Business Plan

A business plan is the written document describing a company's business model, target market, competitive position, operating strategy, team, and financial projections. It's used to align stakeholders and guide execution. Modern startup business plans rarely take the form of the traditional 30 to 40 page document; they more often appear as a pitch deck, a one-page Lean Canvas, or a short narrative memo.

The traditional business plan, with its executive summary, market analysis, organizational structure, marketing plan, operations plan, and 3 to 5 year financial projections, originated in mid-twentieth-century corporate planning and remains the format banks and SBA loan officers expect. For startups, the format has shifted. Mos...

Foundations

The foundational vocabulary every founder needs before everything else. This cluster covers what a startup actually is, the categories that distinguish them (bootstrap vs venture-backed, lifestyle vs scale-up), the support ecosystem (accelerators, incubators, agencies), the early credits and grants founders chase, and the structural concepts (founder-market fit, why startups fail) that shape every decision that follows. 21 entries.

If you're new to startup vocabulary, start here. If you're a few years in, this cluster is the conceptual baseline against which everything else is read.

What a startup is

• [Startup], the foundational definition; not every small business is a startup.
• [Early Stage], the spectrum from idea to product-m...

Exits & M&A

How startups end (and what determines who gets what). This cluster covers the major exit paths (IPO, acquisition, SPAC, direct listing), deal structures and terms (LOI, definitive agreement, earnout, holdback, reps and warranties), the rights that affect exit outcomes (drag-along, tag-along, ROFR, lockup), and the mechanics specific to exits (liquidation waterfall, exit multiples, QSBS). 26 entries.

Exits are the moment when years of equity decisions become real money. Founders should know this vocabulary years before they need it.

Exit paths

• [Exit Strategy], the framing question.
• [IPO], going public on a major exchange.
• [Direct Listing], public without raising new capital.
• [SPAC], Special Purpose Acquisition Company.
• [Acquisit...

Foundation Model

A foundation model is a large-scale AI model trained on broad, diverse data and designed to be adapted to many downstream tasks. Adaptation happens via fine-tuning, prompting, or API access. The term was coined by Stanford's Center for Research on Foundation Models in 2021 and now describes GPT-4, Claude, Gemini, Llama, Mistral, and similar models that form the base layer of the modern AI stack. The foundation model is to AI applications what AWS is to web applications: shared infrastructure that powers everything built on top.

What distinguishes foundation models:

Scale: hundreds of billions to trillions of parameters. Trained on hundreds of billions to trillions of tokens of data.

General-purpose training: trained on broa...

AI Strategy

The vocabulary of the AI era of startups. This cluster covers the foundational concepts of modern AI (foundation models, LLMs, generative AI), the architecture and operations that power AI applications (Transformer, training data, fine-tuning, prompt engineering, RAG, context window), the economics that determine viability (inference cost, GPU cost, token economics), the strategic moats AI companies build (data flywheel, AI moat, wrapper vs thick wrapper), the safety considerations (alignment, safety), and current-era terms (multimodal, agents, vibe coding). 22 entries.

This cluster is the freshest in the lexicon. If you're building anything AI-adjacent in 2025, every entry here is operational vocabulary.

Foundations

• [AI Startu...

Every Founder lies about why they are building a startup.

It's not because they are deceptive; I find Founders to be the most vulnerable and honest people I've ever met. It's because they aren't honest with themselves about why they are really building their startups.

When you ask a Founder why they are building, they are inevitably going to give you a stock answer like "I want to change the world!" or "I want to build a huge company!" and, of course, that sounds flowery and wonderful.

But that's not the real answer. The real answer is why are we building anything at all? What is the core purpose within us that drives us so hard to run through walls, empty our bank accounts, and set fire to our personal lives? It's not because we couldn't w...

What is customer segmentation?

Customer segmentation is the process of dividing a large group of customers into smaller groups, based on certain characteristics. It’s also sometimes called “market segmentation.”

Why is customer segmentation important?

Customer segmentation is important because it helps companies market more effectively to their customers. If you want your marketing budget to go as far as it can, it’s essential that you know who you’re marketing to and what they respond to when it comes to advertisements.

For example, if your company had a customer base that included both 14-year-old boys and 45-year-old men, you wouldn’t use the same marketing techniques with the two groups, would you? But you can’t even know that you have ...

What actually happens when the Founder runs out of gas and just can't keep going?

Does the startup just... stop?

In a world where we're all facing some level of burnout, we also have to consider what would happen to our startups if we just stopped contributing.

I've coached nearly a thousand Founders and CEOs through this "outta gas" problem, as well as myself, and I can tell you without question — it's never as bad as it sounds!

Burnout is Inevitable

Look, we all get burnt out eventually.

It doesn't matter what kind of superstar athlete you are in your startup, there's only so much of this pace we can endure before we run out of gas. This shit is hard.

The late nights, the nonstop worrying, the constant "if we can just make it past this mi...

Sometimes, the most important path for a startup has nothing to do with the startup.

As my fellow video gamers know, when you pursue something other than the main questline in a game, it's known as a "side quest." It's a tiny detour that you take to see if there are other riches to be found elsewhere.

In startups, those side quests may feel like a distraction, but in fact, they are often exactly what we need to keep our startups alive.

I'm a giant fan of side quests at startups, partially because my ADHD loves distractions and partially because I've found they pay really well.

The Myth of the Linear Path

The reason we get pushback on taking on side quests is that we seem to keep believing the myth that startups should follow a linear path.

I'm an incredible failure. Or at least, I try to be.

Over the past 30+ years of building startups, my greatest superpower has been my willingness and ability to embrace failure. If we don't understand how important failure is in the startup game, we have almost no chance of ever succeeding.

That's because we're in the game of failure. Not all out failure, like we're going out of our way to tank our startups (although that's kind of the default condition, sadly).

We're in the business of taking massive chances on unproven markets and products. There's zero chance that we're just going to get it right miraculously without running into a massive number of failures along the way.

But that's fine — so long as we get freakishly good at how to fai...