Retention is a critical signal of product-market fit and long-term growth potential. Metrics like net dollar retention, gross dollar retention, LTV/CAC, CAC payback, and DAU/MAU help quantify how well a startup holds and grows its customer base. Cohort analysis adds depth by showing how user behaviour changes over time and across segments. Together, these tools help founders and investors understand the true durability of a business.

OpenAI’s $40B raise at a $300B valuation, led by SoftBank and Microsoft, marks the largest private tech deal ever and cements AI as foundational infrastructure. The capital will fuel massive compute expansion via the Stargate JV and scale enterprise adoption of ChatGPT. While institutional investors are all-in, SoftBank’s stock drop reflects concerns over execution and capital intensity.

CoreWeave’s $27B valuation hinges on a fragile GPU arbitrage model propped up by debt, with 62% of revenue coming from Microsoft, a customer likely to walk once its own infrastructure scales. Without diversified demand, better margins, and stronger financial controls, CoreWeave looks more like a well-financed stopgap than a sustainable AI infrastructure giant.

Wiz’s $32 billion acquisition by Google marks one of the largest venture-backed deals in history—but just a year ago, they turned down a $23 billion offer. Their decision to hold out reflects a broader resurgence in tech M&A, signalling renewed investor confidence and a shifting regulatory landscape.

Venture debt offers startups non-dilutive capital while providing lenders high-yield returns based on future equity raises rather than historical cash flow. With structured 4-year loans, interest income as the primary return, and high-yield seniority, it’s a strategic, asymmetric play in the venture ecosystem for lenders.

Venture debt is a flexible, low-dilution funding option for VC-backed startups, typically used alongside equity to extend runway without giving up more ownership. It’s repaid through future equity raises, not cash flow, and works best right after a funding round when momentum is strong and capital needs are high.

TVPI measures a fund’s total value, including unrealized gains, while DPI shows actual cash returned to investors—making DPI the more reliable indicator of true performance. TVPI can signal potential upside, but DPI is the ultimate proof that a fund has delivered real returns to LPs.

In venture, a fund’s “vintage year” marks when it starts investing—and performance varies widely by era. While late ’90s and post-2008 vintages delivered standout returns, recent vintages (2020–2021) face headwinds, highlighting how market timing and disciplined investing shape long-term outcomes.

Carried interest is taxed as long-term capital gains (max 20%) instead of ordinary income (up to 37%), a major tax break for GPs that's repeatedly come under political fire. Despite years of reform attempts, including efforts in 2017 and 2022, the loophole remains—and the debate over its future is far from over.

Carried interest is the share of a fund’s profits GPs earn—typically 20%—but only after LPs are repaid and a minimum return (the hurdle rate) is met. It’s paid through a structured waterfall and varies by fund model, making it a high-reward but performance-dependent incentive for venture fund managers.

In venture capital, returning a fund isn’t enough—LPs expect outsized returns to justify the high risk. Due to high failure rates and dilution, only a massive outlier (100x+) can make the math work, making power-law outcomes essential for top-tier fund performance.

Venture capital thrives in low-rate environments, but rising interest rates and strong public equity returns have made VC less attractive on a risk-adjusted basis. If high rates persist, LPs may shift capital away from VC—unless macro conditions or tech growth swing the pendulum back.