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VP Engineering

VP Engineering

The VP of Engineering (VP-E) is the senior executive responsible for engineering organization leadership, team management, delivery operations, and engineering culture. Sometimes called Head of Engineering, Director of Engineering, or Engineering Manager at smaller scale. The VP-E owns performance management, hiring and onboarding for engineering roles, and ensuring the engineering team delivers product effectively against business requirements. The role typically becomes necessary when the engineering team grows past 8-15 engineers and a single technical leader (often the founder CTO) can no longer effectively manage all engineering people-management responsibilities while also doing technical leadership work. It is the oper...



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Runway

Runway

Runway is the number of months a startup can operate before running out of cash, calculated as cash on hand divided by monthly net burn. Founders track it monthly (or weekly when cash gets tight), and it is the single most-watched financial metric at an early-stage startup. It is the calendar that determines every other decision: when to raise, when to hire, when to cut, when to push, when to pivot. Running out of runway is the proximate cause behind most stories in [Why Startups Fail].

The math:

Runway (months) = Cash on hand ÷ Monthly net burn

A company with $2M in the bank and $100K/month net burn has 20 months of runway. The same company at $200K/month net burn has 10 months. Doubling burn halves the calendar.

Use net burn (cash ...



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Growth Hacking

Growth Hacking

Growth hacking is the experimental discipline of using non-obvious, leverage-driven tactics to drive rapid user or revenue growth, coined by Sean Ellis in 2010. It combines marketing, product, engineering, and data, often by exploiting existing platforms, distribution loops, or product mechanics rather than by spending on traditional advertising. It is the experimental, scrappy ancestor of modern growth marketing, and the term has been so over-claimed that the original meaning is nearly buried.

The canonical historical examples define what growth hacking actually was. Hotmail appended "PS: I love you. Get your free email at Hotmail" to every outgoing message in 1996 and went from zero to 12 million users in 18 months. Airbnb ...



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GPU Cost

GPU Cost

GPU cost is the underlying compute cost of training and running AI models, dominated by Nvidia's H100, H200, B200, and B300 chips at $25,000-$50,000 each. GPU availability and cost are the limiting factor for AI training because foundation model labs need thousands of GPUs running together in clusters. The GPU supply chain is the single largest infrastructure story of the 2020s tech boom. Behind every AI capability is a stack of expensive GPUs running hot.

The Nvidia GPU lineup (mid-2026):

GPU Launch Approximate price Use case
A100 2020 $10K-$15K Legacy AI workloads
H100 2022 $25K-$40K Mainstream LLM training/inference
H200 2024 $30K-$50K Improved memory for large models
B100/B200 2024-2025 $40K-$60K Next-gen Blackwell...


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Marketing Automation

Marketing Automation

Marketing automation is the use of software platforms to execute, schedule, and measure marketing tasks across email, SMS, web, push, and ad channels. Tasks are based on customer behavior, attributes, and lifecycle stage, with the goal of delivering the right message at the right time to the right person without requiring manual effort per send. It is the engine layer beneath drip campaigns, lifecycle marketing, lead scoring, and most modern email and CRM workflows.

The platform landscape in 2025 segments by company stage and use case. B2B-leaning platforms with built-in CRM: HubSpot (the most common SMB-to-mid-market default), Marketo / Adobe Marketo Engage (enterprise), Salesforce Marketing Cloud and Pardot/Account En...



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Brand Awareness

Brand Awareness

Brand awareness is the degree to which a target audience recognizes, recalls, and associates meaning with a brand. It is measured through unaided recall ("what software comes to mind for managing customer email?"), aided recognition ("have you heard of Customer.io?"), and category-specific top-of-mind surveys, and treated as the top-of-funnel input to every other marketing metric. It is one of the few marketing outputs that compounds without ongoing spend once it's built, and one of the easiest to under-invest in because the ROI doesn't show up in next quarter's dashboard.

The standard measurement frame separates three levels: unaided awareness (the buyer names you when asked the category question, the strongest signal), aid...



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Convertible Note

Convertible Note

A convertible note is a short-term debt instrument that converts into equity at the company's next priced round rather than being repaid in cash. It typically carries four key terms: an interest rate, a maturity date, a conversion discount, and often a valuation cap, combining the speed of a loan with the upside structure of equity. It was the dominant pre-seed and seed instrument from roughly 2005 until 2013, when Y Combinator introduced the SAFE and the market gradually shifted.

The four key terms, with typical 2025 ranges:

Term Typical range What it does
Interest rate 4-8% per year Accrues until conversion; rarely paid in cash
Maturity 18-36 months Note must convert, be repaid, or be extended by this date
Conv...


Article

Succession Planning

Succession Planning

Succession planning is the process of identifying and developing internal candidates to fill key leadership roles when current incumbents depart, planned or unplanned. The discipline covers the CEO and other C-suite positions, key functional leaders, and sometimes board members. Succession planning is typically neglected at early-stage startups (where it feels premature) and increasingly important as the company scales (where unexpected departures of key leaders can significantly disrupt operations) and approaches IPO (where public-company governance norms require formal succession plans). It is the unglamorous discipline that pays off in moments of crisis and is most valuable precisely when nobody thinks they need it.

T...



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Cashless Exercise

Cashless Exercise

Cashless exercise is the option-exercise method where the holder simultaneously exercises options and sells enough resulting shares to cover the strike price and tax withholding. It lets the holder convert vested options into net shares (or net cash) without putting up cash for the exercise, typically requiring a public market or a contemporaneous private secondary, making it standard at public companies but rare at private startups absent a tender offer. It is the practical solution to the cash-binding problem of traditional exercise at companies where the strike-price outlay would otherwise be substantial.

The two main cashless exercise variants:

  • Cashless exercise and hold: holder exercises all options, sells just enoug...


Article

Strategic Investor

Strategic Investor

A strategic investor is an investor whose primary value to the company extends beyond financial capital. The value includes strategic relationships, distribution channels, technology integration, market access, talent, or industry expertise. Strategic investors are typically corporate venture arms (CVCs), large industry players, sovereign wealth funds, or family offices with specific industry focus. The tradeoff is potentially valuable strategic benefits in exchange for typically different relationship dynamics (information sharing concerns, potential competitive conflicts, slower decision-making) compared to traditional financial investors. Distinct from CVC specifically (which is a structural category) but overlapping; ...



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