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...

“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):

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...

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:

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...

IPO

An initial public offering (IPO) is the process of selling shares of a private company to the public for the first time. Listed on NYSE, Nasdaq, or international equivalents, an IPO is traditionally the marquee exit path for venture-backed companies, with investment-bank underwriters pricing the offering, allocating shares to institutional buyers, and the company raising primary capital in the process. It is also one of the rarest exit outcomes statistically, despite getting the bulk of the press coverage.

The standard process runs roughly: file a confidential S-1 with the SEC, respond to SEC comments through 2 to 4 rounds, conduct a [Roadshow] where executives pitch institutional investors over 1 to 2 weeks, price the offering the nigh...