Pinion Blog
Insights for angel investors
Guides, product updates, and thinking on portfolio management.
Pinion Is Now on Capterra — Would You Leave Us a Review?
Pinion is now listed on Capterra. If you've been using it to track your angel portfolio, we'd love a quick review.
Read more →Why I Love Pivots (The Counterpoint)
A pivot is sometimes the best thing that can happen to an early-stage investment. The founders I most want to back are precisely the ones willing to do it.
Read more →Why I Hate Pivots
I know. Pivots are a normal part of building a startup, but I still hate them. Every time I see that email announcing the great news, I have the same reaction: Ugh. Here's why.
Read more →How Much of Your Portfolio Should Be Angel Investments?
There's no clean number — but there's a useful framework for thinking about how much of your net worth should be in angel deals, including a structural trap that catches most entrepreneurs and family offices off guard.
Read more →When Your Numbers Don't Match: How Dilution Quietly Changes Your Investment
The headline markup on a new round is not the same as your position-level markup. Here's how dilution works, why your tracker and the angel club often disagree, and what to do about it.
Read more →Three Questions I Ask Myself in the First Meeting
What do I look for at the seed stage? Three questions: do I understand the business, do I believe the founders will fight through brick walls, and can this 100x my money?
Read more →Why Angel Clubs Are the Best Way to Start
Angel clubs offer more than deal flow — they teach you how experienced angels think. After eight-plus years in Alamo Angels, here’s what we’ve learned that we couldn’t have figured out on our own.
Read more →DPI vs. TVPI: Paper Gains and Real Money
TVPI tells you what the investment is worth on paper. DPI tells you what's actually been returned. Understanding what each metric measures—and what the gap between them implies—is one of the more practical skills in evaluating private investment performance.
Read more →QSBS: The Asymmetric Tax Play Underlying Angel Investing
Section 1202 can make your gains tax-free. Section 1244 can make your losses deductible against ordinary income. Together, they create one of the most asymmetric risk profiles in U.S. investing — but only if you plan for both before you write the check.
Read more →The Art of Reading Investor Updates
Most angels read investor updates looking for reassurance. That's the wrong goal. This piece walks through how to read updates as information — what to look past, what to look for, how to revisit your original thesis, and how to recognize when a polite update is quietly telling you something is wrong.
Read more →Talk to Your Portfolio: Getting the Pinion MCP Up and Running
Connect Pinion to Claude, Cursor, or any MCP-compatible AI assistant and ask questions about your portfolio in plain English. This guide covers setup for every major client plus the workflows and prompts that make it genuinely useful.
Read more →MOIC vs. TVPI: What They Measure, Why They Differ, and How to Read Them
MOIC and TVPI are often used interchangeably, but they answer slightly different questions. This piece explains what each metric measures, when to use which, and how to read the patterns they reveal in your portfolio.
Read more →The Power Law and the Case for Following Your Winners
Angel returns aren't normally distributed — a handful of investments generate most of the gains. Understanding the power law changes how you think about diversification, follow-on investing, and the single highest-leverage decision most angels never make deliberately.
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