VC fund mechanics, market analysis, investment thesis development, LP relations
Who this is for: VCs, LPs, founders understanding VC dynamics, aspiring investors
110 articles.
I Lost $500,000 on a Bad Deal. Here's the Brutal Lesson I Learned About cap tables.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a cap tables and lost $500,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
Why cap tables Will Be the Most Important Skill for VCs in 2026.— The venture landscape is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of cap tables is about to become the single most critical differentiator for successful investors in 2026. Here's why and how to get ahead of the curve.
I Lost $500,000 on a Bad Deal. Here's the Brutal Lesson I Learned About follow-on investing.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a follow-on investing and lost $500,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
The Truth About SPVs: What Your VC Will Never Tell You.— I've sat on both sides of the table. As a founder, I was often in the dark. As a VC, I learned the unwritten rules of the game. I'm pulling back the curtain on SPVs and revealing what investors are really thinking when they send you that document.
A Behind-the-Scenes Look at How We Use cap tables to Manage Our $100,000M Fund.— People always ask me how we manage our portfolio of 8 companies. The answer is a disciplined system built around cap tables. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
I Lost $100,000 on a Bad Deal. Here's the Brutal Lesson I Learned About dilution.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a dilution and lost $100,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
The Truth About cap tables: What Your VC Will Never Tell You.— I've sat on both sides of the table. As a founder, I was often in the dark. As a VC, I learned the unwritten rules of the game. I'm pulling back the curtain on cap tables and revealing what investors are really thinking when they send you that document.
Why Your Obsession with SPVs is Actually Killing Your Returns.— Every VC blog tells you to focus on SPVs. I'm here to tell you that's terrible advice. I've seen more startups fail because of a premature obsession with SPVs than almost any other reason. Here's the counterintuitive truth about what you should be focusing on instead.
I Lost $500,000 on a Bad Deal. Here's the Brutal Lesson I Learned About follow-on investing.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a follow-on investing and lost $500,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
The Truth About follow-on investing: What Your VC Will Never Tell You.— I've sat on both sides of the table. As a founder, I was often in the dark. As a VC, I learned the unwritten rules of the game. I'm pulling back the curtain on follow-on investing and revealing what investors are really thinking when they send you that document.
Why cap tables Will Be the Most Important Skill for VCs in 2027.— The venture landscape is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of cap tables is about to become the single most critical differentiator for successful investors in 2027. Here's why and how to get ahead of the curve.
The Truth About follow-on investing: What Your VC Will Never Tell You.— I've sat on both sides of the table. As a founder, I was often in the dark. As a VC, I learned the unwritten rules of the game. I'm pulling back the curtain on follow-on investing and revealing what investors are really thinking when they send you that document.
The Truth About secondary markets: What Your VC Will Never Tell You.— I've sat on both sides of the table. As a founder, I was often in the dark. As a VC, I learned the unwritten rules of the game. I'm pulling back the curtain on secondary markets and revealing what investors are really thinking when they send you that document.
We Analyzed 8 Deals: This One Clause in the SPVs Separates the Winners from the Losers.— After analyzing our last 8 investments, a surprising pattern emerged. The founders who negotiated this one specific clause in the SPVs consistently outperformed. I'm breaking down the data and showing you the exact language that correlates with a higher chance of success.
A Behind-the-Scenes Look at How We Use cap tables to Manage Our $500,000M Fund.— People always ask me how we manage our portfolio of 14 companies. The answer is a disciplined system built around cap tables. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
I Lost $250,000 on a Bad Deal. Here's the Brutal Lesson I Learned About secondary markets.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a secondary markets and lost $250,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
Why Your Obsession with term sheets is Actually Killing Your Returns.— Every VC blog tells you to focus on term sheets. I'm here to tell you that's terrible advice. I've seen more startups fail because of a premature obsession with term sheets than almost any other reason. Here's the counterintuitive truth about what you should be focusing on instead.
