Venture Capital Deep Dives
VC fund mechanics, market analysis, investment thesis development, LP relations
VCs, LPs, founders understanding VC dynamics, aspiring investors
Fund performance, deal sourcing, portfolio management, market timing
Featured in Venture Capital Deep Dives
The Truth About syndicate investing: What Your VC Will Never Tell You.
Syndicate investing from the investor's side: how leads pick deals, what backers look for, and the unwritten rules founders should know before saying yes.
A Costly Lesson About Follow-On Investing
Misreading follow-on investing is one of the most expensive rookie mistakes in angel investing: what goes wrong, the warning signs, and how to avoid it.
A Costly Lesson About Portfolio Construction
Misreading portfolio construction is one of the most expensive rookie mistakes in angel investing: what goes wrong, the warning signs, and how to avoid it.
A Costly Lesson About Cap Tables
Misreading cap tables is one of the most expensive rookie mistakes in angel investing: what goes wrong, the warning signs, and how to avoid it.
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.
A Costly Lesson About Follow-On Investing
Misreading follow-on investing is one of the most expensive rookie mistakes in angel investing: what goes wrong, the warning signs, and how to avoid it.
The Truth About SPVs: What Your VC Will Never Tell You.
How SPVs work from the investor's side: fees, carry, minimums, and the unwritten rules founders rarely hear before an SPV joins their cap table.
Using Cap Tables to Manage a Portfolio
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.
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 Costly Lesson About Dilution
Misreading dilution is one of the most expensive rookie mistakes in angel investing: what goes wrong, the warning signs, and how to avoid it.
The Truth About cap tables: What Your VC Will Never Tell You.
How investors read your cap table: the dilution, option pool and ownership signals they check, and what founders should fix before the first meeting.
A Costly Lesson About Rolling Funds
Misreading rolling funds is one of the most expensive rookie mistakes in angel investing: what goes wrong, the warning signs, and how to avoid it.
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.
A Costly Lesson About Follow-On Investing
Misreading follow-on investing is one of the most expensive rookie mistakes in angel investing: what goes wrong, the warning signs, and how to avoid it.
The Truth About follow-on investing: What Your VC Will Never Tell You.
Follow-on investing from the investor's side: how reserves are set, which signals earn a second check, and what founders should ask existing backers.
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.
Follow-on investing from the investor's side: how reserves are set, which signals earn a second check, and what founders should ask existing backers.
The Truth About follow-on investing: What Your VC Will Never Tell You.
Follow-on investing from the investor's side: how reserves are set, which signals earn a second check, and what founders should ask existing backers.
A Costly Lesson About Secondary Markets
Misreading secondary markets is one of the most expensive rookie mistakes in angel investing: what goes wrong, the warning signs, and how to avoid it.
The Truth About secondary markets: What Your VC Will Never Tell You.
How secondary markets work from the investor's side: pricing, transfer rules, and what buyers weigh before making founders and early employees an offer.
Term Sheets: The One Clause That Matters
After analyzing our last 14 investments, a surprising pattern emerged. The founders who negotiated this one specific clause in the term sheets consistently outperformed. I'm breaking down the data and showing you the exact language that correlates with a higher chance of success.
SPVs: The One Clause That Matters
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.
Secondary Markets: The Clause That Matters
After analyzing our last 6 investments, a surprising pattern emerged. The founders who negotiated this one specific clause in the secondary markets consistently outperformed. I'm breaking down the data and showing you the exact language that correlates with a higher chance of success.
- Cap Table Discipline for Portfolio Managers
- A Costly Lesson About Secondary Markets
- Why Your Obsession with term sheets is Actually Killing Your Returns.
- Cap Tables for Fund Managers, Explained
- 15 Things I Learned About syndicate investing After Writing Checks for 18 Years.
- A Costly Lesson About Portfolio Construction
- 3 Things I Learned About follow-on investing After Writing Checks for 5 Years.
- Cap Tables: The One Clause That Matters
- Why Your Obsession with rolling funds is Actually Killing Your Returns.
- SPVs: The One Clause That Matters
- SPVs: The One Clause That Matters
- 14 Things I Learned About syndicate investing After Writing Checks for 6 Years.
- 7 Things I Learned About SPVs After Writing Checks for 9 Years.
- Using Syndicates to Manage a Portfolio
- A Costly Lesson About Secondary Markets
- Why syndicate investing Will Be the Most Important Skill for VCs in 2027.
- The Truth About syndicate investing: What Your VC Will Never Tell You.
