Writing

Most AI now improves when you tell it what’s wrong. Power users and workers have picked up that habit, but it’s still foreign to most consumers, because legacy software taught us someone else fixes it. Closing that gap decides who wins consumer AI, and the bar it sets is headed back to work.

Several AI-generated decks hit my inbox today and I passed on all of them. Founders should use AI, but the pitch that earns a meeting is still the CEO's job.

Nvidia just paid $12.9B for a company doing $150M in revenue. The math only makes sense if you stop thinking about data and domain expertise and start thinking about distribution.

Founders are being told to only send investor updates when they're winning. That's bad advice and AI makes it easier to ignore it.

Two weeks into Carry On: what we've learned about tighter episodes, real disagreement, and building in public.

This is what systemic risk looks like before it becomes a crisis. Not a single catastrophic event. A local shock that propagates

Portfolio envy doesn't just sting. It pulls GPs toward consensus and away from conviction. Someone else's markups say nothing about your portfolio or your ability as a picker.

Venture capital’s incentive structure has quietly shifted from building durable businesses to generating markups fast enough to raise the next fund.

The best non-technical operators were always high agency. What's changing is the ones who stand out now have something on top of it — curiosity and enough technical comfort to find and build their own leverage.

Every good story has a villain. Most startups do too. Sometimes it’s a competitor. Sometimes it’s an old dismissal. Sometimes it’s a past version of yourself. That quiet “I’ll show you” energy, when disciplined, can power the early work.

What do you want it to feel like to be around you? On the energy we project, the aura we exude, and how the world we experience is shaped by what we bring to it.

Loss of belief rarely announces itself. It erodes slowly, over time. At the earliest stages, a CEO’s belief in themselves shapes everything — and sometimes the most powerful intervention is simply telling someone, clearly and sincerely, I believe in you.

enture asks you to believe in the growth and durability of a business long before the evidence is obvious. At the early stages, that belief is a discipline. The feedback loops are slow. The outcomes are far away. The work happens in the waiting.

Gratitude is more than a Thanksgiving ritual. In the chaos of venture and the ups and downs of life, it acts as a daily anchor that keeps the highs in perspective and softens the lows. This week is the reminder. Every other week is the real practice.

A reflection on why real vulnerability, paired with grounded confidence, creates clarity, alignment, and stronger partnerships in startups and venture.

How AI is reshaping VC: speed without strategy isn’t leverage. The firms that win will think deeper, move faster, and stay intentional.

A practical framework for early-stage VCs to manage secondary sales: communicate early, sell 20–30% when a company becomes a fund returner, and do it off strong primary rounds.

A founder’s guide to startup failure—two sets of questions: a post mortem for analyzing the business, the other for self-reflection and personal growth. Designed to help founders learn, evolve, and build better next time.

Startup fundraising often comes down to a choice: accept a fast, preemptive VC offer or run a full process to maximize valuation and control. Each path has trade-offs—this post breaks down when to say yes, when to hold out, and how to use both to your advantage.

Globalization is fraying, tariffs are rising, and AI is the next global arms race. From trade wars to supply chains to geopolitical power plays, here are a few thoughts on the messy future we're all trying to navigate.

Lessons learned in 2024 about VC related to company building, fundraising, hiring, decision-making, and more.

Committing to writing every week in 2025 to gain clarity of thought, memorializing lessons learned, and exploring new concepts with rigor.

Job descriptions across VC could use some help. While there are commonalities across firms regarding what an Associate does, it shouldn't manifest in a

Through 2022 and 2023, I surveyed and spoke with over 50 GPs to be better informed on hiring and developing Associates ahead of expanding the team

Even pre-seed companies without formal should create space for "mock Board meetings" to 1) foster healthy dialogue/debate, 2) drive strategic alignment, and 3) instill strong basic governance.

VCs may not compound returns in the event of a portfolio company failure but can certainly compound reputation.

The social pressures of VC are interesting and definitely makes generational firms the default. I believe it takes greater emotional and intellectual awareness to go against the grain and realize that one does NOT want to build a generational firm.

Process and protocols are about how you do work in a way that produces consistent results. It's a key activity might seem boring but is important to the growth of a firm.