A Behind-the-Scenes Look at How We Use cap tables to Manage Our $1,000,000M Fund.— People always ask me how we manage our portfolio of 9 companies. The answer is a disciplined system built around cap tables. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
I Lost $250,000 on a Bad Deal. Here's the Brutal Lesson I Learned About portfolio construction.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a portfolio construction and lost $250,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
We Analyzed 5 Deals: This One Clause in the cap tables Separates the Winners from the Losers.— After analyzing our last 5 investments, a surprising pattern emerged. The founders who negotiated this one specific clause in the cap tables consistently outperformed. I'm breaking down the data and showing you the exact language that correlates with a higher chance of success.
Why Your Obsession with rolling funds is Actually Killing Your Returns.— Every VC blog tells you to focus on rolling funds. I'm here to tell you that's terrible advice. I've seen more startups fail because of a premature obsession with rolling funds than almost any other reason. Here's the counterintuitive truth about what you should be focusing on instead.
We Analyzed 11 Deals: This One Clause in the SPVs Separates the Winners from the Losers.— After analyzing our last 11 investments, a surprising pattern emerged. The founders who negotiated this one specific clause in the SPVs consistently outperformed. I'm breaking down the data and showing you the exact language that correlates with a higher chance of success.
We Analyzed 6 Deals: This One Clause in the SPVs Separates the Winners from the Losers.— After analyzing our last 6 investments, a surprising pattern emerged. The founders who negotiated this one specific clause in the SPVs consistently outperformed. I'm breaking down the data and showing you the exact language that correlates with a higher chance of success.
A Behind-the-Scenes Look at How We Use syndicate investing to Manage Our $50,000M Fund.— People always ask me how we manage our portfolio of 13 companies. The answer is a disciplined system built around syndicate investing. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
I Lost $100,000 on a Bad Deal. Here's the Brutal Lesson I Learned About secondary markets.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a secondary markets and lost $100,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
Why syndicate investing Will Be the Most Important Skill for VCs in 2027.— The venture landscape is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of syndicate investing is about to become the single most critical differentiator for successful investors in 2027. Here's why and how to get ahead of the curve.
The Truth About syndicate investing: What Your VC Will Never Tell You.— I've sat on both sides of the table. As a founder, I was often in the dark. As a VC, I learned the unwritten rules of the game. I'm pulling back the curtain on syndicate investing and revealing what investors are really thinking when they send you that document.
Why Your Obsession with rolling funds is Actually Killing Your Returns.— Every VC blog tells you to focus on rolling funds. I'm here to tell you that's terrible advice. I've seen more startups fail because of a premature obsession with rolling funds than almost any other reason. Here's the counterintuitive truth about what you should be focusing on instead.
Why portfolio construction Will Be the Most Important Skill for VCs in 2027.— The venture landscape is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of portfolio construction is about to become the single most critical differentiator for successful investors in 2027. Here's why and how to get ahead of the curve.
How to Structure a syndicate investing (The Counterintuitive Guide for Founders).— Most guides on syndicate investing are written for VCs, not founders. They tell you what to do, but not why, or how to negotiate from a position of strength. This is the guide I wish I had when I was raising my first round—a founder-friendly approach to building a syndicate investing that protects you.
Why Your Obsession with dilution is Actually Killing Your Returns.— Every VC blog tells you to focus on dilution. I'm here to tell you that's terrible advice. I've seen more startups fail because of a premature obsession with dilution than almost any other reason. Here's the counterintuitive truth about what you should be focusing on instead.
A Behind-the-Scenes Look at How We Use term sheets to Manage Our $100,000M Fund.— People always ask me how we manage our portfolio of 4 companies. The answer is a disciplined system built around term sheets. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
Why cap tables Will Be the Most Important Skill for VCs in 2026.— The venture landscape is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of cap tables is about to become the single most critical differentiator for successful investors in 2026. Here's why and how to get ahead of the curve.
