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
What Is AngelList? The Platform That Democratized VC (And the Returns Problem Nobody Talks About)
What Is AngelList? The Platform That Democratized VC (And the Returns Problem Nobody Talks About) AngelList manages $171 billion in assets across more than 25,000 funds and syndicates. The median SPV return on that...
May 27, 2026
SAFE Notes vs Convertible Notes: One Protects Founders, One Protects Investors — Know Which Is Which
SAFE Notes vs Convertible Notes: One Protects Founders, One Protects Investors — Know Which Is Which Y Combinator created the SAFE in 2013 to make fundraising faster. It worked. It also shifted ALL the downside risk to...
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
Startup Funding Rounds Explained: Pre-Seed to Series C in Specific Numbers (Not Theory)
Startup Funding Rounds Explained: Pre-Seed to Series C in Specific Numbers (Not Theory) Only 24 to 27 percent of seed-funded startups ever raise a Series A. The funding ladder gets presented like a staircase every...
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
L Catterton: The $40B Consumer PE Firm With LVMH's Playbook (And Its Blind Spots)
L Catterton: The $40B Consumer PE Firm With LVMH's Playbook (And Its Blind Spots) L Catterton sold Everlane to Shein in May 2026. A sustainable fashion brand built on radical transparency — sold to the company...
May 27, 2026