Sales Development at Snowflake
  15. When AI Becomes Table Stakes

June 2022

  1. Asking Users to Complete Tough Mudders to Use Your Product
  2. Coinbase & Uniswap: How 7 Key Benchmarks Stack Up
  3. The Web3 Marketing Stack: The Next Big Wave in Crypto
  4. Defending a Startups Greatest Asset through Recession & Recovery
  5. How VCs Value Rainbow Foals in 2022
  6. Bezos' Shareholder Letter in 2000
  7. The Most Popular Financing Round in 2022
  8. What's Better than a Cookie? A Wallet - How Crypto Will Revolutionize Marketing
  9. Office Hours with Lee Kirkpatrick, former Twilio CFO on Managing through Turbulence
  10. The New Key Competitive Advantage for Web3 Startups
  11. Is a 10% Reduction in Staff a Layoff?
  12. Top 10 Insights from the 2022 Startup Sentiment Survey
  13. The Macroeconomic Signal to Watch for Software & Infrastructure Startups

May 2022

  1. Office Hours for 2022 Market Conditions Market Survey Results
  2. The Largest Software Acquisition in History
  3. 2022 Startup Market Conditions Survey
  4. Lessons from Watching a Great CEO Operate
  5. So You Want to Improve Your Sales Efficiency
  6. The 4 Startup States During a Recession
  7. Five Mid-Year Predictions for Web3
  8. How Much Further Can We Fall?
  9. Cash Flow Shockwaves
  10. 5 Key Data Points about the Early Venture Market in Q1 2022
  11. Product-Market Fit in Different Capital Environments

April 2022

  1. The Critical Question Facing Web3 Infrastructure Startups
  2. The Three Eras of Startup Valuations
  3. Imagine You're a Venture Capitalist...
  4. The Rhyming Protocol Wars of 2022
  5. Revenue, Revenue Everywhere. Not a Dollar to Count
  6. Free SaaS Enabled Marketplaces - A Novel Go-To-Market for Software Startups
  7. Four Fundamental Innovations of Web3 that Will Upend Web2 Incumbents

March 2022

  1. $112m of Market Cap per Engineer
  2. Inflation and Deflation in Web2 and Web3 Startups
  3. Startup Self-Repricing as a Recruiting Tool
  4. The Spicy Future for Data
  5. The App Store Model Comes to Web3
  6. Usage Based Pricing: 3 Questions to Ask Before Leaping
  7. Guess the Startup Answers
  8. Guess the Startup
  9. The Three Types of Customer Success Teams
  10. The People Roadmap for Startups
  11. The Future of Money
  12. Rediscovering the Power of the Command Line

February 2022

  1. 1/9/90 in Crypto
  2. The Next Key Innovation in the Shift-Left Movement
  3. Why Early Valuations Might Surge in 2022
  4. The Sales Sandwich
  5. 10 Lessons Learned after $5B of M&A
  6. Will Your Startup Borrow More in 2022?
  7. The New Discipline Web3 Software Companies Must Develop
  8. If You Had $10k to Invest, Which Stock Would You Buy?
  9. Intensity Oozes from these Pages
  10. How Much Money is Flowing into Crypto?

January 2022

  1. Why You Should Expect Your VP Product to Sign Up for a Lead Quota
  2. Dremio - A Foundational Component of the Modern Data Stack
  3. How Will the 52% Correction in the Stock Market Impact the Startup Fundraising Market?
  4. Is Compensation Stagnation to Blame for the Great Resignation?
  5. How Correlated are the Web 2 and Web 3 Software Markets?
  6. Do Data Startups Command a Premium in the Fundraising Market?
  7. The Top Sectors of Web3 in 2022 by Revenue

2021 75

December 2021

  1. My Favorite Books of 2021
  2. Five Predictions for 2022
  3. Mark-to-Market Rounds - What Will Your Startup's Strategy Be?
  4. Tokens as CAC - Are Crypto Companies More or Less Efficient in Acquiring Customers?
  5. The Fifth SaaS Correction
  6. Partnering with Mysten Labs to Build Foundational Infrastructure for Web3
  7. How Stripe Scaled - Notes from Office Hours with Claire Hughes Johnson

November 2021

  1. Samsara S-1: How 7 Key Benchmarks Stack Up
  2. Words Like Loaded Pistols
  3. Justifying Token Equity Multiples using GDP Data
  4. The Need for Two Types of Payback Period Calculations
  5. The 100x ARR Multiple

October 2021

  1. Hex - The Best Product for the Technical Analyst
  2. Using the Reversal Mental Model to Invest Better
  3. Spot.ai - The Future of Video Intelligence
  4. The Two Cap Tables of Crypto Companies: What They Are and How They Relate to Each Other
  5. Passive Investing in Venture Capital and the Parallels to Public Equities
  6. Redpoint Office Hours with Claire Hughes Johnson, former COO at Stripe
  7. Why You Should Repeat Yourself, A Lot
  8. Crypto Companies Insider Ownership is Approaching that of Classic Startups

September 2021

  1. Height - The Project Management Tool for the Modern Worker
  2. The IMPACT Conference on the Modern Data Stack
  3. GitLab S-1 Analysis: How 7 Key Metrics Stack Up
  4. Scaling and Measuring an Effective Developer Relations Organization
  5. What is the Product the Customer Buys Before They Buy Yours?
  6. How Will We Value a Crypto Token?
  7. Benchmarking Amplitude's S-1: How 7 Key Metrics Stack Up

August 2021

  1. Per Seat or Per Use Pricing: A Framework for Evaluating the Right Strategy for Your Startup
  2. You'll Never Login the Same Way Again
  3. Preset Cloud - The Visualization Layer for the Modern Data Stack
  4. The Secret to Recruiting Quickly and Retaining Your People
  5. The Optimal Pricing Strategy for Your Startup - Office Hours with Madhavan Ramanujam

July 2021

  1. The Velocity of Money in Startupland
  2. Can You Guess This Business's Name?
  3. The Decline of Venture Debt at the Early Stage
  4. Data Meshes, Apache Iceberg & Project Nessie - Novel Ideas in the Data World
  5. The Journey From Fortune 100 Executive to Startup Entrepreneur
  6. The Next Step Forward for Conversational Intelligence - Chorus & ZoomInfo
  7. My Mental Model for the World of Crypto
  8. Innovation in the Financial Markets: Seventy Years of Hedge Funds