What I’ve Learned About Term Sheets: What VCs Don’t Tell Founders— After negotiating term sheets as a founder and later as a VC, I want to give you an insider’s view. I’ll explain the key details investors focus on and how to protect yourself when you get that offer.
How Mastering Term Sheets Will Shape Venture Capital Success in 2027— The venture capital world is evolving fast. From my experience as an entrepreneur and investor, understanding term sheets deeply is going to set top investors apart in 2027. I’ll share why this matters and how you can stay ahead.
How One Clause Made All the Difference in Our Last 10 Investment Deals— From my experience investing in startups, I've noticed a pattern: founders who secure this particular clause tend to outperform others. In this article, I explain the data behind it and share the exact wording that matters.
How Rolling Funds Will Shape Venture Capital in 2026— The venture capital world is evolving fast. From my experience, rolling funds are becoming a crucial tool for investors who want to stay ahead in 2026. I'll share what this means and how you can prepare.
How I Structure Term Sheets to Protect My Startup— Most advice on term sheets misses what founders really need. I’m sharing the practical approach I used to negotiate terms confidently and keep control during fundraising.
My Take: The Truth About follow-on investing: What Your VC Will Never Tell You.— I've sat on both sides of the table. As a founder, I was often in the dark. As a VC, I learned the unwritten rules of the game. I'm pulling back the curtain on follow-on investing and revealing what investors are really thinking when they send you that document.
My Take: The Truth About syndicate investing: What Your VC Will Never Tell You.— I've sat on both sides of the table. As a founder, I was often in the dark. As a VC, I learned the unwritten rules of the game. I'm pulling back the curtain on syndicate investing and revealing what investors are really thinking when they send you that document.
My Take: 6 Things I Learned About rolling funds After Writing Checks for 18 Years.— I've been an angel investor for 18 years, and my understanding of rolling funds has been completely transformed. These aren't the textbook lessons; these are the hard-won insights from the trenches. Here are the 6 most critical things I wish I knew when I started.
My Take: Why portfolio construction Will Be the Most Important Skill for VCs in 2025.— Here's my take on the venture is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of portfolio construction is about to become the single most critical differentiator for successful investors in 2025. Here's why and how to get ahead of the curve.
My Take: Why Your Obsession with secondary markets is Actually Killing Your Returns.— Here's my take on every VC blog tells you to focus on secondary markets. I'm here to tell you that's terrible advice. I've seen more startups fail because of a premature obsession with secondary markets than almost any other reason. Here's the counterintuitive truth about what you should be focusing on instead.
My Take: I Lost $500,000 on a Bad Deal. Here's the Brutal Lesson I Learned About follow-on investing.— Here's my take on before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a follow-on investing and lost $500,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
The Truth About syndicate investing: What Your VC Will Never Tell You.— I've sat on both sides of the table. As a founder, I was often in the dark. As a VC, I learned the unwritten rules of the game. I'm pulling back the curtain on syndicate investing and revealing what investors are really thinking when they send you that document.
Why term sheets Will Be the Most Important Skill for VCs .— The venture is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of term sheets is about to become the single most critical differentiator for successful investors in 2025. Here's why and how to get ahead of the curve.
Why Your Obsession with syndicate investing is Actually Killing Your Returns.— Every VC blog tells you to focus on syndicate investing. I'm here to tell you that's terrible advice. I've seen more startups fail because of a premature obsession with syndicate investing than almost any other reason. Here's the counterintuitive truth about what you should be focusing on instead.
Why dilution Will Be the Most Important Skill for VCs .— The venture is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of dilution is about to become the single most critical differentiator for successful investors in 2027. Here's why and how to get ahead of the curve.
A Behind-the-Scenes Look at How We Use rolling funds to Manage Our $1,000,000M Fund.— People always ask me how we manage our portfolio of 5 companies. The answer is a disciplined system built around rolling funds. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
11 Things I Learned About rolling funds After Writing Checks for 17 Years.— I've been an angel investor for 17 years, and my understanding of rolling funds has been completely transformed. These aren't the textbook lessons; these are the hard-won insights from the trenches. Here are the 11 most critical things I wish I knew when I started.
