Topic Deep Dives

Deep dives on topics our readers are most interested in

Investor InterviewsFounder InterviewsTopic Deep DivesMarket MapsNewsDeal FlowInvestment MemosBusiness Recaps
Topic Deep DivesTopic Deep Dives
📶 the state of B2B monetization in 2025

📶 the state of B2B monetization in 2025

Software pricing is changing, thoughts on what the automated firm looks like, and thinking through how much your options are really worth

Topic Deep DivesTopic Deep Dives
📶 what's ARR, really?

📶 what's ARR, really?

Thoughts on recurring revenue vs. annual run rate, underwriting small funds on potential, and the investors who have backed the top 100 AI companies

Topic Deep DivesTopic Deep Dives
📶 living an asymmetric life

📶 living an asymmetric life

How to find asymmetric opportunities, it's a bad year to be an emerging manager, why there is so much VC turnover, and how Technology Brothers have taken over the internet

Topic Deep DivesTopic Deep Dives
📶 shots on goal > concentration

📶 shots on goal > concentration

Math on why picking shouldn't be your moat, six types of seed investors, a 10-year look at Series B trends, and some bad data for tall founders

Topic Deep DivesTopic Deep Dives
📶 the case for small funds

📶 the case for small funds

Why LPs are more aligned with small funds, how traditional buying journeys are being disrupted with AI, the state of venture today

Topic Deep DivesTopic Deep Dives
📶 missing the point on secondary narratives

📶 missing the point on secondary narratives

Getting in vs. getting out of positions, pre or post-fall and the idea of hitting bottom, plus Redpoint and Work-Bench raise massive new funds

Topic Deep DivesTopic Deep Dives
📶 what are LPs actually buying?

📶 what are LPs actually buying?

Why LPs back fund managers, the risk aversion of venture, Granola announces new funds, and Chime is filing to go public

Topic Deep DivesTopic Deep Dives
📶 narrative capital (converting attention to equity)

📶 narrative capital (converting attention to equity)

~2,500 words on what I think is the biggest thing going on in venture

Topic Deep DivesTopic Deep Dives
📶 the 21 biggest trends affecting venture

📶 the 21 biggest trends affecting venture

21 of the biggest stories we have broken down over the past few years that give a glimpse into the future

Topic Deep DivesTopic Deep Dives
📶 will we see more or less venture money in five years?

📶 will we see more or less venture money in five years?

Venture in 2030, Ramp data on businesses dropping their ad spend, JetBlue calls it quits on their CVC, and the downside of secondaries

Topic Deep DivesTopic Deep Dives
📶 the future of private market roles

📶 the future of private market roles

Are venture jobs losing their appeal, data is the new oil = fracking humans for their thoughts, and looking for a tech job has never been more confusing

Topic Deep DivesTopic Deep Dives
📶 you should really qualify your LPs

📶 you should really qualify your LPs

Thoughts on qualifying your LPs, Jeff Bezos on asymmetric opportunities, the agentic revolution, and Harvard loses tax-exempt status