Disrupting disruption with disruptive disruptions since 2010.
The VC firm that sets the terms and does the heavy lifting in a funding round, while other investors gratefully follow along. Someone has to negotiate while everyone else free-rides.
A calculation of ownership percentages that includes all possible shares—options, warrants, convertible notes, and that napkin the founder signed in 2009. The number that reveals how little of the company you actually own.
The mathematical reality that in venture capital, one or two investments generate nearly all the returns while the rest are mediocre or dead. Why VCs can lose money on 90% of their portfolio and still return 3x the fund.
Company valuation after investment capital is added, the number founders brag about while carefully omitting the 'post-money' qualifier. What your company is theoretically worth with someone else's money included.
The privilege granted to preferred shareholders to convert their fancy preferred stock into common stock, typically exercised when they want to sell or when common stock becomes more valuable (rare but delightful). It's a one-way ticket that investors usually only take when they're confident they're not leaving money on the table.
The maximum valuation at which a convertible note or SAFE will convert to equity—a safety net for early investors betting on you when you were nobody. The lower the cap, the more expensive your desperation was.
The delicate art of figuring out how to extract money from something that users currently enjoy for free, typically resulting in a barrage of ads, paywalls, or premium subscriptions. This verb represents the moment when platforms transition from "community-building" to "shareholder-pleasing," often coinciding with users complaining that everything good gets ruined. Monetization strategies range from subtle to obnoxious, but they all share the goal of turning engagement into revenue.
A provision allowing limited partners to reclaim previously distributed carried interest from GPs if later losses reduce overall fund returns. The nightmare scenario keeping fund managers up at night.
When VCs make investment decisions based on superficial similarities to previous successful startups rather than rigorous analysis. It's why they love Stanford dropouts building social apps in their dorm rooms.
Late-stage debt or hybrid securities used to bridge the gap between venture rounds and an exit. It's called mezzanine because it sits between the ground floor (equity) and penthouse (IPO).
An entrepreneur who returns to start another company after their previous venture was acquired or failed. They're either gluttons for punishment or genuinely addicted to the startup lifestyle.
The right to participate in future financing rounds to maintain ownership percentage, preventing dilution through passive-aggressive legal provisions. Pro rata rights by another name, somehow more intimidating.
The exhaustion investors feel after reviewing hundreds of pitch decks that all blur together with the same buzzwords and hockey stick projections. It's why your 'revolutionary AI blockchain solution' makes their eyes glaze over.
A startup that returns an entire venture fund's value through a single investment, making every other deal in the portfolio irrelevant. Rarer than unicorns and more impactful than a hundred modest successes combined.
A financing or exit event that triggers specific contractual provisions in a term sheet, such as conversion of convertible notes or acceleration of vesting. The legal trip-wire that determines when various startup agreements activate.
When a startup raises funding from institutional VCs after initially bootstrapping or taking only angel money. It's like moving from community college to the Ivy League, complete with higher expectations.
The cultural expectation in startup ecosystems that successful entrepreneurs and investors should help newcomers, supposedly creating a virtuous cycle. In practice, it's often networking disguised as altruism.
The company valuation publicly announced or reported in the press, which may differ from the effective valuation once liquidation preferences and other terms are factored in. It's the Instagram filter for startup valuations.
A supplemental investment vehicle created alongside a main fund to accommodate additional capital from LPs or special investors, often for a specific deal or opportunity too large for the main fund. The VC version of ordering extra fries because one serving isn't enough.
When a VC aggressively increases their investment in a portfolio company across multiple rounds, betting their career on being right. Conviction investing taken to its logical extreme.
The overwhelming wave of convertible notes and SAFEs that convert to equity during a priced round, often revealing a far more complex cap table than founders realized. The moment when chickens come home to roost, except the chickens are financial instruments.
Legal promises in investment agreements where founders swear everything they've said is true and the company isn't hiding skeletons. Breaking these can result in personal liability, making due diligence the most stressful time to discover that intern you hired in 2019 never signed an IP assignment.
The magical moment when stock options or retirement contributions officially become yours to keep, transforming from corporate dangling carrot into actual ownership. It's the golden handcuffs' lock clicking shut, ensuring you'll think twice before rage-quitting. The startup world's version of 'you must be this loyal to ride this rocket ship.'
A group of users who started in the same time period, tracked to see how many stick around. The cruel truth about how fast people abandon your product.