The Truth About follow-on investing: What Your VC Will Never Tell You.— I've sat on both sides of the table. As a founder, I was often in the dark. As a VC, I learned the unwritten rules of the game. I'm pulling back the curtain on follow-on investing and revealing what investors are really thinking when they send you that document.
Why portfolio construction Will Be the Most Important Skill for VCs in 2025.— The venture landscape is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of portfolio construction is about to become the single most critical differentiator for successful investors in 2025. Here's why and how to get ahead of the curve.
A Behind-the-Scenes Look at How We Use dilution to Manage Our $500,000M Fund.— People always ask me how we manage our portfolio of 13 companies. The answer is a disciplined system built around dilution. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
Why Your Obsession with rolling funds is Actually Killing Your Returns.— Every VC blog tells you to focus on rolling funds. I'm here to tell you that's terrible advice. I've seen more startups fail because of a premature obsession with rolling funds than almost any other reason. Here's the counterintuitive truth about what you should be focusing on instead.
12 Things I Learned About portfolio construction After Writing Checks for 15 Years.— I've been an angel investor for 15 years, and my understanding of portfolio construction has been completely transformed. These aren't the textbook lessons; these are the hard-won insights from the trenches. Here are the 12 most critical things I wish I knew when I started.
I Lost $250,000 on a Bad Deal. Here's the Brutal Lesson I Learned About follow-on investing.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a follow-on investing and lost $250,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
How to Structure a dilution (The Counterintuitive Guide for Founders).— Most guides on dilution are written for VCs, not founders. They tell you what to do, but not why, or how to negotiate from a position of strength. This is the guide I wish I had when I was raising my first round—a founder-friendly approach to building a dilution that protects you.
Why SPVs Will Be the Most Important Skill for VCs in 2027.— The venture landscape is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of SPVs is about to become the single most critical differentiator for successful investors in 2027. Here's why and how to get ahead of the curve.
I Lost $250,000 on a Bad Deal. Here's the Brutal Lesson I Learned About term sheets— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a term sheets and lost $250,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
A Behind-the-Scenes Look at How We Use portfolio construction to Manage Our $500,000M Fund— People always ask me how we manage our portfolio of 11 companies. The answer is a disciplined system built around portfolio construction. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
4 Things I Learned About SPVs After Writing Checks for 5 Years— I've been an angel investor for 5 years, and my understanding of SPVs has been completely transformed. These aren't the textbook lessons; these are the hard-won insights from the trenches. Here are the 4 most critical things I wish I knew when I started.
Why secondary markets Will Be the Most Important Skill for VCs in 2025— The venture landscape is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of secondary markets is about to become the single most critical differentiator for successful investors in 2025. Here's why and how to get ahead of the curve.
A Behind-the-Scenes Look at How We Use term sheets to Manage Our $250,000M Fund— People always ask me how we manage our portfolio of 14 companies. The answer is a disciplined system built around term sheets. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
A Behind-the-Scenes Look at How We Use follow-on investing to Manage Our $500,000M Fund— People always ask me how we manage our portfolio of 15 companies. The answer is a disciplined system built around follow-on investing. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
I Lost $100,000 on a Bad Deal. Here's the Brutal Lesson I Learned About follow-on investing— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a follow-on investing and lost $100,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
Why Your Obsession with rolling funds is Actually Killing Your Returns.— Every VC blog tells you to focus on rolling funds. I'm here to tell you that's terrible advice. I've seen more startups fail because of a premature obsession with rolling funds than almost any other reason. Here's the counterintuitive truth about what you should be focusing on instead.
Why SPVs Will Be the Most Important Skill for VCs in 2027.— The venture landscape is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of SPVs is about to become the single most critical differentiator for successful investors in 2027. Here's why and how to get ahead of the curve.