June 2021

  1. The Great Game of Risk Played in Category Creation, and Why the Winning Strategy is Aggression
  2. The Productivity Implications of Working from Home Across 150,000 Employees
  3. The Figures that Will Move the Venture Capital Market in the Next 3-5 Years
  4. Executive Recruiting as Competitive Advantage - The 3 Knock-On Effects of Failed Executive Hires

May 2021

  1. The Inflationary Forces in Startupland
  2. The One Force that Will Govern How We Return to Work

April 2021

  1. Never Raising, Always Raising
  2. How to Cut a Path through the Jungle of Regulatory Compliance
  3. Covid's Impact on Software Sales Efficiency
  4. Would You Work for This Person?
  5. The Identity Crisis Facing Open Source Companies in the Cloud

March 2021

  1. UIPath S-1 Analysis: How 7 Key Metrics Stack Up
  2. The Importance of Building & Maintaining Great Developer Documentation
  3. How Selling Has Changed Post-COVID, and How it Will Change Again Afterwards
  4. This is the Most Ridiculous Use of Money Management I've Ever Heard. What is Wrong with You?
  5. How Much is 20% More NDR Worth to Your SaaS Startup?
  6. The Feedback Loops in Data that Will Change SaaS Architecture

February 2021

  1. The Four Types of Startup COOs
  2. The Most Popular Startup Domain Suffixes - .com, .co, .gg - Which is Best for Your Business?
  3. The Most Effective Tools and Techniques for Selling Today - Office Hours with Jim Benton
  4. How Much Should You Bet To Maximize Your Investments, or Your Company's Odds of Success?
  5. Eliminating Data Downtime with Data Observability - Why We Partnered with Monte Carlo Data
  6. How to Be a Great COO: Lessons Learned Leading a Unicorn to Success
  7. A Common and Critical Mistake When Forecasting Next Year's Bookings

January 2021

  1. The Five Flavors of ARR - New Definition, Same Great Multiple
  2. The Secret to Keeping Your Software Running and Keeping Customers Happy
  3. Information as Surprise - Harness Claude Shannon's Key Idea
  4. Internal Communication - Why it Matters More than Ever & How to Succeed
  5. Cloud Data Lakes - The Keystone to the Decade of Data
  6. The Fastest Growing Sectors of Startup Fundraising in 2020
  7. The Art of Doing Science & Engineering
  8. The Missing Insight Around Software Multiples for Valuing Companies
  9. Information Cascades - How Many Rational People Can Make Logical Decisions and Yet Still Create a Bubble
  10. The Next Chapter for StackRox
  11. Why Remote Work Changes the Nature of Leadership, and the Kinds of Leaders to Recruit in Startups

2020 99

December 2020

  1. Why Fast Learning Curves are So Important to Startups
  2. 5 Predictions for 2021
  3. Do You Lose Sales Opportunities Because of Sales Execution or Product Insufficiency?
  4. The Three Questions to Ask When Hiring Your Startup's Head of Sales
  5. Where to Start if You're Curious about Macroeconomics Today
  6. Top 10 Learnings from Startups to a $100M+ ARR General Manager, Linda Tong
  7. Building a Product-Led Growth Machine: Office Hours with GC Lionetti

November 2020

  1. It's Supposed to Be Hard. You're Changing the World.
  2. Voodoo, Obsidian & Zettlekasten - A Modern Way of Taking Notes
  3. How a Merger of Salesforce and Slack Would Change the SaaS Landscape
  4. The Supercharger Boosting Startupland Fundraising and Exits
  5. From Hyper Growth to Hyperscale: What I Learned Managing Small and Massive Teams
  6. More Activity Means More Business. Don't Overthink It.
  7. How Developer Marketing Parallels Consumer Marketing
  8. The Parallels in the Culture Between the Two Category Defining Companies

October 2020

  1. How Many Technologies Can a Company Adopt at Once?
  2. Your Startup is a Series of Cycles
  3. Why IPOs, Direct Listings, and SPACs Will Flourish in Startupland
  4. Just How Inaccurate are Quarterly Venture Capital Activity Reports?
  5. The Mispricing of Software Companies
  6. The 4 States of an Engineering Team

September 2020

  1. Notes from Office Hours with Kimbre Lancaster on How to Run Successful Virtual Events
  2. Redpoint Office Hours with Medha Agarwal & Shopify’s Kaz Nejatian
  3. How to Predict the Forward Multiple of a Software Company
  4. Why Burnout Should be a Topic at Your Next Board Meeting, and What to Do About It
  5. How to Maximize the Impact of Your Website When Targeting Two Personas
  6. Can You Still Make Money Starting a SaaS Company?
  7. Your Responsibility as a Manager is to Hire 7 People
  8. Redpoint Office Hours with Kimbre Lancaster on Hosting Successful Virtual Events

August 2020

  1. A Quick Diagnostic to Determine if Your Sales & Marketing Teams are Aligned
  2. Asana S-1 Analysis - Comparing One Productivity Powerhouse to Another
  3. Why Startups Should Establish Qualifying Signals for Sales Teams Early On
  4. Month Zero Cash-on-Cash Payback - A Metric for Judging Sales Team Growth
  5. Redpoint Office Hours with Tyler McNally from Gainsight
  6. Conflicting Data on the State of the US Early Stage Market
  7. The Secret to Productive Group Meetings over Video
  8. Inside Rounds Have Become a Sign of Strength at the Series B

July 2020

  1. The Five Important Trends in Data, and the One Megatrend Powering Them All
  2. How to Recruit a Marketing Team with Great Product Marketing and Demand Generation Abilities
  3. The Best Economic History Books According to Readers
  4. The Unforeseen Benefits of Online Events
  5. An Economic History of the US in Five Stock Market Crashes
  6. What I've Learned about Modern Monetary Theory
  7. Cloud Data Lakes - The Future of Large Scale data analysis
  8. The Fundraising Market Two Quarters into COVID
  9. Office Hours with Adam FitzGerald, Hashicorp, on Developer Evangelism

June 2020

  1. Two Charts that I've Been Wondering About
  2. Top 10 Learnings from the Redpoint 2020 GTM Survey
  3. What is the Structure of the Typical SaaS Company as it Scales?
  4. How Should You Structure Sales Teams for Optimal Performance?
  5. How Predictive is SDR/BDR Quota Attainment of AE Quota Attainment?
  6. SaaS Office Hours Go to Market Survey Edition & Which Metric Should Your SDR/BDR Team Use?
  7. How to Transform Your Board Meeting with Written Narratives
  8. Notes from Office Hours with Hollie Wegman

