Happy Friday!
Here’s my September playlist. Cheers!
A New Breed of Unicorn
Companies are reaching unicorn status quicker than ever. The median new unicorn is now just over four years old, a 37% drop since 2023, even as the overall herd of billion-dollar venture-backed companies has aged about 7%. The post-GPT cohort is also growing on a different curve. SVB’s data has the 2022 batch going from $2.8M to $5.6M between years three and four, where earlier cohorts went from roughly $2M to $3M, a jump about three times larger at the median. Two caveats worth holding onto: some of that 2022 batch is fast-growing AI wrappers that may not sustain it, and AI has pushed more venture money into non-software businesses that have naturally different growth curves. Meanwhile the previous cycle is being cleared out. Shutdowns hit a historic number, concentrated in the peak-ZIRP vintages, and B2B SaaS alone accounted for more than a quarter of first-half 2026 shutdowns while AI startups became a shrinking share of them. a16z (9 minutes)
How Much Should Founders Get Paid?
How much should you pay yourself? Not a number you can look up. The rule is to incentivize yourself to succeed without ruining your life or your family’s, which for many US founders means earning enough that you can still cover your expenses and save $2,000 a month. Three principles get you there: 1) Feel like an owner, not an employee: OpenAI’s L5 engineers were clearing $1.15M in total comp as of May 2026, and if you benchmark against that you start negotiating with your board like a for-hire CEO instead of an owner. 2) Don’t burn the ships: founders who underpay themselves into personal debt tend to quit early, because a mediocre acquisition looks appealing when you are broke. 3) Don’t overdo it: whatever you pay yourself is a soft cap on what you can justify paying senior hires, so an inflated founder salary inflates the whole payroll. Change your comp when your life materially changes or the company hits escape velocity, not because you just raised a round or a peer survey came out. And bring it to the compensation committee rather than voting on it yourself. NFX (8 minutes)
Home Depot’s Real Moat
$1,000 invested at Home Depot’s 1981 IPO with dividends reinvested is worth about $17M today. The same money in the S&P 500 is about $170,000. Home Depot brought Sol Price’s warehouse club idea to home improvement, but the format was the visible innovation, not the moat. Home Depot hired former plumbers, electricians and carpenters to teach customers how to finish their projects, which manufactured do-it-yourselfers rather than merely serving them. Someone who succeeds at painting tries drywall next, and in company lore a 25-cent washer turned into a $100,000 kitchen remodel. Associates held stock, so good service and their own wealth were the same thing, and thousands of early floor staff became millionaires. The belief is visible in the org chart. Home Depot’s Atlanta headquarters is officially the store support center, which inverts the pyramid: the people closest to the customer sit on top, and everything above them exists to make their job easier. A rival can copy a warehouse in a year. Copying that takes a generation. Read the breakdown in my other newsletter Acquired Briefing. Acquired Briefing (12 minutes)
Founder FAQ: Why Is a Startup Lawyer Not the Founders’ Lawyer?
You may trust your startup’s lawyer. You may like them. They are still not your lawyer, and the moment your interests diverge from the company’s, they are obligated to pick the company. That isn’t a betrayal, it’s the job. Their duty of loyalty runs to the startup and its shareholders, not to you personally. Most founders never feel this, because their interests and the company’s line up almost all of the time. The exceptions are the expensive ones: negotiating your own comp or equity, a founder departure or removal, a secondary sale, your separation terms, a dispute with a co-founder. In those moments company counsel cannot give you undivided attention or unbiased advice, and what you tell them is not protected as yours. Spend the money on a personal lawyer for personal matters. The founders who get hurt are the ones who assumed the friendly lawyer down the hall was theirs. Westaway (4 minutes)
Startup Funding Guides
I’ve put together a series of guides to equip founders to excel at fundraising. These guides break down the deal term-by-term and give you negotiation tips so that you can speak to investors with confidence.
Convertible Note: Guide / Video
Certainty in an Uncertain World
The startup journey is filled with uncertainty. A fractional General Counsel (GC) provides the certainty of on-call legal expertise. Having an experienced GC gives founders invaluable peace of mind. With a seasoned startup legal expert on demand, founders have a steady guide through uncertain legal terrain. The GC acts as a trusted strategic advisor while handling day-to-day legal tasks. This lifts a huge burden off of startup leaders, allowing them to focus on growth with legal confidence. Rather than getting bogged down in legal details, founders feel empowered delegating tasks to an expert and focusing on their vision. Founders sleep better knowing their GC can swiftly handle any legal issue that arises. If you’re curious how a fractional GC can give you peace of mind, let’s talk.
The $2,000/month savings figure is really a personal-runway number, not a lifestyle benchmark. Founders who get into trouble are usually treating company equity as a substitute for personal liquidity.
I see the same mistake in salaried clients — under-saving early because future income is assumed to cover it. Same burn-the-ships logic, different costume.
The number that matters isn't the salary, it's how many months you can personally survive a bad outcome.