Why dilution Will Be the Most Important Skill for VCs in 2027.— The venture landscape is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of dilution is about to become the single most critical differentiator for successful investors in 2027. Here's why and how to get ahead of the curve.
How to Structure a portfolio construction (The Counterintuitive Guide for Founders).— Most guides on portfolio construction are written for VCs, not founders. They tell you what to do, but not why, or how to negotiate from a position of strength. This is the guide I wish I had when I was raising my first round—a founder-friendly approach to building a portfolio construction that protects you.
I Lost $100,000 on a Bad Deal. Here's the Brutal Lesson I Learned About syndicate investing.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a syndicate investing and lost $100,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
I Lost $500,000 on a Bad Deal. Here's the Brutal Lesson I Learned About rolling funds.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a rolling funds and lost $500,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
What I Wish Founders Knew About Follow-On Investing— Having been both a founder and a VC, I know firsthand how confusing follow-on investing can be. I’m here to share the behind-the-scenes truths and what investors are really thinking when they offer you that deal.
Why I Believe Rolling Funds Will Matter Most for VCs in 2027— Things are changing fast in venture capital. The old methods won’t work much longer. From what I’m seeing, understanding rolling funds will set successful investors apart in 2027. Let me explain why and how you can get ahead.
I Lost $1,000,000 on a Follow-On Investment and Here’s What I Learned— Before hitting a big win, I made a costly mistake in follow-on investing that lost me $1,000,000. I’m sharing the full story so you can avoid making the same error. This was a tough lesson that changed how I approach venture investing.
I Lost $1,000,000 on a Bad Deal. Here's the Brutal Lesson I Learned About term sheets.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a term sheets and lost $1,000,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
A Behind-the-Scenes Look at How We Use SPVs to Manage Our $500,000M Fund.— People always ask me how we manage our portfolio of 7 companies. The answer is a disciplined system built around SPVs. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
How to Structure a cap tables (The Counterintuitive Guide for Founders).— Most guides on cap tables are written for VCs, not founders. They tell you what to do, but not why, or how to negotiate from a position of strength. This is the guide I wish I had when I was raising my first round—a founder-friendly approach to building a cap tables that protects you.
I Lost $50k on a Bad Deal— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a portfolio construction and lost $50,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
I Lost $50k on a Bad Deal— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a portfolio construction and lost $50,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
Why Your Obsession with term sheets is Actually Killing Your Returns.— Every VC blog tells you to focus on term sheets. I'm here to tell you that's terrible advice. I've seen more startups fail because of a premature obsession with term sheets than almost any other reason. Here's the counterintuitive truth about what you should be focusing on instead.
The Truth About follow-on investing: What Your VC Will Never Tell You.— I've sat on both sides of the table. As a founder, I was often in the dark. As a VC, I learned the unwritten rules of the game. I'm pulling back the curtain on follow-on investing and revealing what investors are really thinking when they send you that document.
3 Things I Learned About follow-on investing After Writing Checks for 5 Years.— I've been an angel investor for 5 years, and my understanding of follow-on investing has been completely transformed. These aren't the textbook lessons; these are the hard-won insights from the trenches. Here are the 3 most critical things I wish I knew when I started.
14 Things I Learned About syndicate investing After Writing Checks for 6 Years.— I've been an angel investor for 6 years, and my understanding of syndicate investing has been completely transformed. These aren't the textbook lessons; these are the hard-won insights from the trenches. Here are the 14 most critical things I wish I knew when I started.
14 Things I Learned About term sheets After Writing Checks for 18 Years.— I've been an angel investor for 18 years, and my understanding of term sheets has been completely transformed. These aren't the textbook lessons; these are the hard-won insights from the trenches. Here are the 14 most critical things I wish I knew when I started.
How I Use Follow-On Investing to Manage Our $1 Billion Fund— People often ask how I manage investments across 12 companies. I rely on a straightforward follow-on investing system that keeps everything on track. Here’s a candid look at the process, tools, and templates I use every day.