May 2020

  1. Where are Most Unicorns Headquartered?
  2. California Dreaming - Is Silicon Valley Still the Best Place to Start a Company?
  3. Office Hours with Hollie Wegman
  4. Three Little Puzzles about Infinity
  5. How Would You Manage Your Business Differently if Shelter-in-Place Lasted 18 Months or More?
  6. Why is the Stock Market Only Down 15%?
  7. The Fundraising Market Has Changed, But Not in the Way I Thought
  8. Redpoint 8 - Our Eighth Early Stage Fund

April 2020

  1. Benchmarking Sales Prospecting Volumes, Deal Terms, and Meetings in the Coronavirus Era
  2. Bullwhip and Base Rates - The Two Major Forces Impacting Startups in Q2
  3. Narrative Economics and the Power of Stories
  4. What Customer Demand and Your Startup Balance Sheets Imply about Your Startup's Strategy
  5. Surveying Sales Leaders - How Coronavirus is Impacting Quotas, Bookings, and Budgets
  6. Why Margin Matters Now in Startupland
  7. Questions about Returning to Work
  8. The Startup Sectors Most Impacted by the Coronavirus
  9. The Next 30 Years of Geopolitics - What Could They Look Like
  10. Observations about Silicon Valley Two Weeks into Quarantine

March 2020

  1. What do Google Search Query Trends Reveal about the Changes in How We Work?
  2. Data Lake Engines - The Essential Layer of the Next Generation Data Architecture
  3. What Will this Crisis Accelerate in Your Ecosystem?
  4. Six Startup Disciplines for Challenging Times
  5. Estimating the Impact of the Coronavirus on Growth
  6. What Could the Venture Market Look Like in the Coronavirus Era
  7. Notes from Office Hours with Lisa Lawson
  8. What I Expect in the Next Few Months in Startupland
  9. The SaaS Marketing Scorecard - How Does Your Marketing Operation Rank?
  10. The Impact of the Coronavirus on Software Valuation Multiples

February 2020

  1. The Great CEO Within
  2. Why Your Startup's Org Chart is Limiting Your Growth
  3. The Strategic Importance of Competition
  4. One of the Most Frequent Errors in Sales Planning and Forecasting
  5. When You Have an Advantage, Speed Up the Game
  6. Office Hours with Lisa Lawson
  7. How Our Journey with Snowflake Began
  8. Mental Models for Hiring Salespeople at Startups
  9. Simpson's Paradox in Measuring Net Dollar Retention Rate

January 2020

  1. Cloud Prem Architecture - The New Way of Serving the Enterprise with a Hub and Spoke Data Model
  2. Has VC Become So Big It Must Be Disrupted?
  3. Trust is at the Core of Software Marketing
  4. What is a Best in Class Payback Period for a Software Company in 2020?
  5. Growing Product and Engineering Orgs from Zero to IPO
  6. The Redpoint 2020 Go To Market Survey
  7. The Health of the US Venture Market in 2020
  8. B2B vs B2C: How Should Your Sales Team Be Allocated to Maximize Success?

2019 86

December 2019

  1. 5 Predictions for 2020
  2. The Top 10 Posts of 2019
  3. How Much Turnover in Your Sales Team Should Your Startup Expect?
  4. Product Launches Become the Operating Cadence of a Startup

November 2019

  1. Benchmarking Your Sales and Customer Success Teams
  2. The 13 Critical Questions to Answer about Your Startup's Product Marketing
  3. The Most Frequent Mishire in Startups
  4. Notes from Office Hours with Nick Mehta
  5. Office Hours with Anthony Kennada on Category Creation on Nov 14

October 2019

  1. A Decade Long Mac User Tries Out Windows for the First Time in 15 Years
  2. The Rise of the Founder-CEO
  3. Welcoming Travis Bryant, Again!
  4. What I've learned about IPOs and Direct Listings
  5. On Humility and Making Better Decisions
  6. Design and Open Source: A Potentially Powerful Combination
  7. The Radically Different Early Stage Fundraising Market
  8. The Early Discipline of Remote Startups

September 2019

  1. The State of the Startup IPO Market
  2. Office Hours with Nick Mehta of Gainsight Oct 9
  3. Little Known Facts about the VC Industry
  4. That Will Never Work
  5. The SaaS Correction of Late 2019
  6. The Siren Song of ROI Based Pricing
  7. A Mental Model for Prioritizing Your Startup's Energies
  8. If You Have Great NDR Retention, Should You Increase Your Marketing Spend?

August 2019

  1. Benchmarking DataDog's S-1: How 7 Key Metrics Stack up
  2. Which Categories of Seed Startups are Thriving? Which Aren't?
  3. The 37% Rule: How to Decide When to Stop Wondering and Start Deciding
  4. One Call to Make Before Picking Your Startup's Headquarters

July 2019

  1. A Clever Hack to Reading More Books
  2. Notes from Office Hours with Guillaume Cabane
  3. The Strategic Question at Seed Today
  4. Private Equity as an Exit Option for SaaS Startups
  5. Observations from the Enterprise Tech 30 List
  6. Why Churn Rates Can Spike When Your SaaS Startup Experiences Hypergrowth
  7. Adding Engineering Metrics to the Redpoint SaaS Metrics Template

June 2019

  1. 100k+ ACV SaaS Companies: Do Their Metrics Differ from Other SaaS Companies?
  2. The SaaS Valuation Environment in Mid-2019
  3. Mattermost's $50M Series B
  4. Theory SaaS Startup Key Metrics Template
  5. Office Hours with Guillaume Cabane on June 27
  6. Setting the Salesforce/Tableau Acquisition in Context
  7. Why Product Innovation Slows After the Series A
  8. Looker Joins Google Cloud

May 2019

  1. As Your Sales Team Scales, Focus on Your Middle
  2. The Benefits of and Questions Facing Remote and Distributed Startups
  3. Before You Raise a Round of Funding, Ask Yourself This Question
  4. Define the What But Delegate the How
  5. The Fundraising Environment in 2019 - Three Major Shifts
  6. How to Develop Best in Class Sales Efficiency
  7. What a Valuation Implies About a Business

April 2019

  1. Benchmarking Slack's S-1: How 7 Key Metrics Stack Up
  2. A Random Walk Down Sand Hill Road
  3. Office Hours with Travis Bryant
  4. The Four Strategic Questions Facing AI Agencies
  5. Hustle As Strategy
  6. Viewing Valuation as a Discount of Future Value
  7. Do SaaS Startups Still Require Less Capital than 10 Years Ago?

