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Sajith Pai

Sajith Pai's newsletter explores venture capital, founder psychology, product-market fit frameworks, and business strategy through eclectic observations on markets, culture, and unconventional thinking. This page collects 46 posts published between April 2020 and September 2026. Recent coverage focuses on Venture Capital & Startups, AI (Horizontal) and Enterprise Software.

46 posts indexed0 in the last 30 daysVenture Capital & Startups · AI (Horizontal) · Enterprise SoftwareVisit site ↗

Saturday, 19 September 2026

1 piece
Skateboarding, TOFU, Love, Currencies↗
Venture Capital & Startups · AI (Horizontal) · Enterprise Software

Sunday, 2 August 2026

1 piece
Stanford, Storytelling, Billionaire Inflation, and Chinese VCs↗
Venture Capital & Startups

Saturday, 20 June 2026

1 piece
Pigeon Poop, Index Cards, Sushi Dreams, and Culture Bank

Sunday, 19 April 2026

1 piece
Bangalore, Barrels, Red Queen, Renaissance, & Bitcoin

Sunday, 8 March 2026

1 piece
Blue Oceans, Trader Joe's, Book Editing, and Annual Letters

Wednesday, 24 December 2025

1 piece
Anaconda, Soulcycle, Power Law, and Top Soil

Sunday, 19 October 2025

1 piece
Moving parades, declining audacity, venture arrogance, and soda cans

Friday, 12 September 2025

1 piece
PMF X-Rays, Extramarital Affairs, Sushi, and Kerala

Friday, 22 August 2025

1 piece
Solo founders, Search funds, good writing as bad triaging, and AGI

Friday, 8 August 2025

1 piece
Chapter 2 of my PMF book! - The Pick

Friday, 1 August 2025

1 piece
Special edition: Chapter 1 of my PMF book!

Thursday, 3 July 2025

1 piece
Cold emails, Dunbar numbers, and non-alcoholic beer

Saturday, 3 May 2025

1 piece
Unicorn Origins, Algorithmic PMF, and Coca-Cola Servings

Friday, 4 April 2025

1 piece
Context Collapse, Context Capital, and Capital Thoughts

Friday, 27 December 2024

1 piece
My fave books, podcasts, and articles of 2024

Friday, 6 December 2024

1 piece
PMF, Cold Mails, Psychological Armour, and Softbank

Friday, 1 November 2024

1 piece
Wisdom Productivity, AI, Illiquid Careers, and the Vague Tech Canon

Friday, 28 June 2024

1 piece
TAM, Bibliophilia, Collision Installs, and 'Touchy Feely'

Saturday, 27 April 2024

1 piece
Indus Valley Report Reminiscences, Strategy, Tokyo Trains, and Birkin Bags

Saturday, 30 December 2023

1 piece
What I enjoyed reading, listening, and watching in 2023

Sunday, 17 December 2023

1 piece
Breaking into VC, Referral-led PMF, Don Valentine, and Charlie Munger

Sunday, 3 December 2023

1 piece
CM2, Loom's PMF journey, Peter Attia on not overthinking nutrition & the Goldilocks fund

Sunday, 22 October 2023

1 piece
A VC reflects on the past five years, VC-Founder conflicts, and the new Jhumpa Lahiri novel

Sunday, 11 June 2023

1 piece
Darwin, Type II errors, AI-generated birthday menus, & Shrinks for VCs

Sunday, 21 May 2023

1 piece
PMF Definitions, 21 Meals, and Why VC Funds are Overstaffed!

Sunday, 15 January 2023

1 piece
The investor product, Silicon Valley's most harmful myth, PLG principles, and more!

Thursday, 29 December 2022

1 piece
Investment Bankers, Stacked-up S-Curves, and Leslie's Compass

Friday, 28 October 2022

1 piece
The Revenue Equation, PMF at Wakefit, and Benchmark Capital

Sunday, 17 July 2022

1 piece
Narrative Capital, How Hinduism Scales, and the PMF Pyramid

Sunday, 19 June 2022

1 piece
The Seed Investor as the Priest-Jester, Propulsion Partners, and Merchant Media

Sunday, 12 June 2022

1 piece
Follow-on rounds, blue collar workers, identifying talent and 'Four Thousand Weeks'

Sunday, 17 April 2022

1 piece
A Report, Two Writings, and Three Readings

Sunday, 30 January 2022

1 piece
Funding videos, the tightening, & 'the yoga of eating'

Friday, 31 December 2021

1 piece
What I wrote & read in 2021

Tuesday, 21 December 2021

1 piece
Shower thoughts, hiring A+ talent, COBOL, & crypto countries.

Thursday, 9 December 2021

1 piece
Idli Dosa Twitter in PeakBengaluru, Gaurav Munjal's reading guy, and the 4 lists.

Saturday, 27 November 2021

1 piece
Product-Market Fit | Mauboussin | Long Nose of Innovation | Remarkable2 Tablet

Sunday, 26 September 2021

1 piece
VCs making fun of VC | Rome | Index Mindset

Saturday, 8 May 2021

1 piece
Settled wisdom | Urbanism | Wuhan virus

Saturday, 1 May 2021

1 piece
A devaluation of privilege | Pitch decks | 3 readings
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