My Take: 9 Things I Learned About dilution After Writing Checks for 14 Years.— I've been an angel investor for 14 years, and my understanding of dilution has been completely transformed. These aren't the textbook lessons; these are the hard-won insights from the trenches. Here are the 9 most critical things I wish I knew when I started.
My Take: A Behind-the-Scenes Look at How We Use SPVs to Manage Our $500,000M Fund.— Here's my take on people always ask me how we manage our portfolio of 7 companies. The answer is a disciplined system built around SPVs. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
How I Structure a rolling funds (The Counterintuitive Guide for Founders).— Here's my take on most guides on rolling funds are written for VCs, not founders. They tell you what to do, but not why, or how to negotiate from a position of strength. This is the guide I wish I had when I was raising my first round-a founder-friendly approach to building a rolling funds that protects you.
14 Things I Learned About secondary markets After Writing Checks for 11 Years.— I've been an angel investor for 11 years, and my understanding of secondary markets has been completely transformed. These aren't the textbook lessons; these are the hard-won insights from the trenches. Here are the 14 most critical things I wish I knew when I started.
Structure a cap tables (The Counterintuitive Guide for Founders).— Most guides on cap tables are written for VCs, not founders. They tell you what to do, but not why, or how to negotiate from a position of strength. This is the guide I wish I had when I was raising my first round-a founder-friendly approach to building a cap tables that protects you.
Why cap tables Will Be the Most Important Skill for VCs in 2027.— The venture landscape is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of cap tables is about to become the single most critical differentiator for successful investors in 2027. Here's why and how to get ahead of the curve.
13 Things I Learned About dilution After Writing Checks for 19 Years.— I've been an angel investor for 19 years, and my understanding of dilution has been completely transformed. These aren't the textbook lessons; these are the hard-won insights from the trenches. Here are the 13 most critical things I wish I knew when I started.
The Truth About syndicate investing: What Your VC Will Never Tell You.— I've sat on both sides of the table. As a founder, I was often in the dark. As a VC, I learned the unwritten rules of the game. I'm pulling back the curtain on syndicate investing and revealing what investors are really thinking when they send you that document.
I Lost $250,000 on a SPV Mistake and What I Learned— I made a big mistake early on that cost me $250,000. I’m sharing what happened so you don’t have to go through the same pain. It was a tough lesson, but it taught me what really matters in investing.
I Lost $50,000 on a Bad Deal. Here's the Brutal Lesson I Learned About rolling funds.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a rolling funds and lost $50,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
I Lost $500,000 on a Bad Deal. Here's the Brutal Lesson I Learned About secondary markets.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a secondary markets and lost $500,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
15 Things I Learned About syndicate investing After Writing Checks for 18 Years.— I've been an angel investor for 18 years, and my understanding of syndicate investing has been completely transformed. These aren't the textbook lessons; these are the hard-won insights from the trenches. Here are the 15 most critical things I wish I knew when I started.
7 Things I Learned About SPVs After Writing Checks for 9 Years.— I've been an angel investor for 9 years, and my understanding of SPVs has been completely transformed. These aren't the textbook lessons; these are the hard-won insights from the trenches. Here are the 7 most critical things I wish I knew when I started.
A Behind-the-Scenes Look at How We Use SPVs to Manage Our $100,000M Fund.— People always ask me how we manage our portfolio of 15 companies. The answer is a disciplined system built around SPVs. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
I Lost $100,000 on a Bad Deal. Here's the Brutal Lesson I Learned About dilution.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a dilution and lost $100,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
Why Being Obsessed with Term Sheets Hurt My Returns— Most people say you should focus on term sheets. From my experience, that's not the best approach. I've seen startups stumble because of this obsession. Here's what really matters when you're investing.
I Lost $500,000 on a Bad Deal. Here's What I Learned.— Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a portfolio construction and lost $500,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.