March 2019

  1. Five Reasons to Sell End-to-End Products in Early Markets
  2. Benchmarking Zoom's S-1: How 7 Key Metrics Stack Up
  3. Puzzles, Not Problems
  4. Benchmarking PagerDuty's S-1: How 7 Key Metrics Stack Up
  5. Where Have All the Angels Gone?

February 2019

  1. Should Your Startup Employ Both Assisted and Unassisted Trials to Acquire Customers?
  2. The Free Trial Survey on the Saastr Podcast and Hitting a Blogging Milestone
  3. A Lasting and Enduring Gift
  4. AI Superpowers - A History of Chinese Startups and the Implications for the Future of Startupland
  5. Should Your Startup Differentiate On Pricing?
  6. In Defense of Troublemakers
  7. Answering Readers' Questions about the Free Trial Survey
  8. A Common Mistake in Hiring Plans
  9. 1.01^365 = 37.7
  10. Top 10 Learnings from the Redpoint Free Trial Survey
  11. A New Architecture for Next-Generation Software Companies: Announcing Mattermost
  12. The Two Things You Need From Early Customers that Matter More than Cash
  13. Sharing the Learnings from the Redpoint Free Trial Survey

January 2019

  1. What Makes a Great Leader?
  2. Infinity Wells and Deep Work
  3. How Many Managers Will You Need This Year?
  4. How Much ARR Can a CSM Manage?
  5. Serving the People First Enterprise
  6. Eugene Wei's Novel Mental Models for Technology
  7. Welcome, Travis Bryant!
  8. Your Company is a Product Used By Your Employees
  9. Why Share Repurchases Create Large Opportunity Costs for Early Stage Startups
  10. Series A SaaS Startup Benchmarks for 2018

2018 67

December 2018

  1. Just Where Are SaaS Companies Priced After the 2018 Correction?
  2. Predictions for 2019
  3. 5 Most Popular Posts of 2018
  4. My 10 Favorite Books of 2018
  5. Reducing Page Load Times by 90%
  6. Which is More Important: New Account Growth or Account Expansion?
  7. Creative Selection - An Inside Look at Some Key Moments at Apple
  8. Selling Your Product While You Build It
  9. A New Way to Calculate a SaaS Company's Efficiency

November 2018

  1. The Four Stages of Sales Compensation Structures in Early Stage Startups
  2. SAP Buys Qualtrics; 2018 Catapulted to $65B in $1B+ M&A Volume

October 2018

  1. Red Hat's Acquisition - A Triumph of Open Source
  2. SaaS Freemium/Free Trial Survey is Here
  3. Normalization of Valuations in the Public and Private Software Markets
  4. What Does AirBnB's 'Shares for Hosts' Idea Imply for Blockchain?
  5. In Early Markets, Services Can Be a Competitive Advantage

September 2018

  1. Our Investment in Gremlin - Leveraging Chaos to Create Resilient Systems
  2. Three Observations About the Adobe/Marketo Acquisition
  3. How the Economics of Professional Services Have Changed in Software
  4. Elastic S-1 Analysis - Another Open Source Monster
  5. Access is the Scarcest Commodity in Startupland

August 2018

  1. How SaaS Companies are Valued
  2. How Long Should Your SaaS Software Trial Period Be?

July 2018

  1. Jacob's Ladder in the Startup Fundraising Market - How Startups Today Skip a Round of Fundraising
  2. Why Your Startup Doesn't Invest Sufficiently in its Differentiators
  3. The Startup Founder's Almanac
  4. Lessons Learned from 20 Years at the Leading Edge of SaaS
  5. Does Winner Take Most in SaaS?

June 2018

  1. A Deeper Dive into the Dynamics of the Seed Market
  2. Why Series As are Much Easier to Raise in 2018 than the Past 5 Years
  3. What I'm Grateful For
  4. The Three Layers of Management
  5. Our Investment in Kustomer
  6. The Blockbuster Software M&A Market of 2018
  7. Seven Strategic Rationales for the Microsoft/Github Acquisition
  8. When You Hire an Executive, You're Hiring a Network
  9. The 5 Forces Driving Startup Valuations Today

May 2018

  1. The Most Important Book You'll Read All Year
  2. When Will the Next Wave of UI Advances Happen?
  3. An Ode to the OKR - How to Motivate Greater Ambition in Teams
  4. A Crypto-Trading Uber Driver and a Billionaire's Spat over Candy - On The Importance of Sticking to Your Strategy
  5. The Challenge of Uncertainty
  6. Separating The Quality of the Outcome and the Quality of the Decision

April 2018

  1. The Effect of Flush Private Markets on Software IPOs
  2. Why I Overestimate My Contribution to My Team
  3. The Disappearance of the Fundraising Demo
  4. How to Reach More People with Content Marketing by Changing How You Write
  5. The Importance of Time Value of Money for Startups

March 2018

  1. The Salesforce/Mulesoft Acquisition is a Bellwether for the 2018 M&A Market
  2. Where are We in the SaaS Valuation Cycle?
  3. Is Geographic Dispersion of Seed Dollars Really Happening?
  4. Why Does Your Sales Team Lose Deals?
  5. The Clearest Articulation of a Marketing Roadmap

February 2018

  1. Dropbox S-1 Analysis - The King of Freemium
  2. The ROI of Cash Burn for SaaS Startups
  3. Startup Best Practices 27 - How to Use Options to Retain Key Employees in Your Startup
  4. Things to Consider When Designing Your Startup's Logo
  5. Clarity of Purpose - The Competitive Advantage of Focus
  6. The Impact of Blockchain on SaaS
  7. Expanding Your Time Horizon To Scale Your Startup
  8. The Best Bit of Advice on Writing I've Received

January 2018

  1. How to Identify a SaaS Market that Machine Learning Will Disrupt
  2. Yearning for the Vast and Endless Sea
  3. Ten Year's Worth of Learnings About Pricing
  4. An Era of Fundamental and Massive Change - The Capital Markets Innovation of the ICO
  5. 7 Predictions for SaaS in 2018
  6. Jettisoning the Assumptions of Last Year

