Latest insights
Sharp, fast-moving commentary on capital markets, venture, and the founders moving them.
The SPAC vs Direct Listing Decision Tree for 2026 Founders
Navigate 2026's public markets: SPAC, direct listing, or IPO? Decision tree, real numbers, and founder playbook for late-stage startups.
Stripe's $100B Secondary: What It Means for Late-Stage Comps
Stripe's secondary pricing signals a $100B valuation. Here's what it means for late-stage startup valuations, comps, and fundraising strategy in 2025.
Stripe's 2026 Valuation and What It Says About Fintech Comps
Stripe hits $91.5B in 2026. Here's why its valuation resets fintech benchmarks and what it means for founders raising Series A through C rounds.
How to Structure an Employee Secondary Without Angering Investors
Master employee secondaries: avoid investor friction with transparent pricing, clean mechanics, and strategic timing. Real examples included.
Sunday Data: The Vertical AI Comp Sheet for Feb 2026
February 2026 vertical AI valuation multiples, ARR benchmarks, and funding data for founders and investors. Real comp sheet with 15+ named companies.
Sunday Pick: The Single Best Term Sheet Library on the Web
The definitive guide to the web's best annotated term sheet libraries. Find templates, understand key terms, and negotiate like a pro.
Sunday Read: 12 Founder Memoirs Worth Your January
12 founder memoirs to read in January. Real lessons from Phil Knight, Sam Altman, Reid Hoffman, and more. Insights on fundraising, scaling, and startup life.
Syndicate Math: How Small Checks Become Big Funds
Learn how angel syndicates pool small investments into major rounds. Explore carry, fees, and real-world math behind turning $25K checks into $5M+ funding.
Tax Implications of Secondary Sales: The Founder Cheat Sheet
Essential tax checklist for founders selling equity before exit. QSBS, capital gains, holding periods, and counsel questions explained.
Thanksgiving Reading: 12 Venture Essays Worth Revisiting
Essential venture essays every founder and investor should read before 2026. Timeless insights on fundraising, cap tables, valuations, and startup strategy.
The Book Every Founder Should Read Before 2026
The essential book for your founder archetype, technical, GTM, ops, or finance. Strategic reading before 2026 to sharpen your edge.
The Case For the $100M Seed Round: A Rebuttal
Why mega-seed rounds of $100M+ are rational in the AI era. A data-driven rebuttal to conventional VC wisdom on seed sizing.
Sunday Feature: The LP Quietly Backing Half the AI Seed Funds
Discover which LP is behind a massive share of AI seed funds. Inside the capital strategy reshaping venture capital in 2024-2025.
Tiger Global's 2026 Comeback: Real or Narrative?
Is Tiger Global's return to growth-stage AI deals real? We break down LP evidence, term sheet shifts, and what founders should expect.
The Ultimate Guide to Running a Secondary Tender as a Founder
Master secondary tenders: tax structuring, investor communication, employee eligibility, and timing. Real examples and step-by-step playbook for founders.
Valuation Reality Check: How to Know If Your Ask Is Insane (or a Bargain)
Master startup valuation methods, benchmarks by stage, and negotiation tactics. Learn if your ask is defensible or delusional with real numbers.
The VCs Who Went Silent in January, and What It Means
Why top VCs slowed deal pace in January 2026 and what it signals for portfolio companies, founders, and the venture market ahead.
Vinod Khosla's Bets on Industrial AI: A Five-Year Review
Analyze Khosla Ventures' industrial AI portfolio outcomes over five years. Real data, patterns, and lessons for seed-stage founders raising capital in.
The Weekly Agentic Startup Brief: What's Raising and Why
Track this week's agentic AI startup funding rounds. Real deals, real valuations, real thesis commentary on autonomous agents reshaping enterprise.
What Changed in the 409A Market From 2022 to 2025
How 409A valuations shifted post-ZIRP: rising rates, down rounds, and what founders need to know about option pricing and equity strategy in 2025.
Sunday Deep-Dive: Why Benchmark Still Only Makes 6 Bets a Year
Why Benchmark Capital limits itself to ~6 investments annually. Explore their concentrated strategy, equal partnership model, and what it means for founders.
Why 'Dilution Anxiety' Hurts Pre-Seed Founders Most
How fear of equity dilution at pre-seed leads founders to raise too little, stalling growth and weakening Series A outcomes. Real numbers inside.
Why Founders Quietly Prefer Secondary Sales to IPOs in 2026
Why founders choose secondary sales over IPOs in 2026. Tax efficiency, control, and timing drive the shift away from traditional public markets.
Why Every Founder Should Understand LPs Before Pitching
Learn how LPs shape VC strategy and funding decisions. Understand limited partners to pick better investors and craft pitches that resonate with fund.