Common Stock vs Preferred Stock: What Every Angel Investor Must Know Before Writing a Check
Imagine a startup you backed at $2M post-money raises a Series B, sells two years later for $15M, and you walk away with less than what you put in. Not because the company failed. Because you didn’t understand the...
May 27, 2026
Angel Investing in 2026: What the Data Actually Says
Angel Investing in 2026: What the Data Actually Says Seven percent of angel exits produce 75% of all the money made. That one statistic, from a landmark study of 1,137 exits conducted with support from the Angel Capital...
May 27, 2026
Convertible Notes: What Angel Investors Must Know Before They Sign
I watched a $250,000 angel check evaporate in 2019 because the investor never read the maturity clause on a convertible note . The company missed its Series A, the 18-month clock ran out, and that investor spent six...
May 27, 2026
Fund of Funds Explained: When Double Fees Make Sense (And When They Don't)
Put $1 million into a typical private equity fund charging 2% management fees and 20% carried interest. That fund then invests through a fund of funds structure that charges another 1% management fee and 10% carry on...
May 27, 2026
ROFR (Right of First Refusal): What It Means, When It Protects You, and When It Costs You
In 2008, craigslist co-founders Jim Buckmaster and Craig Newmark tried to use a right of first refusal to dilute eBay’s 28.4% stake in their company. The mechanics were creative: offer new shares to anyone who...
May 27, 2026
Advisory Shares: What Every Startup Advisor Should Know Before Signing
A founder called me last year. She had given 2% of her company to a "strategic advisor" who showed up to three Zoom calls and then disappeared. No deliverables. No introductions. No accountability. Just 2% of her cap...
May 27, 2026
SPV Meaning: What a Special Purpose Vehicle Is and How Angel Investors Actually Use One
I watched a $500K SPV close in 72 hours on a Series A that went on to a $180M acquisition. That same structure, used carelessly, has cost investors I know their entire principal. SPV meaning is simple on paper. Special...
May 27, 2026
TVPI Tells You What a Fund Is Worth. It Doesn't Tell You What You'll Get Paid.
A 2019-vintage fund that was showing 3.2x TVPI in early 2022 looked brilliant. By mid-2023, that same fund was sitting at 1.4x. Not a single company had been sold. The GP hadn't made a bad decision in those 18 months....
May 27, 2026
Common Stock vs Preferred Stock: The Liquidation Waterfall That Wipes Out Founders (With Real Math)
Common Stock vs Preferred Stock: The Liquidation Waterfall That Wipes Out Founders (With Real Math) A founder I know owned 45% of his company on paper. The acquirer paid $25 million — exactly what investors had put in...
May 27, 2026
Advisory Shares: Why 90% of Them Are Worth Nothing (And When to Take the Deal)
Advisory Shares: Why 90% of Them Are Worth Nothing (And When to Take the Deal) Run the math. A pre-seed advisory grant of 0.225% equity, at a startup with a 15% chance of surviving, sold at a 6x exit multiple on a $1M...
May 27, 2026
Seed Funding in 2026: How Much to Raise, What to Give Up, and Who Actually Writes the Check
Seed Funding in 2026: How Much to Raise, What to Give Up, and Who Actually Writes the Check Median seed round in 2026: $3–5M at $10–15M pre-money. That sounds like a healthy market until you look at what happens next....
May 27, 2026
Fund of Funds: You're Paying 2-and-20 Twice (Here's When It's Still Worth It)
Fund of Funds: You're Paying 2-and-20 Twice (Here's When It's Still Worth It) Put $1 million into a fund of funds and watch a 3.0x gross multiple shrink to 2.3x net over ten years. That's roughly $700,000 in fee drag on...
May 27, 2026