2017 109

December 2017

  1. Premoney vs Postmoney - Which is a Better Technique for Negotiating?
  2. Meetings Shouldn't Be Boring

November 2017

  1. Managers Must be Insane to Brainstorm in Groups
  2. How Quickly Does Headcount Scale in the Fastest Growing Software Businesses?
  3. The Parallel Between Cryptocurrency and Continentals
  4. An Antifragile Thanksgiving
  5. False Competition - Why Defining Axes of Competition Matters
  6. Disagree and Commit - A Management Principle for Highly Functioning Teams
  7. The False Confidence of the LTV/CAC Ratio for Early Stage SaaS Startups
  8. The Latent Purchasing Power in the SaaS Acquisition Market
  9. Just How Disruptive Are ICOs to the Classic VC Model?
  10. The Implication of Secular Increases in SaaS CAC

October 2017

  1. The AI Agency - A Novel GTM for Machine Learning SaaS Startups
  2. Important Changes in Revenue and Profitability Definitions for SaaS Companies
  3. The Rising Stakes in SaaS
  4. How to Decide With Speed and Conviction
  5. Monte Carlo Simulations of Inside and Outside Sales Teams in a SaaS Startup
  6. Shopify S-1 Analysis - Smiling All the Way to $10B

September 2017

  1. Decision-Making Auditing
  2. How Much Should A SaaS Startup Invest in Sales & Marketing?
  3. Ownership - A Defining Trait of a Leader
  4. Should You Consider Emotional Intelligence When Hiring Your Startup's Team?
  5. The Challenges of the Platform Go To Market
  6. The Theory and Data Underpinning Sales Commission Plans

August 2017

  1. Hiring for a Discipline You Know Little About
  2. Maximizing Productivity on My Commute
  3. Has SaaS Become Commodified?
  4. The Volatility of Multiples in the Public SaaS Market
  5. The Limiting Factor of Voice and Dictation Adoption
  6. Why Cash Conversion Cycle Matters for Your Startup
  7. When, If Ever, Should Profitable Bootstrapped Startups Raise Capital?
  8. Three Big Ideas on Technology Innovation Cycles
  9. How to Decide When To Move Upmarket

July 2017

  1. Labor Arbitrage Comes to Silicon Valley
  2. How Developed is Global Venture Capital Market?
  3. The Quickest Way to Estimate How Much Your Startup Needs to Raise
  4. Self Service Data
  5. The Decline of Investment in San Francisco Startups
  6. The Best Book on the Fundamentals of Selling
  7. Patterns in Startup M&A Processes
  8. The Five Questions You Need to Answer About Your Startup's Strategy

June 2017

  1. Gratitude
  2. Prioritizing Your Startup's Roadmap
  3. Adoption Chain Risk - The Importance of Selling to Everyone in Your Startup's Supply Chain
  4. What the Online Advertising World Can Teach Us about the Evolution of Machine Learning in SaaS
  5. Why Amazon's Acquisition of Whole Foods Matters for Startupland
  6. How to Tell If You're a Great Manager
  7. The Intense Power of a Strong Company Culture
  8. SaaS Fundraising in 2017
  9. Apprenticeship
  10. Plant Trees You'll Never See
  11. The "Hiring The Buyer's Role to Sell" Fallacy

May 2017

  1. Ethics in Machine Learning - An Opportunity for Startups to Lead
  2. Startup Best Practices 26 - Choosing Your Startup's Competitive Strategy
  3. The Unbundling of Excel
  4. Bias Against Creativity
  5. Data Middleware - The SaaS Ecosystem's Response to Fragmentation
  6. Hiring for Bookings Capacity in Sales
  7. The Challenges of Raising Your Series B
  8. The Price Anchoring Effect of Distribution Platforms
  9. The Challenge of Performance Pricing for SaaS Companies
  10. The Bustling IPO Market of 2017
  11. When Statistics Will Mislead You

April 2017

  1. A Spike of Venture Debt in Startups
  2. My Algorithm is Better than Yours
  3. A Tale of Two Go To Market Strategies
  4. Is There a No Man's Land in SaaS ACVs?
  5. When Machine Learning Just Isn't Enough
  6. The Four Dimensions of a Demand Generation Portfolio
  7. SMB or Enterprise - Which is the Better Go To Market in SaaS?
  8. The Asset Allocator in Chief
  9. Startup Best Practices 25 - Bounding the Unknown Unknowns
  10. Managing a User's Trust with Machine Learning SaaS Software
  11. Benchmarking Cloudera's S-1 - How 7 Key SaaS Metrics Stack Up

March 2017

  1. The Most Important Thing I've Learned about Writing
  2. Customer Operations - An Idea for Maximizing Efficient Growth in SaaS Companies
  3. Creating Tension in Your Startup's Marketing Positioning
  4. When Should You Sell Your Startup?
  5. Lies Managers Tell Themselves to Avoid Firing Someone
  6. 5 Charts on the State of the Seed Market in 2017
  7. The Three Types of SaaS Value Propositions
  8. The Best Content Marketers in the World
  9. When to Innovate With Your Sales Process
  10. A Product Manager's Guide to Moving Up Market
  11. Startup Best Practices 24 - Marketing Your Product with Novel Framing to Maximize Sales Success
  12. We are Lent into Each Other's Keeping
  13. The Narrowing of SaaS Valuations

February 2017

  1. Psychology for SaaS Startups
  2. Startup Best Practices 23 - Leveraging The Illusion of Explanatory Depth in Interviews
  3. Three Strategies for Engendering Negative Net Churn in Your SaaS Startup
  4. Benchmarking Mulesoft S-1 - How 7 Key SaaS Metrics Stack Up
  5. How to Improve Your Decision Making by Learning from Computers
  6. How Machine Learning Can Benefit Your SaaS Startup
  7. One of the Hardest Things to Do in Sales
  8. Announcing our Investment in Chorus
  9. Against All Odds in Startupland
  10. Modesty, First Principles and Opportunities for Startups
  11. Which to Prioritize - Churn or Growth?

