There’s no such thing as a “retired Founder.”

Just one who hasn’t started their next company yet.

I love hearing about Founders that exit, but what I always find kind of entertaining is their story about how they will now finally retire. It’s always something like “I can finally put the stress of running this startup behind me and spend the rest of my days basking in the sun and enjoying life!”

My response is always the same: “That sounds awesome… call me when you want to talk about your next startup!”

They assume I’m being sarcastic. The idea of starting another startup after just finally selling one and prepping for retirement sounds ludicrous!

And yet, inevitably, I get the call. “You know, retirement actually sucks, so I’m thinking abou...

Just when we thought we had finally gotten past all the bullshit of crawling out of startup mode, someone just hit the reset button on us.

“Hop in the Family Truckster, kids, we’re going back to StartupLand!”

Of course, I’m talking about the wholesale disruption that AI just put on nearly every business, and in this case, established businesses that had long since outgrown startup mode, where we thought we were safe and happy.

Startups.com has been around for 15 years (despite our best efforts), and we too have enjoyed being a well-established company that knew exactly what we sold, who our competitors were, and how we got paid.

But probably, just like your startup, all of that changed. Everything we thought was certain a year ago is brand ...

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, ...

There ought to be some kind of test Advisors need to pass before they are allowed to give startup advice.

But there isn’t — literally, anyone can call themselves an Advisor and get away with it. Hell, I’m doing it right now!

Having been in the business of advising startups for decades, I can say this with conviction — most startup advisors are horrible, and they have no idea they are horrible. I’m not talking about bad actors or those trying to do something nefarious. I’m talking about the advisors who actually think they are helping, and instead are doing a lot of damage.

That’s also not to say that Advisors don’t have helpful or useful advice. The problem stems as much from their delivery as from their actual advice. Sometimes, yes, the a...

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):

Large Language Model (LLM)

A Large Language Model (LLM) is an AI system trained on massive amounts of text to predict the next token in a sequence. The prediction capability scales into broader abilities (reasoning, code generation, analysis, conversation, translation, summarization) as models grow in size and training data. Modern frontier LLMs range from 70 billion to 1+ trillion parameters and are the technology underlying ChatGPT, Claude, Gemini, Llama, and other generative AI products that have transformed software since 2022. It's the specific type of foundation model that handles text.

What LLMs actually do (the mechanics):

Tokens, not words: LLMs break text into tokens (sub-word units). "Tokenization" of a sentence might produce 10-...

Quarterly Business Review

A quarterly business review (QBR) is the recurring strategic review at quarter-end covering OKR achievement, strategic initiative progress, trends, lessons learned, and next-quarter planning. Typically a full-day or multi-day session, it's the strategic equivalent of monthly business reviews (tactical financial) and weekly business reviews (tactical execution), and is distinct from "customer QBRs" (customer success meetings with key accounts) despite the shared acronym. It is the leadership rhythm that closes each quarter and opens the next.

The standard internal QBR structure (1-2 days):

Quarter review (half-day):

• OKR achievement: what hit, what missed, why.
• Financial performance: quarterly P&L, revenue, growth m...

Sales-Led Growth (SLG)

Sales-Led Growth (SLG) is the go-to-market motion in which a dedicated sales team drives customer acquisition through outbound prospecting, demos, consultative selling, and contract negotiation. Marketing supports the motion by generating awareness and pipeline rather than directly converting leads. It's the traditional B2B SaaS motion, dominant for higher-ACV products and complex sales cycles, and the counterpart to [Product-Led Growth] (where the product drives acquisition without sales intervention).

When SLG is the right motion:

Higher ACV ($30K+): the deal size justifies the cost of sales reps.

Complex products: requiring consultative selling, demos, technical evaluation, and customization.

Multi-stakeholder buyi...

User Experience

User experience (UX) is the total quality of a user's interaction with a product across usability, accessibility, performance, content, design, and emotional response. It treats the product as the experience the user actually has rather than just the interface they see, covering information architecture, visual design, and microinteractions. The term was coined by Don Norman at Apple in 1993 to capture everything that shapes how a person perceives and interacts with a system, beyond just visual design.

The components of modern UX work cluster into roughly six areas: usability (can the user accomplish what they're trying to do, with what speed and what error rate), information architecture (how content and functionality are o...

Exit Multiple

An exit multiple is the valuation multiple at which a company is acquired or goes public, most commonly revenue, EBITDA, or ARR multiples. Common variants include revenue multiple, EBITDA multiple, ARR multiple for SaaS, or user-count multiple for consumer products. It is used to compare exits across deals, inform founder valuation expectations, and serve as a primary lens through which strategic acquirers and PE firms evaluate targets. It is the shortcut metric most M&A conversations actually run on, despite the existence of more sophisticated valuation methodologies.

The major multiples by business model: SaaS / subscription: typically valued on ARR multiple (annual recurring revenue), with public-market multiples ranging fr...