The era of the “Technical Co-Founder” is coming to a close.

It was a good run, friends. There was a time, back in the days of yore, that every aspiring Founder began a perilous quest of finding that one willing technical mind to join them and make their product dreams come true.

They would give anything (usually half the company) to convince them to join their quest, and be grateful to do so.

It was a good time to be a technical person. You were in high demand, everyone was courting you, and you had incredible negotiating power at the most critical time in a startup’s lifecycle — the founding equity division.

But then, well, AI had to come in and ruin it all. What the hell, man?

Why was a Technical Co-Founder a Thing?

For a good 30+ years, ...

“I’ve got dinner tonight with my friends… I wonder which version of me should attend?”

• Do they want to hear about the version that’s stressed out and can’t sleep?
• Or do they want the version that still makes it sound like my startup is doing better than it is?
• Maybe I’ll bring the version that pretends this startup isn’t that important to me and that, instead, I’m just focused on living my best life.

Ah, to hell with it, I’ll just pour myself a vodka gimlet and see which one shows up! Sound familiar?

It’s because every Founder constantly goes through this battle as to which version of themselves they need to bring into the world. And that world has lots of audiences, from spouses and family to friends and colleagues to investors and custo...

Seed Round

A seed round is a startup's first substantial round of outside investment. It is raised to turn a working product into early traction and to reach signs of product-market fit, typically following pre-seed capital and preceding a Series A. It's the round where the company transitions from "we're building something" to "we're building something people want," and where the bar for the next round (Series A) gets established.

The 2025 benchmarks (Carta and PitchBook):

Funding Stages

Everything about raising capital, from the first SAFE to the IPO. This cluster covers every named stage (pre-seed through Series E+), the investor types (VC, CVC, angels, family offices, crossover funds, strategic vs financial), the fund mechanics that drive investor behavior (LPs, GPs, fund life, carried interest), the crowdfunding regulations and platforms, the round structures (up, down, flat, bridge, extension), and the closing mechanics that make deals real. 97 entries.

This is the most thoroughly covered cluster in the lexicon because fundraising decisions compound for years.

Named funding stages

• [Pre-seed Funding], earliest outside capital ($250K-$1.5M on SAFEs).
• [Friends and Family Round], informal first capital.
• [Se...

Startup

A startup is a young company built to find and scale a repeatable, high-growth business model under conditions of high uncertainty. It is distinguished from a traditional small business by its pursuit of rapid growth rather than steady-state operation, defined by what it is searching for (a working, scalable model) rather than by its age, size, or industry.

The two most-cited definitions come from the founders of the modern startup playbook. Steve Blank: "A startup is a temporary organization designed to search for a repeatable and scalable business model." Paul Graham of Y Combinator: "A startup is a company designed to grow fast." Both definitions point to the same idea, that the defining feature of a startup is the search for and...

Competitive Analysis

Competitive analysis is the systematic study of competitors' positioning, products, pricing, customers, go-to-market motion, financials, and strategic moves. It covers direct competitors, indirect competitors, potential entrants, and substitutes, and is used to identify differentiation opportunities, anticipate competitive moves, inform pricing and positioning, and develop sales battlecards that help reps win competitive deals. The discipline is focusing on actionable insights rather than producing exhaustive documents nobody reads. It is one of the most-conducted strategic exercises and one of the most-often wasted.

The dimensions to analyze:

Positioning and messaging:

• How does each competitor describe themselves?
• Wha...

AI Startup

An AI startup is a company whose product depends on artificial intelligence or machine learning as a core differentiator. The category breaks into three distinct archetypes: foundation model labs (OpenAI, Anthropic, Google DeepMind, Meta AI training the largest models), AI infrastructure (Hugging Face, LangChain, Pinecone, Weights & Biases providing tooling), and AI application companies (Cursor, Perplexity, Harvey, Glean building products on top of foundation models). Each archetype has fundamentally different economics, capital requirements, and defensibility characteristics. Understanding which category your AI startup falls into is the first step in evaluating its moat.

The three categories:

Foundation model labs:

• Train and ...

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.

Is it possible to recover from burnout?

Burnout doesn’t mean you’ve failed. It means you’ve slammed into the same wall every founder eventually hits.

The danger is mistaking your own exhaustion for your startup’s fate. Burnout feels permanent. It isn’t. Treat it like a setback, not a stop sign.

The real question isn’t if burnout will happen — it’s what you’ll do when it does. Some founders walk away too soon. Others find a second wind and do their best work on the other side.

We're So Connected — And Totally Lonely Despite endless digital tools, Founders are facing record levels of isolation, and only real human connection can fix it.

You Only Think You Work Hard There's a common misconception about 'working hard' within startups. Let's cha...

What if we had a passion that consumed us more than our startup?

Being a Founder means thinking about your startup constantly. It’s not just work—it’s identity. And over time, it quietly starts to absorb more and more of our energy, attention, and sense of self.

For most people with “normal” jobs, the solution to burnout is taking a break—a vacation, a long weekend, a few nights offline. That works because their jobs stop when they walk away. But for Founders, our jobs never really stop. Our minds don’t clock out at 5pm. Even when we’re technically away, our brains keep running the simulation—funding, hiring, product, growth.

We can’t pretend like we can just flip the switch and shut it off. But what we can do is create a counterforce—somet...