January 2017

  1. How Much Money Should I Raise for My Startup?
  2. The Software Startup Sectors Raising the Most Capital in 2017
  3. The Biggest M&A Multiple in Software History
  4. Is Machine Learning Overhyped?
  5. One of the Greatest Entrepreneurial Stories Ever Told
  6. Using Chat in Content Marketing - Observations Several Months In
  7. The $100M ARR Customer
  8. What I Learned from Complete Burnout at Work
  9. How Does Your Startup's Management Spend its Time?
  10. Which Round Will Be the Hardest to Raise in 2017?
  11. Benchmarking AppDynamics S-1 - How 7 Key SaaS Metrics Stack Up

2016 134

December 2016

  1. The Top 6 Posts of 2016
  2. Just How Global is the SaaS Startup Phenomenon?
  3. When to Increase Your SaaS Startup's Burn
  4. When is the Right Time for Your SaaS Startup to Train its Sales People?
  5. What is Your SaaS Startup Worth in an Acquisition?
  6. Implications of Monoclouds for as-a-Service Startups - Why Differentiation Matters More than Ever
  7. Winning with Data Available on Audible

November 2016

  1. The Important SaaS Accounting Changes Coming in 2017
  2. How Much to Compensate SaaS Sales Teams for New Sales, Renewals and Expansions
  3. How Should You Allocate Your Startup's OpEx between Sales and Engineering?
  4. How to Create Competitive Advantage for Your Startup with Proxy Metrics
  5. What Percentage of Revenue Should SaaS Startups Spend on Payroll?
  6. The Customer Support Experience of the Future
  7. How to Build Auction Pressure in Acquisitions and Financings
  8. Trends in Early Stage SaaS Fundraising Market of 2016
  9. The Limitations of Data and Benchmarks
  10. Task List Zero - When Inbox Zero Isn't Enough

October 2016

  1. Why Demand Generation Can Be So Challenging For Startups
  2. Your Startup's Competitive Advantage
  3. What is the Optimal Contract Length for Your SaaS Startup?
  4. The Challenge Facing Deep-Learning Powered Startups
  5. How Big is a Typical Software Company Acquisition?
  6. What Can You Remove from Your Product?
  7. The Characteristics of the Most Attractive SMB SaaS Companies

September 2016

  1. Are SMB SaaS Companies Valued Differently than Mid-Market SaaS Businesses?
  2. What's the Maximum Rate of Growth for Your SaaS Startup with Paid Customer Acquisition?
  3. The Pressure to Move Up Market Facing SMB SaaS Startups
  4. Startups as a Second Language
  5. How Should I Think About My SaaS Startup's Burn Rate
  6. Startup Best Practices 22 - Explicit Risk Bundles and Mitigations
  7. Designing a Sales Quota Structure at the Earliest Stages of a SaaS Startup

August 2016

  1. How Much is Your SaaS Startup Worth?
  2. 3 Marketing Insights from a World Class SaaS Marketer
  3. A Breakthrough in Human Computer Interaction
  4. Success Has 1000 Fathers and Failure is an Orphan
  5. Why Understanding Startup History is a Competitive Advantage
  6. The Resurgence in Public Market SaaS Valuations
  7. Event Driven SaaS - The Workflow of the Future
  8. The Biggest Areas of Underinvestment in SaaS Sales Teams
  9. The Clandestine Statisticians Who Changed the Course of the War
  10. Median Startup Valuations and Down Rounds in 2016
  11. Fighting and Leveraging Inertia in Sales
  12. The Most Successful SMB SaaS Acquisition Channel Ever Built
  13. A Structural Pricing Competitive Advantage in SaaS - The Three Part Tariff

July 2016

  1. The Quirky M&A Environment for SaaS Companies in 2016
  2. How Fast Does a SaaS Startup Have to Grow to Survive?
  3. Which of the Three Software Budgets Does Your SaaS Startup Target?
  4. The Smallest ACV to Justify an Inside Sales Team at a SaaS Startup
  5. Flux in the Fundraising Market
  6. Learning to Code in a Whole New Way
  7. Dream Teams: The Characteristics of Billion-Dollar Startup Founders
  8. The Increasing Costs of Real Estate for Startups in San Francisco
  9. The Next Big Shift in SaaS
  10. How Healthy is the SaaS IPO Market?

June 2016

  1. You're in the Business of Selling Promotions
  2. The Two Ingredients of Mastery
  3. How Many Inboxes Do You Have?
  4. The Decline of New SaaS Company Formation
  5. The Four Factors to Consider When Developing Your Startup's Pricing Strategy
  6. Mitigating Myopia in SaaS Marketing
  7. The Impact to Startups of the LinkedIn Acquisition
  8. The Key Ingredient to Disrupting with Machine Learning
  9. Subverting Systems of Record with Chat Bots
  10. When to Scale Sales for Your SaaS Startup
  11. Comparing Two Ways to Build a SaaS Sales Team
  12. The Beginning of Consolidation in SaaS

May 2016

  1. Start with the Premise that Everything is Noise
  2. The 3 Types of Channel Strategies for SaaS Startups
  3. What Average Contract Value is Best for a SaaS Company
  4. The Decentralization of Venture Capital
  5. Is A/B Testing A Good Idea for SaaS Startups?
  6. The Leading Predictor of Series A Valuation for SaaS Companies
  7. Are You Spending Enough Time on Your Startup's Go To Market?
  8. SaaS Companies Are Changing their Growth Strategies
  9. The Rising Importance of Reseller Channels in SaaS
  10. A Key Moment in Time for Vertical SaaS Startups
  11. Is the 2016 Economy a Risk to SaaS Companies?