- Why Your Obsession with rolling funds is Actually Killing Your Returns.
- 14 Things I Learned About term sheets After Writing Checks for 18 Years.
- Why portfolio construction Will Be the Most Important Skill for VCs in 2027.
- How to Structure a syndicate investing (The Counterintuitive Guide for Founders).
- Why Your Obsession with dilution is Actually Killing Your Returns.
- How SPVs Help Investors Manage a Portfolio
- Using Term Sheets to Manage a Portfolio
- A Costly Lesson About Dilution
- Why cap tables Will Be the Most Important Skill for VCs in 2026.
- What I’ve Learned About Term Sheets: What VCs Don’t Tell Founders
- A Costly Lesson About Secondary Markets
- How Mastering Term Sheets Will Shape Venture Capital Success in 2027
- How One Clause Made All the Difference in Our Last 10 Investment Deals
- How Rolling Funds Will Shape Venture Capital in 2026
- Follow-On Investing: A System That Works
- How I Structure Term Sheets to Protect My Startup
- A Costly Lesson About Portfolio Construction
- My Take: 9 Things I Learned About dilution After Writing Checks for 14 Years.
- SPVs and Portfolio Management, Explained
- My Take: The Truth About follow-on investing: What Your VC Will Never Tell You.
- My Take: The Truth About syndicate investing: What Your VC Will Never Tell You.
- My Take: 6 Things I Learned About rolling funds After Writing Checks for 18 Years.
- My Take: Why portfolio construction Will Be the Most Important Skill for VCs in 2025.
- How to Structure a Rolling Fund
- My Take: Why Your Obsession with secondary markets is Actually Killing Your Returns.
- A Costly Lesson About Follow-On Investing
- The Truth About syndicate investing: What Your VC Will Never Tell You.
- 14 Things I Learned About secondary markets After Writing Checks for 11 Years.
- Why term sheets Will Be the Most Important Skill for VCs .
- Why Your Obsession with syndicate investing is Actually Killing Your Returns.
- Why dilution Will Be the Most Important Skill for VCs .
- How Rolling Funds Are Managed Day to Day
- 11 Things I Learned About rolling funds After Writing Checks for 17 Years.
- The Truth About follow-on investing: What Your VC Will Never Tell You.
- Structure a cap tables (The Counterintuitive Guide for Founders).
- Why portfolio construction Will Be the Most Important Skill for VCs in 2025.
- Syndicate Investing: The Clause That Matters
- How Investors Manage Dilution in a Portfolio
- Why cap tables Will Be the Most Important Skill for VCs in 2027.
- Why Your Obsession with rolling funds is Actually Killing Your Returns.
- 12 Things I Learned About portfolio construction After Writing Checks for 15 Years.
- A Costly Lesson About Follow-On Investing
- How to Structure a dilution (The Counterintuitive Guide for Founders).
- Why SPVs Will Be the Most Important Skill for VCs in 2027.
- A Costly Lesson About Term Sheets
- Portfolio Construction: A Working System
- 4 Things I Learned About SPVs After Writing Checks for 5 Years
- Why secondary markets Will Be the Most Important Skill for VCs in 2025
- Term Sheets as a Portfolio Management Tool
- How Investors Decide on Follow-On Checks
- A Costly Lesson About Follow-On Investing
- 13 Things I Learned About dilution After Writing Checks for 19 Years.
- Why Your Obsession with rolling funds is Actually Killing Your Returns.
- Cap Tables: The One Clause That Matters
- The Truth About syndicate investing: What Your VC Will Never Tell You.
- Why SPVs Will Be the Most Important Skill for VCs in 2027.
- Why dilution Will Be the Most Important Skill for VCs in 2027.
- How to Structure a portfolio construction (The Counterintuitive Guide for Founders).
- A Costly Lesson About Rolling Funds
- A Costly Lesson About Syndicate Investing
- Why Being Obsessed with Term Sheets Hurt My Returns
- A Costly Lesson About SPVs
- What I Wish Founders Knew About Follow-On Investing
- Why I Believe Rolling Funds Will Matter Most for VCs in 2027
- A Costly Lesson About Follow-On Investing
- A Costly Lesson About Portfolio Construction
- Rolling Funds: The One Clause That Matters
- A System for Portfolio Construction
- A Costly Lesson About Term Sheets
- How to Structure a cap tables (The Counterintuitive Guide for Founders).
- Using SPVs to Manage an Investment Portfolio
- How Angels Lose Money on Bad Deals
- How Angels Lose Money on Bad Deals