April 2016

  1. Land, Expand, Retain
  2. Five Charts on the State of the Early Stage SaaS Market in 2016
  3. The Secret of Exceptional Teams
  4. There are Only 3 Pricing Strategies for Your Startup
  5. Just How Far Along Are We In SaaS?
  6. Have VCs Changed Their Seed Investment Strategies?
  7. Party Rounds in Seeds - Just Getting Started or Has the Clock Struck Midnight?
  8. Five Questions About The Future of Chatbots
  9. All New Ideas are Combinations of Old Ideas
  10. Inside-Outside-Bias in Startups
  11. The Optimal Seed Round Strategy - Timing and Size
  12. The Future of Machine Intelligence
  13. Inflation and Deflation in the Startup Fundraising Market
  14. Q1 2016 Startup Investment Trends

March 2016

  1. Winning with Data
  2. The Craft of Management
  3. The Equation that Governs Your Sales Team's Effectiveness
  4. Seizing the User's Point of Maximum Intent
  5. Startup Best Practices 22 - Using Scenario Planning for Strategic Decisions
  6. Your Customer's Top 3 Priorities
  7. Disruptive Innovation in SaaS by Competing with Non-Consumption
  8. The Future of Collaboration - Instant Data
  9. In Every Great Product There's a Bit of Magic
  10. From Modest Roots to $10.7T in Market Cap
  11. A Technology Innovation Leading to a Go-To-Market Advantage
  12. Authenticity in Leadership
  13. The Strategic Shift in Revenue for SaaS Startups as They Scale
  14. What's Really Happening in the US Venture Fundraising Market in Early 2016
  15. Resilience and Telos in Entrepreneurs
  16. The Startup Office of the Future
  17. What Pricing Implies About Product Market Fit for Startups

February 2016

  1. Not All Revenue Dollars Are Created Equal
  2. Benchmarking Exceptional Series A SaaS Companies
  3. Hacking Your To Do List with Your Calendar
  4. The Impact of a Changing Venture Environment on Startup Fundraising Terms
  5. SaaS Office Hours in New York - A Q&A on the State of the SaaS Market
  6. The Power of Open Source to Solve the Data Fragmentation Challenge
  7. Venture Debt for SaaS Startups
  8. The Other Payback Period that Matters in SaaS
  9. How to Become Profitable Faster in SaaS
  10. Mr. Market and the SaaS World
  11. The 57% Drop in SaaS Valuations
  12. The Nature of Leverage in Fundraising Conversations Has Changed
  13. With Smart Software, Sell Ironman Not Robocop
  14. The 12 Things I Know About You

January 2016

  1. Chained Probabilities in Startup Business Models
  2. The Question to Ask Before Starting a Company in 2016
  3. The New UI for SaaS - The Question
  4. 3 Questions for Startups to Answer for Themselves in a Volatile Fundraising Environment
  5. When Data Confounds Our Intuition
  6. The Metric that Matters for Startups in 2016
  7. The Downward Pressure of Public Markets on Startup Valuations
  8. The State of the Startup Fundraising Market in 2016
  9. How Your Startup's Org Chart Changes Your Product
  10. How Many Funnels Does Your Startup's Product Have?
  11. When Startup Compensation Isn't About the Money
  12. The Hottest Startup Sectors in 2016

2015 159

December 2015

  1. A Rich Library of User Onboarding Analysis
  2. Is Now a Good Time to Start a Company?
  3. Are You Present?
  4. Building the Machine - Organizational Design in Startups
  5. Steady and Persistent Growth to $5.5B in Market Cap - The Ultimate Software Company
  6. Pricing for SaaS Enabled Marketplaces - When to Go Free
  7. A Framework to Maximize Your Startup's Hiring Success
  8. Startup Best Practices 21 - Your Startup's Recruiting Scorecard
  9. The Tech Press Cycle and Unicorns

November 2015

  1. The Biggest Buyers of Software Companies in 2016
  2. Startup Best Practices 20 - Managing Oneself
  3. SaaS Office Hours with Maia Josebachvilli on Strategic and Tactical Recruiting Metrics
  4. 4 Lessons For SaaS Startups From Optimizely's Early Days
  5. The Right Kind of Mania
  6. How Much Cash Should Your SaaS Startup Burn?
  7. Benchmarking Atlassian's S-1 - How 7 Key SaaS Metrics Stack Up
  8. 2015 Software Startup IPOs and M&A - What Does the Data Imply for 2016?
  9. SaaS Office Hours at Redpoint with Pete Koomen
  10. 3 Go-to-Market Insights from Kenny van Zant at SaaS Office Hours
  11. What is the Optimal Quick Ratio for Your SaaS Startup?
  12. The Next Major Technology to Shape SaaS

October 2015

  1. What Quota Attainment Reveals About Your SaaS Startup's Go to Market
  2. The Most Transformational Force in US Society
  3. Startup Best Practices 19 - Recognizing the Breaking Points of Your Startup's Management Structure
  4. SaaS Office Hours with Kenny van Zant
  5. Five Words of Wisdom from SaaS Office Hours with Bill Macaitis
  6. How Much Should You Pay Your SaaS Startup's Sales People?
  7. Using Vaporware to Validate a Product Idea and Generate Demand for Your Startup
  8. 5 Mistakes SaaS Startups Often Make with Pricing
  9. The Turbulence in Startupland
  10. Startup Best Practices 18 - Collaborating with Your Customer During Your Sales Process
  11. 8 Customer Discovery Questions to Validate Product Market Fit for Your Startup
  12. SaaS Office Hours at Redpoint with Bill Macaitis
  13. The Essential Go To Market Math for Beating Your SaaS Startup's Growth Targets
  14. The Indicators of True, Strong Customer Demand for a SaaS Product
  15. Startup Best Practices 17 - Strategic Planning Using Your Startup's Fundamental Equation

September 2015

  1. What 10x More Seed Capital Means for Founders
  2. Data Network Effects in SaaS Enabled Marketplaces
  3. Data Design Patterns - The Building Blocks of a Data Driven Culture
  4. The Importance of Payback Period for SaaS Startups
  5. Do Vertical SaaS Companies Benefit from Higher Sales Efficiency?
  6. Vertical SaaS Startups Require Different Go To Market than Horizontal SaaS Companies

August 2015

  1. Why Skillful Fundraising is a Huge Competitive Advantage
  2. Why Bottoms Up Selling is a Fundamental Shift in SaaS
  3. Four Important Data Points about Purchasing Behavior in SaaS
  4. What SaaS Startups Miss in User Onboarding
  5. The Impact of the Stock Market on SaaS Valuations in 2015
  6. Startup Trends from YCombinator's Demo Day
  7. The Number One Objection in the Sales Funnel
  8. The 3 Ways Culture Enables Startups to Scale
  9. Lessons from the 8 Great CEOs
  10. Startup Best Practices 16 - Option Pool Planning
  11. The Magic of Email Snooze
  12. The Implications of Raising a High-Priced Round
  13. Why Startups Are Growing Faster Today than Ever Before
  14. How the Changes in UX Assumptions Create Opportunities for Startups
  15. When Do SaaS Startups Hire Their First VP of Sales

July 2015

  1. Benchmarking Netsuite's S-1 - How 7 Key SaaS Metrics Stack Up
  2. What's Really Happening in the World of Bitcoin Investment
  3. If You Chase Two Rabbits...
  4. Why Consumer Startups Dominate the Megaround Market
  5. We Must Strive to be Ourselves
  6. The Best Goal Setting Frameworks
  7. Take Your Startup to the Limit
  8. How Similar is the Fundraising Environment Today to 2000?
  9. At Some Point, You Have to Move Out of Your Parent's Basement
  10. The Fastest Growing Areas of Startup Investment in 2015
  11. Startup Best Practices 15 - Start With the Why
  12. Startup Investment Trends in 2015
  13. The Most Successful SaaS Sectors
  14. The Increasing Fragmentation of SaaS
  15. Five Charts on the Second Seed Market

June 2015

  1. Trends In Startup Acquisition Market in 2015
  2. Three Data Points on Email List Unsubscribe Patterns
  3. Startup Best Practices 14 - Slash and Burn Your Calendar
  4. The Beauty of Bottoms Up SaaS Businesses
  5. The Impact of Interest Rates on Startup Fundraising
  6. Which Open Source License Should Your Project Use if You Want to Raise Venture Capital?
  7. The Early Winners in the Consumer Hardware Wave
  8. The Disruptive Effect of Open Source Startups
  9. Startup Best Practices 13 - Patience with Unit Economics
  10. Startup Best Practices 12 - Customer Success Compensation
  11. How an $11B SaaS Company Measures Churn
  12. Benchmarking ServiceNow's S-1 - How 7 Key SaaS Metrics Stack Up
  13. The Expanding Role of Marketing in SaaS Companies
  14. Why We're Only Just at the Beginning of SaaS
  15. Welcome, Mina!
  16. Unpacking the Deep Diagnostic Value of LTV/CAC for SaaS Startups
  17. Startup Best Practices 11 - The 9 Box Matrix Talent Model

May 2015

  1. When Should Your SaaS Startup Offer Professional Services
  2. The Health of the SaaS IPO Market
  3. Should You Take Cash or Stock to Sell Your Startup?
  4. The Risk Sales Discounts Impose to Startup Burn Rates
  5. A Very Unusual Book about Startup Culture
  6. The First Generation of the Talent Software Wars
  7. The 4 Teams Within Customer Success Organizations
  8. From $800k to $274M in 4 Years - The Story of Ariba
  9. The Decreasing Follow On Financing Success of Startups
  10. The First Mobile-Only SaaS Company
  11. How Great Unit Economics Enables Startups to Weather the Storm - The Story of WebEx
  12. Startup Best Practices 11 - Practice Negotiations Before the Meeting
  13. Which is a More Efficient Way to Build a SaaS Startup - Bottoms Up or Top Down?

April 2015

  1. How to Make Pretty Charts
  2. What an Acquisition of Salesforce Means for Startups
  3. A SaaS History Lesson – The First SaaS Company's Exceptional Journey
  4. How Important Is It For a SaaS Startup to be Profitable?
  5. Measuring Bookings, MRR, Revenue and Cash for Your SaaS Startup
  6. Why the Bubble Question Doesn't Matter
  7. The Innovator's Solution for SaaS Startups - The Flywheel SaaS Company
  8. How Faster Sales Cycles Become a Competitive Advantage
  9. How Many Unicorns Sell Each Year?
  10. Hacking the Performance Evaluation
  11. The Gamble of the Private IPO
  12. The Innovator's Dilemma for SaaS Startups
  13. Are SaaS Startups Today Worth More than Ten Years Ago?
  14. Startup Best Practices 10 - Building Your Startup's Institutional Memory
  15. The Runaway Train of Late Stage Fundraising

March 2015

  1. 3 Key Ingredients of a Sales Compensation Plan
  2. The 5 Key People in a SaaS Sales Process
  3. The Best Book on Building a SaaS Sales Team
  4. The SaaS Company that Grew from 0 to 4M Subscribers in 2.5 Years
  5. The 5 Marketing Channels of Great SaaS Companies
  6. The Forces in Tension in the SaaS Fundraising Market
  7. Why Your Startup's Churn Rate Affects Your Company's Ability to Plan Its Future
  8. The State of the SaaS Fundraising Market
  9. The Most Important Thing Has Never Been the Numbers
  10. Sales Funnel Optimization for SaaS Startups
  11. The Sudden Growth in Series A Round Sizes
  12. Trends in the Startup Acquihire Market
  13. The Compounding Returns of Content Marketing
  14. The Seed Investment Market in 2015

February 2015

  1. Modeling Your SaaS Startup's Revenue Growth Effectively
  2. Creating the Strangely Familiar
  3. The Three Dimensions of Content Marketing Strategy for Startups
  4. Challenging Your Customers During Your SaaS Startup's Sales Process
  5. The Data Behind the Rule of 40%
  6. The Rising Costs of Scaling a Startup
  7. A Single Report to Measure the Health of Your Startup's Sales Team
  8. Why Managing For Progress is So Important
  9. The Employee Productivity Patterns of Billion Dollar SaaS Companies
  10. The 4 Types of Customer Success Organizations
  11. A Simple Tool to Organize, Remember and Deliver Your Important Presentations
  12. Benchmarks for Employee Stock Based Compensation in SaaS Startups

January 2015

  1. Five Things I've Learned about Content Marketing Strategy
  2. Five Bits of Management Wisdom from Pixar
  3. Benchmarking Salesforce's S-1 - How 7 Key SaaS Metrics Stack Up
  4. The Compression in SaaS Valuations
  5. The Fundraising Patterns of Unicorn SaaS Companies
  6. The Characteristics of the Most Successful Teams
  7. The Increasing Growth Rates of SaaS Companies
  8. Are SaaS Startups Less Profitable than they Used to Be?
  9. Benchmarking Xero's S-1 - How 7 Key SaaS Metrics Stack Up
  10. The Rising Table Stakes in SaaS
  11. My 2 Favorite Gadgets from 2014
  12. The Sales Motions of B2C2B Companies
  13. Benchmarking LinkedIn's S-1 - How 7 Key SaaS Metrics Stack Up
  14. B2C2B Startups - Why Selling with Internal Influencers is so Powerful
  15. 3 Questions about Founders as CEOs in SaaS Companies
  16. The Sudden Shift in SaaS Product Pricing

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